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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

31:27

He Set a Goal of 40 Units. He Ended Up with 2,700 w/...

Real Estate Investing with RealDealChat ·

2026/04/20

Jens Nielsen left a 25-year IT career and went from 40-unit goal to managing 2,700 units — here's the exact path he took to scale commercial real estate.In this episode of RealDealChat, Jack Hoss sits down with Jens Nielsen — a former IT professional turned commercial real estate investor and high-performance coach — to break down how he went from a linear 10-year plan to managing over 2,700 units across multifamily, industrial, and flex space.Jens covers:How he started with a fourplex for $115K and

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34:46

Why the Next 3–5 Years Are the Best Ever for Notes w/...

Real Estate Investing with RealDealChat ·

2026/04/18

Eddie Speed has closed 50,000+ note deals in 45 years — and says the next 3–5 years may be the best window for note investing he's ever seen.In this episode of RealDealChat, Jack Hoss sits down with Eddie Speed, founder of NoteSchool, for a conversation 45 years in the making. Eddie has closed over 50,000 note deals, trained thousands of investors, and watched the real estate market cycle through every imaginable condition — and he's more fired up about notes right now than at any point in his

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32:03

You Don't Own Your Brand (Until You Do This) w/ Joey...

Real Estate Investing with RealDealChat ·

2026/04/16

Joey Vitale reveals why most entrepreneurs don't legally own their brand — and the trademark strategy that protects everything you're building.In this episode of RealDealChat, Jack Hoss sits down with Joey Vitale, founder of Indie Law and Skybreaker, to break down two things most entrepreneurs ignore until it's too late: trademark protection and offshore staffing systems.Joey shares the frameworks that helped him scale a seven-figure trademark law firm, step away from daily operations, and launch a

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30:07

Why Your Investment Property Is Probably Underinsured...

Real Estate Investing with RealDealChat ·

2026/04/14

Michael Silverman reveals why most investment properties are underinsured — and the liability gaps that could cost investors everything.In this episode of RealDealChat, Jack Hoss sits down with Michael Silverman of Silver Lining Insurance Agency (slia.agency) — third-generation insurance broker with nearly 40 years of experience — to break down the insurance blind spots most real estate investors don't know they have.Michael covers:Why liability coverage is the #1 most overlooked protection for

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33:37

Turn One House Into 28 Doors with Co-Living w/...

Real Estate Investing with RealDealChat ·

2026/04/12

Katrina Robinson breaks down how co-living turns a single-family home into 28 doors — and how investors can 10X rental income without buying more properties.In this episode of RealDealChat, Jack Hoss sits down with Katrina E. Robinson, founder of Group Home on Autopilot and Round Table Living, to break down the co-living model that's helping real estate investors maximize income on existing properties while solving the affordable housing crisis.Katrina covers:Why renting by the bed vs. by the house

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32:34

He Never Sold a Property. Now He Has 30 Buildings. w/...

Real Estate Investing with RealDealChat ·

2026/04/10

Onyi Odunukwe built 30 commercial properties without selling a single one — and his franchise strategy is what made it all possible.In this episode of RealDealChat, Jack Hoss sits down with Onyi Odunukwe — aka the Sweat Pant Millionaire — CEO of Glow Tanning (a top 500 franchise with 360+ locations) and owner of nearly 30 commercial properties, all acquired in just five years without selling a single one.Onyi breaks down:Why delayed gratification is the real skill behind commercial real estate

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32:41

From 50 to 270 Deals: How Virtual Assistants Did It...

Real Estate Investing with RealDealChat ·

2026/04/08

Bob Lachance went from 50 deals to 270 deals a year using virtual assistants — and built one of the top VA companies in real estate. Here's exactly how.In this episode of RealDealChat, Jack Hoss sits down with Bob Lachance, former pro hockey player turned real estate investor, co-founder of Fortune Builders, and CEO of REVA Global — one of the leading virtual assistant companies serving real estate investors.Bob covers:From ice hockey to real estate: how a $32K first deal turned into a full

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27:59

A Contractor Stole $104K — Here's What Kirk Built...

Real Estate Investing with RealDealChat ·

2026/04/06

Kirk Welsh lost $104K to a contractor, then rebuilt with systems, accountability, and personal development. Here's the framework that changed everything.In this episode of RealDealChat, Jack Hoss sits down with Kirk Welsh — licensed architect, real estate investor, flooring company owner, and personal development coach — to have the conversation most real estate content avoids: the inner game of running a business.Kirk covers:The path from licensed architect to real estate investor to flooring

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40:07

I Got Sick Chasing Deals — Here's What I Changed w/...

Real Estate Investing with RealDealChat ·

2026/04/04

Michael Coxen burned out chasing deals, ended up hospitalized with colitis, and then built his best business by becoming more mindful. Here's how.In this episode of RealDealChat, Jack Hoss sits down with Michael Coxen, Las Vegas real estate broker, investor, and host of The Mindful Agent Podcast, to explore the intersection of mindfulness, health, and business performance — and why intentional living turns out to be a better growth strategy than hustle.Michael covers:How ulcerative colitis

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35:45

How Real Estate Investors Can Pay Less for College w/...

Real Estate Investing with RealDealChat ·

2026/04/02

Brad Baldridge breaks down how real estate investors and business owners can legally reduce college costs — using income control, asset positioning, and tax strategy.In this episode of RealDealChat, Jack Hoss sits down with Brad Baldridge, financial advisor and college planning specialist at Taming the High Cost of College, to unpack one of the most overlooked financial planning opportunities for real estate investors — using their assets and income control to dramatically reduce what they pay for

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29:37

Timberland Investing: Multiple Paydays from One...

Real Estate Investing with RealDealChat ·

2026/03/31

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.John covers:Why his family bought timberland in 2008 — and how 15 years at JP Morgan and Wells Fargo led him

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45:15

How AI Search Is Changing Where Seller Leads Come...

Real Estate Investing with RealDealChat ·

2026/03/29

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 assumption quietly killing investor deal flow — and why optimizing leads beats generating moreWhy "if you're not

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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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704 results

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