How I succeed by starting companies that (mostly) fail.

Hello friend,

Here's what I'm thinking about…

How to succeed by failing (over and over again).

I've started over a dozen companies. I'm not bragging—most of them have failed. Roughly a 40% success rate with 60% failure. The list is a graveyard, basically the world's most stressful real-world MBA.

But fortunately, when you average it all out, I've won. After twenty years of trial, error, and chaos, here's the recipe I keep coming back to: a simple model, low competition, an obvious need, the right co-founder, the visionary-integrator pair, and the right incentives…

Read the full essay →

Single parenting is brutally hard. Emotionally, financially, and physically.

Doing it while trying to make ends meet can feel impossible. I have insane respect for anyone who pulls it off.

Since 2023, Zoe and I have been proud to support 1Up Single Parent Resource Centre here in Victoria, an incredible organization that helps solo parents with food, legal support, and community when they need it most.

Right now, they're running a fundraiser — and we're matching every donation, dollar for dollar, up to $25,000.

That means your $25 becomes $50.

Your $100 becomes $200.

And together, we make life a little easier for families doing it alone.

If this newsletter has ever made you think, smile, or learn something new, pay it forward here.

Donate Here - we really appreciate your support.

PS: If anyone donates $25,000 USD or more, I'll happily take you out for lunch and do whatever I can to help you or your business.

Typing is slow.

I've been using WisprFlow to dictate all my text messages and it's unbelievably good. You just tap a little mic icon on your keyboard and talk instead of tapping out texts. Highly recommend.

I bought inflatable pants.

I play a lot of tennis and pickleball and my legs are constantly sore. My friend Rob recently recommended these really dumb looking inflatable pants, the Hyperice Normatec 3.

Basically, you put these silly things on your legs, connect them to this little pump unit, and then it inflates them. They're SUPER tight and they basically massage your legs for an hour. It feels amazing and is very relaxing.

I don't know if there's any solid science behind them, but I will say I've worn them almost every day since I bought them and I feel like my leg soreness has improved.

Plus, you look cool as hell.

Check them out here

Lately, I've been letting people down.

And I'm absolutely loving it.

In my last email, I talked about The Courage To Be Disliked. The idea that if you try to please everyone, you'll live an inauthentic and miserable life.

I realized that, in an effort to not upset people, I have a habit of overcommitting. I say yes to too many things months out, then wake up and groan when I look at my calendar and realize that I have to spend my day doing things I don't want to do...

Read the full essay →

Aritzia, but for men.

I never understood Aritzia. Every woman I've ever met is obsessed with their clothing, and whenever I ask why they say something like "they just…get it." Over time I gleaned that Aritzia had nailed a trifecta of qualities: on trend, affordable, and comfortable.

Now Aritzia has their own men's clothing brand. A few years ago, they bought Reigning Champ, and I have to say, they've really got it dialed. I would say that at least 70% of my new clothing is RC, and they have once again nailed the trifecta, but this time for men.

Very nice.

Website

That's all for now…

-Andrew