Bets We Didn’t Make … and Probably Should Have

These are companies in which we had a chance to invest, but we were ‘way too smart’ … not.


One of our good friends made an early investment and let us know that we could too. What? Real ugly rubber shoes; that doesn’t sound like something that will sell. Of course, the rest is history (without us).


We were introduced to the founder and liked him; had discussions and offered advice about their initial product set. We should have invested in John. Others did and did well.


We heard about Hudl from a friend when they were raising an early round back in the 2007/8 timeframe. Videos for high school coaches; we don’t get it. Big mistake!

Social Money

We met with the founders and Scott McCormack a number of times and we just couldn’t figure out whether the ‘savings platform’ was something that FI’s would want or not. They sold to Q2; banks indeed wanted their product!


We met the founder when we were starting Sojern and knew him to be a very sharp guy. The company was successful and sold to AppNexus. We should have known that Tom Shields was worth a big bet.

Catalyst Secure

A lawyer at a firm that was a ‘closet’ technologist; wanted to split from the law firm and obtain the IP that he had been working on to find ‘word strings’ in all sorts of documents. We passed; our friend didn’t and it has been a very successful company.
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