Real Estate Investing with RealDealCrew

RealDealCrew / Jack Hoss
  • 4.9 (82)
  • Investing
  • 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. 2d ago

    AI for Real Estate Investors: How to Train ChatGPT to Work Like You w/ Lauren Lucas

    Most real estate investors use AI like an upgraded Google. Lauren Lucas shows how to train it, automate lead gen, and analyze deals faster. Lauren Lucas went from a burnt-out agent to teaching AI for real estate at more than 150 live events across the US and two other countries. In this episode she explains why your AI output sounds generic and how to train ChatGPT or Claude on your voice in under 30 minutes. She also walks through the ManyChat comment-to-DM funnel that booked 200+ consultations in a year, with 187 showing up. And she makes the case that anyone in real estate without AI by the end of 2027 may never catch up. Questions answered in this episode: How do I train ChatGPT to sound like me instead of generic AI?How can real estate investors use AI to find leads they already have?What content should investors make to reach distressed and probate sellers?How does a ManyChat lead generation funnel work for real estate?Can AI analyze a real estate deal from my spreadsheet? About Lauren: Lauren Lucas is a real estate AI educator and the founder of the AIRE Elite Mastermind community on Skool, where she teaches agents and investors to put AI to work in their business. Join Lauren's Skool community: AI RE Elite Mastermind (skool.com) Instagram: @laurenlucas_re 🔗 Build systems for your investing business: https://realdealcrew.com Chapters: 00:00 No AI by 2027? Why you won't catch up 01:57 From burnt-out agent to AI educator 05:07 Learning AI from scratch with NotebookLM 06:45 Why your AI sounds generic and how to train it 10:13 AI quick win: find missed leads in your inbox 11:11 Use AI to find what your clients are asking 13:26 Why your database beats chasing new leads 15:19 Why automating chaos creates more chaos 18:04 Is AI slop killing your social media? 18:53 Text overlay posts that get shared and saved 21:01 Investors: stop making content for investors 21:47 Closing probate deals with a stairs video 23:08 Lead magnet + ManyChat comment automation 26:18 Big-company automation for $50 a month 28:25 How 187 of 200+ booked consults showed up 30:33 Build AI automations in phases, not all at once 32:07 Where AI in real estate is heading 34:06 AI deal analysis + 3 quick wins this weekend 36:25 Rapid fire: the lie investors tell themselves 36:53 Why to hire an admin before a salesperson 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

    AI for Real Estate Investors: How to Train ChatGPT to Work Like You w/ Lauren Lucas

  2. Oct 22

    1031 Exchange Into a DST: How to Stop Being a Landlord w/ Ashley Romiti

    Ashley Romiti explains how a 1031 exchange into a Delaware Statutory Trust (DST) lets landlords sell, defer the taxes, and go fully passive. Ashley underwrote over $500 million in real estate as a commercial broker before moving to the DST side, and today she helps 1031 investors stop being landlords without giving up the tax deferral. We cover what a DST is, how it lets you close in days instead of fighting the 45-day identification deadline, and why some deals carry a 30% fee load. She also shares the questions to ask any DST advisor and explains why younger investors still growing a portfolio should skip DSTs entirely. Questions answered in this episode: What is a Delaware Statutory Trust, and does it qualify for a 1031 exchange?How does a DST help you avoid the 45-day identification deadline?Who is a DST a good fit for, and who should avoid it?What fees should you check before investing in a DST?What questions should you ask a DST advisor? About Ashley: Ashley Romiti is a DST specialist with GCA 1031 and a former commercial real estate broker with 15 years on the advisory side, helping 1031 investors transition from active ownership to passive income. Links: Connect with Ashley and get her DST ebook: https://gca1031.com🔗 Build systems for your investing business: https://realdealcrew.com Chapters: 00:00 Why most investors lose on the exit 01:43 What underwriting $500M taught her about DSTs 03:59 1031 exchange basics: the taxes you defer 05:44 TIC vs DST: what is a Delaware Statutory Trust? 06:53 Why retiring landlords are moving into DSTs 07:26 DST sponsors: Bluerock, Cantor, Passco, Inland 07:48 $100K minimums and diversifying across DSTs 08:22 How DSTs handle debt replacement in a 1031 09:05 How a DST beats the 45-day identification rule 10:54 Who a DST is (and isn’t) right for 12:28 How to choose from 100+ DST deals 13:45 What is a 721 exchange into a REIT? 15:04 Step by step: a 1031 exchange into a DST 18:14 Getting comfortable with illiquidity 19:06 Are DSTs risky? The biggest misconceptions 19:48 DST fees: watch for a 30% fee load 21:26 Questions to ask before hiring a DST advisor 24:25 Why you shouldn’t trust AI on DST research 25:18 Plan your exit before you sell #1031Exchange #DelawareStatutoryTrust #RealEstateInvesting #DST #PassiveIncome #TaxDeferral #RealEstateInvestor #Landlord #REIT #CommercialRealEstate #RetirementPlanning #RealDealChat 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

    1031 Exchange Into a DST: How to Stop Being a Landlord w/ Ashley Romiti

  3. Oct 20

    Raising Capital for Real Estate: Why Investors Pass on Your First Deal w/ Jeffrey Fidelman

    Raising capital for real estate? Jeffrey Fidelman explains why investors pass on your first deal and fund your second. Jeffrey Fidelman has spent more than 12 years helping companies and real estate sponsors raise capital, and his team’s in-house fundraising CRM just launched as its own software, Fundex. He breaks down why first-time sponsors fail when they try to raise for a single SPV on a 30 to 60 day close, and why fundraising really runs three to nine months. He also shares how a real estate private equity fund raised close to $150 million in about nine months after losing 10 to 20 percent of contacted investors to spreadsheets in the past. If you’re raising money from investors beyond friends and family, this is how to build a pipeline that pays off on the next deal. Questions answered in this episode: Why do investors pass on a new sponsor’s first real estate deal?Why do first-time sponsors struggle to raise capital for an SPV?How long does it take to raise capital for a real estate deal?What does a lost investor lead actually cost you?Can you use a regular sales CRM like HubSpot to raise capital? About Jeffrey: Jeffrey Fidelman is the founder of a fundraise-as-a-service firm that helps companies and fund managers raise capital, and the founder of Fundex, a CRM built specifically for fundraising. He started his career running a buyers-only real estate brokerage in New York City before working at Morgan Stanley, HSBC, and a venture fund. Links: Fundex: https://usefundex.com 🔗 Build systems for your investing business: https://realdealcrew.com #RealEstateInvesting #RaisingCapital #RealDealChat #RealEstateSyndication #CapitalRaising #InvestorRelations #PrivateEquity #MultifamilyInvesting #RealEstateFunding #Fundex #CRM #Podcast Chapters: 00:00 Every lead you don’t follow up with is lost 01:31 Building a buyers-only brokerage after 2008 03:41 Should you niche down or stay a generalist? 05:06 Lessons from building through the 2008 crisis 09:55 Why capital follows investor relationships 11:29 What Fundex does for capital raising 14:51 Why sales CRMs don’t work for fundraising 15:32 Building the first version in Lovable 17:08 Did the no-code MVP save developer costs? 19:25 The 30-day reality of building with AI 21:15 Should you build with AI or hire developers? 22:55 Why raising capital for one SPV often fails 24:32 Why sponsors need an investment thesis 25:21 Why investors pass on your first deal 25:48 Building an investor pipeline for your next deal 27:52 Real estate fund raises nearly $150M in 9 months 29:09 The real cost of not following up with leads 30:29 Where interest rates go after the midterms 31:23 The lie entrepreneurs tell themselves 33:33 The biggest time saver: learning to say no 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

    Raising Capital for Real Estate: Why Investors Pass on Your First Deal w/ Jeffrey Fidelman

  4. Oct 15

    Laundromat Investing: The Truth About the 95% Success Rate w/ Ken Wimberly

    Is the 95% laundromat success rate real? Ken Wimberly of Laundry Luv explains why laundromats aren't passive income and what the numbers really say. Ken Wimberly is a former top Keller Williams commercial agent who got into laundromats while leasing out a shopping center in Abilene, Texas. He opened his first store right before COVID and now runs Laundry Luv, a franchise building large-format, staffed, full-service laundromats in B and C class shopping centers. Ken breaks down the most quoted stat in the industry, what it really costs to open a store, and the systems that took his company from break even to top-of-industry margins. If you've seen laundromats pitched as "set it and forget it" income, this is the reality check. Questions answered in this episode: - Is the 95% laundromat success rate accurate? - How much does it cost to open a laundromat? - Are laundromats really passive income? - How much revenue and profit does an average laundromat make? - Why are laundromats good tenants for shopping centers? About Ken: Ken Wimberly is co-founder of Laundry Luv, a Navy veteran, and a former top commercial agent with Keller Williams. Links: Laundry Luv: https://laundryluv.com Ken Wimberly: https://kenwimberly.com 🔗 Build systems for your investing business: https://realdealcrew.com Full transcript and episode page: https://realdealcrew.com/[episode number] Chapters: 00:00 Is the 95% laundromat success rate real? 01:43 How a shopping center deal led to laundry 04:18 Why laundromats make great anchor tenants 05:38 Building the Buc-ee's of laundromats 06:59 Why a kids' play area beats more washers 08:28 Staffed laundromats and full-service revenue 10:02 Are laundromats really passive income? 11:21 Opening a laundromat right before COVID 13:58 How documented systems grew their margins 15:02 How to market a laundromat with SEO, ads, and mailers 18:10 When a business should become a franchise 20:15 Who should buy a laundromat franchise? 21:30 How much does it cost to open a laundromat? 24:19 Average laundromat revenue and profit margins 26:35 How they raised laundromat profit margins 29:31 How EOS and Traction changed the company 31:24 Where to start if you want to buy a laundromat 33:22 The lie real estate investors tell themselves 34:31 Why his first hire was an integrator 35:44 Using Granola AI to save hours on meetings #LaundromatInvesting #RealEstateInvesting #LaundromatBusiness #Laundromat #Franchise #PassiveIncome #CommercialRealEstate #ShoppingCenter #SmallBusiness #EOS #Entrepreneurship #BusinessSystems #RealDealChat 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

    Laundromat Investing: The Truth About the 95% Success Rate w/ Ken Wimberly

  5. Oct 13

    Raise Capital Before the Deal: How Ken Gee Wins Apartments Without Overpaying

    Raise capital first, win the deal second. Ken Gee explains how he buys Florida apartments without being the highest bidder. Ken Gee is a former Deloitte CPA and commercial lender who now runs KRI Partners, a multifamily company with apartments across Florida, all managed from Cleveland. He explains why he flipped the usual syndication model and raises the money before he finds the deal, which lets him win properties without paying the most. He also shares how a $500 car service got Florida brokers to take an out-of-state buyer seriously, and how running a flight school taught him the checklists and systems behind a decentralized portfolio. If you want to scale into multifamily or invest outside your backyard, this one is for you. Questions answered in this episode: Should you raise money before you find a real estate deal?How do you win an apartment deal when there are 20 offers on it?How do you get brokers to take an out-of-state investor seriously?How do you run apartments in another state without getting buried?How do you keep property management from eating all your time? About Ken Gee: Ken Gee leads KRI Partners, which owns apartment communities across Florida. Before real estate he was a commercial lender, spent seven years as a CPA at Deloitte, and owned a Part 141 flight school that trained pilots for the Delta Connection program. Links: Learn more about Ken and KRI Partners: https://KRIPartners.com 🔗 Build systems for your investing business: https://realdealcrew.com Chapters: 00:00 Winning deals without being the highest bidder 01:25 From Deloitte CPA to flight school owner 04:32 Buying a flight school right before 9/11 05:15 Using pilot checklists to run rental properties 06:12 Why a CPA working 80 hours chose real estate 08:56 Why people watch others get rich and don't act 11:51 Why your 9 to 5 isn't as safe as you think 13:24 First 3 apartment buildings: $500K in 3 years 14:43 Why comfort is the most dangerous place to be 17:14 Should you listen to people who say you can't? 21:51 Why fitting in keeps you from building wealth 23:52 Get in the room with investors who've done it 26:29 Investing out of state: Cleveland to Florida 27:53 The $500 move that made brokers notice him 29:42 How to win when every deal has 20 offers 30:35 Raise the money first, then find the deal 31:21 Solve big problems one small piece at a time 33:24 The lie real estate investors tell themselves 34:01 How to stop property management whack-a-mole 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

    Raise Capital Before the Deal: How Ken Gee Wins Apartments Without Overpaying

  6. Oct 8

    Raising Private Money for Real Estate: $1M From One Free Workshop w/ George Hanna

    George Hanna raised $1M in his first free workshop. Here’s how real estate investors raise private money by building trust before they pitch. Most real estate investors try to raise capital by meeting strangers one on one and pitching the deal. George Hanna, founder of Smart Income Lifestyle, built trust first through free weekly workshops, then raised around $1 million in his first real estate investing session and up to $5 million after that. He explains why teaching before you sell kills the deal, the 7 hour rule for turning a stranger into an investor, and why AI only scales the chaos in a business without systems. If you want to attract private money instead of chasing it, this one is for you. Questions answered in this episode: How do you raise private money for real estate without pitching strangers?What is the 7 hour rule for building investor trust?What should a real estate investor workshop include?Why doesn’t AI fix a real estate business without systems?How do you create SOPs for a real estate investing business? About George: George Hanna helps business owners build systems, automations, and AI into their businesses so they run without the owner in every task. His background is in marketing and sales, and he started his first business in 2008. Links: Connect with George: https://smartincomelifestyle.com🔗 Build systems for your investing business: https://realdealcrew.com #RealEstateInvesting #PrivateMoney #RaisingCapital #RealDealChat #RealEstateInvestor #CapitalRaising #BusinessSystems #SOPs #AIForBusiness #Automation #Delegation #InvestorRelations #RealEstatePodcast 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

    Raising Private Money for Real Estate: $1M From One Free Workshop w/ George Hanna

  7. Oct 6

    California Landlord Law: Why Tenants Play Dirty and How to Win w/ Niv Davidovich

    California landlord attorney Niv Davidovich explains how landlords win in tenant-friendly cities, from screening to rent control to finding deals. Niv Davidovich runs a law firm that represents only landlords, with a litigation practice focused on Southern California. In this episode, he explains why some California cities are far tougher on landlords than the rest of the state, why tenant screening is the best way to stay out of court, and how local rent control rules can change from one side of a street to the other. He also shares where he sees opportunity in a discounted Los Angeles market, including converting parking spaces into ADUs. Questions answered in this episode: Is California really bad for landlords, or is it only certain cities?Can California landlords refuse Section 8 vouchers?How do you know which rent control law applies to your property?Is it worth hiring a lawyer to collect money someone owes you?How can investors still find deals in Los Angeles? About Niv: Niv Davidovich is the founder of Davidovich Law, a California firm that represents only landlords in litigation and handles real estate transactions nationally. Before law school he was a songwriter and music producer. This episode is educational, not legal advice. Talk to a licensed attorney in your state before acting on anything discussed. Connect with Niv: https://davidovichlaw.com 🔗 Build systems for your investing business: https://realdealcrew.com Chapters: 00:00 Why landlords lose to tenant advocates 01:20 From music producer to landlord attorney 05:47 Is California really anti-landlord? 09:18 Are tenants using ChatGPT to beat landlords? 10:12 Which California areas are toughest on landlords 11:58 How tenant screening prevents legal trouble 12:42 Can California landlords refuse Section 8? 13:24 How to screen without saying no 14:50 Which landlord cases are worth hiring a lawyer 16:00 Is it worth suing to collect $50K? 16:45 Which rent control law applies to your property? 18:06 How build dates decide rent control 18:27 A city border through the middle of a building 19:30 Is Los Angeles real estate on sale right now? 21:25 Buying half-empty rent-controlled buildings 22:17 Turning parking spaces into ADUs 26:47 How relocation fees kill new housing 29:07 Can LA turn around for landlords? 34:08 The lie landlords tell about late rent 34:49 How AI and delegation save a law firm time #LandlordTips #RentControl #RealEstateInvesting #TenantScreening #California #Section8 #ADU #LosAngelesRealEstate #LandlordLife #PropertyManagement #RealEstatePodcast #RealDealChat 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

    California Landlord Law: Why Tenants Play Dirty and How to Win w/ Niv Davidovich

  8. Oct 1

    Commercial Real Estate Lessons From Losing 200 Units in 2008 w/ Stewart Heath

    Stewart Heath lost 200 units in 2008 by trusting the bank. Now he buys only boring, stabilized commercial real estate. Stewart Heath is a CPA with more than 35 years of experience and a returning RealDealChat guest. Before 2008 he owned about 200 units across Nashville and Franklin, Tennessee, and he let his lenders' approval stand in for his own underwriting. Today his firm buys only stabilized medical office, suburban office, and mixed-use properties along the I-65 corridor from Nashville to Birmingham, using fixed-rate debt and a simple motto: boring is beautiful. He and Jack cover what 2008 taught him, why deals still work at 2026 rates, and why he thinks off-market deals are overrated. Questions answered in this episode: Can you trust a bank's approval as a second opinion on your deal?Do commercial real estate deals still pencil with rates near 6%?Why didn't the commercial "debt wall" create the distressed deals investors expected?Is medical office a better investment than self-storage right now?Are off-market commercial deals really better than listed ones? Stewart Heath is a CPA, commercial real estate investor, and author of the free book Don't Do What I Did. His firm buys and manages stabilized commercial properties for investors seeking tax-advantaged cash flow. 📘 Get Stewart's free book: https://harvardgracecapital.com/book/ 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

    Commercial Real Estate Lessons From Losing 200 Units in 2008 w/ Stewart Heath
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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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