SEEING AROUND CORNERS, W/ STANLEY MIDDLEMAN!

We meet again! A happy hello to our loyal readers and listeners, and welcome to a brand new season of TheMikedUp Show! We are so grateful to you and to all the incredible guests we’ve spoken with on our Little Podcast That Could. We wanted to be sure to start Season 4 off with a bang, and boy did we ever! As Founder and CEO of Freedom Mortgage, Stanley Middleman casts a very long shadow in the mortgage landscape. With decades of experience under his belt, Stanley has a lot to say about rolling with the punches that lending can dish out and how to expect the unexpected in this wacky world of ours. Read on for a summary of our information-packed conversation!

Please Subscribe now to our newsletter if this is your first time. Enjoy a preview of the show and Stan's Book.

THE BICENTENNIAL T-SHIRT STORY: LEARNING HUMILITY & RESILIENCE

One of the most memorable anecdotes Middleman shared with us came from his early entrepreneurial days, well before Freedom Mortgage existed. In 1976, during Philadelphia’s Bicentennial celebration, he invested heavily in T-shirt inventory for the city’s crowded streets. Despite a sunny morning, a sudden downpour drenched most of the merchandise, forcing him to salvage and wash thousands of soaked shirts. By the time he had dried them, they had shrunk to sizes nobody wanted. This experience imparted two critical lessons:

Humility is most thoroughly learned not through success, but through adversity. When things go well, we risk believing our success is purely self-made, an illusion that crumbles the moment external forces bring new challenges. Stanley told us that the T-shirt fiasco reminded him that no matter how prepared we think we are, forces beyond our control can change our fate instantly. Also, even though he lost a significant portion of his investment, Middleman points out that the day still resulted in his best single-day earnings up to that point. He embraced the failure, learned from the experience, and remained steadfast in finding solutions.

7:29 - 7:57 -- "Even if you're prepared, major things can happen to you. It's not always you that controls the outcome. And no matter how successful or proud you get or confident, you should have a certain sense of humility, because if you don't, the world will give it to you."

Aidium is redefining mortgage intelligence by helping lenders anticipate borrower behavior before competitors even know they exist. With

AI-driven Propensity Modeling

Aidium analyzes over

5,000 consumer behavior signals daily

to predict who’s ready to transact—months before traditional indicators like credit pulls.

Stop reacting, start predicting! Visit thinkaidium.com to learn more.

Tell Aidium you are "Mikedup" so they know the lead came from us. Especially if you run into Spencer Dusebout or Josh Katz at Booth 327!

TRAIN YOURSELF TO SEE AROUND CORNERS

One of the central messages Stanley emphasized during our conversation is the need to anticipate market cycles. This means staying vigilant and planning for changes in interest rates, housing demand, and global economic forces. Mortgage professionals who want longevity must adopt a forward-looking approach: understanding that rates WILL shift, regulations WILL change, and technology WILL continue to disrupt the status quo. It’s not IF these things will happen, but WHEN.

There’s a critical distinction between trying to “make” the market and learning to “exploit” its fluctuations. Rather than assuming you can force external conditions to your benefit, which just isn’t feasible, Stanley opined that the more productive strategy is to recognize the current environment and leverage the opportunities it presents. For example, when rates are high, an originator might focus on specialized products, or emphasize expert service and guidance that justify stronger margins. Conversely, when rates drop, refi opportunities can take center stage. Either way, you must prepare for surprises. The larger the scale of your operation, the more critical it is to have contingencies for major disruptions. This is a truth that Stanley learned early, both on the job and in life in general.

9:39 - 9:58 -- "I think failure is a wonderful teacher... You can't get a hit if you don't go to bat. And if you go to bat, there are times you're going to strike out. Don't be afraid to fail."

Mortgage Connect, LP 's CEO Jeff Coury and his team are focused on helping lenders evolve, scale and compete. ?At Mortgage Connect, we can help you level up and grow with our robust portfolio of services and digital solutions designed to support the entire mortgage lifecycle. Our tech-forward offerings include title & settlement, default, data and document management, and risk solutions – all of which we can tailor to meet your unique needs. Since our inception more than 17 years ago, our focus has always been to provide innovation, quality, and customer service, with the ultimate goal of delivering an unparalleled consumer experience while reducing compliance risk and ensuring operational excellence at any capacity. To learn how you can take your business to the next level with Mortgage Connect, reach out to us at [email protected].

Tell them you are "Mikedup" so they know the lead came from us!

THE BICENTENNIAL T-SHIRT STORY: LEARNING HUMILITY & RESILIENCE

One of the most memorable anecdotes Middleman shared with us came from his early entrepreneurial days, well before Freedom Mortgage existed. In 1976, during Philadelphia’s Bicentennial celebration, he invested heavily in T-shirt inventory for the city’s crowded streets. Despite a sunny morning, a sudden downpour drenched most of the merchandise, forcing him to salvage and wash thousands of soaked shirts. By the time he had dried them, they had shrunk to sizes nobody wanted. This experience imparted two critical lessons:

Humility is most thoroughly learned not through success, but through adversity. When things go well, we risk believing our success is purely self-made, an illusion that crumbles the moment external forces bring new challenges. Stanley told us that the T-shirt fiasco reminded him that no matter how prepared we think we are, forces beyond our control can change our fate instantly. Also, even though he lost a significant portion of his investment, Middleman points out that the day still resulted in his best single-day earnings up to that point. He embraced the failure, learned from the experience, and remained steadfast in finding solutions.

Floify , the mortgage industry’s leading point-of-sale solution, introduces Dynamic Apps, a no-code feature that customizes loan applications based on loan type, eliminating irrelevant questions and streamlining the borrower experience. By automatically adjusting application fields based on loan purpose—whether purchase, refinance, HELOC, or construction—Dynamic Apps helps lenders accelerate approvals, improve application completion rates, and maintain compliance.

Visit Floify.com to learn more.

Tell them you are "Mikedup" so they know the lead came from us! Do me a favor and subscribe to this newsletter to help us out! Sync up with my good friend and one of the smartest people in mortgage Jason M. at the ICE conference. Set up a meeting with Courtney D. at booth 417! Again, tell them you read about it on the Mikedupshow newsletter.

THE CHANGING ROLE OF REALTORS IN A DIRECT-TO-CONSUMER AGE

One of the more provocative points Middleman raised concerns the future role of realtors in the mortgage process. While real estate agents remain central to many transactions, direct- to-consumer channels are rapidly making inroads. Over the next 5-10 years, he anticipates that a growing number of consumers will bypass the traditional realtor-referral route and instead engage directly with lenders, aided by digital tools and abundant online information. The good news for realtors? There will always be a segment of the market that needs personalized guidance, including first-time buyers or individuals grappling with complex transactions. The value of tailored advice in specialized or emotional transactions remains high. That said, the share of consumers who feel comfortable obtaining mortgages (and even touring properties) without extensive realtor intervention seems poised to rise.

12:59 - 13:33 -- "Sometimes I have to work twice as hard to lose half as much. You know, the reality is that you have to face your environment and make the most of the situation you're in: if it's cost cutting, if it's investing, if it's trying new things, if it's taking small steps and trying to create new products or learn things you don't know. You have to do them in increments that you can handle, so that you can go about the business getting better."

NAVIGATING NON-AGENCY PRODUCTS (W/O LOSING YOUR SHIRT)

A hot topic for many originators is whether to expand product offerings. With traditional refis slowing, some companies have turned to higher-yield mortgage products, from Non-QM and reverse mortgages to DSCR loans and home equity lines. Middleman reminded us that the heightened yields that come with niche products bring proportionally larger risks, especially when market cycles turn. During our chat, Stanley suggested that lenders take a “crawl, walk, run” approach. Expand your credit box incrementally rather than all at once, especially if you’re moving into products supported by private securitization or reliant on aggressive underwriting. The market might reward bold bets when conditions are favorable, but if there’s a correction - as there often is - companies sitting on a massive pile of higher-risk loans could find themselves facing significant repurchase requests and destabilizing losses. While we’ve all learned from the subprime meltdown, it’s easy to forget how quickly exuberance over new loan types can spiral. So be ready to ride the waves and have a Plan B in place.

Enjoy the show on any major podcast here.