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I asked @Brian Nolan what it was like to raise $5M before he got his first customer... He wished he didn't. A few parts stuck with me: - He wishes he raised $500K first. - $5M created pressure to grow fast. - The next round was already in the background. - He had 3 years to make the story work. - His rule now: pour fuel after the fire is real. My takeaway: Too much money too early can force a company to act older than it is. Full interview: https://www.youtube.com/watch?v=a3I1j97u0Jo

I asked @Brian Nolan about the scariest part of buying a business with his own money. A few parts stuck with me: - His own money was already in. - Revenue was going the wrong way. - There was no outside fund. - He still believed the business could work. - The next bet was hiring. - Waiting meant trying to turn it alone. Sometimes the scary move is spending more before the business feels safe. Full story on Legends of Scale: https://www.youtube.com/watch?v=a3I1j97u0Jo

@Brian Nolan exited 2 companies, raised $5M, and bought a 3rd. So I asked him if Imposter Syndrome ever goes away: His answer was basically no. The full conversation gets into what success does and does not fix: https://www.youtube.com/watch?v=a3I1j97u0Jo