How I Made It: Chris Nicholson traveled a meandering path from Big Sky Country to CEO of AI start-up Skymind

Chris Nicholson, 42, is chief executive of Skymind, an artificial intelligence company in San Francisco that’s vying with dozens of other start-ups to emerge as a major player in the nascent AI economy. Google, Amazon, Apple, Facebook and other tech giants now dominate “deep learning” AI, powering such things as voice-activated personal assistants, image recognition and driverless cars.

Skymind has built open-source programs and assembled a team of experts to help organizations smaller than Google or Apple build their own deep-learning programs. Thousands of start-up wannabees would love to have Skymind’s funding — $6.3 million from venture capitalist hotshots such as Ray Lane’s GreatPoint Ventures and China’s Tencent Holdings Ltd.

Embrace new experiences

“Montana is a beautiful place, with a lot of wonderful people,” the Montana native said. “But if there’s one adjective you’d use to describe it, it’s remote. For anybody born curious in Montana, the first task is ‘how to expose myself to the world.’”

At 17, he was selected for the Rotary Youth Exchange program and traveled to the German state of Bavaria, where he developed a love for Europe. He attended Deep Springs College near Bishop in the California desert, with a student body of 26, “a place of intense intellectual ferment, where you also learned how to do things with your hands.”

He learned meditation living at the San Francisco Zen Center, where he also volunteered at its AIDS hospice. A “wild dude” he met there persuaded him to relocate to Guatemala, where he helped addicted street kids get off glue.

To explore the income gap between rich and poor countries he studied economics at American University of Paris. “It turns out most of economics doesn’t really care about that,” he said.

Take the best of what’s at hand

Nicholson fell in love with an Argentine dancer at the Moulin Rouge. An Argentine reporter lured him into journalism. He pestered the International Herald Tribune for 10 months before the newspaper finally hired him.

His next post was with New York Times’ DealBook section. He worked out of an apartment at the top of the small tower that cinema buffs will remember from the apartment building in “Last Tango in Paris.” After two high-stress years, Bloomberg hired him on the mergers and acquisition news team.

At each job, he picked up different skills. “I learned basics of reporting at the Herald Tribune. At DealBook I learned to write stories. At Bloomberg I learned how to get scoops.”

Know when to quit

In the wake of the Great Recession, journalism “didn’t feel very healthy,” Nicholson concluded. “I saw the newspaper business suffering so much,” he said. “I thought, tech did this to journalism, and I don’t want to be on the receiving end of this. I want to be on the other side of the code.”

He learned Javascript and Python programming. That didn’t make him a coder but did lead to a public relations job in San Francisco at FutureAdvisor, a robo-investing company acquired by BlackRock in 2015 for $200 million.

He lived in a hacker house as “one snoring guy in a room with five other snoring guys.” There he met Adam Gibson, in his early 20s, a master hacker, Nicholson said. Together they started Skymind in 2014.

Always keep learning

Gibson handled the technology. Nicholson ran everything else: recruiting, team building, fundraising, documentation, incorporation documents, contracts.

“I’m not saying I did any of it great. But I had to do it well enough to keep the whole ship afloat,” Nicholson said. “Good enough is the key word. At least one co-founder needs to be at least good enough at about a dozen different things.” That frees up the programmers to work toward technical perfection.

Failures are rehearsals

“When you’re creating and starting a start-up you’re making lots of mistakes,” he said. “You get the opportunity to make mistakes and learn from them. When you found a start-up, if your job description doesn’t change every three months or so, you’re doing something wrong.”

The first year of pitching for funds didn’t go too well. But “all those failed pitches to investors were in fact rehearsals that prepared me for the successful pitches I would eventually make.”

A start-up is a community

Now that Skymind has grown to 35 employees, spread across the globe, Nicholson is focusing on team building. “Building a company means talking to people a lot. It’s an extremely social occupation. I might prefer to read some crazy technical document, but that’s not what I need to be doing.”

He draws on lessons in building consensus in structured environments that go way back to his experiences at Deep Springs College and the San Francisco Zen Center. “Direct democracy doesn’t seem to be working anymore, but it does still work at a small level,” he said.

Take chances

Nicholson said he encourages Skymind employees to take chances in matters small and large.

“Every single time you jump off the cliff, you land someplace unexpected,” he said. “It never turns out like the dream you had, but you needed the dream to get there.”