Six years as Heroku’s CTO was the greatest professional experience of my life. But what’s next?
On January 2, 2014, I boarded a one-way flight to Germany.
I’ve never lived outside the US, and my career, professional network, and friends are based in San Francisco. My intention: to connect with startup people in Europe. But what would they say when a stranger showed up out of the blue, asking to join their scene?
What I discovered was a vibrant and thriving community of people and companies, and they welcomed me with open arms. In this article I’ll tell you why I did this, how it’s played out, and what’s next. Let’s start at the beginning.
I was drawn to entrepreneurship when Orion Henry lured me away from the video game industry in 2000 to start TrustCommerce. I quickly came to love the challenges, passion, and intellectual stimulation of entrepreneurship.
Orion and I started several more ventures together, and along the way we met the third member of our trinity, James Lindenbaum. In 2007, the three of us set out to solve the web app deployment problem. Thus, Heroku was born.
We knew we wanted to go big with Heroku, but we had no idea of the success — or the struggles — that lay ahead. We moved to San Francisco, joined Y Combinator, took VC investment, and went deep in the Ruby community. Six years later and we had seen it grow to a 120-employee company with a quarter-billion dollar exit to one of the world’s fastest-growing public companies. Most satisfyingly, we had become a household name among developers and changed the way that people think about building and running web apps.
In the summer of 2013 I made the extremely difficult decision to leave Heroku. The team there is like a family to me. I’m incredibly proud of everything we did there — and the great work they’ve continued to do since my departure. But my creative muse for that problem space was tapped out, and it wouldn’t have been right for me to stick around longer.
After a successful exit, startup founders often go on to become angel investors, advisors, or EIRs (entrepreneurs-in-residence) at VC firms. This path is appealing because it lets you dabble in a lot of things, satisfying your intellectual curiosity and using your hard-won startup experience to help others succeed. It also avoids the crushingly heavy day-to-day responsibilities of being a founder or senior manager at a growing startup.
I dabbled in investing and advising, but found it unsatisfying. I like to build things, I like to own things. I want to make tough decisions with limited information, weigh risks and take bold action, on a daily basis. I love the intensity and emotional rollercoaster of day-to-day life in a startup.
The spiritual exhaustion that followed the six-year adrenaline high of growing Heroku has not entirely lifted, so I’m not quite ready to make the implicit commitment that would go with founding a new startup. Just as importantly, my lifelong business partners James and Orion are both working on their own projects right now: James on Heavybit, theaccelerator for developer-facing product startups; and Orion (assisting his wife Jaymie) on The Right to Heal, a documentary and public health initiative to bring basic essential surgeries to developing nations.
The answer has turned out to be a cross between advising (infrequent, high-level assistance to a company paid in pure equity) and consulting (deep, short-term projects, usually paid as an hourly rate). I have started referring to this as “deep-dive advising.”
I start by talking with founders (or whoever the senior leadership for the company is) to help figure out what some of their biggest challenges are, right now, in their company. Then we identify a project that fits with my skills that I can go deep to help them solve, or at least make a very substantial start on.
For example, my first project is with Clue, a 10-person startup based in Berlin. They’re an app for women to track their menstrual cycles, although this is just the beginning. They have a much grander vision, addressing reproductive health with modern technology products. I’m helping them build technical infrastructure, make some key hires, and address some critical data privacy questions.
Clue first caught my eye because of this line on their Jobs page:
I’m scheduled to work with Clue for most of February. It’s a full-time gig, with me in their Kreuzberg office every day at 10am, participating in the standup, attending the company all-hands, and participating in the company chatroom and email. (Email me at firstname.lastname@example.org if you’ve got a Clue-related question.)
I love San Francisco, and it’s a place that has been very, very good to me. And it’s home to many dear friends. But the tech boom there feel like it has hit a saturation point. It’s no longer the frontier.
For startups, this means seeking new problems, new markets, and new talent pools. So I made a list of criteria for what I was looking for out of a new place and asked about a dozen of my well-traveled friends for their recommendations.
The uncertainty I felt at flying to a new country to connect with an unfamiliar scene quickly dissipated as I met people here. Starting with a few cold emails to companies I discovered by searching job boards, I managed to get dozens of meetings and attend a great startup event.
I was absolutely floored by how welcoming the startup scene is here in Berlin, and in Europe in general. I’m equally thrilled by the vibrancy: the number of startups, the quantity of smart and ambitious people, and even the quality (if not quantity) of investors.
The feeling here in Europe reminds me of San Francisco when I moved there in 2007. It’s hard to even remember this now, but back then, Y Combinator was practically unknown. When my partners and I joined the YC mailing list, the alumni from the previous class (all of about 10 people) excitedly put together a dinner for us. At that dinner the Dropbox founders proudly told the group that they had just closed their first round of funding and made their first hire. How the world has changed since then.
Nowadays there are thousands of YC alumni, not to mention thousands of tech and startup people of all types coming to the city to find their fortune. I think this is wonderful. But for me, I’m happiest in a community that is smaller and more tight-knit.
I believe in the Silicon Valley / startup approach to problem-solving. I think there are a vast many ways that the human condition can be improved by applying this approach, and that we’ve only just scratched the surface with the startups that exist today.
I’d love to see a diaspora of startup thinking and startup culture spread around the world. That culture is one that believes things can be better; believes that “user experience” is found everywhere; and believes that small teams of dedicated people can make breakthroughs not possible via the established institutions of big companies and governments.
I’m hoping to bring some of whatever Silicon Valley street cred I have to Europe. I’m not the only SF person to come here, but I hope I can help light the path, and maybe change a few minds that the only place startups are possible is in California or the US.
Update: Curious how the story ends? Here’s my follow-up post from a few months later.