Joined a new AI-native company this week and it’s kind of wild how different it feels already. The laptop arrived, I logged in, and an agent basically took over from there. It set up my dev env, pulled repos, fixed dependency issues, got permissions approved, pointed me at the backlog, linked the architecture docs, and surfaced the Slack debates I actually needed to read before touching production. When I needed context on something, I asked the agent and it found the exact thread from months ago explaining why a decision was made, who owned it, the related Linear issues, and the PRs connected to it. I’ve only been here 3 days but it honestly feels like I’ve worked here for a year because the usual friction and scavenger hunt for context just isn’t there anymore. We should probably stop calling this “onboarding” and rename it to “mounting” because this feels a lot more like mounting a distributed filesystem called “institutional memory” than slowly getting drip-fed context over 6 months.

It’s okay. Yesterday at @SpellbookLegal instead of running costly evals, we asked Fable 5 to generate a replacement Fable 5 as we suspected this would happen.

You don’t get poorer because someone builds a trillion dollars of value. You get poorer when nobody does.

Spending too much time in contracts. This is the top "Elon" typo ever. Elon's comp package is supposed to be based on SpaceX market cap milestones... SEC filed document has a typo and it points to the Mars colony instead. Imagine being the junior associate: Good news, I found the broken cross reference. Bad news, it points to Mars!

An executive IC is either the best idea I've had or a very public midlife crisis. I’ve had a lot of DMs asking: won't you just step on everyone's toes? Is this a Peter Pan role for someone who doesn't want to grow up? For the record, they might be right. This could flop. But it felt worth a shot. I'm the oldest person in the company, which is a little daunting. My 80s SNL reference last week got blank stares. Three weeks in, this is how it's played out so far... The first thing is being in enough rooms to see across everything at once. I'm in the product review and the sales call in the same day. Pattern-matching across those rooms, combined with my experience, and giving feedback in real time is worth more than 100 board members debating CAC in a deck. The second is that being new and senior at the same time turns out to be a strange superpower. I interrupted the all-hands last week, the entire company on the call, not planned. Something looked off and I just said it. What are they going to do, fire me? Maybe your filter goes away over time, and impatience with just saying the thing. The third is something I didn't fully anticipate, which is how much of the role is helping people get things to the finish line. "No, not good enough, let's take another stab," or "ship it, it's perfect." That speeds things up more than I expected. The best part is jumping in to pair with people and teams on a better version than they thought was possible. And quickly. An on-the-field coach who can ship with the team. People assume the role is mostly about writing code. It's not, but yes, I've written plenty, because that's how I learn. A few PRs are in production and I'm now working on more infrastructure-level tools. You'll see some of my work launch in about 10 days, and hopefully it makes a bit of a splash. It wouldn't have happened this fast if I didn't have the time to own it end to end. I'm sure the role will keep evolving and changing shape. But it's exactly as fun as I was hoping. Were still figuring this out in public, so if you have questions, or suspect I'm kidding myself, ask away.

We evaluate legal AI like reliability engineering, not leaderboard scores. Same contracts, same sources, same @SpellbookLegal secret sauce. Opus 4.8 failed our consistency bar. That's why we haven't made it the default yet.

My best ideas happen during workouts or Sunday morning long bike rides. I used to have to think hard to remember, then jot down a quick reminder and email myself a "don't forget note" then pick it up on Monday morning. Now I talk to Siri via air pods to email @stillaai with the framework of the idea. The email references a few skills I've built: brainstorm, challenge, narrow, analyze, present options. While I'm still riding, agents are arguing with the idea, finding flaws, exploring alternatives, building examples, mocking things up, and drafting press releases. I always ask for a polished HTML report to review. The weird part isn't that AI can write code. That was cute. The weird part is that random thoughts now have a CI/CD pipeline. Living in the future is still the best feeling of my entire career.

There are two types of people in the world. Those who make fun of your NB. And those who borrow yours after trying them on.

One of the underrated side-effects of having so many ex-colleagues go build great companies is that when you use their products, you just invite them into your Slack and keep hanging out. Way less awkward than running into your ex at a grocery store. @stillaai

People keep saying “welcome back” today after the Spellbook announcement. I keep correcting them. This last 5 years were probably the hardest building years of my career. Post-Shopify I simply went heads down. Built products. Shipped a new product from nothing, new company, and a boat. Rebuilt my technical instincts from scratch. Learned AI by using it 12 hours a day instead of talking about it on panels. I wasn't gone, I was in the gym.

Very stoked about my next adventure. I’ve joined Spellbook, but not as CTO. I’m joining as an Executive IC. It probably means different things to different people. It means I'm here to build and be hands on in every part of the company. I've invested and been advising and getting to know @scottastevenson and the team for more than a year. At some point it became obvious the most useful thing I could do was stop talking about ideas and go work with the team. With AI making code cheap to copy, what's going to be hard to copy is the shape of a company. How a team learns, decides, and ships. That's what I want to work on. It's what I've spent the last three decades learning to do. Why Spellbook? The world has entered into one of the largest investment cycles in decades. Trillions of dollars are being deployed into energy, AI, manufacturing, transportation and the modernization of critical global systems. Despite this, progress still moves at the speed of contracts. Spellbook’s mission is to modernize the $1 trillion transactional legal market so the contract system can keep pace with the global economy. At the same time, every contract ever signed is becoming searchable, comparable, and weaponizable by counterparties, regulators, and plaintiffs' lawyers. You will be attacked. We're hiring. Slight bias toward Canada, but remote-friendly for great talent. DM me.

I used to take 50 flights a year, customer dinners, and sitting through 400 hours of sales calls trying to “stay close to the customer.” Today I pointed our internal AI tool at a year of Gong recordings and it built me a 6 hour supercut of the best demos, worst demos, lost deals, painful onboarding calls, and the exact moment customers got excited. Not sure if this is the future or just corporate Netflix.

Raising kids is weird because eventually they just fork your spouse.

Spent time today reading through one of Anthropic’s massive Claude prompts after sniffing the network traffic. A 1,500 line prompt! What surprised me wasn’t the personality tuning. It was the amount of embedded operational logic. Large parts were more akin to a programming language. API doc outlines, code samples, tool routing rules, formatting protocols, javascript snippets with dos/donts. I used to think prompting is about wording, but these models are now invisible runtime systems behind a chat UI.

Dress for the job you want. Some people peaked in varsity jackets, I peaked in grey t-shirt.

It’s hard to explain how fun it is to build right now. There’s also an additional Shopify origin story behind why this moment feels strangely familiar to me. Early Shopify, a few people on the infra team realized something important: every time someone logged into a terminal and typed commands into production, knowledge disappeared. Nobody else saw what happened, nobody learned from it, and the second exit was called the know-how was basically gone forever. So they built a /command system in Slack that let people run Unix commands and internal infra helpers directly from chat. At first it seemed almost silly, but the effect was profound. Some people objected, « you’re just cloning what you can do in the terminal, it’s a waste of time ». But incidents became collaborative instead of isolated. Troubleshooting became searchable. New engineers could follow along in real time and see how systems were actually operated under pressure instead of reading stale docs written six months later. Slack quietly became the terminal. That experience changed how I thought about software and teams. The best builders are not just increasing leverage or automating work. They’re building systems that capture and compound learning across an organization. A lot of the magic companies develop internally usually evaporates into terminals, meetings, DMs, and people’s heads.
 Coding is becoming less single-player. Research is becoming less single-player. Even debugging, operations, and product thinking are turning into shared surfaces where humans and AI work together in public. You can literally watch ideas form, evolve, get challenged, and turn into working systems in real time.
 It feels like we’re finally building systems that make groups of people smarter together. Not just individually productive.

I did a lap of our app traffic patterns this morning. It gave me some feels. It’s not quite pride. It’s harder to pin down than that. You take something that didn’t exist, push it into reality, and suddenly it’s just… part of the world. People use it without thinking about it. SeaPeople didn’t exist 2.5 years ago. Now it’s used across the entire planet. Every ocean, river, lake. It doesn’t make that much money and we didn't have a big raise or unicorn status. We just built something we thought the world needed. More people should build. PS: Thanks @supabase for the cool 7-day traffic viz. I didn't upgrade to the 14 -day view as this one gave me all the feels 😬

I’ve spent my life building software. This was different. The ocean is harsh, indifferent. In software, failure is a log. On the ocean, it’s a lesson you feel immediately. It took 5 years and 500 people to get Windigo here. Sweating every detail together. We've sailed her over 11,000 miles. Now we're on the cover & named boat of the year! Blown away and humbled. What a team effort!

Infinite code. Finite problems worth solving this month. Humans are bad at saying no. “No” requires explanation, confidence, ownership, taste. “Yes” requires… nothing. So we drift toward yes. Now “No” is the job.