Real Estate Investing with RealDealChat

RealDealCrew / Jack Hoss
  • 5.0 (80)
  • INVESTING
  • UPDATED SEMIWEEKLY

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. 1D AGO

    Nearshore vs Offshore Talent: What Actually Works w/ Brian Samson

    Brian Sampson breaks down nearshore vs offshore talent, critical thinking vs scripted VAs, and how Latin America teams create true ROI for real estate operators. In this episode of RealDealChat, Jack Hoss sits down with Brian Sampson, co-founder of PLUG, to unpack the real differences between offshore, nearshore, and onshore talent — and why it matters more than ever in the age of AI. If you’re a real estate investor, realtor, or operator using virtual assistants, this conversation will challenge how you think about cost savings versus business multiplication. We cover: Offshore vs nearshore definitionsWhy scripted call centers damage brand equityCritical thinking vs process-following talentAI answering services vs human problem solversThe hidden cost of Fiverr and UpworkLatin America talent pools (Nicaragua, Costa Rica, Brazil, Mexico)The three layers of labor arbitrageUsing AI tools like n8n to amplify remote teamsLoyalty, longevity, and turnover differencesWhy entrepreneurs should think ROI, not expense Brian explains why nearshore talent often costs slightly more than Asia — but produces dramatically higher long-term return through cultural alignment, time zone overlap, and independent problem-solving. If you’re trying to scale your team without racing to the bottom on hourly rates, this episode is for you. Learn more: https://plug.tech Build smarter systems: https://realdealcrew.com Work With RealDealCrew If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper: Take the Deal Intake Assessment See how resilient your current operation actually is. → https://assessment.realdealcrew.com Book a Fit Call If you want to explore what a fully system-driven deal flow looks like, let’s talk. → https://realdealcrew.com/book LIKE • SHARE • JOIN • REVIEW WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram Mentioned in this episode: intro to RealDealCrew book a Fit Call at RealDealCrew.com

    28 min
  2. Why Most Real Estate Investors Plateau with John Donnelly

    3D AGO

    Why Most Real Estate Investors Plateau with John Donnelly

    John Donnelly shares why most real estate investors plateau — and the mindset, systems, and accountability needed to break through. In this episode of RealDealChat, John Donnelly joins Jack to unpack a problem most investors quietly face: growth ceilings. We explore why operators often stall after early wins, how identity and self-concept cap performance, and why systems only work when they’re aligned with personal clarity. John shares insights on: Breaking through revenue plateausWhy mindset > tactics long termThe danger of chasing strategies without alignmentAccountability and peer environmentsSimplifying instead of stacking complexityWhen to double down vs pivot This is a practical conversation for investors who aren’t beginners anymore — but know they’re capable of more. If you’ve felt stuck at the same income level, deal volume, or business structure, this episode will give you a sharper lens. 🔗 Learn more at: https://realdealcrew.com Work With RealDealCrew If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper: Take the Deal Intake Assessment See how resilient your current operation actually is. → https://assessment.realdealcrew.com Book a Fit Call If you want to explore what a fully system-driven deal flow looks like, let’s talk. → https://realdealcrew.com/book keywords: real estate mindset, John Donnelly, investor growth ceiling, real estate accountability, scaling real estate business, investor plateau, real estate peer groups, entrepreneurial mindset, real estate systems, operator identity, RealDealChat podcast LIKE • SHARE • JOIN • REVIEW WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram Mentioned in this episode: book a Fit Call at RealDealCrew.com intro to RealDealCrew

    45 min
  3. Why 82% of Homeowners Regret Their Purchase with Kim Costa

    5D AGO

    Why 82% of Homeowners Regret Their Purchase with Kim Costa

    Kim Costa explains why 82% of homeowners regret their purchase — and how aligning your home with your identity changes everything. In this episode of RealDealChat, Kim Costa — author of Live in Your Wheelhouse and host on The American Dream TV — breaks down the psychology behind real estate decisions. Kim introduces her framework built around: The Four M’s (Myself, Mastery, Mission, Mates)The Wheel of Life across 8 key areasWhy most buyers move without clarityThe statistic that 82% of homeowners report regretHow real estate agents can shorten buying cyclesHow AI tools like Claude and ChatGPT help scale contentWhy slowing down leads to better long-term decisions We also explore Kim’s personal journey — from 27 years in accounting to design, authorship, and building a life aligned with her creativity. If you’ve ever felt misaligned in your home, career, or investment strategy, this episode will challenge how you think about real estate decisions. 🌐 Learn more: 👉 https://lifestylefoundations.com keywords: home buying psychology, Kim Costa, Live in Your Wheelhouse, homeowner regret statistics, real estate alignment, realtor differentiation strategy, wheel of life real estate, Maslow hierarchy home buying, house hacking mindset, AI for real estate agents, RealDealChat podcast Call to Action: If this episode helped you rethink alignment in home buying or investing, share it with one investor friend — and learn more at https://realdealcrew.com Work With RealDealCrew If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper: Take the Deal Intake Assessment See how resilient your current operation actually is. → https://assessment.realdealcrew.com Book a Fit Call If you want to explore what a fully system-driven deal flow looks like, let’s talk. → https://realdealcrew.com/book LIKE • SHARE • JOIN • REVIEW WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram Mentioned in this episode: intro to RealDealCrew book a Fit Call at RealDealCrew.com

    34 min
  4. How to Increase Airbnb Revenue 23% (Without More Units) w/ Dan Rivers

    MAR 1

    How to Increase Airbnb Revenue 23% (Without More Units) w/ Dan Rivers

    Dan Rivers explains how short-term rental owners can increase Airbnb revenue by 20%+ using listing optimization, pricing strategy, and revenue management. In this episode of RealDealChat, Jack Hoss sits down with Dan Rivers, founder of Synergy Stays, to break down what most Airbnb hosts get wrong about revenue management. Dan shares how his clients average a 23% revenue lift in year one, and why many operators are unknowingly leaving thousands on the table. We cover: The biggest Airbnb listing mistakesWhy professional photography still mattersHow to move from 50th to 75th percentile in your marketLeveraging length-of-stay discounts correctlyWhy loosening cancellation policies can increase revenueThe danger of “set it and forget it” pricing toolsWhen to scale vs. optimize your existing portfolioWhy passive investing isn’t actually passive Dan also shares his personal journey through heart surgery, mindset shifts, and building a business with focus instead of shiny object syndrome. If you own short-term rentals — or are thinking about it — this episode will sharpen your strategy. 🔗 Learn more about Synergy Stays: https://synergystayslocal.com 🔗 Build systems for your real estate business: https://realdealcrew.com Work With RealDealCrew If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper: Take the Deal Intake Assessment See how resilient your current operation actually is. → https://assessment.realdealcrew.com Book a Fit Call If you want to explore what a fully system-driven deal flow looks like, let’s talk. → https://realdealcrew.com/book LIKE • SHARE • JOIN • REVIEW WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram Mentioned in this episode: book a Fit Call at RealDealCrew.com intro to RealDealCrew

    37 min
  5. Opportunity Zones Are Permanent: What Investors Need to Know with Ashley Tison

    FEB 27

    Opportunity Zones Are Permanent: What Investors Need to Know with Ashley Tison

    Ashley Tison explains how Opportunity Zones became permanent — and how investors can defer, reduce, and potentially eliminate capital gains taxes. In this episode of RealDealChat, Ashley Tison of OZ Pros breaks down Opportunity Zones in plain English — what they are, how they work, and why the recent legislative updates changed the long-term strategy for investors. We cover: How Opportunity Zones were created under the Tax Cuts and Jobs ActThe “defer, reduce, eliminate” frameworkWhat the new rolling 10-year election meansHow investors can potentially write down gains before 2026Why long-term holds now outperform IRR-chasing churnReal examples of community transformation projectsHow much capital gain you actually need to get started Ashley also shares his origin story — from Air Force Academy and big law to niching down exclusively into OZ strategy — and why specialization built authority. We discuss hiring mistakes, scaling lessons, HubSpot AI automation, and how customized GPTs are supporting tax documentation workflows. If you have capital gains now — or expect to in the future — this episode will help you understand whether Opportunity Zones deserve a place in your long-term wealth strategy. 🌐 Learn more at: 👉 https://ozpros.com/podcast 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 Keywords: Opportunity Zones investing, Ashley Tison, capital gains tax strategy, qualified opportunity fund, defer capital gains tax, eliminate depreciation recapture, tax advantaged real estate, OZ 2027 updates, long term real estate investing, HubSpot AI automation, RealDealChat podcast Mentioned in this episode: book a Fit Call at RealDealCrew.com intro to RealDealCrew

    35 min
  6. Why 100% Loan-to-Cost Lending Is Working in the Midwest with Matthew Medrano

    FEB 25

    Why 100% Loan-to-Cost Lending Is Working in the Midwest with Matthew Medrano

    Matthew Medrano shares how Dynamo Capital scaled from a $5M goal to a $100M+ private credit fund by focusing on speed, alignment, and Midwest lending. In this episode of RealDealChat, Matthew Medrano of Dynamo Capital breaks down how a frustrated mortgage broker built a direct lending fund focused on fast funding, flexible terms, and aligned incentives. We cover: Why Dynamo offers 100% loan-to-cost on select fix-and-flip projectsHow they structured their fund without the traditional “2 and 20” modelWhy Midwest lending looks different than Wall Street lendingThe painful lessons from 30 duplex developmentsScaling from a $5M goal to over $100M in just two yearsWhy doing the right thing simplifies decision-making Matthew also shares how Dynamo uses AI and custom-built tech (including monday.com and in-house development) to free up staff for human interaction — not replace it. The result? More meaningful borrower relationships and better underwriting discipline. If you’re raising capital, deploying capital, or borrowing capital — this conversation gives you a behind-the-scenes look at how a private credit fund really operates. 🌐 Learn more: 👉 https://dynamocapital.com Work With RealDealCrew If you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper: Take the Deal Intake Assessment See how resilient your current operation actually is. → https://assessment.realdealcrew.com Book a Fit Call If you want to explore what a fully system-driven deal flow looks like, let’s talk. → https://realdealcrew.com/book LIKE • SHARE • JOIN • REVIEW WebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram Keywords: private lending fund, Matthew Medrano, Dynamo Capital, 100% loan to cost, fix and flip lending, Midwest real estate investing, private credit real estate, fund incentive alignment, no 2 and 20 fund structure, business purpose lending, AI in lending, RealDealChat podcast Mentioned in this episode: book a Fit Call at RealDealCrew.com intro to RealDealCrew

    45 min
  7. From Wall Street to 500M+ in Apartments: Lessons in Discipline w/ Michael Pouliot

    FEB 23

    From Wall Street to 500M+ in Apartments: Lessons in Discipline w/ Michael Pouliot

    Michael Pouliot shares why vertical integration, disciplined buy boxes, and patience are key as multifamily heads into a major refinance cycle. In this episode of RealDealChat, Michael Pouliot—fourth-generation real estate entrepreneur and founder of Carbon—breaks down what’s really happening in multifamily as the 2025–2027 maturity wall approaches. We discuss raising capital ahead of distress, why the downturn took longer than expected, and how today’s opportunities are often coming from exhausted sponsors or lender takebacks. Michael explains why bringing property management in-house created millions in value, how repairing HVACs instead of replacing them changed asset economics, and why ownership mindset matters at every level of the organization. We also dive into: How a disciplined buy box saves thousands of underwriting hoursWhy “rates will be lower next year” is the most common investor lieHow Carbon uses AI and custom GPT agents inside property managementWhy location quality ultimately outperforms chasing high cap ratesWhat Michael learned from Wall Street’s “two strike” culture If you’re investing in multifamily—or preparing for the next phase of this cycle—this conversation will sharpen your framework. 🌐 Learn more & subscribe to Michael’s newsletter: 👉 https://investwithcarbon.com keywords: multifamily investing 2026, Michael Pouliot, vertical integration real estate, multifamily maturity wall, distress real estate cycle, apartment syndication strategy, property management optimization, multifamily buy box strategy, AI in property management, commercial real estate outlook, Carbon real estate, RealDealChat podcast 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 Mentioned in this episode: book a Fit Call at RealDealCrew.com intro to RealDealCrew

    32 min
  8. Subject-To Real Estate Done Right with Caleb Christopher

    FEB 21

    Subject-To Real Estate Done Right with Caleb Christopher

    Caleb Christopher breaks down subject-to real estate, wraparound mortgages, and why creative finance without proper structure can destroy deals. In this episode of RealDealChat, Caleb Christopher — self-described “systems nerd” and real estate deal architect — explains how creative finance deals actually work in the real world. We go deep into subject-to transactions, wraparound mortgages, due-on-sale clauses, VA loan nuances, and why title companies often can’t (and shouldn’t) provide advisory guidance on structure. Caleb shares why a neutral third-party consultant is often necessary to protect both buyers and sellers in creative deals — and how improper underwriting or desperation can spiral into long-term damage. We also unpack scaling a boutique consultancy, why tribal knowledge kills growth, how documenting processes protects against employee turnover, and why Caleb moved from JV partnerships to flat-fee advisory. On the tech side, we dive into AI workflows, separating research chats from execution chats, agentic AI tools like Manus, and why AI is an amplifier — not a replacement. If you’re exploring creative finance, scaling a service business, or trying to balance speed with operational clarity, this episode is packed with practical insights. 🌐 Learn more: https://calebchristopher.io 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 Mentioned in this episode: book a Fit Call at RealDealCrew.com

    40 min
See All (302)

5
out of 5
80 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.

Information

You Might Also Like