Bootstrapping vs. Raising Money: What’s Right for Your Startup?
Framing the Problem: Founders Are Asking the Wrong Question
One of the first questions early founders ask is: “How do I raise capital?”
What they should be asking is: “Do I need capital?”
There’s a huge difference. And I get it—raising money sounds like momentum. You’ve got a deck, a vision, a few meetings with VCs. It feels like something’s happening. But often, it’s just movement—not progress.
When I meet with founders who are laser-focused on raising, I always ask: What will the money actually solve? Most of the time, they don’t have a clear answer.
That’s a red flag—not just for me as an investor, but for them as a founder.
The Solution: Change Your Starting Point
Here’s a mindset shift: Stop thinking of funding as your ticket to start building. It should be the fuel you use once you’ve already proven something is worth scaling.
You don’t need outside capital to validate an idea.
You don’t need a VC to tell you your product has legs.
You need customers. Traction. Feedback. Friction. Proof.
Raising money early might get you attention. But it can also insulate you from the hard lessons that sharpen your business instincts. When there’s too much money, you can afford to ignore the signals.
Bootstrapping keeps you honest.
It forces tradeoffs.
And tradeoffs force clarity.
Idea 1: The Illusion of Progress
Founders who raise early often think they’re making progress because they’re busy. They’re networking, building pitch decks, revising cap tables, taking meetings.
Meanwhile, bootstrapped founders are heads-down, selling, shipping, and building relationships with their first 10, 50, 100 customers. I’m not saying raising is wrong. But don’t mistake busyness for momentum.
The companies I’ve seen succeed over the long haul were built by founders who obsessed over the customer, not the investor.
Idea 2: The Cost of Capital
Here’s what’s rarely talked about: Money comes with a price—even when it’s free.
When you raise capital, you give up equity, yes. But you also give up time, focus, and—eventually—control. Now you’re accountable to a board. To a timeline. To someone else’s expectations. I’ve watched great founders lose their grip on the business they built because they traded long-term clarity for short-term cash.
Ask yourself: What’s the actual cost of this raise?
If the answer is “our ability to move fast, learn, and adapt,” then you’re probably not ready.
Idea 3: Bootstrap Until You Can’t
My best advice? Bootstrap until you hit a wall you can’t climb alone.
Here’s what I mean:
If you’ve done everything you can with what you have, and the only thing standing between you and real growth is capital—now it might be time to raise.
But if you haven’t put in the reps, tested the idea, found your first few customers, or proven that people will pay for what you’re building… don’t raise yet.
Capital should accelerate what’s already working—not try to fix what isn’t.
Conclusion: Build First, Then Scale
I’ve raised money. I’ve also written checks. I’ve bootstrapped. And I’ve seen founders do all of the above—with varying levels of success.
Here’s the pattern I’ve noticed:
Founders who bootstrap early tend to build better businesses.
Founders who raise too early often build better pitch decks.
Which one do you want to be?
If you’re chasing capital because everyone else is doing it, stop.
If you’re building something real and need fuel to grow it faster, raise.
But only after you’ve done the work.