RealDealChat / Lessons from Real Estate Investors

Debbi DiMaggio shares her 35-year real-estate journey, mindset strategies, and how AI & authenticity help agents and investors thrive in any market.

In this episode of RealDealChat, Jack Hoss sits down with Debbi DiMaggio — luxury real-estate icon, author, speaker, and coach at CoachWithDebbi.com — to unpack the habits, mindset, and authenticity that built her 35-year career.

Debbi reveals how she launched a brokerage during the 2009 recession, built lasting client relationships through transparency, and now teaches agents and investors how to create freedom using systems, collaboration, and AI.

You’ll learn why mindset beats the market...

Jack Hoss compares the top AI vibe coding tools—V0, Bolt, Replit, and Lovable—to find the fastest, easiest way to build real estate funnels.

In this RealDealCast episode, Jack Hoss tests four of the most talked-about AI website-building platforms — V0, Bolt, Replit, and Lovable — to see which one actually delivers the best results.

He gives each platform the same prompt and compares the output, layout, and usability when creating a simple real estate funnel page. You’ll discover which AI coding tools save time, where they fall short, and how real estate investors can leverage t...

Attorney Luke Carlson explains how homeowners and investors can protect themselves from bad HOAs, understand their rights, and turn risk into opportunity.

In this episode of RealDealChat, Jack Hoss sits down with Luke Carlson, founding attorney of LS Carlson Law and author of The Homeowner’s Guide to Defending Against Bad HOAs, to uncover what every real estate investor and homeowner needs to know about HOA law.

Luke shares how he became one of the nation’s leading voices for homeowner rights, the psychology behind “bad boards,” and how to protect yourself when an HOA turns ro...

Cody Hofhine shares how to build a 7-figure wholesaling business, lead better teams, and buy back your time through delegation, systems, and mindset.

In this episode of RealDealChat, Jack sits down with Cody Hofhine, co-founder of Joe Homebuyer and former leader of Wholesaling Inc., to talk about how to grow a real estate business that gives you time freedom — not just financial success.

Cody breaks down how leadership, mindset, and systems are the real multipliers in real estate. He reveals how he went from working 80-hour weeks to scaling a nationwide franchise, why most investors lo...

Max Emory shares how real estate investors can simplify bookkeeping, avoid IRS headaches, and create “decision-ready” financials to grow their profits.

In this episode of RealDealChat, Jack Hoss sits down with Max Emory, founder of Time Capital Bookkeeping, to discuss how real estate investors can master their numbers, avoid tax-time chaos, and make smarter decisions using clean, actionable financials.

Max started as a real estate investor and Marine Corps officer, scaled to 25 units, and then built a bookkeeping firm focused exclusively on investors. His team helps clients eliminate messy books, create clear KPIs, and turn data...

Ladislas Maurice, “The Wandering Investor,” shares how to build global freedom through international real estate, second passports, and frontier markets.

In this episode of RealDealChat, Jack sits down with Ladislas Maurice, founder of The Wandering Investor, to discuss the power of international investing and how real estate can become your ticket to global diversification, second citizenship, and long-term financial freedom.

Ladislas shares his journey from Nestlé executive in Africa to full-time investor traveling the world, buying real estate in frontier markets, and helping clients unlock second residencies and passports through smart investments.

Here’s what...

Franchise expert Kim Daly explains how real estate investors can build scalable, semi-active businesses that create wealth, freedom, and long-term cash flow.

In this episode of RealDealChat, Jack sits down with Kim Daly, founder of The Daly Coach and one of the top franchise consultants in the U.S., to talk about how real estate investors can use franchising to diversify their portfolios and create predictable, scalable income streams.

Kim breaks down the “semi-active investor” model, explains why franchising is the bridge between entrepreneurship and investing, and shares how she’s helped hundreds of people replac...

Learn how cost segregation helps real estate investors save thousands in taxes. In this video, Gian Pazzia of KBKG breaks down how bonus depreciation, 1031 exchanges, and other real estate tax strategies can accelerate your wealth-building plan.

In this episode of RealDealChat, Jack Hoss interviews Gian Pazzia, CCSP and President of KBKG — creators of CostSegregation.com — to uncover how investors use cost segregation studies to maximize deductions, reduce taxable income, and boost passive income from real estate.

They cover when cost segregation makes sense, how to combine it with bonus depreciation, and why 1031 exchanges are still one...

George Dimov, CPA, shares the biggest tax mistakes real estate investors make, why proactive planning matters, and how to build smarter portfolios.

In this episode of RealDealChat, Jack sits down with George Dimov, CPA and founder of DimovTax.com, to discuss proactive tax planning, common mistakes investors make, and why accounting + real estate go hand in hand.

George shares his journey from immigrant beginnings to building a tax practice that serves thousands of clients nationwide. He explains why he invests heavily in real estate himself, how tax strategies like cost segregation and 1031 exchanges really work...

Katie Kim shares how she turned a $50K bakery investment into a $5.5M project, scaled her family business, and now teaches others to develop smarter.

In this episode of RealDealChat, Jack sits down with Katie Kim, real estate developer, CCIM, and founder of The Kim Group, to talk about her journey from growing up in a construction family to leading multimillion-dollar development projects.

Katie reveals how she turned a $50K bakery investment into a $5.5M project, why scars and setbacks led her to get her CCIM designation, and how she now teaches aspiring developers to...

David Christensen shares how storytelling, mindset, and authenticity helped him sell 400+ homes, including the Breaking Bad house, and rebuild his life.

In this episode of RealDealChat, Jack sits down with David Christensen (DavidChristensen.com) to discuss his extraordinary journey—from managing platinum-selling musicians and even working on Titanic research dives, to becoming a nationally recognized luxury real estate agent.

David opens up about his path through addiction and recovery, and how mindset, authenticity, and service-first leadership transformed his career. He explains how storytelling is the secret weapon in real estate, why emotions drive home buying de...

Gideon Spencer shares how he scaled from a cash-flowing fourplex to $6M in boutique hotels using automation, creative financing, and the mentor flywheel.

In this episode of RealDealChat, Jack sits down with Gideon Spencer, real estate investor and founder of a new boutique hotel community, to discuss how he scaled from a fourplex short-term rental to multi-million-dollar boutique hotels in just two years.

Gideon shares his origin story in tech, the family health crisis that fueled his drive for automated wealth, and how he uses systems, teams, and creative financing to scale fast. He also...

Claude Sonnet 4.5 brings powerful AI agents, coding tools, and automation upgrades—here’s how real estate investors can use them to save time.

In this episode of RealDealCast, Jack Hoss breaks down Anthropic’s release of Claude Sonnet 4.5 and what it means for real estate professionals.

From AI agents that can run tasks for 30+ hours straight to improved coding, automation, and Chrome extensions, this update is a game-changer. Jack explains how these tools compare to ChatGPT and Gemini, and more importantly, how investors can use them to cut busy work and focus on building wealth.

Y...

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 management is often overlooked, how to avoid common investor mistakes, and why focus and systems (like EOS) have be...

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 building Kraft Capital with partners and launching a new flex fund. He also explains why sett...

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 investors can leverage these tools to focus on growing their business instead of getting stuck in busy work.

Whether you’re new to A...

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 that custody over $12B in assets. He explains why traditional advisors rarely mention self-directed IRAs, how Rocket Dollar makes alternative in...

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 explains how his team helps investors access 0% interest funding while building a truly “bankable” business that attracts long-term financing.

H...

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 reduce costs, improve communication, and streamline renovations.

Key takeaways from this conversation include:

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.com

Mikkel 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 cover:

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 while doing well,” and how they built a business model that blends wealth-building with communit...

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 helping them build an end-to-end home buying platform.

Here’s what you’ll learn in thi...

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 keeps many investors out of the space. He also shares his approach to building long-term cash flow r...

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 philosophy. He breaks down why chasing shiny objects nearly destroyed his wealth, and why true success in real...

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 real estate investing. She explains why passive income is the ultimate wealth strategy, how she and her husband built their port...

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 value-add acquisitions. He also introduces Apex’s Infinity Fund, a fixed-return investment vehicle designed for accredited investors seeking certainty and flexibility.

Key takeaways from this co...

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 and 70 pro athletes, and built AI-powered tools that synthesize insights from 1,500+ talks. In this conversation, he shares:

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 knowledge, systems, and mindset we pass down.

Here’s what we cover:

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 shares:

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 make or break a property’s ability to attract tenants. Topics include:

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 flow.

📌 Timestamps:

00:00 – Lane’s journey from engineer to real estate investor

02:00 – First rental property & the spark for financial freedom

03:0...

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 how he teaches his kids about money with the "Lennon Bank." Whether you’re new to real estate or a season...

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 or scale your real estate investing business, this conversation is packed wi...

Work 30 minutes a month & earn thousands in passive income! Dustin Heiner shares proven real estate investing tips for financial freedom.

Stop selling your life for a paycheck. Real estate investor Dustin Heiner reveals how he works just 30 minutes a month on his rental portfolio—while generating thousands in passive income. Learn his exact strategies for finding off-market deals, building a business that runs itself, and setting a 10-year “quit your job” deadline. Dustin shares tactical tips on buy boxes, subject-to deals, and why high interest rates can actually be a good thing.

Full episode highlights:

Struggling to break past an income ceiling? Dr. Noah St. John reveals how to merge inner game and outer game strategies to create unstoppable momentum and “hockey stick” growth in your real estate investing or business journey.

In this episode of RealDealChat, we cover:

Sree Varma reveals how he raised £2.8M in private finance, scaled premium co-living projects, and built a £6.5M portfolio in just 12 months.

In this episode of RealDealChat, Sree Varma shares his inspiring journey from arriving in the UK with £150 to building multiple successful businesses — including a £6.5M premium co-living property portfolio in just one year.

We dive into:

Entrepreneur & investor Jeremy Delk reveals how losing $2M led to real estate wins, venture capital success, and a no-plan growth strategy.

In this episode of Real Deal Chat, Jeremy Delk shares his incredible journey — from teenage day trader to becoming Fidelity’s youngest trader, losing $2 million in four days, and building a diversified empire in venture capital, real estate, healthcare, and hospitality.

We dive into:

Discover how Brian Grimes skyrocketed from 10 deals to over 300 in real estate investing! In this inspiring episode of the REI Mastermind Network, Brian shares the innovative strategies that helped him scale fast, build generational wealth, and create a seamless investment process with his "done-for-you" programs. If you're ready to take your real estate game to the next level, this episode is packed with actionable insights and proven techniques.

🎯 What You'll Learn in This Episode:

Unlock the key to scaling success in real estate investing with Jason Cook! In this episode of the REI Mastermind Network, Jason shares his incredible journey from corporate sales to building a thriving business—and reveals the strategies every real estate investor must know to scale efficiently. Whether you're managing multifamily assets or growing an investment portfolio, this conversation is packed with actionable insights.

🎯 What You'll Learn in This Episode:

Discover how Chris A. Williams skyrocketed from having just $30 to achieving over $60M in real estate sales—all by the age of 25! In this episode, Chris shares his inspiring journey from being a young agent with no real estate background to building a thriving real estate brokerage, mastering creative financing, and helping others achieve generational wealth.

What you'll learn in this video:

- How Chris turned challenges into opportunities and built a $60M real estate empire.

- The power of creative financing, like subject-to deals, to maximize cash flow.

- Why bu...