Real Estate Investing with RealDealChat

RealDealCrew / Jack Hoss
  • 5.0 (80)
  • INVESTING
  • UPDATED SEMIWEEKLY

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 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. Timberland Investing: Multiple Paydays from One Property w/ John Brenard

    9H AGO

    Timberland Investing: Multiple Paydays from One Property w/ John Brenard

    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 to democratize the asset classWhy the Southeast US (Georgia, North Florida, South Carolina, Alabama) is now the #1 timber region in North AmericaThe three ways a single property can generate returns: timber harvest, real estate appreciation, and development or recreational saleHow Southview sources deals entirely through personal relationships — and why outsiders simply can't access the same pipelineThe sweet spot: 200–2,000-acre mid-size properties that fall below institutional radar and above most individual investor budgetsUnderwriting criteria: proximity to mills (within 50 miles), soil productivity, access roads, and multiple buyer optionsWhy timberland investors can wait for the best timber prices — unlike farmland, there's no forced harvestHow demographic migration from the Northeast and West Coast is driving rural land values up in the SoutheastThe 500-acre deal they bought for $1M and exited in 60 days — selling parcels to a business and an adjacent landownerWhy John is cautious about AI-labeled startup investments — and why he prefers assets you can put boots on the ground to verifyCurrent bottleneck: capital. They have deal flow. The fund is nearly deployed and raising toward $50M. This episode is for: Accredited investors looking for non-correlated, tangible alternatives to stocks and cryptoReal estate investors who want to understand a high-margin niche with multiple exit optionsFamily offices and RIAs seeking a conservative real assets strategy 🔗 Learn more: https://southviewtimber.com 🔗 Find John on LinkedIn: John Bernard 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

    30 min
  2. How AI Search Is Changing Where Seller Leads Come From w/ Trevor Mauch of Carrot.com

    2D AGO

    How AI Search Is Changing Where Seller Leads Come From w/ Trevor Mauch of Carrot.com

    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 growing you're dying" is a lie — and the three real reasons business existsThe difference between a logo and an actual brand — and why 8 out of 10 investors don't have oneWhy sellers ghost you (spoiler: it's almost never about price)The "evergreen marketing" principle: how to build lead flow that doesn't require constant feedingWhat a real USP looks like in 2026 — and why "cash offer, close in 7 days" stopped being one years agoThe AI continuum: from untrained ChatGPT threads to well-trained coaches to autonomous agentsHow Carrot ingests seller call conversations and auto-recommends website updates to close objection gapsHow Google's AI overviews nearly doubled daily searches — and what that means for your SEOWhy a guy in Ohio got his first ChatGPT-sourced seller lead within 3 weeks of simple brand updatesThe human-AI balance: using technology to scale humanity, not replace itWhy efficiency gains from AI tend to create more work, not more freedom — and what to do instead This episode is for: Wholesalers, flippers, and agents who keep spending on leads and not seeing resultsInvestors who want to understand how AI search is already changing inbound deal flowAnyone building or refining their online presence and brand for 2026 🔗 Learn more at: https://carrot.com 🔗 Trevor's AI Search Challenge: carrot.com #RealEstateInvesting #LeadGeneration #RealEstateBrand #WholesaleRealEstate #AISearch #RealDealChat #CarrotCom #InvestorMarketing #SellerLeads #RealEstateTips 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

    45 min
  3. The Founder Trap: Why Hard Work Is Keeping You Broke w/ Charles Gaudet

    4D AGO

    The Founder Trap: Why Hard Work Is Keeping You Broke w/ Charles Gaudet

    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 your leads can actually tank your businessWhy 66% of Inc. 5000 companies shrink, go under, or sell disadvantageously within 5–8 years of being listedThe real definition of marketing — and why even $500M CEOs don't know how to create, capture, and nurture demandWhy 100% of all buying decisions will be made before a prospect ever gets on the phone by 2030 (McKinsey and Gartner data)How he built one of the most profitable real estate development companies in his market — with zero prior experience — by working from a book and writing down contractor names off trucksThe hospital wake-up call that nearly killed him in his 20s and forced him to stop believing hard work alone was the answerReturn on Time (ROT) — the metric that separates real business owners from high-paid employeesWhy AI is just an accelerator — and why context and strategic thinking are the real competitive moatHow to use AI as a virtual board of directors, legal bot, and deal analyzer for real estate investmentsWhy Google's organic traffic dropped 60% in 2025 — and what that means for every investor's marketing plan This episode is for: Real estate investors and operators stuck between $1M and $10M who feel maxed outEntrepreneurs running a business that can't survive without themAnyone who wants to understand how to use AI strategically — not just to write emails 🔗 Learn more: https://predictableprofits.com 🔗 Build systems for your investing business: https://realdealcrew.com #EntrepreneurMindset #BusinessGrowth #RealEstateInvesting #ScalingBusiness #PredictableProfits #FounderTrap #AIForBusiness #RealDealChat #BusinessSystems #PassiveIncome 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

    47 min
  4. Why 90% of FSBOs Fail (And How to Be the 10%) w/ Tim Street

    6D AGO

    Why 90% of FSBOs Fail (And How to Be the 10%) w/ Tim Street

    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 & Promote, Sell & SecureStrategic underpricing — how Tim achieved a 102.3% list-to-sold ratio by creating competitionThe "chaos in the driveway" open house strategy that forces buyers to write offers on their steering wheelsWhy a pre-listing inspection is the single most powerful move a FSBO can make before going liveThe "truth package" that takes all negotiating ammo away from buyersHis 90-day sell guarantee — and the operational safeguard behind itWhy he quit the listing game cold after watching a retired couple get lied to for a $500K promise on a $400K houseHow he uses Claude for narrative script writing and ChatGPT for operationsHis custom Hemingway-inspired GPT that writes listing descriptions buyers actually readWhy 24 touches across 3 platforms is the real follow-up standard — not 6 This episode is for: Real estate investors who want to understand the FSBO seller mindsetHomeowners tired of paying 3–6% commissionsAgents who want to stop losing listings to overpriced competitorsAnyone building a follow-up system around a skeptical, DIY-first audience 🔗 Get Tim's Investor Power Pack: https://foolprooffsbo.com/investors 🔗 Take the FSBO temperament quiz: https://foolprooffsbo.com/quiz #FSBO #ForSaleByOwner #RealEstateInvesting #HomeSelling #RealDealChat #RealEstateTips #HouseSelling #InvestorMindset #RealEstateAgent #HomeBuying 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

    37 min
  5. The Title Insurance Mistakes That Cost Investors Everything w/ Dru Wischhover

    MAR 23

    The Title Insurance Mistakes That Cost Investors Everything w/ Dru Wischhover

    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 oneWhy title insurance covers the past, not the future (and why that matters)Two real fraud cases: a deceased man's signature forged on a deed and a $275K property sold out from under an elderly widowThe $500,000 bounced cashier's check that cost Dru clients and a builder relationshipWhy rush closings are a red flag — and what to look forHow assumptions, novations, and stacked assignments actually work from the title sideWhat wholesalers get wrong about disclosure at closingThe three things every investor should do to ensure a smooth closeWhy Dru includes attorney access in his title work — and how that protects investorsHow he's expanding into Indiana and what the scale-up bottleneck taught himHis Heroes Helping Heroes nonprofit launching in 2026 This episode is for: Wholesalers, flippers, and buy-and-hold investors who want to close cleanInvestors who've been burned by a deal falling apart at the tableAnyone who's ever wondered what a title company actually does for them 🔗 Connect with Dru on LinkedIn: search Dru Wischhover (D-R-U) #TitleInsurance #RealEstateInvesting #RealEstateFraud #WholesaleRealEstate #RealDealChat #ClosingTable #RealEstateTips #HouseFlipping #InvestorMindset #TitleCompany 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

    42 min
  6. $50K at 0% Interest: The Credit Strategy Investors Miss w/ Daniel McDavid

    MAR 21

    $50K at 0% Interest: The Credit Strategy Investors Miss w/ Daniel McDavid

    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 it can happen in 30 days)What a trade line is and how it temporarily boosts your credit score to unlock fundingHow to access $50K–$100K at 0% interest for 12 months through business creditWhat rental arbitrage is — and why you don't need to own property to cash flow on AirbnbThe FCRA rights most consumers don't know they have — and how to use themHow to spot a credit repair scam (the Zelle/Cash App red flag)The questions you should be asking any credit repair company before you signHow Daniel's wife went from employee to tax business owner — and the identity shift that made it possibleWhy Daniel was homeless for five years and how faith drove every financial decision since This episode is for: New investors who can't get funding because of their creditAnyone who's been denied and doesn't know whyEntrepreneurs ready to stop renting their future and start building itInvestors who need 0% capital to get their first deal off the ground 🔗 Find Daniel on Instagram: @DanielMcDavid1 🔗 Move Mountains Funding: https://movemountainsfunding.com #CreditRepair #RealEstateInvesting #BusinessFunding #RentalArbitrage #CreditScore #RealDealChat #FirstRentalProperty #FCRA #ZeroInterest #EntrepreneurMindset 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

    37 min
  7. From Fired to $22M in Land Development with Brandon Cobb

    MAR 19

    From Fired to $22M in Land Development with Brandon Cobb

    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 — entitlement, development, and buildingHis golden rule: don't buy land until all approvals are in place (and the seven-figure lesson he learned the hard way)Why 600+ units in the pipeline doesn't require a massive teamHow he pivoted from vertical integration to a strategic partner modelWhy raising private capital is easier than most investors thinkHow he uses custom GPTs for due diligence, zoning reviews, and contract analysisThe biohacking habits (cold plunge, no alcohol, Whoop tracking) that fuel his performanceHis free 8-hour Land Development 101 course at learnlanddevelopment.com This episode is for: Investors looking to move beyond flipping and rentalsOperators with existing cash flow who want to scale into developmentAnyone curious how to raise private capital for land dealsEntrepreneurs tired of being bottlenecked by overhead and employees 🔗 Learn more from Brandon: https://learnlanddevelopment.com #LandDevelopment #RealEstateInvesting #LandInvesting #CapitalRaising #RealDealChat #EntrepreneurMindset #LandEntitlement #HouseHacking #PrivateMoney #AIForBusiness 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

    36 min
  8. How to Invest in Real Estate Without Being a Landlord w/ Lane Kawaoka

    MAR 17

    How to Invest in Real Estate Without Being a Landlord w/ Lane Kawaoka

    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 cover: What passive real estate investing actually isHow syndications work step-by-stepWho qualifies as an accredited investorWhy high-income earners struggle to scale with rentalsThe shift from active investing to passive cashflowRisks and misconceptions in syndicationsHow to evaluate deals and operatorsWhy networking and community matter at higher levels If you’re tired of managing tenants or want to scale beyond single-family rentals, this episode will open your eyes to a different path. Timestamps: 00:00 – Intro & Meet Lane Kawaoka 01:30 – Lane’s Background & Engineering to Investing 04:00 – What Is Passive Real Estate Investing? 06:45 – Active vs Passive Investing Explained 09:30 – What Is a Syndication? 12:15 – Accredited Investor Breakdown 15:00 – Why High-Income Earners Pivot 18:40 – Risks in Passive Investing 21:30 – Evaluating Deals & Operators 24:15 – Building Wealth Through Networking 27:00 – Common Mistakes Investors Make 30:30 – Final Thoughts #PassiveIncome #RealEstateInvesting #Syndications #AccreditedInvestor #PassiveRealEstate #CashflowInvesting #MultifamilyInvesting #RealEstatePodcast #InvestorMindset #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

    47 min
See All (302)

5
out of 5
80 Ratings

About

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 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.

Information

You Might Also Like