Forget ping-pong and beer. The Triangle startup community is taking its talents to the tables. 

Hundreds of startup investors, founders and executives received invites this week to join Triangle Startup Poker, a new group hosting monthly Texas Hold’em games at hotels and venues across the Triangle beginning in February. 
It’s the latest in a slew of new efforts to get founders and funders together outside conference rooms, bars and co-working spaces. Henry Copeland of Blogads held the first Triangle Tech (Running/Walking) Challenge on his site Racery last summer. Startup Climbing, a local chapter of Denver-based Startup Rock Climbing, had its first event in December 2015. And local entrepreneur and marketer Will Hardison is getting at least 20 people together in two weeks for the first startup Bubble Ball game.
All of these organizers have the same mission—to get people in the startup community building stronger relationships through common interests outside of coding or company-building. And most involve some healthy competition as well.
Triangle Startup Poker was the brainchild of Gregg Gerdau, whose Chapel Hill company Matador Advisors provides consulting and business strategy to local startups and businesses. He’s also an angel investor (who declines to share his local investments) and a serial entrepreneur who has spent 40 years in various technology roles. He was VP of IT for Goldman Sachs, CIO of publicly-traded nVest and CIO of a Kleiner Perkins-funded startup during the dotcom era before starting his own software solutions firm and then working for the startup that brought him to the Triangle in 2004. 
Gerdau has long lamented the lack of the “angel breakfasts” he frequently attended when he lived in Silicon Valley in the 1990s and early 2000s. On any given day, he’d have the opportunity to attend an event with dozens of investors to both build relationships and practice his pitch. In the Triangle, those events were fewer and further between. And because of increasingly murky general solicitation rules, they’ve become almost extinct. 
That’s why Gerdau became so intrigued when he learned of startup poker games happening in Silicon Valley, the most famous of which is held by venture capitalist and early Facebook executive Chamath Palihapitiya. Google “Startup Poker” and you’ll find games in Seattle, Portland, San Diego, Los Angeles, San Francisco, Berlin and Sydney.  One particular organization called Startup Poker 2.0 draws more than 900 players in the five cities in which it operates. It offers prizes or rewards to the entrepreneurs who stand up to share 30-second pitches or company announcements. 

Here’s how that group explains what happens when 50 founders and funders get in a room:

 From the beginning, it was clear that sitting around a poker table had a leveling effect on the players — suddenly, the traditional barriers that existed between young or inexperienced or bootstrapping tech entrepreneurs, their successful serial entrepreneur counterparts, venture capitalists, investment bankers, private equity partners, etc. disappeared. Now they were just colleagues hanging out, playing poker and trash talking. What also consistently happened was that important ideas were exchanged and valuable connections were made that could not have been made at virtually any other “networking” event. 

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 needed access to.

Much of Triangle Startup Poker is modeled off of these events, says Gerdau. But those general solicitation rules, as well as laws surrounding gambling and alcohol in North Carolina, complicated his planning. That’s why he brought on lawyer Benji Jones of Smith Anderson to ensure his games were legal and legit. WooshData’s Charlie Harper is also a partner, helping with website development, marketing and other needs.
No money will be exchanged during the game—that’s what makes it possible for alcohol to be provided by sponsors. And the organizers discourage attendees from talking about fundraising or securities offerings during events. Each person is, however, encouraged to stand up and give a short business announcement in return for an extra 1,000 chips. 
All attendees must also be vetted as entrepreneurs and investors—nonprofits working on behalf of the startup community are also invited. Service providers will only be allowed if spots are available or they sign as sponsors of the games. Up to 50 people will be chosen to play each month in hopes of the crowd always changing. He’s already got 100 people registered with little promotion. 
One thing Gerdau hopes won’t dissuade someone from joining is poker experience. The games will start out easy so inexperienced players can get the hang of it. Only after the fifth round will the stakes rise. 
Another important note from Gerdau: Triangle Startup Poker is a pet project for he and his partners. It’s all for fun, he says, and maybe a bit of personal deal flow.