From the Fall 2011 Oregon Stater

By Kevin Miller

Bert Sperling is big on the benefits of failure.

Today, the 1972 business graduate makes a nice living helping people decide where to live or to find manly men or to get a great night’s sleep.

He has built a small empire out of his ability to employ science and a bit of whimsy to, as he says, “add quality to data,” and then present his results in ways that help people make important life decisions or maybe just give them a few laughs and garner attention for Sperling’s clients.

A fun example, he said, was when the giant Mars food corporation wanted publicity for its Combos snacks – “the official cheese-filled snack of NASCAR” – and turned to Sperling’s BestPlaces.

“Combos wanted me to rate the manliest cities, with ‘manly’ being sort of tongue-in-cheek, because Combos is a salty snack and men love salty snacks,” Sperling said. “I guess women are too smart to eat those sorts of things.”

Sperling and his staff analyzed factors like the number of home improvement stores, steakhouses, pickup trucks and motorcycles per capita, and the proximity to race tracks, drag strips and major sports venues. Circulation of magazines like Sports Illustrated, Car & Driver and Popular Mechanics boosted a city’s manliness ratings, while magazines like Vanity Fair, Martha Stewart Living and Vogue were deemed “manly Kryptonite” and lowered the scores.

In consecutive years, Sperling named Nashville, Tenn., and Charlotte, N.C., as the manliest cities in America, with Portland – his longtime home – finishing 47th out of 50 the first year and dead last in 2010.

When a reporter asked Sperling if it made him nervous to walk around the city after he had named it “least manly,” he smiled and responded that if his ratings were correct, he had little to worry about.

“I mean, what are they going to do to me?” he said.

Other customers at Sperling’s BestPlaces include well-known consumer brands like Pepto-Bismol, which hired him to list the best places for Thanksgiving dinner (winner Akron, Ohio); Baileys Irish Cream, which wanted a list of America’s “most chill” cities (winner Portland), and Edge Shave Gel, which asked him to name the 10 most irritated cities (winner Atlanta).

His client list is a roll call of major corporations and publications. His books sell well. His online analysis tools are offered on his website – – and licensed to other sites across the Internet. With the tools, people trying to find their own best place can compare customized ratings for hundreds of communities based on criteria they choose. If a person wants a list of medium-sized cities with low crime, great schools and a healthy appreciation for the arts, Sperling can produce it.

He and his wife and business partner, Gretchen Sperling, enjoy a comfortable but not ostentatious life in a restored 1920s home in Portland’s quiet Eastmoreland neighborhood. They also have a place on the coast at Depoe Bay. Their two grown sons are developing careers in show business in Southern California.

Sperling’s BestPlaces is both highly successful and extremely lean. World headquarters is a small room upstairs from the family kitchen. The entire corporate motor pool is in the driveway – a Honda Odyssey van and a Honda Fit subcompact. All five Sperling’s BestPlaces employees work out of their own homes or personal offices.

The founder’s approach to financial security – indeed to life in general – is that of a man who enjoys good fortune but never takes it for granted.

During a recent chat with students at Weatherford Hall as a visiting fellow at OSU’s Austin Entrepreneurship Center, Sperling spoke of his early struggles. He warned the students that it takes a lot more than a good idea and a willingness to work hard to make it as an entrepreneur. He urged them to be brave and bold and persistent, and not to be hyper-focused on getting perfect grades and avoiding mistakes at all costs.

“If you want to succeed you really have to be willing to fail a lot,” he advised the would-be entrepreneurs. “If you really feel uncomfortable with that – with trying something that might fail – that’s something you have to push over and get past.”

Sperling arrived at OSU as a freshman in the tumultuous late 1960s. He thought he wanted to pilot a Phantom fighter-bomber in Vietnam, so he took Air Force ROTC classes for his first two years. Told that his eyesight would prevent him from being a pilot, he abandoned his military aspirations but didn’t replace them with a particular drive to do anything else.

“I figured a job was just going to come,” he said. “I guess I was sort of fat, dumb and happy at that age.”

He took classes that satisfied his curiosity, including a home economics course that explored the scientific aspects of cooking, and a Shakespeare class in the Department of English. “I didn’t know it was going to be advanced Shakespeare for English majors, so it was a little more of a challenge than it should have been.”

He graduated from the College of Business in 1972 as an industrial engineer and went to work for Freightliner Corp. in Portland.

“There was a huge layoff and I got laid off because I was one of the recent hires. Now, looking back, I realize we were in a huge recession at the time, but I don’t think I understood the role the greater economy was playing in the troubles I was having. It kind of went on like that. Later I worked for an accounting firm – I was going to get my CPA license – and they went under.”

He found himself with a wife and two sons to support, but without a clear plan for financial stability.

“After getting laid off from different jobs, I thought ‘Well, I’ll take matters into my own hands,’ so I worked at home, writing business software. I was more confident than I should have been.

“It was more unusual to work at home in those days. People thought I must be selling Amway or something like that. One guy asked me, ‘What makes you get out of bed in the morning if you don’t have to go in to work?’ and I said, ‘Well, there’s the mortgage bill and the grocery bill and the power bill and …’”

The family scraped by. Sperling wrote a piece of software that helped analyze data for making decisions, and his clients talked him up to their professional colleagues. That earned him a small mention in USA Today, which in turn led to more work.

“I was doing studies for magazines and PR firms,” he said. “We weren’t starving, but we had no certainty about what was going to come in, or when it was going to come in. I remember once Gretchen said, ‘We should have a budget.’ I said, ‘Let’s talk about that,’ and she said, ‘How much money do we make a month?’ and I said ‘I have no idea.’ That sort of ended the budget discussion.

“With Gretchen’s encouragement, I put some of my software on the Internet so people could get it there. People found it and started coming to me.

“This is something I tell students today. A great thing about the Internet is that if you have something people can use, and you make yourself known, when they’re ready to spend money they can find you. Otherwise, if you’re just going around asking people to spend money when they’re not ready to spend money, that’s a waste of their time and your time.

“I’ve never had to spend a dime on marketing,” he said. “I like to joke that my approach is to sit aggressively by the telephone.”

He also tells students that once that call comes – “Today, of course, it’s an email and not a phone call” – they’d better have a product that works as advertised, and they’d better be consistently reliable so they can build a reputation for integrity.

“One day a call came from some engineer at Microsoft, and he said, ‘Hey, we’re working on a real estate site and we really like your content, and we’d be interested in licensing it. How much would you want for it?’”

Sperling laughs and shakes his head at the memory of that day in 2000. He figured it would be sweet to get Microsoft to pay an annual fee of “something in the five figures.”

“It’s one of those moments in your life,” he said. “You don’t want to say too much because you want to see what they’re going to offer. So after a little back and forth, we had an idea of what kind of figure they were looking at, and it was five figures – a month.

“And that,” he said, “was really great. I remember I walked downstairs to the kitchen and I said, ‘Honey, I think we might have a business model.’”

As media reaction to his studies began to raise his profile, Sperling’s knack as a performer became a major asset. A talented guitarist and singer, he was a member of The Sawtooth Mountain Boys, a regionally famous country-bluegrass band, while at OSU. Today, he still plays gigs as a country-swing crooner named “Hank Sinatra.” Samples of Hank’s work are available at

Gretchen, who met her husband-to-be when she went to a performance hoping to connect with another guy in the band, provides both tangible and intangible support for the family business.

She remembers how much fun it was when Sperling’s BestPlaces listed the worst places for flea problems for Hartz Mountain pet products. Little Rock, Ark., was deemed the most hospitable city for fleas, which led to a television bit by Jay Leno in which the Miss Arkansas pageant winner was crowned with a flea collar instead of a tiara.

While Bert Sperling seems to have plenty of fun at work and away from it, he is zealous when it comes to protecting his reputation for doing good work.

“When a company hires me for one of these studies, they trust me with their brand, because they’re going to want me to go to the press and talk about it,” he said. “I’m honored by their trust, and it often makes me the beneficiary of a million dollar ad campaign. That in turn makes it more desirable for other companies to license my material, because of the profile I have, and the credibility, and it grows from there.

“Everybody has a brand,” he said. “I like to think a brand is an emotional connection to who you are and what you do. I take care of my brand.

“I feel very lucky, but I also believe that the harder you work, the luckier you get.”

Kevin Miller, ’78, is editor of the Oregon Stater.

More info on the Entrepreneur in Residence Nov 1 event