When Ryan moved into the office he wasn’t super keen on the outdoor sports, so we picked up a free air hockey table on Craigslist.   It was obnoxiously loud, and only two people could play.  If you missed the puck you were liable to bruise your fingers, but if you hit the puck at just the right angle, you could sneak shots in all day long.  We mastered it within about a month, and after that it sat idle until Zach and Bobby decided to have a contest to see who could sell it for the most money.    Zach won by discounting it to the first buyer.

Proceeds were used to buy an old Harvard Foosball table, the perfect game for an office of 4.    We played our hearts out on that table. Ryan came out of his shell and emerged as the wittiest of us all, Zach started to be nicer when he realized it would only amp Bobby and me up and make us play better.    We laughed, we fought, and then we played some good foosers and realized how shitty we (and our table) were.   Ray, saved us and let us steal a Tornado table from the Yahoo offices.  We sold the old table for twice what we paid.   Over the last year, Zach has mastered the Snake, Bobby has stopped making Bobby goals, and Ryan has a wicked R-Force.   We eventually bought gribs, learned to scuff the ball and lubricate the table.   Although we’ve tried many times to change the teams, they end up always being the same.   Me and Bobby vs. Zach and Ryan.   Zach and Ryan used to win the majority of games, but lately we’ve been making a strong showing.    All of this has led to the evolution of the $5 game.   One game a day, its for $5.  Money is on the table immediately after lose.   Right now Bobby and I are down $15.   It’s only a little bit competitive.

All of our games have constantly reiterated the importance of play in the development of Triggit, and our growth as a team.   When we are angry, we take it to the table.  When we are celebrating, we play a game for fun.    When we just need a break, the competitiveness of our games demand your full attention.   We don’t take fancy retreats, and although great friends we really don’t hang out that much on the weekends, but we do play some foosball. And over that table, through play, we have created a foundation that won’t crack.

I’m always torn at such functions if its better to be brutally honest about experiences as a  young entrepreneur, or instead to create a thin wall, a façade that separates reality from the utopian existence we all claim to reside.

At the Churchill Club I chose honesty, telling a story about Zach sitting in the back of the infamous Ritual Roasters Coffee House , Ruby on Rails 101 opened on his lap,  convinced he/we could learn the complex programming skills necessary to get Triggit built.  Oh what fools we were.  Luckily we quickly realized there are a few more levels to programming then ‘Rails’ and moved beyond our stupidity,  somehow convincing Ryan it was in his best interest to come work with Triggit.  (That is another story entirely!)

Triggit didn’t start from some singular brilliant idea, sketched out to perfection from the beginning.  We didn’t release a magical application that instantly hit hockey stick growth, became profitable, went public and pours billions into the coffers of its stock holders to this day.  But then again, that reality is the fairy tale.   Even the most amazing products frequently struggle to truly succeed, especially financially.  Google went through 6 known iterations of its business plan, from licensing its search technology to the roaring success of Adwords. And Facebook sure can grab users, and claim high valuations, but they are far from turning a profit.

Reality for the majority of start-ups is that it takes a long time to build something that has real value, especially for first time entrepreneurs.   In the early days of building Triggit, without an established network in the Valley, and when we were first trying to figure out exactly how this all worked, we would just call people.  Anyone who would listen to us, who was in some related field (usually just anyone in tech) was liable to get a phone call from us. We rooted through our Alumni directories looking for ANYONE who would take our calls.  Looking back I just laugh at how serious we took this whole endeavor, but it was a step in getting us to where we are today.   Because the more phone calls we made, the more we vetted out ideas, and the more clear our eventual target became.

We went (and still go) to as many networking events as possible, just to talk about Triggit, see how people react, and come back to the office to iterate.  Then there are the days you just stare at your computer screen, trying to figure out exactly what it is you are supposed to be doing.  Bobby spent months trying to sell a product, before we actually had a product.  And then there are nights you wake up at 3am convinced you suddenly have it all figured out.   In every case, most time is dedicated attempting to execute a series of realities that most often fall flat on their faces. Failures sometimes bruise egos, loose money, and waste valuable time, but they also move us ever closer to the light at the end of the tunnel.   They also make the rollercoaster of a start-up one hell of a ride!    And the ideas that stick, that make it through the guantlet,  well, those are the really good ideas.   A few years after  jumping on a plane from beaches of Brazil to join Zach in pursuit of this crazy start-up, we may just have one of those really good ideas, and a truly fantastic product.

I hope I can always feel the freedom to write truthfully about my company and our crazy experiences; about the paths we should never have gone down, the silly moments wasted chasing elusive prestige.   But more importantly, the great times.  Like the time Zach rivetted an audience at the Web 2.0 Expo, making them full commited to the cause, and convinced that we can and will succeed.   And most importantly, the internal moments, not just becoming really good at foosball together, or getting drunk at Zeitgeist and inventing religions, but when we come together as a team, to execute on an idea, and watch it start to succeed.   Damn its a fun ride!

Take a look at the Churchill panel if you are interested (or just fast-forward to all the fascinating parts where I speak!).    And let me know what you think, I have learned a lot about myself in watching that clip, and I can’t wait to keep learning more!