SAAS Operators Podcast E01: Bootstrapping vs VC Funding

Why Founders Build: Ego, Optionality, and the Folding Chair Doctrine

Every founder has a different reason for building. Some raise capital before they even have a product. Some just want $10K in free cash flow. Some can’t work without aesthetics, while others refuse to replace broken windows in their office out of principle.

‍

On the first episode of SAAS Operators, I sat down with 3 operators—Rishabh (Fermat), Jeremiah (Kno, Stamped.io), and Zach (Foreplay)—and what came out wasn’t a playbook. It was a map of founder psychology. Here's what we unpacked.

Capital Strategy Is a Mirror

Bootstrapping versus raising VC isn’t just a funding decision—it’s a belief system. Rishabh raised off a slide deck (actually, less than that). Why? Because the scale of the ATT attribution fallout was too big to tackle without serious capital. He knew the stakes and wanted to go wide from day one.

‍

Zach, on the other hand, built Foreplay around optionality. He didn’t want to ask permission to make decisions. His first goal? A simple one: $10K/month in cash flow he didn’t have to talk to clients for.

‍

Jeremiah had a hybrid path—agency-backed, revenue-funded, and painfully aware of unit economics. A $100/month product was never going to satisfy a VC chasing billion-dollar outcomes. He realized that early, and instead focused on building a great, profitable company. One that could grow without pretending to be something it wasn’t.

“Lifestyle Business” Isn’t an Insult

Founders love to throw shade at so-called “lifestyle businesses.” Zach called it out for what it is—cope. A few million a year in profit and total autonomy? That’s not failure. That’s winning on your own terms.

‍

The term “lifestyle business” only sounds like an insult when your own business is bleeding cash and your equity’s worthless.

Ego Is a Feature, Not a Bug

The idea that founders are purely rational is fiction. Childhood trauma, petty revenge, stubborn ego—these are fuel sources.

‍

Zach wants to build software, sell art, design a landmark building, and make the Canadian bobsled team. Why? Because a seventh-grade math teacher told him he wasn’t good enough to be an architect. Rishabh won’t let his team buy nicer office furniture because comfort breeds complacency.

‍

Is it logical? No. Does it work? Often, yes.

‍

What drives a founder doesn’t need to make sense. It just needs to push them far enough.

The Hardest Problem Isn’t Building Software

It’s getting people to use what you built.

‍

Jeremiah said 80% of their revenue comes from a single use case. The platform does much more. But once customers mentally categorize you as “the tool that does X,” getting them to engage with new features feels like starting a second company inside your own.

‍

Zach made the same point: new features often land with a thud unless you charge for them. Ironically, free makes people ignore. Price creates pressure. Pressure creates action.

CEO vs. Entrepreneur

Jeremiah drew a clear line: entrepreneurs find problems. CEOs build systems to solve them. One creates. One scales.

‍

Zach doesn’t want to be a CEO. Jeremiah’s trying to become one. Most founders live somewhere in between, constantly switching hats and wondering which role they actually want—or can even survive in.

The Punchline

Building software is never just about software. It’s about alignment. Psychology. Self-awareness. Whether you're chasing a billion-dollar exit or a better lunch break, the same rules apply: be clear on what you want, be honest about why you want it, and build accordingly.

‍

Everything else—funding, pricing, product strategy—is downstream of that.