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

<description>&lt;div class="OutlineElement Ltr SCXW175342908 BCX8"&gt; &lt;p class="Paragraph SCXW175342908 BCX8"&gt;&lt;span class= "NormalTextRun SCXW175342908 BCX8"&gt;What does it take to go from living in your car to becoming one of the most respected real estate agents on Long Island?&lt;/span&gt;&lt;span class= "EOP Selected SCXW175342908 BCX8" data-ccp-props= "{}"&gt; &lt;/span&gt;&lt;/p&gt; &lt;/div&gt; &lt;div class="OutlineElement Ltr SCXW175342908 BCX8"&gt; &lt;p class="Paragraph SCXW175342908 BCX8"&gt;&lt;span class= "NormalTextRun SCXW175342908 BCX8"&gt;In this episode of the &lt;/span&gt;&lt;span class= "NormalTextRun SCXW175342908 BCX8"&gt;Madison Podcast&lt;/span&gt;&lt;span class="NormalTextRun SCXW175342908 BCX8"&gt;, Ben Lavender sits down with &lt;/span&gt;&lt;span class= "NormalTextRun SCXW175342908 BCX8"&gt;Jason Orsini&lt;/span&gt;&lt;span class= "TextRun SCXW175342908 BCX8" lang="EN-US" xml:lang="EN-US" data-contrast="auto"&gt;&lt;span class= "NormalTextRun SCXW175342908 BCX8"&gt;, a Douglas Elliman agent with &lt;/span&gt;&lt;span class= "NormalTextRun SCXW175342908 BCX8"&gt;nearly two&lt;/span&gt;&lt;span class= "NormalTextRun SCXW175342908 BCX8"&gt; decades in the business, known for winning deals in one of the most competitive housing markets in the country.&lt;/span&gt;&lt;/span&gt;&lt;span class= "EOP Selected SCXW175342908 BCX8" data-ccp-props= "{}"&gt; &lt;/span&gt;&lt;/p&gt; &lt;/div&gt; &lt;div class="OutlineElement Ltr SCXW175342908 BCX8"&gt; &lt;p class="Paragraph SCXW175342908 BCX8"&gt;&lt;span class= "TextRun SCXW175342908 BCX8" lang="EN-US" xml:lang="EN-US" data-contrast="auto"&gt;&lt;span class= "NormalTextRun SCXW175342908 BCX8"&gt;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 &lt;/span&gt;&lt;span class= "NormalTextRun AdvancedProofingIssueV2Themed SCXW175342908 BCX8"&gt;opens up&lt;/span&gt;&lt;span class="NormalTextRun SCXW175342908 BCX8"&gt; 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. &lt;/span&gt;&lt;/span&gt;&lt;span class= "EOP Selected SCXW175342908 BCX8" data-ccp-props= "{}"&gt; &lt;/span&gt;&lt;/p&gt; &lt;/div&gt; &lt;div class="OutlineElement Ltr SCXW175342908 BCX8"&gt; &lt;p class="Paragraph SCXW175342908 BCX8"&gt;&lt;span class= "TextRun SCXW175342908 BCX8" lang="EN-US" xml:lang="EN-US" data-contrast="auto"&gt;&lt;span class= "NormalTextRun SCXW175342908 BCX8"&gt;This conversation is equal &lt;/span&gt;&lt;span class= "NormalTextRun ContextualSpellingAndGrammarErrorV2Themed SCXW175342908 BCX8"&gt;parts&lt;/span&gt;&lt;span class="NormalTextRun SCXW175342908 BCX8"&gt; &lt;/span&gt;&lt;/span&gt;&lt;span class="TextRun SCXW175342908 BCX8" lang="EN-US" xml:lang="EN-US" data-contrast="auto"&gt;&lt;span class= "NormalTextRun SCXW175342908 BCX8"&gt;real estate strategy, life philosophy, and &lt;/span&gt;&lt;span class= "NormalTextRun ContextualSpellingAndGrammarErrorV2Themed SCXW175342908 BCX8"&gt;high performance&lt;/span&gt;&lt;span class= "NormalTextRun SCXW175342908 BCX8"&gt; mindset&lt;/span&gt;&lt;/span&gt;&lt;span class="NormalTextRun SCXW175342908 BCX8"&gt;.&lt;/span&gt;&lt;span class="EOP Selected SCXW175342908 BCX8" data-ccp-props="{}"&gt; &lt;/span&gt;&lt;/p&gt; &lt;/div&gt; &lt;div class="OutlineElement Ltr SCXW175342908 BCX8"&gt; &lt;p class="Paragraph SCXW175342908 BCX8"&gt;&lt;strong&gt;&lt;span class= "TextRun SCXW175342908 BCX8" lang="EN-US" xml:lang="EN-US" data-contrast="auto"&gt;&lt;span class= "NormalTextRun SCXW175342908 BCX8"&gt;What &lt;/span&gt;&lt;span class= "NormalTextRun SCXW175342908 BCX8"&gt;You'll&lt;/span&gt;&lt;span class= "NormalTextRun SCXW175342908 BCX8"&gt; Learn in This Episode&lt;/span&gt;&lt;/span&gt;&lt;/strong&gt;&lt;span class= "EOP Selected SCXW175342908 BCX8" data-ccp-props= "{}"&gt; &lt;/span&gt;&lt;/p&gt; &lt;/div&gt; &lt;div class="OutlineElement Ltr SCXW175342908 BCX8"&gt; &lt;p class="Paragraph SCXW175342908 BCX8"&gt;&lt;span class= "NormalTextRun SCXW175342908 BCX8"&gt;• How Jason went from unemployment during the recession to Rookie of the Year&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW175342908 BCX8"&gt;&lt;span class= "SCXW175342908 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW175342908 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW175342908 BCX8"&gt;• The exact strategy he uses to win bidding wars in competitive markets&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW175342908 BCX8"&gt;&lt;span class= "SCXW175342908 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW175342908 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW175342908 BCX8"&gt;• Why relationships and communication win more deals than price alone&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW175342908 BCX8"&gt;&lt;span class= "SCXW175342908 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW175342908 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW175342908 BCX8"&gt;• How adversity shaped his discipline and relentless drive&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW175342908 BCX8"&gt;&lt;span class= "SCXW175342908 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW175342908 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW175342908 BCX8"&gt;• The mindset behind balancing success, family, and long term wealth&lt;/span&gt;&lt;span class= "EOP Selected SCXW175342908 BCX8" data-ccp-props= "{}"&gt; &lt;/span&gt;&lt;/p&gt; &lt;p class="Paragraph SCXW175342908 BCX8"&gt; &lt;/p&gt; &lt;div class="OutlineElement Ltr SCXW221575087 BCX8"&gt; &lt;p class="Paragraph SCXW221575087 BCX8"&gt;&lt;strong&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt;Key Takeaways (Timestamps)&lt;/span&gt;&lt;/strong&gt;&lt;span class= "EOP Selected SCXW221575087 BCX8" data-ccp-props= "{}"&gt; &lt;/span&gt;&lt;/p&gt; &lt;/div&gt; &lt;div class="OutlineElement Ltr SCXW221575087 BCX8"&gt; &lt;p class="Paragraph SCXW221575087 BCX8"&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt;0:00&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt; Introduction to Jason Orsini&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW221575087 BCX8"&gt;&lt;span class= "SCXW221575087 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW221575087 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt;1:00&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt; Losing his teaching job during the recession&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW221575087 BCX8"&gt;&lt;span class= "SCXW221575087 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW221575087 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt;2:00&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt; Setting the goal to sell 20 homes in year one&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW221575087 BCX8"&gt;&lt;span class= "SCXW221575087 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW221575087 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt;4:00&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt; Winning Rookie of the Year&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW221575087 BCX8"&gt;&lt;span class= "SCXW221575087 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW221575087 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt;5:00&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt; Living in his car and overcoming adversity&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW221575087 BCX8"&gt;&lt;span class= "SCXW221575087 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW221575087 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt;7:30&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt; Proving success to his father&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW221575087 BCX8"&gt;&lt;span class= "SCXW221575087 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW221575087 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt;9:00&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt; Massive vision and long term goals&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW221575087 BCX8"&gt;&lt;span class= "SCXW221575087 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW221575087 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt;10:00&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt; Parenting and building generational wealth&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW221575087 BCX8"&gt;&lt;span class= "SCXW221575087 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW221575087 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt;17:00&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt; How to win bidding wars in competitive markets&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW221575087 BCX8"&gt;&lt;span class= "SCXW221575087 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW221575087 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt;20:00&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt; The strategy of humanizing buyers in offers&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW221575087 BCX8"&gt;&lt;span class= "SCXW221575087 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW221575087 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt;23:00&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt; Why terms matter as much as price&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW221575087 BCX8"&gt;&lt;span class= "SCXW221575087 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW221575087 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt;26:00&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt; Why relationships between agents win deals&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW221575087 BCX8"&gt;&lt;span class= "SCXW221575087 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW221575087 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt;28:00&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt; Why "highest and best" is the lazy negotiation tactic&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW221575087 BCX8"&gt;&lt;span class= "SCXW221575087 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW221575087 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt;31:00&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt; Jason's 3:30 AM daily routine and competitive mindset&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW221575087 BCX8"&gt;&lt;span class= "SCXW221575087 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW221575087 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt;33:00&lt;/span&gt;&lt;span class= "NormalTextRun SCXW221575087 BCX8"&gt; Balancing success, business, and family&lt;/span&gt;&lt;span class="EOP SCXW221575087 BCX8" data-ccp-props="{}"&gt; &lt;/span&gt;&lt;/p&gt; &lt;p class="Paragraph SCXW221575087 BCX8"&gt; &lt;/p&gt; &lt;/div&gt; &lt;div class="OutlineElement Ltr SCXW237316465 BCX8"&gt; &lt;p class="Paragraph SCXW237316465 BCX8"&gt;&lt;strong&gt;&lt;span class= "TextRun SCXW237316465 BCX8" lang="EN-US" xml:lang="EN-US" data-contrast="auto"&gt;&lt;span class= "NormalTextRun SCXW237316465 BCX8"&gt;Let's&lt;/span&gt;&lt;span class= "NormalTextRun SCXW237316465 BCX8"&gt; Connect&lt;/span&gt;&lt;/span&gt;&lt;span class="EOP Selected SCXW237316465 BCX8" data-ccp-props="{}"&gt; &lt;/span&gt;&lt;/strong&gt;&lt;/p&gt; &lt;/div&gt; &lt;div class="OutlineElement Ltr SCXW237316465 BCX8"&gt; &lt;p class="Paragraph SCXW237316465 BCX8"&gt;&lt;span class= "NormalTextRun SCXW237316465 BCX8"&gt;Host&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW237316465 BCX8"&gt;&lt;span class= "SCXW237316465 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW237316465 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW237316465 BCX8"&gt;Ben Lavender&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW237316465 BCX8"&gt;&lt;span class= "SCXW237316465 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW237316465 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW237316465 BCX8"&gt;Instagram: https://www.instagram.com/blavmtg&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW237316465 BCX8"&gt;&lt;span class= "SCXW237316465 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW237316465 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW237316465 BCX8"&gt;@blavmtg&lt;/span&gt;&lt;span class= "EOP Selected SCXW237316465 BCX8" data-ccp-props= "{}"&gt; &lt;/span&gt;&lt;/p&gt; &lt;/div&gt; &lt;div class="OutlineElement Ltr SCXW237316465 BCX8"&gt; &lt;p class="Paragraph SCXW237316465 BCX8"&gt;&lt;span class= "NormalTextRun SCXW237316465 BCX8"&gt;Guest&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW237316465 BCX8"&gt;&lt;span class= "SCXW237316465 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW237316465 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW237316465 BCX8"&gt;Jason Orsini&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW237316465 BCX8"&gt;&lt;span class= "SCXW237316465 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW237316465 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW237316465 BCX8"&gt;Instagram: https://www.instagram.com/jason_orsini&lt;/span&gt;&lt;span class= "LineBreakBlob BlobObject DragDrop SCXW237316465 BCX8"&gt;&lt;span class= "SCXW237316465 BCX8"&gt; &lt;/span&gt;&lt;br class= "SCXW237316465 BCX8" /&gt;&lt;/span&gt;&lt;span class= "NormalTextRun SCXW237316465 BCX8"&gt;@jason_orsini&lt;/span&gt;&lt;span class= "EOP Selected SCXW237316465 BCX8" data-ccp-props= "{}"&gt; &lt;/span&gt;&lt;/p&gt; &lt;p class="Paragraph SCXW237316465 BCX8"&gt;&lt;span class= "EOP Selected SCXW237316465 BCX8" data-ccp-props="{}"&gt;Madison Mortgage NMLS #1862796&lt;/span&gt;&lt;/p&gt; &lt;p class="Paragraph SCXW237316465 BCX8"&gt;&lt;span class= "EOP Selected SCXW237316465 BCX8" data-ccp-props= "{}"&gt;Instagram:&lt;/span&gt; &lt;span class= "EOP Selected SCXW237316465 BCX8" data-ccp-props= "{}"&gt;@madison_mortgage&lt;/span&gt;&lt;/p&gt; &lt;/div&gt; &lt;div class="OutlineElement Ltr SCXW237316465 BCX8"&gt; &lt;p class="Paragraph SCXW237316465 BCX8"&gt;&lt;span class= "EOP SCXW237316465 BCX8" data-ccp-props="{}"&gt; &lt;/span&gt;&lt;/p&gt; &lt;/div&gt; &lt;/div&gt;</description>

The Madison Podcast

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

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

Description