Ten Questions with Ben Uretsky, Founder & CEO at DigitalOcean

In this series, FirstMark gets personal with outstanding entrepreneurs and CEOs, with quick interviews on their stories, likes, dislikes and ambitions.

Ben Uretsky knows market positioning is a crucial consideration for an early startup. In cloud computing, dominated by giants like Amazon and Google who were largely catering to the needs of enterprises, Ben decided to focus on an underserved market: the developer. Fast forward several years and DigitalOcean is now one of the largest and fastest growing cloud services platforms in the market. With over one million users worldwide, and millions more turning to their online community for tutorials and content, DigitalOcean delivers simplicity, ease and expert knowledge to developers.

Tell us the origin story of you becoming a founder.

The story of DigitalOcean actually starts in 2011. I launched my first company, ServerStack, a managed hosting provider, but despite having newer hardware and superior support at a lower cost, we were losing out to the competition. In addition to battling against the market leader, we also saw a new threat on the horizon — Amazon Web Services. It didn’t take long to realize the potential of AWS, and that this new business model was going to disrupt the industry.

How did you respond?

In light of this, we knew we needed to take a step back and recalibrate. We believed cloud was the new way to build modern day web applications, but we needed to find a unique value proposition. To better understand the needs of developers building the next generation of companies, we went door-to-door in New York’s startup district with boxes of pizza to talk with CTOs, offering up a slice for every piece of advice. We used all that feedback to form DigitalOcean’s focus: we create elegant, simple solutions at scale that developers love.

What was your lowest/hardest time as a founder and how did you get through it?

In early 2012 while we were still trying to secure funding, it was suggested that we apply for Techstars New York. The only issue: the deadline was 24 hours away. We hunkered down and pulled everything together, securing ourselves a coveted invite to the Techstars intro day. We had a great pitch, but unfortunately did not make it into the program.

We were certainly disappointed, but knew we’d given it our best. A few weeks later we received an email from David Tisch, who was running the NYC program at the time, and he suggested we apply to the Boulder program. Tisch explained he was impressed with our pitch, but didn’t feel that his experience in the server and infrastructure space would be beneficial, since he had more of a consumer background, and decided to reject our application.

Two months later, in May 2012, we were accepted into the Boulder program and moved our five-person team to a three bedroom house. It was a gruelling time, but with no other distractions we were able to focus on our product, meet many mentors and ultimately build a product and business model that got us to where we are today.

What advice would you give your younger self, the self who first started the business?

I think it’s common for early-stage startups to get caught up in the product and strategy and forget about the most important part of a business — the people. When I first started DigitalOcean I couldn’t imagine that it would grow so quickly to the size it is today (400 employees and counting!). Over the years I’ve learned the importance of attracting the right talent and creating an environment that helps them thrive and do their best work. It might be cliché to say, but it’s all about the people — they are the ones who build the company.

What is one quality you look for in team members?

In interviews, I’m most impressed with candidates who can help me learn something new or offer a different perspective. If all of our team members thought the same way, we would glean little value from our conversations. We gain so much more when we have team members who can bring new things to light and help challenge the status quo to make our product and company better.

It’s always exciting to meet a candidate who can actually help you gain new insight into the business that you’ve built from the ground up.

What’s the most important part of your daily routine?

I’ve recently gotten into mindfulness and meditation and I believe it’s critical to a happy and successful day. Tony Robbins advocates for the “hour of power” or if that doesn’t work the “30 minutes to thrive” or even the “15 minutes to fulfillment.” If you can’t fit that in then he says you shouldn’t even bother going to work. I may not be that extreme, but I think taking even 10 minutes to reflect and meditate can make a major difference in how you react to people and situations. It helps you start your day positive and energized.

Favorite work tool?

I love Google Docs because they enable you to both collaborate and converse. In addition to working on content together, you can have contextual sidebar conversations on the concepts being discussed. In many situations, Google Docs can actually replace all of the important aspects of a working meeting — with the added benefit of allowing people to work in real time or asynchronously depending on their schedule and working style. We use Google Docs for everything from product plans and strategy docs to board meeting presentations and agendas.

Favorite personal tool?

I’m a huge fan of the “Sworkit” fitness app. It offers a variety of workout routines on-demand and is perfect for busy people who don’t always have the time (or desire) to go to the gym to fit in a good workout.

I’m an avid Shark Tank fan and this app first caught my eye while watching the show. It was one of the few products that passed my very own “30 seconds to impress” test. I knew it was worth investing in just moments into their pitch!

Where do you find inspiration?

This may sound cheesy, but the Entourage theme song (“Superhero” by Jane’s Addiction) always gets me pumped up to tackle the day. Not only is it a great song (and show), but it reminds me of the old Techstars days back in Boulder with the founding team.

What do you hope to do in 2018 that you have never done before?

As part of my mindfulness practice, my goal for 2018 is to embrace a more positive life perspective. I see this as an important goal both personally and professionally; it’s something I’m working on each day.

In addition to changing my own mindset, I’m also working on helping my team approach all situations — including difficult things like change and critical feedback — in a way that leaves them feeling positive and empowered.

I’m known around the office as the one that’s always pointing out what’s wrong with a presented plan. While that feedback can be useful to avoid pitfalls, this year I’m working hard alongside my team to engage early and build the best plan possible so everyone feels empowered.

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