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YouTube Video VVViQlhMOTNyOTdRdmNqMUFUa2tGNmlBLjB5RkxPNGFlSThB

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

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