Ben Uretsky and the business of making less work

Ben Uretsky had already built a business when he discovered that being good at it was an awkwardly incomplete qualification. ServerStack kept customers’ websites running. It had servers, employees, revenue and the accumulated knowledge of years spent making other people’s software behave. Yet prospects kept choosing Rackspace. Uretsky could improve the machinery. He could improve the service. Persuading a customer to reconsider a familiar name was another engineering problem altogether.

That frustration became the starting point for DigitalOcean. The company would enter a market occupied by Amazon, with ambitions that might reasonably have earned a sympathetic pat on the shoulder. Uretsky and his fellow founders had a more precise proposition: make the cloud understandable to the developer trying to get something built. The size of the competitor mattered less if the customer wanted a different experience.

There is a pleasing inconvenience in this story for anyone who believes technical competence speaks for itself. Uretsky had technical competence. What changed his career was learning how to make a promise people could understand.

The education that started before the degree

Uretsky was born in Russia and moved to the United States at five with his family, including his brother Moisey and a grandmother. He grew up in Brighton Beach, Brooklyn, attended Stuyvesant High School and later graduated from Pace University. The brothers would eventually build companies together, carrying a relationship formed long before either had a job title into the decidedly less predictable business of becoming employers.

Ben began working at 15. He taught himself Linux, networking and servers, then worked in technology businesses spanning internet telephony and hosting. He has described earning his bachelor’s degree partly as a way of showing his father he could finish college. The practical education had already begun. By 21, before graduating, he was starting his first business.

ServerStack, founded in 2003, offered managed hosting: the watchful work of keeping a customer’s online operation available, backed up and able to handle demand. Its appeal to Uretsky included the economics. Customers who succeeded needed more infrastructure. Their growth could expand the relationship over time. It was an attractive reason to care whether someone else’s business was doing well.

A good business with an uncomfortable view

By 2011, ServerStack managed about a thousand servers around the world and employed roughly twenty people. This was a functioning operation with experience and paying customers. It also offered Uretsky a close view of two different competitive problems. Rackspace had established a strong association with support. Amazon Web Services threatened to change how customers bought infrastructure altogether.

Better equipment and a lower price did not automatically loosen Rackspace’s hold on the customer’s imagination. Meanwhile, even a victory over a hosting rival would leave the shift toward cloud computing to contend with. Uretsky and his colleagues began asking what they would build if they could start again.

They read about marketing and positioning. A business could choose its hardware, its pricing and its feature list; it also needed to choose the place it hoped to occupy in a buyer’s mind. DigitalOcean began taking shape in 2011 and incorporated in March 2012. Its founding team included Ben and Moisey Uretsky, Jeff Carr, Alec Hartman and Mitch Wainer.

“It feels like I’m working for the man,” but I was the man.

Ben Uretsky, recalling ServerStack in a 2016 conversation

The joke has a useful sting. Founding a company had not exempted him from feeling trapped by its limitations. Starting again meant carrying forward the operational knowledge while rethinking the offer. His first business had supplied a livelihood and an apprenticeship. It would also help supply the next company’s early resources.

Five founders, three bedrooms

The customer research had a distinctly New York catering budget. The team visited startup offices with pizza, asking technology leaders for advice. A slice bought a conversation; the conversations helped sharpen the product’s focus. A developer with an application to launch had different immediate concerns from a large organization assembling an elaborate infrastructure operation.

The route into Techstars was less straightforward. DigitalOcean applied to the New York program, made it through several stages and was rejected. David Tisch subsequently suggested Boulder. In May 2012 the team was accepted, and five founders moved into a three-bedroom house in Colorado. There are probably more comfortable ways to establish a division of labor.

Uretsky later remembered rehearsing for demo day in the backyard with Wainer. The audience would be about a thousand people, many of them investors. A friendly technology meetup and a room assessing your business are different kinds of public speaking. The preparation included a Karate Kid reference from Wainer: “Wax on, wax off.” Apparently even cloud infrastructure benefits from a training montage.

The house makes an appealing origin scene, but it is the continuity beneath it that matters. These founders had already operated infrastructure. The accelerator added pressure, mentors and relationships. Uretsky later credited Techstars with helping connect DigitalOcean to its Series A investor, Andreessen Horowitz. A network was becoming part of the company’s equipment.

The cloud still needed a kitchen table

On January 15, 2013, DigitalOcean introduced its SSD virtual machine offering. Uretsky remembered daily signups moving from a couple to more than a hundred. He also remembered the founders sitting at a kitchen table, manually installing solid-state drives in servers to meet demand. The cloud had acquired a domestic address and a decidedly physical workload.

The lesson in that scene is wonderfully literal. Customers could experience a service as simple because someone else was doing the complicated work. The neat interface did not eliminate procurement, installation or capacity planning. It made those responsibilities the provider’s problem.

By August 2016, Uretsky was describing a platform with more than 700,000 users. Growth had also delayed the expansion of its product range: keeping up with demand for the original Droplet required time spent organizing supply chains and operations. Selling something people want creates an entirely fresh opportunity to disappoint them if delivery cannot keep pace.

Uretsky’s explanation of the economics was equally concrete. DigitalOcean bought its equipment while using outside providers for the data-center space. Hardware financing helped support expansion. The customer saw a virtual machine; the company had to make the physical and financial pieces fit. A cloud business can have an airy name and a very earthbound balance sheet.

A million users, and the work between them

In July 2017, DigitalOcean announced one million users. Uretsky’s account of that milestone spent time on the people around the product: contributors writing tutorials, answering questions and eventually joining the company. The community had produced more than 1,600 tutorials. Helping someone solve an installation problem could be part of introducing them to the platform.

He singled out people such as Jonathan Tittle, an early adopter who spent hours helping other users troubleshoot before becoming a platform support specialist. The relationship could move from customer to contributor to colleague. Documentation and discussion gave developers a reason to return even when they were not buying another server.

Inside the business, the problem was changing too. Early software had depended heavily on co-founder Jeff Carr. A growing engineering organization needed shared understanding, documentation and structures that could support more people. Uretsky described organizing teams around products such as Droplets, storage and networking. The founder’s work increasingly concerned how other people could work together.

At a 2019 conversation, the scale was plain: DigitalOcean had recorded $200 million in revenue in 2018 and had about 500 employees. Those figures belong to a particular period, rather than serving as a description of the company today. They show how far the founding proposition had traveled in seven years.

The critic learns to arrive earlier

Uretsky’s account of his own leadership is more revealing than a string of growth figures. In 2018, he acknowledged a reputation around the office for finding what was wrong with a proposed plan. Spotting weaknesses is a useful occupational habit for someone responsible for infrastructure. It can make the meeting room feel rather different from the server room.

He wanted to participate earlier, helping colleagues develop a plan instead of arriving with a list of defects. He also valued job candidates who could teach him something or offer an unfamiliar perspective. There is a coherent adjustment here: a technically experienced founder learning to leave room for knowledge he does not already possess.

His smaller preferences were suitably specific. Google Docs appealed because people could collaborate and discuss ideas in context. The Entourage theme song brought back memories of Boulder. These details put an ordinary working person inside the founding story: someone with a preferred tool, a familiar soundtrack and habits he was still trying to improve.

Leaving the chair, keeping the connections

In February 2018, Uretsky announced that DigitalOcean would look for his successor. In June, he introduced former Citrix chief Mark Templeton as the next CEO. He described a need for experience in scaling operations and evolving the company’s approach to the market. The company reported a $200 million run rate at the announcement. A run rate describes an annualized pace; it should not be confused with revenue already recorded.

Uretsky’s later work took him into both founding and investing. He co-founded Welcome Homes, which sought to let customers arrange the construction of a home online, from finding a lot to choosing a design. Several familiar DigitalOcean collaborators were involved. By 2021, he was also among Vantage’s seed investors, alongside Moisey and Wainer. Vantage was working on cloud-cost visibility, a problem adjacent to the infrastructure world they knew.

His public professional profile now lists Sky Ventures, and a colleague’s 2024 account described running its operation and working with him again. The connections have lasted beyond one company and one executive position. People who once shared an office have become repeat collaborators, founders and backers.

Look back from those later relationships to ServerStack, and the enduring subject is attention: to the customer’s decision, to the developer’s time, to a colleague’s contribution. Uretsky’s career turned when he stopped assuming a capable service would explain itself. DigitalOcean gave that lesson a product. The people who built it gave it somewhere to go.