Two Boats and a Cadillac

On September 28, 2009 I began my startup community journey by meeting with two people; Jason Caplain of Southern Capitol Ventures/Bull City Ventures and Joan Siefert Rose of CED. We met at Cafe Carolina on Harrison Avenue in Cary. There was no heavy action in Durham or Raleigh at the time and Cafe Carolina was THE meeting place.

My goal at that time was to discover what if any assets this area had with regards to software/technology. Over the course of the next 3-4 months I proceeded to meet with about 200+ people. This is how I do it – go talk to people. I am not shy in case you were wondering. I met with 3-5 people a day and I tried to keep those to 4 days a week so on Friday’s I could document what I had just done in the previous 4 days.

I also used the internet to find some background information.

One article I found from that was circa somewhere like 2000-2002 shared an idea about entrepreneurs who had healthy exits. The thesis was that these now wealthy entrepreneurs did NOT go start another company. Nor did they start investing. They went and bought two boats and a cadillac.

It is now 15 years later. There are new entrepreneurs, new exits from startups created 5-15 years ago and more importantly a new community yearning for more connections and capital.

My ask – forego the 2nd boat and invest in 5-10 startups instead. Or join a syndicate of other investors and work together to help influence the next 10 years here. I am not advocating throwing your money away (like you would on a 2nd boat), but investing in instruments that will create a return. In the long run I think you will have more fun than that boat.

What did you do with your exit? 1 Boat. 1 Cadillac. 5 Companies.

Speaker, investor, mentor, startup founder. One of 3 or 4 Co-Founders of MapQuest (sold to AOL for $1.2B). Managing Director of $25M Venture Fund in late 90's. CEO, COO or President of various companies ranging from $200k to $20M in size. One of two Managing Directors of The Startup Factory (35 investments across 7 cohorts), founder and MC of the Big Top Reverse Job Fair and national writer and speaker waxing poetic around startups and startup communities. Currently EIR @ Techstars with Brad Feld ~ Startup Communities, to help community leaders around the world grow their startup community.

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