Seeing Around Corners ft. Stanley Middleman

10 snips

Feb 24, 2025

Stanley C. Middleman, Founder and CEO of Freedom Mortgage, shares his journey in the mortgage industry and his commitment to community service. He discusses the 7 Principles that guide his entrepreneurial mindset and reflects on how failures can teach valuable lessons. The conversation shifts to the importance of adaptability in volatile markets and how adversity can lead to reinvention. Stanley also reveals that his insights were initially documented for his children, emphasizing the significance of leaving a legacy.

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ANECDOTE

Bicentennial Downpour

Stanley Middleman recalls selling souvenirs in Philadelphia on July 4, 1976.
A downpour ruined his merchandise, teaching him a valuable lesson about humility.

ADVICE

Embrace Failure

Embrace failure as a learning opportunity.
Don't be afraid to take risks and "go to bat", even if you strike out sometimes.

INSIGHT

Exploiting Opportunities

In your 20s, view the world as full of opportunities, like Stanley Middleman did with his disco deli and mortgage ventures.
Focus on exploiting existing market opportunities rather than trying to create new ones.

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Link to buy the book : https://amzn.oia.bio/ks235
Find the 7 Principles here : https://postimg.cc/RNrn3WST

In this Season 4 premiere of The MikedUp Show, hosts Michael Kelleher and Michael Zau welcome Stanley C. Middleman, Founder and CEO of Freedom Mortgage—one of the nation’s largest full-service mortgage companies. Titled “Seeing Around Corners,” this episode shines a spotlight on Stanley’s approach to entrepreneurship, resilience, and purposeful action.

Stanley reflects on his decades-long career—beginning with Freedom Mortgage’s founding in 1990 and growing it into a top U.S. originator and servicer. He also discusses his commitment to community, having served on non-profit boards like the Children’s Hospital of Philadelphia and the Kimmel Center for the Performing Arts. Along the way, Stanley has navigated market swings and regulatory complexities, championing the idea that true success involves “doing things on purpose.”

During the conversation, you’ll hear about:

The 7 Principles that form the backbone of Stanley’s entrepreneurial mindset
Moments of unexpected change—from restaurant ventures to major mortgage industry pivots
The importance of maintaining a forward-thinking (“seeing around corners”) perspective in volatile markets
How adversity can spark reinvention, provided you’re dedicated to consistent, strategic effort
Why Stanley first documented his insights for his children and grandchildren, and what it means to leave a legacy of knowledge

From recognizing revenue-generating activities to mapping out your week in advance, Stanley’s guidance offers practical tools for professionals and dreamers alike. You’ll also get behind-the-scenes anecdotes about learning from mistakes, negotiating with challenging landlords, and staying resilient when everything seems to “rain down” all at once.

Beyond running a thriving business, Stanley remains deeply engaged with industry boards. He’s served on the Mortgage Bankers Association Residential Board of Governors (RESBOG), as well as advisory boards for Freddie Mac, Fannie Mae, and Ellie Mae. His numerous awards—including recognition as a top CEO by South Jersey Business Magazine—further underscore his influence on the mortgage landscape.

Prepare to discover how Stanley Middleman’s experiences can help you anticipate challenges, optimize your strategy, and strengthen your leadership approach. Whether you’re a loan officer, an entrepreneur, or simply someone who loves hearing success stories, you’ll find this chat both enlightening and inspiring. Stanley proves that real growth, personal or professional, rarely happens by accident—it’s the result of measured planning and an unwavering commitment to progress.

Sponsored By: Mortgage Connect
Be sure to visit Mortgage Connect for comprehensive mortgage solutions that streamline processes and optimize your lending operations. Their cutting-edge services mirror the innovative spirit we celebrate on The MikedUp Show.

Join Michael, Michael, and Stanley for this deep dive into purposeful leadership, staying ahead of the curve, and building a lasting legacy—starting now, on The MikedUp Show!