Back in June, I wrote a two-part series about my technology choices in retirement. The first part, “Overengineering: A Case Study,” described how I left IONOS after twenty years and rebuilt my web hosting on a cheap private server, Docker, Cloudflare, and Vercel. The second part, “Eight Years In and Still Figuring It Out,” looked at the rest of my subscriptions and the value of leaving well enough alone, including why I chose to keep an old Dropbox subscription rather than spend a weekend sorting through it.

In that first part about overengineering, I wrote that I had traded a system where IONOS handled the server updates, security patches, and backups for one where I have to do all of that myself. Recently, three problems arrived in less than two weeks that I actually had to deal with.

The maintenance I expected

On October 21st, the news broke about a PHP flaw called PHP2Shell. A CBS News headline described it as a bug affecting 70 percent of the world’s websites, and that included mine. Researchers had already built working attacks against WordPress, which runs most of my sites and the ones I host for Marsha and our older daughter.

I started reading the news about the flaw just before going to bed. After Marsha went to sleep, I stayed up, logged into my Docker host, and updated each container by hand. Nothing broke, and afterward I let Marsha and our daughter know their sites were patched.

Five days later, Cloudflare emailed to say that some certificates from a certificate authority could no longer be trusted and asked customers to upgrade the software that runs Cloudflare Tunnels. I run only one tunnel for the container that runs my 1Password Connect server. (For the geeks out there, the Connect server allows apps to fetch secrets in 1Password through a REST API without requiring a CLI or local client APIs.) The upgrade was pretty easy. I took care of it while reading my email in the morning, and the only cost was a later start on my consulting work.

Security updates are nothing new. We all got used to Windows updates years ago, and on our iPhones and Macs the updates mostly happen automatically. On my own servers, nothing happens automatically. When I took over my own hosting, I understood that I would be the one doing these updates, so these tasks were annoying but somewhat expected.

The one I didn’t expect

On October 29th, I got the dreaded email from Vercel stating that my free account had used up its included computing time and would be paused within 24 hours unless I upgraded to the $20-a-month Pro plan. I knew my account had been running close to the compute limit for a while, and something, perhaps more traffic, pushed it over the edge. Unfortunately, I didn’t get to the email within that 24-hour period.

Three of my rebuilt websites lived under that one account, so the pause took them all down at once. Back in June, I wrote that if a rogue nation-state flooded my family’s Christmas letter site with traffic, the Vercel frontend would shrug it off. As it turned out, no nation-state was needed, because a free-tier meter did the job instead.

Once I got the email, I paid the $20 to bring the sites back online and started moving everything to Cloudflare, which I’m told has a free tier that fits my use case better. I started on Saturday with hillwork.us, which is basically a two-page website with a contact form. The migration took me a ridiculously long time for such a simple site, and I suspect I spent more time migrating hillwork.us than all of its visitors have spent reading it.

On Sunday, I blew the entire day on the other two sites (time-restricted.com and paos.us). Boo. I sat in front of the AI vibe coding the solution, manually tweaking settings in the Vercel and Cloudflare consoles, and testing the sites. Because I let the AI do the work, I still don’t really understand how Vercel runs my sites differently from the way Cloudflare does. I’m like someone who drives a car and can use all of its features but doesn’t know how to fix it. When the check-engine light came on, I handed the keys right back to the AI.

Once all three sites were running on Cloudflare’s free tier, I canceled Vercel Pro. While I expected it would run me until the end of the month, they ended up refunding me $18.67 of the $20. So, in the end, I only spent $1.33 on the Pro upgrade. I guess that was a pretty minimal hard dollar cost.

However, the real cost was just another blown Sunday that I’ll never get back. I thought I had escaped most of those lost Sundays when moving from a suburban home into an urban condo with no old fixtures, building exterior, or landscaping to maintain.

Letting sleeping dogs lie

The last two weeks just provided more proof of the value of letting sleeping dogs lie. I do have to recognize the legitimacy of problems I had to address. PHP2Shell was a global event, certificate maintenance is a real thing, and Vercel has to make money. (Vercel is also just total magic, and I’m glad I got some experience with it!)

Saving money was part of why I left IONOS, but my main reason was that my plan made anything beyond old-school PHP awkward. I wanted to use modern languages and frameworks. However, to be honest here, I haven’t really used much modern stuff yet. The only new things I built since moving to the new setup were front-end migrations of three websites that were already running on IONOS. The desire to modernize didn’t produce much of the geek satisfaction of building new things, but it did create a bunch of low-level admin work.

Looking back, I would have left all the old historical stuff on IONOS where it was and used Vercel and Cloudflare only when I wanted to attack new, modern projects. So far, I haven’t really done any. These two weeks just made me further question why I did any of this modernization at all. And, of course, I still kept my Dropbox subscription intact.

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AI disclosure: I used AI tools during the drafting and editing process to help clarify structure and language. All ideas, judgments, and final wording are my own.

The part everybody is talking about

I have to admit that I am joining the crowd of people excited about Instinct AI. I’ve used OpenClaw, and I’m now using Hermes instead on my dedicated Mac mini. Unlike these agents, Instinct runs in the cloud. Like OpenClaw and Hermes, Instinct reads email and calendars and can operate with very little guidance. In my case, it only sees a separate Google account I set up just for AI, which I explain below. As a retired person who isn’t always chained to a desktop computer, I particularly appreciate the ability to communicate with my AI agents using iMessage. For example, Thursday morning I got my normal 7am reminder of my calendar, including commute time and elevator/garage transaction time.

Unlike Hermes, Instinct needs no crontab, MCP integrations, or .env files, because it was designed for end users, not just developers and power users. My problem with all of the AI agents I’ve played with, including Instinct, is that it remains hard to compartmentalize what the AI can see and do. I’d like more turnkey ways to limit access to data, secrets, and payments, while making it clear to me and to others what I’m doing versus what the agent is doing.

Credentials are only a start

A lot of people think these AI agents are secure because using them doesn’t require handing over any passwords. However, even though I haven’t given my AI agents my Google password, I’ve so far “authorized” them to do a lot.

Security conversations about AI often start with credentials because they are familiar. Earlier this year, I wrote about keeping my API keys away from Claude by moving them into 1Password, and that work was worth doing. However, the bigger exposure is the data an agent can reach after login. “Read my email” is an easy permission to grant, yet it covers years of personal correspondence, business discussions, receipts, and travel confirmations. The same is true of Google Drive, where I may want help with one condo project without exposing my financial records, personal letters, or medical reports that I happen to store in the same account. An agent reading those files isn’t necessarily being malicious. It might simply be trying very hard to be useful by looking for more context.

I think of AI access less as a password-management problem and more as a compartmentalization problem. I am concerned about what my AI can see and do after it gets into my accounts. I want to ensure that keeping my data secure is built into the system rather than dependent on the AI following instructions in a prompt.

What I did for the condo EV project

An example of compartmentalization came to me while working on my condo’s EV (electric vehicle) committee. We are working on a shared charging system for the building. I wanted AI to help analyze long email threads, proposed agreements, newsletters, owner communications, and the condo association’s governing documents that constrained what we could do. The easiest approach would have been to connect an agent to my everyday Google account and tell it where to look. I did not want to do that because I didn’t want other aspects of my personal life to be accidentally shared with other members of the EV committee or the community as a whole.

Instead, I connected Instinct AI to a separate Google account that I created just for use by AI. I forwarded the relevant email threads to that address and shared only the relevant Google Drive files with it. These are committee business threads rather than personal correspondence, and I avoid forwarding anything personal. The other committee members also know I use AI to help with this work. By forwarding and sharing selectively, I drew the boundary around what the AI could actually see. I didn’t want to rely on some instructions in a prompt telling the AI to please stay within scope. I know from experience that AI can often “forget” these types of instructions.

I took the same approach with my calendars. I used Google Calendar’s sharing feature to explicitly share my other calendars with the AI account. A couple of my consulting clients only allow free/busy information to be shared across accounts, so for those calendars the AI can see when I’m busy but not what the meetings are about.

There is a tradeoff with this approach. I have to choose what to forward and what to share. As new information comes in, I find that I have to remember to forward an email to the agent. But that small amount of friction also serves as a review step, forcing me to define the information the AI uses. Personally, I would rather make that choice explicitly than discover later that an agent decided an unrelated piece of very personal information looked relevant to share. Of course, the separate Google account is also a viable attack target, but an attacker who got into it would find only what I chose to give it.

Even these forms of compartmentalization have limits. Anything Instinct reads in the AI account, or anything I tell it directly like my home address, can end up in its memory. Revoking its access later doesn’t necessarily erase what the AI has already learned. The company behind Instinct can also see whatever I put in the AI account. The separate account allows me to decide what data goes into the compartment, but it doesn’t make what’s inside the compartment private.

An AI needs an identity people can recognize

I have taken the separation one step further. The Google identity has its own email address and even its own avatar in Gmail. I think this separation is useful for both my recipients and for me. My recipients can clearly see when a message is coming from my AI and not me personally. I also appreciate the audit trail, so I can see what the agent sent separately from what I sent.

For the committee work, though, I rarely let the AI send anything on its own. I prefer to review every message first, send it myself, and disclose that I used AI.

There is a risk to using a separate identity. Because the AI account has its own email address, anyone can send it a message, including one crafted to misinform the agent or trick it into taking an action. With little in the account and very little going out without my review, the risk is somewhat contained but not eliminated.

I admit that this setup is way more manual than it should be. I wish agentic AI products better supported agentic identity with clear attribution and a visible audit trail as basic features. So far, I haven’t found one that does, and until I do, I’ll live with what I’m doing.

A separate vault limits the blast radius

Instinct AI comes with its own vault for passwords and credit card numbers, but I have kept it empty.

In my personal life, I use a combination of Apple Passwords and 1Password (more on this topic in some future posts). I am looking forward to the Instinct AI integration with 1Password, which is “coming soon.”

To do things on my behalf, the AI sometimes needs to see or act on data in my online accounts. Just as I’ve set up my AI agents to use their own Google account, I’ve also set up a separate 1Password account for Hermes containing certain credentials for online services, including some where I’ve stored credit card numbers. Truthfully, this 1Password account also still holds my Chase Ink card number for historical reasons, and I probably should clean that up one day. Even if the 1Password authorization flow makes a password or credit card number invisible to the AI model, I still want a hard ceiling on what I could accidentally authorize.

This is partly protection from the agent, but it is also protection from my own human error. Even as a self-proclaimed power user, I sometimes get prompt fatigue, approving routine requests perhaps too quickly. For me, having a separate vault protects me from those moments of inattention that could inadvertently cause me more harm than necessary.

Restricting credit card usage

The one area where I still don’t really trust AI is unfettered access to credit cards. I do not want an agent to receive my primary credit card number and then rely on conversational instructions about spending restrictions. I think limits should exist within the payment system itself, outside any instructions I give the AI.

I like the direction Link (a service by Stripe) is taking to protect purchases by AI agents. Link is now a preferred payment method for many AI vendors, and I’ve used it a lot for setting up my development environment. Even though I’ve authorized Instinct to pay for services with Link, that authorization doesn’t let the AI spend freely. Each purchase is a separate request for a specific amount from a specific merchant, and nothing is charged until I approve it with biometric authentication (Face ID) using the Link app on my iPhone. Link pays the merchant with a one-time virtual card number, so neither Instinct nor the merchant ever sees my real card number. In the future, I expect to be able to pre-authorize purchases within limits I set for the agent.

The screenshot below shows the Link prompt on my iPhone to approve a purchase Instinct attempted on my behalf for a digital download from itch.io. The request would have expired within the hour without my approval.

I also like Capital One’s merchant-specific virtual card numbers. An eligible virtual card number can be used with one merchant, managed separately, and deleted or replaced without changing the physical card number. Marsha and I already use a bunch of these virtual card numbers for online shopping without AI.

I don’t give these virtual card numbers to my AI agents directly. Instead, I store each one in the merchant account where it belongs. This way, an agent logging into that merchant account could use the card already on file. If anything goes wrong, the number only works at that one merchant, and I can delete it without touching my real card. The tradeoff is that an agent logged into one of those accounts could still buy almost anything that the merchant sells. In my case, the most extreme examples are Target and Walmart, which each have their own Capital One virtual card number, but they also sell just about everything. In these cases, locking down to a single merchant protects the card number itself more than my wallet!

For now, I don’t let Instinct log in to my merchant accounts, because I’m not ready to put my credentials in Instinct’s vault. Hermes, by contrast, can already use its own separate 1Password account.

Link limits how much an agent can spend and when, while these virtual cards from Capital One limit where. Both are useful because they turn a vague instruction into an enforceable boundary. “Do not spend more than $200” is merely advice if it exists only in the prompt. A card that cannot be charged more than the approved amount, or that cannot be used anywhere but an approved merchant, is a control.

The product lesson

All of the companies in this ecosystem are solving pieces of this AI access problem, but I feel the customer education is still limited. For example, I like the messaging around how products like 1Password keep the LLM (large language model) from seeing passwords, and that protection is genuinely valuable. However, I fear that people can be left with the impression that the larger access problem has been solved (and it hasn’t). The password may be hidden while all of my emails and files remain broadly available after login. Some of the tools for narrower access already exist. Google Drive, for example, lets an app request access only to the specific files a user chooses, but agent products tend to ask for everything because broad access makes them more useful at the outset.

I would like the products to ask a more useful series of questions around agent identity, including:

• What data is accessible?

• For how long?

• Can it send messages or impersonate a human?

• Can it make purchases without separate approvals?

• What is logged?

• What can be revoked when the task is done?

It would be great if the technology could take care of these points, rather than leaving it to very manual (and human) controls like the ones I’ve hacked together operationally. Ideally, a single service would let me create an agent compartment with an independent identity, a small collection of entries, explicit usage rules, expiration dates, and an audit history.

The rule I am converging on

I do want AI to read my email and my documents. I do want it to log in to services and handle more routine work for me. I am not trying to keep agents isolated to some toy sandbox where they are unable to do anything useful.

I get that I’m in the minority with my caution. Most people will click Connect, approve a login, and keep going.

The compromise I’ve reached is to give AI its own identity, deliberately share the data that it needs, give it its own vault with a discrete set of secrets, and use payment systems with built-in controls. I also want it to be clear when the AI is authoring correspondence, with everything auditable by me. I want to be able to revoke access when the work is done. Put simply, I want my AI to get only what the system itself enforces, not what a prompt asks it to respect. I just wish the products themselves made it easier to do all of this.

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AI disclosure: I used AI tools during the drafting and editing process to help clarify structure and language. All ideas, judgments, and final wording are my own.

Last week I wrote about our old cat Hank, whom Marsha brought home from the Humane Society once she realized what could happen to him otherwise. What I didn’t mention is why Hank had been on my mind. Our older daughter in South Carolina just adopted a stray 80-pound dog. Watching the ensuing drama evolve from a distance, I had a pretty good idea how the plot would thicken.

A park dog

It all started one afternoon after our daughter and her husband finished a round of disc golf. As they were leaving the park, some people at a Little League practice asked whether they knew who owned the dog that had been wandering around for hours.

Our daughter, being the take-charge person that she is, decided she would take the initiative to ensure the dog could get to animal control. Unfortunately, animal control closed at 5pm. The police told them that unless the dog was dying or attacking someone, they couldn’t get involved. A vet scanned him for a microchip and found an owner and an address, but when they drove to the address, the house was boarded up and looked like nobody had lived there for years. Our son-in-law left a WhatsApp message to both his parents and us, expressing his thoughts. “This dog is like super well groomed. So like clearly someone is looking after this dog.”

With nowhere else to take him, the dog spent the night at their place. Our daughter bought the dog a stuffed sloth and a bone so he would have some company that first night.

The shelter

The next morning, our daughter took the dog to the local shelter. It had been open for only two hours and had already taken in seven dogs, including this one. The staff had recognized the pattern right away. “Park dog? Neutered? Puppy? No collar? Yup okay. Can we call you in a week?” The staff didn’t seem optimistic that an owner would come to claim the dog.

Unfortunately, the shelter doesn’t accept outside toys for the dogs to take into the kennels with them, so the staff threw the sloth away right in front of the dog, much to our daughter’s dismay. She also had to sign paperwork that would make the dog available for adoption after a ten-day stray hold.

Timing was of the essence. The staff told our daughter that the dog was more likely to be adopted than claimed by a prior owner, and that the shelter couldn’t guarantee the dog a space there for more than ten days. Later that day, our daughter learned that a second dog, a young and well-kept female pitbull mix, had been found near the same park and was the very next dog logged in after hers.

Personally, I was pretty surprised by how routine all of this is. In Portland, it just feels like abandoned dogs are a lot less common, but perhaps I am just “sheltered!”

The trick

I could tell how this story was going to progress. Once our daughter had brought the dog home and given him a sloth and a bone, I knew the deal was done.

I texted her that it was a little bit like Fishy. “The trick is to never get attached,” I wrote, “but I understand what happens once you click over.” She wrote back that it “totally does give fishy,” and that her husband could attest she had cried when the shelter took the stuffed sloth away. She added, “Yeah the trick was 1000% not to get attached.”

Marsha was out when we traded those texts, so once Marsha got home, our daughter called, and the three of us went over the whole thing again. Before long we were talking about Fishy.

Fishy

When our younger daughter was somewhere around ten, a friend’s mom gave her a betta fish. My first reaction was about how rude it was to give such a “gift.” When I was growing up, my mom kept a family fish tank and bought fish for it from the pet store. The ones that survived grew old and big, but a lot of them just died, and I watched it happen more times than I wanted to. I told Marsha immediately upon learning of the gift that we should give the fish back. When that idea went nowhere, I joked that we should just flush him before any of us got attached.

Of course, we kept him. Our daughter named him Mushu, after the dragon in Mulan. Before long, all of us just called him Fishy. He came to us with an infection in his swim bladder, and he had to pump his fins hard just to reach the top of the tank to eat. I bought him a tank heater, some rocks, and a plant whose leaves he could rest on during his climb. I bought medicine for the infection, and between the two of us, Marsha and I made more trips to the pet store in those few months than I care to count. We were both fully invested in the drama.

Fishy didn’t make it. Our younger daughter and I buried him together in the yard. Afterward she sadly told Marsha, “I think I know why Dad wanted to flush the fish.” The joke had never really been about not caring. I knew that once we took him in, we would do everything we could to keep him alive. I’d been through the experience of having fish with preexisting health issues, and I knew it still hurt to lose them.

Our older daughter was old enough to remember Fishy. So when she cried over a stuffed sloth at the shelter, she knew exactly what had happened to her. So did I.

The list

With her take-charge inclination, our daughter didn’t simply follow her heart. She sent us a numbered list of everything that would need to happen before agreeing to even foster the dog. She would check with her landlord about an extra security deposit, get a new renter’s insurance quote for a pittie mix, line up friends around her travel schedule, work out a budget with her husband, and ask whether she could crate him at her office for a one-week trial. She also planned to wait until he went up for general adoption, in case his owner came for him first. The list didn’t help her sleep. She was still thinking about the dog constantly.

Soon after, our daughter and her husband decided they would bring the dog home.

The original owner

As it turned out, the owner did come forward during the stray hold. He admitted he could no longer take care of the dog. At first, he refused to sign the paperwork releasing the dog, because he knew what a release could mean for a dog at that shelter. He signed only after the staff told him that our daughter was ready to take the dog home. I don’t know his circumstances, and I’m not in a position to judge him. What I do know is that he kept that dog well groomed until the end, and when it mattered, he wanted to know the dog would be safe.

It reminded me of Hank, who was taken from his mother early to be sold at a pet store. The people who bought him at the pet store wrote wonderful things about him when they gave him up for adoption but just couldn’t keep him. I hope Hank had a happy home with us, and later with my mother-in-law.

After the original owner left the shelter, everything moved quickly. After receiving the call, our daughter made an appointment at a local pet groomer and then picked him up. Nearly every message we’ve received since has been a photo of the dog. He is huge.

Oki

The dog’s microchip had a name on it that he never answered to. Our daughter renamed him Oki, a shortened version of Marsha’s mom’s maiden name. To me, I felt it was appropriate for an Asian woman to be heard calling for “Oki” at the dog park.

Of course, Oki ended up with our daughter because she got attached. It happened to Marsha with Hank. It happened to all of us with Fishy. In the photo I attached to this post, Oki is sitting on her couch at home with his tongue out, looking very much like he belonged there all along.

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AI disclosure: I used AI tools during the drafting and editing process to help clarify structure and language. All ideas, judgments, and final wording are my own.

A surprise gift

Marsha and I were married in November of 1995, so her birthday the following March was the first one we celebrated together as a married couple. Before we joined our accounts together, I always felt like I could simply throw money at a gift. Now that any money I spent on a gift was spending her money too, I felt like I had to get her something she couldn’t buy on her own.

Surprisingly, she had floated the idea by me once that it’d be fun to have a cat. However, I immediately shut down the idea. As a child, I always grew up with and loved our cats, but I had severe allergies and spent most of my childhood on serious allergy medication. Marsha was understanding of my desire to breathe freely (😜), and never brought up the idea again. So getting us a cat was my great idea for her birthday!

So I went to the Humane Society the day before her birthday and selected Hank. He was a short-haired black-and-white cat, unusually clean and active compared to the others there. I expressed my interest, found a beanie baby that looked just like him, and put it in a box with a bow on top to present to Marsha the next day.

Marsha was touched but also reassured me we didn’t have to go through with it. But I had already picked the cat and suggested we simply go check him out.

The visit did not go the way I expected. While Hank was affectionate and rubbing against me, he really didn’t pay much attention to Marsha. The chemistry just didn’t seem to be there at the time. So rather than force me to put up with allergies, she decided it would be better to just go home without him.

The next morning, the two of us were standing side by side at the double sinks in our bathroom. I was about to head out for a business trip. Seeing my reflection in the mirror, Marsha noticed a slight smirk on my face. When she asked what I was thinking, I said, “Poor Hank. He might actually get euthanized because he didn’t suck up to you.”

I was mostly joking. Hank was so clean and lively. I just felt sure that someone would pick him out the way I had, so I wasn’t really worried about him. I did feel bad knowing that not every cat in the facility would be so lucky, but I didn’t at all doubt that Hank would get adopted.

We were still newlyweds then, so we were still at the phase where we’d talk every night when I traveled on business. (That ritual did not last!) Marsha never mentioned Hank in any of our nightly calls. Still, when I got home and opened the front door, Hank was there to greet me. After our conversation the morning I left, Marsha went back to the Humane Society to pick up Hank, feeling guilty. She kept the whole thing quiet to surprise me, and was I surprised!

New experiences

Marsha had never owned a cat before. I laughed when I saw that she bought him a cat bed and a scratching post. The cats I grew up with slept and scratched wherever they pleased, mostly on the furniture. I told Marsha I never had a cat that would use either one. Hank was the exception. He loved his bed and shredded several scratching posts over the years. Of course, having the bed and scratching posts never stopped him from sleeping with us or wrecking the furniture, too.

One lesson we learned was the need to take the cat from adoption straight to the vet to get rid of fleas. Hank had a pretty bad case of them, so we did have to rid both him and the condo of fleas shortly after bringing him home.

The good news is that my allergies didn’t turn out to be too bad with Hank. His short hair helped. I also learned that bathing cats is totally the move. Hank didn’t like getting wet, blow-dried, and having to lick himself for a long time afterwards. However, once all of that was over, he was always very affectionate with me. I believe he liked being clean and appreciated my help, even if he didn’t enjoy the process. Bathing Hank became my job, and it stayed my job for the rest of his life.

He was also always hungry. Our vet told us his weight should top out at eleven pounds, which meant keeping him on a strict diet. Unlike other cats I had known, Hank never nibbled. He ate all the food in his bowl in one sitting.

Hank was smart in the ways that count. Back then, we kept chlorine tablets in our toilet tanks, and we always kept the toilet lids closed. A friend staying with us didn’t know that rule and left a toilet lid up. Curious Hank must have had a drink. He threw up afterward, but he did it on the tile floor rather than the carpet or the furniture. We were relieved to have such an easy cleanup.

Making room for babies

In those early years, Hank always followed us from room to room like a dog. Before our daughters were born, we had plenty of time and energy to play with him. That changed when Marsha was pregnant with our older daughter. In preparation for our new baby’s arrival, Hank loved curling up in the bassinet and settling into the car seat stroller, as if he were testing them out. Marsha’s pregnancy seemed to change him a little, too. Perhaps he picked up on something different about her, or perhaps he sensed that he was about to lose his place as the center of attention.

Hank made his feelings known to us the day we brought our older daughter home. He had peed on my side of the bed, something he had never done before and never did again. I spent part of our first evening home with our new baby at the coin laundry, washing all of our bedding. I think Hank made a one-time statement.

Whatever grievance he had, it didn’t last. From then on Hank was our older daughter’s buddy. He loved sleeping near her as a baby and kept it up when she was a toddler.

By the time our younger daughter arrived, we were fully absorbed in raising two kids. We didn’t play with Hank nearly as much, and the girls had each other for company. Hank was still part of the family, but I could see him changing as he slipped further into the background of a busy household.

Hank finds his person

When we moved out of our house in 2001, we shut Hank in the powder room so the movers could leave the front door open. In the chaos of the day we forgot about him. Somehow he figured out that he should climb into the sink to relieve himself, and he saved us a great deal of cleanup then, too.

In 2001 we moved to Seattle, settling in Newcastle, about six miles from Marsha’s mother, Nori, in South Bellevue. Marsha’s dad passed away shortly after we arrived, and we saw Nori frequently in those years.

Hank still didn’t get the attention he once had, and I worried that he wasn’t as happy as he could be. Around that time a coworker of mine mentioned that she really wanted a cat. She was single, and I began to wonder whether Hank would be better off in a quiet home with one person who could make him the center of her world again. I floated the idea of giving him to her. At the time, Marsha agreed this might be best, too.

Nori would not hear of it. She told Marsha we could not simply give up a member of our family. That settled the matter, and Hank stayed with us. Looking back, I find it a little funny that the person who insisted Hank belonged with us was the one he would eventually choose.

At one point we considered moving to a different neighborhood close by, and we put our house on the market. While we showed it, we asked Nori to keep Hank. I don’t think she ever meant to keep him. She was simply doing us a favor.

But Hank was a warm and friendly cat who liked to follow people around, and Nori’s life had grown quieter since Marsha’s dad died. Marsha’s brother, a truly wonderful human, had moved back in with her, but this was long before working from home was common. His job involved a lot of travel, and between work and his close circle of friends he was often out. That left Nori and Hank with a great deal of quality time together.

The house never sold, so we took it off the market and stayed put. When it came time to bring Hank home, Nori was noticeably reluctant to give him back. Some time later we decided to move back to California so I could join Barracuda Networks. We told Nori that renting would be much easier without a cat, and she graciously agreed to do us the “favor” of keeping him.

Hank lived with Nori from around 2004 until 2010, and he became the center of her attention in a way he hadn’t been with us since before the girls were born. She played with him at 10 p.m. on the dot every night. She grew cat grass and cut it so he could have a little “salad” with his meals. She refused to vacuum while he was napping. She also felt sorry for him on the strict diet we had kept him on, and the eleven-pound cat soon settled in closer to fourteen. He seemed perfectly content with the trade.

The clearest sign of how happy he was had to do with the door. When Hank lived with us, he was always looking for a way to sneak outside. Once he moved in with Nori, he never tried again. I think he understood that his job was to be right there with her.

We didn’t lose touch with him. Every summer, until club sports took over the girls’ schedules, Marsha brought them up to Bellevue for a month. Marsha and the kids spent plenty of time with Hank. We spent holidays there, too, and whenever I visited, bathing Hank was still my job.

Hank’s final weeks were not easy. He developed feline diabetes, and in 2010, as we understood it, complications from the disease left Nori and Marsha’s brother with the hard decision to put him down. Nori was 80 at the time, and afterward she never wanted another pet. She told us she didn’t want anyone else to die on her again. What began as a birthday present I hoped Marsha couldn’t buy for herself turned into a lifetime with a cat who belonged to all of us, and who, in the end, found his way to the person who could give him the most.

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AI disclosure: I used AI tools during the drafting and editing process to help clarify structure and language. All ideas, judgments, and final wording are my own.

Reflections. Starting with the sad news, one of my best friends from MIT, Elliot Schwartz, passed away on September 24. For the last couple of years, we had been doing monthly video calls that ran for hours at a time. We started them after Elliot and I discussed a mutual desire to invest more in relationships (see Navigating the Friendship Recession). During those calls, we covered just about everything in our lives. Elliot always loved gossip, so he even enjoyed hearing stories about my day-to-day life here in Portland, and he had plenty of his own stories from his work in volunteering for the Democratic Party in Maine, his national ice skating judging and international officiating, and helping lead the data analytics for the US Olympic team.

His death was pretty unexpected to me. When we scheduled our next call for September 30, I assumed we would be catching up after I got home from my trip to Bend. Then, in early September, while I was visiting our daughter in South Carolina, Elliot shared the news of his brain disease with our friend group over text. On September 17, he let us know that he would be going in for surgery on Tuesday, September 22. Because he was careful never to use the word “cancer” with us, I had no idea from his description how serious it was. On the morning of his surgery, we were texting each other while he was in pre-op, and he asked how I was doing. He passed away two days later, and I spent part of my time in Bend arranging a last-minute trip to New York for his funeral.

In Jewish tradition, burial happens as soon as possible after a death, out of respect for the person who died, and someone stays with the body until the burial. Elliot’s service was originally planned for Tuesday or Wednesday, but it ended up on Thursday, October 1, on Long Island. Our close MIT friend group all came out to say goodbye.

Looking back, I’m grateful that Marsha and I had a chance to visit Elliot at his new home in Maine in 2023, and I’m happy that we started our monthly calls. At the same time, this whole thing still feels a bit surreal. Elliot never expected to live a long time, since his dad died just shy of 59. Still, Elliot was looking forward to having more time, and he was already planning trips to Canada, Belgium, and Kazakhstan. So while he had some expectation of a shorter life, this all came so much sooner than any of us anticipated. On the evening of September 30, when we would have been on our call, I was on a flight to New York. I looked at Marsha and said, “I need to remove my calendar reminder of my monthly call with Elliot.”

Elliot was always pretty much a “matter-of-fact” type of guy, and I know he wouldn’t have wanted to suffer. Given what actually happened medically, I know the quickness of his decline was better for him. It just feels weird.

Health. On a more hopeful note, my second stent placement on October 5 seemed to go OK! Just like with my first stent on August 14, I totally fell asleep right after getting home. By the next day, though, I walked with a neighbor to Bruja-ja, a comedy show at Brujos, a local brewpub. The irony was that my meal the day after a heart procedure wasn’t the most heart healthy, as I thoroughly enjoyed a chorizo platter from El Viejon, the Mexican food pop-up there.

For this first week of recovery, I’ve been told not to lift anything heavier than 5 to 10 pounds. I’m looking forward to the 12-week cardiac rehab program and to the next six months on dual antiplatelet therapy, which I’ve been told is what I need to complete to regain eligibility for my kidney transplant. (For background, see Returning in 2026, A Spring Catch-Up, The Detour, The Fourth of July Grab Bag, and Stage One.)

Finance. Of course, healthcare isn’t a fun topic for us right now in the financial sense, either. In less than a month, we start open enrollment for individual marketplace health plans. We’ve already been notified that our premiums will go up by 37 percent in 2027 (from $1,736 per month to $2,380 per month), and our individual out-of-pocket maximums will go up from $7,500 to $12,000.

So, over a full year, we’re looking at another $7,728 of premiums (from $20,832 to $28,560), and I will certainly need to pay that extra $4,500 to reach my out-of-pocket maximum. The new plan also drops CVS retail pharmacies from its network. We have a CVS in the neighborhood, but I generally prefer to use Amazon, Costco, OHSU Pharmacy, or the nearby Safeway anyway.

I considered upgrading to a Silver or Gold plan, since the lower out-of-pocket maximums seem to make up for most of the premium differences between the plans. However, all bronze plans on the Oregon marketplace can be paired with a health savings account, and I want to keep that deduction, so we’re sticking with bronze.

Business. Beyond our personal finances, the bigger issue is the overall business environment for healthcare insurance in Oregon and elsewhere. The enhanced ACA subsidies expired at the end of 2025. The impact was “adverse selection,” where healthy people forgo health insurance altogether, leaving a less healthy population participating in the plans. In Oregon, the individual market shrank from about 161,000 enrollees in 2025 to about 140,000 in 2026 (Insurance Business), and Moda’s own rate filing projected that “lower morbidity individuals will be more likely to drop coverage” (Oregon DFR).

Providence and PacificSource are both exiting Oregon’s individual marketplace for 2027. Moda is exiting eight Oregon counties. Surprisingly, Bend is impacted here, as Deschutes County is one of the eight (Bend Bu lletin). Multnomah County is still covered, but Moda requested an average rate increase of 25 percent, and the state approved individual market increases averaging 21.6 percent (Oregon DFR).

Moda lost money on individual plans here, too. According to its 2025 annual statement, included in its rate filing with the state, Moda’s Oregon individual business had an underwriting loss of about $14.9 million in 2025, or roughly $38.54 per member per month (Moda rate filing).

Politics. In the middle of all this, we received a $1,000 check covering both Marsha and me, along with a letter signed by Donald Trump. We received the check because we, along with others who are above 400 percent of the federal poverty line, purchased coverage through HealthCare.gov without subsidies. The letter calls the money a “one-time $500 REFUND” of fees that the Biden administration “overcharged you to fund the operation of HealthCare.gov.”

I don’t think this was the right thing to do from either a policy or a messaging perspective. On policy, these refunds are going to people like us, who can afford to pay, while the enhanced subsidies for everyone else have expired. On messaging, most of the letter reads as criticism of the previous administration.

I was surprised that taxpayer funds could be used to send a letter like this, but apparently the President is exempt from the Hatch Act. And because the letter came with an actual check, it apparently isn’t considered pure political messaging, even if it reads that way. The timing was also hard to miss, since these letters started going out on September 30, about five weeks before the midterm elections (CBS News).

PNW. My last few weeks haven’t been all bad, though. In late September, I had a great time in Bend with my Latitude friends Wayne, Kent, and Larry, the same group I went to Sedona with last year (How Guys’ Trips Change As We Age). Kent named the trip the “2026 Mancation Oregon.” We hiked Steelhead Falls and Smith Rock, visited Tumalo Falls and Sparks Lake, and made the rounds of a number of brewpubs, including Wild Ride, 10 Barrel, and Deschutes. We also took a kayak tour with Wanderlust Tours, where our guide, Isaac, was great and knew a lot about both the natural surroundings and the local history.

The Smith Rock hike was a highlight and also particularly tiring. According to my Apple Watch, the hike involved 1,212 feet of elevation gain, and my heart rate peaked around 150 beats per minute. I think I went over the heart rate guidance I’ve been given by the cardiologist, but I was fine!

Overall, we followed a fun itinerary that Kent prompted Claude to assemble. The agenda was perhaps a bit too aggressive. On the first day, we skipped Pilot Butte, dinner at DRAKE, and a nightcap at Crux Fermentation Project because the guys’ flights got in late. On Saturday, we had a late lunch at the food carts at Wild Ride after Steelhead Falls and Smith Rock, so we were still full when we got to dinner at Ariana. I wish I could have tried the tasting menu, but the butternut squash soup and the scallops were good. On Sunday, we skipped Todd Lake after Tumalo Falls and Sparks Lake, and we also skipped dinner at Zydeco Kitchen & Cocktails. As we fell “behind” schedule, we kept opting out of things. The good news is that we never ran out of stuff to do!

Tech. Of course, we settled up via Splitwise again this year. We all paid for different things during the trip. I covered the rental van, Wayne booked the kayak tour, and we each picked up meals, but Larry booked the Airbnb, which was the biggest expense, so the rest of us owed him. Unfortunately, we tried Splitwise’s native way of settling up, and it was totally janky. For some reason, the Plaid connection to my bank failed, and I had to reauthorize it.

On top of that, Larry could only withdraw $500 per week through the integrated payment partner. Between my $483.57, Kent’s $582.12, and Wayne’s $520.03, Larry was owed $1,585.72, so it would take him at least four weeks just to get his own money out, which was super lame. We should have just used PayPal, Venmo, or Zelle rather than the native Splitwise payment features.

So that’s the last few weeks. I lost one of my best friends, got a second stent, and am facing higher healthcare costs. Still, I also had a great trip with old friends and learned a lesson about payment apps. There were highs and lows and a lot in between. I’m still processing everything.

Happy Double Ten to everyone who celebrates it!

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AI disclosure: I used AI tools during the drafting and editing process to help clarify structure and language. All ideas, judgments, and final wording are my own.

Editor’s Note: This is the fourth of four posts continuing where “Not Forever, Just for a While” left off. Previously: Asta Networks, AskMe, and the seven months off. This post: All Star Directories (my first consulting client), and the drive back to California.

I still don’t know what I want to be when I grow up.

That question lingered on in 2005, my last year in Seattle before returning to Silicon Valley. However, raising a family doesn’t leave infinite time for experimentation, and seven months off made me realize that it would be easier to build on what already came pretty naturally to me, rather than to pursue new patterns like running a photo kiosk business. All Star Directories, my first consulting client, was not a real answer to my long-term question, but it did help me see the path I should take in the short term.

I closed my last post with a phone call from an acquaintance, referring me to one of his friends looking for some contract help. That friend turned out to be the founder and CEO of a startup called All Star Directories. Before we had our first face-to-face meeting, he’d already done a bit of backdoor reference checking both with an old Microsoft colleague who happened to be one of AskMe’s founders, and his IT/Ops Manager, who happened to work with me there at AskMe.

While I expected a more traditional interview, he basically told me what he was looking for, asked me if it sounded interesting, and presented me with a contract. So, without any sort of sales pitch at all,, All Star Directories became the first consulting client of Hillwork Group, LLC. (I later dropped “Group” from my company registrations when I realized I never wanted employees!)

The business

All Star Directories ran a set of web properties that cataloged schools by field of study, including nursing, allied health, culinary, and more. The sites featured their own editorial content, built from information in the public domain, as well as other information that the schools would provide to the company. Non-profit schools paid a small subscription fee to have prospective student inquiries routed to their admissions office. For-profit schools paid a fee for each lead.

My first assignment involved some basic inbound product management work. I gathered requirements from the editorial team servicing the schools and worked with engineering to match those requirements to what the platform could actually deliver.

An implicit promotion

Looking back, the CEO probably had a larger role in mind for me from early on. He kept handing me more to do, a little at a time, before he ever made anything official. It was just pretty natural, and the culture at All Star was already so open that taking on more never felt like any sort of leap. People started treating me as the head of the product organization before I remember there being any formal organizational change. I credit the team as a whole for this very organic collaboration.

Eventually it became explicit. I moved into an interim executive role responsible for the product organization. The business had three pillars. Sales recruited schools to pay for lead flow. Marketing generated the traffic of prospective students to the web properties. Product focused on the conversion of the student’s visit into a lead for the schools.

During the time I was there, the product team grew from eight people to more than thirty. The systems the product team served multiple audiences. For marketing, the systems provided the data needed to optimize paid and organic traffic. For sales, the systems delivered the leads and the reporting that the schools wanted. For the students, the sites matched them with the schools and content that actually fit them.

What actually made the difference

The real differentiator wasn’t something I invented. It was a discipline the team already had before I got there. The company was committed to delivering the highest quality leads to schools, not the highest volume, and none of it was ever gimmicky.

The aim was simply to provide high quality content and merchandising to serve students well and to encourage them to spend real time in the directory. With the high quality leads, the assertion was that schools would value All Star leads higher than their other sources. Achieving these goals most effectively, often had to translate into new product requirements, tough decisions to refactor or rebuild code, and ultimately to hire people.

The CEO

I really enjoyed working for the All Star founding CEO. He had already had success running MSN.com for Microsoft. He had also bounced a couple of times with less successful endeavors after leaving Microsoft. All Star was his next venture, this time built the way he wanted to build it after a number of hard lessons. He wasn’t interested in working people to the ground. He wanted to build something that would last. And he gave me real latitude to run different experiments, which kept the work interesting for both of us.

The ending

Private equity approached him, and it forced him to think through what was best for him and the company. He recruited a new CEO, a very nice guy, to run the company under the new owners. I probably would have liked staying, except the role would have meant reporting into private equity instead of into him, and I didn’t want that.

He didn’t just announce the sale and leave it there. He met with the whole management team together at an offsite at his own house, built around bringing everyone along and setting up a clean handoff to the new owners going forward.

My own role within the company at the same time was winding down the way we designed an interim function. We hired and promoted people into the functions I had been covering, and by the time the actual handoff happened, I was already working on special projects. Part of why I stayed involved as long as I did was simply that I really enjoyed working with the CEO.

Barracuda calls again

Around the same time, Barracuda’s founding CEO got back in touch with me. To his credit, he had been staying in touch on and off for a couple of years. Each time he listened carefully, understanding that I was still a bit burned out with Silicon Valley and not really looking to go back yet.

When the founding CEO of All Star Directories told me he was selling the company, Barracuda’s founding CEO called again. This time, with Marsha’s very strong encouragement, I actually heard him out.

The drive down

I signed Barracuda’s offer in November 2005 and closed out Hillwork, my consulting company, at the end of the year. In January 2006 I put my 1994 BMW 325i on the road and drove it down to California to start the job, leaving my family up in Seattle to close out the school year. This time the family looked different from the one that had left Silicon Valley years earlier. The girls were older, with our older daughter heading into third grade and our younger daughter into first. They weren’t toddlers anymore. Marsha and I had more behind us than we did back then, too. I didn’t know it yet, but I had just started ten years back in Silicon Valley.

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In last Sunday’s post Seven Months Off, I wrote about the almost Taoist-flow I experienced, with no plan and that almost being the point. I would think of a friend, and the friend would call. I would think I needed to try something new, and an opportunity would appear. It has never happened to me in quite the same way since. This month, I experienced a flow that ran in completely the opposite direction.

A weird Labor Day

I’m not sure who came up with the saying that “bad luck comes in threes.” Labor Day was one of those, with each little piece of bad luck being pretty small. That day, I had a scheduled brunch with a friend. Right as our food arrived, his phone rang with a call from his daughter’s care provider reporting a dead car battery on their outing to a local museum. He had to leave early to pick them up. On my way home, our neighbor cancelled the dinner and movie we had planned. He had just learned his brother was in the ICU back in Xinjiang and needed to be available for his brother. After returning home, we heard from my cousin that her husband had come down with COVID. This is the same couple we were supposed to meet in Europe for our vacation the following week.

Of course, nothing about the day was serious. My friend and I still got to catch up over food for an abbreviated time. Marsha and I still had a nice dinner in the neighborhood (Farmhouse Kitchen!), and we enjoyed the movie (The Odyssey) on our own. And my cousin still had a good five days to recover. (He eventually tested negative on the day everyone would have to get on a plane to Europe.)

Two days later

The Wednesday after Labor Day, we flew out to Columbia, South Carolina to see our older daughter. I’d never been there before, so I was eager to visit her new home and workplace. Somewhere between checking our bags and landing in Columbia, I lost my passport card. I remember having it in my pocket after showing it to the gate agent at the bag check, and I did not have it when I landed. United searched the plane in Columbia, I called the Chicago Police at O’Hare in case I lost it during the trek from Terminal 1 to Terminal 2. United’s lost and found also followed up via email. Nobody found it.

In the middle of all that, while filing the lost and found report on my phone, I tugged on my iPhone cross-body strap too hard and broke the strap free from the case. Again, this wasn’t that serious either. The good news is that I still had my Oregon Driver License as a travel ID to get home, I still had my passport book at home ready for our planned European trip the following week, and the iPhone case is still good protection for the phone body itself even if it no longer works with the cool cross-body strap.

A fun visit to South Carolina

The visit itself was a good one. I think our daughter has a really cool office, a nice unit in a duplex, a great duplex neighbor, and a growing community of friends. And interestingly enough, her community started with a former Yale classmate who is from Columbia, South Carolina and whose parents have returned to the area. We also took a day trip to Charleston on Friday, browsing the shops along King Street and the Market, walking through Waterfront Park, and making it out to Mt. Pleasant as well.

I didn’t expect to like the food so much. I am a huge fan of the pulled pork with a mustard barbecue sauce and the hash over rice (War Mouth). It was also fun to try the sausage gravy and biscuit (Church and Union), as well as the fried green tomatoes, collard greens and fried fish (Saltwater Cowboys) in Charleston. The place even had good versions of the stuff we like at home, like good coffee (Godspeed, Azalea, Knowledge Perk), high-end cocktails (Bourbon, The Hollow), craft beer taprooms (Craft & Draft), and even a cool street market (Soda City). Even her local neighborhood Lebanese place (Arabesque) was quite good!

Our daughter has also picked up disc golf since moving to Columbia, and we went out with her to play a round at Finlay Park. It’s a beginner course, and we needed just the middle range and putter discs. I’m not sure if we would have been ready for a driver!

We saw our first football game down South, too. Many women showed up in decorated cowboy boots and dresses. The fanfare is quite a sight, and we got to wave white rally rags in a stadium chant called the “Sandstorm.” South Carolina has a huge band with many tubas, and three sideline squads of cheer athletes. Marsha, who marched in the University of Washington band, was impressed by the whole scene!

Unfortunately, right before halftime, a rain and lightning storm came in fast and soaked everyone both at the game, and while waiting during the mayhem at the shuttle stop to get us back into town. I stayed mostly dry myself, since I had packed a rain poncho from Marsha’s stash, a leftover from one of our younger daughter’s Carnegie Mellon events of all things. And I happened to be wearing shoes that can survive a washing machine while Marsha and our older daughter were not so fortunate. Still, the game itself was delayed by 74 minutes because of the storm.

Interrupted travel plans

At the time we left for South Carolina, we still had the official plans to go to Europe the next day after that trip. Of course, prior to leaving South Carolina, Marsha had already expressed a preference to cancel the trip, first when learning my cousin’s husband got COVID. However, because the booking.com cancellation policy for our hotel in Germany had us owing 90% of the room after September 1^st, we decided to wait to see how he was doing. Then, when he was still testing positive on the day that our Switzerland hotel payment was due, Marsha expressed a preference to cancel again. Still, we ended up paying the Switzerland hotel fee, and proceeded with the trip. In retrospect, I’m not sure why I advocated trying to continue the trip. The whole point of the trip was to go with them. Going anyway just to honor the cancellation policy was a little bit like the tail wagging the dog.

What finally changed my mind was a rare mishap at Columbia (CAE) airport, forcing us to miss our Icelandair flight out of Portland the following day. Our Bombardier CRJ550 had a mechanical issue on the ground in Columbia, initially forcing a delay in our outbound flight to Chicago. Of course, this delay would cause a missed connection on the last flight from Chicago to Portland for the night. The United agent graciously booked us the first flight from Chicago back to Portland the following morning, getting us back into Portland in time to return home, pick up our passports, repack our suitcases, and catch our flight out. Courtesy of United, we even had a hotel booked in Chicago for that connection. Then, our flight to Chicago that night got cancelled too, so we never made it out of Columbia. I had to cancel the Chicago hotel, get United to send me a new booking link, and book us into a hotel in Columbia instead. We ended up getting into Portland closer to 4:30pm the next day, missing our Icelandair flight at 3:30pm. So what finally changed my mind was that Icelandair flies out of Portland only every other day, and we would have missed two days of the trip and likely paid a lot more to rebook. On top of that, I still had the background worry about the lost passport form.

Marsha believed intuitively that something kept getting in the way of this trip for a reason. I was mostly pushing to go. However, it was only after a stack of small, ordinary problems that even I did not want to push through anymore.

I’m not quite sure I ever had this kind of experience before retirement, and I have been pondering what changed. Looking back, I do not think retirement gave us permission to cancel so much as it gave us permission to say yes to three separate trips inside the same three weeks in the first place. We had been planning the visit to our daughter’s new place, the Europe trip with my cousin and her husband, and my trip to Bend with old friends from my Latitude days for quite some time. They just all happened to land in the same short window. The tight scheduling was not the result of having a limited window of vacation days we needed to protect. My view is that we had the flexibility to work well within other people’s schedules, and I think this is a good problem to have.

So that first day back, we stayed home instead, still in our pajamas at midday, with a plan to make Mabo Tofu out of a spice packet, tofu that Marsha had fortuitously purchased before leaving, and ground beef we had in the freezer. The aim was to allow us both to not have to leave the condo. I had queued up posts here on Substack in advance so I would not have to write anything for three weeks on the road. The road trip was gone, and I was writing anyway, back to life as usual. We talked about taking a photo of the scene for this post, and then decided we looked too much like two people who had spent the entire day in pajamas to put it on the internet.

A few months ago I wrote here about building a small gratitude journal app so that we could all use it freely without being constantly upsold (“enshittification”). We have actually kept using it, and it memorialized our feelings at the time. Right before any of the flights fell apart, Marsha wrote an entry from Columbia that ended with hoping for a smooth flight home and on to Zurich the next day. That flight never happened. Once we got home, my cousin texted asking when we would finally make it to Switzerland. That text gave me a better way to think about all of this. The trip wasn’t necessarily one that went up in flames, but it could be one we are still going to take.

So, this time the flow did not bring us friends calling or opportunities showing up on their own. It brought us a string of small interruptions instead. It also brought us something neither of us expected, a quiet day at home we enjoyed more than we thought we would. And we still have the possibility of a trip that might be waiting just a little further down the road.

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Editor’s Note: This is the third of four posts describing my time in Seattle after leaving Silicon Valley the first time. If you missed the previous two, I suggest you start with the first one describing my time at Asta Networks, followed by a stint at AskMe.

Time to myself

Of course, during this period from June 2004 to January 2005, I remained concerned with the same question, which is what I want to be when I grow up. This period didn’t provide a complete answer, but it brought me closer to it.

I left Silicon Valley wanting a change. Three years and two startups later, I didn’t have an answer, and I now had a diabetes diagnosis that made it even more clear that my life needed to change. I last left this story on the note that I resigned from my role at AskMe. I didn’t have a plan for what would come next, and the decision to just stop working altogether didn’t come easily.

Marsha made the subsequent journey possible. She stated explicitly that she didn’t want me to spend my time off work by assuming the role of “Mr. Mom.” She supported taking real time for myself and not just trading a job outside the home for a job inside the home.

Of course, anyone who has taken time off from work at age 37 knows that doing so isn’t all fun and games because there aren’t any playmates. In my case, Marsha had our kids to look after and, other than the one month we took off in the summer for a driving vacation, wasn’t really available to keep me company. My other Seattle area friends were all still working full time.

At the same time, I couldn’t just immerse myself in long runs and bike rides. I wrote earlier about how I’d become a marathon runner after returning to Seattle, and I’d even done some good distance cycling having done a 1-day STP (Seattle to Portland) bike ride, a double century, and all of its associated training rides just a couple years earlier. Unfortunately, with my doctors unsure of either the cause or the treatment for my somewhat unusual case of diabetes, they were worried about the risks involved with endurance athletics for me. So that door for even more running and cycling closed just as I finally had the open time to do it! Basically, when I wasn’t volunteering for a nonprofit, or seeing friends occasionally on weekends, I spent most of my time alone.

Books and their impact on me

I read a lot, including books on spirituality, life stages, and natural health. I think that throughout this period, I was in sort of a Taoist flow. I would think of a friend, and the friend would call me. I would think I need to try something and someone or some opportunity would appear. Candidly, that hasn’t happened to me in any other period in my life.

For example, when I thought I should perhaps do some non-profit work, a contract recruiter I had met through my time at AskMe called me with an idea and to introduce me to a non-profit she was involved with. I’ll leave the organization unnamed, but its founder had written a bestselling series of spiritual books that I genuinely liked. Some of what I was reading really resonated with me. I did stay involved for a while before deciding I didn’t want to invest my time that way long-term, and the bigger issue for me was less about the individuals or the cause itself. I had just gotten used to a set of work patterns during my time in Silicon Valley and realized I wasn’t trained to work in more of a volunteer setting.

I also got my first experience with life coaching. I partnered with this same recruiter on conducting my first ever life coaching workshop. We put up handmade signs on telephone poles around town, and ran the workshop out of the store of one of her friends. I still find it hard to believe that people actually showed up and paid for it!

I remember thinking that I needed a framework to decide the next phase of life, and a stranger in the waiting room of an environmental medicine doctor (alternative health) recommended a book called Halftime: Moving from Success to Significance by Bob Buford, which was good reading material and the start of my reading other books on this topic. It’s largely written from a faith-based perspective but provided some good frameworks to think about what I was experiencing in a different context. I was also starting to get into works like Carl Jung’s essay “The Stages of Life.”

I also tried to solve the diabetes itself from more than one direction. The “standard of care” in Western medicine at the time was not giving me solutions that worked, so I started reading medical research papers and books. For a time, I thought I had a solution that worked (Dr. Bernstein’s Diabetes Solution), and it, combined with some other lifestyle interventions worked for a while. I also did my first 7-day water fast in that period, too. It turns out none of the lifestyle interventions turned into a permanent fix.

Photo Kiosk Business

During this period, I also decided to go into a little solo business of my own. I started by buying a photo kiosk, with the intent of potentially making passive income by having a network of them once the first one proved successful. The concept is that the kiosks would allow people to print quality photos on the spot from an SD card and other popular memory formats or to back up their SD cards to a CD. The aim over time was to purchase more and ultimately hire someone to replenish the supplies (e.g., paper rolls, ribbon rolls, CDs, and receipt rolls) while I collected passive income.

It actually wasn’t hard to get a machine placed at first. I put my first machine at a Simply Seattle tourism shop at the Pike Place Market which had good foot traffic of snap-happy tourists. I basically did a 10% revenue share with the shop, and early customer feedback was reasonably positive. The owner let me just use the electricity there and share the Wi-Fi. He also gave me prime placement, right across from the cash register.

The problem was that the built-in printer was notoriously finicky and would jam. I couldn’t always get to the machine to repair it in time, and users would ask the store employees for help. The whole thing proved to be too much of a distraction for that Pike Place store, so they asked me to move the machine to their downtown store. That store didn’t provide the foot traffic of the Pike Place Market store, and it wasn’t worth either of our time to keep it there.

To address my personal inconvenience of service calls, I then moved the machine to a store closer to my home at a higher end neighborhood grocery store called Matthew’s of Lakemont. (It’s actually the site of where the Town & Country Market is today). One difference in that location is that the store’s IT department wouldn’t let me share the same Wi-Fi connection as their point-of-sale systems, so I had to get my own DSL line, which ate into my profits. The bigger problem was that in a neighborhood environment, people could easily compare the high cost of my low-volume process with the much lower cost of going to a high-volume provider like Costco to get professional quality photo printing. There was some business, but ultimately, it became clear that the goals of optimizing the kiosk location for being easier to service the units was incompatible with the ability to capture foot traffic of potential users with no other convenient options available.

I ended up taking the kiosk home and using it for my own photos before selling it on eBay to a camera store that used it in-house. The kiosk made much more sense in an environment where store employees were already on-site to take care of the machine. My problem was just that the printer used in the kiosks was just too finicky to make for a good passive income business, and ultimately the manufacturer went out of business because other operators had similar experiences.

Moreover, much like with my volunteer experience, I also learned here that I didn’t enjoy working as a solopreneur. Again, perhaps because I was trained in a Silicon Valley environment, I enjoyed having smart colleagues to collaborate with, people to challenge me and tell me when I’m wrong, and also to celebrate wins with. There wasn’t anyone around to celebrate with when getting my first location signed or getting the first customers and no one else to commiserate with when deciding to shut down the business. I started to see positives in the style of work that I was looking to get away from originally.

The beginnings of Hillwork, LLC

Of course, one artifact of starting this little business was that I had to collect sales taxes and report revenue to the state. With the help of a lawyer friend, I ended up creating an LLC. The LLC structure was a good choice for me because I didn’t want to personally go bankrupt if someone ended up using my photo kiosk for something that might end up in a lawsuit.

I ended up choosing the name Hillwork for my entity. I liked this name because of my days as a marathon runner, and I liked hillwork because it was the one part of training that makes runners stronger. I felt like this term also described the period of life I was in, one that would make me stronger.

Even though Washington state required that I run a name search against other companies in Washington, I didn’t know at the time how to run the search nationwide, so instead I just bought every domain (hillwork.com, hillwork.net, hillwork.org, and hillwork.us) figuring no one else could claim they owned the name if they didn’t have any of the domain names!

What I didn’t realize at the time is why the name kind of sucked. When I showed up to the bank to open my business checking account, the banker thought I was in construction doing grading and excavation. Others have also asked me if I run a landscaping company.

In any case, there is some history behind why I even bothered to do an LLC just to do independent consulting where I could have settled for a sole proprietorship. It’s all because my first business was a photo kiosk business that faced the public, not a consulting company to do work with friends.

The realization

This seven month period was full of “low cost probes” (a term used in Halftime). I haven’t listed them all here for brevity. However, in spending time by myself both reading and doing some introspection, I realized what the themes of movies like The Wizard of Oz are really about.

In that story, Dorothy goes on a long journey with many adventures only to end up back at home. She doesn’t know the journey will lead her there. She just follows the Yellow Brick Road until every step gets her back there. Along the way, every experience she encounters turns out to be something the characters needed to just see. Tin Man always had a heart, Scarecrow always had a brain. Lion always had bravery. They didn’t need the Wizard to give those things to them.

My favorite movie of all time was The Matrix. (I can’t use “What’s your favorite movie?” as a security question any longer because I tell everyone this!) After discussion with a high school friend (the same one who encouraged me to try to get life insurance resulting in my first diabetes diagnosis), I realized The Matrix was something similar. Hanging on the Oracle’s wall was “TEMET NOSCE”, Latin for “Know Thyself”. The main point here was that the whole movie was a series of experiences to get Neo to build up the confidence himself without the Oracle ever giving him the external validation.

So, as I was taking this random walk through the seven months, I realized that perhaps the right thing to do was to start returning to the work world I was more familiar with. Like Dorothy, I didn’t expect each step of the journey to lead me back to the path from where I came from. And like Neo, I didn’t expect that the real journey was going to be knowing myself.

A New Year’s Resolution

In January 2005, after over six months off I decided it was time to return to the working world. I wasn’t sure I was ready to join something full time, but perhaps I could do a part-time consulting gig. I set a New Year’s Resolution to start the process to find something. I didn’t have any idea of what I was going to do.

I mentioned before that I was in a Taoist flow that year. Out of the blue, a contact whom I’d met during the seven month break had reached out to me. He was a consultant in the Seattle area (a former Microsoft product manager, best known for introducing Clippy to Microsoft Office). He told me that he had a friend that was looking for some help, and that he was too busy to take on the work himself.

That referral turned into my first consulting gig and favorite of all time.

In two weeks, I’ll tell the story of that consulting gig and my eventual return to Silicon Valley.

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Earlier today, I let my Microsoft account get hacked. Marsha asked me to warn my Substack readers about what happened with the hope of letting others know that anyone can get fooled.

For context, I spent ten years at Barracuda Networks, with line responsibility for the company’s email security offerings. I didn’t just work near this problem. I was responsible for building the product to stop it. Of course, all that background didn’t save me this morning. It actually made this even worse because I know enough about this whole thing to be truly embarrassed, not just annoyed.

The email

The email came from my mom’s accountant. It’s a small tax office in Texas that has done her taxes since my dad passed away in 2013. The email thread looked real involving correspondences with people in the office I knew and with their real email signatures. The request was for me to review an attached PDF, with a password to open a file. None of this was out of the ordinary for that office.

Of course, the real trick with password-protected files is that the password keeps the file hidden from every scanner sitting between the sender and me. A scanner can’t check what it can’t open. Instead of a file, I got a fake Microsoft prompt with a code followed by a real Microsoft sign-in box instructing me to enter that code.

Something wasn’t right

Unfortunately, I typed the code thinking it would open a file, but there was no file to see. Instead, I was directed to a generic Microsoft status page, and I realized pretty quickly something was off.

So I copied the email source into an AI assistant to check the validity of the email. The good news is that it was legitimately sent by the accounting office. The bad news is that it was pretty clearly a phishing email.

That’s what sent me straight into my Microsoft sign-in logs, and I found a problem.

What actually happened

I didn’t login from Nebraska. I was a victim of device code phishing, and someone had free rein over my Microsoft account for a few minutes. The code belonged to someone else’s request. It works because it looks pretty real. If there’s one thing worth naming, it’s being unexpectedly asked to enter a code. In this case, it was triggered by a link I never intended to visit.

Locking down my account

From the Microsoft console, I used “Sign out everywhere” to kill any active tokens.

Then, I changed my password. I went through my Outlook rules, line by line. I checked Sent Items for anything sent in my name. I looked through the list of apps tied to my account, looking for anything I didn’t recognize. Nothing extra was hiding among them.

I emailed the accountant and the office owner directly, letting them know their accounts had likely been compromised. They emailed me back acknowledging the issue. That felt like the end of it.

One more scare

Then, a couple hours later, I went back into the Microsoft setup I manage for my family. I pulled up the application audit log, just to be sure. I panicked a little bit when I saw an entry with a new service principal added.

I was fearing that there was some planted application on my system and that I’d missed the real damage. I took a bunch of screenshots and loaded them back into my AI assistant, and it assured me that “Microsoft Azure AD Internal - Jit Provisioning” added “Lifecycle Workflows” which was Microsoft doing its own routine housekeeping, totally unrelated to the morning’s attack. While I was relieved, I also couldn’t get rid of the feeling that something else was lingering. That feeling sent me back through everything else I hadn’t checked yet, including my security info, my devices, my safe senders list, and my mail folders. All of it came back clean, too. So, for now, I’m going to let this sit.

What stays with me

The technical stuff isn’t what made me feel bad, as I have more background in all of this stuff than most people ever should. To me, the real problem was how little all of the background helped in real-time. The message came from a real email account. It asked for something completely normal. The sign-in itself was just me typing a code into a window that looked completely real, because it was completely real. Having a security background during my professional career didn’t stop me from falling for the exact thing I spent a decade preventing.

Getting back to the reason Marsha wanted me to post this, it’s really just to show a bit of humility to remind others to remain vigilant. I don’t feel any need to post a list of red flags for everyone to follow. I already had most of those memorized, and it didn’t help me at 10am this morning. I think the bigger thing is just to remember to respond quickly, starting with “Sign out everywhere” and to follow the other steps. Then, let the other hacked parties know about the incident and remind others that these things happen. Brutal.

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AI disclosure: I used AI tools during the drafting and editing process to help clarify structure and language. All ideas, judgments, and final wording are my own.

Editor’s Note: This post is part of a series about leaving Silicon Valley for a short stint in Seattle. It’s part 2 of a series that started with yesterday’s post about my experience with the first startup I joined after moving to Seattle that then led me to join AskMe.

A Warm Intro

After departing from Asta Networks, I was still looking for the change from my life in Silicon Valley. AskMe also proved to be a very different experience, but also not the one I’d really hoped for.

On its surface, this one seemed to be a little closer, actually. Much like how I joined Latitude, I got a warm intro. The engineering head at Asta Networks was one of the angel investors and knew one of the company founders very well. The company was in the midst of its own reset, as it was in the process of winding down its dot-com era consumer presence and pivoting to become an enterprise collaboration vendor. I was somewhat familiar with this space from my time at Latitude.

Overcoming Some Known Challenges

AskMe was also a VC-backed company, originally founded to be a consumer Q&A website. At its consumer peak, it was a PCWorld Top 100 site, with over 10 million registered users and over 5 million knowledge articles in its knowledgebase. At the time, markets weren’t as friendly to companies relying on Internet advertising for revenue, so AskMe saw an opportunity when both Procter & Gamble and CNA Insurance had approached the company to create internal company versions of the software.

Before I joined AskMe, the company let me speak with the existing customers. One of those conversations was with a director at P&G, and he did a good job explaining the cultural value of AskMe inside of P&G, where Ph.D.’s across different business lines appreciated having a platform where they could openly collaborate and share ideas across functions. Because their work was proprietary to P&G, they weren’t able to publish academic papers or attend conferences to share with outsiders, so the platform served as an internal social networking tool, where experts inside of P&G could find each other, pose questions, view conversations with others, and add their own comments. I saw the potential.

Of course, I remained a bit skeptical, knowing the difficulty with enterprise sales, and I knew the return on investment (ROI) would have to be quite “soft.” Unlike Latitude’s platform where costs could be compared against actual telecom costs with old school teleconferencing, justifying AskMe in some way required attempts to quantify the value of making a connection, the value of capturing previously tacit knowledge in a knowledgebase, and even the re-use or spreading of knowledge. I understood the challenges, but I was intrigued.

I joined AskMe as its VP of Marketing through its pivot into an enterprise player. We went on to close several more name-brand enterprise customers, including Boeing, Honeywell, Ford, ABN Amro, and others. The value proposition was “Expertise Location and Management” which was a fancy way of saying that we connected people with similar expertise that didn’t know each other inside of very large enterprises.

We won some real recognition, including an SIIA Codie Award for “Corporate Newcomer of the Year” and the WSA (Washington Software Alliance) “Most Promising New Company.”

Another downsizing

Of course, the issue we ran into was that these very complex customers were, by definition, the most complex organizations to sell into. We were able to utilize affiliations with organizations like APQC to find member companies with enterprise knowledge management initiatives underway. However, once we tapped those lists, we faced the difficulty of trying to sell such a soft value proposition during an economic downturn.

Ultimately, we downsized the company, reorganizing ourselves around a partnership model where every executive was responsible for selling and supporting a set of customers within a vertical. I moved from VP of Marketing to VP of Life Sciences. Eli Lilly and Pfizer were two of my accounts. This move was a slog. Once we made that change, I spent most of my time prospecting a long list of life sciences companies, with very long sales cycles. Our Pfizer relationship came in through AskMe’s consumer vertical, and the Eli Lilly relationship came in through the acquisition of a company with an adjacent product, rather than through anything I closed myself.

Through our downsizing, I took on more than just marketing just like at Asta. In this new model, I led the cancellation of our TriNet contract, the outside firm handling our payroll and benefits. I took over the implementation of insurance, payroll, and benefits in-house with our office manager. I also owned IT and data center operations, so I managed the IT person responsible for our spam problems, our backups, and the daily realities of a small internal data center.

Through that period, I also owned many of the logistics of our eventual office move. The earlier AskMe office was a typical dot-com space, and our lease happened to end right as T-Mobile’s acquisition of VoiceStream freed up their old Class A office space for a cheap sublease. We also were able to use the on-premises switch room as a data center, allowing us to cancel our Internap contract for hosting. We got a serious office upgrade, sharing the same office complex as Expedia at the time, at a bargain rate!

What I learned about being at that company was the power of being “hard core” economically. (This was a term frequently used within the company.) Even though we didn’t sell many new customers in our later years, the company stayed alive by selling professional services to installed base customers. In these large enterprises, AskMe integrated with internal Verity, Autonomy, or even SharePoint applications to help identify who in a company had already written about a particular topic. To integrate with an enterprise’s existing systems, we’d charge $250 per hour, but paying an Indian outsourcing partner about $16 to do the actual work. We were running software margins on a services business.

So, the company was surviving, not thriving.

Unexpected Health Issues

During this period, at age 36, while training for my fifth marathon, I found out I had an unusual case of Type 2 diabetes. The diagnosis itself came as a surprise. A high school friend who had become a financial advisor encouraged me to purchase a life insurance policy. During the application process, a nurse came by my house to draw my blood and take my vitals, commenting that this was just a routine check for someone as fit as I seemed. I was rejected outright, only to find out the reason was a completely asymptomatic case of uncontrolled type 2 diabetes. I was just walking around with an A1C of 11!

This health news simply provided another signal that my move back to Seattle wasn’t really getting me closer to what I wanted out of life. Ultimately, I decided, with the support of the company, to really take some time off from my career.

What AskMe Was For

While AskMe did end up surviving (and got purchased by Realcom of Japan years later), it never really made a lasting impact on the industry. The whole category of Expertise Location and Management ceased to be a category. The closest example of the application that exists today is Quora, which is more similar to the consumer-facing business that AskMe abandoned as I joined. Probably the more relevant example is the business case right now being made with AI, where the intention isn’t to locate the expert but rather to capture the expertise so that an agent can mimic the expert in their absence. While there’s a substantive difference between locating the expert and replacing the expert, the business case still requires a soft-dollar argument.

Like with my situation at Asta Networks, this time at AskMe produced some good lessons and some good friends. However, the net is that those three years did not feel like “winning” at the time.

During my time in Silicon Valley, Oracle was growing fast. Visioneer debuted as #1 on the Ingram Micro Best Seller List and ended up going public after I left. Latitude had enough success to do an IPO. Asta had no successes, and AskMe had a very short-lived run to profitability before essentially stagnating. This stretch of life certainly didn’t feel like an improvement over what I left in Silicon Valley. It was time to try something else.

Next week’s post picks up where this leaves off, with a complete departure from technology startups.

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Editor’s Note: I had originally intended to write a three-part series about my time in Seattle from 2001 through 2005 after leaving Silicon Valley, and I realized while writing the first in the series about my first three years (and two startups, Asta Networks and AskMe), that I really wanted to devote a post to my experience at each startup individually. So, now this is the first of four posts, not three! I’ll publish the second one tomorrow.

I am picking up this story in August 2001, after I had left Silicon Valley but was still transitioning out of Latitude while living in Seattle. My motivation for leaving Silicon Valley was looking for some change. The first job I took in Seattle was indeed a change, but perhaps not in the way I’d envisioned or hoped for.

Spending like a dot-com

While I was still finishing up at Latitude, I happened to meet the CEO of Asta Networks. The company had successfully raised $18 million through its Series A venture funding, founded by four University of Washington professors to defend against DDoS attacks at the time when Code Red and Nimda still made headlines.

Unfortunately, the company had hired over 60 people, including growing sales, support, and operations teams, all well ahead of the product being completed or proving itself a fit with real customers. It had expensive downtown Seattle real estate on the 17^th and 18^th floors of 520 Pike Tower, which was Visio’s old space. The team had already burned through $11M, without any clear evidence that the prospective customers would actually pay for what the company had built so far.

The wind-down

In my first couple of weeks, I made a point to the other executives that we were far from a Series B funding milestone, such as closing the first 20 paying customers. It was going to be up to us to present to the Board a plan to reduce our burn rate to give us the runway we needed to support a follow-on funding round. What I didn’t anticipate was what happened four weeks later (six weeks after I’d started). The Board fired the rest of the management team and most of the employees, leaving me and the then director of engineering to lead a team of 17 remaining people.

As an interesting side note, there were some good people in the group that were let go. A fun fact is that the CFO who lost his job that day went on to become the CFO of Microsoft.

Right after the layoffs, we closed the first two customers ourselves (with very small deals), and we cleared out the rest of a sales pipeline that wasn’t real. From there, I hired a telemarketing company to solicit conversations with enterprise prospects, while we also pitched other vendors in Silicon Valley for potential ISV (independent software vendor) relationships or OEM (original equipment manufacturer) partnerships using our core technology. The hope was one of these activities might eventually lead us to new customers, or better yet, an acquisition. Both efforts got us meetings and good learnings, but no results.

The real problem at Asta was that the company had developed a tool to inform sophisticated network engineers and not a tool to respond to attacks. We learned through our interviews with enterprise customers and vendors that they really wanted a solution for Distributed Denial of Service (DDoS) that was closer to “set and forget.” The technology built by our team was essentially a NetFlow reporting tool, and remediating threats required the network engineers using it to formulate their own strategies to respond to attacks. Competing solutions that ultimately survived in the marketplace featured automated mitigations. (This is a lesson I took with me to Barracuda Networks, years later.)

Concurrent with enterprise and vendor meetings, I also led an effort to further reduce our burn rate beyond the reduced headcount. During that period, I led the cancellation of expensive Akamai and Internap contracts, liquidation of the networking gear in our lab, the auction of our old office furniture, and a clandestine physical move out of our expensive downtown office space. Our board packaged up a bankruptcy because the landlord would not let us out of our lease. With only 17 of us, we moved into some extra space in an office of another local Seattle startup (Vigilos, now closed).

Ultimately, after all the pitching to enterprises and other vendors, our best possibilities to potentially continue our business ended up being with two local Seattle area vendor companies. Those conversations were more like acqui-hire deals, but they didn’t close either.

At that point, it wasn’t worth keeping all 17 of us, so the Board cut us down to 4. At that point, we moved again, this time into Madrona Venture Group’s incubation space. We spent the remaining time there trying to pitch what we could do with the roughly $6 million that was still in the bank. However, what became clear to us at the time was that the Board was more interested in having us quietly weather through the dot-com bust until other companies in their portfolios started showing returns to their limited partners. In many ways, this was a much earlier case of what is referred to today as a “zombie startup,” where venture capital funds and private equity prefer to let startups limp along rather than take the write-down.

For a while, the four of us showed up dutifully to the office, brainstormed new company ideas, and spent a fair number of lunch hours trying (and enjoying!) every barbecue place in Seattle. Over time, we did get tired of not really accomplishing anything, so we planned our departures. The head of engineering ended up going to a Silicon Valley startup. He also referred me to a company that he’d been an angel investor for, AskMe.

Didn’t even learn the guitar

Immediately prior to joining Asta, I bought a Yamaha guitar at Costco and signed up for a beginner class at Bellevue Community College. However, midway through the term, I ended up missing about half the classes because of frequent trips to California to do partnership meetings with vendors. I fell so far behind the class and never picked up the guitar again. After years of usage by my older daughter and then a banishment to our storage closet, I pulled out that guitar and put it in my home office a couple of years ago. I even gave a tuner app a try for a few weeks in 2023, but it didn’t take, and I still haven’t really started practicing again.

If that period was supposed to be part of some positive change in my life, it didn’t feel like one. I just went back to another startup, but one that had no moments of commercial success. Even my guitar lessons didn’t survive this startup.

Seeing the glass half full

Looking back, at least spending time with the team at Asta gave me good exposure to the cybersecurity business. I mentioned above the benefit of learning how big security markets like antivirus and firewalls were “set and forget” and how automated mitigation was so critical for commercial success in this business. Beyond the business lessons, I also made a handful of friends that are still part of my life today. A couple of them even read this Substack!

Tomorrow’s post picks up where this leaves off, with my move to AskMe for my next Seattle startup adventure.

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A friend recently asked me to review a management training program he’s developing. The core idea is a management dojo. New managers would practice difficult conversations, delegation, accountability discussions, and other leadership situations before they must perform them in an actual business situation.

My first reaction was positive. Most first-time managers have never actually practiced management. They were promoted because they were good engineers, product managers, clinicians, or project leaders. Then one day they are expected to manage people. It at first seemed to be a perfectly reasonable assumption that practice would help.

The more I thought about it, though, the more I kept coming back to my own management career. Looking back, most of the coaching that mattered was not about building skills. It was about developing judgment.

More information wasn’t the problem

One thing that struck me is how much easier it has become to learn certain management mechanics. When I started managing people, finding good guidance was harder. Today there are books, podcasts, YouTube videos, and online courses that can explain how to run a one-on-one, deliver feedback, conduct a performance review, or delegate work. With AI, a chatbot can now walk a new manager through scripted, difficult conversations in real time nearly as well as a lot of paid external coaches can. The general mechanics are increasingly available and affordable to anyone willing to spend a few hours learning.

All that said, even general-purpose coaching from an outsider isn’t as specific as the narrow set of lessons the company itself has learned. I made this argument a few months ago in a previous post (“The Point of a Playbook”) about how AI with access to the general Internet can produce something confident and well-argued without ever considering what the company itself has learned. External coaching, whether led by consultants or AI chatbots, faces a similar problem.

If management time and training dollars are limited, where should organizations invest them? My instinct is that they should focus on the things that remain difficult to learn alone and are specific to the business. I believe the focus should be in tackling judgment problems rather than skill problems.

Delegation was rarely about delegation

One example that came to mind was customer engagement. For years I would tell product managers to go talk to customers. It sounded like a simple delegation decision. Assign responsibility, provide some direction, and let them learn. Over time I realized that talking to customers is itself a learned skill. The best customer support professionals do it differently than the best salespeople. The best salespeople do it differently than the best product managers. They ask different questions. They listen for different signals. They know how to separate symptoms from causes. They know how to handle objections without becoming defensive.

Years ago, product management usually meant spending real time in front of customers, at trade shows, on sales calls, and in support escalations. I could usually assume that an experienced product manager had picked up some of those skills through that kind of direct exposure. That assumption became less reliable over time. Many product managers today spend years operating primarily as product owners within agile organizations, which can involve very time-consuming tasks that are internally facing, including “grooming the backlog” in the bug database and coordinating development work. Some have surprisingly little experience with outward-facing activities, such as direct customer conversations.

The challenge was never figuring out how to delegate customer engagement. The challenge was deciding whether this person was ready for that responsibility. That was a judgment call.

Performance issues are often diagnosis issues

I saw something similar with performance management. Most management training focuses on the conversation.

• How do I deliver difficult feedback?

• How do I hold someone accountable?

• How do I conduct a performance discussion?

Those are useful skills, but they were rarely the hardest part of the problem.

I spent much of my career working on initiatives that depended on multiple organizations moving in the same direction. When goals were missed, there was often no obvious explanation. Sometimes another team failed to align. Sometimes priorities shifted. Sometimes management had not removed obstacles. Sometimes the employee was not advocating effectively. Sometimes the employee simply was not performing.

From a distance, all those situations looked remarkably similar. I can think of several cases where product plans drifted for months because organizations could not align around a direction. Eventually I concluded that the product manager closest to the issue needed to create that alignment and wasn’t doing so. In those situations, I ended up making difficult personnel decisions.

I also saw this from the other side, where the problem wasn’t with a specific product but with the business direction itself. I recently wrote about my experience at Latitude Communications (“How My First Three Jobs Wore on Me”), where we could see WebEx going after a different buyer than the one we were selling to. We understood where things were heading. We just didn’t have it in us as a team to walk away from the model we had already built and proven. That gap, between understanding a problem and being able to act on it, is its own story, and it’s a harder one than a generic skills-based coaching program can drill into.

In these cases, the hard part was not conducting any performance discussion. The hard part was figuring out what problems we were looking at.

The coaching I remember most

The best coaching I received followed a similar pattern. Very little of it was tactical. Most of it was about helping me see a situation differently.

One lesson that stuck with me involved competing initiatives. Early in my career, my instinct was often to block projects that threatened something my team was trying to accomplish. I viewed them as obstacles that needed to be removed.

Several experienced leaders taught me a different approach. It is often easier to redirect than to block. Large organizations always contain competing priorities. Trying to stop them outright often creates more resistance than it solves. Finding ways to steer them away from conflict is frequently more effective.

The lesson was not the tactic itself. The lesson was learning when a situation called for redirection instead of confrontation. Once again, that was a judgment problem.

The curriculum was never the product

Prior to reviewing the latest version of my friend’s management training pitch, I told him a second-hand story about the Pro Club in Redmond and its partnership with Microsoft on an employee weight loss program. I had a couple of friends that went through it. To me, the curriculum, which included aerobic, strength, and core training, wasn’t what made it work. Any gym has those curriculum elements. What fascinated me was the accountability structure the partnership created with the attention of the trainers (including having trainers actually design, observe, and evaluate the workouts) and the financial incentives (reimbursements) associated with achieving milestones. The Pro Club understood the mechanics of management that worked with the Microsoft employee base. The curriculum that could be easily replicated across many gyms was the commodity. The value-add was in the judgment and ability to apply company-specific knowledge to differentiate itself.

I think a lot of the leadership coaching business runs on a different skill than the one it’s selling. The most successful coaches are often just the most likeable people and the ones that clients feel understood by. In some sense, this is closer to therapy than it is to business judgment. If clients walk out of sessions feeling better, they might mistake that feeling for having been helped strategically. These aren’t the same thing. Judgment is hard to package and hard to prove. Rapport, on the other hand, sells itself right away.

When I coach executives myself (see “Executive Coaching with a Retiree”), I default to interview-based 360-degree assessments instead of surveys. A survey can provide metrics, but it can’t expose what to do about it. Interviews are slower and more expensive to run, but my experience is that this is where the judgment problems show up. I hear specific stories from people who work closely with the executive, and not just some number on a Likert scale.

What should management training optimize for?

This is where I find myself wrestling with the dojo concept. In martial arts, a dojo can train students on a fixed set of katas until they are reflexive. It can train students on known forms for competition that earn points. Management, in general, doesn’t work that way because there’s no fixed kata to figure out whether a plan drifted because of politics, shifting priorities, or a manager that wasn’t doing their job. The hard part wasn’t executing known moves well but rather recognizing the move a situation calls for.

Even when practice includes live, improvised roleplay rather than a fixed script, the exercise is only as good as the judgment behind whoever built the scenarios and reacts in the room. That judgment usually comes from having lived through the specific situations being practiced. A program built to work across many companies and industries has a harder time embedding that kind of judgment than one built inside a single business, no matter how adaptive the roleplay itself is.

Of course, I think the dojo probably works somewhat for teaching certain skills. New managers might benefit some from practicing feedback conversations, delegation discussions, conflict resolution, and accountability. Repetition can build confidence and competence.

Where the money should actually go

What I am less certain about is whether skills practice like this is the highest-value use of management attention and budget.

Apprenticeship doesn’t need to work the same way for everyone. The mechanics, especially now that AI can teach them cheaply and at scale, can reach every manager. The harder kind of development, close observation from someone experienced, has to be concentrated somewhere. My instinct is that it belongs at the specific moments where a judgment call actually has weight, not spread evenly across a training calendar.

The management lessons that changed my career were rarely about what to say. They were about how to interpret a situation. They were about understanding root causes, recognizing patterns, identifying tradeoffs, and knowing which problem needed to be solved. Those lessons were difficult to learn from books. They were difficult to learn from videos. They usually came from experienced leaders helping me think through messy situations where the answers were not obvious. It was also observing seasoned managers navigating business situations.

That makes me wonder whether the highest-return form of management development looks less like training and more like apprenticeship. In my own style, I liked sitting in the open cubes with my teams so we could have visibility into each other’s work. Of course, this only works at a certain scale. More than one CEO or HR department has eventually banished me back into an office. Still, even at Barracuda, our CEO once moved a new hire executive into my office, and we shared it for months before he was ultimately asked to replace one of my peers. I didn’t think of it at the time as a program at all. Looking back, it wasn’t a dojo. It was something closer to watching the judgment behind a decision happen in real time, which is exactly the part no dojo can teach.

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Note on this post: This piece originated as feedback I put together for a friend. I used AI to help reframe my thoughts objectively, focusing on sharing my perspective without sounding too prescriptive. At his suggestion over beers, I’m posting this to Substack “as-is” with some light edits. While my recent posts have been hand-written, I wanted to preserve the original format of this particular piece.

Longtime readers may remember one of my previous posts “Retirement Portfolio Apologies” from two years ago, where I first wrote about sequence risk and the discipline of maintaining a reserve of cash and bonds to mitigate this risk.

This post is simply revisiting that same topic, this time reflecting the current economic environment.

The five-year rule

Our advisor simply wanted to refresh our memorie about holding onto roughly five years of living expenses in cash or bonds, separate from stock, private equity, and other “risk assets.” The point of allocating this way is to act as a buffer for market volatility.

The problem we’re trying to avoid is selling stocks to cover living expenses in a year that the market drops, say 30%. In that scenario, the loss gets locked-in. The decline in that one period then has a permanent impact because the asset base that could compound back when the market recovers shrunk in the process. As mentioned earlier, finance types call this a “sequence risk,” and they caution that it’s one of the more dangerous threats to a retirement portfolio. It is a timing problem, not a market problem. Forced selling during a downturn misses opportunities to participate in a follow-on market recovery.

A five-year cash and bond buffer can help to avoid this problem. If stocks fall, our strategy would be to just spend from the buffer instead of the stock portfolio, let the equity recover, and refill the buffer later after prices rise again. Rather than trying to predict a downturn, the aim is to simply remain indifferent when one happens.

The good news from our meeting was that we didn’t have to do anything. We came in about 1.7% overweight in risk-controlled assets relative to the target, which is close enough to just leave everything alone. We didn’t have to reallocate our portfolio, and this was just a sanity check. The more interesting discussion was related to why the advisor teams are doing this set of reminders with their clients like us right now.

The AI capex question

The finance community has been paying attention to the rapidly growing amount of capital currently being poured into AI infrastructure. For example, Apollo Global Management published a graph showing the high levels of AI investment as a share of GDP compared with the telecom buildout in the dot-com era.

Of course, there is a real bull case for this buildout. The hyperscalers are generating revenue. Amazon is reporting triple digit growth in its AI business. Microsoft reported 123% growth in its AI business. Google’s cloud business is up 82%.

From an end customer perspective, there are also interesting data points. AI Business Weekly summarizes them, including quotations from Nvidia’s State of AI Survey, citing that 86% of enterprises plan to raise AI budgets in 2026. On average, AI now represents 18% of total IT budget, and that number is 25-30% in tech forward industries, such as finance and SaaS.

The honest tension among those watching this industry is that infrastructure spend and enterprise return-on-investment (ROI) are both trending upwards. The problem is that no one is claiming that the two are moving in step with each other. Today, the spend is ahead of the ROI. Even Amazon and Alphabet (Google’s parent) reported negative free cash flow in the latest quarter.

Of course, having spent an entire career in venture-backed startups, I’m personally familiar with forward-looking investment. The problem isn’t necessarily spending ahead of demand. The real question is always about timing and the speed of market adoption. Companies have to be careful to align cash burn with growth.

The financing problem

Oracle has been in the news because observers have been questioning this alignment of cash burn and growth. Oracle has been using debt to fund its AI capital expenditures. Its long term debt is now at $122.3 billion, and the company is looking to raise another $40 billion through additional debt and equity in fiscal 2027. About half of Oracle’s $638 billion in RPO (remaining performance obligations), comes from a single customer, OpenAI. If OpenAI ever struggled to pay its bills or elected to terminate early, Oracle would be stuck holding data center commitments it couldn’t easily exit. That’s not just a hypothetical anymore. The Wall Street Journal reported that OpenAI’s operating loss widened to $12.3 billion in the second quarter of 2026, up from $9.3 billion in the first, even as revenue grew to $6.7 billion. OpenAI’s losses are growing faster than revenue, at the same time as the revenue of OpenAI’s rival Anthropic, doubled to $11.6 billion and generated a small profit over the same period. S&P has downgraded Oracle’s credit ratings, and Moody’s has put a negative outlook on the company. All of this has caused Oracle’s stock prices to fall (down over 50% from its peak in September 2025), and its stock is sitting inside nearly every broad index fund, including ones we own (e.g., CUSUX, CMEUX, FXIAX, SPY, JTEK).

At a personal level, I see how Larry Ellison is likely just making yet another bold industry bet. At a much lower level, I had a personal experience with this when I worked at Oracle at the beginning of my career, from 1990-1993. In my group, our designs for Oracle Data Browser looked beautiful on the large monitors of a Sun workstation (1152x900) but were admittedly hard to use once we ported the product down to Windows 3.1 with its small VGA (640x480) or SVGA (800x600) monitor sizes. I vividly remember during one of our product reviews, Larry Ellison reassuring our team not to worry about it, as he firmly predicted that everyone would soon be using large monitors on Windows desktops, anyway. Directionally, he was right, but his prediction was a few years too early, as most customers ultimately waited to switch to 1024x768 monitors until they upgraded to Windows 95. This was a timing issue. His bet on AI could simply be another case of his making a call ahead of the market.

Beyond Oracle’s on-balance-sheet debt, Microsoft and Meta have chosen to finance their own AI infrastructure by leaning on off-balance-sheet SPVs (special purpose vehicles). These are joint ventures that carry the debt for the data centers while the parent company signs a long-term lease. A Wall Street Journal analysis reported on nine major tech companies that are now carrying about $3 trillion in these off-balance-sheet AI commitments. This figure triples what they report in disclosed leases and long-term debt combined, and it is growing far faster than their reported capex.

For example, Meta’s Hyperion data center in Louisiana is a campus the size of about 1,700 football fields, and the $27 billion in debt financing its construction does not appear on Meta’s balance sheet. A joint venture majority-owned by funds from Blue Owl Capital actually owns the campus, and a holding company raised the construction financing through a separate bond sale. Meta signed on as a minority partner and tenant, agreeing to an initial four-year lease with options to extend up to 20 years, and guaranteed it would make bondholders whole if it doesn’t stay the full term. Since Meta doesn’t consider that guarantee probable, none of it shows up as a liability on its books.

It’s not necessarily that off-balance sheet debt is safer overall. It just appears in the market in different ways.

Data center SPVs like this one involving Meta are funded using a blend of debt and private equity. If a data center customer can’t pay its lease and contracts are renegotiated, the parent company’s stock isn’t directly hit thanks to non-recourse SPV structuring. Instead, the loss hits equity investors first since private equity sits at the bottom of the capital stack, below the lenders. So, we’re directly exposed ourselves because we invest in data center private equity through KKR Infrastructure. We also invest in private lending funds, but none of the ones we’re invested in focus on lending to data center SPVs.

Also of note is Nvidia’s investment or funding arrangements with AI labs and cloud providers which use those funds to purchase Nvidia GPUs. The magnitude is large, with Nvidia reportedly allocating $750 billion to these arrangements. Some refer to this as “circular financing” which can artificially inflate reported revenue and mask true market demand. Some of this is par for the course. At Latitude, we did a version of it ourselves, arranging product swaps with a few vendors where each side bought the other’s offering instead of trading outright, so both teams could book it as top-line revenue. I’ll leave the names out, since some of those companies are still around. However, the sheer magnitude of the Nvidia allocations are making the financial communities take notice.

The difference from past infrastructure buildouts

Financial analysts often compare the AI data center buildout to the dot-com fiber buildout, which all worked out fine in the end. The dark fiber laid in the late 1990s sat mostly unused for years after the dot-com crash. A decade later, when streaming and cloud computing emerged, the fiber remained state-of-the-art and was there to fuel the next round of growth.

A very big risk factor is the depreciation schedule of AI silicon bounded both by physical degradation and economic obsolescence. The hyperscalers have historically used 5-6 year depreciation schedules for server hardware components. Given that Nvidia releases new chips every 12-18 months, what if the useful life turns out to be 3 years or less?

The rental market offers some indication of the shortened lifecycles for AI silicon. Observed market rates for renting Nvidia H100 GPU capacity fell from around $8/hour in 2024 to under $3 by late 2025.

The net is that AI silicon can’t sit unused for years without becoming obsolete. If the demand doesn’t show up in time for companies to service their debt with revenues, the assets just can’t sit patiently waiting for the next growth cycle. The hardware gets old, and the loans need to be paid.

So, this is where we get a timing problem. Over the long term, most analysts believe in the potential of AI. Microsoft, Meta, Amazon, and Alphabet (Google’s parent) will also likely come through fine either way, since each already runs a hugely profitable core business that can fund their AI bets, even if those bets can’t pay for themselves in the short term.

However, Oracle, OpenAI, and the smaller companies have much less of that cushion. And the question remains as to whether the impact will stay contained to these players, their lenders, and their investors, or if it spreads into the broader market. Will there need to be a market correction in the short term?

Personally, I’m not making any sort of market-timing call. Our financial advisor simply reinforced that it seems like a good time to validate that our own financial footing does not depend on being right about any of it. The five-year buffer is NOT a bet against AI. It’s insurance against the need to be a good forecaster in order to remain financially secure.

Staying invested anyway

None of this discussion changes the other side of the plan, which is to keep the rest of the portfolio invested in “risk assets” (public stocks, private equity, high yield debt, REITs, commodities, hedge funds, etc.). The uncertainty isn’t a reason by itself to go to cash more broadly. The cash buffer is what makes staying invested possible.

We’ve lived through a number of downturns, including the dot-com crisis, the Global Financial Crisis (GFC), and the 2020 pandemic. In all of these cases, we saw that the people who came out worse were those who sold somewhere near the bottom and got back in too late. It just turns out a large share of the market’s best days happened in exactly the moments when nervous investors might be sitting in cash.

At the same time, it’s worth being honest with ourselves here. During the dot-com crash and the GFC, I was still working, so we never actually had to withdraw from a shrinking portfolio to live on. During the 2020 dip, I was retired but the downturn was fortunately too short to test anything.

The next downturn might be the first test of this plan to utilize the buffer. The aim is to hopefully avoid selling at the bottom just to pay our condo dues and property taxes! (Brutal!)

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I had my first stent placed on last Friday (August 14). I am grateful to all of whom reached out with support and to check in on how I’m doing. I figured it would be appropriate in this Substack to describe the experience, both to let everyone know I’m fine, as well as to help give a sense of what to expect to others who might go through this themselves or with a loved one!

Part of a bigger plan

This stent placement is not a new development, but rather the next chapter of my kidney transplant story (see “The Detour” and the quick follow-up for July 4th). For those who haven’t been following along, I had a coronary angiogram done as part of the kidney transplant qualification process. That angiogram found five blocked locations across three arteries, including a major one that is typically associated with the “widow maker.” (For those who like the technical terms, my LAD was 80% blocked.) The two other arteries were blocked at 90% and 99%. Multi-vessel disease like this technically made me a candidate for open heart surgery, but the multidisciplinary transplant team concluded that the best way to extend my life was to avoid the delay associated with recovery from open heart surgery. The final decision was to do multiple stent placements (“staged PCI”) for two of the arteries, and medication for the rest. So the procedure last Friday was just part of the plan. Admittedly, all of this heart disease treatment has been somewhat surprising to me, as I have been otherwise asymptomatic this whole time.

I’m scheduled for the second stent October 5th. It can happen sooner, but I had previously scheduled travel from September 9 through September 28, so I opted to delay it. This decision will stretch out how long I need to stay on a daily dose of Plavix (a blood thinner), but I’d rather use the time for my kidneys to recover from the exposure to contrast dye used for the stent placement, as well as to enjoy the time with friends and family.

The day of the procedure

I had the stent placement done at OHSU, as part of the multidisciplinary care I’m getting for the kidney transplant. I also utilize OHSU for nephrology, endocrinology, sleep medicine, and ophthalmology. I’ve been genuinely happy with the care I’ve gotten there.

5am - I set my alarm for 5am, so I could shower and get ready. Probably the most important thing to do was to keep taking my normal medicines. I was allowed a small sip of water for the pills, but I skipped the water anyway. I was instructed to fast from midnight on, and I hadn’t had anything to eat since 6pm the previous day. Marsha had to drive me to and from the hospital, so she was up right with me!

6:15am - I arrived at the procedural care unit, where they started my IV fluids to protect my kidneys from the contrast dye used during the procedure.

8:30am - I was wheeled into the “cath lab.” My nurse played a Depeche Mode Spotify playlist at my request, and we talked while he prepped me. He told me everyone on the team there was from outside the area, that he was from Cleveland, and that he loves living in Oregon for the mountain biking. Before the procedure itself, they called a “timeout”, where I had to state my name, my birthday, and what I was there for. Then they gave me sedatives, including fentanyl, and I don’t remember much else until the procedure was over.

10am - I was back in the recovery room. The official OHSU policy is one visitor at a time, but my nurse let both Marsha and a close friend of mine, a retired doctor, stay with me. Having a friend with medical training in the room really eased any anxiety I had through the process and that peace of mind was very valuable. He could ask questions and hold onto answers from the nurse, the pharmacist, and the cardiologist while I was still coming out of sedation.

While recovering, I got to order a meal. I had the option of breakfast (until 10:30am) or lunch. I asked the nurse what most people preferred, and she guided me to breakfast. I had a fruit cup, oatmeal, English muffin, cream cheese, Greek yogurt, breakfast potatoes, and 2 eggs. There was a 7-item maximum, and I took advantage of it all! They ended up rejecting my request for huevos rancheros because of the overall sodium load across everything I ordered!

1pm - After recovery, I stopped at the OHSU pharmacy for three months of Plavix, even though I’ll need at least six months total. They told me I can transfer the prescription to Amazon (who I normally use) or just stop by there again in 3 months. For others who go through this, know that in addition to needing to take Plavix afterwards, there was also the requirement for me to take a “loading dose” of Plavix (300mg, 4 x 75mg pills) on the night before the procedure, and 75 mg (1 pill) the morning of the procedure itself. I’ll need to stay on this blood thinner for six months after the last stent placement before a kidney transplant.

2pm - I got home safely and spent most of Friday afternoon resting, drifting in and out of naps in front of YouTube. Meanwhile, Marsha went out for provisions in preparation for the next few days.

6pm - My incision site oozed a little after I got home, so I called the after-hours line at OHSU. The on-call cardiologist called back and told me that was normal, explained what to watch for, and said I could call again or come in if I was concerned.

7pm on - We had some excellent salmon that Marsha’scousin caught, smoked, and vacuum sealed for us. I meant to watch more YouTube afterward, but I was out on the couch for the rest of the night instead.

Going forward

The next day, I was still operating a bit more slowly but I have been getting better by the day.

I spoke with the OHSU cardiology nurse via phone on Thursday, and he cleared me for travel. We’re leaving September 9 for South Carolina to see my older daughter, and then on September 14 for Europe. For the ten days in Europe, I’ve purchased international travel insurance that covers both emergency medical and medical evacuation. With BlueCross BlueShield Global Solutions, it’s about $100 for Marsha and me combined, including the coverage for pre-existing conditions. After the Europe trip, I’m also scheduled to go on a guys’ trip September 25 (with the same guys I went to Sedona with last year), where I’ll have to be very careful not to fall while hiking or mountain biking because of the blood thinners!

When I return, I go in for the second stent. After that, I’ll have a referral for a 12-week cardiology rehabilitation program, six months on Plavix, and then I should be ready to schedule the kidney transplant.

The takeaways

For anyone facing something like this themselves, or with someone they love, here’s what I’d want them to know.

• The procedure itself is straightforward.

• The OHSU staff were extremely well rehearsed, as it seems they are doing this all the time. The cardiology fellow who did my orientation was almost like a hospitality host. “Thanks for joining us,” she said. “We appreciate you coming in so early to be with us.”

• The real surprise for me was how tired I felt once I got home. I’d had Sunday’s Substack post pre-written just in case, but I thought, perhaps naively, that I’d feel more up and at ‘em, since the angiogram itself hadn’t been bad. It turned out to be a similar procedure with a very different level of fatigue afterward.

Gratitude

Thank you to everyone who reached out this week. I have a special amount of gratitude for Marsha, who has been there through every step of the way and continues to be. Also, special thanks to my retired doctor friend who has been advising me throughout all my medical test results and who stayed with me and Marsha during my recovery! I also must recognize Marsha’s cousin who gave us that yummy salmon caught in Roche Harbor!

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By early 2001, all of my first three jobs after graduating had added up to the same feeling. I didn’t feel like I was succeeding at anything.

A holiday visit

As Latitude was unraveling, I was working long hours and traveling frequently for work, which meant I wasn’t spending much time with family. During a holiday visit to Marsha’s family in Bellevue (a suburb of Seattle), I watched my father-in-law riding down the hill in front of their house in a wagon with my older daughter, and something just struck me. I didn’t immediately piece together how everything would unfold, but intuitively, I saw a glimmer of a potential improvement to our family life.

Up until then, my whole adult life had run really according to a pretty standard playbook. Go to a good college, get a master’s degree, and then take a job at a reputable company. From there, join a startup to get experience, and maybe take one of them public.

By early 2001, I’d been executing against that playbook. Latitude had gone public two years earlier, and I was an officer of the company. I still didn’t feel like I was succeeding at anything, and I didn’t have an idea of what the next plays would look like beyond that.

My own father had worked long hours and traveled constantly too, not so different from how I’d been living myself. Neither of us was ever really absent. We just weren’t reliably home for dinner, or for the smaller, ordinary moments that make for closer family relationships. That was the world I knew.

So watching my father-in-law with my older daughter didn’t necessarily help me rewrite a whole plan, but it did spark an intuition, not fully formed yet, that being closer to Marsha’s family in Seattle could actually make a difference. We decided to move.

Getting ready to go

Once we made the decision, Marsha ran with all the logistics, the same way she ran most of the household by then. We joked that if I were the CEO or CFO of our family, Marsha was the COO, though operations was by far the biggest job with two small kids in the house. The division of labor was probably never fair, and it probably isn’t even today. This is just the rhythm we settled into.

Beyond the child rearing duties, Marsha handled all the little construction issues with the builder of the brand new home we bought in 1998, as well as project management for the landscaping and deck we’d built out back. She handled all of our travel planning, too.

So, when the move itself came up, Marsha took it on the same way, without either of us really discussing who would do what. She got our house on the market, handled the move, and flew up to Seattle with the kids to scope out our top housing choices. I just flew up later to weigh in on the final decision.

A company shaped exit

When I told the Latitude CEO that I wanted to move, he also took it in stride. Instead of treating it like a resignation, he immediately moved into solutions mode. He acted as if I was just going to keep doing my job from the Seattle area instead of Silicon Valley and had our office manager find a cool office space in Bellevue to work out of.

There’s actually a detail here that wasn’t public knowledge at the time. Leaving Silicon Valley was my choice, but how I actually left Latitude wasn’t. The company was recruiting a VP of Sales at the time, and as a public company, they didn’t want to be seen publicly hiring both a VP of Sales and my replacement for VP of Marketing at the same time, particularly when the stock was already in the toilet.

In March 2001, when we moved to Newcastle (just six miles from Marsha’s family home in Bellevue), I kept running the Marketing group under a title that was really just cover. We changed my title to VP of Corporate Development, with the stated purpose of strengthening our relationship with Microsoft. I think at least some people might have believed this because some of the most valuable work I was recognized for in the company was developing partnerships with Microsoft, Lotus, and Cisco. These relationships probably mattered more to where the stock traded than what I did functionally inside of Marketing and Product Management itself.

In the end, I stayed at Latitude until August 2001 when they found my actual replacement.

Split in two

Writing this in reflection twenty five years later, in a post-pandemic era, “remote” really understates what those five months from March to August of 2001 actually looked like. While my home was in the Seattle area, I was down in California pretty frequently, sitting in the same face-to-face meetings I would have been in if we’d never moved at all. The whole stretch felt like a countdown to me. It really was less a start of a new life and more of a wait for the old one to actually end.

On the days I did work from the Bellevue office, it felt like home. I shared a suite with Latitude’s application engineer for Microsoft as an enterprise customer. She fed my caffeine habit every morning, dropping a venti iced mocha from the Starbuck’s downstairs on my desk while I was already on my morning conference calls. I started leaving a five dollar bill out for her to pick up when she got in. It became its own small ritual, when I did get to be in town.

On the other days, there wasn’t a Seattle life to speak of. I was living out of hotels, splitting time between the Santa Clara and San Francisco offices, with the occasional business trip layered on top.

Somewhere in the middle of that countdown, I picked running back up. Shortly after the wind-down actually ended that August, I ran my first three marathons, Portland, Silicon Valley, and Seattle, three in three months. Today, they call that a “marathon maniac!”

The financial disappointment

Money tells a different story depending on which of the three companies I’m talking about.

At Oracle, I was in the employee stock purchase plan the whole time, buying discounted stock through payroll deduction and selling it off as I went. The stock went up about 10X from its low in October 1990 to when I left in October 1993, and I actually got to enjoy those short-term cash infusions at the time instead of just watching a number move on paper.

Visioneer went public after I got laid off, while I was already at Latitude years. I’d exercised my options on the way out the door, and separately I had put money in as a Series B investor during that funding round. Both of those moves worked out. Ultimately, the company sold its hardware division to Primax (for which I got cash) and reorganized its software assets by merging with Xerox’s OCR division, converting my Visioneer shares into ScanSoft shares, which also did OK.

Latitude was different, and it’s the one that actually mattered to me the most. I never sold much of that stock along the way. I cashed out my very first grant, back when I was hired as a product manager, to pay for the landscaping on the first house we had purchased in 1998. Almost everything I was awarded after that through promotions, I just held onto. By the time the stock hit a dollar, most of those later stock option grants were. “under water.” In other words, they cost more to exercise than they were worth in the public market.

The only options that still had any value when I left were from a leadership award I’d won early on, back when I was still an individual contributor and eligible for that kind of award. When I finally left that August, I exercised the options from that small award and sold the same day. The company I’d worked hardest for, and cared about the most, is the one that handed me a check for about $900 on the way out.

So, as stated in my previous post, I was already getting frustrated and I hadn’t moved the industry forward. The companies I was with had some short-term successes, and I suppose I did OK, with the insult of a $900 check notwithstanding.

Still not addressing the bigger issue

However, underneath all of this was the same thing I’d felt watching the wagon scene. The playbook had run out and I didn’t have a next one written. I still didn’t have words for it. I just felt the urge to leave Silicon Valley. At least for a while.

I’ll leave the story here for now and come back to it in September. The Seattle years turned out to be far less straightforward than I expected, with two startups, an unplanned stretch away from work, and a consulting experiment along the way. Until then, I’ll continue with my regular posting schedule and circle back when it’s time to pick up the thread again.

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By early 2001, I didn’t feel like I was succeeding at anything. I wasn’t really making money, moving the industry forward, or even having as strong a family life at home that I wanted. Of course, hindsight is 20/20, and I couldn’t have written that as clearly then as I can now looking back. All I knew then was that something wasn’t working for me. The feeling built over eleven years in Silicon Valley and through experiences at three different companies, Oracle, Visioneer, and Latitude Communications. Each one added something different to the feeling.

Oracle and office politics

On paper, I think my years at Oracle (1990-1993) looked like they were going well for me. As a fresh graduate from my master’s program at MIT, I soon got promoted out of the cubicles into an office of my own, next to the VP’s. I was the product manager responsible for the most successful initial product launch on a single platform in Oracle’s history at the time (Oracle Data Browser V1.0 on Windows). I won an internal company award for my tour of 13 US cities and 5 European cities as part of that launch. On a lot of levels, I was actually having a good time.

On other levels, the internal politics wore on me constantly. My product, Oracle Data Browser, spent a year in alpha and a year in beta, not because the product itself wasn’t ready, but because it was built on shared libraries utilized by many product teams. The owners of the shared libraries were in the unenviable position of juggling priorities, and they solved it by fixing a handful of bugs for each product team, rather than wrestling any one team’s needs to the ground. The situation got serious enough where Larry Ellison’s chief of staff had to step in and create a “Product of the Month” club, where every open bug for one specific product had to get fixed before the shared libraries could move on to the next product’s bugs. The good news is that my product was first on that list. It just took longer than a month per product, but the products all eventually shipped.

At the time, what I learned was that I wasn’t happy to be in an environment where getting anything shipped required “winning” an internal political argument first. I got in my own head an idealistic view that by leaving for a startup, everyone would be on the same team. This was the first time I tried to change jobs to fix what was wearing on me.

Visioneer and executive misalignment

I joined Visioneer as employee #20 and its first product manager in 1993 at age 26. Candidly, I didn’t really pick Visioneer with much of a plan behind it. All I really understood about Oracle was that I wanted out of a really political environment, and the only alternative I could picture was a startup before the product had shipped, when everyone was supposedly still on the same team.

What I hadn’t figured out yet was that the moment a startup actually ships something, the same competing interests show up again, with just a different look. Our own executive team had been pulled together from a handful of different worlds, and nobody was fully reconciling those different visions across competing desires to target corporate end customers, OEM providers, consumers, or just tech early adopters. This lack of alignment left plenty of room for our lead Series B investor (Kleiner Perkins, as I wrote about previously) to end up dictating more of the strategy than any of us did.

Like my days at Oracle, some of the Visioneer experience was genuinely fun, if only in small slivers of the volume business. For example, I did enjoy the product evangelism. Local computer user groups were still a real thing in the mid-90s, and I often got tasked with traveling out to the bigger ones to do the 90’s version of influencer marketing. I’d present to the user group members, showing off the product like a Ginsu knife demonstration and offer a $100 discount on the spot for those who bought right then in the room. I would come home from these events with a pile of checks!

That said, most of my hours went into the daily grind of running product for a startup, on top of everything else the job required. The hours could be pretty bone-crushing. It probably wasn’t sustainable, though a company layoff kept me from ever finding how long I could have kept it up.

I found out I was being laid off while on a business trip to a Novell user conference, where I was scheduled to speak as one of their ISV (independent software vendor) partners about our integration with Novell GroupWise. I returned a voice mail from my CEO when I arrived at the hotel. When discussing my dismissal, I let him know I’d still give the talk and fly home afterwards to deal with actual termination paperwork. I didn’t want to tip off the market that Visioneer was going through internal turmoil. The CEO seemed genuinely moved that I chose to depart that way, and he treated me very well on my way out.

Silicon Valley turned out to be smaller than I expected. A recruiter who’d once worked for my boss heard about our layoff the day it happened and mentioned it to a mutual friend, who shared the news with a different friend of mine who was employee number 11 at a company called Latitude Communications. That friend also left me a voice message before I’d even made it home from that trip and encouraged me to interview there for a product manager position they just opened.

What actually convinced me to go with Latitude over my other job offers was watching how well its executives already understood each other. Most of them had worked together before, back at ROLM in the 1980s. When the CEO talked about a sales forecast, the VP of Sales and the VP of Marketing already understood what he meant. When he talked about a product plan, the VP of Marketing and the VP of Engineering did too. Visioneer’s executive team had been assembled from a variety of different backgrounds instead of growing together. Each executive team member individually was generally very talented, but I often felt the impact of their tendency to talk past each other despite that talent. Latitude looked like it had the fix for exactly that problem. Of course, that fix wasn’t enough to result in sustained success.

The unraveling at Latitude

I joined Latitude Communications in 1994. I was employee #30 and its first product manager. We built MeetingPlace, a data enabled voice conferencing server, years before anyone called it web conferencing. Its HQ was in Santa Clara, and ultimately, we expanded such that about half of my group went to our second office in San Francisco. We were a conferencing company, so when we outgrew our HQ building, we decided to open a second office in San Francisco to shorten the daily commutes of at least some of our employees while still keeping open the possibility of driving into our Santa Clara HQ when it mattered.

We grew consistently and became profitable. We went public in 1999, and I was an officer of a public company at age 32, first as VP of Product Management, and then as VP of Marketing also owning Product Management. That job at Latitude remains the favorite job of my career, for the culture and for the friends I made there.

Even though our product was a conference server, companies really weren’t buying just a product or technology. They were signing up to support an internal conferencing service, complete with IT deployment, help desk, and training considerations. Of course, conference calling was something that companies were previously outsourcing entirely, with AT&T being the dominant provider. Deploying our product and an in-house service had a real hard-dollar cost justification behind it, and the customers with enough scale to use it were genuinely happy, valuing the relationship as much as the product.

However, the proposition also involved nine to twelve month enterprise sales cycles, as our champions had to navigate the process of converting expense dollars into capital investments and headcount concerns. While the deals did often come in over time, errors in forecasting the exact timing of big deals could be brutal when Wall Street expected our results to be predictable one quarter at a time.

The market was also getting more competitive. Some of this was not surprising, as we expected competitive telecom carriers to compete more aggressively against AT&T on price. What did surprise us was how WebEx went after a completely different buyer. We were selling to IT and telecom departments trying to provide a conferencing service for their employees. WebEx sold directly to sales VPs who wanted to do remote presentations and demos to customers and prospects. That was a different approach and easier to absorb, with a model more similar to how companies were used to paying, by actual usage instead of hardware plus capacity-based software licensing we were selling. Ultimately, selling to interested end users with a service-based offering just proved to be a higher velocity commercial model than asking IT departments to purchase, deploy, and support on-premises conference servers.

The moment I actually realized where that left us didn’t happen at the office. It happened on a walk around Sharon Park in Menlo Park with Marsha and the kids. I’d been sitting in our executive staff meetings actively worrying with my colleagues about selling conference ports and concurrent user licenses, while WebEx executives were discussing their actual customer usage instead. Walking around that park, it was obvious to me there were two different mindsets, and theirs offered a better fit than ours to where the market was going.

I brought up this observation in our next executive staff meeting, and I got shut down. Everyone in that room was already stretched thin managing what Wall Street already knew about us, which were missed sales numbers and a stock that wasn’t recovering. There wasn’t much appetite left for changing how we would think and rebuilding the business model with new first principles. Even if we understood where things were heading, we just didn’t have it in us as a team to walk away from the model we’d already built and proven.

After missing our earnings projections, our stock went down. We had institutional investors, and there’s a mechanical cruelty to how that plays out. Once the price falls below a certain threshold, the institutions are forced sellers, whether or not they still believe in the business. A healthy share price rode down through $5, and eventually down to $1. Customers started pulling back right as the stock did, which created its own vicious cycle. We were still profitable when the slide started, but we ultimately had to do layoffs. Even though we weren’t a dot-com, our stock slide coincided with the dot-com bust, and I felt bad to have to let good people go. Of course, people eventually landed elsewhere but in many cases it just took longer than it should have just because of the timing of the dot-com bust.

What was it all for?

At this phase, I thought changing job situations would address what was wearing on me. For the first move from Oracle to Visioneer, I thought going from a big company full of office politics and many competing interests to a single-product startup would solve it. It didn’t. Then, I figured that going to a startup with an executive team more aligned at the outset would solve it. And that didn’t either. I continued feeling pretty worn out.

Also, there was a separate pattern running across the products and technologies I worked on. Oracle Data Browser, Visioneer PaperMax, and Latitude MeetingPlace all sold well for a while. Still, all three still got replaced within a few years by whatever came next, whether they took the form of new more advanced OLAP tools, multifunction peripherals, or cloud services like WebEx. It just didn’t feel like the products I put so much into were making a lasting impact.

It’s only looking back now that I can put it more plainly. So many aspects of those early job situations weren’t fun for me. I wasn’t moving the industry forward in any way that was going to last. With a layoff from one startup and a stock price of $1 at another, I wasn’t getting financially rewarded either. And then, with all the hours that Silicon Valley startups required at the time, I wasn’t running a great family life.

To net it out, after eleven years in Silicon Valley, I didn’t feel like I was succeeding at anything. I just didn’t have the words for it yet.

To be continued…

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A rough start

Even though Marsha and I had been friends since we were twelve, our marriage had a bit of a rough start. Marsha’s dad was not supportive of us getting married and made declarative statements to that effect. Ultimately, we had a small wedding with only my parents and sister attending, and we didn’t communicate with Marsha’s parents for about two years. This situation took a toll on both of us, and it led to Marsha’s first experience with individual therapy. She had to come to terms with the concept and the reality that she was without a family of origin. We did our best to just move on with our lives, and, in some ways, life became easier to navigate.

Once Marsha was pregnant with our older daughter, some repair came about. The coming of a grandchild prompted Marsha’s cousin’s wife to confront Marsha’s dad. She laid out very clearly that on the current course, Marsha and Stephen would just live happily without them forever, and he would never be part of knowing his grandchild. Given that Marsha’s dad was the eldest son in a Japanese family, no one else in the family with the same cultural baggage would have taken this on. Marsha’s cousin’s wife, on the other hand, married into the family and watched Marsha grow up. The process of reconciliation began at that point, and I remain grateful to this day for that interaction.

Rebuilding the relationship with Marsha’s parents played a large role in our decision to move back to the Seattle area back in 2001, shortly after our younger daughter was born. I was working through a genuinely stressful stretch at Latitude Communications, which is its own story, and I wasn’t spending the quantity time with our family that either of us wanted. Underneath all of that, we both had grown up with a different set of family rhythms and habits, and there were just some underlying issues we couldn’t fully describe at the time.

Still, Marsha and I both knew we needed a change. Moving to Seattle seemed like a good next step to get support from grandparents. So, we drove to Washington with our kids and our cat (Hank) in our minivan in March, 2001. Marsha’s dad ended up dying two weeks after we arrived. Our best laid plans to get support from grandparents turned into a period of family grieving.

Of course, the backstory here is that unbeknownst to Marsha (and her brother), Marsha’s dad had been fighting liver cancer and was refusing treatment. With the prospect of the family reuniting, he underwent his first chemotherapy treatment which his body was too weak at that point to tolerate.

The death of Marsha’s dad didn’t create the friction in our marriage but rather helped bring forward our different rhythms to the surface.

Marriage counseling begins

As we were starting to confront our own issues, Marsha wanted us to go into marriage counseling. She asked me to find a counselor, and I didn’t. Both frustrated and determined, Marsha went and started seeing one on her own. The counselor let her know that they could no longer move forward in the process without me, and that I had to join her. This wasn’t a proud moment in my life.

Still, I must admit that even though Marsha was frustrated enough to force the issue, she kept sending a consistent message at every step. She told me, in different ways many times over, that she loved me and that we were going to get through this together. At the same time, she made it clear she wasn’t afraid to make a change if I wasn’t willing to do my part. It wasn’t a threat as much as it was a clear intention on her part to do everything she could to make the marriage work, and she was asking me to do the same.

Marsha picked a really good counselor. She found someone that had experience working with men, including professional athletes from the Seattle Mariners and Seattle Seahawks. I’m not an athlete, so the sports connection itself wasn’t the point. To me, it demonstrated that Marsha was willing to look outside of herself to find someone that would work for me, too. That said, she still tried unsuccessfully to start marriage counseling alone.

This process started a few months after her dad’s death, once the most immediate grief of his passing had settled a bit. Still, I felt we were living in its wake. We probably went for a couple of months in total. Marsha’s mom watched our kids for us every time we went, which was just one of many small gestures from her side of the family. I must admit that I feel like Marsha’s mom (now deceased, too) and her brother (very much alive and kicking!) have gone out of their way to be good to me since the time that Marsha’s dad passed.

What we learned

Even though Marsha and I had very different rhythms, we always talked about everything. The therapist very fairly noticed that Marsha and I generally agreed on the facts and circumstances for any incident that we described. Where he helped was explaining why we came away feeling very differently about these incidents.

Marsha had more than 25 years of relationship and experiences with her own family before we ever got together, and I had that same span of years with mine. Neither of us could set that history and background aside just because we’d become a couple. The therapist told us that the two top issues he saw for couples at our stage were money and in-laws. We didn’t have money issues, so our conversations really focused on families of origin.

A key takeaway for me was the need not only to prioritize my own family (Marsha and our kids) over my family of origin, but also to do my best to help Marsha to feel that way. When I expressed the need to prioritize my own family with my parents, they largely agreed in principle. Still, even with this understanding, they didn’t always demonstrate that understanding in how they acted afterward. Even with the best intentions, old habits can die hard.

The tools that stuck with me

Given that Marsha and I were largely aligned in our objectives, the therapist was able to offer several tools, which I remember today.

A really useful one was rephrasing from “if” to “when.” Instead of spending our energy worrying about hypotheticals, we should work together on our responses. For example, instead of worrying what will happen IF a bear attacks us in the woods, we should collaborate on how we will respond together WHEN the bear attacks. Of course, the bear attacks were an analogy for unexpected situations with our families of origin. Shifting our focus to working together on a response over one-sided and endless worrying was a positive step!

Another useful tip was about our use of pronouns. Whenever possible, we should prefer the first person inclusive over the second person. For example, when a situation arises, instead of asking “what are YOU going to do about it?”, ask “how can WE solve this together?” There’s a lot of wisdom in this, particularly because each of us had established our own patterns in handling situations that could use some collaboration and refinement. Again, working together was a positive motion.

The last one was about bringing up past issues. The analogy here was a coffee table book. It was OK to take a book off the shelf to the coffee table, open it, look at it, discuss it, and eventually put it away. It was even OK to take it down again from time to time. What we didn’t want to do is leave the same book open on the coffee table indefinitely.

What lasted, and what didn’t

The shift from worrying about the potential of a situation to working together on a response was effective and got us through short-term situations in those early years. The tool became less relevant over time.

Probably the most lasting tool was the pronoun switch, or remembering to say “we.” We still remind ourselves of this today, and it really stuck with us. It’s why I used this tip as the title of this post.

What those initial tools couldn’t do for us was resolve feelings that had been sitting unprocessed for decades. Marsha can recall things that happened 30 years ago as clearly as if they happened yesterday. The situations themselves moved forward and got resolved logically at the time. The feelings underneath them didn’t. So, while she dutifully put the coffee table books back on the shelf, there was a backlog of books that she wanted to reopen.

That gap is what sent us back into counseling decades later, in our fifties. That round was less about pronouns and more about learning to ATTUNE to each other, the Gottman method I wrote about in a prior post (“Disrupting Patterns of Disappointment”), and about refining how we communicate with each other. (For more context, see my post about alexithymia.)

The first round of counseling was exactly right for the stage of marriage we were in, as it was very solution focused. The next round really had to explore more of the “why.”

Passing it forward

I’ve told part of this story before. In an earlier post (“Why am I willing to be so open?”), I mentioned a friend whose pastor told him that God makes people attracted to partners that “rub each other the wrong way” so the two of them can polish each other into two smoother stones. I said then that the story helped me put our own marriage counseling in context, and that there was more to tell later. (That later time is now!) We tell our girls that friction is not a bad thing in relationships because it helps people navigate to the other side.

Being open about our experiences with marriage counseling, and about my own reluctance to do it, has mattered to me well beyond our own marriage. During retirement, one person took me out to lunch specifically to thank me. Years earlier, on a business trip, I’d shared my own experience with marriage counseling with him, and it helped destigmatize the idea for him. Since retiring, nobody has ever taken me to lunch to thank me for the great products or business plans we made together while working years ago. I’ve just found that sharing life challenges with each other has a more lasting impact than past business accomplishments!

I later watched a video of Alain de Botton (“Why you will marry the wrong person - Google Zeitgeist”) making a related point that a successful marriage isn’t about finding someone without flaws. It’s about learning to negotiate the flaws each partner brings. Basically, de Botton was saying the same thing that my friend’s pastor told him. I mention that because I feel we’re all sort of living the same experience in private.

An ongoing journey

What we learned in our thirties got us through raising our families. As we became empty nesters, we realized that what we started wasn’t completely resolved by our fifties. Those of you following my health journey know that I’m about to undergo a set of procedures that will put me in recovery for a year to hopefully gain another twenty. What new learnings are ahead of us as we approach our seventies?

That question feels more real to me now than it used to. If this next round of treatment goes the way we hope, Marsha and I could have another twenty years together that might not have otherwise been available to us. Most couples historically didn’t get that many healthy decades together or the intention to keep growing their relationship. We are a bit like a mouse in a maze with few examples in our lives to follow, but we’re learning.

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A drawing that resonated with me

A few weeks ago while browsing Reddit, I came across a drawing that depicted a phenomenon I’d been observing with my consulting clients that I hadn’t described so succinctly. After a bunch of reverse image searches on Google, I couldn’t track down the original creator, but I copied it here.

The diagram shows three columns for ideas, execution, and usage for both the “before AI” and “after AI” eras. In the “before AI” era, it depicts a small group of people generating ideas, a slightly larger group focused on execution and scaling of those ideas, with a large swath of downstream users. In the “after AI” era, it depicts a very large group of people generating ideas, a relatively fixed number focused on execution, but very few successful downstream users.

Of course, one interpretation is that the “after AI” version is better because there are more people empowered to generate ideas and bring them forward. However, I think the real story is in the shrinking downstream usage column.

What I’m seeing in consulting work

I’ve personally observed a version of this phenomenon in my consulting work. AI adoption is certainly growing across functions, and the apparent productivity gains appear impressive at first. Sales people who used to spend an entire day putting together a proposal can now do it in minutes. Support engineers who used to have to escalate issues to more experienced colleagues now get immediate suggestions on potential next steps. I’ve seen similar results across many functions where the next steps almost always involve consulting with AI. And, in many cases, I think the productivity benefits are real.

Where I’ve been seeing potential breakdowns are that the work products don’t end up effecting the desired results downstream. I have always believed that it’s easier to replicate success than diagnose failure. Repeating successes is just key to scaling, and the ability to repeat success depends on consistently applying lessons learned.

The problem is that the AI often doesn’t really draw on the true organizational learning when it generates proposals, recommendations, analyses, and plans. General purpose AI tools, such as ChatGPT or Claude, are trained on publicly available data, and even when augmented with corporate data, that internal data often entails a mixture of outdated presentations, unresolved email threads, and backward looking data not representative of the current business situations. As such, the output generated by AI tools in use often sounds credible and well-reasoned but fails to incorporate the key insights known by the broader organization to produce results.

More concretely, by not rigidly applying lessons learned, there can be sales presentations that don’t result in closed deals, customer support solutions that don’t result in more long-term success in the accounts, or product features that simply don’t get used.

To me, the big part missing in discussions with my clients about AI strategy is how to utilize AI to build on and enhance organizational learning. So much of the focus has been on making individuals more capable, and how to develop the individual’s AI skills on the journey from AI-assisted to AI-augmented, to AI-native. Still, the employee’s ability to utilize AI agents in their work doesn’t automatically translate into stronger organizational learning.

What changed my thinking

Instead, what is changing my thinking about AI is how individuals often use AI to develop their own individual ideas. Some of this is good, for sure. Still, every company I have worked with already has more ideas than it knows what to do with. Sales teams have ideas. Product teams have ideas. Customers have ideas. Executives have ideas. The bottleneck was almost never generating possibilities. The bottleneck was almost always prioritizing which possibilities deserved attention and then learning from the results.

That realization caused me to think about playbooks differently. I used to view a playbook primarily as a set of instructions. A sales playbook was something that told salespeople how to run a deal. A support playbook told teams how to generate customer successes. Today, I think a better description is that a playbook is a common learning surface.

For example, scaling in sales can happen when 100 salespeople all engage with a common customer profile, messaging, and sales process. This allows the group to refine its customer objection handling and understand which value propositions resonate. They can learn together to discover which customer segments perform better. While variances with some individual sales people happen and are interesting, they become even more valuable when they occur within the same basic framework, so lessons can be applied by others, too.

When people are operating against a shared playbook, the rest of the organization can also learn from their experiences. Sales Operations can identify patterns. Product marketing can adjust positioning. Leadership can rethink priorities. The important thing is not that everyone follows the playbook perfectly. The important thing is that everyone is contributing information back into a common system of learning.

The virtuous cycle comes from the organization’s ability not only to adhere to the playbook but to keep improving it. This is where I believe AI systems should play a critical role.

The part that worries me

I’m not worried about AI helping individuals in lowering the bar to create new ideas. A salesperson can generate a custom pitch. A marketer can create a new positioning approach. A support engineer can design a brand-new workflow. Much of this output is surprisingly good. In some cases it may even be better than what exists in the official playbook.

The issue is that every individualized version creates its own learning loop. There is a big difference between a hundred people improving one playbook and a hundred people improving a hundred different playbooks. In both situations people are learning, but only one of them creates organizational leverage. Utilizing the same, shared framework makes it easier to compare results, identify patterns, and refine the system. When everyone is working from their own AI-generated approach, the individual learnings become harder to aggregate and harder to interpret.

Individual ideas and deviations from the playbook have always existed. Great salespeople have always improvised and good managers have always tolerated a certain amount of drift from the script. What made that manageable was that deviation happened slowly enough and visibly enough for organizations to observe it and decide whether the change should become part of the playbook. AI changes that equation.

The problem is that widespread AI usage makes deviation fast, inexpensive, and often invisible. The deviation on its own is fine. The problems arise when organizations are unable to see the deviations clearly and learn from the outcomes. Without that feedback loop, everyone ends up choosing their own adventure. That may be empowering for individuals, but it does not necessarily help the organization learn.

The proposal that should never have existed

I observed this in my own consulting work. In that organization, the sales playbook called for the salespeople to identify the members of the actual buying committee before qualifying an opportunity. Numerous past deals demonstrated that involving the right stakeholders upfront made the deal more likely to renew, expand, and produce long-term customer value.

However, applying that lesson learned always involves more work for the salespeople, particularly when there are quarterly sales targets. In more than one example, AI was used to create highly customized, thoughtful, and persuasive proposals aimed at specific individuals in the account most likely to sign on their own, without the rest of the buying committee. The deals closed in the short term. The problem is that the organization had already learned that this kind of deal often performs poorly over time, and, consistent with those learnings, those deals resulted in customer churn.

In these cases, the proposals weren’t bad. AI didn’t create any mistakes. It simply made it easier to route around the institutional learning embedded in the playbook.

Why this reminds me of product marketing

This lesson in sales is consistent with one of my earlier writings about product marketing, where I focused on separating meaning from voice for AI content systems. In that piece, I argued that product marketing should own meaning, brand should own voice, and segment marketing should own a personalization layer for the type of customer targeted. The concept is that the AI tooling should be wired to render those shared assets into the form needed (e.g., sales email, web copy, blog post, etc.). This framework allows insights to be captured once, improved collectively, and adapted as appropriate.

Getting back to the diagram above, I believe the highest leverage use of AI isn’t helping every employee generate their own ideas, but rather helping the people responsible for the strategies and idea curation learn faster from the people executing it. When used this way, AI then becomes the enabler for accelerating organizational learning rather than fragmenting it.

The question I keep coming back to

While many are touting AI as a way to improve individual productivity because those gains are easier to observe, I want to focus on how AI can make organizations learn faster.

This shift toward using AI to strengthen organizational learning will involve a lot of instrumentation. How does feedback from the field actually reach the people responsible for improving the system? How does the next version of the playbook incorporate the learnings? How do we use AI to strengthen the connection between execution and learning?

To me, the Usage column is the most important in the drawing. While everyone notices the explosion in ideas, I don’t believe that more ideas necessarily lead to scale. I believe organizations scale when large numbers of people contribute to the same playbook to generate results. More ideas without more usage isn’t progress. It’s just more ideas.

“On Roche Harbor, everything comes with an island tax, including the view.”

We spent July 15 through July 18 on San Juan Island, our first visit to Roche Harbor, staying in a home managed by the resort. The occasion was Marsha’s cousin’s 70th birthday, timed close enough to my own that we celebrated both together.

Roche Harbor is his favorite place in the world. He is an avid boater and fisherman, and he spends as much of every summer there as his construction company allows. Summer is also that business’s busiest season, so full time retirement there is still a few years off for him even though he would love it now.

Getting the four of us there took real coordination. Our older daughter flew in from Columbia, South Carolina, and our younger daughter flew in from Chicago. Both landed at SeaTac and stayed with Marsha’s brother, and we picked them up on our way north from Portland. From there, all four of us flew from Kenmore to Roche Harbor on a Kenmore Air seaplane. Marsha’s cousin and his wife stayed on their own boat in the harbor, and his two daughters stayed at the Quarryman, while we stayed in our rental.

Some things we enjoyed

The weather cooperated the whole trip, sunny and cool, with the kind of clean ocean air that made just standing outside feel good.

The seafood was the real story of the visit. Dinner at McMillin’s started with prawns and calamari, and I followed that with crab bisque, bread, and petrale sole, plus a sundae to finish. The Westcott Bay oysters we had were the best I have ever eaten. A stand right on the dock sold us spot prawns straight off the boat, Marsha’s cousin brought in fresh crab from his own crab pot, and his boat neighbor shared salmon he had just caught that day. One night we had San Juan paella catered at the rental for the family celebration, so nobody had to cook. The salad and the tapas were excellent. The paella itself was not really to my taste, but everything around it was.

Saturday brought a small dockside event, a live jazz band and beer from San Juan Brewing. Every night around 8pm, the resort runs what I learned is called its Colors Ceremony, a tradition going back to 1957. Music plays, the flags come down, a trumpet sounds, and a cannon fires. It is a genuinely nice way to end the day.

The people running the harbor were friendly across the board, right down to donuts appearing most mornings.

Some surprises

The island tax was real. Food, lodging, and getting there all cost more once a place is only reachable by boat or plane. Marsha’s cousin’s own numbers were on a different scale entirely, between his mooring fees and the general cost of keeping a boat.

There is no medical care on site. Everything is a boat or plane ride away, and that alone is a personal dealbreaker for me.

We lost a full day to a hard rain on Thursday and stayed in with takeout pizza.

Roche Harbor is more exclusive than it looks. The waitlist to moor a boat there runs close to 40 years. Most of the homes seem to be summer places, managed as rentals when their owners are away, and waterfront land is limited enough that owning one is probably a strong investment even though almost nobody treats one as a full time retirement home.

Days after we got home, a Kenmore Air seaplane went down near Sucia Island on the same Lake Union to Roche Harbor route we had just flown. All 11 people aboard survived, four were hospitalized, and one was listed in critical condition. We had taken that route specifically to avoid the ferry line, so the news landed differently once we knew.

Where this leaves us

I am not eager to go back. Motion sickness rules out ferries, seaplanes, boats, and even a floating dock, which does not leave much of Roche Harbor open to me.

Our older daughter had the opposite reaction. She never grew up boating because of my motion sickness, and this was her first time out on the water, with Marsha’s cousin driving. She saw orcas, went fishing, and had a great time. I think our younger daughter would want to go back too.

If this is really about time with that side of the family, a summer in Roche Harbor still beats what we currently do, which is fly back to Bellevue every New Year into bad weather and a worse drive.

Has anyone else found a place that works better for the family than it does for you personally?

Note that Pangram believes this version was also fully human written!

“Island pricing is simple. First you pay for the item. Then you pay for its entire journey.”
— Anonymous

Two weeks ago, I mentioned we went on vacation to celebrate the 70th birthday of Marsha’s cousin. He is an active boater and fisherman, and Roche Harbor on San Juan island is his favorite place in the world. Even though summer is the busiest time of year for his construction company, he tries to spend as much free time up there as he can. We’d never been there before, and his wife appropriately made the call that it was about time that the Pao family made the pilgrimage.

Given that I always now look at places like this with the eyes of a “retirement blogger,” I felt compelled to write about our experience here, as well as to share my own thoughts about the place as a potential place to retire. The net here is that I feel Roche Harbor is a great place to visit and perhaps less of a place to call “home.”

Getting there

Roche Harbor is busy in the summer, and reservations for accommodations for larger parties require planning because there are so many weddings held there. Still, we were able to find available accommodations at a time when both our daughters were able to fly out and Marsha’s cousin’s daughters could also come. The Pao family stayed at a rental home managed by the resort, Marsha’s cousin’s daughters stayed at Quarryman Hall. Marsha’s cousin and his wife stayed on their boat in the harbor.

Getting to Roche Harbor isn’t easy either. Taking the ferry from Anacortes makes for a long, 3 hour journey from Seattle, so we all took a Kenmore Air seaplane, which is just a 45 minute flight. It’s not cheap, but for a one-time visit, it was worth it! We took over all but one seat on the plane.

Some things we enjoyed

Summer temperatures. The combination of the mild Pacific Northwest summer temperatures and the crisp ocean air make for just a very pleasant outdoor experience. The little resort town is just so charming with artist stands, little shops, and eateries.

Fine dining. We did our first night dinner at McMillin’s, which was outstanding. We were all impressed with the prawns and calamari as appetizers. I really enjoyed my crab bisque and petrale sole. I tasted my older daughter’s salmon and my younger daughter’s sable fish, and I thought those dishes, too, were excellent. I eagerly ate the rest of Marsha’s flame-grilled prime rib as leftovers a couple days later, and it was very good (although not among the best steaks I’ve had in life).

Casual dining. The next day, we had lunch at Westcott Bay, and the “Little Olys” are probably the best oysters I’ve had in my life. Even though I get really seasick, I felt it was definitely worth the boat ride out just to eat there. The clam bowl was also excellent. We should have skipped the mezze platter and just eaten more seafood!

The seafood there in that part of the Northwest seems to be just so uniformly good. Marsha’s cousin caught fresh crabs in his crab pot, their boat neighbor gave us some fresh caught salmon, and Keith, who has a stand right on the dock, has amazing spot prawns.

At-home catering. It was also fun to get dinner catered for us one night. Paellas San Juan came to our rental home and made a feast. Candidly, the seafood paella wasn’t my thing, as I think I preferred just eating the local seafood on its own. Still, the salad and tapas were excellent, as was the whole experience. It was nice to do an evening at “home away from home” for an extended birthday celebration for Marsha’s cousin, without worrying about restaurants having to turn tables.

Events. Every night at sunset, there is a cool “Colors” ceremony where they play the national anthems of the US and Canada, and then shoot a cannon! Local boaters also participate in the festivities by honking the horns after the cannon. It is really beautiful to be outside at that time in the evening.

We also attended a very daytime fun event serving San Juan Brewer beers, hosted right off the dock where there was a live jazz band.

Boating. Our kids really enjoyed the boating part of the trip. Given that I get really seasick, we were never a boating or fishing family. That said, Marsha’s cousin took the kids out on his boat, and they all had a great time, even spotting some Orca whales! Marsha graciously hung back with me on shore to keep me company. I know that day our older daughter got the boating bug, and she intends to return with her husband at some point. He had to miss this trip to attend a bachelor party in Kraków, Poland for a long time friend.

Overall, we had a really special time there with family, and this trip, while short, was full of wonderful memories. I can definitely see why retired people enjoy spending time in Roche Harbor.

Some surprises

Costs. Probably the biggest surprise to me was how expensive everything was there. It’s expensive to get there (over $400 roundtrip per person on the seaplane) and expensive to stay there (over $3,000 for a 3-night minimum stay). Moreover, anything purchased there is more expensive. Conservatively, it seemed like a bottle of nice alcohol (e.g., Veuve or Grey Goose) cost at least $20 more on the island than on the mainland!

Of course, when Marsha’s cousin also shared the cost of mooring, fueling, and maintaining his boat there, we were talking about a totally different type of expense. I won’t share his actual numbers, but a quick Google search estimated that for a typical 35 to 55-foot power boat kept in Roche Harbor all year round, owners should expect to spend between $23,000 and $46,000+ per year in total cash outlays. Still, there is no lack of demand, and he told us that the wait list is now over 40 years long to get a spot there.

Rain. We lost a day of our vacation to a pretty severe rain storm. We got drenched that day. Fortunately, our rental home had an in-unit washer/dryer. Still, there were no outdoor activities the rest of that day, and Marsha was a hero picking up takeout pizza and salad from Lime Kiln Cafe at the bottom of our hill, using an extra jacket borrowed from her cousin’s wife. While the region’s weather is known for a broader summer stability, there are localized “microclimate anomalies” which cause “unseasonal maritime disruptions.” Another downside of island living.

Dangers of seaplanes. For a more serious risk associated with island living, we were surprised to learn that just a few days after we returned from Roche Harbor, Kenmore Air experienced a seaplane crash from Seattle to Roche Harbor. The pilot and 10 passengers survived, but three remain hospitalized longer-term. This incident highlighted how seaplanes introduce some added risk because operating on water removes almost all the safety infrastructure standard land aviation relies on. It also highlighted the problem with access to medical care on the island.

Distance from emergency medical care. Hospitalizations after the crash required that patients be flown via helicopter to Bellingham and Seattle for ongoing care. Typically, medical emergencies on the San Juan islands require air transport to a hospital on the mainland. While plane crashes are unique occurrences, medical emergencies get more common as we all age. This is a big difference to our lives in Portland, where we’re just 2 miles from OHSU.

Where this leaves us

At a personal level, I myself would never consider Roche Harbor as a permanent retirement destination. I know I have a pretty unique medical situation, and living too far from a leading hospital pretty much disqualifies it. In addition, my own motion sickness makes ferries, seaplanes, boats, and even floating docks pretty unpleasant, so it’s hard to imagine making a life for myself out there.

I believe the numbers reveal that my views are pretty common. The population of Roche Harbor is estimated to be fewer than 800 residents, whereas the transient overnight guests number about 2,500-3,000 during peak seasons, with another 1,000+ day trippers. In other words, Roche Harbor is largely a place to visit, not live.

This makes sense to me. Despite my reservations about any sort of permanent home there, on balance, I think I’d prefer to reunite with family over summer there in Roche Harbor over Bellevue at New Year’s like we do right now. Those New Year’s visits almost always involve a terrible drive from Portland up I-5 in inclement weather, icy and steep streets in South Bellevue, and even less daylight. While the geographic difference is only about 2 degrees of latitude, the perceived gloominess is just a lot higher in South Bellevue when combining the terrain and low cloud cover. Moreover, a significant part of the vacation is always spent stressing about preparing traditional Japanese dishes that aren’t fully appreciated by the younger generations anyway. As I mentioned earlier, our older daughter would like to return to Roche Harbor, and I think our younger daughter would be game, too. Still, with the costs involved, I think both returning might be dependent on whether others (e.g., Mom and Dad) foot the bill!

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Author’s note: I normally use AI to assist with preparing these pieces. However, given that Substack has now started using Pangram to analyze posts, I decided to go “all human” this time around to see if Substack can properly profile my own writing in the absence of any AI assistance. (It did!) My own “How I make this” section Substack does fully disclose my normal usage of AI.