What I Learned From Interviewing Founders Who Sold for $100M+

I have interviewed more than 300 founders over the past several years. Some of those conversations were with people who built remarkable things. Not just by revenue, but by the kind of businesses that changed how an industry operates, and then got acquired or went public for nine figures. I pay attention to patterns. Here is what I actually noticed, as opposed to what business books would have you believe.

They built in public before it was fashionable

The founders who had the biggest exits were almost always visible long before their exit. Not performatively, not with polished "thought leadership," but genuinely , sharing what they were figuring out, admitting what was hard, asking questions in public that most people would be embarrassed to ask. By the time they had something to sell, they already had an audience of people who had watched them struggle and grow and figure it out. That audience became their first customers, their warmest leads, and their most vocal advocates.

None of them told me they planned it that way. They were just being themselves in public, consistently, over years. The compounding effect surprised even them.

They were obsessed with relationships, not transactions

The founders with the biggest exits almost never described their business in terms of customer acquisition. They described it in terms of people they knew, trusted, and had built something with over time. Their investors were people they had known for years before they took a cheque. Their key hires had been in their orbit for years before they joined. Their acquirers were people they had been in conversation with long before any formal process began.

This is not a networking tip. It is a different operating philosophy. The transaction-focused founder is always hunting. The relationship-focused founder is always building. The latter is more exhausting in the short term and dramatically more powerful over time.

They spoke plainly

Without exception, the founders who had significant exits spoke to me without jargon. When I asked them how their business worked, they explained it in language a smart fourteen-year-old could follow. When I asked them what went wrong, they said what went wrong. No corporate hedging, no spin, no carefully managed narrative. Just directness.

That plainness extended to how they showed up publicly. Their posts, their talks, their interviews , all of it was recognisably human. You always knew who you were dealing with. In a world saturated with polished positioning, that clarity was itself a competitive advantage. Consistent visibility, in a voice that is genuinely yours, is not a soft strategy. It is what the founders who built the biggest outcomes were doing the whole time, whether or not they called it content marketing.