🕺🏻 Bootstrapping or Fundraising? Neither.

When it comes to startups, founders often divide into two camps. On one side, there are fundraising evangelists who see securing VC investment as the ultimate milestone—validation of their brilliance and their startup’s potential. On the other hand, there are bootstrapping enthusiasts who view investors as villains and take pride in their independence.

I’ve tried both approaches over my 12 years of building startups. And here’s my take: Neither of these ways suits me. I’ve found a third way—a more efficient path that avoids the pitfalls of both extremes.

The Fundraising Obsession

Let’s start with the “money-first” mentality. Founders in this camp often raise too early, using investor interest as a proxy for validation instead of listening to their users. This leads to a disconnect from the real world. Instead of focusing on building a product users love, they create something tailored to investor hype—big and shiny but solving no real problems.

Another issue is the time spent on fundraising. Hours are wasted rebuilding decks, pitching, and networking with VCs—time that could be spent building the product and talking to users. At an early stage, spending time with 100 clients yields far better insights than spending it with 100 VCs.

Worst of all, raising capital too early often slows founders down. With money comes overhiring and unnecessary complexity. It often leads to scattered efforts, building too many features, losing focus, and slowing iteration speed. Lack of funds forces prioritization and sharpens focus. Early-stage startups thrive best when they stay small, fast, and scrappy.

The Bootstrap Bias

Bootstrapping is often seen as the ideal path. It involves avoiding answering to VCs, maintaining complete control over your startup, and keeping your life simple. Bootstrapping forces discipline and prioritization and is excellent for staying lean and focused.

But bootstrapping has its limits, especially if you want to build something beyond a lifestyle business.

If you want to create a product that truly matters to a large audience—something impactful that leaves a mark—you need to scale. Scaling with only your resources is slow and often impractical. Fast scaling requires funding, the ability to delegate, and building strong teams that can accelerate growth.

The Middle Path

In my experience, it’s all about sequencing:

1. Bootstrap to PMF: Use bootstrapping to stay focused. Start small and stay scrappy. Focus on testing ideas and finding what works. Small teams mean faster progress and better communication.

   When bootstrapping, it’s much easier to fail quickly and iterate than after raising funds. Yes, it can be challenging and even painful at times. But this humbling journey will prepare your ego for success—without it, you might not be ready when it comes.

2. Raise Post-PMF: Raising becomes easier and faster once you’ve proven your PMF. Investors love traction, and you’ll be in a strong position.

3. Scale with Intention: Funding becomes a tool for buying speed to scale. Your only goal is to scale as quickly as possible.

Why I believe in it

This balanced approach respects the truth about startups: they’re experiments. Until you find PMF, every new hire and feature adds complexity without adding certainty.

Post-PMF, speed is your greatest advantage. That’s where fundraising shines. It allows you to scale what is already proven to work and outpace competitors.

But there is a pitfall

It’s easy to be misled by over-optimism. When building Hints, there were two moments when I was sure we’d found PMF. I wanted it so badly that I convinced myself it was real. Both times, I raised money, only to find out it was false PMF—a quick hype that landed thousands of users but didn’t translate to monetization or scalable growth. This time, I’m cautious.

Final Thoughts

A startup isn’t just a business—it’s a dance between agility and scale. Bootstrap to stay agile. Raise to accelerate. But never let money—whether raised or saved—become the goal. The real goal is to build something people love and scale it quickly. Money follows.

It’s also important to understand what you want and why. I build startups to sell them one day. For me, building products is a form of art, and selling them is recognition.

I've chosen different paths at different times in my life. During GetIntent, it was all about raising and exiting. When I started Hints, I wanted to avoid the VC game. But after months of bootstrapping, I felt bored because it was too slow. After failing with premature PMF and pivoting to CRMchat, I returned to bootstrapping. Now, I’ve realized I don’t need to choose.

Until next Sunday,
George Levin
^{LinkedIn | Consulting}