Real Estate Investing with RealDealCrew

RealDealCrew / Jack Hoss
  • 4.9 (82)
  • Investing
  • Updated Semiweekly

Real Estate Investing with RealDealCrew 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 focuses on practical execution — not theory. Whether you're wholesaling houses, flipping properties, building a rental portfolio, or scaling a real estate investing business, this podcast delivers real-world lessons from operators actively doing deals. Follow the show to get weekly insights on real estate investing strategies, deal flow systems, and operational growth.

  1. 3d ago

    Commercial Real Estate Lessons From Losing 200 Units in 2008 w/ Stewart Heath

    Stewart Heath lost 200 units in 2008 by trusting the bank. Now he buys only boring, stabilized commercial real estate. Stewart Heath is a CPA with more than 35 years of experience and a returning RealDealChat guest. Before 2008 he owned about 200 units across Nashville and Franklin, Tennessee, and he let his lenders' approval stand in for his own underwriting. Today his firm buys only stabilized medical office, suburban office, and mixed-use properties along the I-65 corridor from Nashville to Birmingham, using fixed-rate debt and a simple motto: boring is beautiful. He and Jack cover what 2008 taught him, why deals still work at 2026 rates, and why he thinks off-market deals are overrated. Questions answered in this episode: Can you trust a bank's approval as a second opinion on your deal?Do commercial real estate deals still pencil with rates near 6%?Why didn't the commercial "debt wall" create the distressed deals investors expected?Is medical office a better investment than self-storage right now?Are off-market commercial deals really better than listed ones? Stewart Heath is a CPA, commercial real estate investor, and author of the free book Don't Do What I Did. His firm buys and manages stabilized commercial properties for investors seeking tax-advantaged cash flow. 📘 Get Stewart's free book: https://harvardgracecapital.com/book/ Work With RealDealCrew If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper: Take the Deal Intake Assessment See how resilient your current operation actually is. → https://assessment.realdealcrew.com Book a Fit Call If you want to explore what a fully system-driven deal flow looks like, let’s talk. → https://realdealcrew.com/book LIKE • SHARE • JOIN • REVIEW WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram

    Commercial Real Estate Lessons From Losing 200 Units in 2008 w/ Stewart Heath

  2. 5d ago

    Tax Lien Investing: 13-18% Secured by Real Estate w/ Stephen Morel

    Banks have earned 13 to 18% on unpaid property taxes for 100 years. Here's how tax liens work. Every year, over $20 billion in property taxes goes unpaid in America, and investors buy billions of that debt from counties as tax liens. The returns are strong and secured by real estate, but 50 different state rulebooks have kept the game mostly in the hands of hedge funds and banks. Stephen Morel is a 20-year title attorney out of New Orleans. After Hurricane Katrina flooded his home, he built a title insurance program that put roughly 12,000 abandoned properties back into productive use. Now he's founder of JurisDeed, a platform built to make tax lien investing accessible to everyday investors. In this episode: How a tax lien works, and why it's like buying a mortgage from the countyWhy about 90% of tax liens pay back with interest, and only about 1% end in foreclosureWhy state-by-state laws keep most investors outHow Stephen uses AI to build legal tech where "mostly right" means you loseRapid fire: the lie investors tell themselves, his first hire, and his biggest time saver Guest: Stephen Morel, founder of JurisDeed and host of the Innovative Investor podcast Links: Get on the JurisDeed waitlist (closed beta): https://jurisdeed.comListen to Innovative Investor: https://podcasts.apple.com/us/podcast/the-innovative-investor-podcast-property-debt-wealth/id1877715388 #TaxLienInvesting #TaxLiens #RealEstateInvesting #PassiveIncome #TaxDeeds #AlternativeInvestments #RealEstateAttorney #TitleInsurance #PropTech #AIinRealEstate #HurricaneKatrina #NewOrleans #InvestingForBeginners #RealDealChat Work With RealDealCrew If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper: Take the Deal Intake Assessment See how resilient your current operation actually is. → https://assessment.realdealcrew.com Book a Fit Call If you want to explore what a fully system-driven deal flow looks like, let’s talk. → https://realdealcrew.com/book LIKE • SHARE • JOIN • REVIEW WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram

    Tax Lien Investing: 13-18% Secured by Real Estate w/ Stephen Morel

  3. Sep 27

    How to Niche Down in Commercial Real Estate w/ Bob Knakal

    Bob Knakal has closed $25 billion in NYC real estate by doing less. Here's how saying no built his career. After 43 years brokering New York real estate, two firings from the biggest firms in the business, and a fresh start with BKREA in 2024, Bob Knakal sold 43 properties for $1.8 billion in his first full year back on his own. He joins Jack to break down why narrowing your focus beats chasing every deal, and how proprietary information and relentless fundamentals create an edge nobody can copy. In this episode: Why Bob turns down 3 to 4 times more listings than he competes forThe Map Room: 220 hours walking an empty Manhattan that won 104 of 106 listing pitchesHow specializing literally creates timeThe Stonecutter's Creed and why most brokers quit too soonWhy AI will push more professionals out of big firms and into boutiques Bob Knakal is the founder of BKREA and co-founder of Massey Knakal Realty Services, which sold to Cushman & Wakefield for $100 million. He has closed 2,422 deals covering 100 million square feet and co-wrote Selling Buildings: A Tactical Playbook with Rod Santomassimo. Connect with Bob: 🌐 https://bkrea.com 📧 bk@bkrea.com 📞 917-509-9501 #RealDealChat #CommercialRealEstate #RealEstateInvesting #CRE #RealEstateBroker #NYCRealEstate #BobKnakal #Specialization #AIinRealEstate #Entrepreneurship #SalesTips #ProspectingCalls #RealEstateDevelopment #BrokerLife Work With RealDealCrew If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper: Take the Deal Intake Assessment See how resilient your current operation actually is. → https://assessment.realdealcrew.com Book a Fit Call If you want to explore what a fully system-driven deal flow looks like, let’s talk. → https://realdealcrew.com/book LIKE • SHARE • JOIN • REVIEW WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram

    How to Niche Down in Commercial Real Estate w/ Bob Knakal

  4. Sep 25

    AI and Real Estate: Why Rentals Are Now a Must w/ Dustin Heiner

    AI is cutting white-collar jobs fast. Dustin Heiner explains why rental cash flow is now a must. After 20 years of telling people they should invest in real estate, Dustin changed his message. With AI layoffs hitting tech, bookkeeping, and customer service, he now says you must. Dustin has been "successfully unemployed" for 10 years, owns 30+ single-family rentals and roughly 1,000 apartment units, and made more money during the 2008 crash than before it. He and Jack get into why cash flow holds up when jobs and markets don't, and why most people who buy rentals are running a hobby, not a business. In this episode: The $500 a month rule and how 20 rentals becomes $120K a yearWhy shelter is the income stream AI can't take overThe green light / red light system for killing bad deals earlyWhy you call the property manager before you make an offerThe 6 ways one rental property makes you money Dustin Heiner hosts the Master Passive Income podcast, with 2.3 million downloads and a top ranking for real estate investing on Apple Podcasts, and built the Income Builder deal analysis platform. 🔗 Dustin's deal analyzer (free account): https://incomebuilder.io 📚 Dustin's free course: text RENTAL to 33777 or visit masterpassiveincome.com/freecourse 📱 Instagram: @thedustinheiner 🔗 Build systems for your investing business: https://realdealcrew.com #RealEstateInvesting #PassiveIncome #RentalProperty #CashFlow #AIJobs #FinancialFreedom #IncomeBuilder #BuyAndHold #RealEstateBusiness #LandlordLife #GenerationalWealth #DustinHeiner #MasterPassiveIncome #RealDealChat Work With RealDealCrew If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper: Take the Deal Intake Assessment See how resilient your current operation actually is. → https://assessment.realdealcrew.com Book a Fit Call If you want to explore what a fully system-driven deal flow looks like, let’s talk. → https://realdealcrew.com/book LIKE • SHARE • JOIN • REVIEW WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram

    AI and Real Estate: Why Rentals Are Now a Must w/ Dustin Heiner

  5. Sep 23

    Should You Sell Your Rentals? Why "Never Sell" Costs Investors w/ Chris Lopez

    Your rental equity might be earning 2%. Chris Lopez explains when to sell, 1031, or redeploy it. Chris Lopez ran a Denver investment brokerage doing $100 million a year in transactions and built Property Llama, software that helps landlords decide what to do with rentals they already own. He walks through the zero-down condo he 1031'd into a fourplex for 5X the cash flow, why he later sold his rentals (and their sub-4% mortgages) to invest in real estate lending funds, and the simple test every landlord should run before renewing a lease. In this episode: Why your return should be measured on equity, not what you put downThe 1031 trap: saving a dollar in taxes and losing ten in returnsHow Chris 6X'd his cash flow by moving from rentals into debt fundsThe "would I buy this again?" question to ask before every lease renewalHow AI is changing underwriting, tenant fraud, and due diligence About Chris: Chris Lopez is the co-founder of Property Llama and Property Llama Capital, a former Denver investment broker, and a longtime landlord with a background in financial planning. Links: 🦙 Property Llama: https://propertyllama.com 💰 Property Llama Capital: https://propertyllamacapital.com #RealEstateInvesting #1031Exchange #RentalProperty #Landlord #CashFlow #PassiveIncome #RealEstateDebtFund #BuyAndHold #ReturnOnEquity #PassiveInvesting #RealEstateTips #PropertyManagement #RealDealChat Work With RealDealCrew If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper: Take the Deal Intake Assessment See how resilient your current operation actually is. → https://assessment.realdealcrew.com Book a Fit Call If you want to explore what a fully system-driven deal flow looks like, let’s talk. → https://realdealcrew.com/book LIKE • SHARE • JOIN • REVIEW WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram

    Should You Sell Your Rentals? Why "Never Sell" Costs Investors w/ Chris Lopez

  6. Sep 21

    Why Commercial Real Estate Deals Die Before Closing w/ Richard Crouch

    Most commercial real estate deals don't die on the numbers. Here's what actually kills them. Richard Crouch has spent 25 years on the legal side of commercial real estate at Woods Rogers, working with first-time commercial buyers and large syndication sponsors alike. He walks through why slow turnaround erodes confidence in a deal, what off-the-shelf operating agreements leave out, and how to protect your due diligence period before you sign. In this episode: Why "time kills deals" and how a report nobody ordered can push closing 30 daysOperating agreement provisions for capital calls, dilution, and removing an underperforming sponsorWhat lenders expect before they'll extend a loan maturityThe binding clauses hiding in a "non-binding" LOIThe PSA language that keeps your due diligence clock from starting until the seller delivers About Richard: Richard Crouch is a commercial real estate attorney at Woods Rogers with 25 years of experience in acquisitions, financing, and syndications, with much of his client work concentrated in the Southeast. 🔗 Learn more about Richard and his team: https://woodsrogers.com 🔗 Build systems for your investing business: https://realdealcrew.com Work With RealDealCrew If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper: Take the Deal Intake Assessment See how resilient your current operation actually is. → https://assessment.realdealcrew.com Book a Fit Call If you want to explore what a fully system-driven deal flow looks like, let’s talk. → https://realdealcrew.com/book LIKE • SHARE • JOIN • REVIEW WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram

    Why Commercial Real Estate Deals Die Before Closing w/ Richard Crouch

  7. Sep 19

    AI for Small Business Owners: 20 Hours a Week of Testing w/ Brent Stewart

    Brent Stewart spent 20 hours a week for four months testing AI, and says refusing to use it is the real liability. Brent Stewart has practiced law for 30 years in Rock Hill, South Carolina, fighting insurance companies as a trial lawyer. He also owns the office buildings his own firm rents. Over the last four months he set aside 20 hours a week to work through every legal AI system he could find, and he came out of it with a position most people do not expect from an attorney: the people refusing to learn these tools are the ones creating exposure, for their clients and for their employer. This conversation gets into what he actually built, what it cost him, and what he got wrong first. He walks through why his AI is walled off from the open internet, the vendor contract structure he now insists on, and the mistake that cost him thousands of dollars before it taught him anything useful. On the real estate side, Brent bought his office buildings through a separate entity that rents to the law firm, then restructured ownership so his wife qualifies as active manager. That change let him run the losses against his law firm income instead of depreciating remodels slowly over time. What you will learn: Why he keeps his AI in-house and never lets it pull case law off the open internetThe AI vendor contract he recommends: lock the price for three years, keep a one-year outHow a 10 percent ownership change and active manager status unlocked accelerated depreciationWhy he tells his AI to argue with him instead of agreeing with himHow he can now spot which opposing counsel are using AI, just from how fast discovery comes back About the guest: Brent Stewart is the founder of Stewart Law Offices, a personal injury and workers' compensation firm he started in 1995 after running a market study to pick his location. He graduated law school in 1989 and still keeps every deadline in a paper calendar. Links: 🔗 Brent Stewart: https://StewartLawOffices.net 📞 866-STEWART 🔗 Build systems for your investing business: https://realdealcrew.com #RealEstateInvesting #AIForBusiness #LegalTech #AIAutomation #RealDealChat #CommercialRealEstate #AcceleratedDepreciation #BusinessSystems #RealEstateTax #SmallBusinessOwner #AITools #LawFirmManagement #Entrepreneurship Work With RealDealCrew If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper: Take the Deal Intake Assessment See how resilient your current operation actually is. → https://assessment.realdealcrew.com Book a Fit Call If you want to explore what a fully system-driven deal flow looks like, let’s talk. → https://realdealcrew.com/book LIKE • SHARE • JOIN • REVIEW WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram

    AI for Small Business Owners: 20 Hours a Week of Testing w/ Brent Stewart

  8. Sep 17

    Cost Segregation on Single Family Rentals w/ Joe Viery

    Cost segregation is not just for big buildings. Joe Viery on what a single family study really costs. Joe Viery has been running cost segregation studies since 2007 and founded US Tax Advisors Group in 2016. He has completed studies in all 50 states, and his argument in this conversation is direct: the strategy investors assume is reserved for downtown office towers now works on a fourplex or a single family rental, and most owners have never heard of it because their accountant doesn't know it is available at that price point. Joe walks through what a study on a single family home actually costs, the 10x rule he uses to tell people when not to hire him, how far back you can reach on a property you already own, and what separates an engineer-based study from the DIY software versions that put the burden of the numbers on you. He also covers the passive versus active distinction and the $25,000 loss cap that can undo the whole benefit for a passive investor. Key takeaways: A single family study runs about $1,000 or less, and Joe will tell you not to do it if he cannot save you ten times the feeYou can reach back roughly 15 years from the date you acquired the property, not the date it was builtDIY cost seg software makes you supply the quantities, and Joe calls that an open invitation to an auditState conformity varies: California does not allow cost segregation against state tax, Arizona does179D and 45L came off the table as of June 30, so energy retrofit incentives are no longer in playPassive investors cap out at $25,000 in usable losses, which can blow up an otherwise strong study About the guest: Joe Viery is the founder of US Tax Advisors Group (USTAGI), a cost segregation firm serving investors from single family rentals to multi-million dollar commercial properties. He is not an accountant and does not provide tax or legal advice. His studies go to your accountant, who applies the results. Links: Free benefit estimate from Joe's team: https://ustagi.com Build systems for your investing business: https://realdealcrew.com #CostSegregation #RealEstateInvesting #RentalProperty #BonusDepreciation #RealEstateTaxes #TaxStrategy #SingleFamilyRental #PassiveIncome #RealDealChat #DepreciationDeduction #SmallMultifamily #LandlordTips Work With RealDealCrew If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper: Take the Deal Intake Assessment See how resilient your current operation actually is. → https://assessment.realdealcrew.com Book a Fit Call If you want to explore what a fully system-driven deal flow looks like, let’s talk. → https://realdealcrew.com/book LIKE • SHARE • JOIN • REVIEW WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram

    Cost Segregation on Single Family Rentals w/ Joe Viery
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Real Estate Investing with RealDealCrew 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 focuses on practical execution — not theory. Whether you're wholesaling houses, flipping properties, building a rental portfolio, or scaling a real estate investing business, this podcast delivers real-world lessons from operators actively doing deals. Follow the show to get weekly insights on real estate investing strategies, deal flow systems, and operational growth.

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