John-Mark Bolton went from a broken-hearted college soccer player to a commission-only sales assassin to co-founder of ClearDefense Pest Control — scaling the company from zero to 30+ markets through grit, leadership, and a relentless door-to-door sales culture. In this Dealmaker$ episode, he breaks down his origin story, the principles behind ClearDefense’s explosive growth, and the mindset needed to build something massive.

TTR Sotheby’s COO David DeSantis joins Dealmaker$ to share his 20-year journey in DC real estate, from Capitol Hill and the FTC to shaping one of the most respected luxury brokerages in the country. We dive into leadership, negotiation, ultra-wealthy buyer behavior, major trophy deals, DC politics, and the trends defining the Mid-Atlantic market.

Jason Garey went from scoring goals for the University of Maryland and winning an MLS Cup to starting from scratch in financial planning — building a multi-niche advisory firm that now serves athletes, business owners, and retirees. In this Dealmaker$ episode, he shares the real story behind reinvention, discipline, confidence, leadership, and the mindset required to build something new after the stadium lights go out.

Justin Santini went from managing 5,000+ units in the DMV to launching one of the region’s most forward-thinking full-service construction companies. In this episode, we break down the mindset, systems, and lessons that shaped him — from turning around distressed assets to designing modern, turnkey homes. If you care about operations, vision, and execution in real estate, don’t miss this one.

Jamison Mullen went from bartending and beach-living in Charleston to becoming one of the most trusted mortgage leaders in Annapolis. A former D1 lacrosse player, father of six, and branch manager at USA Mortgage, Jamison brings a rare blend of competitiveness, loyalty, and operational toughness. In this episode, Shane digs into his rise, his leadership style, and what separates elite lenders in today’s market.

Ryan Brassel is one of Maryland’s most active commercial real estate dealmakers — moving 50–60 deals a year and advising clients from local owners to major institutions. In this episode, Shane digs into Ryan’s path from Fairfield lacrosse to Detroit sales to Rosso CRE partner, plus the strategies, trends, and stories behind the Maryland commercial market.

Before becoming one of Maryland’s premier waterfront agents, Travis Gray was a ski-obsessed college kid, a Discovery Channel producer, a Jerry Bruckheimer assistant, a documentary filmmaker, and the co-owner of a 60-employee post-production studio that collapsed in 2008. In this Dealmaker$ episode, he shares how he rebuilt from nothing, became a Coldwell rookie eating venison three nights a week, and grew into a respected Annapolis market leader.

Kristi Neidhardt didn’t grow up dreaming of real estate — she grew up wanting to help people. From AmeriCorps and nonprofit leadership to surviving 9/11 in New York and eventually becoming a top producer and team leader in Annapolis, Kristi has helped nearly 700 families through calm, values-driven, client-first service. This is her full story.

Compass Senior Vice President Nikki Foard shares her journey from scrubbing warehouse floors in her dad’s industrial company to becoming one of Compass’s most trusted, referral-driven recruiters. We break down her early setbacks, her people-first strategy, her pitch style, and how she built a recruiting engine based on relationships, values, and real results.

Matt Nader went from Johns Hopkins athlete to loan officer in 2006, survived the 2008 collapse, and rose to President of First Home Mortgage in just six years. In this episode, Shane digs into Matt’s journey, the evolution of the mortgage market, and the strategies, systems, and leadership lessons behind one of the most respected lending operations on the East Coast.

Former D1 athlete and Scotsman’s Guide top originator, Lynlea Westervelt, breaks down her journey from Columbia, MD to becoming one of the most trusted mortgage pros in the region — sharing mindset, systems, leadership lessons, and the real strategies behind helping families win in a brutal market.

Sean and Jen Degnan turned a franchise bet during the early days of COVID into one of the most respected short-term rental operations in the Chesapeake region. From historic Annapolis homes to waterfront estates, they’ve built iTrip Annapolis through hospitality, data, Navy-community ties, and hyper-local service. In this episode, we unpack their journey, their systems, and the wild stories behind the business.

Sean and Jen Degnan turned a franchise bet during the early days of COVID into one of the most respected short-term rental operations in the Chesapeake region. From historic Annapolis homes to waterfront estates, they’ve built iTrip Annapolis through hospitality, data, Navy-community ties, and hyper-local service. In this episode, we unpack their journey, their systems, and the wild stories behind the business.

Jennifer Chino began her career as a Microsoft technical trainer, helped launch the Sony Memory Stick and Motorola’s Push-to-Talk tech, and eventually pivoted into real estate — where she built a boutique, client-obsessed business in Annapolis. In this Dealmaker$ episode, she shares her origin story, her biggest wins, her philosophy, and the lessons that shaped her 20-year career.

Danny Cantwell has closed more than 16,000 real estate transactions and is widely known as one of the most trusted title attorneys in the DMV. In this episode, Shane digs into Danny’s journey from ACC tennis champion to KVS Title attorney, the biggest title issues agents overlook, and the wild stories, legal insights, and practical advice behind smooth (and not-so-smooth) closings.

Betty Batty is one of the most trusted luxury and waterfront agents in Maryland — a top 1.5% producer known for her white-glove service, strategic negotiation, and referral-driven business. In this episode, Shane and Betty break down her path from nonprofit leadership to founding Hello Home of Compass. They get into mindset, client loyalty, market trends, and the habits behind long-term success in high-end real estate.