Raising Square’s Jim McKelvey Credit: Jim McKelvey

Raising kids in a digital world is a challenge for almost every parent. We decided to ask the parents of kids who grew up to disrupt the tech world what it was like to raise their kids and what advice they’d give to today’s parents. This is the second in an occasional series called “Raising Tech Stars.”

Jim McKelvey Sr., wasn’t sure what his son was going to be when he grew up. For a while, he thought he might be an architect. He was good with building blocks. Then he thought he might become a lawyer. He had a way with words. He even thought he might become an economist. Wrong again.

As it turns out, McKelvey’s son, Jim McKelvey Jr., grew up to found the groundbreaking mobile payment company, Square, with another tech star, Twitter’s Jack Dorsey.

And though the senior McKelvey, a professor of chemical engineering and college dean, didn’t envision the future, he wasn’t surprised at how it turned out.

"Engineers are typically in the problem-solving business," McKelvey, Sr., said. “If you ask Jim about his ideas on technology, he always says, 'I’m in the problem-solving business.'"

Square solved a big problem for anyone who wanted to find a way to sell items while not being tethered to a traditional credit-card processing machine. It created a mobile payment system that set the stage for a major e-commerce disruption.

McKelvey’s foray into entrepreneurship started long before Square. In college, for example, McKelvey, now 48, decided to write a programming textbook. He started a digital publishing company,  a company that made compact disc storage cabinets and another that evolved into a digital publisher. He also opened his own glass- blowing studio, which still exists today.

Lately, McKelvey has been working on a new project, a not-for-profit aimed at connected beginning coders with companies that are looking to hire them. Called LaunchCode, the effort is based in St. Louis and is in the process of placing hundreds of coders in jobs.

[Read more about LaunchCode]

McKelvey believes his adventures in entrepreneurship are less of a career and more of a journey from business to business, working on whatever interests him at any particular time. He doesn’t worry about whether he’s ever done anything like it before.

“You can’t call what I have a career,” he told BusinessNewsDaily. “I typically move from industry to industry. When I start succeeding, I leave. I get bored. I have doubled down a couple of times. Done a couple of technology companies. I don’t see any industry barriers, particularly.”

That kind of free-spirited embrace of interests is something McKelvey believes he learned from his late mother, Edith, a former journalist and public relations professional.

“[My] mother was fearless. She wasn’t afraid of anything and had an attitude that was infectious. She believed that anything was possible,” he said. “Mother instilled idea that I could do anything. It wasn’t explicit. She never told me any of this. That’s just how she lived.”

It was how she died, however, that changed the way he lives his life now. McKelvey said that before his mother ended her own life without having shown any outward signs of depression, he believed there was no such thing as a problem that couldn’t be solved. After his mother’s unexpected and shocking death, he realized how wrong he was.

“It made me a lot more sensitive to what the real problems are,” McKelvey said. “Before Mom died, I liked to talk a lot. I never interrupt anybody now. I am keenly aware of the fact that I’m not seeing everything. When I’m processing and interpreting, I just see a version of the truth. It’s not real.”

Though it was acquired at an unthinkably high price, it’s a skill that has served McKelvey well.

“I’m supremely aware of my potential to be wrong at all moments,” he said. “That didn’t exist in my world up until Mom died.”

If McKelvey’s younger self was influenced by his mother, however, his more mature self is trying to act a lot more like his father.

“My father is one of the most exceptional people I’ve ever met in my life,” he said. “He has no ego. He’s never tried to prove anything. Never tried to show off.  He’s got a way of avoiding problems that is totally different than Mom’s.

"Mom would just barrel into stuff.  That’s totally my M.O.,” he said. “Dad’s waters are never turbulent for him. It’s amazing to watch.”

McKelvey said that whenever he’s in trouble, he asks himself what his father would do in the same situation.

“The answer is always the same,” he said. “My father would not be in this situation. That’s when I fall back on mom’s skill set.”

For his part, the elder McKelvey doesn’t believe he had a whole lot to do with his son’s success.

“My own nature is not to try to micromanage anything,” he said. Whatever his son had turned out to be would have been fine with him, he added.

“We were always very cautious,” McKelvey Sr., said. “But he has a mind of his own.”

Often, his father wasn’t sure about his son’s plans, but he trusted his son’s instincts and tried not to inflict his own opinions.

He laughs remembering when he first heard about the company that would end up being called Square.

When McKelvey told his father that he would be working on founding Square with Jack Dorsey, his father said, “Who’s Jack Dorsey?” When Jim said Dorsey founded Twitter, his father said, “What’s Twitter ?”

The senior McKelvey said he realized pretty quickly, however, that Square might be a big deal. And, as it turned out, at least that prediction was a good one.