Real Estate Investing with RealDealChat

RealDealCrew / Jack Hoss
  • 5.0 (81)
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Real Estate Investing with RealDealChat is a podcast featuring interviews with experienced real estate investors, wholesalers, flippers, landlords, and operators actively closing deals. Each episode breaks down: • Real estate investing strategies • Deal sourcing and wholesaling tactics • Fix and flip systems • Rental property scaling • AI and automation tools for investors • Deal operations and lead management Hosted by Jack Hoss, a real estate investor and founder of RealDealCrew, the show focuses on practical execution — not theory. Whether you're wholesaling houses, flipping properties, building a rental portfolio, or scaling a real estate investing business, this podcast delivers real-world lessons from operators actively doing deals. Follow the show to get weekly insights on real estate investing strategies, deal flow systems, and operational growth.

  1. He Set a Goal of 40 Units. He Ended Up with 2,700 w/ Jens Nielsen

    15M AGO

    He Set a Goal of 40 Units. He Ended Up with 2,700 w/ Jens Nielsen

    Jens Nielsen left a 25-year IT career and went from 40-unit goal to managing 2,700 units — here's the exact path he took to scale commercial real estate. In this episode of RealDealChat, Jack Hoss sits down with Jens Nielsen — a former IT professional turned commercial real estate investor and high-performance coach — to break down how he went from a linear 10-year plan to managing over 2,700 units across multifamily, industrial, and flex space. Jens covers: How he started with a fourplex for $115K and scaled from thereWhy he ditched single-family immediately and went straight to small multifamilyThe mindset shift that unlocked syndications and other people's moneyWhy he pivoted from apartments to industrial and flex space when rates roseHow the EOS (Entrepreneurial Operating System) helped him manage a vertically integrated property management companyThe bridge loan mistake he'll never repeat — and what he does insteadHow high-performance coaching helped him earn more in his first year out of his W2 than ever beforeWhy he believes we'll all wish we bought more real estate in 2026 This one is for investors who are still thinking one deal at a time and need to see what happens when you stop thinking linearly. 🔗 Learn more about Jens: https://jensnielsen.us 🔗 Build systems for your investing business: https://realdealcrew.com #CommercialRealEstate #RealEstateInvesting #MultifamilyInvesting #FlexSpace #IndustrialRealEstate #RealEstateSyndication #PassiveIncome #HighPerformanceCoaching #RealDealChat #WealthBuilding #LeavingW2 #RealEstateInvestor 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-a-fit-call

    31 min
  2. Why the Next 3–5 Years Are the Best Ever for Notes w/ Eddie Speed

    2D AGO

    Why the Next 3–5 Years Are the Best Ever for Notes w/ Eddie Speed

    Eddie Speed has closed 50,000+ note deals in 45 years — and says the next 3–5 years may be the best window for note investing he's ever seen. In this episode of RealDealChat, Jack Hoss sits down with Eddie Speed, founder of NoteSchool, for a conversation 45 years in the making. Eddie has closed over 50,000 note deals, trained thousands of investors, and watched the real estate market cycle through every imaginable condition — and he's more fired up about notes right now than at any point in his career. Topics covered include: Why the next 3–5 years could be the greatest window for note investing Eddie has ever seenHow banks outperform landlords in inflationary markets — and why 2021 Facebook posts got it wrongThe difference between confidence and arrogance — and why confidence is the #1 driver of investor actionEddie's origin story: starting in notes at age 20 in a 10x40 mobile home and scaling to 50,000+ dealsWhy people aren't buying information — they're buying confidenceThe note investing myth Eddie has been trying to kill for 25 years (seller financing without underwriting)Notes on blockchain — the innovation Eddie says is the most exciting thing he's ever worked onWhy AI gets note-specific questions wrong and what to do about itHow Eddie manages severe dyslexia while running a major training businessThe John Travolta story (you'll have to listen for this one) This episode is essential for: Investors questioning whether notes make sense in today's marketLandlords frustrated by rising expenses and compressed marginsAnyone exploring seller financing as a strategyEntrepreneurs who want a masterclass in staying the course and reinventing when necessary 🔗 Special resources for RealDealChat listeners: https://noteschool.com/realdeal 🔗 Build systems for your investing business: https://realdealcrew.com #RealEstateInvesting #NoteInvesting #SellerFinancing #BeTheBank #PassiveIncome #RealDealChat #NoteSchool #PrivateMoney #WealthBuilding #RealEstateInvestor #CreativeFinance #LandlordAlternative 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

    35 min
  3. You Don't Own Your Brand (Until You Do This) w/ Joey Vitale

    4D AGO

    You Don't Own Your Brand (Until You Do This) w/ Joey Vitale

    Joey Vitale reveals why most entrepreneurs don't legally own their brand — and the trademark strategy that protects everything you're building. In this episode of RealDealChat, Jack Hoss sits down with Joey Vitale, founder of Indie Law and Skybreaker, to break down two things most entrepreneurs ignore until it's too late: trademark protection and offshore staffing systems. Joey shares the frameworks that helped him scale a seven-figure trademark law firm, step away from daily operations, and launch a second company — all while working less, not more. Topics covered: Why you don't legally own your brand without a trademarkHow over 500,000 trademark applications get filed annually — and more than half get deniedThe "Blue Apron vs. Green Apron" example that shows how broadly trademarks are interpreted (Starbucks lost this one)Why personal brand builders, coaches, and podcast hosts are the most exposedWhat the Matthew McConaughey AI trademark strategy reveals about where brand law is headingHow Joey built Skybreaker — an offshore VA recruiting firm — out of necessityThe "Swiss Army Knife VA" framework for hiring your first overseas team memberWhy your first VA hire should start with accountability and metric tracking, not salesHow AI is shifting (not replacing) the VA model — and what good delegation actually looks likeThe entrepreneur lie: focusing on revenue instead of profitability If you're building a business, a personal brand, or a real estate portfolio with any kind of recognizable name or system attached to it — this episode is a must-listen. 🔗 Learn more about Joey: https://indielaw.com 🔗 Build systems for your investing business: https://realdealcrew.com #RealEstate #Trademarks #PersonalBranding #EntrepreneurMindset #VirtualAssistants #BusinessSystems #RealDealChat #BrandProtection #OffshoreStaff #ScalingYourBusiness 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

    32 min
  4. Why Your Investment Property Is Probably Underinsured w/ Michael Silverman

    6D AGO

    Why Your Investment Property Is Probably Underinsured w/ Michael Silverman

    Michael Silverman reveals why most investment properties are underinsured — and the liability gaps that could cost investors everything. In this episode of RealDealChat, Jack Hoss sits down with Michael Silverman of Silver Lining Insurance Agency (slia.agency) — third-generation insurance broker with nearly 40 years of experience — to break down the insurance blind spots most real estate investors don't know they have. Michael covers: Why liability coverage is the #1 most overlooked protection for investorsHow building replacement costs have skyrocketed — and why outdated policies leave you exposedThe water leak detection system that saves investors thousands annually in premiumsA real claim story: a $1.6M policy that needed to be $2.9M — and a $5M+ total loss that was fully coveredWhat security cameras and smart systems can do for your insurance costsThe difference between market value and replacement value (and why it matters for your policy)How to review your coverage the right way — starting with one action you can take this weekWhat 9/11 changed about commercial insurance (terrorism coverage and what's required)Why insurance companies actually want to pay claims — and the real reason they sometimes don't This conversation is essential for: Real estate investors with one or more rental propertiesProperty managers overseeing commercial or mixed-use buildingsNew investors setting up their first policyAnyone who hasn't reviewed their coverage in the past 12–24 months If a building burned to the ground tomorrow, would your policy actually cover a rebuild? 🔗 Learn more about Silver Lining Insurance: https://slia.agency 🔗 Build systems for your investing business: https://realdealcrew.com #RealEstateInvesting #LandlordTips #PropertyInsurance #InvestorMindset #RealDealChat #LiabilityCoverage #RentalProperty #InsuranceTips #PropertyManagement #RealEstateBusiness #PassiveIncome #BuildingOwner #AssetProtection #WealthBuilding #RealEstateEducation 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

    30 min
  5. Turn One House Into 28 Doors with Co-Living w/ Katrina E. Robinson

    APR 12

    Turn One House Into 28 Doors with Co-Living w/ Katrina E. Robinson

    Katrina Robinson breaks down how co-living turns a single-family home into 28 doors — and how investors can 10X rental income without buying more properties. In this episode of RealDealChat, Jack Hoss sits down with Katrina E. Robinson, founder of Group Home on Autopilot and Round Table Living, to break down the co-living model that's helping real estate investors maximize income on existing properties while solving the affordable housing crisis. Katrina covers: Why renting by the bed vs. by the house can generate 10X the profit on a single propertyHow she went from 3 properties to 28 doors using shared housingThe detailed intake process for vetting residents and maintaining house harmonyWhat Texas's 2025 legal definition of "group home" means for co-living investorsProperty requirements: bedrooms, bathrooms, and public transit accessManaging difficult residents — including a near-elder-abuse sagaThe Kenya case study: from zero to two houses open in 5 monthsWhy military-style SOPs are the foundation of scaling this businessPadSplit, SpareRoom, Roomies, and 101+ ways to fill your beds This is essential for: Investors who want more cash flow without adding doorsAnyone considering pivoting to shared housing or affordable housingOperators looking to scale with systems, not stress 🔗 Learn more at: https://grouphomeonautopilot.com 🔗 Co-Living Business Conference (April 24–25): https://grouphomeonautopilot.com/CBC 🔗 Build systems for your investing business: https://realdealcrew.com #RealEstateInvesting #CoLiving #GroupHome #AffordableHousing #RentalIncome #SharedHousing #HouseHacking #RealDealChat #PropertyManagement #PassiveIncome #RealEstateTips #InvestorMindset #CashFlow #RealEstateStrategy #SFRInvesting 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

    34 min
  6. He Never Sold a Property. Now He Has 30 Buildings. w/ Onyi Odunukwe

    APR 10

    He Never Sold a Property. Now He Has 30 Buildings. w/ Onyi Odunukwe

    Onyi Odunukwe built 30 commercial properties without selling a single one — and his franchise strategy is what made it all possible. In this episode of RealDealChat, Jack Hoss sits down with Onyi Odunukwe — aka the Sweat Pant Millionaire — CEO of Glow Tanning (a top 500 franchise with 360+ locations) and owner of nearly 30 commercial properties, all acquired in just five years without selling a single one. Onyi breaks down: Why delayed gratification is the real skill behind commercial real estate wealthHow he uses his franchise (Glow) as the anchor tenant in every building he buysHis value-add strategy — great location, ugly building, bad tenants — and how he forces appreciationWhy he works harder to avoid taxes than to make money (and the tools he uses to do it)His cash-out refi strategy for living off tax-free income in retirementThe "one job per person" rule that keeps his 18 businesses runningWhy he gave away his commercial real estate course for free — and what he charges for mentorshipWhat the $500M PE offer on Glow revealed about concentration vs. diversificationHis take on generational wisdom vs. generational wealthWhy a chief of staff was his single best business investment This episode is essential for: Investors looking to scale into commercial real estateOperators running multiple businesses who are becoming the bottleneckAnyone thinking about the tax side of building a portfolio If you've been sitting on equity and not sure what to do next, Onyi's framework will sharpen your thinking. 🔗 Follow Onyi on Instagram: @sweatpantmillionaire 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

    33 min
  7. From 50 to 270 Deals: How Virtual Assistants Did It w/ Bob-Lachance

    APR 8

    From 50 to 270 Deals: How Virtual Assistants Did It w/ Bob-Lachance

    Bob Lachance went from 50 deals to 270 deals a year using virtual assistants — and built one of the top VA companies in real estate. Here's exactly how. In this episode of RealDealChat, Jack Hoss sits down with Bob Lachance, former pro hockey player turned real estate investor, co-founder of Fortune Builders, and CEO of REVA Global — one of the leading virtual assistant companies serving real estate investors. Bob covers: From ice hockey to real estate: how a $32K first deal turned into a full investing businessWhy the first deal exposed everything: no systems, no marketing, running to Home Depot three times a dayDoor knocking pre-foreclosures in 2004 — and the mindset shift that came from replacing himself in that roleWhy he co-founded Fortune Builders and what happened to it after COVIDThe real reason students fail even after buying coaching programs: accountability, not informationHow Bob discovered virtual assistants in 2013, launched REVA Global in 2014, and grew to 270+ deals a yearWhy all of REVA Global's VAs are based in the Philippines — and what makes that market uniquely suited for real estate supportThe four-team structure: sourcing and recruiting, training, placements, and client service managementWhere AI can't replace VAs: outbound calling, property management, admin work requiring real human judgmentTool stack: Salesforce, Podio, GoHighLevel, Smarter Contact — how Bob manages operations across time zonesThe $150,000 lesson: a knockdown rebuild in Greenwich, shiny object syndrome, and the FOMO deal that cost $160K totalWhy you shouldn't leave the owner's box too early — and the hiring mistake most investors make with VAsThree masterminds Bob attends (Boardroom, Collective Genius, Family Mastermind) and how to measure ROI on each"Learn it, live it, gift it" — the system for knowing when you're ready to hand something off This episode is for: Real estate investors doing 5–50 deals a year who feel maxed outAnyone who's tried hiring a VA and had it fail — and wants to understand whyOperators looking to build an actual team instead of staying a one-person show 🔗 Learn more: https://revaglobal.com 🔗 Build systems for your investing business: https://realdealcrew.com #VirtualAssistants #RealEstateInvesting #REVAGlobal #WholesaleRealEstate #RealEstateSystems #RealDealChat #ScalingBusiness #LeadGeneration #VirtualAssistantForRealEstate #RealEstateOperations 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

    33 min
  8. A Contractor Stole $104K — Here's What Kirk Built After w/ Kirk Welsh

    APR 6

    A Contractor Stole $104K — Here's What Kirk Built After w/ Kirk Welsh

    Kirk Welsh lost $104K to a contractor, then rebuilt with systems, accountability, and personal development. Here's the framework that changed everything. In this episode of RealDealChat, Jack Hoss sits down with Kirk Welsh — licensed architect, real estate investor, flooring company owner, and personal development coach — to have the conversation most real estate content avoids: the inner game of running a business. Kirk covers: The path from licensed architect to real estate investor to flooring company owner — and why entrepreneurship exposed everythingHow being the "doormat" (not the boss) led to a contractor walking off with $104,000Why your business is a direct reflection of who you are as a person — and what that means for operators stuck in chaosThe identity shift that happened after hiring a business coach — and how people around him reactedWhy "where you are right now is a direct result of the actions you've taken in the last 12–36 months"Discipline and structure must come before clarity — and why most people get this backwardsThe Iron Cowboy documentary: 101 Ironman triathlons in 101 days, and what his "bag of whys" made possibleKirk's four-step framework for getting through hard circumstances: establish your why, build the plan, execute the plan, reach back and teach someone elseStudying architecture entirely in Spanish in Puerto Rico — surviving Hurricane Maria, a school strike, and a drought — without quittingWhy faith and gratitude are what keep challenges looking like building blocks instead of setbacksAI speed-to-lead: how Atlas AI auto-responds to inbound calls so deals don't die in the first 30 secondsThe EA Playbook: DM Kirk on Instagram with "EA Jack" to get the exact system he uses with his executive assistant — free, no strings attached This episode is for: Real estate investors and operators who feel like their business depends entirely on themEntrepreneurs who've been the doormat with contractors, partners, or employeesAnyone who knows they need to work on themselves but hasn't made it the priority yet 🔗 Find Kirk on Instagram and LinkedIn: Kirk Welsh 🔗 DM "EA Jack" on Instagram for his free Executive Assistant Playbook 🔗 Build systems for your investing business: https://realdealcrew.com #RealEstateInvesting #PersonalDevelopment #EntrepreneurMindset #BusinessSystems #RealDealChat #Accountability #ContractorProblems #RealEstateFaith #LeadershipGrowth #SystemsBuilding 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

    28 min
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5
out of 5
81 Ratings

About

Real Estate Investing with RealDealChat is a podcast featuring interviews with experienced real estate investors, wholesalers, flippers, landlords, and operators actively closing deals. Each episode breaks down: • Real estate investing strategies • Deal sourcing and wholesaling tactics • Fix and flip systems • Rental property scaling • AI and automation tools for investors • Deal operations and lead management Hosted by Jack Hoss, a real estate investor and founder of RealDealCrew, the show focuses on practical execution — not theory. Whether you're wholesaling houses, flipping properties, building a rental portfolio, or scaling a real estate investing business, this podcast delivers real-world lessons from operators actively doing deals. Follow the show to get weekly insights on real estate investing strategies, deal flow systems, and operational growth.

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