Have babies with the wrong person…

Hello friend,

Do not read the next paragraph unless you're interesting.

SERIOUSLY DO NOT.

For the last four years, I've been inviting a bunch of my most interesting friends to Victoria at the most beautiful time of year (July 27-29th) to eat amazing food, hang out in nature, and get to know one another.

I call it Interesting People.

This year's group includes Hannibal Buress, Josh Johnson, Tim Heidecker, Kevin Rose, Steph Smith, Dr. Rhonda Patrick, Tom Junod, Dan Mangan and 150 or so others from the worlds of music, film, comedy, business, science, writing, philanthropy, and even (non-cringe) magic.

It is, without a doubt, the coolest room of people I've ever been in.

Each year, I invite some randoms like you to keep things interesting.

You can read more about the event here.

We only have a handful of VIP and regular seats left (scholarships are full unfortunately), but if you're interesting, you should apply!

Here's what I'm thinking about…

Last Tuesday at 11:43pm, Zoe gave birth to our daughter.

She came out looking like an alien.

The umbilical cord still beating, covered in blood. Her head shaped like a cone from an hour of being pushed through the birth canal.

Then I held her against my skin.

Suddenly, my brain was flooded with some magical, baby-induced opioid.

The world stopped and all my existential anxieties disappeared.

What's interesting is that I was kind of terrified of having another baby.

I wanted to have another child, obviously.

Logically, I knew I wanted more kids. Especially my first daughter.

But I'm 40 years old. My boys are 6 and 9, and I'd moved into a chiller phase of parenting. One that didn't involve disrupted sleep, crying, or diaper blowouts.

Read the full essay →

They say bad things come in threes.

But good things too!

I just went on three podcasts. If you've got a long drive or a workout, here's a few hours of certified Andrew Wilkinson™ content.

Make It Click with Willson Cross: Why I quit drinking and why Divorce is Awesome became my biggest post ever.

Spotify / Apple Podcasts / YouTube

The Startup Ideas Podcast with Greg Isenberg: How I ran my entire business from the back of an Uber using Openclaw, how we've scaled without scaling headcount thanks to a $40K/month Claude bill.

Spotify / Apple Podcasts / YouTube

Bread and Butter Collective with my old boss from my barista days, Sam Jones: Why I started buying Victoria restaurants, how slow permitting is stifling Victoria, and the paradox of entrepreneurship.

Part 1: Spotify / Apple Podcasts / YouTube Part 2: Spotify / Apple Podcasts / YouTube

"You only have 18 summers with your kids."

A friend of mine is fond of saying this. And every time I hear it, my stomach turns.

What's scarier is that your kids only really want to hang out with you until they're 14 or so, so the last four of those summers, they'll be sulking (or off in the woods smoking pot).

If you're a long-time reader, you'll know I like to build systems around my social life.

Last year, I started Camp Dad with a half dozen pals to help ensure me and my boys build some core summer memories.

TLDR: me and a bunch of Dad friends rent cabins together somewhere beautiful.

The Dads hang out and the kids run around in a pack going wild. And I delegate all the annoying logistics: food, activities, lifeguards — everything sorted so we can just relax in nature with the kids.

We did the first one last year and it was the highlight of my summer. The boys are obsessed. At least once a week, one of them asks me when we're going to Camp Dad.

This year, we're doing it August 24-28th at Sunriver Resort in Oregon, and it's going to be awesome.

I'm trying to keep it intimate. Less than 20 Dads, but I wanted to open it up to a few of you.

If you're interested, you can apply here.

I've mostly stopped listening to podcasts.

I've discovered something better: making my own.

Here's the workflow:

• I take some piece of long-form content I want to digest — a 3-hour YouTube interview I'll never have time for, a 100-page ChatGPT Deep Research report on a health topic I'm interested in, and my favorite: a full PDF of a book that I want to read but will never have the patience to sit through.
• I dump it into NotebookLM (PDF, YouTube Link, or you can even just paste in raw text)
• Hit "Generate Audio Overview"
• 10 minutes later I have a custom 30-60 minute two-host podcast on exactly the thing I wanted to know. It even lets you specify which topics to focus on.

It's like a private podcast that's 100% calibrated to my interests.

Now I've taken one step further.

I built an automation that ingests every email newsletter that comes into my inbox each morning, uses AI to write a full script for a short 10-15 min briefing, then runs it through Gemini's text-to-speech API, and produces a custom podcast of the most interesting stories.

I've formatted it to sound like The Daily, and the result is eerily close. I've also prompted it to skip anything that isn't about my hometown, my businesses, or my specific interests — and to leave out anything that would just stress me out for no reason (will not affect me).

So good!

My bed cured my acid reflux?

My friend Matteo, the founder of EightSleep, recently sent me the fancy new Pod 5 Ultra to try out.

Among its many absurd features (cooled pillows and blanket, snoring detection, vibration alarm, sleep tracking) is the one I didn't know I needed: a motorized platform that goes under the mattress and allows you to tilt your bed.

For most of my life, if I eat within 4 hours of bedtime, I've struggled with acid reflux. That nasty feeling of stomach acid creeping into my throat at 3am, then waking up with a hoarse throat.

I've tried everything from PPIs, to awkwardly propping myself up with pillows at weird angles, but ultimately given up and just forced myself to eat early.

With this newfangled bed, I researched the perfect angle (6 degrees, me and Zoe don't even notice it) to avoid reflux, and boom, magic! No reflux.

I still try to avoid eating before bed, but after those unavoidable late dinners, I no longer have to worry about it.

It always makes me happy when somebody smart dedicates their life to creating an incredible product in a particularly boring but important niche. Thank you, Matteo!

Go check it out here.

We have $70 million of recurring revenue.

A couple weeks ago, we announced that Jordan Taub is stepping down and Austin Singhera is taking over as CEO of Tiny. Q1 results came out alongside.

On the leadership front.

Over the past few years, we explored taking Tiny in a more centralized direction — trying to get the subsidiaries rowing together and centralizing shared costs.

It's a tempting idea: we spend so much money on the same services across the businesses, why not combine them into a single team at head office?

Many grizzled conglomerateurs grabbed us by the lapels and told us not to try it. I wish we'd listened.

After a lot of diligent experimentation, we've realized that the best version of this company is the old, decentralized one — and that means a different operator for the next chapter.

Enter Austin Singhera. He's been at Tiny since 2020 and has long been our most trusted thought partner and fellow shareholder. Our top-performing assets — Letterboxd, Mateina, Serato, and MediaNet — were acquisitions he championed.

He's also been waving the flag on AI harder than anyone internally for the last two years, and importantly, always puts his personal money where his mouth is, buying stock and creating alignment with shareholders.

He's the right CEO for this new era, and I'm excited to have him step up.

Chris and I are also getting more active. As I put it in the release, this is founder mode. We are taking on more aggressive involvement in investment selection, implementing AI, and measuring results. With everything happening in the world of AI, we are leaning into it.

Speaking of which, we just announced that Tiny's annual recurring revenue is now $70 million…

Pinch me. I feel like my entire mission in (business) life has been to get predictable revenue and it's finally arrived.

A few highlights from Q1 2026:

• Annual recurring revenue is now $70.5M (+80% year over year), largely driven by our acquisition of Serato in 2025. Our revenue base is getting dramatically stickier.
• Letterboxd now has 29 million users — up 175% since we acquired it. Time even named it one of the 100 Most Influential Companies of 2026.
• AI is bifurcating our portfolio in real time. Metalab is winning — current clients include IBM, ServiceNow, Intuit, and EA. Everyone needs help moving into an AI-native world. Some of our other businesses, particularly Creative Market and WeCommerce, are under fire from AI-generated alternatives.

Full details here.

It's a fascinating time to run a business: it's never been easier to start one, and yet more difficult to maintain a competitive advantage.

Random stuff:

• I take testosterone (TRT). It has made a huge difference in my mood, workouts, and general health.

But I had a thought the other day: when you inject testosterone, your body stops producing it.

So if an emergency ever happens and there's chaos in the streets (pharmacies are shut down), all of us TRT-heads will suddenly become low-testosterone beta males when we most need to be alpha and protect our families 😂

PS: on anything hormone related, I highly recommend my incredible doctor, Dr. Kyle Gillett. He has a great episode with Huberman on the topic, if you're curious.

• I watched a video that has been playing over and over in my head. I absolutely loved this 3-minute Alan Watts clip about living life the same way you'd play music.

"Existence, the physical universe, is basically playful. There is no necessity for it whatsoever. It isn't going anywhere — it doesn't have some destination that it ought to arrive at."

The line about waking up at 40 and not feeling any different from how you always felt got me. Worth three minutes.

• You stink. Here's a solution. I randomly discovered Nala Care deodorant and I love it. No affiliation — a friend just texted it to me. But I love how it smells, and the aesthetics are dialled. Go check it out.
• Ramp is incredible and now it's in Canada. If you're a business owner running corporate credit cards on anything else, you're a fool. Sign up here.
• Jeffrey Epstein: The Movie. I was shocked that they made a Michael Jackson biopic that made absolutely zero mention of the (mountains of) evidence he molested children. I can't wait for the Jeffrey Epstein biopic that tells the heartwarming story of a zany young calculus teacher who left to pursue a career in finance to fund philanthropy and leaves out the underage sex trafficking. I love Thriller too, but how is this ok???
• Slide into my DMs. I've been posting more on Instagram lately. Follow me.

Victoria stuff:

• I hate going to the mechanic. I recently needed an annoying trailer hitch put on my car and was going to have to leave my car there all afternoon.

Instead, I found this awesome mobile mechanic called Forzaa who comes right to your driveway. Super convenient.

• I also hate going to the car wash. I love Canine Car Care's mobile detailing service.

Not only do they come to you, but they don't use all the brain cell destroying nasty toxic chemicals all the other detailing services use.

New car smell = 1-5 IQ points off your kids for life.

• I have some F&B / retail / office space coming available in Cadboro Bay village in a building I own.

Some VERY cool businesses are going into the building, but I have space for one more.

Close to Oak Bay, Uplands, and UVIC — a massively under-utilized area. Email Ben if you've got a business that needs space.