Playing to Win

What's worth it?

For decades, venture has been a hard game to win, but at least it had decipherable rules:

Build a great product. Gain distribution. Raise capital. Scale.

But today, those rules are dissolving in real time.

In the last year alone, we’ve seen startup companies go from $0 to $100 million in months — only to face existential threats months later when OpenAI ships a feature. Reliable distribution channels — Meta, TikTok, Google — change algorithms on a whim, and vaporize companies’ customer acquisition strategies overnight. Companies reach $10M, $30M, $50M ARR… and then AI arrives, and suddenly none of it is defensible.

What used to take quarters now takes weeks.

What used to take weeks now takes minutes.

The scale for winning outcomes has graduated from “Bs” to now “Ts” ($ trillions:)

This isn’t incremental change. It’s a complete upending of the game.

In fact, it begs the question:

What game are we even playing?

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The Survival Trap

Many founders today have good businesses. Real customers. Real revenue. Real problems being solved.

But they were built for a different game.

If they aren’t “AI companies,” they struggle to get funded.

If they pivot, they drown in noise.

So the natural instinct is survival: get to profitability, reduce burn, control destiny.

Survival is necessary. But survival is not a strategy.

If you were starting today — in this market, with this technology — would you build the same company?

That question forces clarity: are you protecting yesterday’s moat, or building tomorrow’s engine?

Profitability matters. Agency matters. But profitability in service of what? If AI reshapes the problem itself, optimizing the old solution is just refining a horse carriage while the runway is being built.

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What Playing to Win Means

Playing to win means having the courage to go back to the beginning.

What was the real human problem we set out to solve?

Does it still matter?

How does AI change it?

If I were starting from zero today, what would I build?

This is not incrementalism. It is re-founding your company, in public.

It means underwriting adaptability over static traction. Learning velocity over last quarter’s ARR.

Because ARR is backward-looking. Adaptability is forward-looking.

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Never Run the Same Play Twice

In the book Legacy, James Kerr describes the winning discipline of the New Zealand All Blacks: never run the same play twice.

If it worked once, it won’t work again.

But most organizations institutionalize success. They protect the playbook. That’s precisely when they become vulnerable.

The best companies I’ve partnered with share one defining trait: obsessive intimacy with their customer. They read the ripples before the wave forms. They build before the need is obvious. They shape behavior instead of reacting to it.

By the time competitors respond, they’re already on their next move.

Being first means sometimes missing. But iteration compounds. The muscle of sensing and adapting becomes the moat.

Because being reactive guarantees you’re one step behind.

Winning requires a beginner’s mindset.

And once you win, you of course become the target.

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What’s Worth Winning

There seem to be endless ways to make money in venture right now.

But for me, figuring out what game is worth winning is different.

The fight for knowledge.

For agency.

For financial freedom.

For proactive, personalized health.

For reskilling a generation into purposeful work.

AI will automate jobs. But it can also unlock entrepreneurship, creativity, education tailored to every learner, healthcare that is precise instead of blunt.

Winning isn’t about valuation.

It’s about expanding human capability faster than we displace it.

The game has changed. The pace has accelerated. The old plays won’t save us.

So the question isn’t whether you’re surviving.

It’s whether you’re playing to win —

and whether the game you’re playing is worth winning at all.

As for me, the only thing more urgent than winning this new game is shaping how it’s played. We need more clear voices at the table. More diverse perspectives guiding the rules. More long-term thinking about the systems we’re building.

There is a version of the future that is brighter than this moment feels.

But it won’t happen by accident.

It will require more of us to gear up and lean in.

It’s game on.