How Stan Middleman's past informs Freedom Mortgage's future

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Freedom Mortgage CEO Stan Middleman has distinctive insight into housing finance that few can match, according to people in the mortgage business who know him and his organization.

Middleman is "a true industry leader" and particularly well-known in the City of Brotherly Love,  said Kevin Kauffman, the Philadelphia-based head of client engagement at Freddie Mac.

"I get to interact with that organization on a day-to-day basis, and they're truly focused in a way I think some others are not," he said.

The Freedom executive's insights were the key to his successes, which among other things afforded him partial ownership of the Philadelphia Phillies baseball team. But it took a lot of time - and mistakes - to get to where he is now.

Freedom Mortgage CEO Stan Middleman and Chip Hunter, dean of Temple University's Fox School of Business and the School of Sport, Tourism and Hospitality Management
Photo by Joseph V. Labolito, Temple University.

Middleman recently acknowledged early career struggles in an interview about his new biography, "Seeing Around Corners." He was in Denver to discuss it at the Mortgage Bankers Association's annual convention at the time, just prior to the election.

The memoir penned by NMN columnist and analyst Chris Whalen, extends from Middleman's younger days when he attended Philadelphia's Temple University and later ran a "disco deli" to how he utilized mortgage servicing rights to help build Freedom's business.

It's a tale that Whalen said reflects a more entrepreneurial time for the business.

"Stan is one of the last examples of a large firm that was grown organically by accumulating MSRs and without passive capital from Wall Street," said the author, who forecasts a pending nonbank capital rule will bar small firms from doing this in the future the way Middleman did.

Middleman is "an eyewitness to the rebirth of nonbank finance in America in the 1990s. And he survived a number of challenges and financial crises, a testimony to him and his veteran team," Whalen added. 

When asked about some of the more dramatic moments in his life, such as when he dealt with a threat of violence at work or a failed business, Middleman said, "I don't think I would change a thing.

"We are all prisoners of our own experience, and we're all [an amalgamation] of the things that we live through. Everything that ever happens to you has a part to play in the person you become," Middleman said.

What follows is an interview with the Freedom Mortgage executive, condensed and edited for clarity.