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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

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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46:31

Why Weak Leadership Is the Real Risk to Entrepreneurs...

Real Estate Investing with RealDealChat ·

2026/02/15

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 unconventional journey from construction and the military to national security work at the highest levels of

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36:25

Why Patience Beats Optimism in Real Estate with Ryan...

Real Estate Investing with RealDealChat ·

2026/02/13

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, CPM of Resolute Realty, 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 management to building a vertically integrated business that includes development, construction, brokerage,

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32:54

Why Design Mistakes Kill ROI in Multifamily with...

Real Estate Investing with RealDealChat ·

2026/02/11

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-rate, student housing, senior housing, and affordable housing, Marcy explains why doing all the design work

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29:24

The Hidden Risk in Construction Projects (And How to...

Real Estate Investing with RealDealChat ·

2026/02/09

Attorney and surety expert Gary Eastman explains how bonds protect real estate investors from delays, contractor failures, and costly litigation.In this episode of RealDealChat, Gary Eastman—attorney and founder of Swift Bonds—breaks down what surety bonds really are, why they exist, and when real estate investors should actually use them.Gary shares how he accidentally built a nationwide surety business after noticing a gap in how probate, construction, and licensing bonds were being handled. We

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36:59

Why Partnerships Make or Break Real Estate Investing...

Real Estate Investing with RealDealChat ·

2026/02/07

Erik Nordstrom and Eric Strom share how surviving the 2008 crash shaped their approach to partnerships, underwriting, and in-house property management.In this episode of RealDealChat, Erik Nordstrom and Eric Strom of Iron Ridge Capital break down what nearly two decades of investing together has taught them about real estate, relationships, and risk.We start with Erik’s early exposure to apartment syndication and the decision to bet on commercial real estate just before the Great Financial Crisis

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34:46

Building Wealth While Building Communities with Dave...

Real Estate Investing with RealDealChat ·

2026/02/05

Dave Holman shares how buy-and-hold real estate, strong operations, and impact-driven housing can create durable wealth and thriving communities.In this episode of RealDealChat, Dave Holman—real estate investor, broker, and property manager—walks through a grounded, real-world approach to building wealth through long-term ownership and responsible operations.Dave shares how a nontraditional path—from nonprofits and entrepreneurship abroad to real estate in Maine—shaped his philosophy around housing,

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39:46

Why Grit Beats Talent in Multifamily Real Estate with...

Real Estate Investing with RealDealChat ·

2026/02/03

Mark Shuler explains why real estate success isn’t about intellect or experience—it’s about grit, systems, and relentless execution.In this episode of RealDealChat, Mark Shuler—architect turned multifamily syndicator—breaks down what it really takes to scale in commercial real estate.With over $600M in assets, 5,000+ doors, and 200+ employees, Mark shares how he transitioned from being a hired architect to a general partner in large value-add syndications. We dive into deep C-class renovations,

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705 results

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