Real Estate Investing with RealDealCrew

Hosted by RealDealCrew / Jack Hoss

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300

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Oct 2026

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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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October 22, 202627 min

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 Website Apple Podcasts YouTube YouTube Music Spotify Amazon Music Facebook Twitter Instagram

October 20, 202635 min

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 Website Apple Podcasts YouTube YouTube Music Spotify Amazon Music Facebook Twitter Instagram

October 15, 202636 min

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 Website Apple Podcasts YouTube YouTube Music Spotify Amazon Music Facebook Twitter Instagram

October 13, 202635 min

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 Website Apple Podcasts YouTube YouTube Music Spotify Amazon Music Facebook Twitter Instagram

October 8, 202637 min

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 Website Apple Podcasts YouTube YouTube Music Spotify Amazon Music Facebook Twitter Instagram

October 6, 202635 min

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 Website Apple Podcasts YouTube YouTube Music Spotify Amazon Music Facebook Twitter Instagram

October 1, 202632 min

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 Website Apple Podcasts YouTube YouTube Music Spotify Amazon Music Facebook Twitter Instagram

September 29, 202646 min

Tax Lien Investing: 13-18% Secured by Real Estate w/ Stephen Morel

Banks have earned 13 to 18% on unpaid property taxes for 100 years. Here's how tax liens work. Every year, over $20 billion in property taxes goes unpaid in America, and investors buy billions of that debt from counties as tax liens. The returns are strong and secured by real estate, but 50 different state rulebooks have kept the game mostly in the hands of hedge funds and banks. Stephen Morel is a 20-year title attorney out of New Orleans. After Hurricane Katrina flooded his home, he built a title insurance program that put roughly 12,000 abandoned properties back into productive use. Now he's founder of JurisDeed, a platform built to make tax lien investing accessible to everyday investors. In this episode: How a tax lien works, and why it's like buying a mortgage from the county Why about 90% of tax liens pay back with interest, and only about 1% end in foreclosure Why state-by-state laws keep most investors out How Stephen uses AI to build legal tech where "mostly right" means you lose Rapid fire: the lie investors tell themselves, his first hire, and his biggest time saver Guest: Stephen Morel, founder of JurisDeed and host of the Innovative Investor podcast Links: Get on the JurisDeed waitlist (closed beta): https://jurisdeed.com Listen to Innovative Investor: https://podcasts.apple.com/us/podcast/the-innovative-investor-podcast-property-debt-wealth/id1877715388 #TaxLienInvesting #TaxLiens #RealEstateInvesting #PassiveIncome #TaxDeeds #AlternativeInvestments #RealEstateAttorney #TitleInsurance #PropTech #AIinRealEstate #HurricaneKatrina #NewOrleans #InvestingForBeginners #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 Website Apple Podcasts YouTube YouTube Music Spotify Amazon Music Facebook Twitter Instagram

September 27, 202634 min

How to Niche Down in Commercial Real Estate w/ Bob Knakal

Bob Knakal has closed $25 billion in NYC real estate by doing less. Here's how saying no built his career. After 43 years brokering New York real estate, two firings from the biggest firms in the business, and a fresh start with BKREA in 2024, Bob Knakal sold 43 properties for $1.8 billion in his first full year back on his own. He joins Jack to break down why narrowing your focus beats chasing every deal, and how proprietary information and relentless fundamentals create an edge nobody can copy. In this episode: Why Bob turns down 3 to 4 times more listings than he competes for The Map Room: 220 hours walking an empty Manhattan that won 104 of 106 listing pitches How specializing literally creates time The Stonecutter's Creed and why most brokers quit too soon Why AI will push more professionals out of big firms and into boutiques Bob Knakal is the founder of BKREA and co-founder of Massey Knakal Realty Services, which sold to Cushman & Wakefield for $100 million. He has closed 2,422 deals covering 100 million square feet and co-wrote Selling Buildings: A Tactical Playbook with Rod Santomassimo. Connect with Bob: 🌐 https://bkrea.com 📧 bk@bkrea.com 📞 917-509-9501 #RealDealChat #CommercialRealEstate #RealEstateInvesting #CRE #RealEstateBroker #NYCRealEstate #BobKnakal #Specialization #AIinRealEstate #Entrepreneurship #SalesTips #ProspectingCalls #RealEstateDevelopment #BrokerLife 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

September 25, 202652 min

AI and Real Estate: Why Rentals Are Now a Must w/ Dustin Heiner

AI is cutting white-collar jobs fast. Dustin Heiner explains why rental cash flow is now a must. After 20 years of telling people they should invest in real estate, Dustin changed his message. With AI layoffs hitting tech, bookkeeping, and customer service, he now says you must. Dustin has been "successfully unemployed" for 10 years, owns 30+ single-family rentals and roughly 1,000 apartment units, and made more money during the 2008 crash than before it. He and Jack get into why cash flow holds up when jobs and markets don't, and why most people who buy rentals are running a hobby, not a business. In this episode: The $500 a month rule and how 20 rentals becomes $120K a year Why shelter is the income stream AI can't take over The green light / red light system for killing bad deals early Why you call the property manager before you make an offer The 6 ways one rental property makes you money Dustin Heiner hosts the Master Passive Income podcast, with 2.3 million downloads and a top ranking for real estate investing on Apple Podcasts, and built the Income Builder deal analysis platform. 🔗 Dustin's deal analyzer (free account): https://incomebuilder.io 📚 Dustin's free course: text RENTAL to 33777 or visit masterpassiveincome.com/freecourse 📱 Instagram: @thedustinheiner 🔗 Build systems for your investing business: https://realdealcrew.com #RealEstateInvesting #PassiveIncome #RentalProperty #CashFlow #AIJobs #FinancialFreedom #IncomeBuilder #BuyAndHold #RealEstateBusiness #LandlordLife #GenerationalWealth #DustinHeiner #MasterPassiveIncome #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 Website Apple Podcasts YouTube YouTube Music Spotify Amazon Music Facebook Twitter Instagram

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