A friend—I’ll call him Allen—spent years bootstrapping his real estate enterprise software company. After a long struggle to get to $1 million in sales, his business recently surged to $10 million, and revenue is now growing 100% year on year.
Prior to that inflection point, Allen had never raised venture capital. I had always perceived him to be a bootstrapper by choice, assuming that he’d never pitched anyone. He wanted to do it his way, I thought. He was scrappy. He owned his whole company. He was a benevolent dictator, revered by his team. His company had always been profitable.
