Taking A Pitch Then Swinging

Venture people talk about the ones they missed.  Everyone has an anti-portfolio.  Missing happens.

One of the hardest things to do in venture is to listen to a pitch, passing, then investing on a second go round.  One time I was on a panel with Paul Martino of Bullpen Capital and he mentioned a couple of entrepreneurs they funded where the initial pitch was a pass but later things changed so they funded the company.

In trading, that’s hard to do as well.  You look at a stock at $20/share, then it trades to $30/share and you still have the chance to buy it. Do you buy it?

The difference between that and VC is that you might not get that second chance.  It’s not as if the VC market is highly liquid.  It’s competitive for pitches and egos can get bruised on both sides of the table.

In my angel portfolio, I passed on Riskalyze the first time I saw it. The only reason I passed was the structure of the deal and a little bit on the valuation.  Aaron gave me the chance to invest a second time around a year later with the same structure at a higher valuation.  I invested.

You cannot be stubborn when you trade and when you invest.