The newsletter

I lied to my kids...

The September 2026 Friends Newsletter: what I’m thinking about, recommendations, and updates.

11 min readSeptember 8, 2026

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).

✈️ Toronto friends: let's hang out!

I'll be in Toronto September 10–15 for TIFF and would love to hang out.

I'm getting readers together for a coffee meetup on Monday, September 14 at 3pm at NEO Coffee Bar, 61 Spadina Avenue. You can RSVP here.

🙏 PS: If you have extra TIFF tickets to something amazing, I'd love to buy them. Also curious about parties, screenings, and other events I should be going to: please tell me what I should check out!

Here's what I'm thinking about…

You should lie to your kids.

When I was a kid, I hated wearing a bike helmet.

My mom and I argued about it constantly. I thought it looked stupid and mussed up my hair.

Eventually, my dad sat me down and told me about two boys he'd grown up with. Twins named Ted and Tom.

Ted always wore a helmet. Tom didn't, because he preferred to look cool.

One evening, their mom rang the dinner bell.

Ted came home.

Tom didn't.

Their mom got in the car and drove around looking for him.

She found him in a ditch. He'd crashed his bike and hit his head. My dad told me the accident had left him with permanent brain damage, and that he now used a wheelchair.

That was the end of the helmet argument.

I wore one from then on, and still always get on friends' cases for not wearing them.

About two years ago, I told my sons a lie.

They were complaining about what we were serving them for dinner.

So I lied to them.

I told them I had just read about a new scientific study that showed that children's taste buds change every two weeks.

I told them if they didn't like the food, fine. But we'd try it again in two weeks, once they had new taste buds.

It worked perfectly.

I'd give them the same food a few weeks later and their eyes would go wide.

“Oh my God, my taste buds have changed, Dad!”

They were amazed.

I'd made up the two-week rule. But it gave them a reason to try something they were convinced they hated.

Then I remembered Ted and Tom.

Twin boys. One wears a helmet. The other doesn't because of his hair, and ends up in a wheelchair.

Exactly the story you'd tell a kid who thought helmets looked stupid.

I called my dad.

He laughed and told me that it wasn't true.

But it worked. He told me a lie that may have prevented me from getting brain damage.

So...maybe lying to your kids isn't so bad.

Frank Sinatra was a massive jerk.

I absolutely died laughing at Mike Birbiglia telling John Mulaney this Frank Sinatra story. It's pure gold. Must watch (1 minute).

Speaking of Sinatra, I'm about halfway through Frank: The Voice, the first half of James Kaplan's enormous two-part biography. I'm loving it. So many amazing stories about old Hollywood, music, and people behaving terribly.

You hate people who eat your pie.

Another tech entrepreneur started blowing up on Twitter around the same time I did.

Our businesses were very similar, and I started comparing our follower counts.

Every fiber of my being wanted to hate him.

He hadn't done anything to me. I barely knew him. But he was doing the same thing I was doing.

I was caught in mimetic competition.

Every time I'd read one of his tweets, which often got slightly more likes than my own, I'd grit my teeth and think about how smarmy he was.

What's ironic is that we eventually met. Ate a few meals together. Became friends.

Of course, he was wonderful. Kind, and very similar to me. Exactly the sort of person I'd normally want to be friends with.

But because he was so similar to me—because we were competitors—I wanted to hate him.

I've thought about this a lot since.

We all have an incentive to dislike people we consider competitors for all sorts of things.

Money. Followers. Attention. Friends. Romantic partners.

Anyone who eats our pie.

It's a helpful psychological trick our brains play on us.

If we can convince ourselves they're assholes, we don't have to feel quite so bad about them doing well. It's ego protection.

It also makes it feel okay to ruthlessly compete with them. To swipe out their legs and throw sand in their eyes.

We've decided a certain amount of the pie belongs to us. So when someone doing something similar gets a bigger slice, it feels like they've taken some of ours.

Even when they haven't.

His Twitter followers weren't being deducted from my account. But I hated him anyway.

And it works in the other direction too.

Imagine you're interviewing someone for a job. They've read up on the company and want to hear how you built it. You start telling a story, and they're hanging on every word. They laugh at the bit you thought was funny.

By the end, you're thinking: I really like this person.

Of course you do. You just spent an hour feeling interesting.

And from their side, you could give them a job. Teach them how to do something they've been trying to figure out. They have every reason to be interested in you.

Neither of you has to be pretending. There's a good reason for both of you to come away thinking the other person is great.

And, of course, fail to give them the job? They'll hate you. You took their pie.

I've started to think that a lot of the people I dislike are simply people I have an incentive to dislike.

Meanwhile, I'm much more generous with someone who makes me feel liked.

The question to ask yourself whenever you're finding someone infuriating:

"Do I have an incentive to dislike them?"

All too often, the answer is yes.

Let’s have a VERY expensive lunch.

I'm auctioning off my annual charity lunch with my business partner, Chris Sparling.

Chris and I will spend a few hours with you helping with whatever you need and telling you whatever you want to know.

The money will support the work we do at Tiny Foundation.

If you'd like to bid, email me your offer by September 20th.

Minimum bid is $10,000 (the last one went for over $100k 👀).

Wanted: a boring business.

My friend Jade Sprake built and ran a handyman business. Now she's looking for an established home-services or industrial business to buy, and we're backing her.

If you own one, or know someone who does, email Jade.

You can read more about what she's looking for here.

Don't start a business.

Don’t start a business unless it's the only option.

To be an entrepreneur, you have to be unemployable.

The idea of working for someone else? Impossible.

Being told what to do makes you want to scream.

You’ve wanted to shove every boss or authority figure in your life aside and grab the wheel.

You’re overflowing with ideas on how to improve things.

You're perpetually dissatisfied with everything.

In short: you're just the right amount of broken.

You don’t want to start a company. You need to.

Why else would you endure the endless struggle and misery?

The sleepless nights. Missed payrolls. Lawsuits. Betrayals.

People misunderstanding you and thinking you’re crazy.

Like Andy Dufresne, crawling through the tunnel of shit to reach freedom.

You only do it because there’s no other way.

I bought a second Picasso.

The stock-market version.

A while ago, I described my investment in IREN as finding a Picasso at a garage sale. Something valuable sitting in a place people weren't looking.

I've made a similar bet on New Era Energy ($NUAI), a former helium company developing AI data centers in Texas.

AI needs enormous amounts of electricity. New Era is trying to build data centers that can generate power on-site using natural gas. My bet is that its sites become much more valuable if it can get the projects built and leased.

There's a huge gap between a promising site and a functioning data center. This is a speculative investment. I own shares and could lose money.

If you're curious, I wrote up the full thesis here.

A few recent discoveries I love:

Screenshots that don't suck.

You know that little thumbnail that appears when you take a screenshot on your Mac, then disappears just as you're about to drag it somewhere?

I recently discovered CleanShot. It keeps screenshots handy while you decide what to do with them. Drag one into another app, add an arrow, blur something, or keep it floating on your screen.

If you're vibe coding and sending screenshots back and forth all day, this is a game changer.
Weird mints that stick to your gums.

One annoying side effect of my ADHD medication is dry mouth. I found XyliMelts to help with that, but now I mostly love them because they're a better mint.

I've always hated the usual ones. Most are full of sugar, and I inevitably chew them in thirty seconds.

These little sugar-free discs stick to your gums and slowly dissolve. I get about an hour of minty goodness.

My favorites are the Mild Mint ones.
Hate messy cables?

I've been using Lamicall's spring-loaded cable clips on kitchen islands, bedside tables, and lamp cords. Anywhere a cable keeps sliding away. Open the little clip, put the cable in, and it stays where you left it. I love them.

Lamicall cable clips: US / Canada
Insanely good sparkling water.

Some of you will remember that I couldn't burp.

Yes, really. It's a condition called retrograde cricopharyngeal dysfunction, and I got surgery to treat it and am happy to report that I can now burp.

I've since developed a sparkling-water habit and my current favorite is Le Seltzer, a little family-run company out of Montréal.

I especially love the Amaro, Fig Bergamot, and Ginger.
A beautiful mini fridge.

I bought a green Rocco for my office and it's gorgeous. I love when somebody takes something ugly (like a mini fridge) and makes it beautiful.

It has smart features, which I probably don't need. They've also introduced a simpler, less expensive model called The Essential.
Renting cars sucks.

I've been using Turo on my last few trips, and I can't believe how much more pleasant it is than the usual rental-car routine.

It's basically Airbnb for cars. You choose the actual car, arrange pickup through the app, and skip the rental counter.

Pickup depends on the host and airport, but my experience has been amazing.
A weird little gadget for mosquito bites.

This Beurer BR90 has been miraculous for me. You hold its little heated tip against a mosquito bite for a few seconds, and, for me, the itch doesn't come back.
The best sleep supplement I've tried.

Eight Sleep now makes a Jet Lag supplement, and I've been surprised by how much it's helped me sleep.

It combines melatonin and phosphatidylserine. I've taken those separately without the same result, so I can't tell you why this particular formula seems to work so well for me.

Eight Sleep says it's for occasional travel use, rather than a nightly, long-term sleep aid. It's currently sold only in the contiguous US.
A massive home theater upgrade.

I have a pretty fancy home theater. Projector, Dolby Atmos, all the bells and whistles. But I'd watch a movie and wonder why it didn't sound the way it did in a theater.

I kept calibrating the speakers over and over again. Same issue.

Then I got a Kaleidescape.

It's a dedicated movie system. You buy or rent a film, download it in very high quality, then watch it. Think 100 gigabyte files. Full resolution 4K and lossless sound.

The movies I was streaming on my Apple TV looked pretty good, but streaming usually throws away some audio detail to keep the file smaller. Kaleidescape offers lossless sound, like a good Blu-ray. It's a lot more data, which is why you download the movie first.

I cannot believe how much better my theater sounds now.

The interface drives me crazy, and the hardware is absurdly expensive. I'm enjoying movies so much more that I don't care.

Friend Brag: Rob Fraser.

My friend Rob Fraser has spent years obsessing over socks. I'm a longtime investor in his company, Outway, and one of my favourite things he's built is Custom Lab.

They make custom socks for companies, conferences, and teams.

Which doesn't sound particularly exciting until you think about how much corporate swag exists purely to put a logo on something.

Rob cares about the actual sock. Custom Lab uses Outway's materials and manufacturing expertise, so you're starting with something people would want to wear even without your company name on it.

And they design the whole sock from scratch. You can send them a logo or a rough idea, and their designers will help you figure it out. The design work is free, including revisions. They can do everything from performance socks to merino or dress socks, depending on who you're making them for.

I love the attention to something most people would barely think about.

If you're ordering something for your team or an event, take a look or email them here.

Random stuff.

I couldn't relax for decades.

I have never heard the feeling I lived with for so long explained more clearly than in this video from Dr. K.

That sense that something is about to go wrong, even when everything is fine. That you've forgotten something, and if you let your guard down, you'll find out what it was.

If that sounds familiar, or you've been wondering about ADHD and anxiety, give it fifteen minutes. I wish I'd seen it years ago. PS: If you think you might have ADHD, my personality test Deep Personality now screens for it.
Ace.

I'm a big Madison Cunningham fan, but I won't lie: her latest album, Ace, didn't quite click for me at first.

Then she played at my Interesting People event, and something changed. I've been listening to it constantly for the last few weeks.

It's about the end of her marriage and what comes after. Give it some time. I'm completely hooked.

Spotify / Apple Music
Blue.

Joni Mitchell's Blue 50 (Demos & Outtakes) is so beautiful. Five demos and outtakes from Blue. I especially love the demo of “A Case of You.”

Spotify / Apple Music

Victoria stuff.

Tasting Victoria just posted a great roundup of all the new spots opening in Victoria.
Faye's Spa, in the Bay Centre, is amazing for a quick chair massage or a longer one lying down. Just walk in.

I've had some absolutely amazing massages there in the time it would usually take me to get settled at a hotel spa.
Vic Builds. I run Entrepreneurs Lunch Club, but my friend Sam Games has built a great group for younger, up-and-coming entrepreneurs here in Victoria called Victoria Builds.

I've spoken to the group and gone to their dinners, and I've really enjoyed it. If you're young and building something exciting, you should go.
Got a couch to sell? At Victoria Builds, I met a guy named Elwyn Thom who runs Recertified Furniture.

If you have a nice brand-name couch, his team can handle pickup, cleaning, and selling it for you. It's such a simple, efficient business. I love it.

Elwyn is a very cool guy, and his Instagram is a fun follow.

If you've got a couch to sell, send it his way.
HVAC that looks beautiful.

A young entrepreneur named Liam Quayle reached out to me after buying a local heating and cooling business called ExchangEnergy.

We hit it off, and I happened to need a bunch of work done.

I hired his team and have been blown away by the quality and service.

I'm a big fan of the Quilt units they installed. Attractive wall units, a nice little light, beautiful controllers, and an app that feels like someone thought about it.

If you need heating or cooling work on the Island, I highly recommend Liam and his team.