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PODCAST

Real Estate Investing with RealDealChat

RealDealCrew / Jack Hoss

Real Estate Investing with RealDealChat is a podcast featuring interviews with experienced real estate investors, wholesalers, flippers, landlords, and operators actively closing deals. Each episode breaks down: • Real estate investing strategies • Deal sourcing and wholesaling tactics • Fix and flip systems • Rental property scaling • AI and automation tools for investors • Deal operations and lead management Hosted by Jack Hoss, a real estate investor and founder of RealDealCrew, the show

business investing

All Episodes

47:07

The Founder Trap: Why Hard Work Is Keeping You Broke...

Real Estate Investing with RealDealChat ·

2026/03/27

Charles Gaudet took a business from $950K to $66M in 7 years — and says hard work was the problem, not the solution. Here's the system he built.Full DescriptionIn this episode of RealDealChat, Jack Hoss sits down with Charles Gaudet, founder of Predictable Profits and coach to over 2,000 businesses, to break down why most entrepreneurs hit a wall at $1–3M — and the three-system framework that breaks through it.Charles covers:The Founder Trap: why success itself becomes the ceiling, and why doubling

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36:44

Why 90% of FSBOs Fail (And How to Be the 10%) w/ Tim...

Real Estate Investing with RealDealChat ·

2026/03/25

Tim Street reverse-engineered the entire FSBO process into a 7-day blueprint — and his sellers get 102% of list price while saving $30K or more.In this episode of RealDealChat, Jack Hoss sits down with Tim Street, Marine-turned-real estate agent-turned-FSBO educator, to break down one of the most misunderstood niches in real estate.Tim covers:Why 90%+ of FSBOs fail — and why the ones that succeed still sell for 11% less than agent-listed homesThe 3-phase system: Prep & Protect, Price &

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41:32

The Title Insurance Mistakes That Cost Investors...

Real Estate Investing with RealDealChat ·

2026/03/23

Dru Wischhover breaks down what title insurance actually covers, the fraud patterns targeting investors, and what kills deals at the closing table.In this episode of RealDealChat, Jack Hoss sits down with Dru Wischhover, owner of a boutique title company and development firm, to pull back the curtain on one of the most misunderstood parts of real estate investing — title insurance.Dru covers:The difference between an owner's policy and a lender's policy — and why investors often skip the wrong

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36:40

$50K at 0% Interest: The Credit Strategy Investors...

Real Estate Investing with RealDealChat ·

2026/03/21

Daniel McDavid breaks down how to repair your credit in 4–6 months, access up to $50K at 0% interest, and fund your first real estate deal.In this episode of RealDealChat, Jack Hoss sits down with Daniel McDavid, founder of Move Mountains Funding, to break down one of the most overlooked levers in real estate — credit repair and business funding.Daniel shares the full journey:How a prayer, an Instagram post, and a $10,000 bet launched his entire businessThe 4–6 month credit repair timeline (and when

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36:11

From Fired to $22M in Land Development with Brandon Cobb

Real Estate Investing with RealDealChat ·

2026/03/19

Brandon Cobb went from getting fired to managing $22M in land development — and breaks down exactly how he did it and what almost wiped him out.In this episode of RealDealChat, Jack Hoss sits down with Brandon Cobb, fund manager and land development coach at Learn Land Development, to unpack one of the most underutilized strategies in real estate investing.Brandon shares the full journey:How getting fired from medical device sales launched his entrepreneurial pathThe three phases of land development

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47:11

How to Invest in Real Estate Without Being a Landlord...

Real Estate Investing with RealDealChat ·

2026/03/17

Lane Kawaoka explains passive real estate investing, syndications, and how high-income earners can build wealth without being landlords.In this episode of RealDealChat, Jack Hoss sits down with Lane Kawaoka from Simple Passive Cashflow to break down how real estate investors can build wealth without managing properties themselves.Lane specializes in helping high-income professionals transition into passive real estate investing through syndications and private placements.In this conversation, we

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43:04

Transforming Real Estate Investing into a Business w/...

Real Estate Investing with RealDealChat ·

2026/03/15

In this conversation, Mark Mullen discusses the importance of treating real estate investing as a serious business. He emphasizes the role of a CFO in managing finances, the need for detailed financial tracking, and the significance of collaboration and communication in real estate projects. Mark shares insights on profit margins in fix and flipping, the value of performance-based CFO services, and the lessons learned from mistakes in business. He concludes with advice on building strong

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34:15

Mastering Passive Investing: Insights from Patrick...

Real Estate Investing with RealDealChat ·

2026/03/13

In this conversation, Patrick Grimes shares his journey from a corporate engineering background to becoming a successful entrepreneur and passive investor. He discusses the importance of time freedom, the transition to passive investing, and the significance of diversification in building a resilient investment portfolio. Patrick also delves into the role of AI in enhancing business processes and the importance of non-correlated investments, particularly in healthcare. The discussion highlights the

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42:12

From Wall Street to Short-Term Rentals: A Journey w/...

Real Estate Investing with RealDealChat ·

2026/03/11

In this conversation, Michael Chang shares his journey from a successful career in investment banking on Wall Street to becoming a thriving entrepreneur in the short-term rental market. He discusses the challenges and lessons learned from his transition, including the importance of flexibility, the impact of technology, and the financial benefits of short-term rentals compared to traditional long-term investments. Michael also delves into the STR tax loophole, market saturation, and the significance

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35:02

The Portugal Golden Visa: A Path to Residency w/...

Real Estate Investing with RealDealChat ·

2026/03/09

In this conversation, Daniel Daly shares his journey from the automotive industry to real estate investment, focusing on international opportunities, particularly in Portugal. He discusses the advantages of the Portugal Golden Visa program, the challenges of building a network abroad, and the importance of customer experience in hospitality. Daniel emphasizes the need for effective delegation and the impact of tourism on property values in Europe. He also addresses the evolving regulations in real

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28:23

Nearshore vs Offshore Talent: What Actually Works w/...

Real Estate Investing with RealDealChat ·

2026/03/07

Brian Sampson breaks down nearshore vs offshore talent, critical thinking vs scripted VAs, and how Latin America teams create true ROI for real estate operators.In this episode of RealDealChat, Jack Hoss sits down with Brian Sampson, co-founder of PLUG, to unpack the real differences between offshore, nearshore, and onshore talent — and why it matters more than ever in the age of AI.If you’re a real estate investor, realtor, or operator using virtual assistants, this conversation will challenge how

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44:34

Why Most Real Estate Investors Plateau with John...

Real Estate Investing with RealDealChat ·

2026/03/05

John Donnelly shares why most real estate investors plateau — and the mindset, systems, and accountability needed to break through.In this episode of RealDealChat, John Donnelly joins Jack to unpack a problem most investors quietly face: growth ceilings.We explore why operators often stall after early wins, how identity and self-concept cap performance, and why systems only work when they’re aligned with personal clarity.John shares insights on:Breaking through revenue plateausWhy mindset >

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33:32

Why 82% of Homeowners Regret Their Purchase with Kim...

Real Estate Investing with RealDealChat ·

2026/03/03

Kim Costa explains why 82% of homeowners regret their purchase — and how aligning your home with your identity changes everything.In this episode of RealDealChat, Kim Costa — author of Live in Your Wheelhouse and host on The American Dream TV — breaks down the psychology behind real estate decisions.Kim introduces her framework built around:The Four M’s (Myself, Mastery, Mission, Mates)The Wheel of Life across 8 key areasWhy most buyers move without clarityThe statistic that 82% of homeowners report

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36:38

How to Increase Airbnb Revenue 23% (Without More...

Real Estate Investing with RealDealChat ·

2026/03/01

Dan Rivers explains how short-term rental owners can increase Airbnb revenue by 20%+ using listing optimization, pricing strategy, and revenue management.In this episode of RealDealChat, Jack Hoss sits down with Dan Rivers, founder of Synergy Stays, to break down what most Airbnb hosts get wrong about revenue management.Dan shares how his clients average a 23% revenue lift in year one, and why many operators are unknowingly leaving thousands on the table.We cover:The biggest Airbnb listing

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34:57

Opportunity Zones Are Permanent: What Investors Need...

Real Estate Investing with RealDealChat ·

2026/02/27

Ashley Tison explains how Opportunity Zones became permanent — and how investors can defer, reduce, and potentially eliminate capital gains taxes.In this episode of RealDealChat, Ashley Tison of OZ Pros breaks down Opportunity Zones in plain English — what they are, how they work, and why the recent legislative updates changed the long-term strategy for investors.We cover:How Opportunity Zones were created under the Tax Cuts and Jobs ActThe “defer, reduce, eliminate” frameworkWhat the new rolling

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44:34

Why 100% Loan-to-Cost Lending Is Working in the...

Real Estate Investing with RealDealChat ·

2026/02/25

Matthew Medrano shares how Dynamo Capital scaled from a $5M goal to a $100M+ private credit fund by focusing on speed, alignment, and Midwest lending.In this episode of RealDealChat, Matthew Medrano of Dynamo Capital breaks down how a frustrated mortgage broker built a direct lending fund focused on fast funding, flexible terms, and aligned incentives.We cover:Why Dynamo offers 100% loan-to-cost on select fix-and-flip projectsHow they structured their fund without the traditional “2 and 20” modelWhy

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31:52

From Wall Street to 500M+ in Apartments: Lessons in...

Real Estate Investing with RealDealChat ·

2026/02/23

Michael Pouliot shares why vertical integration, disciplined buy boxes, and patience are key as multifamily heads into a major refinance cycle.In this episode of RealDealChat, Michael Pouliot—fourth-generation real estate entrepreneur and founder of Carbon—breaks down what’s really happening in multifamily as the 2025–2027 maturity wall approaches.We discuss raising capital ahead of distress, why the downturn took longer than expected, and how today’s opportunities are often coming from exhausted

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40:23

Subject-To Real Estate Done Right with Caleb Christopher

Real Estate Investing with RealDealChat ·

2026/02/21

Caleb Christopher breaks down subject-to real estate, wraparound mortgages, and why creative finance without proper structure can destroy deals.In this episode of RealDealChat, Caleb Christopher — self-described “systems nerd” and real estate deal architect — explains how creative finance deals actually work in the real world.We go deep into subject-to transactions, wraparound mortgages, due-on-sale clauses, VA loan nuances, and why title companies often can’t (and shouldn’t) provide advisory

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41:03

How Self Storage Can Offset 50–90% of Your Tax Bill...

Real Estate Investing with RealDealChat ·

2026/02/19

Fernando Angelucci explains how tax-advantaged self storage, solar infrastructure, and AI-driven pricing are reshaping modern real estate returns.Full description:In this episode of RealDealChat, Fernando Angelucci, founder of Self Storage Syndicated Equities, breaks down why self storage continues to outperform—and how investors can use it to reduce taxes while building long-term wealth.Fernando explains how cost segregation, bonus depreciation, Section 179 (via solar installations), and partial

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46:22

Short-Term Rentals Aren’t Easy Anymore—Here’s What...

Real Estate Investing with RealDealChat ·

2026/02/17

Kenny Bedwell explains why short-term rentals are harder today—and how data, design, and discipline still create outsized returns.In this episode of RealDealChat, Kenny Bedwell—short-term rental investor, former Citibank data analyst, and founder of STR Insights—breaks down what has actually changed in the Airbnb market over the last eight years.Kenny shares his journey from house hacking a duplex in Buffalo to owning short-term rentals across multiple states and even operating a hotel. We dive into

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692 results

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