the Reality of the VC life

There are times when I think about the VC life and this one line keeps playing over and over in my head which is “What A Long Strange Trip It’s Been” although I’m pretty sure the Grateful Dead was not thinking about the investment world when they came up with that name for their album.

The reality is I have been entrenched in the VC world for 30 years from the vantage point of listening and watching Fred operate.  I have seen and heard businesses fail, businesses exit, founders be replaced, new management come in, finances get restructured, existing investors get crammed down, an IPO, an acquisition, a shitty co-investor, a death of a founder and more.  It is a vantage point that I have leveraged my behind the scenes education into being an angel investor with our own capital.

There are few opportunities to learn how to be a VC.  Few firms bring in apprentices.  One of the main reasons is that to truly opt into a deal and understand it, you have to do your own work, you can’t parcel it out to someone.  The few who have found an entry in the world of investment have been successful entrepreneurs, early employees of startup companies that grew to be huge or just lucky.  What is so intriguing about the business of investing in start-ups isn’t as much about the upside but the excitement of building businesses from scratch.  It always feels amazing to see a company have a positive exit because everyone wins but there is more to it.  The investment business is addictive, I have been referring to it as “crack”.  I want to keep doing it because it is great to be in it and have your finger on the pulse of the future but it is mentally exhausting.

Jerry Neumann directed me to read a piece from Steve Schlafman called Venture Investments Are Not Bets.  It is a great read and anyone who has been in the Venture World for only the past decade should read.  It is a long haul in the world of venture capital.  There are ups, there are downs and as Steve wrote, it is about being active and supporting a company over the long haul.  And that road is extremely long, much longer than most realize.