"I agree that visionary young people are worth backing and we do a lot of that at Union Square Ventures. But there is another kind of entrepreneur I love backing even more. It’s the serial entrepreneur who has had a number of successes under their belt and now wants to swing for the fences. We have a bunch of them in our portfolio and there is nothing more fun than watching someone who has a ton of experience get behind the wheel and really step on the gas. When someone has two or three startups under their belt, they understand a bunch of things that a first time entrepreneur doesn’t. They understand the value of setting a very clear vision and getting everyone on that page. They understand that they need to hire the very best people. They understand how to raise capital and pick their investors carefully. They understand how to make quick decisions and not let issues fester. They have a rolodex of talented people and potential business partners they can get on the phone or email quickly when they need them. Most of all, they ooze confidence and make everyone better around them. These entrepreneurs usually have enough money in the bank that they are not looking for a payday. They don’t build their companies to flip. They build their companies to go all the way. They are doing it for money, but they are also doing it for the thrill of the game, for ego, and to build a legacy. Those are very powerful motivators, much more powerful than money if you ask me."
—A VC
