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

    1D AGO

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

    3D AGO

    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
  3. I Got Sick Chasing Deals — Here's What I Changed w/ Michael Coxen

    5D AGO

    I Got Sick Chasing Deals — Here's What I Changed w/ Michael Coxen

    Michael Coxen burned out chasing deals, ended up hospitalized with colitis, and then built his best business by becoming more mindful. Here's how. In this episode of RealDealChat, Jack Hoss sits down with Michael Coxen, Las Vegas real estate broker, investor, and host of The Mindful Agent Podcast, to explore the intersection of mindfulness, health, and business performance — and why intentional living turns out to be a better growth strategy than hustle. Michael covers: How ulcerative colitis hospitalized him multiple times and forced a complete resetWhy becoming more mindful was an accident — and how it led to his biggest career deal (a commercial office sale that came from a cycling group)The five-minute meditation that changed how he screens clients and avoids bad dealsWhy the gut feeling of dread before a deal is data, not weaknessThe Hidden Messages in Water — the science behind why what you consume (media, food, relationships) affects your performanceHow to hack your social media algorithm to feed you growth-oriented content instead of outrageWhy he gave up 50% of every commission to join a mentor's team — and why it was the highest-ROI decision he ever madeHow his brokerage (Magenta) runs a CRM action plan with systems before, during, and after every dealThe "certified settlement statement in January" system that generates referrals without a sales pitchContract language that keeps deadlines off Sundays and holidays — protecting his agents' weekendsWhy he'd rather someone bring a successful investor a deal and split it 50/50 than pay for a seminarThe Shadow Creek golf story: a $1,250 round, a stranger who paid for it, and the abundance mindset that makes it work This episode is for: Real estate agents and investors who feel burned out but keep pushing anywayAnyone building a referral-based business and wants the systems behind itEntrepreneurs interested in how mindfulness and intentionality affect performance — not just wellness 🔗 Find Michael at: https://michaelcoxen.com 🔗 Listen to The Mindful Agent Podcast #MindfulAgent #RealEstateInvesting #Burnout #RealEstateAgent #EntrepreneurMindset #RealDealChat #WorkLifeBalance #LasVegasRealEstate #MindfulnessInBusiness #RealEstateGrowth 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

    40 min
  4. How Real Estate Investors Can Pay Less for College w/ Brad Baldridge

    APR 2

    How Real Estate Investors Can Pay Less for College w/ Brad Baldridge

    Brad Baldridge breaks down how real estate investors and business owners can legally reduce college costs — using income control, asset positioning, and tax strategy. In this episode of RealDealChat, Jack Hoss sits down with Brad Baldridge, financial advisor and college planning specialist at Taming the High Cost of College, to unpack one of the most overlooked financial planning opportunities for real estate investors — using their assets and income control to dramatically reduce what they pay for their kids' college education. Brad covers: Why families come too late — and the ideal planning runway (sophomore year of high school)The difference between need-based aid and merit aid — and why elite private schools can actually be cheaper than you thinkWhy real estate investors and business owners have levers W-2 employees simply don't haveHow to use income control, bonus timing, and salary adjustments to improve your FAFSA positionWhy investment real estate must be reported as an asset (at net value, not gross) — and what that actually means for your aid calculationHow to shift income and assets to your student to unlock tax credits that phase out at higher income levelsReal case study: a teacher's family inherited $500K and still qualified for a full ride by repositioning assets correctlyReal case study: an engineering manager calculated that paying full price for NYU cost him 3 extra years of work — and decided that was fineWhy applying to five schools of the same type is one of the most common and costly mistakes families makeHow to vet a college financial advisor — and why most people don't know to ask about the CSS profile vs. FAFSABrad's take on AI: useful for research, not yet replacing expertise — and why the "AI will take all the jobs" panic is overblownNiching down: how becoming the college planning specialist transformed Brad's financial advisory practice This episode is for: Real estate investors who have kids approaching college ageBusiness owners who want to understand how income control affects financial aidAny parent who wants to stop leaving money on the table when paying for college 🔗 Learn more: https://taminghighcostofcollege.com #CollegePlanning #CollegeCosts #RealEstateInvesting #FinancialPlanning #FAFSAStrategies #RealDealChat #CollegeFinancialAid #BusinessOwner #MeritAid #CollegeSavings 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

    36 min
  5. Timberland Investing: Multiple Paydays from One Property w/ John Brenard

    MAR 31

    Timberland Investing: Multiple Paydays from One Property w/ John Brenard

    John Bernard of Southview Timber breaks down timberland investing — how it generates multiple income streams, why the Southeast is the top market, and how to get in. In this episode of RealDealChat, Jack Hoss sits down with John Bernard, co-founder of Southview Timber and manager of the Southview Timberland Fund, to break down one of the most overlooked asset classes in real estate investing. John covers: Why his family bought timberland in 2008 — and how 15 years at JP Morgan and Wells Fargo led him to democratize the asset classWhy the Southeast US (Georgia, North Florida, South Carolina, Alabama) is now the #1 timber region in North AmericaThe three ways a single property can generate returns: timber harvest, real estate appreciation, and development or recreational saleHow Southview sources deals entirely through personal relationships — and why outsiders simply can't access the same pipelineThe sweet spot: 200–2,000-acre mid-size properties that fall below institutional radar and above most individual investor budgetsUnderwriting criteria: proximity to mills (within 50 miles), soil productivity, access roads, and multiple buyer optionsWhy timberland investors can wait for the best timber prices — unlike farmland, there's no forced harvestHow demographic migration from the Northeast and West Coast is driving rural land values up in the SoutheastThe 500-acre deal they bought for $1M and exited in 60 days — selling parcels to a business and an adjacent landownerWhy John is cautious about AI-labeled startup investments — and why he prefers assets you can put boots on the ground to verifyCurrent bottleneck: capital. They have deal flow. The fund is nearly deployed and raising toward $50M. This episode is for: Accredited investors looking for non-correlated, tangible alternatives to stocks and cryptoReal estate investors who want to understand a high-margin niche with multiple exit optionsFamily offices and RIAs seeking a conservative real assets strategy 🔗 Learn more: https://southviewtimber.com 🔗 Find John on LinkedIn: John Bernard 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
  6. How AI Search Is Changing Where Seller Leads Come From w/ Trevor Mauch of Carrot.com

    MAR 29

    How AI Search Is Changing Where Seller Leads Come From w/ Trevor Mauch of Carrot.com

    Trevor Mauch of Carrot.com breaks down why more leads isn't the answer, why sellers ghost you, and how AI search is already changing deal flow. In this episode of RealDealChat, Jack Hoss sits down with Trevor Mauch, founder and CEO of Carrot.com, to zoom out from marketing tactics and talk about where real estate investing, AI, and online trust are actually heading. Trevor covers: The #1 assumption quietly killing investor deal flow — and why optimizing leads beats generating moreWhy "if you're not growing you're dying" is a lie — and the three real reasons business existsThe difference between a logo and an actual brand — and why 8 out of 10 investors don't have oneWhy sellers ghost you (spoiler: it's almost never about price)The "evergreen marketing" principle: how to build lead flow that doesn't require constant feedingWhat a real USP looks like in 2026 — and why "cash offer, close in 7 days" stopped being one years agoThe AI continuum: from untrained ChatGPT threads to well-trained coaches to autonomous agentsHow Carrot ingests seller call conversations and auto-recommends website updates to close objection gapsHow Google's AI overviews nearly doubled daily searches — and what that means for your SEOWhy a guy in Ohio got his first ChatGPT-sourced seller lead within 3 weeks of simple brand updatesThe human-AI balance: using technology to scale humanity, not replace itWhy efficiency gains from AI tend to create more work, not more freedom — and what to do instead This episode is for: Wholesalers, flippers, and agents who keep spending on leads and not seeing resultsInvestors who want to understand how AI search is already changing inbound deal flowAnyone building or refining their online presence and brand for 2026 🔗 Learn more at: https://carrot.com 🔗 Trevor's AI Search Challenge: carrot.com #RealEstateInvesting #LeadGeneration #RealEstateBrand #WholesaleRealEstate #AISearch #RealDealChat #CarrotCom #InvestorMarketing #SellerLeads #RealEstateTips Work With RealDealCrew If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper: Take the Deal Intake Assessment See how resilient your current operation actually is. → https://assessment.realdealcrew.com Book a Fit Call If you want to explore what a fully system-driven deal flow looks like, let’s talk. → https://realdealcrew.com/book LIKE • SHARE • JOIN • REVIEW WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram

    45 min
  7. The Founder Trap: Why Hard Work Is Keeping You Broke w/ Charles Gaudet

    MAR 27

    The Founder Trap: Why Hard Work Is Keeping You Broke w/ Charles Gaudet

    Charles Gaudet took a business from $950K to $66M in 7 years — and says hard work was the problem, not the solution. Here's the system he built. Full DescriptionIn this episode of RealDealChat, Jack Hoss sits down with Charles Gaudet, founder of Predictable Profits and coach to over 2,000 businesses, to break down why most entrepreneurs hit a wall at $1–3M — and the three-system framework that breaks through it. Charles covers: The Founder Trap: why success itself becomes the ceiling, and why doubling your leads can actually tank your businessWhy 66% of Inc. 5000 companies shrink, go under, or sell disadvantageously within 5–8 years of being listedThe real definition of marketing — and why even $500M CEOs don't know how to create, capture, and nurture demandWhy 100% of all buying decisions will be made before a prospect ever gets on the phone by 2030 (McKinsey and Gartner data)How he built one of the most profitable real estate development companies in his market — with zero prior experience — by working from a book and writing down contractor names off trucksThe hospital wake-up call that nearly killed him in his 20s and forced him to stop believing hard work alone was the answerReturn on Time (ROT) — the metric that separates real business owners from high-paid employeesWhy AI is just an accelerator — and why context and strategic thinking are the real competitive moatHow to use AI as a virtual board of directors, legal bot, and deal analyzer for real estate investmentsWhy Google's organic traffic dropped 60% in 2025 — and what that means for every investor's marketing plan This episode is for: Real estate investors and operators stuck between $1M and $10M who feel maxed outEntrepreneurs running a business that can't survive without themAnyone who wants to understand how to use AI strategically — not just to write emails 🔗 Learn more: https://predictableprofits.com 🔗 Build systems for your investing business: https://realdealcrew.com #EntrepreneurMindset #BusinessGrowth #RealEstateInvesting #ScalingBusiness #PredictableProfits #FounderTrap #AIForBusiness #RealDealChat #BusinessSystems #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

    47 min
  8. Why 90% of FSBOs Fail (And How to Be the 10%) w/ Tim Street

    MAR 25

    Why 90% of FSBOs Fail (And How to Be the 10%) w/ Tim Street

    Tim Street reverse-engineered the entire FSBO process into a 7-day blueprint — and his sellers get 102% of list price while saving $30K or more. In this episode of RealDealChat, Jack Hoss sits down with Tim Street, Marine-turned-real estate agent-turned-FSBO educator, to break down one of the most misunderstood niches in real estate. Tim covers: Why 90%+ of FSBOs fail — and why the ones that succeed still sell for 11% less than agent-listed homesThe 3-phase system: Prep & Protect, Price & Promote, Sell & SecureStrategic underpricing — how Tim achieved a 102.3% list-to-sold ratio by creating competitionThe "chaos in the driveway" open house strategy that forces buyers to write offers on their steering wheelsWhy a pre-listing inspection is the single most powerful move a FSBO can make before going liveThe "truth package" that takes all negotiating ammo away from buyersHis 90-day sell guarantee — and the operational safeguard behind itWhy he quit the listing game cold after watching a retired couple get lied to for a $500K promise on a $400K houseHow he uses Claude for narrative script writing and ChatGPT for operationsHis custom Hemingway-inspired GPT that writes listing descriptions buyers actually readWhy 24 touches across 3 platforms is the real follow-up standard — not 6 This episode is for: Real estate investors who want to understand the FSBO seller mindsetHomeowners tired of paying 3–6% commissionsAgents who want to stop losing listings to overpriced competitorsAnyone building a follow-up system around a skeptical, DIY-first audience 🔗 Get Tim's Investor Power Pack: https://foolprooffsbo.com/investors 🔗 Take the FSBO temperament quiz: https://foolprooffsbo.com/quiz #FSBO #ForSaleByOwner #RealEstateInvesting #HomeSelling #RealDealChat #RealEstateTips #HouseSelling #InvestorMindset #RealEstateAgent #HomeBuying 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

    37 min
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5
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81 Ratings

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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.

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