The Iced Coffee Hour

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*𝗖𝗢𝗡𝗡𝗘𝗖𝗧 𝗪𝗜𝗧𝗛 𝗨𝗦*

𝗜𝗚: https://www.instagram.com/icedcoffeehour
𝗝𝗔𝗖𝗞: https://www.instagram.com/jlsselby
𝗚𝗥𝗔𝗛𝗔𝗠: https://www.instagram.com/gpstephan

𝗖𝗹𝗶𝗽𝘀 𝗖𝗵𝗮𝗻𝗻𝗲𝗹: https://www.youtube.com/c/TheIcedCoffeeHourClips
𝗫.𝗰𝗼𝗺: https://x.com/TheICHpodcast
𝗧𝗶𝗸𝗧𝗼𝗸: https://www.tiktok.com/@theicedcoffeehour
𝗦𝗽𝗼𝘁𝗶𝗳𝘆: https://open.spotify.com/show/5c2uoXBQkOjIiCOf60jJj7
𝗔𝗽𝗽𝗹𝗲: https://podcasts.apple.com/us/podcast/the-iced-coffee-hour/id1515070058

For sponsorships or business inquiries reach out to: icedcoffeehourpartnerships@gmail.com

Apply for The Index Membership: https://entertheindex.com/

For Podcast Inquiries, please DM @icedcoffeehour on Instagram!

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

*Some of the links and other products that appear on this video are from companies which Graham Stephan & Jack Selby will earn an affiliate commission or referral bonus. Graham Stephan & Jack Selby are part of an affiliate network and receives compensation for sending traffic to partner sites. The content in this video is accurate as of the posting date. Some of the offers mentioned may no longer be available.
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*𝗖𝗢𝗡𝗡𝗘𝗖𝗧 𝗪𝗜𝗧𝗛 𝗨𝗦*

𝗜𝗚: https://www.instagram.com/icedcoffeehour
𝗝𝗔𝗖𝗞: https://www.instagram.com/jlsselby
𝗚𝗥𝗔𝗛𝗔𝗠: https://www.instagram.com/gpstephan

𝗖𝗹𝗶𝗽𝘀 𝗖𝗵𝗮𝗻𝗻𝗲𝗹: https://www.youtube.com/c/TheIcedCoffeeHourClips
𝗫.𝗰𝗼𝗺: https://x.com/TheICHpodcast
𝗧𝗶𝗸𝗧𝗼𝗸: https://www.tiktok.com/@theicedcoffeehour
𝗦𝗽𝗼𝘁𝗶𝗳𝘆: https://open.spotify.com/show/5c2uoXBQkOjIiCOf60jJj7
𝗔𝗽𝗽𝗹𝗲: https://podcasts.apple.com/us/podcast/the-iced-coffee-hour/id1515070058

For sponsorships or business inquiries reach out to: icedcoffeehourpartnerships@gmail.com

Apply for The Index Membership: https://entertheindex.com/

For Podcast Inquiries, please DM @icedcoffeehour on Instagram!

Timestamps:

00:00:00 - Intro
00:01:02 - The Wild Stats: Half of Americans Can't Cover $1,000
00:04:35 - Is the American Dream Dead? Why Young People Are Giving Up
00:06:27 - The Real Reason People Feel Held Back From Wealth
00:08:51 - The $4 Cab Ride & How Tips Get Manipulated
00:13:41 - Will People Be Worse Off in 2030?
00:14:38 - Sponsor: OpusClip
00:15:42 - At What Income Is Paycheck-to-Paycheck a Spending Problem?
00:23:04 - The #1 Wealth Killer (It's Not What You Think)
00:24:58 - "You Guys Are Cheap, Not Frugal": The Big Debate Begins
00:29:13 - The Norway Flight: Is Spending $4,400 on a Seat Worth It?
00:31:16 - Sponsors: Straight Arrow News & AMP
00:33:52 - Money for the Sake of Money Is a Trap
00:38:55 - Behavior vs. Math: How Childhood Shaped Their Money Habits
00:44:29 - The Guilt-Free Spending Formula
00:46:29 - How To Actually Track & Save Money
00:48:43 - Why Humphrey Still Feels Like He's Failing
00:49:30 - Do They Feel Wealthy? (The Answer Is Always Double)
00:51:47 - The Case for Paying in Cash
00:54:08 - One Idea To Walk Away With: The 20% Test
00:55:17 - Looking Poor in San Francisco & Graham's Underwear Scandal
00:59:03 - Cars That Make You Look Rich for Cheap
01:01:02 - How To Actually Get Rich in 2026
01:01:20 - Sponsors: Incogni & FanDuel
01:03:41 - Content Creation, AI Consulting & The Side Hustle Debate
01:06:57 - Which Side Hustles Aren't Worth It
01:07:51 - Why People Go Broke for Their Cars
01:11:20 - Buy vs. Lease & The Tesla Math
01:14:10 - The Best Car To Buy in Every Income Bracket
01:15:24 - Graham's Tesla Regrets & Lowball Offer Game
01:19:29 - Selling the Famous Graham Stephan Model 3
01:21:12 - The Tiers of Wealth: $100K, $500K, $5M and Beyond
01:25:49 - What Aspirations Are Left at Their Net Worth?
01:28:35 - Opportunity Cost of Time: Why They Can't Just Relax
01:32:03 - The Perfect Portfolio & Individual Stocks vs. Index Funds
01:33:38 - Should Taxes Drive Your Investment Decisions?
01:36:13 - Best Investments To Get Rich & Buying at All-Time Highs
01:38:35 - The Worst Investment Advice Online
01:39:55 - Two Stocks for the Next 10 Years
01:42:22 - The S&P 1 Strategy Debate
01:44:43 - Humphrey's Bitcoin Story: The $60 Coffee
01:47:33 - What Money Means & The Best Things To Spend On
01:49:59 - The $100 Coin Flip
01:51:38 - Rapid Fire Questions
01:54:23 - Wrap-Up & Post-Show

*Some of the links and other products that appear on this video are from companies which Graham Stephan & Jack Selby will earn an affiliate commission or referral bonus. Graham Stephan & Jack Selby are part of an affiliate network and receives compensation for sending traffic to partner sites. The content in this video is accurate as of the posting date. Some of the offers mentioned may no longer be available.
Learn more about your ad choices. Visit podcastchoices.com/adchoices

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*𝗖𝗢𝗡𝗡𝗘𝗖𝗧 𝗪𝗜𝗧𝗛 𝗨𝗦*

𝗜𝗚: https://www.instagram.com/icedcoffeehour
𝗝𝗔𝗖𝗞: https://www.instagram.com/jlsselby
𝗚𝗥𝗔𝗛𝗔𝗠: https://www.instagram.com/gpstephan

𝗖𝗹𝗶𝗽𝘀 𝗖𝗵𝗮𝗻𝗻𝗲𝗹: https://www.youtube.com/c/TheIcedCoffeeHourClips
𝗫.𝗰𝗼𝗺: https://x.com/TheICHpodcast
𝗧𝗶𝗸𝗧𝗼𝗸: https://www.tiktok.com/@theicedcoffeehour
𝗦𝗽𝗼𝘁𝗶𝗳𝘆: https://open.spotify.com/show/5c2uoXBQkOjIiCOf60jJj7
𝗔𝗽𝗽𝗹𝗲: https://podcasts.apple.com/us/podcast/the-iced-coffee-hour/id1515070058

00:00:00 - Intro
00:00:57 - $500M Real Estate, $400M Debt & Why Creative Finance Works
00:04:48 - Walking Through a Sub-2 Deal & Is This Even Legal?
00:09:01 - How Mortgages Really Work & Why Banks Don't Care
00:13:35 - Non-Recourse Debt, Infinite ROI & Biggest Losses
00:16:42 - Sponsor: Ethos
00:18:02 - Multiple Strategies, Creative Finance Defined & Building the Operation
00:23:23 - Why Smart Sellers Should Never Sell for Cash
00:25:54 - Graham's LA Property: The Lease Option Math
00:28:35 - The Afterparty Strategy, Homeless Lady Deal & Where He Buys
00:31:14 - Sponsor: Hims
00:32:33 - Sponsor: ZipRecruiter
00:33:29 - Execution, creativelisting.com & The Gator Program
00:36:00 - Best Deal Ever & Buying Graham's Primary Residence
00:38:01 - 10-Year Predictions & The Affordability Crisis
00:41:35 - The Shrinking Middle Class & Jason Oppenheim
00:43:52 - Five Trends: Co-Living, Oxford House, PadMission
00:46:42 - How the House Determines the Strategy & PadSplit
00:51:26 - Where He Won't Buy: California & Blue States
00:54:04 - Fixing Housing & Middle Class Survival Strategies
00:56:31 - The RV Park Buy Box & Why Brokers Don't Get Creative Finance
00:58:00 - Sponsor: Shopify
00:59:40 - Logic Over Sales Tactics: Accidental Landlords & workamper.com
01:02:00 - Car Washes & Why RV Parks Are Most Profitable
01:05:19 - Oil Field Parks & Why BRRRR Is Dangerous
01:08:09 - Multifamily Bloodbath & Ken McElroy
01:09:35 - The Great Rent vs Buy Debate
01:17:32 - Lending Money: Double Closes & Gap Lending
01:22:34 - Worst Deal Ever & Why Private Jets Are Irresponsible
01:26:12 - Tiers of Wealth: $1M to $100M+
01:28:53 - Family Offices & Asset Protection
01:31:58 - What He Spends Money On & Creative Finance on Trucks
01:36:00 - Real Estate Agents vs Brokers & Income Tiers
01:39:19 - The Dangers of Creative Finance & Rapid Fire
01:43:45 - Final Advice & Wrap-Up

For sponsorships or business inquiries reach out to: icedcoffeehourpartnerships@gmail.com

Apply for The Index Membership: https://entertheindex.com/

For Podcast Inquiries, please DM @icedcoffeehour on Instagram!

*Some of the links and other products that appear on this video are from companies which Graham Stephan & Jack Selby will earn an affiliate commission or referral bonus. Graham Stephan & Jack Selby are part of an affiliate network and receives compensation for sending traffic to partner sites. The content in this video is accurate as of the posting date. Some of the offers mentioned may no longer be available.
Learn more about your ad choices. Visit podcastchoices.com/adchoices

Claude: Get started with Claude today at https://claude.ai/icedcoffeeAirbnb: Find a co-host at https://airbnb.com/hostUpwork: Post your job free at http://upwork.com and connect with top talent to grow your business.ZocDoc: Check out Zocdoc and stop putting off those doctors appointments. Go to https://zocdoc.com/ICED to find and instantly book a top-rated doctor today.

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*𝗖𝗢𝗡𝗡𝗘𝗖𝗧 𝗪𝗜𝗧𝗛 𝗨𝗦*

𝗜𝗚: https://www.instagram.com/icedcoffeehour
𝗝𝗔𝗖𝗞: https://www.instagram.com/jlsselby
𝗚𝗥𝗔𝗛𝗔𝗠: https://www.instagram.com/gpstephan

𝗖𝗹𝗶𝗽𝘀 𝗖𝗵𝗮𝗻𝗻𝗲𝗹: https://www.youtube.com/c/TheIcedCoffeeHourClips
𝗫.𝗰𝗼𝗺: https://x.com/TheICHpodcast
𝗧𝗶𝗸𝗧𝗼𝗸: https://www.tiktok.com/@theicedcoffeehour
𝗦𝗽𝗼𝘁𝗶𝗳𝘆: https://open.spotify.com/show/5c2uoXBQkOjIiCOf60jJj7
𝗔𝗽𝗽𝗹𝗲: https://podcasts.apple.com/us/podcast/the-iced-coffee-hour/id1515070058

For sponsorships or business inquiries reach out to: icedcoffeehourpartnerships@gmail.com

Apply for The Index Membership: https://entertheindex.com/

For Podcast Inquiries, please DM @icedcoffeehour on Instagram!

*Some of the links and other products that appear on this video are from companies which Graham Stephan & Jack Selby will earn an affiliate commission or referral bonus. Graham Stephan & Jack Selby are part of an affiliate network and receives compensation for sending traffic to partner sites. The content in this video is accurate as of the posting date. Some of the offers mentioned may no longer be available.
Learn more about your ad choices. Visit podcastchoices.com/adchoices

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*𝗖𝗢𝗡𝗡𝗘𝗖𝗧 𝗪𝗜𝗧𝗛 𝗨𝗦*

Follow Gary King Pokemon: https://www.instagram.com/realkingpokemon/?hl=en

𝗜𝗚: https://www.instagram.com/icedcoffeehour
𝗝𝗔𝗖𝗞: https://www.instagram.com/jlsselby
𝗚𝗥𝗔𝗛𝗔𝗠: https://www.instagram.com/gpstephan

𝗖𝗹𝗶𝗽𝘀 𝗖𝗵𝗮𝗻𝗻𝗲𝗹: https://www.youtube.com/c/TheIcedCoffeeHourClips
𝗫.𝗰𝗼𝗺: https://x.com/TheICHpodcast
𝗧𝗶𝗸𝗧𝗼𝗸: https://www.tiktok.com/@theicedcoffeehour
𝗦𝗽𝗼𝘁𝗶𝗳𝘆: https://open.spotify.com/show/5c2uoXBQkOjIiCOf60jJj7
𝗔𝗽𝗽𝗹𝗲: https://podcasts.apple.com/us/podcast/the-iced-coffee-hour/id1515070058

For sponsorships or business inquiries reach out to: icedcoffeehourpartnerships@gmail.com

Apply for The Index Membership: https://entertheindex.com/

For Podcast Inquiries, please DM @icedcoffeehour on Instagram!

Timestamps:
00:00:00 - Intro
00:01:10 - Collection Value & Selling Logan Paul a Charizard for $150K
00:05:06 - A Lifetime of Collecting: From Bottle Caps to Charizards
00:10:25 - Grading Charizards in the Early Days & The Shadowless Story
00:12:36 - Old Predictions That Came True & What's Performed Best Since
00:15:14 - Netsuite Sponsor / Best-Performing Cards & The Rise of Gengar
00:19:02 - Pawn Stars Famous Episode & The Charizard Collection's Value Today
00:21:03 - The 17% Sale, Biggest Offers & Why Pokemon Is Booming Again
00:23:34 - When Gary Knew Pokemon Was Safe & How He Built the Collection
00:26:10 - The $16M Illustrator Card & The One-of-One Premium Debate
00:30:14 - Logan Paul's Charizard Crack & His Real Character
00:33:55 - Airbnb & Gusto Sponsor / Gary's No-Cursing Rule & Defending Logan
00:39:46 - Is the Hobby Becoming Too Much of a Business?
00:40:55 - What Cards Should the Average Person Buy?
00:44:47 - Biggest Mistakes, Lies in Pokemon Investing & Keeping a Collection Safe
00:53:58 - The Stolen Cards Story & Getting Them Back
00:59:01 - When to Buy & Hype vs Longevity
00:59:47 - Shopify Sponsor / Beanie Babies, Pokemon's Future & Should You Wait to Buy?
01:04:56 - Grading Wars: PSA vs CGC vs TAG (And Why Gary Won't Use PSA)
01:11:28 - Regrading, Card Repair & The Logan Paul BGS 10 Saga
01:19:24 - Do Celebrity Cards Grade Higher? The Honesty Question
01:23:02 - The Dark Side of the Hobby & The Arita Signature Controversy
01:27:45 - Signatures, Card Authentication & The Kabuto King Strategy
01:32:00 - The Controversial Box-Opening Video Explained
01:36:32 - Why Gary Is Still the #1 Collector & Won't Sell
01:40:05 - Where the Hobby Is Heading & Reviewing Jack's Gyarados
01:46:30 - Restoration Services & Rapid Fire Questions
01:48:42 - Gary's Charity Work & The Chris Camillo Box Story
01:55:51 - Wrap-Up

*Some of the links and other products that appear on this video are from companies which Graham Stephan & Jack Selby will earn an affiliate commission or referral bonus. Graham Stephan & Jack Selby are part of an affiliate network and receives compensation for sending traffic to partner sites. The content in this video is accurate as of the posting date. Some of the offers mentioned may no longer be available.
Learn more about your ad choices. Visit podcastchoices.com/adchoices