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. Wyoming LLCs and Asset Protection Trusts for Real Estate Investors w/ Mark Pierce

    1d ago

    Wyoming LLCs and Asset Protection Trusts for Real Estate Investors w/ Mark Pierce

    Mark Pierce has 45 years in asset protection law. Here's how Wyoming LLCs and trusts protect your portfolio. Mark Pierce is a Wyoming trust attorney, former bankruptcy trustee, and 45-year veteran of tax and asset protection law. He's seen every way a real estate portfolio can unravel -- from creditor judgments to family divorces -- and built the legal structures designed to stop it. In this episode, Jack and Mark break down how Wyoming LLCs and asset protection trusts actually work for investors, why the threats inside your own family are usually more dangerous than any outside creditor, and what to do first if you have equity and no protection in place yet. Key topics covered: How the LLC plus trust "double envelope" shelters your cash flows from property judgmentsWhat a charging order is and why Wyoming makes creditors want to negotiate rather than litigateSeries LLCs explained simply and why they're built for real estate investors with multiple propertiesWhy a properly structured asset protection trust is the most effective prenuptial agreement you'll never have to argue about in courtThe two things that destroy LLC protection (commingling and bad bookkeeping) and how Wyoming handles them differentlyWhy proactive planning gives you every tool available and reactive planning gives you almost none Mark Pierce: wyomingtrustattorney.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

    29 min
  2. Non-Food Franchising: The Boring Business Playbook for Investors w/ Jon Ostenson

    3d ago

    Non-Food Franchising: The Boring Business Playbook for Investors w/ Jon Ostenson

    Most investors overlook franchising. Jon Ostenson shows how boring, unglamorous businesses can become your most reliable cash-flowing asset. Jon Ostenson is a multi-brand franchisee, former franchisor, and founder of FranBridge Consulting. He's placed several hundred investors into franchise businesses across the country and has spent a decade helping people find opportunities in industries most people never think to look. In this episode, Jon breaks down why real estate investors are quietly becoming franchise owners, how to evaluate a franchise the same way you'd underwrite any other asset, and why the unglamorous, fragmented industries most people ignore are where the smart money is actually moving right now. What you'll learn: Why 90% of Jon's clients end up in an industry they never had on their radarThe red flags to watch for in a franchise's leadership team before you sign anythingHow the executive model lets you own a franchise without operating it day to dayFranchise stacking as a portfolio-building strategy for investorsWhy those top 100 franchise lists are pay-to-play and what to do insteadHow to fund a franchise using SBA loans or a ROBS retirement rollover Jon's free book, Non-Food Franchising, is available at FranBridgeConsulting.com -- enter your email and they'll send you a download link at no cost. 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
  3. Why Most Investors Quit Too Early w/ Joshua Gould

    5d ago

    Why Most Investors Quit Too Early w/ Joshua Gould

    Most investors blame bad timing or lack of capital. Joshua Gould says the real reason they fail is simpler: they quit too early. Joshua Gould bootstrapped a language services company from nothing, funded it by selling real estate, and scaled it to serve governments, courts, and hospitals across more than 50 countries before selling to private equity in 2021. Now he invests in commercial warehousing in Miami and applies the same frameworks to real estate that he used to build and exit a global company. In this episode you will learn: Why most businesses and investments fail not because the idea was bad, but because the operator quit before the roots were deep enough to holdWhat opportunity cost really means and why most investors never calculate the true numberHow Joshua's father's biggest regret -- selling real estate to fund the business -- shaped how he holds assets todayHow to use AI to build a pro forma, stress test a deal, and pressure-check an offering document before you commit capitalWhy the data never lies, but the story built around it usually doesThe three types of people every investor network needs: connectors, gatekeepers, and expertsThe one question to ask before investing in any fund: why aren't they going to the bank? Joshua runs TheBigWord.com, a language services platform operating across 50+ countries. Find his mentoring content on YouTube at ExecCraft. 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

    38 min
  4. How to Never Have a Broke Month Again w/ Dan Rochon

    Jun 23

    How to Never Have a Broke Month Again w/ Dan Rochon

    Dan Rochon hasn't had a broke month since 2008. He stopped selling and started teaching instead. Dan Rochon is a sales coach, author of "Teach to Sell," and host of the No Broke Months podcast with over 1,200 episodes. He built and sold a 150-agent real estate brokerage and has worked directly with investors on lead generation and seller acquisition. His entire system is built around one idea: the salesperson who teaches wins the trust, and the deal follows. In this episode, Dan breaks down the exact framework he uses to close 85% of his appointments before he ever asks for the deal, and how real estate investors can use the same approach with distressed homeowners. What you'll learn: The four pillars of consistent and predictable incomeThe CPI communication model: rapport, adept questions, and active listeningWhy emotion drives the decision and logic only justifies it after the factHow to handle a seller who is angry, grieving, or shutting you outThe one phone call move that makes you one-of-one versus every other investor 📘 Dan's book: teachtosellbook.com 🔗 Build systems for your investing business: https://realdealcrew.com #RealEstateInvesting #RealEstateSales #TeachToSell #MotivatedSellers #SalesTips #DanRochon #RealDealChat #WholesalingRealEstate #SalesTraining #ConsistentIncome #InvestorMindset #RealEstateAgent 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
  5. How Sober Living Homes Out-Cash-Flow Traditional Rentals w/ Jim Bode

    Jun 21

    How Sober Living Homes Out-Cash-Flow Traditional Rentals w/ Jim Bode

    One sober living home can out-cash-flow five traditional rentals. Jim Bode breaks down exactly how. Jim Bode has been a real estate investor for 25 years. When COVID hit and tenants stopped paying, he discovered sober living homes and built a six-figure operation running three properties in 10 to 15 hours a week. Today he coaches investors and operators through Group Home Accelerator on how to do the same. In this episode, Jim walks through the full model from start to finish: Why renting beds instead of bedrooms changes the cash flow math entirelyThe four-bedroom minimum buy box and the two-beds-per-room ruleHow state and federal funding covers 2 to 6 months of rent per residentADA protections that shield sober living operators from zoning pushbackHow to find the right operator if you want the cash flow without running the homes yourselfWhy turnover is a feature of this model, not a problem Jim also shares the story of a resident who came in missing his front teeth and left two years later with a new smile, a truck, and a drive back home to the family he hadn't seen since he was 14. Guest: Jim Bode, founder of Group Home Accelerator Learn more: grouphomeaccelerator.com 🔗 Build systems for your investing business: https://realdealcrew.com #SoberLiving #GroupHomeInvesting #RealEstateInvesting #CashFlow #RealDealChat #NicheRealEstate #RealEstatePodcast #PassiveIncome #RecoveryHousing #InvestingStrategy 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

    34 min
  6. How One Insurance Waiver Saved a Client $14 Million w/ Guffy Wright

    Jun 19

    How One Insurance Waiver Saved a Client $14 Million w/ Guffy Wright

    Guffy Wright explains how one lender waiver saved a client $14 million in value on a multifamily portfolio. Guffy Wright has spent 18 years placing commercial real estate insurance and now leads a team approaching $150 million in annual premiums at the Mahoney Group, up from $40 million in 2019. In this conversation, he breaks down how insurance stops being a line-item expense and becomes part of an investor's equity strategy. Guffy walks through a lender waiver process that recovered $830,000 in premium savings, equal to $14 million in value at a 6% cap rate, and explains why staying with the same broker for years without shopping it is a "silent killer" most investors never notice. He covers the coverages lenders require that you don't actually need, why master policies are back in 2026, when a loss limit strategy makes sense, and the one renewal habit (putting every policy on the same date) that fixes most broker relationships. He also shares where AI is already changing insurance, and where it still falls short. This episode is for any multifamily or commercial real estate investor who has never questioned their insurance broker relationship. Key topicsThe $14 million lender waiver storyWhy the same broker for years is a "silent killer"Master policies vs. loss limits in 2026The one renewal habit that fixes broker relationshipsWhere AI is already changing insurance Guest bioGuffy Wright leads the real estate insurance practice at the Mahoney Group, where he has grown the book from $40 million to nearly $150 million in annual premiums. Links🔗 Build systems for your investing business: https://realdealcrew.com Connect with Guffy Wright on LinkedIn https://www.linkedin.com/in/guffy-wright-752679b/ 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

    34 min
  7. How $300K Buys Permanent Residency in Panama w/ Steve Luther

    Jun 17

    How $300K Buys Permanent Residency in Panama w/ Steve Luther

    A $300,000 real estate purchase in Panama can get you permanent residency and a second passport. Steve Luther runs Cord Real Estate, a boutique firm based in Nashville that helps American investors buy property abroad. After a serious health crisis, Steve and his wife stumbled into Panama while looking for a Caribbean property with better healthcare access, and ended up buying two investment properties there themselves. In this episode, Steve breaks down why Panama has quietly become one of the strongest hedges against US market volatility for real estate investors: a currency pegged one to one with the US dollar, low property taxes and insurance thanks to its location below the hurricane belt, and a residency by investment program that turns a $300,000 real estate purchase into permanent residency, with full citizenship available after five years. Steve also walks through what that money actually buys on the ground, how financing works for Americans buying through Panamanian banks, and what tends to derail a transaction. If you've ever wondered what buying property abroad actually involves, beyond the highlight reel, this episode lays it out. Key TopicsHow Panama's golden visa program works, and what a $300,000 purchase actually gets youThe retirement (Pensionado) program and its travel, dining, and entertainment discountsWhy the dollar peg and hurricane-free location keep currency and insurance risk lowHow an American gets a mortgage through a Panamanian bankWhat typically derails a Panama real estate transaction, and how it compares to a US closing Guest BioSteve Luther has been in real estate for 24 years and runs Cord Real Estate, a Nashville-based firm that has helped clients invest in residential, commercial, and international property for the past decade, including direct experience buying and managing property in Panama himself. Links🔗 Learn more about Steve's team and the upcoming Invest Panama Summit (May 28 to June 1): CordRealEstate.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

    28 min
  8. Build-to-Rent Investing: From Blackstone to Boutique Firms w/ August Biniaz

    Jun 15

    Build-to-Rent Investing: From Blackstone to Boutique Firms w/ August Biniaz

    Wall Street built entire neighborhoods just to rent them. August Biniaz breaks down how and why it works. August Biniaz, Chief Investment Officer at CPI Capital, returns to break down build-to-rent (BTR): how the asset class started after the 2008 crash, why institutions like Blackstone pivoted from buying scattered homes to building purpose-built rental communities, and what that means for individual investors today. August also pulls back the curtain on how CPI Capital operates at scale, including the AI tool that cut their deal-screening time by 90 percent, and shares his read on where interest rates and the broader economy are headed going into the rest of 2026. Key topics covered: How Blackstone's Invitation Homes buying spree of 75,000 homes gave birth to BTRWhat life inside a BTR community actually looks like (HOA, amenities, maintenance)Why BTR attracts "tenants by choice" and produces lower turnover than traditional apartmentsHow CPI Capital uses Slack, Asana, HubSpot, and AI to run a private equity real estate firmThe 10-year treasury, the war in Iran, and what August thinks happens to rates next August Biniaz is the Chief Investment Officer of CPI Capital, a private equity real estate firm focused on US multifamily and build-to-rent assets with investors in both Canada and the United States. Learn more at https://cpicapital.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

    32 min
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5
out of 5
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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