The Madison Podcast

From Sleeping in His Car to Top Long Island Agent | Jason Orsini's Real Estate Mindset

What does it take to go from living in your car to becoming one of the most respected real estate agents on Long Island? In this episode of the Madison Podcast, Ben Lavender sits down with Jason Orsini, a Douglas Elliman agent with nearly two decades in the business, known for winning deals in one of the most competitive housing markets in the country. Jason shares the raw story behind his success. From losing his teaching job during the recession to cold calling from a phone book, knocking on doors, and grinding his way to Rookie of the Year. He opens up about adversity, family struggles, the mindset that fuels his relentless work ethic, and the strategies he uses today to win bidding wars and close deals when others cannot. This conversation is equal parts real estate strategy, life philosophy, and high performance mindset. What You'll Learn in This Episode • How Jason went from unemployment during the recession to Rookie of the Year • The exact strategy he uses to win bidding wars in competitive markets • Why relationships and communication win more deals than price alone • How adversity shaped his discipline and relentless drive • The mindset behind balancing success, family, and long term wealth Key Takeaways (Timestamps) 0:00 Introduction to Jason Orsini 1:00 Losing his teaching job during the recession 2:00 Setting the goal to sell 20 homes in year one 4:00 Winning Rookie of the Year 5:00 Living in his car and overcoming adversity 7:30 Proving success to his father 9:00 Massive vision and long term goals 10:00 Parenting and building generational wealth 17:00 How to win bidding wars in competitive markets 20:00 The strategy of humanizing buyers in offers 23:00 Why terms matter as much as price 26:00 Why relationships between agents win deals 28:00 Why "highest and best" is the lazy negotiation tactic 31:00 Jason's 3:30 AM daily routine and competitive mindset 33:00 Balancing success, business, and family Let's Connect Host Ben Lavender Instagram: https://www.instagram.com/blavmtg @blavmtg Guest Jason Orsini Instagram: https://www.instagram.com/jason_orsini @jason_orsini Madison Mortgage NMLS #1862796 Instagram: @madison_mortgage

How a 21-Year-Old Realtor Built his Business with Max Cassamajor

What does it take to build a real estate career before most people even graduate from college? In this episode of the Madison Mortgage Podcast, host Ben Lavender sits down with rising agent Max Cassamajor of Power Move Realty to unpack what it's really like starting young, building confidence, and turning social media into a lead machine. Max shares how his very first deal came from a simple Instagram reel… with only $2/day in advertising — proving you don't need to go viral, you need to be visible. This conversation is full of mindset shifts, tactical takeaways, and hilarious door-knocking reality checks. What You'll Learn in This Episode * How Max got his first real estate client from a $2 Instagram ad * Why consistency beats talent in building a pipeline * The gym mindset that applies directly to business growth * How to handle rejection (and keep knocking anyway) * Buyer vs seller expectations in today's market Key Takeaways + Timestamps 00:00 – "Max Major" Meets Ben Lavender A fun intro + how cultural connection builds trust 03:00 – Starting Real Estate at 18 Why beginning young can be a massive advantage 05:00 – The $2/Day Instagram Strategy Max's first deal came from boosted content, not cold luck 10:30 – Door Knocking Horror Stories Rejection, resilience, and accidentally calling someone "boss"… twice 14:00 – The Power of Follow-Up Why most agents lose deals simply by disappearing 19:00 – Buyers Are Too Picky, Sellers Too Greedy Real talk on today's mindset gap in negotiations 23:00 – Realistic Expectations Win Deals Why the "perfect house" doesn't exist (even in new construction) Let's Connect Host: Ben Lavender Instagram: @blavmtg Guest: Max Cassamajor (Power Move Realty) Instagram: @maxmajor.realty If you're a realtor, loan officer, or ambitious young professional trying to grow your business the smart way — this episode is for you. 👉 Like, subscribe, and drop a comment: What's the best lead source you've ever tried?

How Discipline, Door Knocking & Belief Built a Real Estate Machine with Mike Petit Frere

What happens when you stop waiting for the market to change and decide to outwork it instead? In this episode of The Madison Podcast, host Ben Lavender sits down with Mike Petit Frere of Power Move Realty, a New York real estate agent whose business exploded during one of the toughest markets in recent history. Mike shares how failing his real estate exam 11 times, nearly losing his life in Miami, and being written off by others became the fuel that built his success. If you're in real estate, sales, or entrepreneurship and feel stuck, this episode is a punch in the chest—in the best way. What You'll Learn in This Episode -How Mike built consistent business when rates were high and deals were scarce -Why door knocking (yes, really) became his unfair advantage -The exact daily discipline that changed his income and mindset -How to convert cold leads without sounding salesy -Why proving people wrong can be dangerous—but powerful if used correctly Key Takeaways & Timestamps 00:01:00 – Failing Forward 00:02:00 – Making the Market Work for You 00:04:00 – The Power Position Shift 00:05:00 – Rejection Therapy 00:07:00 – Disarm Before You Sell 00:09:00 – Cold Calling Without the Cringe 00:13:00 – The 12-Hour Workday 00:18:00 – When Business Saves Your Life 00:23:00 – The Miami Wake-Up Call 00:27:00 – From Party Guy to Professional 🤝 Let's Connect Host: Ben Lavender Instagram: @blavmtg Guest: Mike Petit Frere Instagram: @mikesupersales 🎧 Subscribe for more real conversations with industry leaders who've actually done the work. Madison Mortgage NMLS #2537109 Visit us at www.madisonmortgage.com

From Survival to Service: Real Estate, Responsibility & Building Generational Wealth with Omar Jones

When responsibility comes early, and excuses aren't an option… what do you do? On this episode of The Madison Podcast, Ben Lavender sits down with Omar Jones of Power Move Realty to share a story shaped by resilience, purpose, and relentless drive. From growing up without basic necessities to creating pathways for others to achieve homeownership and generational wealth, Omar's journey is candid, insightful, and full of practical lessons for anyone ready to take ownership of their life. This is a candid conversation about discipline, mindset, and accountability—showing that opportunity isn't handed to you, it's built by you. Why This Episode Matters - Too many people wait for perfect conditions. - Too many people confuse comfort with safety. - Too many people believe their past disqualifies them from a better future. Omar's story dismantles all three, offering a roadmap for taking responsibility, embracing discomfort, and creating your own success. What You'll Learn - How early responsibility and adversity build discipline, resilience, and leadership. - Lessons from Omar's grandparents on accountability, "no excuses," and getting things done. - Turning life challenges into opportunities to serve others and create generational wealth. - Practical strategies for financial literacy, credit, and building a foundation for homeownership. - How mindset shifts, embracing discomfort, and learning from failures accelerate growth. Key Takeaways & Timestamps 00:00 – 01:00 | Introduction & Early Career Choices 01:00 – 03:00 | Lessons from Family Legacy 03:00 – 06:00 | Childhood Challenges & Early Responsibility 06:00 – 09:00 | Caregiving & Life Shifts 09:00 – 12:00 | The "No Excuses" Mindset 12:00 – 16:00 | Turning Adversity Into Service 16:00 – 21:00 | Practical Financial Guidance 21:00 – 25:00 | Mindset Shifts & Energy Alignment 25:00 – 28:00 | Embracing Discomfort & Learning from Failure 28:00 – 30:00 | Mentorship & Systems for Success 30:00 – End | Closing Thoughts & Inspiration Let's Connect Host: Ben Lavender Instagram: @blavmtg Guest: Omar Jones, Realtor, Power Move Realty @getlistedwithmrjones If this episode sparked something for you—share it with someone who needs to hear it. Growth travels faster when it's shared.

Relationships Will Always Beat AI in Real Estate with Dylan Bugallo

What does it really take to succeed in real estate today — without the fluff, the fake motivation, or the "post-and-pray" strategies? In this episode of The Madison Podcast, host Ben Lavender sits down with Dylan Bugallo, a high-producing New York real estate agent known for his no-nonsense, relationship-first approach. Together, they unpack what actually moves the needle in real estate — from prospecting fears no one admits out loud to why most agents stay busy but broke. This is an honest, unfiltered conversation about doing the work, caring deeply, and building a business that lasts. What You'll Learn in This Episode - Why real estate can feel lonely — even when you're surrounded by people - How Dylan built a referral-driven business without relying on AI or gimmicks - The difference between looking busy and actually producing results - How to instantly build trust in listing appointments (without scripts) - Why relationships will always beat automation in real estate Key Takeaways & Timestamps 00:01 – The Lonely Agent Paradox: Why real estate feels isolating — and how events, mentors, and proximity to talent change everything. 00:07 – Mindset Before Metrics: Why burnout kills more careers than rejection — and how rest actually improves production. 00:12 – The Trust Advantage: How simple human behaviors (listening, respect, curiosity) win listings over flashy pitches. 00:17 – Facing the Fear No New Agent Admits: Why rejection isn't the real fear — and what actually stops agents from prospecting. 00:21 – The 33-Touch Rule Explained: How consistent, genuine follow-up turns past clients into long-term referral engines. 00:27 – Busy ≠ Productive: Why podcasts, AI tools, and motivational content don't matter if you're not calling people. 00:29 – Why Dylan Hates Open Houses: A brutally honest breakdown of time ROI, lead quality, and when open houses actually make sense. If this episode resonated with you, share it with someone who needs the reminder: 👉 Care more. Work smarter. Build relationships that last. 🤝 Let's Connect Host: Ben Lavender – New York's Favorite British Mortgage Broker 📸 Instagram: @blavmtg Guest: Dylan Bugallo – Real Estate Agent, Over South 📸 Instagram: @dylanbugallo Follow @madison_mortgage for more related content. 🎧 Subscribe for more real conversations with industry leaders who've actually done the work. Madison Mortgage NMLS #2537109 Visit us at www.madisonmortgage.com