Real Estate Investing with RealDealCrew

RealDealCrew / Jack Hoss
  • 5.0 (81)
  • Investing
  • Updated Semiweekly

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.

  1. 3d ago

    Wes Rowlands: How a $630M Investor Decides Which Goals Matter

    Wes Rowlands manages $630M and says most goals fail before they even start. Here's why. Wes Rowlands grew up broke, raised by a single mom on nine dollars an hour, and now manages over $630 million in assets across three investment firms. In this conversation he breaks down the framework he uses to decide which goals are actually worth pursuing, why he tells people to join five teams instead of hand-picking five mentors, and why real estate, private business, and public companies are the only three asset classes he trusts for the long term. Wes also gets into the $10,000 bet he made with a friend to force himself into entrepreneurship, why he ended his company's work-from-home policy, and the two persuasion levers (urgency and scarcity) he says instantly improve any pitch when used honestly. If you've ever set a goal you knew deep down you weren't going to hit, this episode explains why, and what to do instead. Key topics: The zero-to-ten test for knowing if a goal is real or just a wishHow "team gravity" builds accountability that willpower can'tWhy real estate, private business, and public companies made his top-3 list after 20 years managing moneyThe mindset shift from a caddying job that shaped how he thinks about earningWhy sales, not passive income, is the real path to financial independence About Wes Rowlands: Wes Rowlands is a wealth management partner overseeing more than $630 million in assets across private business, public companies, and real estate, and a competitive men's physique bodybuilder. Links: Follow Wes on Instagram: https://www.instagram.com/wes.rowlands/ 🔗 Build systems for your investing business: https://realdealcrew.com #RealEstateInvesting #WealthManagement #GoalSetting #Entrepreneurship #PassiveIncome #RealDealChat #BusinessGrowth #Mindset #Sales #TeamCulture #FinancialFreedom #InvestingTips #WallStreet #SmallBusiness Work With RealDealCrew If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper: Take the Deal Intake Assessment See how resilient your current operation actually is. → https://assessment.realdealcrew.com Book a Fit Call If you want to explore what a fully system-driven deal flow looks like, let’s talk. → https://realdealcrew.com/book LIKE • SHARE • JOIN • REVIEW WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram

    Wes Rowlands: How a $630M Investor Decides Which Goals Matter

  2. 5d ago

    How an AI Real Estate Brokerage Landed $50M in Week One w/ Jon Berryhill

    A real estate broker built a brokerage with zero agents, powered entirely by AI, in one week. Jon Berryhill is a former Army infantry sergeant and law enforcement officer who became a five-company entrepreneur and now runs a land and residential real estate operation with 52 agents. In this episode, Jon breaks down the AI-powered brokerage he just launched with zero human agents, which pulled in $50 million in potential listings in its first week. He also gets into the 30/60/90 day planning system he uses instead of long-term goals, the consistency framework behind his Agent Blueprint playbook, and how he thinks AI will make human-to-human connection more valuable, not less, in real estate. Key topics: How Jon built an AI-run real estate brokerage with no human agentsWhy he uses 30, 60, 90 day goals instead of five-year plansThe consistency habits behind his Agent Blueprint playbookGetting his real estate license at 43 after 18 years running other businessesWhy he believes AI strengthens human connection instead of replacing it Guest bio: Jon Berryhill is a real estate broker and entrepreneur running multiple companies, including a 52-agent land and residential brokerage and a newly launched AI-powered brokerage. Learn more at johnberryhill.com. Links: Learn more about Jon: https://johnberryhill.com🔗 Build systems for your investing business: https://realdealcrew.com #RealEstateInvesting #RealEstateAI #LandInvesting #RealEstateBrokerage #AIinRealEstate #RealDealChat #RealEstateAgent #PropTech #RealEstateLeads #Entrepreneurship #WarriorToWealth #RealEstateTech #PassiveIncome Work With RealDealCrew If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper: Take the Deal Intake Assessment See how resilient your current operation actually is. → https://assessment.realdealcrew.com Book a Fit Call If you want to explore what a fully system-driven deal flow looks like, let’s talk. → https://realdealcrew.com/book LIKE • SHARE • JOIN • REVIEW WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram

    How an AI Real Estate Brokerage Landed $50M in Week One w/ Jon Berryhill

  3. Sep 5

    Senior Housing at $40K a Room with Rod Khleif

    Rod Khleif is buying assisted living buildings at $40,000 a room. Replacement cost is $250,000. Rod Khleif lost $50 million in 2008 when a cross-collateralized package of 800 houses pulled his multifamily portfolio down with it. He rebuilt. His students now collectively own more than 305,000 units. In this conversation Rod walks through what he is buying right now, and the math is hard to believe until he shows it. He has two assisted living memory care facilities closed and five more under contract across San Antonio, Houston, and Dallas, at $40,000 per unit. Replacement cost on those same rooms runs $250,000 to $350,000. He calls it the best deal of his career, and he had to soften the occupancy assumptions on the proforma because the real numbers looked unbelievable. He also lays out why multifamily is in a tailspin, with roughly $1 trillion in debt coming due, sales down about 90 percent, and refinancing nearly impossible under current debt service coverage requirements. His read on it is straight Buffett: be greedy when others are fearful. In this episode: Why Rod walked away from senior housing in 2008 and came back to it nowThe silver tsunami math: 8,000 to 10,000 people a day turning 80, with only about 4% of needed beds getting builtHow he vets a senior housing operator, and the last-minute red flag that ended a dealWhy five units and up beats a fourplex, because value runs on net income instead of comparable salesA 296-unit property where a $25 parking spot created a $750,000 increase in value About Rod Khleif: Rod has owned and managed more than 2,000 homes and multiple apartment complexes, built 30 businesses, and hosts one of the largest commercial real estate podcasts in the world. He spent 26 years around Tony Robbins, eight of them on his team, and his Warrior coaching program is built around the same recovery methodology he used after 2008. Links: 🔗 Rod's free books, goal setting workshop, podcast, and $25 two-day bootcamp: https://rodslinks.com 📲 Text LINKS to 72345 📲 Accredited investors, text PARTNER to 72345 🔗 Build systems for your investing business: https://realdealcrew.com #RealEstateInvesting #SeniorHousing #AssistedLiving #Multifamily #CommercialRealEstate #ValueAdd #RodKhleif #RealDealChat #PassiveIncome #DistressedAssets #ApartmentInvesting #SyndicationDeals #SilverTsunami #CapRate Work With RealDealCrew If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper: Take the Deal Intake Assessment See how resilient your current operation actually is. → https://assessment.realdealcrew.com Book a Fit Call If you want to explore what a fully system-driven deal flow looks like, let’s talk. → https://realdealcrew.com/book LIKE • SHARE • JOIN • REVIEW WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram

    Senior Housing at $40K a Room with Rod Khleif

  4. Sep 3

    Retirement Planning for Business Owners w/ Amelia Misenheimer

    Your business is not your retirement plan. Amelia Misenheimer on what to build instead. Most businesses close, they don't sell. That's a hard thing to hear if you've spent a decade pouring every spare dollar back into the company and calling it a retirement strategy. Amelia Misenheimer comes from three generations of real estate, starting with a grandfather who was a dry land farmer in New Mexico and ended up holding tens of thousands of acres. She built her own rental portfolio, ran a property management company with over 450 properties, and bought investment property in England while living there as a military spouse. Today she works one on one with business owners and investors on the part almost nobody covers: the whole financial picture, not just the slice a financial advisor gets paid to manage. This conversation gets pointed fast. Amelia explains why advisors only count assets under management and ignore the real estate you already own, how fees of one to three percent drain accounts most people never open, and how one client is on track to save over $600,000 across 13 years simply by managing her own funds. Then she cuts through the creative financing hype: sub-to, wraparound contracts, and seller notes are not new, and most of those deals die because nobody ever asked the seller what they actually want. In this episode: Why your business revenue never reaches your kids, but your personal assets doThe hidden advisor fees you never write a check forThe client on track to save over $600,000 managing her own accountsCreative financing decoded, and how to pitch owner financing so the seller says yes1031 exchanges, capital gains, and the step-up in basis nobody explainsHow to tell a proactive accountant from a bean counter, and why October is the month that matters About Amelia Misenheimer Amelia is a licensed New Mexico realtor, real estate investor, and former property management company owner who now consults one on one with business owners and individuals on building wealth across real estate, retirement accounts, and everything in between. Connect with Amelia Misenheimer: 🔗 LinkedIn: https://www.linkedin.com/in/amelia-misenheimer/ 🔗 Substack: https://ameliamisenheimer.substack.com/ Work With RealDealCrew If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper: Take the Deal Intake Assessment See how resilient your current operation actually is. → https://assessment.realdealcrew.com Book a Fit Call If you want to explore what a fully system-driven deal flow looks like, let’s talk. → https://realdealcrew.com/book LIKE • SHARE • JOIN • REVIEW WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram

    Retirement Planning for Business Owners w/ Amelia Misenheimer

  5. Sep 1

    Why 100% Funded Deals Are Risky w/ Private Lender Jeff Cichocki

    A private lender who's closed 2,000+ deals explains why 100% funded deals are the riskiest move. Jeff Cichocki has closed over 2,000 real estate deals as a private lender and coach, and he's spent years watching guru culture push investors toward 100% funded, no money down deals. In this episode, he explains why that's backwards, why having skin in the game is what actually builds trust with a lender, and how a lack of it is quietly draining private lenders across the country right now. Jeff also walks through a real cost comparison between hard money and private capital, breaks down a creative deal structure that erased a $32,000 lien without paying it off, and flags the mortgage fraud red flag most investors don't realize they're committing. He closes with the reading and productivity habits, including his one-two-three method, that keep his team focused. Key topics: Why private lenders are losing money right now, and what's driving itThe real cost comparison between hard money and private capitalWhy sub-2, seller finance, and lease options aren't "creative finance"The mortgage fraud red flag most investors don't see comingThe one-two-three method for staying focused and getting more done Guest bio: Jeff Cichocki has closed over 2,000 real estate transactions as a private lender and coach, working both sides of the table as an investor and a funder. Links: Looking for funding on your next deal? bestreifunding.comWant to learn how to become a funder? myreicoach.com/trial (first month for a dollar)🔗 Build systems for your investing business: https://realdealcrew.com #RealEstateInvesting #PrivateLending #HardMoneyLending #RealDealChat #NoMoneyDown #RealEstateFinance #PrivateMoney #CreativeFinance #RealEstateTips #InvestorMindset #MortgageFraud #RealEstateLending #DealStructuring #RealEstateCoaching #Wholesaling Work With RealDealCrew If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper: Take the Deal Intake Assessment See how resilient your current operation actually is. → https://assessment.realdealcrew.com Book a Fit Call If you want to explore what a fully system-driven deal flow looks like, let’s talk. → https://realdealcrew.com/book LIKE • SHARE • JOIN • REVIEW WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram

    Why 100% Funded Deals Are Risky w/ Private Lender Jeff Cichocki

  6. Aug 30

    Building a Business That Doesn't Cost You Your Life w/ Jason Wojo

    A six-figure income didn't save his marriage, so this investor rebuilt everything from scratch. Jason Wojo cleared six figures his first year flipping houses, and it still cost him his marriage. He ended up selling his house and living on an air mattress in one of his own rehabs. That collapse forced him to rethink how he ran his business entirely, and the result became his book, Business for Life. In this conversation, Jason and Jack talk through what financial freedom actually means, why hustle culture quietly wrecks the things that matter most, and the exact framework Jason now uses to automate and delegate his way to a business that fits his life instead of consuming it. If you're making good money but feel like you're losing ground everywhere else, this one is worth the full listen. Key topics: Redefining financial freedom for real estate investorsThe three-step freedom formula for defining your vision before you buildThe "heaven's gates" exercise for figuring out what actually mattersThe SEAD framework (Strategize, Eliminate, Automate, Delegate)Why house flipping often turns into a disguised job Guest bio: Jason Wojo is a real estate investor, entrepreneur, and author of Business for Life: Building a Profitable Business That Gives You Your Time, Freedom, and Life Back. He holds two bachelor's degrees, a master's, and a PhD, and runs Life and Air, where he helps entrepreneurs build businesses around the lives they actually want. Links: Learn more from Jason at lifeanair.com 🔗 Build systems for your investing business: https://realdealcrew.com Work With RealDealCrew If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper: Take the Deal Intake Assessment See how resilient your current operation actually is. → https://assessment.realdealcrew.com Book a Fit Call If you want to explore what a fully system-driven deal flow looks like, let’s talk. → https://realdealcrew.com/book LIKE • SHARE • JOIN • REVIEW WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram

    Building a Business That Doesn't Cost You Your Life w/ Jason Wojo

  7. Aug 28

    Scaling a $250M NYC Real Estate Team w/ Ashley Reidy Quinn

    A $250M NYC broker admits her team has no CRM, and explains why psychology closes deals instead. Ashley Reidy Quinn is a partner at Asset Advisory Team in New York City, where she and her business partner Nick Montalbano have closed over a quarter billion dollars across Manhattan, Brooklyn, and the Hamptons. She started in the industry at 22 with a psychology degree and no real estate background, won her firm's Deal of the Year in her first year, and has spent the twelve years since building a six person team from scratch. In this episode, Ashley talks with Jack about what actually scales a real estate business, and it is not always what you would expect. She admits her team still doesn't run on a CRM, and explains why she considers that her biggest operational weak spot even as the business keeps growing. She also breaks down how a psychology degree shapes the way she manages clients and teammates, why the word no has become one of her most useful business tools, and how her team is using AI in ways that help and in ways that work against them with clients. This conversation is for any investor or agent trying to figure out whether systems or relationships are what actually scales a business. Ashley makes the case that in a people-first industry, the relationships come first, and the systems catch up later. Key topics: Scaling a real estate team without a CRM, and why that's a problem she's fixingHow a psychology degree shapes client and team managementThe operational differences between Manhattan, Brooklyn, and the HamptonsHiring lessons from her team's first hire to her most recent oneWhy silence, not rejection, kills a real estate dealWhere AI is helping her team, and where it's working against them About Ashley Reidy Quinn: Ashley is a partner at Asset Advisory Team, closing over a quarter billion dollars across Manhattan, Brooklyn, and the Hamptons alongside business partner Nick Montalbano. Links: 🔗 Build systems for your investing business: https://realdealcrew.com Find Ashley on Instagram: @ashreidy Work With RealDealCrew If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper: Take the Deal Intake Assessment See how resilient your current operation actually is. → https://assessment.realdealcrew.com Book a Fit Call If you want to explore what a fully system-driven deal flow looks like, let’s talk. → https://realdealcrew.com/book LIKE • SHARE • JOIN • REVIEW WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram

    Scaling a $250M NYC Real Estate Team w/ Ashley Reidy Quinn

  8. Aug 26

    New Jersey Real Estate Development w/ Patrick Southern

    A broker doing more than one deal a day on why busy isn't the same as making progress. Patrick Southern is one of the highest volume real estate brokers in New Jersey, closing 376 transactions last year while also building and repositioning multifamily development projects across the state. In this conversation, he walks through what it actually takes to build for a market that hasn't arrived yet, why municipal delays and affordable housing mandates are reshaping what gets built, and the mindset shift that separates agents who stay busy from agents who actually move forward. Key topics: Starting a site acquisition business at 19 and what it taught him about running a businessNearly two decades inside the Mike Ferry mentorship programEvaluating new construction and multifamily deals from land acquisition through exitWhy an affordable housing mandate can wipe out the middle tier of a marketThe real difference between action and progress, and why it matters more than effort About Patrick Southern: Patrick Southern is a top producing New Jersey real estate broker specializing in new construction and multifamily development, with a career spanning site acquisition, brokerage, and property investment. Links: Find Patrick at Properties by Southern on Instagram or propertiesbysouthern.com Work With RealDealCrew If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper: Take the Deal Intake Assessment See how resilient your current operation actually is. → https://assessment.realdealcrew.com Book a Fit Call If you want to explore what a fully system-driven deal flow looks like, let’s talk. → https://realdealcrew.com/book LIKE • SHARE • JOIN • REVIEW WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram

    New Jersey Real Estate Development w/ Patrick Southern
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About

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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