The Freight Train Business

The Freight Train Business

The descent from Mount McKinsey has been rough and arduous. But now back here at sea level and brain flooded with more oxygen than buzzwords, Daring Ventures is firing on all cylinders and it hit me like a freight train. We're in the freight train business.

Not literally, although I'm sure there's a founder we NEED to meet working on that. Won't stop thinking about some issue in intermodal freight that breaks down when cargo moves to rails. Tech has built rails for this. Rails for that. What about rails for rails? Their friends and family probably wish they would stop. The founder probably wishes they could stop too. But they can't.

That's the business we're in. We back human freight trains who run on a single track, in one direction, at full speed, forever. The destination chose them five years ago when they first noticed the problem. Now they're just hauling ass toward the solution.

From PowerPoint to Plain English

We spent eight months building frameworks about "domain expertise" and "conviction bias." Made charts about "authority bottlenecks" and "trust infrastructure." The truth was simpler: we back people who physically cannot stop building their thing.

The difference between "won't stop" and "can't stop" matters. Determination wavers. Compulsion removes choice entirely. These founders stay locked on target when they hit walls because pivoting requires psychological flexibility they lack. Their brain only has room for one thing.

Acceleration, Not Empowerment

When Cam left pharma to build PraxisPro, he'd been mentally building it for over a decade. Every sales call was product research. Every frustration was a feature request. By the time he quit, the company already existed in his head.

We accelerated something already in motion. It was going to exist one way or another. We’re just helping him get there faster.

The Market Timing Gift

Five years ago, being monomaniacal about one problem was a liability. Building took forever. You needed flexibility.

Now, AI turned everyone into a builder. The bottleneck moved from building ability to knowing what should exist. Monomaniacal founders already know. They've lived with their problem so long that the solution feels obvious to them and remains invisible to everyone else.

Why We Started This Fund

WACC taught me something crucial: the kids washing cars at Enterprise had the same raw capability as the ones at Goldman. They had the hunger. The ability to work eighteen-hour days on pure will. They just lacked the playbook.

But the ones who made it through had something specific. They couldn't accept the world as it was. They'd fail three times and come back for a fourth. They'd get rejected from every bank and build their own path. That relentless, locked-in focus on proving something that shouldn't need proving.

We built Daring Ventures without asking anyone's permission. No LPs committed. No proof it would work. Just the single-minded focus that this fund needed to exist. The irony kills me: we spent months trying to sound sophisticated when the truth was simple. We knew it from day one. We just needed permission to say it out loud.

The Diligence Reality

We absolutely care about TAM. We run models. We validate markets. But we ask questions in a specific order. First: are they monomaniacal? Second: is the problem real? Third: is the market big enough?

Most VCs start with TAM and work backwards. We start with founders who cannot stop building and validate that their obsession maps to opportunity. When someone spends five years unable to stop thinking about a problem, there's usually a reason. The TAM tends to exist. They just describe it differently than MBAs would.

The Recognition

If you've been building the same thing in your head for years, if you left comfort to fix that one thing that drives you insane, if success made the obsession worse, you're inevitable.

We recognize that you're going to build anyway and help you do it faster. You already gave yourself permission the hundredth time you sketched the solution at 2am.

The inevitable needs capital. The improbable needs cheerleaders.

We're the fund for monomaniacal founders.