How I ended up on a jet ski in Nazaré

To be honest, it still feels like a dream.

All I know is this: One month after I saw the first episode of 100 Foot Wave, a documentary series following big wave surfer Garrett McNamara’s quest to surf the world’s largest wave, I was being towed on the back of a jet ski in the very spot that these big wave surfers thought the 100 foot wave was surely to come.

Why Nazaré?

Apparently Europe’s largest submarine canyon lives there, creating the biggest waves in the world—the Everest of surfing if you will.

The problem? Not only can’t I surf, I can barely swim. So why the hell would I go to the Everest of surfing? Bad idea.

On paper I went because I signed up for an activity on a conference agenda that I didn’t fully understand. But when we actually arrived at the port that morning, all but me and a VC chickened out. And for good reason! The ocean there is crazy, terrifying, and positively screams DON’T COME NEAR ME as loudly as possible. Go pet a King Cobra if you want a sense of the experience.

But “jet ski tour of Nazare” was an option on a sheet, so I said yes. And the reason I was at that conference was because I was invited to a conference in Portugal a few weeks back (a place I’d never been) and I said yes. And the reason I was invited was because I met one of the most successful entrepreneurs I’ve ever encountered recording a podcast. And the reason I recorded that podcast was because another successful entrepreneur friend introduced me to that entrepreneur. And the reason I met… you get the idea.

So by a series of saying “yes” to seemingly random and unrelated events, I found myself on a jet ski surrounded by the craziest ocean I’ve ever seen.

That’s how experiences stack up when we change our default state from “no way, that’s scary” to “Screw it, let’s do it.”

You never know where saying “yes” today will lead you tomorrow.

The 3 Body Problem and the coming AI wave

Recently, I was captivated by the Netflix series 3 Body Problem.

While the show itself is great, I found myself more intrigued by the actual problem it references.

What’s fascinating is this: when two objects in space—say, stars or planets—interact, their movement is highly predictable with our current mathematical models. We can calculate their positions eons into the future with shocking precision. That’s why we know, for instance, when the moon will rise 1,000 years from now in Tibet.

But the moment you introduce a third object, all bets are off. We lose the ability to predict or model their movements.

Why is that interesting?

Because even though we can’t use math to solve the three-body problem, it’s still 100% knowable. These celestial bodies aren’t behaving randomly. They’re following clear, immutable laws of physics. There’s nothing chaotic about their behavior—but there is something chaotic about our ability to compute it.

The tiniest rounding error—down to .0000000000000000000001%—can throw everything off. So even extreme accuracy is useless here.

It’s a paradox: something entirely logical, yet effectively unknowable. Chaotic, but not in the way we usually mean.

The three-body problem is one of the clearest examples of something in our universe that’s just beyond reach—dangling right in front of our nose, taunting us.

Will quantum computing solve problems like this? Will this be the type of problem AI cracks open?

We’re still just primates, after all.

Someone always kills the fun

I love the case study of Casper mattresses.

Red Antler created brilliant branding and campaigns for the start-up, which quickly became a unicorn.

Whimsical, off-the-wall marketing helped the young mattress company stand out on billboards and NYC subways, defining a new era of shopping.

But now?

Casper is just another bog-standard e-commerce site.

As they grew, it appears that scores of new management systematically killed all the fun that made Casper unique and great.

Rare is the company indeed that can stave off the inevitable downward force of small-minded middle managers.

The AI tool we ALL need

Alt title: My desktop is a dumpster fire.

We all know the wonders Marie Kondo can do for our physical spaces.

But how much digital junk is on our hard drives?

Files, folders, projects that we’ll never touch again, taking up our valuable digital real estate.

I’m sure someday I’ll want to re-read my college essay comparing circles in Moby Dick to triangles in The Purloined Letter. Cough.

We need AI for our hard drives, organizing, cleaning up, and categorizing our files, making it easier to find what we need and get rid of what we don't. Every OS must have this feature (but mostly just MacOS).

We need that space back.

I got to talk to 2,000 teenagers. Here’s what I said:

Thanks, Colorado FFA!

Life is full of choices. And the decision to not make a choice is itself, a choice.

The courage to be ourselves is perhaps the greatest courage of all (and the most important).

When you're stuck at a fork in the road? There's always a secret, 3rd option.

The present and the future are full of digital noise and distraction. When you believe in something strongly, it's more important than ever to tune out the noise and focus on what matters most to YOU.

Make choices so that you're happy with the story of your life at the end of it.

Just you. It's your life, no one else's. Fight for what you believe is worth fighting for.

And what did I learn?

That these kids are amazing. So passionate, so courteous, and full of great energy. The future is in good hands!