Have babies with the wrong person…

Hello friend,

Why you're getting this: this is my Friends Newsletter, a brain dump of interesting things that I send to interesting people I've met and friends I want to stay in touch with. Zero pressure to stick around — just click unsubscribe if you don't want to get it (don't worry, I won't be notified).

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.

For most of the 9 months before her birth, I was stressing about it.

The thought running on loop:

All I want is freedom, and here I am building a baby jail for myself.

I was ready to travel. Wander. Go crazy. Stop being so responsible.

I could be dead in 40 years, for Christ's sake!

A third kid made logical sense, but the logistics themselves seemed nightmarish.

And then I held her and my concerns disappeared.

The treasure I was seeking was in the cave I was afraid to enter.

Imagine if you met someone who said, "I love cooking. But I have no interest in tasting the food I make. Not even a bite."

You'd think they'd lost their goddamned mind.

Sure, cooking itself is enjoyable.

The tap tap tap of the knife on the cutting board.

The smell of garlic catching oil.

The sizzle of a deglazing pot.

But the greatest joy isn't the cooking. It's getting to enjoy the meal you created from a mishmash of ingredients that came together perfectly.

Sitting down with your family. Hearing the collective "Mmmmms."

This is what young people are doing with sex.

I know that sounds weird, but bear with me here.

When you're young, without thinking about it, you obsess over two things:

1. Looking attractive.

2. Generating status.

You want to be fit, hot, and successful.

You want to look like someone worth mating with. Almost all of it is subconscious.

Men do shoulder presses to widen their shoulders.

They buy expensive watches and luxury cars to awkwardly signal success and resources.

They lie about their height on dating apps and overstate their salaries.

On the flip side, women starve themselves to fit into smaller jeans.

They obsess over hair and skincare, and do squats to perfect their hip-to-waist ratios.

All of it is to advertise one of two things: good genes or good resources.

What drives this behavior? The science is pretty definitive:

Across ​37 cultures​, women rate ambition, height, and earning power as the top traits in a man. They ​want their men 8 inches taller than them​, and ​to out-earn them​ — a preference that holds even as women's earning power catches up.

Men, in the meantime, from age 25 to 85, ​converge on the exact same hourglass shape​ as most attractive — a waist-to-hip ratio of 0.7. The same number in every country on earth.

Both sexes obsess over skin so deeply that when ​researchers showed people a postage-stamp patch of cheek skin​ with no other features visible, the rating of that tiny patch alone predicted the rating of the whole face.

Why does skin matter so much? Because clear skin signals a strong immune system — and a strong immune system signals three things at once:

1. You'll live long enough to raise a child.

2. You'll pass strong immunity to that child.

3. You're less likely to transmit disease to a partner.

We don't think about it consciously. Our bodies just instinctively know.

All of this effort — from shoulder presses to Rolexes to the $300/mo skincare routine — points at the same biological outcome:

To be sexually attractive = to be fit for mating.

Our bodies are screaming something at us over and over again:

Make a healthy baby!

The cooking, the spice, the chemistry, the chase — all of it is just prep work. Mise en place.

The meal, the final stage, the thing that delivers the payoff, is the child.

And yet, young people these days are obsessed with the prep but refusing to eat. Fewer and fewer of them seem to want to have children of their own.

The usual arguments:

"I'd rather focus on my career"
"I want to travel"
"It's expensive"

And what are they getting in exchange for this freedom?

Misery. Loneliness. Antidepressants for breakfast.

The ​default state of most people is alone in a room watching strangers on a phone​.

Their bellies are full of the optionality they thought they wanted. They are master chefs starving at their own counters, packed with food they won't eat.

Why? Because you might care about freedom, but your biology doesn't.

When I was still married to my first wife, there was a family tradition of eating dinner at her grandmother's every Friday night.

She was in her 90s by this point, and she'd had her first kid in her early twenties and just kept going, ultimately having five children who all went on to have children and grandchildren of their own.

Her house was always buzzing with dozens of family members. Three generations of people who came from her womb, ranging from tiny babies to sulking teenagers to fifty-year-olds.

While everyone bounced around her, filling plates of food, comforting crying babies, and trying to herd the pack of children, she'd just sit watching the scene in a big cushy chair in the corner with a serene smile.

I'd never seen someone look so deeply calm and satisfied.

It seemed odd to my twenty-seven-year-old self. The one who was obsessed with building a business and making something of myself.

Here was an old lady, happier than I'd ever been, watching a bunch of stinky kids run around.

She hadn't built a Fortune 500 company or won a gold medal at the Olympics.

She hadn't traveled the world or climbed mountains.

Instead, she just raised a bunch of kids.

But when I had my first son at 31, I suddenly understood her smile.

My first thought upon having kids was that I wished I'd done it younger.

That I hadn't delayed this wonderful feeling for so many years in my mid to late twenties, chasing late nights and exotic trips that never delivered the hit I wanted.

Where I used to be jealous of people who were more successful than me, now I was jealous of people who had kids in their twenties.

People who would get to know their great-grandchildren.

This is why you should have kids as young as possible with the wrong person.

Not a cruel person, not someone who'd be a shitty parent, not a stranger you met on Tinder who has a weird katana collection.

I mean: the not-quite-right one.

The one your friends say is "great but…"

The one who'd be a good Dad or Mom, but isn't the soulmate you were promised.

After all, as I've written about, ​I got divorced​.

Do I regret having kids? Not for a second.

My kids are the biggest win of my entire life.

The relationship doesn't have to last in order for the kids to be worth it.

Babies hit a part of your brain nothing else can reach.

It's biology. Every other thing in your body works this way.

You have a craving, and when you satisfy it, you feel good.

Eating when you're hungry.
Sleeping when you're tired.
Sex when you're horny.
Hanging with your friends when you're lonely.
Going for a run after a week sitting still.

Why would the biggest drive — the one our entire biology is organized around — be any different?

It isn't.

Last week, I had one of those days.

The kind where it feels like your head is a pressure cooker that's moments away from exploding.

Not enough sleep.
Too many texts.
Too many emails.
Too many household tasks I'd forgotten about.

I felt like if one more person asked me for one more thing, I was going to fucking blow.

I was dreading bedtime with the boys.

They were screaming. Running. Getting water all over the bathroom floor and shrieking.

I managed to hold it together.

I got them into the bath. Brushed their teeth. Tucked them into bed. Turned out the lights.

Then my 6-year-old rolled over, pushed his forehead into my chest, and let out a long sigh and sank into me.

I could feel his heartbeat through his pajamas, and within a minute he was conked out, snoring on me.

And suddenly — bizarrely — all was right in the world.

No drugs. No therapy. Just a small person who needed me.

It's the ultimate shortcut. Easier than climbing a mountain, building a company, or the other absurd things people do to fill that cup.

No amount of trips to Bali, writing workshops, or run clubs can fill it.

Only babies.

This post might piss you off.

Maybe you can't have kids. Maybe you flat out reject my pseudo-Darwinian worldview.

Fair.

If that's the case, you can adapt what I'm saying into a paradox:

Meaning comes from being needed and caring for others.

Anyone who has had a dog knows this.

Having a dog logistically blows — you're home by 5pm to feed them, walking them at 7-8pm, dropping mountains of cash at the vet at random. And yet, existential satisfaction washes over you.

But imagine TikTok influencers claiming society tricked us into getting dogs to steal our freedom (as they do about having children).

People would LOSE it. They'd be outraged.

Because while owning a dog objectively makes life worse, it subjectively makes you happier.

Any dog owner will tell you this.

And it's like that with kids, times a thousand. The data backs this up.

Two researchers at UC Riverside ran ​a study in 2013​. Across all measures, parents reported more positive emotion and more meaning than non-parents. And they reported feeling more positive while caring for their kids than during anything else they did.

And here's the best part:

When you measure actual, objective moment-to-moment happiness, a ​2014 study of 1.7 million Americans​ found that parents score way lower than non-parents on day-to-day satisfaction.

Parents have more of all the bad stuff.

More worry. More stress. More anger.

By every objective metric, parents' lives are harder than non-parents.

But by every subjective metric of meaning, their lives are better.

Despite all the extra stress, ​93% of American parents over 45​ say they are glad they had kids and a ​2021 survey​ found that 1 in 3 Americans wish they'd had more kids.

So should you shack up with a random and have kids?

The caveat first.

Some people are infertile or have complex health problems.

Some don't have a partner.

Some are still doing the work to be safe parents themselves.

Some really, truly just flat out don't want kids, and that's fair.

But for the rest of you — those who are on the fence, in good-enough relationships, with some financial stability, who keep telling yourselves not yet, not quite, not until I'm sure, not until that promotion:

Just have the freaking baby.

Stop waiting for the perfect person or for your apartment to be bigger.

Stop waiting for the version of yourself who has it figured out.

Because that version is never showing up.

As I'm writing this, it's early in the morning and I'm tired.

I woke up early to take the baby so Zoe could try to scrape out a few precious hours of sleep upstairs.

I'm using voice dictation in a big plush easy chair in our den, with our daughter asleep in the crook of my arm.

The top of her head smells like that smell that all babies seem to have: rose petals and chocolate.

Every minute or so she lets out a funny little gasp or hiccup as she wriggles around in her sleep. Dreaming about nipples or whatever it is newborns dream about.

The boys are joyfully beating on each other somewhere down the hall.

I keep watching her breathe and grinning like an idiot.

And I cannot, for the life of me, remember what I was afraid of.

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.

-Andrew

Want to read more? Here are a few of my best past issues:

• ​Divorce is awesome…​

• ​I lost ten million dollars doing something stupid​

• ​How I Succeed by Starting Companies That (Mostly) Fail​

• ​I committed email suicide.​

• ​You should ignore your kids.​

• Read more past issues ​here​.

Did you enjoy this newsletter? Say thanks by checking out one of my businesses:

• ​Make the perfect morning coffee using an AeroPress​

• ​Review a movie on Letterboxd​

• ​Get hyper-caffeinated on Mateina​

• ​Buy a bronze bust of Charlie Munger or Warren Buffett​

• ​Hire Metalab to design or build your next app or website​

• ​Or go check out one of our many other businesses​

Follow me on X: ​@awilkinson​
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