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At any incubator, “the real asset is the mentor,” says Kauffman’s Seguin. But some advertised mentors have so many affiliations—in addition to their own careers—that it’s questionable how much they are really helping. Others may not really be up to the job. “In the technology sector, we believe there are not enough mentors right now,” Seguin says. “It’s an easy title to throw around.”

The scarcity gets more acute the farther a company is from Silicon Valley. For startups in the rest of the country, it can be hard to find the advice needed for success. “We just have to spend a lot of time on airplanes,” says Ben Milne, 25, founder of Dwolla, a fast-growing online payment-processing portal that is based in Des Moines, Iowa.

A dropout from University of Iowa, Milne started his first company at 18 and says he quickly learned the value of connecting to more experienced entrepreneurs. “We kept running around in circles, failing to think big,” he says. “It was a problem I was determined not to repeat.” He now maintains a stable of older advisors both in California and locally.

Any startup would be lucky to find a mentor as well connected as Paul, who is chairman of the San Francisco investment company Top Tier Capital Partners. Forty years ago, as the manager of the fortune of a wealthy family, Paul supplied initial capital to several now-legendary venture capital outfits, including Kleiner Perkins Caufield & Byers and New Enterprise Associates.

He and Hering met after Paul hired Hering’s mother to redecorate his home. At the time, Hering and two dorm mates at the University of Southern California had developed a digital sniper gun that could eavesdrop on a cell phone from a mile away. The toy caused a media sensation, but when they showed it to Paul, he knew right away that it wasn’t a business. “We soon shifted our discussion toward mobile security … a huge, wide-open market,” says Paul.

Hering proved to be an expert listener—perhaps the most gratifying trait a mentee can possess. “What attracted me … was a combination of John’s vision, energy, and, as contrived as it may sound, the fact that he was not in it for the money,” says Paul. “And what kept me engaged is his genuine eagerness to learn.”

After investing some of his own capital into Lookout, Paul set up meetings with investors in Silicon Valley and coached Hering on how to negotiate. Hering played his own role to perfection—he’d start meetings by hacking into the VCs’ cell phones, a demonstration that security was a growing problem for mobile devices.

The company eventually got the attention of big-name funds such as Khosla Ventures and Andreessen Horowitz. They, along with other investors, have put $75 million into Lookout, which has contracts with mobile carriers such as Verizon, Sprint, and T-Mobile. About one million users download a free version of the Lookout app every month.

All that means Hering now has even more mentors. Lookout’s corporate board is packed with important business figures. “Having grown up reading about people like Marc Andreessen and now to have them guiding me is incredibly lucky and humbling,” he says. “I don’t think I can ever outgrow my mentors.”

Antonio Regalado contributed reporting to this item.

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Credit: Gabriela Hasbun

Tagged: Business, Business Impact, business

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