I’ve asked a number of entrepreneurs who have benefited from mentors about how they found them, and most did it the old-school way—they asked. “There’s a lot of nice people out there who want to mentor others, many of them because they had also benefited from mentors. All you have to do is ask them,” advises John Bridge, an entrepreneur based in Chicago.¹

It also helps if you display the ambition and energy the young John Bridge did. After a stint in the U.S. Air Force, John enrolled in a local college to study business. While his classmates were competing for top grades as their ticket to job security, John had already learned that no such thing exists. His father had worked for 28 years for the same company until the day the owner decided to sell the business. “My father ended up without a job and with five kids.”

John viewed college as an opportunity to find an area where he could get into business for himself as quickly as possible. One day, a guest lecturer turned up in his real estate class to talk about property tax liens, something that John knew nothing about. The lecturer, a local real estate entrepreneur named Barrett Rochman, explained to the class that municipalities and counties depend on property taxes to bankroll public services and government employees. When a home or business owner doesn’t pay those taxes, eventually the county obtains a lien against the property. If the taxes remain unpaid for a certain period of time, the lien can be auctioned off to private investors willing to pay the taxes immediately to allow the government to have the resources to operate. Investors buy the liens—known as tax certificates—at public auctions by bidding down the rate of interest that the delinquent owner will be charged as a penalty for nonpayment. The lowest bidder wins the certificate, which generally might yield as much as 8 to 10 percent. By all accounts, tax certificates are pretty safe investments, because most taxpayers are inclined to pay off the lien before the penalties add up or they lose their property to foreclosure, which is what happens if the tax liens are not eventually paid off.

Intrigued, John did some calculations on a piece of paper, and after class he approached the lecturer with a proposition. “This looks like a great business. If I’m interested in doing Northern Illinois, would you partner with me?” Impressed by the student’s chutzpah, Rochman warned John that he would have to get very serious about the tax business, studying local laws and procedures as well as the fine points of the real estate business to make sure the properties he was investing in were valuable enough to sell for a profit. Rochman also hit the kid with an even bigger dose of reality: to become a major player in Northern Illinois would require raising about $70 million in capital. John didn’t flinch. “Being a dumb college kid, I figured I could raise the money quickly.”

That didn’t happen, of course. But after graduation, lacking any acceptable job offers, John asked Rochman to take him under his wing. John spent the next two years learning as much as he could about the intricacies of Illinois real estate, tax liens, and sheriffs’ sale businesses while attending local tax sales looking for deals.

At one of the sales, John began talking to an older man in his early sixties who confided that he had invested $150,000 in a local lien company, which didn’t seem to know what it was doing. John became friendly with that man, Joe Somario, and eventually offered to handle those tax certificates and get Somario’s money back, which he did. “I never charged him a dime,” says John, who assumed that his new friend was just another small investor. Somario turned out to be a successful entrepreneur worth millions—and he became John’s second mentor.

Over the next five years, John worked seven days a week with his mentors to build a tax business, including a new design for organizing the data, as he was also learning how to raise the necessary capital. “Yes, I was starting at square one, but I had the benefit of 20 years of experience as a result of having these two mentors behind me who were saying, ‘Maybe you shouldn’t do that,’ or ‘Do this,’” John recalls. “They saved me from wasting a lot of time on mistakes.” John was soon mentoring his less computer-literate mentors on the advantages of building an updatable computerized database of the property tax records around the state, which allowed them to better predict the rate of return on delinquent properties and thus underbid their competitors.

The only thing that they lacked to reach their goal to be the biggest players in the property tax business in Northern Illinois was capital. Then, in 1993, Somario called John about an article he had read “about this guy in Florida who has the opposite problem you have,” meaning he had plenty of capital and was looking for opportunities. His name was Richard Heitmeyer, and he was a 54-year-old entrepreneur who, according to the article, had persuaded Lehman Brothers, the Wall Street investment bank, that he could build a multibillion-dollar business out of buying tax liens. He only needed the capital to establish himself as a nationwide player in a market dominated by local operators. Lehman reportedly had committed one billion dollars.

Somario bought his young protégé a plane ticket to Florida, where John delivered a presentation to Heitmeyer on the property tax business in Illinois. “Two hours later I walked out of there with a handshake agreement that I could do Illinois, with access to $100 million. I know that sounds far-fetched, but it’s the honest-to-God truth,” John recalls, laughing at the memory.

A year later, John and Somario were on the front page of the Chicago Sun Times for having bought the largest single tax certificate in the United States for $7.2 million. It was John’s 30th birthday. By bringing Wall Street money to the auctions, John had helped revolutionize the U.S. tax lien business. Not bad for a guy whose high school guidance counselor told him that he would never be fit for more than a blue-collar job.

John is now a successful entrepreneur with one hand still in the tax lien business and the other launching two new businesses making technological and marketing breakthroughs in radio broadcasting. A risky move for a property tax specialist whose only previous experience with radio was listening to it in the car? Not if you have the right mentor. John’s new mentor is an entrepreneur who has bought, owned, and sold hundreds of radio stations. “I’m learning more about terrestrial radio broadcasting than I ever wanted to know,” he says, laughing. In his free time, John is also mentoring his college-age sons in the art of profiting from property tax certificates and real estate.