Finally, Loveland finds secret to being entrepreneur

The Daily Record
March 20, 2002

“I have a question for you,” he says. “What do you think an entrepreneur is?”

And so begins the Tom Loveland interview. His soft blue eyes peering intently from behind his wire-rim glasses, Loveland awaits an answer to his question, which for the moment serves as his response to a lengthy query about what makes him, as an entrepreneur, tick.

Thomas Loveland, founder of Mind Over Machines, says he has finally discovered ‘the best job in the world.’ Here he boasts the company’s track record with major clients.

Upon hearing the answer — that an entrepreneur is one with a vision and dogged need to see it through — Loveland, founder of Mind Over Machines Inc. among other companies, quickly disqualifies himself. “I agree with that definition, and by that definition I’m only an entrepreneur by half, maybe a third.”

How could he be an entrepreneur when he couldn’t finish college despite attending three of them? When he started his business only because it seemed a faster way to make money than working for a mentally ill boss at a dysfunctional software shop? A job he might have kept had he not needed to repay friends who helped him repay his college loans, which he mistakenly believed had to be paid off all at once?

How could he be an entrepreneur when the only other business he started was a dot-com he created because he happened, just by chance, to own a coveted Web address, then watched in anguish as the business folded? When he could have sold the Web address for $1 million or more and saved himself the trouble?

How could he be an entrepreneur when the person he credits for the success of Mind Over Machines, a custom software shop based in Towson, is a man he hired to run the company day-to-day while he went off and did his dot-com thing?

Series of ‘stuff’

To hear Tom Loveland tell it, life has been a series of Stuff That Has Happened, most of it good, some of it bad, all of it interesting and challenging and growth-inducing, not because he possesses the entrepreneur’s need to build but because he has the academician’s need to learn. If you understand that about Loveland, all the other stuff starts making sense.

Often the smartest guy in whatever room he’s in, he transferred out of the University of Washington’s honors college and into tiny St. John’s College in Annapolis, because St. John’s specializes in Life’s Big Questions and those are the ones he was asking. He left St. John’s for the University of Chicago because he wanted a more “prestigious piece of paper.”

It was a mistake, he now says. The University of Chicago was a fine school for the focused and career-obsessed, but that’s never been Loveland, who is the type who will ace a physics midterm but fail the class because physics just got boring. He never fit in there and he never got the piece of paper; he dropped out.

He then launched his first company, a software builder in Portland, Ore., which failed spectacularly. “It was a joke,” he says.

Needing a job, he came back to Maryland, where an old St. John’s chum told him about a Baltimore software firm that needed someone who could write code. He moved back East and took the gig, but that company, too, was a bit of a joke.

“You hear people say, ‘I have the best job in the world.’ I think I’m headed in that direction.”
– Tom Loveland, Founder, Mind Over Machines

Its owner was [manic depressive and would] lock himself in his house for days at a time. When he was at work, he often openly ridiculed his underlings, whom he called his “minions.” That’s not why Loveland quit, though.

He quit after getting a phone call one night from a bill-collector demanding he repay all of his student loan immediately. It’s true he’d paid nothing since leaving the University of Chicago; [he figured they’d catch up with him one day with a past due statement]. But now his luck had run out, and the bill collector, trained to strike fear in the hearts of the fundamentally well-meaning, had an easy victim in the naïve young Loveland.

Panicked, he raised the money by borrowing it from friends, but he knew he wouldn’t be able to pay them back from what he was earning in his day job.

“This guy convinced me that I’d need to pay all the money now, or I’d be in trouble,” Loveland said in an interview recently in downtown Baltimore. “So I borrowed all the money from friends and paid everything back. Then I quit my job so I could make [more money more quickly and pay] my friends back. … So, that doesn’t sound to me like someone with a ‘vision.’”

Lessons learned

Perhaps not, but Loveland, 41, has been tireless in building his companies ever since, not always with perfect success. Brainstorms, the firm he created to repay his friends 15 years ago, had to be folded in 1989 and reinvented as Mind Over Machines as a way of separating it from Loveland’s former business partner, who, unbeknownst to Loveland, was playing loose with company finances. (Loveland declines to name the partner.)

Tom Loveland, founder of Mind Over Machines, didn’t exactly follow the footsteps of the traditional entrepreneur.

Then in 1999 he started the dot-com, a Web site devoted to motherhood. He started the company after realizing the value of the Web address, which he’d registered years prior for Mind Over Machine’s use.

He said he went to the trouble of launching a company around the brand rather than simply selling it “because it wouldn’t have been as much fun that way.” Still, even if one had good reason to believe all the dot-com hype swirling in the late ’90s, what in the world made this man think he’d have any credibility with moms?

“That was an issue from the get-go” with potential investors, partners and customers, he said. His response was that most of’s employees were “at least female, and a lot were moms,” and that, besides, the company was an online publisher, and lots of publishers have little or no firsthand experience with the subject they’re covering.

Nevertheless,, which had been one of Baltimore’s signature technology firms, [suffered from the dot-com crash of 2000 and] dwindled before folding in early 2001, selling its URL to rival ClubMom for an undisclosed sum. At one point, inquiries into the Web address reached nearly $1 million, and even before Loveland launched, people were offering him “in the low six-figures” for it.

“I could have sold it,” he said. “But I thought, will $100,000 change my life? No. But it was a ticket to meet lots of interesting new people, experience new opportunities, learn, learn, learn.”

What did he learn? After a long pause, he offers a lengthy list.

He learned that some people are not as smart as they seem, that no matter how successful “we all put our pants on one leg at a time.” Getting bad advice from people who seem to know better will teach you that.

He learned the key to effective managing is to be “fast, firm and fair” making decisions, but he also learned that management is not his strong suit.

He learned that in life, nothing will ever happen if you stand on the sideline and never put yourself on the field.

Mind Over Machines is doing well these days. Profitable and fast-growing, the company recently launched a division that sells and installs accounting software and opened a satellite office in Austin, Texas. For this, Loveland credits Ron Monford, the CEO he hired to run the company during his foray into

“I feel very lucky,” Loveland said. “You hear people say, ‘I have the best job in the world.’ I think I’m headed in that direction.”

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