The education of Jonathan George

Entrepreneur Jonathan George and his wife, Tamaira, photographed Tuesday near Union Station, met through MySpace and were married in 2007. “I liked that he was different, that he liked to take chances,” she said. “Most guys are boring.”
Entrepreneur Jonathan George and his wife, Tamaira, photographed Tuesday near Union Station, met through MySpace and were married in 2007. “I liked that he was different, that he liked to take chances,” she said. “Most guys are boring.” The Wichita Eagle

Jonathan George achieved something very few in Wichita have — and then decided he wanted less of it.

George is one of Wichita’s few honest-to-God, big-time tech entrepreneurs. He has built or helped build four software companies, and has sold a couple of them or parts of them.

He negotiated to land a major investor as he walked the streets of New York. More recently, he flew weekly to San Francisco to build a company.

But he also discovered one of the oldest story lines in literature: There is a price to success.

For a decade he was been willing to pay because that’s who he is. And, because his wife, Tamaira George, loved him for it.

These days, at age 33 and between companies, he has become the occasionally prickly elder statesman for Wichita’s developing tech scene. He co-founded an angel investment fund, Angels of the Plains; has spoken at local conferences and panels on entrepreneurship; and has agreed to mentor aspiring entrepreneurs.

George is 5-feet-4 and whippet thin, and he literally vibrates with nervous energy. He speaks rapidly, his thoughts firing out, and he is thoughtful and bracingly honest — or irritating and arrogant, depending on your point of view.

His attitude is part of his worldview, in which he sees himself as a full-fledged member of the global tech scene, often more at home culturally in Silicon Valley or New York than in Wichita.

It’s that knowledge and those cultural values that he hopes will help his hometown as it works to develop its own entrepreneurial tech scene.

“I think a lot about what I can leave, how I can share what I’ve learned, because it’s critically important to the future of Wichita,” he said.

“What we are missing right now is people who are stepping up and not playing in their own little kingdom and instead working collaboratively to build this entire city.”

A small-town kid

George is from Coffeyville, arriving in Wichita in 2006. He started in 2005 building StikiPad, an app where people could write on a common document.

It only reached, in the vernacular of the industry, “ramen stage,” where it generated just enough income to keep a mythical graduate student operating the site on cheap noodles. It was nearly bought by Twitter, he said, which was enough to hook him on tech entrepreneurship. He shut it down in 2007.

He met Tamaira in 2006, through MySpace, and they got married in 2007.

They are pretty well matched personality-wise. She describes herself as introverted, stubborn, not shy nor always diplomatic. His focus and drive appealed to her.

“I liked that he was different, that he liked to take chances,” she said. “Most guys are boring.”

In 2009, he built the app that would later become Boxcar, his biggest success. The app notified iPhone and Android phone consumers, and later commercial users, of incoming messages and notifications.

He sold it in 2012 when the business was growing but living on financial fumes. He paid the last two payrolls out of his own pocket and borrowed money for a third to keep it afloat. He and his investors later sold it for a large, undisclosed amount.

Their daughter, Penelope, was born that year. In fact, his daughter’s birth inspired a story that George ruefully tells on himself: With his wife in labor at Wesley Medical Center, he was in the room, on his phone, conducting negotiations to secure a life-saving investment in the company.

Tamaira George said she was fine with that. It was early on in the labor, she said.

He sold it in the morning on July 13, and by nightfall, he said, he had started work on his next company, Evomail.


It was a mistake to jump back in so quickly, he said. Tamaira said she wanted her husband to take a few months off, rest, relax, spend some family time.

“I think she expected it,” he said of starting the new company. “(But) in retrospect, I should have taken time off. It takes a lot out of you.”

By 2013, he and a couple of co-founders, Dave McGraw and Dominic Flask, were working 16- or 18-hour days in a space in a converted warehouse south of Intrust Bank Arena.

Evomail was an attempt to revolutionize e-mail, which was based on software from the 1980s. But making basic improvements to e-mail was always going to be difficult, which is why it is still virtually unchanged after more than two decades.

By late 2014, George grew more and more stressed as Evomail struggled technically and started running low on money. As he struggled to secure funding, the company ran out of money.

Bad blood developed among the partners and contractors amid the collapse, with some finger pointing over who got paid and who didn’t.

The crash

That was George’s low point. He looked and felt like hell. He was exhausted, stressed, depressed, haunted by failure.

There was strain in the marriage, Tamaira said, but it wasn’t broken. Her husband just needed to rest, relax and figure some things out.

Wichita has a small tech community, filled with gossip, she said. People figured they were splitting.

“Our relationship wasn’t dysfunctional,” she said. “That’s the thing. A lot of people think they know a lot of things about how this happened, what happened. And they actually don’t.

“We’re both fairly private people and just let it go. What happened is he just wore himself out. He was pushing himself too hard.”

George said that after the company folded, he sent out e-mails to everyone, apologizing. He has since partially repaid the contractors who didn’t get paid, he said.

He reconnected with one of his old partners, Flask, who had started working for DropBox in San Francisco. They met out there months later, talked and mended fences.

“I wouldn’t call it bad blood at all,” said Flask, who has since returned to Wichita. “We were trying to find out some information, and it was tough. He and I worked through everything. He apologized.”

The good news, George said, is that he later sold the Evomail app, paid off his investor, then bought back some of the assets and sold those again, making some money for himself. It took some of the sting out, but he still considers it a failed company.

George connected with a friend, Brian Alvey, in early 2015 and was chief technology officer at Alvey’s company, Recurrency, a San Francisco company that created a platform for donors to give recurring donations to artists.

The workload was lighter, George said, but he had to fly to San Francisco weekly. The company couldn’t establish its market position, and George left in January after a dispute over the direction of the foundering company.

Alvey pulled the plug on it in February.

“We had an excellent, productive time building Recurrency together,” Alvey wrote in an e-mail. “Then I pivoted the business into something new and he’s back in Kansas doing his own thing.”

What he learned

The lessons he learned, George said, sounds suspiciously like a tech version of “stop and smell the roses.”

He used to do his best work between 2 and 6 a.m. Now he goes to bed at 10:30 p.m. so he can work for a few hours in the morning before he gets his daughter up.

They watch cartoons and eat breakfast together before she heads off to preschool. On Fridays, they share breakfast at Doo-Dah Diner or Spangles.

He’s Mr. Mom while his wife works as a digital marketer at Copp Media Services.

He admits to growing up some. He’s still a tech entrepreneur, still obsessive, still prickly. He’ll try to build more companies in the future.

But he says he has learned that his family is the ground that he wants to stand on when he does it. He learned that he needs more balance in his life.

“I built companies with this weird notion that I would find happiness in that company,” George said. “That is all I’ve literally done since I was 12, chasing this one thing.

“And you find out once you start to have it that it’s not that answer to” happiness.

Dan Voorhis: 316-268-6577, @danvoorhis