Winning When You Lose

Losing money is brutal.

I have invested through some major cycles over the last 30 years, so for you adderall chewing, avocado eating millennials believing ‘TTID’ (This Time It’s Different) please cherish these good times.

When the losses finally happen, you will truly find the people you want to do business with again.

Today Fred Wilson wrote about making friends with losses. I have invested with both Brad and Fred and they are legends not for just their wins. I have had to make a couple of hard calls to both of them over the years investing together and they have been incredibly supportive.

Today, I also caught up in person with Roger Ehrenberg who is a friend, mentor, partner and incredible investor.

Roger and I have had some huge wins together as angel investors including my last Company Wallstrip, Buddy Media, Ticketfly, Tweetdeck and Tubemogul.

Roger is also an investor in Stocktwits and an LP in my Social Leverage funds.

Most importantly per the life long business of investing, Roger and I have taken a couple of losses. Roger has always been the partner and investor that takes the hard calls in stride and digs in to help when you need him.

If you are a founder or investor, you should be so lucky to get people like Roger, Fred and Brad on your cap table.


Also published on Medium.