As An Investor, Here's What Hurts More Than Blowing $5 Million On A Bad Company

Speaking on stage at LeWeb in Paris, Fred Wilson admitted he has some big regrets as in investor- but those regrets aren't investments he's made.

Instead, his biggest regrets as an investor are the opportunities not taken and the companies he missed.

"The painful ones are the ones you pass on that go on on to be worth massive amounts of money," he said.

He described how he botched the chance to invest in Airbnb in a 2011 blog post where he wrote, "We made the classic mistake that all investors make. We focused too much on what they were doing at the time and not enough on what they could do, would do, and did do."

He also admitted that passing on Uber was a big mistake.

"The reality is, if I invest $5 million in company x and it blows up, I've lost $5 million dollars," he said. "If I had the opportunity to buy a 20% stake in a company that ends up becoming worth $40 billion, that's a much bigger mistake."

On the flipside, he said he is most proud of his early investments in Twitter, Kickstarter, and Etsy.