Aug 30, 2025 Dear Leon,
You arrived on a Saturday in Lourinhã, Portugal. I held you for the first time and immediately thought, "Oh, so THIS is what everyone was talking about."
I'd spent 20+ years building weird businesses on the internet. I'd had six legal last names. I'd worn t-shirts for a living, auctioned off my identity, sold my entire future (twice), written books no one asked for, moved across the world, and somehow convinced your mom to marry me through the whole thing.
But holding you? That was the first time I thought: okay, none of that other stuff mattered nearly as much as I thought it did.
Here's what I want you to know:
You don't have to figure it out early. I didn't start my first real business until I was 26. Before that, I sold pagers, flipped phones on eBay, got fired from a coffee company for bad Photoshop work, and started a design firm with zero clients. The path is the path. Even the weird parts. Especially the weird parts.
Try the things that sound ridiculous. I wore t-shirts on camera every day for five years because it sounded too stupid NOT to try. That "stupid" idea led to the Today Show, Forbes, the New York Times, and over a million dollars in revenue. It also led to $100K in debt. Both of those things were valuable. (The debt less so, if I'm being honest.)
Your name is not an accident. You're named after AJ Leon — a friend who created an event in Fargo, North Dakota called Misfit Con, where I stood on a stage and was more vulnerable than I'd ever been. That moment cracked me open. Your name carries that energy: the courage to be honest about who you are, even when it's scary.
Your mom is the best person I know. She DM'd me on Twitter in 2010. She's been my partner in every business, every move, every wild idea since. She's the reason any of this works. She's the reason YOU work. (She did most of the heavy lifting on that last part. Literally.)
You don't have to do what I did. You don't have to be an entrepreneur. You don't have to build things on the internet. You don't have to have six last names (though, fair warning, you might end up with at least a couple). You just have to be curious, be kind, and be willing to try things that might not work.
The world will tell you to be normal. I've spent my entire career ignoring that advice. Some of the time it cost me. Most of the time it was the best decision I ever made. You get to decide which voice to listen to. I'll be here either way — probably wearing a weird shirt.
You were born in a small Portuguese town, to two Americans who sold everything they owned (twice) to chase a life that felt right instead of one that looked right. That's your origin story. It's a pretty good one.
I love you more than I thought was possible. And I thought I knew what "a lot" felt like. I did not.
Dad
written March 2026, when you were 6 months old and had more hair than me
The whole crew If this letter made you feel something, imagine three emails a week.
Weird ideas, real stories, and the occasional dad dispatch.