Real Estate Investing with RealDealCrew

Hosted by RealDealCrew / Jack Hoss

Investing Entrepreneurship EducationInterviews guestsExplicit

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300

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Aug 2026

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About the show

Real Estate Investing with RealDealCrew 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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60 recent

August 20, 202639 min

Losing $4M and Rebuilding to $120M w/ Matthew Teifke

Matthew Teifke lost $4 million on one bad bet, then rebuilt to a $120 million real estate portfolio. Summary: Matthew Teifke started buying real estate at 18, built a property management company managing 780 single family homes with his wife, and has scaled to over $120 million in assets across single family, multifamily, and commercial. On this episode, Matthew opens up about losing $4 million on a bad bet outside real estate, what that loss taught him about forcing deals into existence, and how to spot a bad business partner before you ever sign an agreement. He also breaks down renegotiating a $26 million, 294-unit Austin apartment deal directly with the bank at 3.5% interest, and why he scaled his property management portfolio back down from 780 doors to 120. Key topics: The $4 million loss that reshaped how Matthew invests Why "one deal can change your life" is a lie most investors believe Scaling from 100 doors to 780 doors, and why he scaled back down How to spot a bad partner before you sign anything Renegotiating a $26 million Austin apartment deal at 3.5% interest Guest bio: Matthew Teifke is a real estate investor and broker based in Austin, Texas, with over $120 million in assets across single family, multifamily, and commercial real estate. Links: Follow Matthew on LinkedIn https://www.linkedin.com/in/matthew-teifke-90672438/ 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 Website Apple Podcasts YouTube YouTube Music Spotify Amazon Music Facebook Twitter Instagram

August 18, 202630 min

How Half of Real Estate Brokers Could Disappear w/ Rod Santomassimo

Rod Santomassimo says half of commercial brokers could vanish in 5 years, and he's already using AI to prove it. Rod Santomassimo is the founder of the Massimo Group and a five time bestselling author. His newest book, Selling Buildings, was co written with Bob Knakal, the most prolific commercial building broker in US history. In this conversation, Rod and Jack cover both sides of a sale: what investors are quietly leaving on the table when they sell, and how fast AI is reshaping who does the work of brokerage itself. Rod walks through the "vanity play versus sanity play" test for pricing, the pro forma red flags he sees investors miss, and why he believes roughly half of the 100,000 commercial real estate brokers in the US could be replaced by AI within five years. He also gets specific about the tools he uses daily, including how Claude now compresses days of underwriting work into minutes. Key topics: Why Rod says half of commercial brokers could be gone within five years The vanity play vs sanity play test for pricing a sale The most common mistake investors make before listing a property Why a fully competitive bid process matters even with an offer in hand How Rod uses Claude and Anthropic to speed up underwriting The story behind a building fire the day before closing, and what it taught Bob Knakal about buyer motivation Guest bio: Rod Santomassimo is the founder of the Massimo Group, a coaching and training firm for commercial real estate brokers, and the author of five books including the new release Selling Buildings, co written with Bob Knakal. #️⃣ Hashtags #RealEstateInvesting #CommercialRealEstate #AIinRealEstate #RealDealChat #CommercialBrokers #ClaudeAI #RealEstateBrokers #InvestingTips #PropertyInvesting #RealEstateTech #SellingBuildings #AITools Links: Learn more about Rod at massimo.coach 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 Website Apple Podcasts YouTube YouTube Music Spotify Amazon Music Facebook Twitter Instagram

August 16, 202632 min

Why Passive Real Estate Investing Doesn't Exist w/ John McNellis

Developer John McNellis says passive real estate investing doesn't exist, and he explains why. Summary: John McNellis has developed close to 100 properties over more than 45 years, shifting from a corporate lawyer to a shopping center developer to, today, a specialist in small quick-serve restaurant ground leases with tenants like Chick-fil-A. In this conversation he walks through the two mistakes that wipe out most beginning developers, the deal that nearly cost him everything, and why he thinks the phrase "passive real estate investment" is one of the biggest lies in the business. He also breaks down why commercial real estate is a weaker inflation hedge than most investors assume, and lays out a simple path for landing a first deal. Key topics: The two mistakes that wipe out beginning developers: overpaying and overleveraging Why commercial real estate underperforms as an inflation hedge (3% inflation versus 1.37% appreciation) The shift from ground-up shopping centers to small Chick-fil-A ground leases Why "passive real estate investing" is a myth, and what daily ownership actually requires The get rich slow approach: less debt, more equity, patience over scale About John McNellis: John McNellis is a real estate developer and the author of Making It in Real Estate: Thriving as a Developer , now in its third edition. He has led close to 100 development deals across Northern California over more than 45 years. Links: 🔗 Making It in Real Estate: Thriving as a Developer https://amzn.to/4i8SFgb 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 Website Apple Podcasts YouTube YouTube Music Spotify Amazon Music Facebook Twitter Instagram

August 14, 202633 min

Why 18 Million Americans May Never Own a Home w/ Neal Bawa

The mortgage-to-rent gap just hit a level we've never seen, and it's created a permanent renter class. Neal Bawa returns to RealDealChat for a round two conversation on where the housing market is really headed in 2026. He breaks down why the gap between the median mortgage payment and median rent has never been wider, not even during the 2006 bubble, and why that gap has split the country into two permanent housing classes: an 18-million-family renter nation and 30 million homeowners locked into mortgages they can't afford to give up. Neal also shares his 12-month home price forecast, where he's placing capital in multifamily right now, why the "housing crisis" number keeps shrinking, and how AI has become central to how his company operates. Why the rent vs mortgage gap has never been this wide Why 18 million families are now permanent renters Neal's 12-month home price forecast, and the one market that's the exception Where he's investing now in multifamily, and why he's stepped back from build-to-rent Inside his company's 4-phase AI transformation, including building custom apps with no code Guest bio: Neal Bawa is a multifamily investing expert and the founder of MultifamilyU and Grocapitus, known for a data-driven approach to market analysis and forecasting. Links: 🔗 Learn more from Neal: multifamilyu.com/club 🔗 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 Website Apple Podcasts YouTube YouTube Music Spotify Amazon Music Facebook Twitter Instagram

August 12, 202640 min

The $1M Insurance Mistake Real Estate Investors Miss w/ Kristen Nunnery

One buried line in a certificate of insurance turned two claims into million dollar problems. Kristen Nunnery has spent sixteen years in insurance, risk management, and compliance, and she's the founder of Illumend AI, a platform built to catch hidden risk in third party insurance before it becomes a lawsuit. Most real estate investors and property managers assume that if a vendor or tenant is "licensed and insured," they're covered if something goes wrong. Kristen breaks down why that assumption is often false, walking through a real client story where two separate claims each topped a million dollars because of language buried in a certificate of insurance. She also explains why risk has historically acted as the brake pedal on real estate operations, and how AI is starting to flip that, turning a slow manual process into something that actually speeds deals up instead of stalling them. If you manage property or work with contractors, vendors, or tenants, this conversation will change how you look at the paperwork you've been treating as a formality. Key topics: Why "licensed and insured" doesn't mean what most property managers think The additional insured endorsement, and how it quietly caused two million dollar claims Why real estate and insurance lag behind other industries on adopting new tech How AI is turning insurance compliance from a bottleneck into a competitive edge Balancing AI automation with real accountability in a regulated industry Guest bio: Kristen Nunnery is the founder of Illumend AI, a native AI platform built to simplify insurance compliance for real estate owners, operators, and property managers. She has sixteen years of experience in insurance, risk management, and compliance. Links: Learn more about Kristen's work at illumend.ai 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 Website Apple Podcasts YouTube YouTube Music Spotify Amazon Music Facebook Twitter Instagram

August 10, 202638 min

Manufactured Housing Investing w/ Nathan Jameson of Arx Capital

Nathan Jameson explains why manufactured housing is America's most under-built asset class. Jack sits down with Nathan Jameson, founder of Arx Capital, to unpack why manufactured housing, RV parks, and self storage have become some of the most durable, under-built asset classes in real estate, even as the residents who need this housing most often get the worst financing available to them. Nathan explains how Arx buys existing mobile home communities, removes obsolete homes, brings in new ones, and repositions neglected properties for the long term. He also breaks down the operational mistakes he sees institutional buyers make again and again when they underestimate what it actually takes to fill a lot and sell a home, and why a mom and pop owner keeping rent too low can slowly bleed their own community into disrepair. Along the way, Nathan shares how adopting EOS (the Entrepreneurial Operating System) helped him step out of day to day operations, and tells the story of turning a Pittsburgh property with 35 abandoned homes into an institutional-grade community. Key topics: Why manufactured housing is one of the least subsidized, most under-built affordable housing categories in the country How a borrower with a 750 credit score still ends up paying 9 to 10% on a manufactured home loan The operational mistakes institutional buyers make when they don't understand how to fill and sell manufactured homes Why rent set too low can quietly destroy a mom and pop community over time How EOS helped Nathan remove himself as the bottleneck in his own business Guest bio: Nathan Jameson is the founder of Arx Capital, where he and his team manage close to $200 million in assets across manufactured housing, RV parks, and self storage in the Northeast, Mid-Atlantic, and now the Midwest. Links: 🔗 Build systems for your investing business: https://realdealcrew.com Learn more about Nathan and Arx Capital: arxventures.com #RealEstateInvesting #ManufacturedHousing #MobileHomeParks #AffordableHousing #RealDealChat #PassiveIncome #RealEstateSyndication #ValueAddRealEstate #AlternativeInvesting #RealEstateEducation #WealthBuilding #RVParks #SelfStorage #HousingCrisis 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 Website Apple Podcasts YouTube YouTube Music Spotify Amazon Music Facebook Twitter Instagram

August 8, 202645 min

Why Most Investors Stall at $5K w/ Sean Tepper (Tykr)

Tykr founder Sean Tepper on why most investor accounts stall at $5K, and the system that gets people past it. Sean Tepper is the founder of Tykr, a tool that turns stock picking into a simple green, gray, or red signal. Jack and Sean dig into why the average brokerage account sits around $5,000 while the average Tykr account is over $120,000, and why Sean is convinced the real gap is confidence, not intelligence or luck. They also cover the 4M framework for evaluating a stock, how Tykr avoided the GameStop and AMC meme stock traps, and what it actually took to turn a personal Excel spreadsheet into a real SaaS company with paying customers. Key topics: The traffic light system that removes guesswork from picking a stock The 4M framework: math, meaning, moat, and management Why confidence, not returns, is the real driver of investor behavior The free equation you can run in Excel without any tool at all What broke first when a personal spreadsheet became a company About Sean Tepper: Sean is the founder of Tykr, a stock analysis platform built on a simple scoring system that helps everyday investors decide when a stock is on sale, fairly priced, or overpriced. He's been investing since 2010 and built Tykr's underlying framework by testing it with his own money for years before turning it into software. Links: 🔗 Learn more about Tykr: https://tykr.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 Website Apple Podcasts YouTube YouTube Music Spotify Amazon Music Facebook Twitter Instagram

August 6, 202630 min

Self Storage Investing at Scale w/ Ryan Gibson of Spartan Investment Group

A storage unit rent hike turned airline pilot Ryan Gibson into a 90-property self storage operator. Ryan Gibson spent 20 years flying for the airlines before a frustrating experience as a storage unit renter sent him down a different path. Today he co-runs Spartan Investment Group, a 90-property, 7.5 million square foot self storage portfolio spread across 15 states, making it the 29th largest operator in the country. In this conversation, Ryan and Jack dig into why storage demand holds up in good times and bad, why Ryan refuses to leverage past 55% on a deal even when the market rewards more aggressive operators, and the due diligence and hiring systems that let a former pilot scale a 200-person company. Key topics: The rent hike that pushed Ryan into self storage investing The four Ds that make storage demand recession resistant Why he caps leverage at 50-55% instead of chasing "no money down" deals The 700-point due diligence checklist his team runs on every property Hiring advice: why he'd never hire another entrepreneur Using AI to automate investor reporting across 55+ assets Guest bio: Ryan Gibson is a co-founder at Spartan Investment Group and host of the Passive Income Pilots podcast, where he helps fellow airline pilots learn passive real estate investing. Links: Free training and resources: spartan-investor.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 Website Apple Podcasts YouTube YouTube Music Spotify Amazon Music Facebook Twitter Instagram

August 4, 202643 min

How to Buy Real Estate Big Funds Won't Touch w/ Nasir Ali

A 45-year mobile home park operator on why institutional funds won't touch his deal size, and why that's the edge. Summary: Ali Vahdat is an eighth-generation commercial real estate operator who has spent over 45 years buying, operating, and now exiting mobile home parks and manufactured housing communities, almost entirely across California. In this conversation, Ali explains the exact deal size where institutional capital stops looking and smaller operators can't scale, why the old rule that you have to start in residential before commercial doesn't hold up, and how a vertically integrated dealer arm turns vacant lots into a second profit center. He also walks through a live case study, a distressed 30-unit acquisition in Northern California, and a resident-ownership exit strategy he's testing that sells the land under the homes, not just the homes themselves. Key topics: Why big funds ignore the $5M to $25M deal range and how that becomes an advantage The myth that you must start in residential before moving to commercial How a vertically integrated dealer arm creates a second profit center A live case study on a distressed 30-unit acquisition and its exit plan The "smell test" most operators skip before buying Why buying right, not selling right, decides 90 percent of the outcome About the guest: Ali Vahdat is an eighth-generation commercial real estate operator with over 45 years of experience in mobile home parks and manufactured housing communities, currently running a fund through Rise360 Ventures. Links: 🔗 Learn more about Ali's team: https://rise360ventures.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 Website Apple Podcasts YouTube YouTube Music Spotify Amazon Music Facebook Twitter Instagram

August 2, 202631 min

How Investors Qualify for Loans Without Tax Returns w/ Dante Royster

A 20-year mortgage lender explains how investors can qualify for loans using rental income alone, no tax returns required. Dante Royster has spent over two decades in mortgage lending, the last several years focused specifically on real estate investors. In this episode, he breaks down what changed in lending after interest rates doubled in late 2022, why roughly one in four transactions today are investor deals, and how DSCR loans let investors qualify off rental income alone. He also shares the honest answer to what lie most investors tell themselves about having a real strategy. Key topics: How DSCR loans qualify investors off rental income, no tax returns or pay stubs Why the Q4 2022 rate doubling permanently reshaped investor financing Why one in four real estate transactions are now investors How Dante uses AI tools like Claude to move faster in his own business The lie most investors tell themselves about having a strategy Guest bio: Dante Royster is a mortgage lending veteran of over 20 years, now focused on real estate investor financing. He is the author of Ultimate Mortgage Guide and runs the YouTube channel Epic Spotlight. Links: 🔗 Build systems for your investing business: https://realdealcrew.com 📘 Ultimate Mortgage Guide, available on Amazon 📺 Epic Spotlight on YouTube #RealEstateInvesting #DSCRLoan #RealEstateFinancing #MortgageLending #InvestmentProperty #RealDealChat #RealEstateInvestor #PassiveIncome #RentalProperty #RealEstateTips 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 Website Apple Podcasts YouTube YouTube Music Spotify Amazon Music Facebook Twitter Instagram