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.
55episodes
Episodes
Newest firstAll episodes
The 3 Silent Budget Killers Destroying Your Flip Profits w/ Kevin Dairaghi
5d ago00:38:27Tap to summarizeKevin Dairaghi built a house flipping operation in St. Louis and reveals the 3 silent budget killers that crush real estate investors before they ever scale.In this episode of RealDealChat, Jack Hoss sits down with Kevin Dairaghi of Restore STL to talk about what really happens when you go from doing a few flips a year to running a real operation.Kevin covers:The 3 biggest silent budget killers investors overlook on every flipWhy doing 10 houses a month almost broke him mentally and financiallyHow personal development drives professional performance in real estateThe 5-step recipe for success he uses with every coaching studentWhy he visits every active property at least once a weekHow to talk to motivated sellers with dignity and close deals people actually needHis framework for building a life roadmap and knowing your 3.0 selfUsing AI and team systems to stop being the bottleneck in your own businessThis episode is a fit for:Fix and flip investors trying to scale without burning outSolopreneurs ready to stop doing everything themselvesInvestors who want to close more deals by leading with serviceAnyone who has scaled volume but hasn't scaled profit🔗 Connect with Kevin: kevindairaghi.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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They're Building Homes with Grass. It Actually Works. w/ Josh Dorfman
1w ago00:35:33Tap to summarizeJosh Dorfman explains how Planted is turning fast-growing grass into structural building panels now used by DR Horton, the largest home builder in America.In this episode of RealDealChat, Jack sits down with Josh Dorfman, CMO of Planted and founder of climate media company Supercool, to break down one of the most unusual innovations hitting the construction supply chain right now.Planted is replacing traditional lumber and oriented strand board with panels engineered from a perennial grass that grows 10x faster than trees, can be harvested one to two times per year, and locks carbon into the walls of homes rather than releasing it into the atmosphere. Their factory sits inside a former American Spirit cigarette plant in Oxford, North Carolina, and their partner is DR Horton — the builder behind one in every seven homes built in America.Topics covered:How Planted went from a SpaceX engineering team to a working construction materialWhy planting trees alone cannot solve the carbon math at scaleThe perennial grass that out-competes timber on cost, supply chain stability, and carbon captureWhy former tobacco farmers in North Carolina are switching to this cropHow tariffs, Canadian wildfires, and Baltic birch disruptions are accelerating demand for domestic alternativesPlanted's long-term stable pricing model and how it beats commodity timber volatilityThe marketing playbook for a disruptive startup in a slow-moving industryWhy brand fragmentation kills startups even when the product is workingAI tools, bottlenecks, and the entrepreneur lie most founders tell themselvesThis one is for builders, real estate investors, developers, and anyone watching material costs eat into project margins.🔗 Learn more about Josh's climate media company: https://getsuper.cool🔗 Build systems for your investing business: https://realdealcrew.com#RealEstateInvesting #HomeBuilding #ConstructionInnovation #SustainableBuilding #Climatetech #SupplyChain #BuildingMaterials #RealDealChat #EntrepreneurMindset #GreenBuildingWork 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 Financial Advisors Avoid Real Estate w/ CJ Davidson
1w ago00:40:57Tap to summarizeCJ Davidson explains why most financial advisors can't help real estate investors — and how Proxy Financial is built to actually bridge that gap.In this episode of RealDealChat, Jack sits down with CJ Davidson, founder of Proxy Financial, to dig into what's broken in the financial advisory industry and why real estate investors are often left without real guidance.CJ shares:Why real estate has to be at the core of every financial plan, not an afterthoughtHow most advisors avoid real estate conversations because they're not equipped to have themThe "art and science" model behind Proxy Financial and what makes it differentHow AI is accelerating what advisors do without replacing the trust that drives long-term relationshipsThe early lessons from building a firm from scratch in a room with no windowsWhy following the wrong people early in your career can set you back yearsWhat it looks like when a 15-year client relationship becomes something bigger than just moneyThis episode is for:Real estate investors who feel ignored by their financial advisorFinancial professionals who want to build something more than a book of businessEntrepreneurs thinking about how to scale by working on the business, not just in itIf you've ever felt like your financial advisor just doesn't get real estate, this one is for you.🔗 Learn more at: https://proxyfinancial.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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Why Billionaires Only Put 20% in the Stock Market w/ Bob Fraser
2w ago00:33:00Tap to summarizeBob Fraser reveals why billionaires keep only 20% in public markets and how private alternatives can protect and grow wealth — without chasing returns.In this episode of RealDealChat, Jack Hoss sits down with Bob Fraser, CFO and chief macro strategist of Aspen Funds and co-author of the USA Today bestseller Invest Like a Billionaire, to break down how the ultra-wealthy structure their portfolios and why most investors are playing the wrong game entirely.Bob covers:Why billionaires keep only 20-30% of their wealth in public marketsThe difference between diversification and true mathematical uncorrelationWhy the S&P 500 index is more concentrated than most investors realizeWhy public markets are driven by emotion and narrative rather than fundamentalsThe current valuation argument against public equities and what history says about forward returnsHow to evaluate private alternative investments by risk profileWhy oil and gas can function as an uncorrelated, cash-flowing assetThe natural gas thesis and its connection to AI energy demandHow the JOBS Act of 2012 opened private investing to accredited investorsRed flags to watch for when vetting syndicators and sponsorsWhy losses hurt compounding more than gains help itBob's personal story of being wiped out twice and what it taught himThis episode is essential for:Accredited investors looking to move beyond a traditional 60/40 portfolioReal estate investors who want to add true uncorrelation to their holdingsAnyone vetting private deals and syndicationsInvestors trying to understand where risk actually lives in their portfolio🔗 Learn more about Bob and Aspen Funds: https://aspenfunds.us🔗 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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Why 11% Beats the S&P 500 (Without the Risk) w/ Jay Patel
2w ago00:41:02Tap to summarizeJay Patel reveals how PropTechs delivers a consistent 11% return backed by real estate collateral — and why it outperforms the S&P 500 without the volatility.In this episode of RealDealChat, Jack sits down with Jay Patel, founder of PropTechs — a real estate investment fund built for passive investors who want consistent, collateralized returns without the headaches of active ownership.Jay breaks down:Why PropTechs is structured to pay investors their 11% before the fund makes a single dollarHow 150% collateral coverage protects capital in any market environmentThe three verticals inside the fund: short-term transactions, long-term holdings, and a 25% cash reserveWhy residential assisted living centers are the best long-term hold in today's marketHow the silver tsunami creates a decade-long tailwind for senior housingWhy sequence of return risk is the most overlooked danger for retireesThe Detroit apartment deal that taught Jay to never invest based on a cap rate aloneHow AI is now handling deal sourcing and property shortlisting inside the fundWhy Jay built India's MLS system and is now expanding it to the PhilippinesThis episode is essential for:Passive investors looking for real estate exposure without active managementPre-retirees protecting capital while still growing itAnyone tired of stock market volatility eating into their retirement account🔗 Learn more about PropTechs: https://proptex.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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Why 90% of Success Has Nothing to Do With Strategy w/ Dr. Noah St. John
2w ago00:36:48Tap to summarizeDr. Noah St. John reveals why 90% of success is your inner game and how head trash is the hidden friction capping your income and business growth.In this episode of RealDealChat, Jack Hoss sits back down with Dr. Noah St. John, bestselling author, performance coach, and creator of the Afformations Method, to dig into what's actually holding investors and entrepreneurs back from their next level.Noah breaks down:Why 90% of success is your inner game, not your strategyWhat "head trash" is and how it creates a revenue ceiling you can't push throughThe difference between inner friction and outer frictionHow he helped a real estate investor go from six figures to multi-million dollar deals after one coaching engagementThe Human AI Gap and why most business owners don't even know it exists yetHow AEO (Answer Engine Optimization) is replacing traditional SEO and why you need to be cited by the LLMsHis new children's book "I Ask Better Questions" and why even adults are buying it for themselvesWhy your business problems are friction problems, not money problemsThis episode is for:Real estate investors stuck at the same income level no matter how hard they pushEntrepreneurs who have tried every strategy but still feel like the brakes are onBusiness owners trying to get ahead of the AI visibility curveIf you've ever wondered why your effort isn't matching your results, this conversation is going to hit.🔗 Learn more about Dr. Noah St. John: https://noahstjohn.com 🔗 Build systems for your investing business: https://realdealcrew.com#RealEstateInvesting #EntrepreneurMindset #InnerGame #HeadTrash #Afformations #PersonalDevelopment #RealDealChat #AIForBusiness #RevenueGrowth #SuccessMindsetWork 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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From $100K to $15M Raised: The Passive Income Blueprint w/ Bronson Hill
2w ago00:32:22Tap to summarizeBronson Hill shares how he went from $100K raised to $15M in 18 months and why single family investing is holding most people back.In this episode of RealDealChat, Jack Hoss sits down with Bronson Hill, author of Fire Yourself and host of The Mailbox Money Show, to dig into what real passive income actually looks like and how to build it through syndication and alternative assets.Bronson covers:Why trading time for money traps even high-earning professionalsHow he went from 4 single family rentals to a 225-unit syndication dealThe difference between a property manager and true passive incomeWhy the effort to close a single family deal is almost identical to a multifamily dealHow one conversation on a cruise launched $15M in capital raisedThe value-first networking approach that beats cold outreach every timePrefabricated housing as a solution to the housing crisis and LA fire rebuildingSenior care as a growing investment categoryA $40M loss lesson from a 2021 Atlanta multifamily dealWhy long-term fixed debt and higher equity are now non-negotiableHow Bronson uses custom GPTs to scale content and investor communicationsThis conversation is essential for:Investors stuck in the single family grind looking to scalePassive investors exploring syndication for the first timeOperators thinking through capital raising and deal structuringAnyone building wealth systems that don't require their daily involvementIf you're still trading your time for income, this episode will reframe everything.🔗 Text CASHFLOW to 33777 for Bronson's top investments of 2026 🔗 Build systems for your investing business: https://realdealcrew.com#RealEstateInvesting #PassiveIncome #Syndication #RealDealChat #MultifamilyInvesting #MailboxMoney #CapitalRaising #InvestorMindset #AlternativeInvesting #FinancialFreedomWork 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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From Immigrant to Real Estate Mogul: Doren Levi's Journey
3w ago00:33:39Tap to summarizeIn this conversation, Doren Levi shares his journey from being an immigrant to becoming a successful real estate developer. He emphasizes the importance of human connection in business, the lessons learned from early ventures, and the significance of betting on oneself. Doren discusses the challenges of partnerships, the power of mindset, and the need to create meaning beyond financial success. He also shares insights into his current projects and future aspirations in the real estate market.TakeawaysDoren Levi is a real estate investor with a unique background.His journey from immigrant to developer was driven by necessity.Human connection is crucial in business, especially in real estate.Surrounding yourself with smarter people is key to success.Partnerships can be challenging and require clear communication.Betting on oneself is essential for achieving significant results.Mindset plays a critical role in overcoming self-doubt.Creating meaning in work is more fulfilling than financial gain.Time is the most valuable asset we have.Doren is currently focused on multifamily development and creative deal structuring.Keywordsreal estate, development, business, partnerships, mindset, success, human connection, multifamily, investment, entrepreneurshipWork 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 Security Deposits Are Costing Landlords More Than They Think w/ Andrew Bowen
3w ago00:31:27Tap to summarizeLease insurance for rental property explained: Andrew Bowen of LeaseLock breaks down how to replace deposits and protect your assets at scale.In this episode of RealDealChat, Jack Hoss sits down with Andrew Bowen, VP at LeaseLock, to break down why the security deposit model is broken and what smart operators are replacing it with.Andrew brings 30 years across rental housing, SaaS, and InsureTech. He's seen both sides of the table and pulls no punches on what most operators are getting wrong.What lease insurance actually is and how it replaces the deposit with a certificate worth 1–3x coverageHow $90k in claims on a 260-unit deal translated to $1.6M in preserved asset value at saleWhy 59% of Americans can't cover a $1,000 emergency, and what that means for your leasing funnelHow underwriting works at the asset level, not the individual tenant levelThe zero deposit marketing advantage and why it fills buildings fasterThe biggest operational gap Andrew sees across rental portfolios nationwideThe cost per lead trap that's quietly killing multifamily marketing ROIWhy most operators think they're unique, but probably aren'tThis episode is for multifamily operators, property managers, and buy-and-hold investors tired of deposit disputes eating into their returns.🔗 Learn more about LeaseLock: https://leaselock.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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What Investors Decide in the First 10 Minutes W/ Scott Kelly
3w ago00:35:08Tap to summarizeScott Kelly has helped companies raise over $5 billion. Here's what investors actually decide in the first 10 minutes of your pitch.In this episode of RealDealChat, Jack Hoss sits down with Scott Kelly, founder of Black Dog Venture Partners, to break down how entrepreneurs and real estate investors can raise capital the right way — without wasting time on the wrong investors.Scott has spent 30 years on both sides of the table, helped companies raise over $5 billion, completed three exits of his own, and built a network of 13,000 investors and 40,000 business partners. He brings the kind of direct, no-fluff perspective you won't get from Shark Tank.What we cover:Why you probably don't need venture capital (and what to do instead)The "traction, traction, traction" framework for getting investors to say yesThe top 3 red flags that instantly kill investor interestWhat the top 10% of pitches have in common — and what the worst ones sayWhy 75% of companies that raise VC still fail within 2–3 yearsHow AI has changed what investors expect before writing a checkWhy Silicon Valley doesn't have a lock on deal flow — and where to look insteadAlternative capital models: grants, debt, and non-dilutive funding most investors overlookHow to structure investor updates to build trust and get more than money from your partnersThe $270,000 lunch story: how a 1-minute pitch from Salt Lake City led to hundreds of millionsThis episode is essential for:Real estate investors raising private capital or looking for equity partnersEntrepreneurs preparing for their first (or next) raiseBusiness owners who want to scale without giving up control🔗 Visit Black Dog Venture Partners: https://blackdogventurepartners.com🔗 Pitch at an upcoming VC Fast Pitch event: https://vstfastpitch.com🔗 Build systems for your investing business: https://realdealcrew.com#RealEstateInvesting #RaisingCapital #VentureCapital #RealDealChat #EntrepreneurMindset #InvestorRelations #StartupFunding #PrivateEquity #BusinessGrowth #PitchDeck #ScalingBusiness #AlternativeFunding #RealEstateInvestor #CapitalRaising #BlackDogVenturePartnersWork 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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