Podcast
Real Estate Investing with RealDealChat
Hosted by RealDealCrew / Jack Hoss · EN
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.
78episodes
Episodes
Newest firstAll episodes
Non-Food Franchising: The Boring Business Playbook for Investors w/ Jon Ostenson
3d ago00:29:47Tap to summarizeMost 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 rolloverJon'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 RealDealCrewIf 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 AssessmentSee how resilient your current operation actually is.→ https://assessment.realdealcrew.comBook a Fit CallIf you want to explore what a fully system-driven deal flow looks like, let’s talk.→ https://realdealcrew.com/bookLIKE • SHARE • JOIN • REVIEWWebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram
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Why Most Investors Quit Too Early w/ Joshua Gould
5d ago00:38:22Tap to summarizeMost 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 RealDealCrewIf 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 AssessmentSee how resilient your current operation actually is.→ https://assessment.realdealcrew.comBook a Fit CallIf you want to explore what a fully system-driven deal flow looks like, let’s talk.→ https://realdealcrew.com/bookLIKE • SHARE • JOIN • REVIEWWebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram
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How to Never Have a Broke Month Again w/ Dan Rochon
1w ago00:45:29Tap to summarizeDan 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 #RealEstateAgentWork With RealDealCrewIf 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 AssessmentSee how resilient your current operation actually is.→ https://assessment.realdealcrew.comBook a Fit CallIf you want to explore what a fully system-driven deal flow looks like, let’s talk.→ https://realdealcrew.com/bookLIKE • SHARE • JOIN • REVIEWWebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram
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How Sober Living Homes Out-Cash-Flow Traditional Rentals w/ Jim Bode
1w ago00:33:31Tap to summarizeOne 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 problemJim 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 AcceleratorLearn more: grouphomeaccelerator.com🔗 Build systems for your investing business: https://realdealcrew.com#SoberLiving #GroupHomeInvesting #RealEstateInvesting #CashFlow #RealDealChat #NicheRealEstate #RealEstatePodcast #PassiveIncome #RecoveryHousing #InvestingStrategyWork With RealDealCrewIf 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 AssessmentSee how resilient your current operation actually is.→ https://assessment.realdealcrew.comBook a Fit CallIf you want to explore what a fully system-driven deal flow looks like, let’s talk.→ https://realdealcrew.com/bookLIKE • SHARE • JOIN • REVIEWWebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram
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How One Insurance Waiver Saved a Client $14 Million w/ Guffy Wright
2w ago00:33:31Tap to summarizeGuffy 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 insuranceGuest 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.comConnect with Guffy Wright on LinkedIn https://www.linkedin.com/in/guffy-wright-752679b/Work With RealDealCrewIf 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 AssessmentSee how resilient your current operation actually is.→ https://assessment.realdealcrew.comBook a Fit CallIf you want to explore what a fully system-driven deal flow looks like, let’s talk.→ https://realdealcrew.com/bookLIKE • SHARE • JOIN • REVIEWWebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram
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How $300K Buys Permanent Residency in Panama w/ Steve Luther
2w ago00:27:36Tap to summarizeA $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 closingGuest 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.comWork With RealDealCrewIf 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 AssessmentSee how resilient your current operation actually is.→ https://assessment.realdealcrew.comBook a Fit CallIf you want to explore what a fully system-driven deal flow looks like, let’s talk.→ https://realdealcrew.com/bookLIKE • SHARE • JOIN • REVIEWWebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram
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Build-to-Rent Investing: From Blackstone to Boutique Firms w/ August Biniaz
2w ago00:31:48Tap to summarizeWall 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 nextAugust 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.comWork With RealDealCrewIf 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 AssessmentSee how resilient your current operation actually is.→ https://assessment.realdealcrew.comBook a Fit CallIf you want to explore what a fully system-driven deal flow looks like, let’s talk.→ https://realdealcrew.com/bookLIKE • SHARE • JOIN • REVIEWWebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram
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Turn Your Insurance Bill Into a Profit Center w/ Nicolas Lares
2w ago00:35:12Tap to summarizeNicolas Lares explains how real estate investors can turn insurance costs into profits using captive insurance — a strategy Fortune 500 companies have used for decades.In this episode of RealDealChat, Jack Hoss sits down with Nicolas Lares, founder of InsurTech, to break down captive insurance — what it is, how it works for real estate investors, and why most investors have never heard of it until now.Nicolas built his career helping run one of Amazon's largest logistics insurance networks before founding InsurTech, where he now helps real estate investors co-own the very insurance company that covers their portfolio.Topics covered include:What captive insurance is and how it differs from traditional insuranceHow investors collectively pool premiums and recapture unused profits at year-endWhy REITs and institutional funds have used this model for decadesHow a single-property investor can get started (yes, even one townhouse)The 80-unit Georgia example where an owner ended the year with a net surplus of $1,500 instead of an insurance expenseHow renters insurance can be stacked into the captive to offset property-level costsWhat traditional brokers say against captives (and why their incentives are misaligned)How InsurTech insures over 1 million doors across the USHow Nicholas is using Claude Code to automate proposal and compliance workflowsRapid fire: the lie investors tell themselves about assumptions and underwritingIf insurance feels like a sunk cost in your portfolio, this episode will change how you look at it.🔗 Visit Nicolas at: https://isur3tech.com🔗 Build systems for your investing business: https://realdealcrew.com#RealEstateInvesting #CaptiveInsurance #LandlordInsurance #PropertyManagement #RealDealChat #PassiveIncome #MultifamilyInvesting #InsuranceCosts #InvestorMindset #RealEstateTips #AIForBusiness #PortfolioGrowthWork With RealDealCrewIf 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 AssessmentSee how resilient your current operation actually is.→ https://assessment.realdealcrew.comBook a Fit CallIf you want to explore what a fully system-driven deal flow looks like, let’s talk.→ https://realdealcrew.com/bookLIKE • SHARE • JOIN • REVIEWWebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram
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Your CPA Is Costing You Money (Here's Proof) w/ Peter Holtz
3w ago00:31:11Tap to summarizePeter Holtz reveals why most CPAs are compliance fillers, not tax planners — and how real estate investors can cut their tax bill by 40% or more.In this episode of RealDealChat, Jack Hoss sits down with Peter Holtz, certified tax planner and CPA, to break down the massive gap between tax compliance and real estate tax planning strategy.Peter covers:Why only 1,100 out of 1.2 million licensed tax preparers are certified tax plannersHow cost segregation works and why virtually no one uses itThe 1031 exchange and reverse 1031 you should know before every saleHow a retired real estate investor legally captured $250,000 in tax-free gains every two yearsThe airline pilot case study: how Peter fought the IRS and won, getting his client years of zero tax liabilityWhy your CPA saying "no, you can't" is a red flagHow to use real estate depreciation to shelter business incomeThe McDonald's model and why every successful business is really a real estate businessHow Peter's team uses AI and cloud accounting to deliver faster resultsQuestions you should ask your CPA before you file another returnIf you own real estate, run a business, or are paying more taxes than you think you should, this episode is required listening.🔗 Learn more at: https://go.peterholtzcpa.com/realdealchat🔗 Build systems for your investing business: https://realdealcrew.com#RealEstateInvesting #TaxPlanning #CostSegregation #1031Exchange #RealDealChat #SmallBusinessTax #TaxStrategy #CPA #RealEstateTax #PassiveIncome #WealthBuilding #TaxFreeIncomeWork With RealDealCrewIf 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 AssessmentSee how resilient your current operation actually is.→ https://assessment.realdealcrew.comBook a Fit CallIf you want to explore what a fully system-driven deal flow looks like, let’s talk.→ https://realdealcrew.com/bookLIKE • SHARE • JOIN • REVIEWWebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram
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Stop Using AI Like Google (Do This Instead) w/ Michelle Hamilton
3w ago00:35:58Tap to summarizeMichelle Hamilton reveals how real estate investors are underusing AI and the exact strategies to automate intelligence, decisions, and deal flow.In this episode of RealDealChat, Jack Hoss sits down with Michelle Hamilton, global AI adoption leader at Answer Rocket, to break down what separates investors who are actually winning with AI from those just typing questions into a chat window.Michelle brings 30 years of commercial real estate experience to her current role leading enterprise AI adoption and change management. She makes the case that AI underperformance is a people problem, not a technology problem.What we cover:Why most investors use AI like a "hyper-Google" and how to stopHuman-first AI adoption and what bottom-up strategy actually meansHow large property management firms are onboarding resistant employeesAgentic AI that logs in as you and pulls competitive deal intelligence overnightUsing AI to build predictive dashboards from your existing dataThe "smart intern" framework for prompting AI to analyze investment documentsHow to use multiple AI models to fact-check each otherBuilding a synthetic board of directors using voice modeChatGPT vs. Gemini vs. Claude: what each model is actually best atMeta-prompting: asking the model to teach you how to use itWhy the $20/month paid upgrade is worth it and which model to start withHow Michelle's AI chief of staff (George) runs her entire morningThis episode is for:Real estate investors and syndicators who know they should be using AI but don't know where to startOperators and business owners sitting on untapped dataAnyone who has tried AI tools and walked away frustratedIf you're ready to go from basic chatbot use to building actual systems around AI, this is the episode.🔗 Connect with Michelle on LinkedIn: Michelle-Hamilton-AI🔗 Build systems for your investing business: https://realdealcrew.com#RealEstateInvesting #AIForBusiness #RealDealChat #MultifamilyInvesting #AIAdoption #RealEstateInvestor #ChatGPT #InvestorMindset #BusinessAutomation #PropTech #AIStrategy #ShortsWork With RealDealCrewIf 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 AssessmentSee how resilient your current operation actually is.→ https://assessment.realdealcrew.comBook a Fit CallIf you want to explore what a fully system-driven deal flow looks like, let’s talk.→ https://realdealcrew.com/bookLIKE • SHARE • JOIN • REVIEWWebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram
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