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Tech Life

How Teleport’s Leader Transitioned from Engineer to CEO

Ev Kontsevoy loves talking to other engineers, but after he sold his first startup he knew he needed to learn more about leadership before starting another company. He shared his story on the Tech Founders Odyssey podcast.
May 4th, 2023 10:14am by
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The mystery and miracle of flight sparked Ev Kontsevoy’s interest in engineering as a child growing up in the Soviet Union.

“When I was a kid, when I saw an airplane flying over, I was having a really hard time not stopping and staring at it until it’s gone,” said Kontsevoy, co-founder and CEO of Teleport, said in this episode of the Tech Founder Odyssey podcast series. “I really wanted to figure out how to make it fly.”

Inevitably, he said, the engineering path led him to computers, where he was thrilled by the power he could wield through programming. “You’re a teenager, no one really listens to you yet, but you tell a computer to go print number 10 … and then you say, do it a million times. And the stupid computer just prints 10 million. You feel like a magician that just bends machines to your will.”

In this episode of the series, part of The New Stack Makers podcast, Kontsevoy discussed his journey to co-founding Teleport, an infrastructure access platform, with TNS co-hosts Colleen Coll and Heather Joslyn.

Teleport, which was co-founded by Taylor Wakefield and Alexander Klizhentas, began in 2015 as a company called Gravitational. In May 2022 it announced it had raised $110 million in a Series C funding round, bringing its total raised to $169 million — and its post-money valuation to $1.1 billion.

This funding round included participation from Insight Partners; The New Stack is a wholly-owned subsidiary of Insight.

‘My Customers Are Other Engineers’

While the former USSR was “a fairly dark place to grow up,” Kontsevoy said, it was a culture in which science and technology were revered. The tech founder still carries that spirit with him, he said:  “All of my childhood heroes, they’re mostly engineers and scientists.”

A post-college job at National Instruments, based in Austin, Texas, gave him lots of interaction with other engineers, and a desire to surround himself with people from that world.

At trade shows and conferences, Kontsevoy said, other engineers “would ask you questions about the product that you built. And you get to ask them questions about what they’re building. And I would meet petroleum engineers, aerospace engineers, I would meet the engineers that built all the things around that surrounds us. It was fascinating. You get to learn how the world works.”

As a result, he added, “I wanted to have a job where my customers were other engineers. I wanted to be connected to this kind of broader community.”

That desire, he said, led him to entrepreneurship:  “I was so focused on building something that other engineers would love to use.”

An earlier startup, Mailgun, which was required by Rackspace in 2010, proved to be a learned experience, he said.

“I never transitioned from being an engineer to being a CEO. So I kind of got stuck in this cycle of talk to customers, go build. And I started to neglect that the company itself needs building.”

Kontsevoy realized, he said, “that I needed to step back and learn how to be CEO before I start another company again.”

Learning How to Be the Boss

Teaching himself how to run a company took time and a change in mindset, away from coding and toward more delegation to his team, with more focus on issues like scaling the business.

“If I told you that I never Googled ‘how to be a CEO,’ I’d be lying,” he said.

While acknowledging that learning leadership skills is a personal journey that will be different for everyone who undertakes it, Kontsevoy said three things helped him: books, meeting people who had expertise he didn’t have, and mentorship.

About leadership and management books, he advised listeners to “try to spot patterns. Because not every piece of advice is applicable to you … advice generally has limited utility because it has an expiration date. And it is also contextual; what worked for a person in certain circumstances back then might not necessarily apply to you.”

He praised the mentorship of leaders from Rackspace, the company that acquired his first startup, as being helpful in guiding his journey.

“CEO is a lonely job,” he acknowledged. “You can’t really complain too much. There is a lot on your mind that it’s not OK to share with other people until we develop a sense of clarity. So having someone that you can be relaxed about asking for advice and bounce ideas off, is incredibly helpful. I do recommend first-time CEOs to have someone who’s been in their shoes that they can actually be open with.”

Check out the full episode for more on Kontsevoy, how he works with his co-founders, raising money, finding product fit and establishing an organizational culture.

Like this episode? Here are more from The Tech Founder Odyssey series:

How 2 Founders Sold Their Startup to Aqua Security in a Year

How Solvo’s Co-Founder Got the ‘Guts’ to Be an Entrepreneur

Feature Flags Are Not Just for Devs

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TNS owner Insight Partners is an investor in: The New Stack, Aqua Security, Teleport.
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