
Through Humor and Humility, CEO and LeBow Students Connect at Real Estate Event
Good advice transcends generations.
It was clear from close to the start of the first event in LeBow’s Henderson Real Estate Institute Speaker Series featuring Stanley C. Middleman, founder and CEO of Freedom Mortgage, the largest mortgage lender in the United States.
By the end of Middleman’s fireside chat-style conversation with Henderson Real Estate Institute director Carter Murdoch, PhD, he had dozens of undergraduate students hanging on his every word.
While sharing anecdotes and stories, some of which can be found in his recent book, “Seeing Around Corners: Achieving Success in Business and Life,” Middleman stressed business fundamentals, awareness of the markets and recognizing opportunities, but many of his remarks were both off-the-cuff and of-the-moment.
A Philadelphia native from a modest, working-class background in Northeast Philadelphia, Middleman majored in accounting at Temple University, though he notes he never worked in the field. His foundation in accounting principles, though, yielded a ready grasp of numbers and the willingness to dig into them and find meaningful patterns.
He recalled his early-career days working in insurance sales, when he would examine his success rates and compared them to the time he spent preparing and to the minutes he spent on his sales calls. This method shaped his approach to data as a leader later in his career: “If you can’t measure it, you can’t manage it.”
In his responses to questions from Murdoch and, afterward, from students, Middleman came across as humble and humorous yet driven, describing himself throughout his career as “too dumb to quit, too dumb to know when I’ve won.”

His frank and personable style clearly resonated with student attendees, and the unlikely connection between a senior-level executive with over 40 years of experience and a lecture hall full of mostly undergraduate business students yielded long lines afterward to take photos and have book copies signed.
Nick Bucci, a first-year student majoring in finance and business analytics, felt Middleman came across as honest and humble in spite of his prominent position and track record of business success.
“I felt like he genuinely wanted to help us as students and to teach us things,” he says. “He made things very easy to understand and didn’t sugarcoat anything.”
That candor came through in Middleman’s advice in navigating uncertainty, built from his experiences during the subprime mortgage crisis and global recession of 2008-09 and earlier moments of instability.
“You have to face change and say, ‘bring it on’,” he says. “Stay sensitive to and aware of your surroundings, and keep an eye on the exits.”
Beyond the real estate industry and related financial matters, Middleman freely shared influences on his thinking from outside the business world — notably, novels like “War and Peace” and “Atlas Shrugged” — and bite-sized history lessons on changes in society and business all the way back to the Industrial Revolution.
“People don’t get led — they choose to follow,” he says. “So be a leader: run for the position of leader every day, and get elected every day.”