Startup Poker 2.0 began in early 2007 as a friendly, low-stakes poker game among a few Seattle entrepreneurs and investors.  With the blessing of spouses, the game would move from house to house.  As the invitee list grew, the event out-grew the home-based venues (and the patience of our spouses) and so the event moved to its permanent home — a large conference room at my own startup’s offices.  In the beginning, we were lucky to fill up one table.  The monthly events now regularly draw between 30 and 40 players.

From the beginning, it was clear that sitting around a poker table had a leveling effect on the participants — suddenly, the traditional barriers that existed between young, inexperienced, bootstrapping tech entrepreneurs, their successful serial entrepreneur counterparts, venture capitalists, investment bankers, private equity partners, etc. disappeared.  Now they were just guys (yes, there were just guys in the beginning) drinking beer and trash talking about poker.

What also consistently happened was that important ideas were exchanged and valuable connections were made that could not have been made at most other “networking” events.  This was the revelation that lead to the vision of Startup Poker 2.0 as an “un-networking” event that could connect entrepreneurs with each other as well as the business and investment ecosystems that so many of them just had no access to.

It’s no secret that many tech entrepreneurs are not natural networkers, except perhaps in situations where they are among their engineering peers.  The power of Startup Poker 2.0 is to create an esprit de corps that leads to meaningful relationships within the startup community — especially insofar as it can bridge a gap between entrepreneurs and the business and investment ecosystem they depend on.

The first official venture sponsor of a Startup Poker 2.0 event was Voyager Capital in the Fall of 2008.  Subsequently, Silicon Valley Bank, Ramp Equity Partners and Washington Technology Industry Alliance (WTIA) all sponsored events.   Additionally, Startup Poker 2.0 looks for ways to bring exposure to the startups that attend by allowing announcements and 60-second pitches at that start of the event.  We also look for ways to incorporate the products or services of startup into the Startup Poker 2.0 experience.  As an example, I have used local startup to deliver beer and wine for the event, has provided catering, and volunteered wearable video cameras for another event.  The events are also streamed live through  Startup Poker 2.0 is teaming up with Seattle Lunch 2.0 (winner of the 2009 Seattle 2.0 Award for best startup networking event) for a full-day event in the Fall.

The Vision
We consistently hear from attendees that Startup Poker 2.0 is their favorite startup event and that the connections they make are frequent and valuable.  In light of the resounding feedback and growing demand, we believe that Startup Poker 2.0 is well positioned to move forward with more and better events both in Seattle and other key startup markets around the country.  Over the past year we have received requests to host Startup Poker 2.0 events in New York, Silicon Valley, Boston, Washington DC and Boulder.  Our goal is to conduct the first of these remote events beginning in the August time frame and subsequently executing on one new city at least every other month.  The target size for each event is 45 to 55 players consisting of 70% entrepreneurs, 25% investor community and 5% sponsors.