Real Estate Investing with RealDealChat

RealDealCrew / Jack Hoss
  • 5.0 (81)
  • 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. 1d ago

    Why Your Lender Is Competing With ChatGPT w/ Aaron Marsh

    Private lender Aaron Marsh on why clients now bring ChatGPT quotes to the table, and why that backfires. Aaron Marsh runs a boutique private lending shop built for real estate investors that traditional banks can't or won't underwrite, from high-leverage beach properties to first-time buyers who got turned away everywhere else. In this episode, Aaron breaks down the new obstacle showing up in nearly every deal: clients running his loan terms through ChatGPT and coming back asking for the "better deal" the bot promised. He also covers the real down payment math on DSCR loans, what documents to have ready before you talk to any lender, where mortgage rates are realistically headed, and the AI tool quietly generating new leads for his team every night. Key topics: Why a 15% down DSCR pitch usually costs more than it looksThe down payment sweet spot between 20% and 25% for the best rateDocuments to have ready before approaching a lenderQuestions to ask a lender to know if they're a good fitWhere mortgage rates are realistically headed through 2027 and 2028 Guest bio: Aaron Marsh is a private lender serving real estate investors across Texas, Alabama, and Florida, with commercial and investment lending in over 35 states. Learn more and grab his investor playbook at marshlending.com. Links: 🔗 marshlending.com (investor playbook) 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 Your Lender Is Competing With ChatGPT w/ Aaron Marsh

  2. 3d ago

    Why This Builder Shut Down a $35M Company w/ Dave Rossi

    Dave Rossi shut down his $35 million construction company. Here's the mindset shift that followed. Dave Rossi is the founder of CQ Construction, building luxury custom homes and developments in Silicon Valley. After running a $35 to 40 million a year construction company, Dave shut it down completely rather than stay in a partnership and a life he'd come to see as wrong. In this conversation, he and Jack dig into the difference between fear-driven decisions and objective reality, why "success equals happiness" has it backwards, and the filter Dave now runs every business decision through before committing. The conversation also covers Dave's "building partner vs building vendor" model, how niching down grew his business after his reset, and a real estate story involving a $15 million teardown nobody had ever walked through. Key topics: Why he shut down a $35 to 40 million business rather than stay in a bad partnershipTelling the difference between real intuition and emotional overreactionThe building partner vs building vendor modelHow niching down grew his business post-resetA $15 million teardown, bought sight unseen Guest bio: Dave Rossi is the founder of CQ Construction, building luxury custom homes and developments in Silicon Valley. Links: 🔗 DaveRossiGlobal.com 🔗 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 This Builder Shut Down a $35M Company w/ Dave Rossi

  3. 5d ago

    How AI Is Reshaping Real Estate Brokerages w/ Eric Bramlett

    Eric Bramlett wired his Austin brokerage into an AI system that flags exactly where the business is losing money. Eric Bramlett runs Bramlett Partners, the fastest growing independent brokerage in Texas, and he's been investing in Austin real estate since 2003. In this conversation he breaks down how he built an AI system that pulls from his revenue, email, and production data to answer one question, how's the business doing, and what needs attention. He also gets into why most investors overestimate how well they've actually analyzed their last deal, why the 2008 recession forced him to stop chasing side projects, and why he believes the next few years favor small operators over big companies when it comes to adopting AI. Key topics: Building an AI system that audits the brokerage's own dataWhy agentic AI favors small operators over big companies right nowThe reporting systems behind a growing Austin brokerageWhy he only hires the top 20 percent of agentsThe zip code level data showing where Austin opportunity actually is Guest bio: Eric Bramlett is the founder of Bramlett Partners, the fastest growing independent brokerage in Texas, and has been investing in Austin real estate since 2003. Links: 🔗 Learn more about Eric's team: bramlettpartners.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

    How AI Is Reshaping Real Estate Brokerages w/ Eric Bramlett

  4. Jul 19

    Land Flipping Explained: Why It Beats Wholesaling w/ Sumner Healy

    Land flipping returns up to $30 for every $1 in marketing, with almost none of the competition. Sumner Healy spent his first year in real estate chasing ugly houses to wholesale and getting nowhere. Then he mailed a stack of handwritten letters to a rural Nevada county, bought a lot for around $1,000, and flipped it two weeks later. That was the proof of concept. Since then he has closed more than 700 land deals and built Land Insights, the software that now runs his entire operation. In this episode, Sumner makes the case that land flipping is the most efficient active-income model in real estate, and shows how a beginner with a phone can actually start. He breaks down the marketing math that leaves wholesaling behind, how he picks a market before spending a dollar, and how he turns seven figures of land profit into long-term wealth. What you'll learn: Why the marketing return on land beats wholesaling and fix-and-flipHow little money it takes to start, and the deal that proved itMid-market land flipping, and why $25k to $300k is the sturdiest lanePicking a market with sell-through rates and supply tolerancesHow he allocates land profit across index funds, mobile home parks, Section 8, and syndications Guest bio: Sumner Healy is a land investor with 700+ deals and the founder of Land Insights, a market-selection and disposition platform used by roughly 1,000 land investors. He runs a land coaching community and invests across land, rentals, and syndications. Links: 🔗 Build systems for your investing business: https://realdealcrew.com 🔗 Run comps and pick markets (Land Insights): https://landinsights.co/lite 🔗 Join the land community: https://skool.com/lia/about 🔗 Free 7-Day Deal Challenge: https://landinvestor.co/sevendaychallenge 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

    Land Flipping Explained: Why It Beats Wholesaling w/ Sumner Healy

  5. Jul 17

    The Mindset Framework Behind a $2.7 Billion Real Estate Portfolio w/ Trevor McGregor

    Trevor McGregor lost his parents' home on one bad bet. Then he helped a client scale to $2.7B. Trevor McGregor spent over five years coaching for Tony Robbins, has invested in real estate for two decades, and has helped more than 45,000 people work through their business and their portfolios. Before any of that, he lost his family's home on a failed business bet and had to rebuild from nothing. In this episode, Trevor breaks down the mindset framework he now teaches investors, why most people jump straight to strategy and stay stuck, and how one client went from four single family homes to $2.7 billion in assets under management. If you feel capped on income, deals, or momentum, this episode is the mindset work underneath the strategy. Key topics: The 4S framework: state, story, standards, and strategyHow one client scaled from four homes to $2.7B in AUMWhy high performers have a "tax problem" real estate solvesThe three positions every investor sits in: maintenance, growth, or scaleFinding your zone of genius and building the right team around it Guest bio: Trevor McGregor is a high performance master platinum coach who spent over five years coaching for Tony Robbins. He's invested in real estate for two decades and has helped more than 45,000 people navigate their business, real estate, and franchise decisions. His book, Rich Beyond Belief, releases in August. Links: Trevor McGregor: trevormcgregor.com🔗 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

    The Mindset Framework Behind a $2.7 Billion Real Estate Portfolio w/ Trevor McGregor

  6. Jul 15

    DSCR Loans Explained: Skip the Debt-to-Income Ratio w/ Eric Bernstein

    Eric Bernstein of LendFriendMTG.com explains how DSCR loans skip debt-to-income entirely for investors. Real estate investors and self-employed borrowers keep getting denied by conventional lenders, not because they can't afford the house, but because banks don't know how to read income that doesn't show up as a clean W-2. Eric Bernstein, founder of LendFriendMTG.com, joins Jack to break down non-QM and DSCR lending, the two paths built specifically for investors, freelancers, and anyone whose income looks different on paper than it does in their bank account. They cover how DSCR loans underwrite the property instead of the person, why hitting 10 conventional loans forces serious investors into DSCR, how short-term rental income can rescue a deal that fails the 1:1 ratio, and what documents to have organized before you ever apply. Eric closes with a real case study on a SpaceX executive who was denied by four major banks despite a strong income, then approved at 95% loan-to-value through a portfolio loan. Key topics: What non-QM lending is and who it's actually built forHow DSCR loans skip debt-to-income and underwrite the property insteadUsing Airbnb and short-term rental income to fix a failing ratioThe documents to have ready before you applyCase study: a $3.5M denial that became a 95% LTV approval About Eric Bernstein: Eric Bernstein is the founder of LendFriendMTG.com and has spent over 10 years in the mortgage industry, specializing in non-QM, DSCR, and portfolio lending for real estate investors and self-employed borrowers across 16 licensed states. Links: 🔗 Work with Eric: LendFriendMTG.com 🔗 Build systems for your investing business: https://realdealcrew.com #RealEstateInvesting #DSCRLoan #NonQMLending #RealEstateFinancing #MortgageLending #PortfolioLoan #InvestmentProperty #RealDealChat #RealEstateInvestor #PropertyInvesting #CashFlow #BRRRRStrategy 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

    DSCR Loans Explained: Skip the Debt-to-Income Ratio w/ Eric Bernstein

  7. Jul 13

    How a $160K Policy Loan Funded a Fourplex w/ Mark Willis

    A real estate investor borrowed $160K from his life insurance and never stopped compounding. Here's how. CFP Mark Willis returns to break down the Bank On Yourself strategy and how real estate investors are using life insurance cash value as a source of capital without slowing their growth. He walks through a real client who borrowed $160,000 from his policy to fund a fourplex while the policy kept compounding untouched, why he agrees with Dave Ramsey that most whole life insurance is a bad deal, and what makes the 2% version different. The conversation also covers the Vanderbilt and Rockefeller families as a case study in generational wealth, how a policy loan compares to a HELOC, and where AI still falls short as a financial advisor. Key topics: How a policy loan funded a fourplex without losing a dollar of compoundingWhy most whole life insurance is a bad deal, and what the 2% version looks likeVanderbilts vs Rockefellers, why some families keep generational wealth and others lose itPolicy loans versus a HELOC, side by sideWhy AI still can't replace a financial advisor's judgment Guest bio: Mark Willis is a Certified Financial Planner and co-author of The Business Fortress, How to Grow, Protect, and Exit Your Business with Confidence. He specializes in Bank On Yourself and infinite banking strategies for business owners and real estate investors. Links: Learn more from Mark and get free chapters of The Business Fortress at kickstartwithmark.com, mention the book title in the form notes 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 a $160K Policy Loan Funded a Fourplex w/ Mark Willis

  8. Jul 11

    How to Build Infill Housing in California w/ Jared Jones

    Jared Jones went from flipping houses to a nine-figure infill development company in California. Jared Jones runs Middle Housing Partners, where he builds and scales micro-infill housing across California using laws most developers don't fully understand yet, ADUs, SB9, and SB1123, the Starter Home Act. He started in real estate in 2005 doing loans, moved into flipping through the crash, and then in 2020 California's zoning changes opened the door to adding units on existing lots. That shift turned into a nine-figure company with hundreds of infill units in the pipeline. In this conversation, Jared and Jack cover how statewide zoning stripped city-by-city control over housing, why big institutional builders can't touch the small-project opportunity the way independent developers can, and the build-to-rent model that lets Jared pull nearly all his invested cash back out of a project. Jared also gets candid about the mistake that cost him early on, delegating decisions instead of learning the laws himself, and why he believes the affordability crisis is really a crisis of permission. If you've written off California as too expensive or too regulated to invest in, this episode reframes exactly why the opposite might be true right now. Key topics: Micro-infill housing explained: ADUs, SB9, and SB1123How statewide zoning changed California's housing rulesThe build-to-rent model, BRRRR on steroidsWhy vertical integration became necessary at scaleThe delegate-don't-abdicate lessonThe goal of 10,000 units a year Guest bio: Jared Jones is the founder of Middle Housing Partners, a vertically integrated development company building micro-infill housing across California. He is currently finishing his first book, The Middle Housing Revolution. Links: Connect with Jared on LinkedIn: https://www.linkedin.com/in/jared-jones-9a3694168/ Instagram: Middle Housing Partners (middlehousingpartners.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

    How to Build Infill Housing in California w/ Jared Jones
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5
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81 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.

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