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










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.

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.

892216_10151501323894099_1478320609_oIt 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.

Grassroots Innovation: It’s about Permission

This post was originally posted here. 

Last week, I had the pleasure of attending the UP America Summit, in friendly Iowa City, Iowa. It was put on by UP Global, the folks behind Startup WeekendStartupDigestNEXT, and Startup America. They got a bunch of us who run innovation programs together for a dedicated corporate track, to share our common learnings, struggles, and success stories. I represented The Garage, Microsoft’s grassroots innovation community, along with people from Coca-Cola, Sprint, The World Bank, GoDaddy, American Airlines, ACT, Hallmark, and others.


I put together a few of the key themes that emerged over and over within the group and wanted to share them here. The one that absolutely resonated with everyone instantly, is the title of this article, and the the first point I’d like to call out:

  1. Grassroots innovation is about permission. Fueling creative tinkering with new ideas can’t be management-directed, but it must be management-supported. Those closest to the customers, problems, and existing products (typically at the bottom of a hierarchy) have the most personal drive to try a new approach to a problem, and this autonomy fuels their projects long after an executive mandate has worn off. However, if an employee feels that their efforts to innovate are counter to their “real job,” the project tends to die off over time. One thing that we practice at The Garage is having passionate employees plan and organize a Garage Week (think: blue-sky hackathon within an product team), but have executives promote participation via an email to the whole organization to grant such “permission to innovate.”
  2. Innovation is about a culture shift, not just money or ideas. Nobody owns innovation. Neither infinite resources, nor the “perfect platform” to surface the most innovative ideas will succeed without an organization-wide chutzpah toward innovation. We found that many of our companies have seen various forms of “internal Kickstarters,” idea voting platforms, and contests that did not achieve their goal of finding “that next big innovative thing” without a cultural embrace.
  3. Open innovation is important. Mathematically, the sum of experts with skills and experiences outside of any given company is larger than the sum of experts inside. We are often blind to a future innovation because we don’t embrace those outside our organization who can truly define the problem and solution. Getting employees outside the walls of the company and out into the community is paramount.
  4. Access is the greatest thing we can provide startups. And more specifically, access in a timely manner. If a startup is working toward a partnership with a large company, they often waste an incredible amount of time being passed around internally. If we really want to encourage open innovation and allow an idea to flourish, the greatest service we can do is recognize if it isn’t a good fit early, cut the chord, and save the startup valuable time by being honest and closing the door. If we can think of an introduction we can make that’s a better fit, that’s a bonus too. The list of startups that had an interesting new product that failed due to partnerships with a big company that never quite materialized is far too long.
  5. Innovation isn’t new. We can learn from our company history. Every billion dollar company, whether it is innovative today or not, had at least one enormous innovation in the past. It could have been business model (such as the advent of loyalty programs) or technology (such as the computer mouse), but that billion dollars didn’t come from doing the status quo. So, we should look within our companies at the environments that created those innovations in our past. The nuance is that recreating these conditions is hard since the these often occurred before exponential growth. Innovation at scale is a much trickier problem since it involves a massive amount of communication, collaboration, and precision. But at least, by examining our history of disruptions, we’ve got a great place to start.

The most important thing that we can do now: keep sharing our successes and failures with each other. We can approach corporate innovation the same way that we approach Startup Weekends: experiential education, where we learn by trying new things, and iterating when something seems to stick.