Real Estate Investing with RealDealChat

Hosted by RealDealCrew / Jack Hoss

Investing Entrepreneurship EducationInterviews guestsExplicit

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300

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Jun 2026

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About the show

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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June 15, 202631 min

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 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

June 13, 202635 min

Turn Your Insurance Bill Into a Profit Center w/ Nicolas Lares

Nicolas 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

June 11, 202631 min

Your CPA Is Costing You Money (Here's Proof) w/ Peter Holtz

Peter 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

June 9, 202635 min

Stop Using AI Like Google (Do This Instead) w/ Michelle Hamilton

Michelle 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

June 7, 202635 min

Why High Earners Still Live Paycheck to Paycheck w/ Andrew Giancola

Andrew Giancola explains why high earners still live paycheck to paycheck and the exact steps to build wealth the right way as a real estate investor.In this episode of RealDealChat, Jack Hoss sits down with Andrew Giancola of Master Money to break down the financial mistakes even successful investors make and how to fix them before they cost you years of progress.Andrew covers:Why lifestyle inflation is the #1 wealth killer for real estate investorsThe "Big Three" spending categories that destroy financial progress (housing, transportation, food)How to find a real tax strategist (not just someone filling in boxes)The Augusta Rule, cost segregation, and other tax strategies investors overlookThe One-Three-Six emergency fund method and why you need it before you scaleHow to calculate your financial freedom number and reverse engineer your portfolioAvalanche vs snowball method for eliminating consumer debtWhy diversification beyond real estate matters for long-term wealthHow Andrew used AI (including Claude) to build custom software tools in 90 minutes that would have cost $5,000-$10,000AI use cases for real estate investors: property evaluation, tenant management, and deal analysisThis conversation is essential for:Real estate investors who feel busy but not financially freeEntrepreneurs scaling income but not building wealthInvestors who want to clean up their financial foundation before they growIf you've ever made more money and somehow ended up with less, this episode will show you exactly where it's going and how to stop it.🔗 Learn more about Andrew: https://mastermoney.co🔗 Build systems for your investing business: https://realdealcrew.com#RealEstateInvesting #WealthBuilding #PersonalFinance #LifestyleInflation #TaxStrategy #FinancialFreedom #RealDealChat #InvestorMindset #PassiveIncome #AIForBusinessWork 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

June 5, 202636 min

Why 90% of ISA Hires Fail Before They Start w/ Gustavo Munoz Castro

Gus Munoz-Castro reveals why 90% of ISA hires fail — and how real estate investors can use AI to train callers, scale lead gen, and close more deals.Full DescriptionIn this episode of RealDealChat, Jack Hoss sits down with Gustavo Munoz-Castro of Power ISA to break down how real estate investors can build high-performing calling teams, use AI the right way, and stop wasting money on lead gen strategies that don't convert.Gus has been in the ISA and virtual assistant space for over five years and shares what's actually working right now in today's market.Topics covered:Why 90% of ISA success or failure is determined before you ever hire someoneHow AI voice agents are being used to train callers instead of replace themThe 10X coaching efficiency unlock: feedback sessions with 5-10 people in the time it used to take for oneWhy cold calling, mailers, and driving for dollars still work better than everThe real problem with Google Pay Per Click for real estate investorsHow to build a lead gen system before you add any leverageWhat the 45X ROI calling case study looked like in practiceThe "3 motivated sellers a day" rule and why it compoundsHow to script calls: intro and close from memory, bullet points for everything elseWhy genuine curiosity and rapport are the two things you can't train aroundIf you are trying to scale your acquisitions, this episode cuts through the AI hype and gives you a clear framework for building the systems and the team to back it up.🌐 Learn how Power ISA can help your team: https://powerisa.com🔗 Build systems for your investing business: https://realdealcrew.com#RealEstateInvesting #ISA #VirtualAssistants #LeadGeneration #ColdCalling #RealDealChat #AIForBusiness #WholesaleRealEstate #MotivatedSellers #RealEstateInvestorWork 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

June 3, 202643 min

Why Your CPA Is Costing You Money (And Doesn't Know It) w/ Kevin Brunner

Kevin Brunner explains why your CPA may be costing you money, how to cut your effective tax rate, and what most real estate investors get wrong about wealth preservation.In this episode of RealDealChat, Jack Hoss sits down with Kevin Brunner of The Q Companies to talk about what happens to a real estate portfolio when the wrong advisors are in place, and what it looks like to actually protect the wealth you've built.Kevin breaks down:Why CPAs advise investors to "just pay the tax" and how that costs you money every yearHow high-earning investors can stay at a 10% effective federal tax rateThe installment sale trust strategy and how it avoids capital gains on a saleWhy a 1031 exchange alone is not a complete exit strategyHow to reset depreciation through a trust structureWhat "hold till you die, swap till you drop" really means for your portfolioWhy the financial services industry is set up against the investorHow to prepare your heirs to actually manage what you leave themWhy wealth transferred without preparation destroys familiesThe "quadrant" framework for thinking about all your assets, not just financial onesThis episode is for:Real estate investors with significant equity who haven't updated their estate planInvestors approaching a sale or 1031 exchangeAnyone who suspects their advisor isn't giving them the full picturePortfolio holders who haven't thought about succession and heir preparation🔗 Learn more about Kevin and The Q Companies: https://theqcompanies.com🔗 Build systems for your investing business: https://realdealcrew.com#RealEstateInvesting #TaxStrategy #WealthPreservation #EstatePlanning #1031Exchange #PassiveIncome #RealDealChat #InvestorMindset #FinancialAdvisor #TaxEfficiencyWork 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

June 1, 202628 min

Stop Chasing Clients: Build a Brand That Attracts Them w/ Tara Polley

Tara Polley explains how building a personal brand through media stopped the grind and started attracting clients who already trust her.In this episode of RealDealChat, Jack Hoss sits down with Tara Polley of welcomehomesonoma.com, a 25-year real estate veteran turned television host, to break down how media, storytelling, and personal brand building change the game for realtors and investors alike.Tara shares her full framework including:Why getting on camera shortens the sales cycle by building trust before the first conversationHow storytelling and authenticity outperform polished, perfect content every timeThe role AI tools like Claude and ChatGPT play in scripting listings and TV segmentsHow she uses CapCut and TikTok to create social content fast without a big production teamWhy lifestyle marketing sells properties faster than leading with features and square footageThe delegation framework she uses to decide what to keep vs. automate vs. hand offWhat top performers in real estate actually have in common (and it's not talent)Why realtors who stay stuck in 2021 pricing mindsets are losing deals right nowThis episode is for:Realtors ready to stop cold prospecting and start attracting aligned clientsInvestors who want to understand how personal brand impacts deal flowAnyone in real estate who knows they should be creating content but keeps putting it offIf you've ever felt like you were grinding harder than your results showed, this episode is the reset you need.🔗 Check out Tara: https://welcomehomesonoma.com🔗 Build systems for your investing business: https://realdealcrew.com#RealEstateMarketing #PersonalBrand #RealtorLife #RealEstateInvesting #ContentMarketing #RealDealChat #AIForRealEstate #SocialMediaForRealtors #RealEstateBusiness #ClientAttractionWork 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

May 30, 202632 min

This $50 Billion Plan Could Rebuild Detroit w/ Rod Lockwood

Rod Lockwood reveals his $50 billion plan to transform Belle Isle into a tax-free, self-governing city — and what it means for Detroit real estate investors.In this episode of RealDealChat, Jack Hoss sits down with Rod Lockwood, a second-generation Detroit real estate developer and founder of the Belle Isle Freedom City project — a bold proposal to turn a 1,000-acre island in the Detroit River into a privately funded, tax-free, self-governing city of 50,000 people.Rod breaks down:Why Detroit went from the richest city in the world in 1950 to the poorest major city todayThe 99-year lease structure modeled after Hong Kong's revivalHow Belle Isle would operate with no income tax and a land value tax systemWhy 46,000 Detroiters would commute to the island daily, paying full state and federal taxesThe estimated $5 to $6 billion infrastructure investment and $50 billion total build-outHow Detroit land at $7 to $10 per square foot becomes attractive to international entrepreneursThe Formula One racetrack concept and car-free designWhy a commissioned poll showed Detroit residents support the project by a plus 41% marginHow Rod is using AI for cost modeling and document prep across the projectThis episode is for investors watching the Detroit market, anyone interested in special economic zones, and real estate developers thinking about large-scale opportunity and urban policy.🔗 Learn more about the project: https://bellisle-freedomcity.com🔗 Build systems for your investing business: https://realdealcrew.com#RealEstateInvesting #Detroit #SpecialEconomicZone #LandValueTax #FreedCity #UrbanDevelopment #RealDealChat #InvestorMindset #AffordableHousing #RealEstateDevelopmentWork 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

May 28, 202645 min

Why Paying Off Your Mortgage Is Killing Your Wealth w/ Al Zdenek

Al Zdenek explains why paying off your mortgage early could be destroying your long-term wealth and how to reach financial freedom faster by thinking differently.In this episode of RealDealChat, Jack Hoss sits down with Al Zdenek, CPA, wealth advisor, and author of Master Your Cash Flow, to break down the financial decisions most investors and business owners are getting completely wrong.Al went from near-bankruptcy in his 30s with tens of millions in troubled projects, to reaching financial independence at 48. Now he shares the exact framework he used with hundreds of clients to accelerate their path to financial freedom.What you'll learn in this episode:Why paying off your mortgage early can actually leave you broke in retirementThe difference between good debt and bad debt (and why most gurus blur the line)How small financial decisions today compound into massive outcomes over decadesThe right way to negotiate $100K in credit card debt down to near zero interestWhy going into retirement with a paid-off house can be a financial trapHow Al helped a former Fortune 500 president restart his retirement cash flow overnightWhat most financial advisors are missing because they only think short-termWhy cash flow-oriented advising beats goals-based advising every timeHow to know if you could retire 5 to 10 years earlier than you thinkThis episode is essential for:Real estate investors balancing good debt vs. equityBusiness owners approaching retirementAnyone who's been told to pay off debt first and saveInvestors who want to use leverage strategically instead of emotionallyIf you've ever wondered whether you're actually building wealth or just feeling like it, this episode will change how you think.🔗 Learn more from Al: https://alzenek.com🔗 Check out the CakeClub app: https://cakeclubapp.com🔗 Build systems for your investing business: https://realdealcrew.com#RealEstateInvesting #FinancialFreedom #WealthBuilding #CashFlow #GoodDebt #RealDealChat #PersonalFinance #RetirementPlanning #InvestorMindset #DebtStrategy #FinancialIndependence #RealEstatePodcastWork 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