Scoping Big Bets

I had a Zoom call with a serial entrepreneur a while back. The kind who's seen it all—the wins, the losses, the exits, the crashes.

We got into a debate I've had countless times: Why do some founders seem stuck making endless small moves while others succeed swinging for the fences?

I made my usual argument. You know the one. It's about courage. About vision. About having the guts to bet big when others play it safe.

He let me finish, took a sip of his coffee, and then he completely changed how I think about helping founders win.

The Real Problem

"It's not about guts," he said. "The problem is about scoping."

That stopped me cold. In all my years working with early-stage founders, I'd never heard it put quite that way. But he's right. The ventures that stay small aren't led by founders lacking courage — they're lacking the ability to properly scope the big bet.

Think about it. When a founder makes a hundred small bets, they're not being cautious. They're showing us they don't know how to plan something bigger. Each small bet becomes a way to avoid the harder, unknown work of planning a larger, more comprehensive strategy.

I see this in my consulting work all the time. A founder will run ten different marketing experiments instead of using data, intuition, and taste to craft a few smart bets. They'll chase five different customer segments instead of deeply understanding a primary target. They'll add three half-baked features instead of continuing to refine one great one.

The Planning Paradox

The tragic irony: Making a hundred small bets eats far more runway than making one or two big ones — each consumes and wastes attention, resources, and momentum. Only rarely do they make the big leap that they need to succeed. The result? A lot of motion, but no real progress.

The reality is that the size of your impact will always be limited by the size of your thinking. And thinking big isn't about courage. It's about clarity. About understanding. About the willingness to do the hard work of planning something truly disruptive.

Learning to Scope

That conversation changed something for me.

In my most recent conversations with founders, I find myself asking questions that get them thinking differently. Instead of a pep talk about making a big bet, I'm working on helping them see the bigger picture and plan for it.

So how do you scope big bets? That's a 4-course meal that I'm not cooking in this post.

But I'll tell you that it starts with asking different questions:

• Instead of "What's the next thing we could do right now?" ask "How might we transform our marketing strategy so that we 10X by July?"

• Instead of "How can we minimize risk?" ask "How might we we make this big enough to matter?"

• Instead of "Let's prioritize the quickest wins," ask "How might we sequence our next few outputs to prove we're on the right track so that we're in a position to double down?"

Slow is Smooth, Smooth is Fast

The real courage in entrepreneurship isn't in making big bets. It's in the willingness to set aside time to think them through. To sit with the complexity. To plan at a scale that makes you uncomfortable.

So many founders default to small moves. Big bets require you to confront all the things that could go wrong. They force you to think through dependencies and second-order effects. They demand a level of strategic clarity that many founders haven't developed yet.

To all the founders out there making a hundred small bets: It's not your courage I question. It's your planning. Stop inching your way to mediocre growth and start learning to scope bigger plays.

The future belongs to those who can think at scale. That's the real art of the big bet. Not in the swinging, but in the seeing. Not in the courage, but in the clarity.

Everything else is just motion without movement.