How hundreds of coffee meetings have paid off for TeachStreet

Even though I keep my list of blog subscriptions pretty small, I’ve been weeks behind in my blog reading. Partially, that’s because I feel like I see most of them in Summify (yes, I LOVE Summify!) and my tweet stream, but I sometimes miss the really good posts.

In that vein, I just read Mark Suster’s post about the Importance of Doing 50 Coffee Meetings, as a way of expanding your network.  After reading it, while walking the dog, I thought about how many of the successes in my last 4+ years with TeachStreet have been the result of non-agenda coffee meetings and the like.  Many people look at these types of meetings as “the wasted-time-stuff-that-biz-people-do”, and I admit that I sometimes feel that way about them too.  But, another way of looking at them is as the types of things that ‘create luck’ for those who are willing to put in the effort.  They’re not activities with fairly-certain-outcomes, like writing code (where there’s a definite output) or testing a paid-search-campaign, and that’s what makes them so exhausting, at times.

If it helps, I thought I’d share some of the outputs of those types of random meetings — I bet that none of these wouldn’t have happened without the hundreds of meetings:

• Our first $100k angel investor came from a friend’s intro; the investor met me one time, and called me a few days later with the news of his investment. Upon hanging up the phone, I actually screamed out loud.
• Almost all of my angel investors were originally soft-pitched over coffee, as were many non-investors; more often than not, the non-investors helped with other introductions, ideas or questions
• I originally met Daryn (our CTO, and the person I consider my TeachStreet partner) via a random networking meeting, where I met he and David Geller, as they were working on EyeJot. And, I’d bet that more than 75% of our employees were introduced, or met, over coffee and/or network introductions.
• I met Joe Heitzeberg, over coffee at Macrina, to discuss a role he had open at Snapvine; by the time of the meeting, I had already decided on TeachStreet, but it’s a relationship that’s grown since 2007.  Oh, and he introduced me to our accountant, who’s just awesome.
• The idea for TeachStreet crystallized over a coffee discussion with Jason Kilar, while we were discussing a pre-Hulu startup-idea that he was starting to accelerate toward
• While not a coffee meeting, we ended up licensing our software to a company in Australia; they found us because of a video presentation I gave at a Seattle Tech Startups event — they caught the piece of the video where I said that “we’d be open to licensing our software”, and reached out (note — I also fielded ~30 of these international outreaches from others, that all went nowhere…)
• I met Dave McClure years before any startup notions — he was on the Board of Unitus (a microfinance organization, where I was the guy responsible for marketing); as fast as he could spew ideas, I was sitting on the fringes of the meetings implementing/testing them.  That relationship took off quickly 🙂  Dave turned into a great friend, one of my earliest investors, and biggest advocates (and out of that grew uncountable press/blogger introductions for me, and referrals of Seattle-initiated-startups, by me, to 500Startups)
• Out of a coffee-request overload, we created Hops and Chops, as a way to consolidate many of these conversations, and enable even greater early-entrepreneur interactions.  Entire startups have been assembled there, and numerous friendships have deepened.
• We recently got one of our first exclusive-lead bus-dev deals done, in days (after multiple attempts with the company), after a coffee meeting where I helped them with some candidate sourcing
• Finally, one of my very first startup inspirations/enablers was Andy Sacks’ Open Coffee, that he’s been running, at Louisa’s on Eastlake for 4-5 years, without fail.  And, as I look back, that’s where I met Tony Wright for the first time!