On Leaving DigitalOcean and What’s next.

I think it’s fair to say that across the globe you’d be hard pressed to find someone who knows me that doesn’t know how deeply I love DO. What I truly love however, is the humans behind DO and those that use the service. November will be my last month with DO. My DigitalOcean story is maybe a little different than some, if you’ll give me a moment, I’d like to tell it to you.

I was fucking up the culture at StillMotion, the film company I helped establish and grow out of college and was fired by the founders from the ceo position. I was 24, angry, pretty down on myself, and doubted my ability to ever do anything meaningful.

In mid 2010, I followed a girl to Manhattan and began trying to find that meaning. After five painful years of tooling around in startup, I was feeling incredibly lost. That year I was introduced to Mitch Wainer by Trace Cohen. Mitch was starting this thing called “DigitalOcean” and Trace wanted me to talk to him about how Jark and our team built the community at DeviantART in the 90s.

First Office Roof

Trace was cool so one evening in August 2012 I dropped by a small corner office in a beautiful old building on Lafayette at Houston. I recall it was quite cold, and the office was warm and glowing, it felt alive, had a real energy in the air. In it I found Jessica, Etel, Neal, Jeff, Ben, Moisey and Lev. Mitch introduced me and I walked around and talked to everyone as they explained to me what they did. Etel was writing articles, managing the community, and running support. Moisey was working on the product, how it would all come together, acting as a master PM if you will. Jeff, hacking away on what is now the mostly refactored code base and Neal explained the scheduler. Mitch outlined the value prop and Ben how the business model worked. Jessica managed the books, the office, EA and HR. I’ll never forget when Moisey, chain smoking out a window, asked Ben if it was ok to show me… as Lev, who ran infra, opened a massive box of…dun dun dun.. SSDs.

wtf? An SSD cloud built for developers? With 512mb ram? For $5/mth? Deployed in 55s? With a beautiful interface? In 2012? Wild……. I was totally inspired. Totally totally enamored with this team. Everyone was brilliant, sharp, and clearly understood their part in the mission they were executing on. Lencioni would have been proud of their organizational clarity.

I knew that night with certainty DigitalOcean would become something very very special, it had to because I was standing in a room full of very special people, it felt amazing. I’ve always admired and looked up to Ben, Moisey and Mitch, there are very few people I would work for, but it was on that night that I fell in love with them.

A month later, I would be removed from the US, much to my dismay. At that point in my life I was bottomed out, didn’t know how to move forward, still lacking meaning and purpose. After a few months of reflection I decided that I wanted to pick up a new skill. I felt comfortable in my knowledge of technology, software development and I felt I understood how to build and grow a business. What I lacked however, was any real world experience in product development. I figured that Teehan and Lax, Cooper or Ideo would be beyond my skill level so I skipped them and looked for a smaller product development shop.

My friend John Leschinski pointed me to an outfit in Toronto called Myplanet and with that, I called. I explained that I wanted to learn product, and that I wanted hands on experience, willing to work for a comparatively small salary to pick up the new tooling I needed. Jason, their CEO liked me and their business was rapidly scaling from 50 people to 100 people. After the interview, he called me and I had a job as a PM on one of their biggest enterprise accounts. Although as fate would have it, after a quarter in product I end up working with the founders on their market position.

I learned A LOT at Myplanet, certainly an experience I’m always thankful for and will never forget. After a little over a year of working with them, my visa issues with the US got resolved and the chance to move back was presented. I emailed Mitch and mentioned I wanted to move back to NYC, noting that DigitalOcean seemed to be doing well. He told me I had four weeks to be in New York, first day October 1st, 2013: Chief Technology Evangelist.

At that time, DO was ~20 people, and yet to take the series A or B partners.

During the years that have followed I’ve been privileged and honoured to work with the DO team as it’s scaled to the ~200 humans we sit at today. Ben, our CEO has been an incredible friend, a mentor, and a great leader to me. I’ve cried in front of him more than anyone else in the world. Moisey and Mitch gave me the freedom to do without question, because of them I’ve grown and learned more than any other opportunity presented on this crazy journey to date. I’ve made some incredible life long friends, I would name everyone but instead you should check out the DO about us page.

Building a company, a business and an organization is really really really really hard. Don’t ever let anyone tell you otherwise.

Jason posted you don’t have what it takes, although I like to believe everyone has what it takes, he’s probably right. Building DO has been one of the most rewarding yet challenging thing I’ve ever done.
When you commit to building something, you give up on a lot to do it, you simply have to.

As far as I can tell, balance when starting up is mostly a myth I’m afraid. As Alex Iskold said:

“Startups are about showing up and following up. Every single day.”

Maybe it comes eventually. I’m just not sure the restless ever stop being restless. The curious continually have to ask why, the dreamers will always dream. Helping to build DO has cost much, but the rewards have been countless and the learnings deep. I am eternally humbled by the road we’ve been privileged to walk together, very few people get the opportunity to do this, we are fortunate. I intend to publish some of the things I’ve learned being a part of the DO team on this blog over the next year.

DO HQ, November 2013.
DO HQ, November 2014.
DO HQ, November 2015.

DO is getting past the startup phase. It’s a real and stable business, with a great team, doing really great things. With that, I see the opportunity to try something new for myself. DigitalOcean is executing on a plan that will unfold over 5 or more years and I truly in my heart of hearts believe that they will dominate the consumer cloud space for decades. I can’t wait to see where they sail the ship, for it is a mighty and powerful vessel, and should not be underestimated.

What am I doing now?

We’re building a team to establish a company that will create a product and, we believe, a business. The focus will be connected devices and IoT, although in a very very specific space. The plan is to have products firmly in market within the next 2–3 years, although I’m sure there will be some pivoting and changes as we discover and explore more.

I’m lucky that I have met some cool + smart people, as a result it was fairly painless to build a really rad founding team to address a massive but fascinating problem..! There has been much interesting in what we’re building, so we’re in the process of closing our seed adventure funding — once that is complete I’ll write more about what we’ll be building together, right now there is much preparation to be done.

Thank you again for all the support and encouragement, promise not to let you down, promise to be worth it, promise to do our best!



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