ASK ANDY - SHOULD MY STARTUP RAISE MONEY FROM VCS? IF SO, WHICH ONES DO I CHOOSE?

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.

- ANDY DUNN

ANDY DUNN, the founding CEO of Bonobos and Pie, offers advice on leading teams, building things, and surviving the startup life. Do you have a question for Andy? Send it to [e-mail].

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.

A $300,000 loan from a family friend was all the startup capital Allen had ever needed. As I scrambled to raise $128 million from investors to sell pants on the internet, I’d always thought that Allen thought I was an idiot. (Which, by the way, he still might.)