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00:00:00 - Intro
00:01:08 - The $1.1 Billion Insight: Buying Dying Retailers for Their Real Estate
00:02:54 - Developer vs. Investor: A Different Way To Think About Real Estate
00:04:19 - The No-Money-Down Playbook: Creating Value Before You Close
00:06:29 - "Get Out of Your Room": Why Hustle Beats Google Maps
00:07:33 - Where To Meet the People Who Make These Deals Happen
00:08:48 - Is This Only for Veterans & Insiders? The "Average Person" Debate
00:10:38 - Real Estate Inefficiency & the Long Island House That Was Underpriced
00:12:54 - The Buy Box: Becoming an Expert in One Neighborhood
00:15:49 - The Great Wealth Transfer: Aging Owners & Off-Market Jewels
00:16:50 - Is Getting Wealthy Just an Effort Problem?
00:17:43 - How He Pitches Sellers & Structures Refundable Deposits
00:18:00 - Sponsor: OpusClip
00:19:15 - Start Small: Is This Harder To Do in 2026?
00:23:53 - The Billion-Dollar German Department Store Flip
00:25:58 - Buying Lord & Taylor With Almost No Money
00:28:48 - The Whiteboard Trick: Splitting OpCo and PropCo
00:32:41 - Sponsors: Gusto & Upwork
00:35:17 - Explaining Hudson's Bay & the $500M Bet From Abu Dhabi
00:40:31 - The Zellers Bidding War: Playing Walmart Against Target
00:46:22 - How Much Did He Actually Make? & the Net Worth Mystery
00:47:42 - Conviction & the "Reality Distortion Field"
00:49:11 - What He Owns Now & Smart Debt vs. Dumb Debt
00:50:51 - Where the Economy Is Headed & Debating Jeremy Grantham
00:53:37 - The University Housing Play & Betting on Top Schools
00:54:23 - Politics, Mamdani & Whether the Rich Give Back Enough
00:57:09 - Is the Housing Crisis a Money Problem or a Spending Problem?
01:02:09 - Diversification vs. Concentration
01:04:15 - The $200M Loss on Guilt & Failing Small
01:05:06 - Sponsors: Shopify & FanDuel
01:07:35 - The Largest Amount He's Ever Lost
01:09:28 - Massive Net Worth Swings & Keeping Life in Perspective
01:11:51 - Nature or Nurture? Office Hours & the Nepotism Charge
01:14:56 - Knowledge vs. Access & Talking to Claude Two Hours a Day
01:15:45 - Negotiation Secrets: Overpaying, Overselling & Knowing the Other Side
01:18:41 - Stalking Deals for Years & Why It Can't Be a Commodity Asset
01:21:37 - The Biggest Mistake the Average Person Is Making
01:23:31 - Individual Choices vs. the Economy & Raising Driven Kids
01:25:04 - The Exact Steps To Become a Real Estate Entrepreneur
01:25:58 - Why He Closes 99.9% of His Deals
01:28:24 - The Cornell Baker House Project
01:31:10 - The Ego Trap: Why Successful People Stop Taking Risks
01:32:10 - What To Optimize For Next & Where His Drive Comes From
01:33:26 - Tiers of Wealth: Private Jets, Economy Flights & Spending on Value
01:36:21 - The Cessna Story: Using Bigger Planes To Motivate Bigger Deals
01:39:47 - What Money Means & The Best Things To Spend On
01:41:16 - The Science of Spending for Happiness (Quiet Homes & Short Commutes)
01:42:47 - The Coming Entrepreneur Revolution & Opportunities for Women
01:46:06 - His Grandmother's 1921 Immigrant Real Estate Story
01:47:48 - The Harshest Truth About Money
01:49:03 - The Power of Yes: Marriage Advice After 30 Years
01:53:19 - Gratitude Rituals & Is There Such a Thing as Too Much Money?
01:54:42 - When He Felt Richest (And Why It Was Depressing)
01:56:16 - Wrap-Up
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