Every time Digital Native hits my inbox, I turn to Lauren and Maddi and start screaming "I WAS LITERALLY JUST SAYING THAT." They're tired of it. I'm tired of it.

So here we are. It's official. I'm throwing the whoop band gauntlet down.

He doesn't want this smoke. He also doesn't know about this smoke because he doesn't know I exist.

This is the Mad Men elevator scene except Don (Rex) is just riding down peacefully because he has no clue that Ginsburg (ya boy) is alive.

How It Started

Digital Native was one of the first VC newsletters I started reading. When I decided to start Daring Ventures, I found myself constantly forwarding his commentary to the team with “yes” / “this is good”, etc.

Then this guy shows up with Daybreak Ventures and its sweet website and clearly articulated thesis so concise you could explain to a squirrel

Meanwhile, back at Daring Ventures world HQ, we're having our 47th post-mortem on whether we should say "trust layer" or "taste infrastructure." Our eyes have been glazed for so long they've fossilized. We keep telling ourselves we're the "authentic, outsider" brand, but our copy reads like VC fanfic.

I've scaled Mount McKinsey. I've descended Mount McKinsey. I've written manifestos about taste and context and trust. I've made Kennedy-assassination-level conspiracy slides about "Human-Centric Value Creation in Relationship-Mediated Markets."

Arena vs Stands

Fans sit in the stands. Rivals stand across the court.

Even if you're losing 100-0 on a scoreboard only you can see, you're still playing. And that's better than the best seat in the house. When you declare someone your rival, you graduate from consumer to competitor. You enter the arena through sheer force of will. No invitation needed. Just a decision.

The beauty of one-sided rivalry is its purity. No politics. No actual dynamics. Rex can't psych me out or compete back. He just exists, being good at what he does.

Also This Week:

How Do You Win?

You can't. That's the point.

I'm competing with the version of myself that Rex reminds me exists.

He's not my rival. He's my Ghost of Christmas Past, showing me what authentic communication actually looks like.

He unknowingly holds up a mirror to the gap between who we said we'd be and who we've become.

You can't win a rivalry against your own North Star. That's not the point. The point is that declaring rivals is how I architect motivation without the paralysis of pure admiration. You can't chase a hero—they're too far away. 

But a rival? Even an imaginary one? You can chase a rival every single day.

Thanks for keeping us honest Rex.

Oof. I’m cooked.