Daily log


These sounds are falling through my mind

creative maps only take you so far

feel your way

Re - acting and the creative act

“total immersion into possibility. It’s infinitely interesting, there’s no bottom to it. A lot of it just great, deep, belief”

8:28 is like flying

bring people into the theatre

Quick reflection before kicking off several 30-day challenges. May had a bunch of highs and lows.

Highs = Lost 8 lb, increased VO2 max by 6 points and daily steps to 14k. Wrapped a number of personal and offline projects that I’m withholding for now.

Lows = last commit to Boom was over two weeks ago, newsletter over a month

My biggest takeaway for this month. Crushing offline or non digital to-do list items feels heavier. The good kind of heavy. More uplifting and carries momentum

june 01

Officially wrapped two projects today, as well as a bunch of personal DIY offline projects.

It’s been neat to watch Vancouver slowly decorate itself in time for the World Cup. Not entirely convinced locals are that excited but when it officially kicks off in two weeks I know it will mirror that of the 2010 Olympics.

On the builder side of things, today I submitted name requests for a company inc, which is always a lot of fun and thrilling bc things start to become real. More on that later.

Observation: there’s a lot of hype or focus on distribution first, especially from all of the marketing camps and marketing ai agent startups. Distribution for the sake of distribution. It’s one way of operating. <retracted>. if time allows it, I’ll write a few words and put some slides together on where we’re going or what has me excited. The questions I hear constantly within my circles from other builders not knowing what to build, which hills to stand on, and this obsession around distribution. More later

Speaking of obsession, I caught the breakout film Obsession earlier this week and highly recommend going in cold without a trailer.

wrap, and the world cup is heating up

This afternoon checked out Web Summit Vancouver, met up with a few founder friends and a bunch of faces that I haven’t seen in a minute. Hoping to chat with a few people and friends of friends from Singapore and Southeast Asia that made the big trek. Attaching a few photos below.

Web Summit Vancouver 2025

“Planning and execution. That’s all there is.”

The room was absolutely packed. My friend Nate had invited me down to Palm Springs and treated me to a surprise evening at the Purple Room, a drag queen musical. Our dinner table was right near the front, and Jeremy, seated to my right, caught my attention early as he dropped various business knowledge bombs between numbers. He was in his 60s, a successful entrepreneur who’d felt the full weight of the wins and losses that come with a long career of company building.

His point was that when a project or venture goes sideways, it’s almost always one of those two. Sometimes the plan was wrong from the start. Sometimes you executed flawlessly against a plan that was never going to work. Sometimes the plan was right and the execution fell apart. Occasionally it’s both.

It’s been 11 years since that conversation. I’ve replaced post-mortems with a simple stress test: did we have the right plan, and did we execute the plan?

Planning and Execution

Wrapped two huge projects and a 14-day pilates challenge. The reformer ain’t no joke. Kicking off a 30-day challenge starting right now.

Web Summit Vancouver starts Sunday night. My schedule is getting a bit jammed but curious what this year’s theme will entail.

The Reformer Frame

Sun is pumping in Vancouver today. Sitting outside the Vancouver Art Gallery doing a bit of a quarterly reset. Head down, Moleskine out, thinking through what the next few months actually look like.

This weekend I’m hoping to finish an alpha of Boom. The last 5% of even a rough MVP is always the hardest. This has been a 30 day build and this weekend will mark the only time in Figma. And it sorta shows haha.. Sunday is the day where I’m planning to pour in some polish and actual soul. Make Boom fun, at least to me.. that was always the whole point of this thing!

Sun's Out in Van

Spring is here. My evenings lately have been deep in Boom. Writing this from Whispr, so I can’t scroll back and see what I’ve already shared. A lot has happened. Full refactor, dozens of new features, plenty of failed experiments too. Mostly when trying to let Claude run loose.

Claude is running a smoke test on Stripe.

Spring is Here

Random thoughts in bullet form.

  • Just returned from an ice hockey game. We won!
  • Two days left in the quarter and I officially have more ideas than I have time.
  • The four moments that hit hardest when building something new; getting lost in the idea maze, waking up to a fresh Figma file, adding Stripe subscription capabilities, and your first paying customer you don’t know.
  • Has the term builder been washed out? Yeah, probably.
  • Reminder to self. Everything and everyone has seasons.
Replace Sunday Scaries with Sunday Supersets

Running a few projects this afternoon.

First up, a personal dev project. Claude + Notion + deep research.

Second, a hugggge Boom update that includes new domain, migration, backend refactoring, headless, a bunch of agentic stuff. This version is so hilariously ambitious, but pushing the agents hard. More on Boom in a second, but Claude thinks it’s 16 weeks of dev work in 3-4 days. Sure, Jan! We’ll see. Going to fire up Conductor and let it rip!

The third thing is more of a frustration or short rant. Planning for AI execution is hard. The fitness analogy lands for me: if I have a six-month goal to run a half-marathon at a specific pace, there’s research, sequencing, machine + human collabs, maybe external data sources. It’s not linear. Yesterday I was deep in some of this and it kept refactoring existing text plans and chunking things wrong. Blah blah blah.

I want a new type of space between Notion and Claude. This whole third space or fourth space thing has been overused.

The way it currently feels for me: Claude feels AI generative. Notion feels human generative. Where is somewhere in the middle, man?

I want something that leans human. A private collaborative workspace where you set the goals and accountability benchmarks (real humans versus agents) and remain the author, the main person holding the pen on your adventure. Sure AI is there and you can dial up and down as much as your heart desires but it’s mostly in the background. This works in single, multi-player, or even multi-agent mode. Whatever this category thing is the space I’m exploring with Boom! A human first headless accountability and intention layer.

Second screen and headphone status:

^54 min track is fire, bassline

Intentional Layers with Barry Can't Swim

Four days left in the quarter. What can you ship?

Perceptions are top of mind lately. My general rule: revisit marketing perceptions every quarter. Keep questioning and double guessing myself… Everything is moving so fast? Maybe every six weeks? Maybe every six months. arg.

The trend I keep seeing, with other founders and myself, is a spike in micro AI builds. The reps matter, we need to compound learnings and not get left behind. Just make sure there’s overlap. Tie it into your marketing perceptions, quarterly goals, values, your North Star mission.

If you’re stuck on the “what to build” question, that’s probably where to start.

What to Build
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