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About This Podcast
Dealmaker$ is a long-form podcast for operators — the people who make decisions, deploy capital, and carry real risk.
Each episode features candid conversations with real estate professionals, business owners, investors, and leaders who have built and operated in the real world. The focus isn’t hype or motivation, but judgment, execution, and the moments where deals were won, lost, or nearly unraveled.
Through origin stories, market perspective, and deep dives into signature deals and pivotal decisions, Dealmaker$ explores how real businesses and real real estate actually work. If you operate, build, or invest — this show is built for you.
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Recent Episodes
Dealmaker$ | Brad Walsh (Part 2)
What does it actually take to scale a local professional services firm without losing its identity?In Part 2 of Shane’s conversation with Brad Walsh of Eagle Title, the focus shifts from transactions…
Dealmaker$ | Brad Walsh (Part 1)
What really happens between contract and closing?In this episode of Dealmaker$, Shane sits down with Brad Walsh of Eagle Title to unpack the part of real estate most agents and buyers never fully see…
Dealmaker$ | Compass Acquires Anywhere
Residential real estate is on the brink of a structural reset—and the proposed Compass acquisition of Anywhere Real Estate may be the catalyst.In this episode of Dealmaker$, Shane Hall unpacks what…
Dealmaker$ | Broker Wars
Real estate isn’t just changing—it’s consolidating, centralizing, and lawyering up.In this episode of Dealmaker$, Shane Hall unpacks the most consequential real estate power moves shaping Maryland…
Dealmaker$ | The Death of the Starter Home
For decades, the starter home was the gateway to the American Dream. Today, it’s largely gone—and the reasons go far beyond interest rates.In this episode, Shane unpacks why first-time buyers are…
Dealmaker$ | Travis Gray
Some real estate careers are built on momentum. Others are built in the aftermath.In this episode of Dealmaker$, Shane sits down with Travis Gray, one of Maryland’s most respected waterfront…
Dealmaker$ | John-Mark Bolton
In this episode of Dealmaker$, Shane sits down with John-Mark Bolton, co-founder of ClearDefense Pest Control — one of the fastest-growing home-services companies in America, now operating in 30+…
Dealmaker$ | Kristi Neidhardt
Sustainable success in real estate is rarely about volume alone—it’s about trust, intention, and relationships that compound over time.In this episode of Dealmaker$, Shane sits down with Kristi…
Dealmaker$ | Lynlea Westervelt
In this Dealmaker$ episode, Shane sits down with Lynlea Westervelt, one of Maryland’s top loan originators, Scotsman’s Guide-ranked producer, former college athlete, and now a senior leader at First…
Dealmaker$ | Jennifer Chino
In this episode of Dealmaker$, Shane sits down with Jennifer Chino — a former Microsoft, Sony, and Motorola executive who pivoted into real estate after a terrible experience buying her own home, and…
Dealmaker$ | David DeSantis
Luxury real estate at the highest level isn’t about volume—it’s about judgment, positioning, and trust earned over time.In this episode of Dealmaker$, Shane sits down with David DeSantis, Co-Chief…
Dealmaker$ | Nikki Foard
In this episode of Dealmaker$, Shane sits down with Nikki Foard, Senior Vice President at Compass and one of the most respected recruiting leaders in the region. Nikki brings a rare combination of…
Dealmaker$ | Jason Garey
Reinvention is a skill—and elite performers learn it early.In this episode of Dealmaker$, Shane sits down with Jason Garey, MLS Cup Champion with Columbus Crew, University of Maryland standout, and…
Dealmaker$ | Justin Santini
In this episode of Dealmaker$, Shane sits down with Justin Santini — a seasoned multifamily operator turned full-stack construction founder. Justin brings a rare blend of institutional real estate…
Dealmaker$ | Betty Batty
This episode of Dealmaker$ features a powerhouse in Maryland luxury real estate: Betty Batty, founder of Hello Home of Compass and one of the region’s most trusted agents. Known for her white-glove…
Dealmaker$ | Jamison Mullen
Great lending careers aren’t built overnight—they’re built through consistency, credibility, and showing up when it matters most.In this episode of Dealmaker$, Shane sits down with Jamison Mullen, a…
Dealmaker$ | Ryan Brassel
Commercial real estate rewards clarity, patience, and execution—and very few brokers sustain all three across market cycles.In this episode of Dealmaker$, Shane sits down with Ryan Brassel, Principal…
Dealmaker$ | Sean and Jen Degnan
Short-term rentals reward operators who think like hoteliers—not landlords.In this episode of Dealmaker$, Shane sits down with Sean and Jennifer Degnan, co-founders of iTrip Vacations Annapolis, to…
Dealmaker$ | Matt Nader
In this episode of Dealmaker$, Shane sits down with Matt Nader, President of First Home Mortgage, to break down one of the most compelling leadership journeys in the mortgage industry. Matt joined…
Dealmaker$ | Danny Cantwell
In this episode of Dealmaker$, Shane sits down with Danny Cantwell, a veteran title attorney at KVS Title whose career spans more than 24 years and over 16,000 settlements. Danny’s path is one of the…
Frequently Asked Questions
Dealmaker$ has published 20 episodes since December 2025, covering topics in Business, Entrepreneurship.
Dealmaker$ is currently dormant with new episodes hourly. Average episode length is 1h 1m.
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