23 Events, 6 Years, and Countless Friends: How Startup Weekend Shaped My Life

This piece was originally an impassioned Facebook post that quickly became the longest I’d ever written. After I published it, UP Global syndicated it on their blog, so I figured I may as well do it too. It is the most cathartic thing I’ve ever published here.

It is nearly impossible to accurately measure the impact that Startup Weekend has had on my life. It’s difficult to picture who I would be without it. Today’s news about joining Techstars has been an impetus to reflect on it. In thinking through the ways it affected my path to (maybe eventually) becoming a grown-up, there are four major things that come to mind.

1. Creating my first app. I first attended Startup Weekend in Columbus and worked on the app “Photo Food Journal.” It’s funny looking back on how many times I’ve heard this idea pitched at subsequent weekends, and how some larger companies are working on the idea as well. There’s always that set of apps (parking, beer tracking, food tracking, travel planning, etc.) that attendees pitch. It’s a right of passage for the first-time entrepreneur. Photo Food Journal led to me becoming an iOS developer on the side while I was a student. This begat SeizeTheDay, which was an app I developed featured by Apple, and made real money for a college student. This gave me the entrepreneurial itch.

I also credit starting SeizeTheDay in college as the reason I landed my first job working on the then-unanounced Office for iPad at Microsoft.

It also just so happens that this was the weekend I met my dear friend, backpacker comrade, and mentor, Nick Seguin. If this post stopped right here, it would have been enough. Or, as we Jews say, Dayenu!

2. Learning how to speak in front of people. I’ve been involved with 23 startup weekends now, from Columbus, to Seattle, to Kamloops – and even to Malaysia. At Startup Weekend, after you attend, you can help organize your next one, and eventually become a facilitator to go and run the event in other cities. When I facilitated my first event in 2010 in Columbus, I was a Junior in college, and a CS major with no “business side” to compliment. I’ve never had a problem with self-confidence, but I was no business person, and I certainly wasn’t your typical charismatic emcee. As I facilitated my next 10 events, Startup Weekend was my platform to sharpen those skills. I now find such joy in being able to talk to a large group of people and share stories from projects and teams I’ve been a part of.

It is worth mentioning that these skills have a profound impact on my social life as well. The personal self-confidence that spills over from of talking to groups about entrepreneurship is enormous. It’s a rock of stability by which I’ve drawn other courage and strength.

3. First press. Okay, this one is silly, but it’s worth mentioning. In September of 2010, just before I left my CoTweet internship in SF to go back to school, Eric Kerr and I attended the pitches for Startup Weekend Education and hung out with the one and only Shane Reiser. Sitting in the back of the room (and doing some extreme pattern recognition), we created and launched http://itsthisforthat.com during the pitches. After indulging in a few libations to grow the pool of “this’s” and “that’s”, we launched the site, tweeted about it, and I had my first taste of virality. It was my first time ever being written up in TechCrunch, and it led to introductions with talented people for years to come.

4. Making lifelong friends and working with world-class people. The list here is far too long for this post, but I want to name a few.

When I was working on Office for iPad at Microsoft, I was facilitating Startup Weekend events several times a year as a volunteer on the side. Liane Donald Scult happened to be in attendance at the Seattle event I facilitated, and asked me, “If you’re doing this in your free time, why aren’t you doing this for your job?” This was the first event in a series that led to running The Garage at Microsoft, and continuing to work on the vision that Quinn Hawkins, Liane, and many others had started. For those of you counting out there – that’s my first 2 jobs out of college.

When I moved out to Seattle for my first gig with Microsoft, Nick Seguin introduced me to Greg Gottesman. Greg and Nick were friends from the Startup Weekend board, and thought we should get to know each other. My coffee with Greg turned into a 3-hour walk, some really bad 1:1 basketball, and a teriyaki run. Greg stayed a close mentor and friend for a couple of years after that, until I left Microsoft to start Madrona Venture Labs with Greg last year. Let the scorekeepers know that they should add a 3rd to the list of jobs I’ve had because of Startup Weekend.

The week I moved to Seattle, Andy Sparks, one of my best friends from school, introduced me to fellow Startup Weekenders Kav, Donald, and Scott. When I had no friends in Seattle yet, they took me out for drinks. I suddenly had friends in a new city. This sort of thing has happened over and over again. Zachary Cohn, another of my first friends in Seattle, was a fellow Startup Weekender.

I knew Keith W. Armstrong and Adam Stelle only from their Startup Weekend email addresses for years, and have developed great friendships since moving out. Chet Kittleson and I even started Red Ride together at a Startup Weekend, and while that no longer lives on, our friendship will for years to come. Two of my closest friends, Tori and Philip, are friends from the Startup Weekend we held at Rover (a company started at Startup Weekend!) The list goes on.


When I search my Gmail inbox, I have 3,852 emails containing the phrase “Startup Weekend.” That’s a company I’ve never worked for. Startup Weekend is a fascinating case study in bottom-up, grassroots organization. I am just one of the hundreds of thousands of lives around the world that have been touched by it, and I couldn’t be more grateful.

Startup Weekend hasn’t changed my life. It’s created the life I have today. The people, opportunities, and ideas over the last 6 years have done far more than I can articulate in this post. Thank you Marc, Clint, FranckAndrew and everyone else who has built it along the way. Congratulations, and enjoy the next chapter of the journey with Techstars.

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