Real Estate Investing with RealDealChat

John Bernard of Southview Timber breaks down timberland investing — how it generates multiple income streams, why the Southeast is the top market, and how to get in. In this episode of RealDealChat, Jack Hoss sits down with John Bernard , co-founder of Southview Timber and manager of the Southview Timberland Fund, to break down one of the most overlooked asset classes in real estate investing. Joh...

Trevor Mauch of Carrot.com breaks down why more leads isn't the answer, why sellers ghost you, and how AI search is already changing deal flow. In this episode of RealDealChat, Jack Hoss sits down with Trevor Mauch , founder and CEO of Carrot.com , to zoom out from marketing tactics and talk about where real estate investing, AI, and online trust are actually heading. Trevor covers: The #1 assumpt...

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 Description In 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 b...

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 succ...

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: T...

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...

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...

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...

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, an...

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...

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-...

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...

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...

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 al...

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 Wh...

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 w...

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...

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-co...

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, w...

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...

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. Fern...

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 dup...

Nicholas Lawless shares why mindset, leadership, and time discipline matter more than tactics for entrepreneurs and real estate investors. In this episode of RealDealChat , Nicholas Lawless joins Jack for a deep, wide-ranging conversation on mindset, leadership, security, and entrepreneurship —and why most success (or failure) starts long before tactics or money enter the picture. Nick shares his...

Ryan Cadwell shares why patience, cash, and realistic underwriting matter more than optimism as real estate heads toward its next reset. In this episode of RealDealChat , Ryan Cadwell, a Partner at Resolute RDM, delivers a grounded, operator-level perspective on where real estate really stands heading into 2026. Ryan walks through his 18-year journey—from growing up around apartments and property...

Marcy Sagel explains how disciplined design decisions directly impact budget control, lease-up speed, and long-term returns in multifamily real estate. In this episode of RealDealChat , Marcy Sagel—principal of MSA Interiors —breaks down how interior design quietly determines whether a multifamily project stays on budget or spirals out of control. With nearly 30 years of experience across market-r...