These sounds are falling through my mind
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.
“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?
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.
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!
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.
Random thoughts in bullet form.
Quote from a founder call this morning: “The reframe sits closer to discovering yourself in the ships versus the ship itself.”
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
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.
Stripe is incredibly well positioned to compete directly with Shopify. It sounds incredibly unfocused, but I can map the dots.
Profile, identity, and trust. A consumer-side marketplace that knows buying behaviours, returns, and chargebacks. The ability to build incredible look-alike audiences. An inventory manager, think TradeGecko, sitting inside a payment processor. I’m imagining an agentic marketplace. Containers + inventory.
For merchants, if you’re already paying for ads, why wouldn’t you just run them through Stripe directly? Unsure what value Shopify provides in that world.
Sundays are my favourite day of the week.
Slight embarrassment to share: sitting in a cafe in West Vancouver, and there’s 3 other people doing the exact same thing I am right now. Leaning in, looking up in deep contemplation, talking into their screens, chatting directly to the command line. It’s weird.
Thursday afternoon my concierge flagged a package. Looked at it and thought, pretty sure I didn’t order anything. I opened it anyway. Caroline, Emmett, and the LP crew had sent Unreasonable Hospitality by Will Guidara. Thanks! Halfway through. So far, the takeaway = it’s not about the execution, but how you make people feel in the execution.
It’s the first day of spring, share your flowers!
Vancouver skyline is showing off today. Heading over to Kits for a founder meeting, then a remote coffee work session, before hitting an art store.
Founder friends, just came across a 500k grant for countries in the Eureka network. Covers Europe, South America, and Singapore. Shared it in a few Slack communities already but worth putting here too.
https://nrc.canada.ca/en/irap/about/international/?action=view&id=278
Remember web 2.0 social or pixel avatars from 10 years back? Claude may kickstart agentic 8bit avatars and more. New blog post - https://kenny.is/claude-pixel-avatar-maker/
Testing out a new gallery for daily log. A few photos from this afternoon.
New Boom TLD secured!! Will share later!
At least three times this afternoon I caught myself giggling at BOOM or if anyone actually cares about a headless shareable room builder in this AI era, especially one named Boom. And is it boom, Boom, or BOOM?
My new rules for picking side quest domains? No more than 10 minutes and 10 dollars.
Successfully recorded my first Boom video, 5 minutes, a little bit salesy, and all on my 2nd take. When creating anything, we are our own worst judge. The inner critic can rage. Ironically there’s that clip going around Twitter that screams the complete opposite. The ultra successful have zero introspection. Well, good for them I suppose.
The good news about whatever side quest you’re building → this is the worst it’ll ever be.
Last night I shipped a rough version of Boom! It deserves a blog post of sorts, and sitting as a subdomain for the time being. There’s another tab open trying to find a Boom TLD. Been working through bugs and polish all morning!
The last 20% always takes the longest. The last 5% even more so.
The good thing with AI is shocking degree to which a task (whether you are an engineer, designer, or PM) can be brought to 80%. The bottleneck then becomes people who can tell the difference between the 80% and 100%.
— Dan Grover (@DanGrover) March 13, 2026
Working until 6pm, then sending the newsletter. Finally.
Oh ya, and struggling with export settings with design assets, colours feeling washed out. Think I finally resolved it. Sharing this as more of a live dogfood test.