True Stories: Confessions of a First-Time Founder

On November 1st, 2024, I signed the papers and sold Bold Strategies, Inc. - the company I'd built from scratch over 9 years.

It was one of the proudest and most terrifying moments of my life.

Here's what nobody tells you about building a company:

YEAR 1-2: THE DELUSION PHASE
You think your idea is brilliant. Everyone you talk to says "that's amazing!" (They're being polite.) You burn through savings convinced that traction is "right around the corner." It isn't.

YEAR 3-4: THE GRIND
You've found some clients. Revenue is growing but not fast enough. You're doing everything - sales, delivery, accounting, HR. You haven't taken a vacation in 18 months.

YEAR 5-6: THE INFLECTION
Something clicks. You hire the right people. A big client signs. Revenue doubles. You start to believe this might actually work.

YEAR 7-8: THE SCALE
Systems replace hustle. You're no longer the bottleneck. The company can run without you for a week. Then two. Then a month.

YEAR 9: THE EXIT
Someone offers to buy what you've built. You negotiate. You agonize. You sign.

The biggest lesson? Every founder's journey is lonely. The highs are higher than anything in corporate life, but the lows are darker than you can imagine.

If you're in the early years: keep going. It gets better. And it's worth it.

That experience - the pattern recognition from 81 product launches and a full company lifecycle - is exactly what I poured into building TestPilot.