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PODCAST

RealDealChat / Lessons from Real Estate Investors

RealDealCrew | Jack Hoss

RealDealChat brings you unfiltered conversations with elite real estate investors who share their journey to success. Each episode delivers practical wisdom from industry leaders who openly discuss: • Proven strategies that are generating results in today"s market • Honest reflections on mistakes and missteps they"ve encountered along the way • Actionable takeaways you can implement immediately to elevate your real estate portfolio Whether you"re a seasoned investor or just starting out, our

education how to

All Episodes

39:35

From BRRRRs to 1,000+ Units Managed: Mark Ainley’s...

RealDealChat / Lessons from Real Estate Investors ·

2025/09/27

Mark Ainley shares his journey from BRRRRs to running GC Realty, scaling property management in Chicago, and lessons from 20+ years in real estate.In this episode of RealDealChat, Jack sits down with Mark Ainley, co-founder of GC Realty & Development, co-host of Straight Up Chicago Investor Podcast, and long-time property manager and investor.Mark shares how he transitioned from house hacking and BRRRR deals to running one of Chicago’s largest property management firms. He explains why property

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29:27

Why “Passive Investors” Fail | Shawn Griffith on...

RealDealChat / Lessons from Real Estate Investors ·

2025/09/25

Shawn Griffith of Kraft Capital explains why no investor should ever be passive, how to underwrite risk, and why multifamily is a long-term wealth game.In this episode of RealDealChat, Jack sits down with Shawn Griffith, managing partner at Kraft Capital Investments, to discuss the reality of multifamily investing, the dangers of being a “passive investor,” and why risk management is the cornerstone of long-term success.Shawn shares his journey from his first LP deal that tripled investor money, to

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09:19

RealDealCast: How I Use Google’s Nano Banana AI to...

RealDealChat / Lessons from Real Estate Investors ·

2025/09/25

Discover time-saving AI tools and tech tips for real estate investors in this episode of RealDealCast. From enhancing thumbnails to generating professional headshots, Jack Hoss explores Google’s Nano Banana AI and other automation tools that can save investors valuable time.In this solo session, Jack shares real-world use cases—improving podcast thumbnails, designing hero banners, cleaning up headshots, and testing AI-generated graphics. You’ll see where AI shines, where it struggles, and how

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37:29

How to Use Your IRA to Invest in Real Estate &...

RealDealChat / Lessons from Real Estate Investors ·

2025/09/23

Henry Yoshida of Rocket Dollar explains how to use IRAs for real estate, crypto, and private deals—unlocking $18T in retirement funds for alternatives.In this episode of RealDealChat, Jack sits down with Henry Yoshida, co-founder & CEO of Rocket Dollar (a subsidiary of Retired.com), to explore how investors can unlock the power of retirement accounts for real estate, crypto, and private investments.Henry shares his journey from financial advisor to wealth-tech entrepreneur, building platforms

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36:44

Unlock $250K in 0% Business Credit | Patrick Pychynski

RealDealChat / Lessons from Real Estate Investors ·

2025/09/20

Patrick Pychynski reveals how to access $50K–$250K in 0% business credit, avoid high-interest traps, and become bankable for long-term success.In this episode of RealDealChat, Jack sits down with Patrick Pychynski, founder of StackingSuccess.com, to discuss how entrepreneurs and real estate investors can unlock business funding the right way.Patrick shares his journey from the U.S. Marine Corps to building businesses, struggling with cash flow, and ultimately mastering the art of business credit. He

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18:26

Property Management, Permits & Profits in Chicago |...

RealDealChat / Lessons from Real Estate Investors ·

2025/09/18

Michael Root shares how he builds value in Chicago multifamily, streamlines property management, and uses in-house contracting to boost efficiency.In this episode of RealDealChat, Jack sits down with Michael Root, co-founder of Root Property Group (RootPG.com), to discuss property management, multifamily acquisitions, and why Chicago remains both a challenging and rewarding market.Michael shares how his team handles everything from general contracting to property management in-house, which helps

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35:55

Investing Overseas & Expat Wealth Strategies | Mikkel...

RealDealChat / Lessons from Real Estate Investors ·

2025/09/16

Mikkel Thorup shares how he built an 8-figure global real estate portfolio, lives in 9 countries, and helps investors create offshore wealth strategies.In this episode of RealDealChat, Jack sits down with Mikkel Thorup, host of the Expat Money Show and founder of ExpatMoney.comMikkel shares his inspiring journey from being labeled with a “learning disability” and dropping out of school at 15, to traveling to 120+ countries, living in 9, and building an 8-figure international real estate portfolio.We

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35:08

From Hulu to Real Estate Success: Dedric & Krystal...

RealDealChat / Lessons from Real Estate Investors ·

2025/09/13

Dedric & Krystal Polite share how they built a real estate empire, landed a Hulu TV show, and created a wealth education platform for new investors.In this episode of RealDealChat, Jack sits down with Dedric & Krystal Polite, stars of Hulu’s 50/50 Flip and founders of Polite Wealth Portal, to discuss their journey from 9–5 jobs to becoming respected real estate investors, educators, and TV personalities.The Polites share how social media led to their Hulu deal, why their motto is “doing good

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28:53

AI, Home Buying & Commission Rebates: Paul Cecil on...

RealDealChat / Lessons from Real Estate Investors ·

2025/09/11

Paul Cecil of ReAlpha shares how AI, commission rebates, and acquisitions are disrupting home buying—and what it means for buyers and investors.In this episode of RealDealChat, Jack sits down with Paul Cecil, President of ReAlpha (NASDAQ: AIRE), to discuss how his company is transforming real estate through AI and innovative business models.Paul explains how ReAlpha offers up to 80% of the buy-side commission back to buyers, why technology can make homes more affordable, and how acquisitions are

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30:59

Mobile Home Park Investing Myths vs Reality | Brad...

RealDealChat / Lessons from Real Estate Investors ·

2025/09/09

Brad Johnson breaks down mobile home park investing—debunking myths, sharing value-add strategies, and explaining why this asset thrives in housing crises.In this episode of RealDealChat, Jack sits down with Brad Johnson, co-founder of Vintage Funds, to discuss why mobile home parks are one of the most misunderstood—and potentially profitable—asset classes in real estate.Brad explains why one in 20 Americans lives in a mobile home, how this sector solves the affordable housing crisis, and why stigma

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30:36

From $2.5M in Debt to Commercial Real Estate Success...

RealDealChat / Lessons from Real Estate Investors ·

2025/09/06

Paul Moore of Wellings Capital shares lessons from losing millions, shifting into recession-resistant assets, and building a fund with 990+ investors.In this episode of RealDealChat, Jack sits down with Paul Moore, managing partner at Wellings Capital, to discuss his journey from engineering and entrepreneurship to becoming a respected commercial real estate fund manager.Paul shares the mistakes that took him from $1.5M in the bank to $2.5M in debt, and the key lessons that reshaped his investing

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37:55

Financial Freedom at 29: Tanisha Souza’s Income...

RealDealChat / Lessons from Real Estate Investors ·

2025/09/04

Tanisha Souza became financially free at 29 using her patented Income Snowball system. Learn how passive income can replace your 9–5 forever.In this episode of RealDealChat, Jack sits down with Tanisha Souza, attorney-turned-investor and founder of Tardus Wealth Strategies, to discuss her journey to financial freedom and her unique Income Snowball System.Tanisha shares how she went from a burned-out attorney with $100K in student loans to financially free by age 29—replacing her income through smart

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25:51

From Renovations to Ground-Up: Daniel Angel on Single...

RealDealChat / Lessons from Real Estate Investors ·

2025/09/02

Daniel Angel of Apex Investments shares how he shifted from flips to ground-up construction, multifamily acquisitions, and a fixed-return Infinity Fund.In this episode of RealDealChat, Jack sits down with Daniel Angel, co-founder of Apex Investments, to discuss his journey from corporate finance to building a diversified real estate investment company in Atlanta.Daniel explains how Apex evolved from single-family renovations into ground-up construction, build-to-rent communities, and multifamily

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35:15

How Billionaires Think: Richard C. Wilson on Wealth,...

RealDealChat / Lessons from Real Estate Investors ·

2025/08/30

Richard C. Wilson reveals lessons from interviewing 100+ billionaires, building family offices, and what investors must know about wealth, mindset, and AI.In this episode of RealDealChat, Jack sits down with Richard C. Wilson, founder of FamilyOffices.com and host of Billionaires.com, to discuss his journey building the world’s largest family office investor club, interviewing billionaires, and creating AI tools for investors.Richard has hosted 300+ investor events, interviewed over 100 billionaires

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35:27

Infinite Banking Explained: Richard Canfield on...

RealDealChat / Lessons from Real Estate Investors ·

2025/08/28

Richard Canfield breaks down infinite banking, family wealth systems, and why mindset—not money—is the foundation of generational wealth.In this episode of RealDealChat, Jack sits down with Richard Canfield of CashFollows.com to dive deep into infinite banking, family banking meetings, and how to create true generational wealth that lasts.Richard shares insights from his latest books—including Don’t Spread the Wealth and Diapers to Dollars—and explains why legacy isn’t just about money, but the

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30:48

From Dentist to Investor: How Blaine McLaughlin...

RealDealChat / Lessons from Real Estate Investors ·

2025/08/26

Tired of weak 401k returns? Discover how Blaine McLaughlin pivoted from dentistry to real estate investing and created a real path to retirement.In this episode of RealDealChat, Jack sits down with Blaine McLaughlin, a practicing dentist who realized after decades of “doing everything right” that his 401k was delivering a disappointing 3% return.That gut punch forced him to rethink retirement and turn toward real estate investing as a way to build wealth and gain true financial freedom. Blaine

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31:24

Designing for Science: Jon Howard on Real Estate,...

RealDealChat / Lessons from Real Estate Investors ·

2025/08/23

Discover how lab design and science-focused real estate is transforming investing, with Jon Howard of HED sharing strategies, challenges, and insights.In this episode of RealDealChat, Jack sits down with Jon Howard, architect and sector leader at HED, to explore the specialized world of designing for science-based tenants — from biopharma labs to advanced manufacturing facilities.Jon shares his career journey, why science-focused real estate is a growing asset class, and how design decisions can

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28:25

From Engineer to Investor: Lane Kawaoka’s Wealth...

RealDealChat / Lessons from Real Estate Investors ·

2025/08/21

From engineer to real estate syndicator, Lane Kawaoka reveals how he built financial freedom through rentals, syndications, and forced appreciation.In this episode of RealDealChat, Lane shares his journey from buying his first rental in 2009 to scaling into 11 single-family homes, then making the leap into commercial real estate and syndications. We cover the lessons learned from out-of-state investing, the challenges of scaling with rentals, and why appreciation strategies often beat pure cash

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27:06

From Flipping Hundreds of Homes to Private Lending...

RealDealChat / Lessons from Real Estate Investors ·

2025/08/19

Discover why seasoned investor Rich Lennon walked away from flipping and rentals after hundreds of deals — and how he built a thriving private lending business with returns that beat traditional investing. In this conversation, Rich shares his biggest lessons learned, including why expanding outside your market can be costly, the real truth about BRRRR returns, and how “lazy money” partners fit into his lending model.We also dive into his philosophy on wealth-building, mistakes to avoid, and even

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43:15

Wholesaling Baby Steps: Chris Logan’s Simple Path to...

RealDealChat / Lessons from Real Estate Investors ·

2025/08/16

Learn the exact baby steps to start virtual wholesaling from industry pro Chris Logan. Discover how to find buyers first, market to motivated sellers, and close deals without using your own money.In this episode, Chris shares his proven formula for picking the right market, building a buyer list fast, and using cold calling to generate leads. We break down the 4 pillars of motivation, how to protect deals when working virtually, and why mindset is 80% of wholesaling success.If you’re ready to start

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