What Was Your Biggest Surprise as an Investor?

Seraf Co-Founder Christopher Mirabile interviews several experienced angel investors from around the country to find out: "What was your biggest surprise as an investor?"

Learn what Dave Berkus, Basil Peters, John Huston, Maia Heymann, Joe Caruso and other early stage leaders have to say, and how their insights can help shape your investing decisions.


Video Transcript

C. Mirabile: What was your biggest surprise as an investor? [00:00:06]

D. McClure: You know, I think, you know, genius emerges slowly. I think there's a lot of really great entrepreneurs that we've invested in but the ones that have done the best weren't obvious at the beginning. They became obvious two, three years in. [00:00:09]

B. Peters: My biggest surprise was early on, after I had been a successful entrepreneur and I had some money and I invested in some companies, and I had a clear belief that the entrepreneur was heading in the wrong direction. I began to realize that mentoring is a lot more difficult than I originally thought and a lot of times even when they seem to be listening, they're not really changing what they're doing.  [00:00:25]

R. Sheridan: When someone you've invested in loses their way and panics. [00:00:49]

J. Huston: My single biggest surprise is how much I thought I knew that was not relevant to this business. [00:00:54]

F. Peters: The time to exit is so long. I think that surprises many of us, right? It's taking a long time. The IPO market is gone. [00:01:03]

N. Ravikant: Valuation matters. There's a lot of talk out there that valuation doesn't matter and you should try to get into the hot deal at any price, but on a portfolio basis it absolutely matters. [00:01:15]

D. Berkus: The biggest surprise was the VCs. Once they invested, they didn't want to have a successful business, they wanted to have an over-successful business. So they pushed up the monthly nut to $800,000 a month. And none of us could understand that, so they had us spending $800,000 a month right into extinction. [00:01:24]

J. Caruso: I had one entrepreneur that I thought was one of the best ones, that my gut told me was great, and he ended up imbezzling $3 million dollars from the company and it went out of business. [00:01:44]

M. Heymann: I wouldn't say it's a big surprise but it's nothing ever turns out the way you think it is. [00:01:55]

J. Huston: Nobody really successfully has handicapped who is going to win the battle. There are always exogenous variables. We deal with uncertainty. [00:02:03]