REI Rookies Podcast (Real Estate Investing Rookies)

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 bedsThis 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

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 investmentThis 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 portfolioIf you've been sitting on equity and not sure what to do next, Onyi's framework will sharpen your thinking.

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 offThis 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

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 attachedThis 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

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 workThis 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

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 practiceThis 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

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

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 insteadThis 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

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 planThis 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

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 6This 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

Dru Wischhover breaks down what title insurance actually covers, the fraud patterns targeting investors, and what kills deals at the closing table.In this episode of RealDealChat, Jack Hoss sits down with Dru Wischhover, owner of a boutique title company and development firm, to pull back the curtain on one of the most misunderstood parts of real estate investing — title insurance.Dru covers:The difference between an owner's policy and a lender's policy — and why investors often skip the wrong oneWhy title insurance covers the past, not the future (and why that matters)Two real fraud cases: a deceased man's signature forged on a deed and a $275K property sold out from under an elderly widowThe $500,000 bounced cashier's check that cost Dru clients and a builder relationshipWhy rush closings are a red flag — and what to look forHow assumptions, novations, and stacked assignments actually work from the title sideWhat wholesalers get wrong about disclosure at closingThe three things every investor should do to ensure a smooth closeWhy Dru includes attorney access in his title work — and how that protects investorsHow he's expanding into Indiana and what the scale-up bottleneck taught himHis Heroes Helping Heroes nonprofit launching in 2026This episode is for:Wholesalers, flippers, and buy-and-hold investors who want to close cleanInvestors who've been burned by a deal falling apart at the tableAnyone who's ever wondered what a title company actually does for them

Daniel McDavid breaks down how to repair your credit in 4–6 months, access up to $50K at 0% interest, and fund your first real estate deal.In this episode of RealDealChat, Jack Hoss sits down with Daniel McDavid, founder of Move Mountains Funding, to break down one of the most overlooked levers in real estate — credit repair and business funding.Daniel shares the full journey:How a prayer, an Instagram post, and a $10,000 bet launched his entire businessThe 4–6 month credit repair timeline (and when it can happen in 30 days)What a trade line is and how it temporarily boosts your credit score to unlock fundingHow to access $50K–$100K at 0% interest for 12 months through business creditWhat rental arbitrage is — and why you don't need to own property to cash flow on AirbnbThe FCRA rights most consumers don't know they have — and how to use themHow to spot a credit repair scam (the Zelle/Cash App red flag)The questions you should be asking any credit repair company before you signHow Daniel's wife went from employee to tax business owner — and the identity shift that made it possibleWhy Daniel was homeless for five years and how faith drove every financial decision sinceThis episode is for:New investors who can't get funding because of their creditAnyone who's been denied and doesn't know whyEntrepreneurs ready to stop renting their future and start building itInvestors who need 0% capital to get their first deal off the ground

Brandon Cobb went from getting fired to managing $22M in land development — and breaks down exactly how he did it and what almost wiped him out.In this episode of RealDealChat, Jack Hoss sits down with Brandon Cobb, fund manager and land development coach at Learn Land Development, to unpack one of the most underutilized strategies in real estate investing.Brandon shares the full journey:How getting fired from medical device sales launched his entrepreneurial pathThe three phases of land development — entitlement, development, and buildingHis golden rule: don't buy land until all approvals are in place (and the seven-figure lesson he learned the hard way)Why 600+ units in the pipeline doesn't require a massive teamHow he pivoted from vertical integration to a strategic partner modelWhy raising private capital is easier than most investors thinkHow he uses custom GPTs for due diligence, zoning reviews, and contract analysisThe biohacking habits (cold plunge, no alcohol, Whoop tracking) that fuel his performanceHis free 8-hour Land Development 101 course at learnlanddevelopment.comThis episode is for:Investors looking to move beyond flipping and rentalsOperators with existing cash flow who want to scale into developmentAnyone curious how to raise private capital for land dealsEntrepreneurs tired of being bottlenecked by overhead and employees

Lane Kawaoka explains passive real estate investing, syndications, and how high-income earners can build wealth without being landlords.In this episode of RealDealChat, Jack Hoss sits down with Lane Kawaoka from Simple Passive Cashflow to break down how real estate investors can build wealth without managing properties themselves.Lane specializes in helping high-income professionals transition into passive real estate investing through syndications and private placements.In this conversation, we cover:What passive real estate investing actually isHow syndications work step-by-stepWho qualifies as an accredited investorWhy high-income earners struggle to scale with rentalsThe shift from active investing to passive cashflowRisks and misconceptions in syndicationsHow to evaluate deals and operatorsWhy networking and community matter at higher levelsIf you're tired of managing tenants or want to scale beyond single-family rentals, this episode will open your eyes to a different path.Timestamps:00:00 – Intro & Meet Lane Kawaoka01:30 – Lane's Background & Engineering to Investing04:00 – What Is Passive Real Estate Investing?06:45 – Active vs Passive Investing Explained09:30 – What Is a Syndication?12:15 – Accredited Investor Breakdown15:00 – Why High-Income Earners Pivot18:40 – Risks in Passive Investing21:30 – Evaluating Deals & Operators24:15 – Building Wealth Through Networking27:00 – Common Mistakes Investors Make30:30 – Final Thoughts#PassiveIncome #RealEstateInvesting #Syndications #AccreditedInvestor #PassiveRealEstate #CashflowInvesting #MultifamilyInvesting #RealEstatePodcast #InvestorMindset #RealDealChatWork With RealDealCrewIf 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 AssessmentSee how resilient your current operation actually is.→ https://assessment.realdealcrew.comBook a Fit CallIf you want to explore what a fully system-driven deal flow looks like, let's talk.→ https://realdealcrew.com/bookLIKE • SHARE • JOIN • REVIEWWebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram

In this conversation, Mark Mullen discusses the importance of treating real estate investing as a serious business. He emphasizes the role of a CFO in managing finances, the need for detailed financial tracking, and the significance of collaboration and communication in real estate projects. Mark shares insights on profit margins in fix and flipping, the value of performance-based CFO services, and the lessons learned from mistakes in business. He concludes with advice on building strong relationships and strategies for financial safety in real estate investing.TakeawaysReal estate investing requires a structured financial approach.A CFO can help track expenses and profits effectively.Detailed financial tracking is crucial for project success.Treating real estate as a business is essential for profitability.Collaboration and communication are key in real estate projects.Understanding profit margins is vital for fix and flippers.Performance-based CFO services can add value to real estate investments.Building strong relationships is critical in business.Financial safety should be a priority for investors.Mistakes in business can be costly, learning from them is essential.Chapters00:00 Introduction to CFO Services in Real Estate01:53 The Importance of Financial Structure in Real Estate04:35 Managing Multiple Real Estate Projects06:50 The Role of Technology in Real Estate Accounting09:29 Treating Real Estate as a Business12:03 Collaboration Between CFO and Real Estate Investors20:06 From Mailroom to CFO: A Journey of Growth23:05 Strategies for Real Estate Investors26:22 The Importance of Relationships in Business30:25 Lessons Learned from Mistakes31:12 Engaging with Entrepreneurs: Open Invitations34:07 Rapid Fire Insights and Closing Thoughts40:44 6-sec-outro.mp4Keywordsreal estate investing, CFO services, financial tracking, business strategy, fix and flip, performance-based contracts, investment safety, collaboration, profit margins, business relationshipsWork With RealDealCrewIf 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 AssessmentSee how resilient your current operation actually is.→ https://assessment.realdealcrew.comBook a Fit CallIf you want to explore what a fully system-driven deal flow looks like, let's talk.→ https://realdealcrew.com/bookLIKE • SHARE • JOIN • REVIEWWebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagramMentioned in this episode:book a Fit Call at RealDealCrew.comintro to RealDealCrew

In this conversation, Patrick Grimes shares his journey from a corporate engineering background to becoming a successful entrepreneur and passive investor. He discusses the importance of time freedom, the transition to passive investing, and the significance of diversification in building a resilient investment portfolio. Patrick also delves into the role of AI in enhancing business processes and the importance of non-correlated investments, particularly in healthcare. The discussion highlights the challenges and lessons learned in scaling a business and the value of partnerships in achieving financial security.TakeawaysTime freedom and location freedom are essential for a fulfilling life.The transition from engineering to entrepreneurship can be daunting but rewarding.Passive investing mastery emerged from a need for focus and education.Non-correlated investments are crucial for building a resilient portfolio.Healthcare investments are a promising niche due to their consistent demand.AI can significantly streamline business processes and reduce costs.Diversification is key to financial security and stability.Active investors should learn to partner and avoid the DIY trap.Scaling a business requires effective team dynamics and leveraging virtual assistants.Continuous learning and adaptation are vital in the ever-changing investment landscape.Chapters00:00 Introduction and Exciting Updates01:24 Life in Hawaii and Its Impact on Investing03:37 Transitioning from Engineering to Passive Investing06:11 The Importance of Focus in Business08:29 Exploring New Investment Niches11:01 Navigating AI Disruption in Investments13:32 The Value of Diversification15:48 Building Passive Income Strategies18:16 Scaling a Business and Overcoming Challenges20:17 Leveraging Virtual Assistance for Growth22:44 Using AI in Business Operations24:58 Final Thoughts and Rapid Fire Questions32:27 6-sec-outro.mp4KeywordsPassive Investing, Entrepreneurship, Non-Correlated Investments, AI in Investing, Financial Security, Diversification, Healthcare Investments, Virtual Assistants, Scaling Business, Time ManagementWork With RealDealCrewIf 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 AssessmentSee how resilient your current operation actually is.→ https://assessment.realdealcrew.comBook a Fit CallIf you want to explore what a fully system-driven deal flow looks like, let's talk.→ https://realdealcrew.com/bookLIKE • SHARE • JOIN • REVIEWWebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagramMentioned in this episode:intro to RealDealCrew

In this conversation, Michael Chang shares his journey from a successful career in investment banking on Wall Street to becoming a thriving entrepreneur in the short-term rental market. He discusses the challenges and lessons learned from his transition, including the importance of flexibility, the impact of technology, and the financial benefits of short-term rentals compared to traditional long-term investments. Michael also delves into the STR tax loophole, market saturation, and the significance of quality in real estate investments. He emphasizes the need for self-belief and the value of surrounding oneself with supportive networks in the entrepreneurial journey.TakeawaysMichael transitioned from Wall Street to short-term rentals for more flexibility.He started his rental business while still working full-time.The journey involved many small, intentional steps and learning from failures.Short-term rentals can generate significantly more cash flow than long-term rentals.The STR tax loophole offers substantial tax benefits for high-income earners.Quality properties in desirable locations can differentiate from market saturation.Government incentives encourage investment in short-term rentals.Early mistakes taught him the importance of technology and process in operations.Investing in short-term rentals can provide financial freedom and time flexibility.Surrounding oneself with a supportive network is crucial for success.Chapters00:00 From Wall Street to Short-Term Rentals00:58 The Journey of Transitioning Careers03:47 Lessons from Failed Ventures06:05 The Mechanics of Managing Properties08:36 Contrasting Long-Term and Short-Term Rentals11:02 The Tax Benefits of Short-Term Rentals13:45 Understanding the STR Tax Loophole19:46 Understanding Short-Term Rental Tax Benefits20:36 Lessons from Early Short-Term Rental Experiences21:51 Navigating the Short-Term Rental Market23:50 The Importance of Quality in Property Selection26:13 Targeting High-Income Clients for Success27:59 Regulatory Considerations in Real Estate Investment30:08 The Future of Short-Term Rentals and Tax Strategies38:30 6-sec-outro.mp4Keywordsshort-term rentals, Wall Street, real estate, investment, tax benefits, property management, Airbnb, market analysis, financial freedom, entrepreneurshipWork With RealDealCrewIf 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 AssessmentSee how resilient your current operation actually is.→ https://assessment.realdealcrew.comBook a Fit CallIf you want to explore what a fully system-driven deal flow looks like, let's talk.→ https://realdealcrew.com/bookLIKE • SHARE • JOIN • REVIEWWebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagramMentioned in this episode:book a Fit Call at RealDealCrew.comintro to RealDealCrew

In this conversation, Daniel Daly shares his journey from the automotive industry to real estate investment, focusing on international opportunities, particularly in Portugal. He discusses the advantages of the Portugal Golden Visa program, the challenges of building a network abroad, and the importance of customer experience in hospitality. Daniel emphasizes the need for effective delegation and the impact of tourism on property values in Europe. He also addresses the evolving regulations in real estate investment and the benefits of having a visa or citizenship in another country, especially for retirement.TakeawaysBringing an outside perspective can be advantageous in real estate.The first year in real estate is crucial for learning and networking.Investing in international real estate can offer better returns.The Portugal Golden Visa allows for residency through investment.Finding the right local partners is essential for success abroad.Customer experience is key in the hospitality industry.Regulations in real estate are always changing; stay informed.Effective delegation is necessary for growth in business.Tourism significantly impacts property values in Europe.Visa benefits can enhance retirement options and travel flexibility.Chapters:00:00 Introduction to Daniel Daly and His Background01:54 Transitioning from Automotive to Real Estate04:44 The Learning Curve in Real Estate07:35 Investing in International Real Estate10:03 Understanding the Portugal Golden Visa12:46 Challenges in Building a Network Abroad15:14 The Importance of Customer Experience in Hospitality17:52 Navigating Changes in Investment Regulations20:29 Managing Properties and Delegating Tasks23:18 Identifying Investment Opportunities25:55 Visa Benefits and Retirement Options in Portugal28:30 Closing Thoughts and Rapid Fire Questions33:54 outro.mp4Keywordsreal estate, international investment, Portugal Golden Visa, hospitality, property management, investment strategies, multifamily real estate, tourism, networking, customer experienceWork With RealDealCrewIf 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 AssessmentSee how resilient your current operation actually is.→ https://assessment.realdealcrew.comBook a Fit CallIf you want to explore what a fully system-driven deal flow looks like, let's talk.→ https://realdealcrew.com/bookLIKE • SHARE • JOIN • REVIEWWebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagramMentioned in this episode:intro to RealDealCrewbook a Fit Call at RealDealCrew.com

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 expenseBrian 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.techBuild smarter systems: https://realdealcrew.comWork With RealDealCrewIf 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 AssessmentSee how resilient your current operation actually is.→ https://assessment.realdealcrew.comBook a Fit CallIf you want to explore what a fully system-driven deal flow looks like, let's talk.→ https://realdealcrew.com/bookLIKE • SHARE • JOIN • REVIEWWebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagramMentioned in this episode:intro to RealDealCrewbook a Fit Call at RealDealCrew.com

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 pivotThis 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.

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 decisionsWe 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.

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 passiveDan 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.

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 startedAshley 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.

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-makingMatthew 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.

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” cultureIf you're investing in multifamily—or preparing for the next phase of this cycle—this conversation will sharpen your framework.

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.

Fernando Angelucci explains how tax-advantaged self storage, solar infrastructure, and AI-driven pricing are reshaping modern real estate returns.Full description: In this episode of RealDealChat, Fernando Angelucci, founder of Self Storage Syndicated Equities, breaks down why self storage continues to outperform—and how investors can use it to reduce taxes while building long-term wealth.Fernando explains how cost segregation, bonus depreciation, Section 179 (via solar installations), and partial asset disposition can potentially offset 50–90% of taxable income for qualifying investors. We also unpack why self storage laws differ dramatically from residential real estate, how consolidation is creating long-term opportunity, and why 65% of the industry is still owned by mom-and-pop operators.On the operational side, Fernando dives into AI-driven dynamic pricing, “good-better-best” unit positioning, rent increase optimization, and how tech upgrades can double asset value within a few years. We also discuss seller financing in tight credit markets, building portfolios for institutional exits, and why raising capital today requires storytelling—not spreadsheets.If you're exploring tax-efficient investing, passive income, or modern self storage operations, this episode delivers both strategy and tactical execution.

Kenny Bedwell explains why short-term rentals are harder today—and how data, design, and discipline still create outsized returns.In this episode of RealDealChat, Kenny Bedwell—short-term rental investor, former Citibank data analyst, and founder of STR Insights—breaks down what has actually changed in the Airbnb market over the last eight years.Kenny shares his journey from house hacking a duplex in Buffalo to owning short-term rentals across multiple states and even operating a hotel. We dive into why the “throw it on Airbnb and print money” era is over, how competition and regulation reshaped the landscape, and why data—not hype—must drive every STR decision today.This conversation covers how Kenny uses nationwide data to identify high-ROI markets most investors overlook, why regulated markets can still outperform, how to self-manage STRs without burning out, and what amenities and design choices actually move the revenue needle. Kenny also shares his most expensive mistakes, why parking and neighbors matter more than Instagram aesthetics, and how to think about guest avatars instead of generic “travelers.”If you're considering short-term rentals—or already in the game and feeling squeezed—this episode will reset your expectations and sharpen your strategy.

Nicholas Lawless shares why mindset, leadership, and time discipline matter more than tactics for entrepreneurs and real estate investors.In this episode of RealDealChat, Nicholas Lawless joins Jack for a deep, wide-ranging conversation on mindset, leadership, security, and entrepreneurship—and why most success (or failure) starts long before tactics or money enter the picture.Nick shares his unconventional journey from construction and the military to national security work at the highest levels of government, including investigations tied to January 6th and other sensitive matters, before stepping away to build multiple businesses of his own. We spend significant time unpacking mindset: imposter syndrome, taking intentional steps backward to move forward, and why many entrepreneurs sabotage themselves by refusing to delegate.We also explore why weak leadership is a real national security risk, how that same weakness shows up inside companies, and why leadership must start at home before it can work anywhere else. On the practical side, Nick explains why real estate developers lose millions to preventable security failures, how physical security outperforms camera-only setups, and why protecting people, timelines, and assets is often misunderstood as a “non-revenue expense.”This episode blends philosophy, hard-earned experience, and real-world operator lessons—covering everything from hiring executive assistants to generational wisdom, fatherhood, and building businesses that don't consume your life.

Ryan Cadwell shares why patience, cash, and realistic underwriting matter more than optimism as real estate heads toward its next reset.In this episode of RealDealChat, Ryan Cadwell, CPM of Resolute Realty, delivers a grounded, operator-level perspective on where real estate really stands heading into 2026.Ryan walks through his 18-year journey—from growing up around apartments and property management to building a vertically integrated business that includes development, construction, brokerage, and operations. We dig into why many deals are still overpriced, how interest rate cuts failed to reduce the true cost of capital, and why optimism driven by fear is putting investors at risk.This conversation covers hard-earned lessons from the 2008 crash, turnkey fallout in Indianapolis, flipping vs holding decisions, duplex development, and why positive leverage, low stress, and cash reserves now matter more than rapid growth. Ryan also explains how relationships—not listings—drive real deal flow, why patience is often the missing skill, and how automation should reduce friction without removing human judgment.If you're trying to decide whether to hold, sell, build, or wait, this episode will help you think more clearly—and more conservatively—about your next move.

Marcy Sagel explains how disciplined design decisions directly impact budget control, lease-up speed, and long-term returns in multifamily real estate.In this episode of RealDealChat, Marcy Sagel—principal of MSA Interiors—breaks down how interior design quietly determines whether a multifamily project stays on budget or spirals out of control.With nearly 30 years of experience across market-rate, student housing, senior housing, and affordable housing, Marcy explains why doing all the design work upfront is the single biggest cost-saving move an investor can make. We dive into how late-stage construction changes destroy budgets, how durable materials outperform trendy finishes, and why investors often underestimate how design affects maintenance, operations, and resident retention.Marcy also shares practical insights on paint color strategy, micro-amenities that outperform flashy features, space planning for high-traffic areas, and how design choices directly influence NOI—not just aesthetics. We explore why customization (like accent walls) can beat giveaways, how to future-proof amenity spaces, and where AI helps—and absolutely does not help—in commercial design.This is a must-listen episode for investors who want design that performs, not just looks good on day one.

Attorney and surety expert Gary Eastman explains how bonds protect real estate investors from delays, contractor failures, and costly litigation.In this episode of RealDealChat, Gary Eastman—attorney and founder of Swift Bonds—breaks down what surety bonds really are, why they exist, and when real estate investors should actually use them.Gary shares how he accidentally built a nationwide surety business after noticing a gap in how probate, construction, and licensing bonds were being handled. We dive into the three main bond categories (court bonds, contract bonds, and license & permit bonds), how bonds differ from escrow, and why they're increasingly being used on private real estate projects—not just public jobs.You'll hear real-world stories from over $1B in bonded projects, including situations where a simple problem turned into a six-figure mess—and how bonds prevented years of litigation. We also cover contractor red flags, labor shortages, supply-chain risk, AI's limits in forecasting, and why time delays—not cost overruns—are usually the real portfolio killers.This is a practical, risk-aware conversation for investors who want to scale without gambling their timeline or capital.

Erik Nordstrom and Eric Strom share how surviving the 2008 crash shaped their approach to partnerships, underwriting, and in-house property management.In this episode of RealDealChat, Erik Nordstrom and Eric Strom of Iron Ridge Capital break down what nearly two decades of investing together has taught them about real estate, relationships, and risk.We start with Erik's early exposure to apartment syndication and the decision to bet on commercial real estate just before the Great Financial Crisis. From living through 2008–2009 to swinging hammers on their first six-unit deal, Erik and Eric explain how that painful period forged discipline that still guides every deal they underwrite today.The conversation dives deep into why partnerships often fail, how they handled the awkward conversations upfront, and why trust, communication, and clearly defined roles matter more than deal structure. We also explore why they ultimately brought property management in-house, how that decision nearly doubled NOI on one property, and why most third-party managers are structurally misaligned with owners.On the operations side, they share lessons from growing to 48 employees, bootstrapping without corporate debt, navigating layoffs and pay cuts transparently, and building a culture that people choose to stay in. We wrap with a candid look at today's market cycle, distress driven by bridge debt, and why Iron Ridge is positioning aggressively for the next 12–24 months.This episode is a masterclass in patience, vertical integration, and building a real estate business that survives bad markets—not just good ones.

Dave Holman shares how buy-and-hold real estate, strong operations, and impact-driven housing can create durable wealth and thriving communities.In this episode of RealDealChat, Dave Holman—real estate investor, broker, and property manager—walks through a grounded, real-world approach to building wealth through long-term ownership and responsible operations.Dave shares how a nontraditional path—from nonprofits and entrepreneurship abroad to real estate in Maine—shaped his philosophy around housing, community, and capital. We dive into scaling from a handful of units to 360+ units owned and managed, plus 180+ units under development, while keeping a strong focus on residents, retention, and operational discipline.We also explore Dave's work housing immigrants and refugees, why many assumptions about tenants are wrong, and how impact-focused housing can still outperform financially. On the tactical side, Dave breaks down some of the best low-hanging fruit for increasing NOI—including property tax appeals, insulation upgrades, heat pumps, and utility optimization.This is a thoughtful conversation about patience, fundamentals, and why buy-and-hold real estate remains one of the most resilient paths to long-term wealth.

Mark Shuler explains why real estate success isn't about intellect or experience—it's about grit, systems, and relentless execution.In this episode of RealDealChat, Mark Shuler—architect turned multifamily syndicator—breaks down what it really takes to scale in commercial real estate.With over $600M in assets, 5,000+ doors, and 200+ employees, Mark shares how he transitioned from being a hired architect to a general partner in large value-add syndications. We dive into deep C-class renovations, workforce housing ethics, supply-chain control, in-house labor models, and why most operators get crushed when assumptions break.Mark also unpacks the current market cycle, the rise of “extend and pretend”, why distress is accelerating, and what disciplined operators are doing right now to prepare for the next acquisition window. We talk hiring mistakes, lease audits, tenant realities, war stories, and why this business rewards those who can grind through uncertainty.This is a candid, no-fluff conversation for investors who want the truth—not the Instagram version—of multifamily real estate.

Mike Zlotnik breaks down real estate market cycles, why predictability matters more than hype, and how chess-level thinking applies to investing.In this episode of RealDealChat, Mike Zlotnik returns for a deep, no-nonsense conversation on market cycles, risk, and building a resilient real estate portfolio.Mike shares his journey from political refugee and chess master to tech executive and full-time real estate fund manager. We explore how chess shaped his approach to investing, why past performance is not predictive, and how investors should adapt strategies based on where we are in the market cycle.We dive into why Mike is currently focused on industrial and open-air retail, what he calls the 2% positive spread rule (cap rate vs interest rate), and why downside protection, fixed-rate debt, and tenant credit quality matter more than chasing appreciation. Mike also explains why multifamily still has unresolved risk, how AI could be deflationary, and why diversification—across assets and time—is the most underrated strategy in investing.This episode is a masterclass in patience, discipline, and thinking several moves ahead.

Chris Prefontaine breaks down why creative real estate works in every market—and why most investors quit before the breakthrough.In this episode of RealDealChat, Chris Prefontaine returns to break down the fundamentals of creative real estate investing and why patience—not tactics—is the missing ingredient for most investors.Chris shares his journey from traditional building and brokerage to getting crushed in the 2008 crash—and how that pain forced him to rethink everything. With no credit, no cash, and no desire to rely on banks again, Chris rebuilt his business using owner financing, lease-purchase, and subject-to strategies—eventually creating what he calls the 3-Payday System: getting paid upfront, monthly, and on the backend of every deal.We dive deep into why it realistically takes 3–7 years to master any business, how unrealistic expectations sabotage investors, why drilling too many “wells” guarantees failure, and how creative real estate allows you to operate profitably in any market cycle—including COVID and today's high-rate environment.This episode is essential listening for investors tired of chasing tactics and ready to build something durable.

Colton Pace explains why most property tax bills are wrong—and how homeowners and investors can reduce expenses without upfront risk.In this episode of RealDealChat, Colton Pace, co-founder of Ownwell, breaks down one of the most overlooked wealth drains in real estate: property taxes that go unquestioned year after year.Colton shares how his experience working with a multi-billion-dollar family office revealed a massive gap between how institutions manage real estate and how everyday owners do. That insight led to Ownwell—a platform designed to help homeowners and investors optimize their largest recurring expenses, including property taxes, insurance, utilities, and refinancing.We dive into how property tax appeals actually work, why most assessments are inaccurate, and how Ownwell's contingency-only model removes downside risk. Colton also shares real stories—from retirees nearly priced out of their homes to investors receiving massive tax refunds—along with lessons on delegation, scaling teams, and where AI truly helps (and where humans are still required).If you own real estate and don't actively manage your expenses, this episode could save you real money.

After serving time in federal prison, Fuzzy Jardine rebuilt his life—and went on to build 150+ affordable homes in Hawaii using values-driven real estate.In this episode of RealDealChat, Kolaiah “Fuzzy” Jardine shares one of the most powerful real estate journeys you'll hear—rising from a troubled past and federal prison sentence to becoming a successful developer focused on affordable housing for local families in Hawaii.Fuzzy walks through the mindset shift that changed everything, why investing in education (even when it felt impossible) was the turning point, and how surrounding himself with the right mentors accelerated his growth. We break down his first creative deal, how he learned development through partnerships, and how he now builds and sells brand-new homes at prices unheard of in Hawaii.You'll also hear why leading with people before profits matters, how values create better deals, how he funds projects entirely with other people's money, and why documenting your journey attracts partners naturally.This is a masterclass in resilience, alignment, and building real wealth the right way.

Nathan Schiess explains why personal branding isn't optional for real estate investors—and why waiting until you need capital is already too late.In this episode of RealDealChat, Nathan Schiess—real estate investor turned personal branding consultant—breaks down why documenting your journey matters more than perfecting your pitch.Nathan shares his own story of building and liquidating a real estate portfolio without documenting any of it—and how that hard lesson shaped his work helping investors, agents, syndicators, and capital raisers build trust before they need it. We unpack the difference between personal brands and company brands, why repetition is necessary (not annoying), how to think about ICP and USP, and why most investors should hire this out instead of trying to DIY content.We also dive into AI, batching content, why “giving away the secret sauce” actually increases credibility, and how a strong personal brand follows you from one venture to the next—unlike a business brand that stays behind.If you ever plan to raise capital, partner on deals, or stand out in a crowded market, this episode is required listening.

Natalie Cloutier shares how she built a multimillion-dollar rental portfolio by focusing on small new builds, sweat equity, and long-term thinking.In this episode of RealDealChat, Natalie Cloutier—co-founder of The New Build Couple and author of a new book on small-scale development—breaks down how she and her husband built a $13M+ rental portfolio by starting with their own home and scaling into duplexes, triplexes, fourplexes, and sixplexes.We explore how new-build rentals can work even without large upfront capital, the power of sweat equity, and why credit unions and construction-to-permanent loans are often overlooked advantages. Natalie shares hard-earned lessons on zoning battles, infill development, dealing with neighborhood pushback, and why staying small (six units or less) often produces better cash flow with less risk.This conversation goes beyond tactics—it's about resilience, patience, and why real estate success usually takes a decade, not a year.

Cost segregation expert Erik Oliver explains why this strategy now works for small rentals—and how 100% bonus depreciation changes the game.In this episode of RealDealChat, Erik Oliver breaks down cost segregation in plain English and explains why it's no longer just for massive commercial properties.We cover how accelerated depreciation works, why bonus depreciation puts cost segregation “on steroids,” and how investors can unlock massive tax savings—even on single-family rentals. Erik also walks through common misconceptions, why most CPAs don't offer cost segregation, how depreciation recapture really works, and when this strategy doesn't make sense.You'll also hear how technology and AI are reducing study costs, what the process looks like step-by-step, and how investors can use cost segregation strategically to grow faster—without crossing IRS lines.If you own real estate and pay taxes, this episode could change how you think about depreciation forever.

Jason Hull explains why bad property managers destroy returns—and why smart investors start with the manager, not the property.In this episode of RealDealChat, Jason Hull, founder of DoorGrow and host of The DoorGrow Show, breaks down one of the most overlooked truths in real estate investing: property management—not the property—is the key to true passive income.We unpack why so many investors struggle with micromanagement, misaligned incentives, and emotional decision-making—and how most property managers end up trapped in what Jason calls the “cycle of suck.” Jason explains how elite investors flip the script by finding a great property manager first, paying them well, and letting them protect the asset.This conversation also dives into off-market deal flow through property managers, why DIY management stalls growth, how bad properties create bad tenants, and what technology and AI will (and won't) replace in property management.If you want real passive income—not a second job—this episode is required listening.

Franchise expert Adam Goldman explains how the right franchise can complement real estate investing, create deal flow, and unlock scalable systems.In this episode of RealDealChat, Adam Goldman—former franchise owner turned franchise consultant—breaks down how franchising can work alongside real estate investing to create additional income, systems, and leverage.Adam shares his journey from owning an office-cleaning franchise to placing hundreds of franchisees across dozens of industries. We discuss why SOPs and brand systems are often undervalued, how franchises can support real estate investors with capital and deal flow, and which business models are best suited for semi-absentee ownership.We also explore real estate-adjacent franchises, service businesses that generate investor leads, and why understanding your personal strengths—and weaknesses—is critical when choosing a franchise.

RealDealCrew.comWe empower real estate investors by optimizing your business processes through customized automation and system integration. From lead management to deal closure, we help you build a scalable and efficient operation. Learn more at RealDealCrew.comLIKE • SHARE • JOIN • REVIEWWebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagramSUPPORT THE SHOW!If you are new to Wealthfront, and open a Cash Account, you'll get a 0.50% APY boost for 3 months.Open an Automated Index Investing Account or Automated Bond Portfolio, you'll earn $5,000 managed for free.Get $10 and Reduce Your Business Costs by Shopping at AppSumo • https://bit.ly/reiappsumoGet $10 Towards Your First...

RealDealCrew.comWe empower real estate investors by optimizing your business processes through customized automation and system integration. From lead management to deal closure, we help you build a scalable and efficient operation. Learn more at RealDealCrew.comLIKE • SHARE • JOIN • REVIEWWebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagramSUPPORT THE SHOW!If you are new to Wealthfront, and open a Cash Account, you'll get a 0.50% APY boost for 3 months.Open an Automated Index Investing Account or Automated Bond Portfolio, you'll earn $5,000 managed for free.Get $10 and Reduce Your Business Costs by Shopping at AppSumo • https://bit.ly/reiappsumoGet $10 Towards Your First...

After a near-fatal accident put him in a coma, Nick Prefontaine rebuilt his life by learning to trust his inner voice—and that mindset shaped everything that followed.In this powerful episode of RealDealChat, Nick Prefontaine shares the life-altering story that began with a snowboarding accident, a coma, and doctors saying he might never walk, talk, or eat again.Nick breaks down the STEP System—Support, Trust, Energy, and Persistence—and how it guided his recovery, his entry into real estate, and eventually his purpose-driven work as a speaker and mentor. We explore trusting your inner voice, breaking free from fear-based advice, meditation as a performance tool, and how momentum—not motivation—creates lasting change.This episode goes far beyond real estate tactics. It's about building conviction, clarity, and confidence when the path forward isn't obvious.

Mortgage note investing is often pitched as “passive income,” but that's not the full story.In this episode of RealDealChat, Jack Hoss sits down with Jamie Bateman of Labrador Lending to explain how mortgage note investing actually works, why it's different from owning rental properties, and what investors should realistically expect before getting started.Jamie shares his journey from W-2 employee to rental owner to full-time note investor, including:The difference between performing and non-performing notesWhy banks sell mortgage debt at a discountHow investors “become the bank”The risks most gurus gloss overWhy focus and patience matter more than speedThis episode is ideal for real estate investors exploring alternatives to rentals, or anyone curious about note investing without the hype.RealDealCrew.comWe empower real estate investors by optimizing your business processes through customized automation and system integration. From lead management to deal closure, we help you build a scalable and efficient operation. Learn more at RealDealCrew.comLIKE • SHARE • JOIN • REVIEWWebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagramSUPPORT THE SHOW!If you are new to

Thomas Collins explains house hacking, multifamily investing, and how to make your assets pay for your lifestyle—starting with your first property.Full DescriptionIn this episode of RealDealChat, Jack Hoss sits down with Thomas Collins, founder of Shift Rich Academy, to break down one of the most powerful entry points into real estate investing: house hacking.Thomas shares how a single conversation at his day job sparked a mindset shift that led him from renting at $1,400/month to owning a duplex where his tenants paid nearly the entire mortgage. He explains why multifamily properties (especially duplexes, triplexes, and fourplexes) are the smartest first move for new investors—and how FHA loans make it possible with just 3.5% down.The conversation goes deep into:House hacking vs flips (and why HGTV gets it wrong)Establishing your buy box when you plan to live in the propertyUsing short-term rentals to dramatically increase cash flowCostly mistakes with tenants, licenses, and partnershipsWhy systems, virtual assistants, and AI prevent real estate from becoming another jobHow confidence explodes after the first dealWhy waiting for “perfect” kills momentumThis episode is packed with real-world lessons, beginner clarity, and systems thinking for anyone sitting on the sidelines.

Eddie Speed explains why note investing is outperforming rentals, how investors become the bank, and why seller financing is the next shift.In this episode of RealDealChat, Jack Hoss sits down with Eddie Speed, founder of NoteSchool, to break down why note investing and seller financing are rapidly outperforming traditional rental properties in today's market.Eddie explains why rising expenses, compressed cap rates, and stagnant rents are breaking the rental model—and how investors are pivoting by becoming the bank instead. He shares how landlords, realtors, and investors can transition from owning rentals that barely cash flow to holding performing notes generating double-digit returns with far fewer headaches.The conversation dives deep into:Why rentals are producing 4% while notes can produce 9–12%How seller financing creates instant liquidityTurning landlords into “mini mortgage banks”Why rate cuts don't fix rental mathHow stress-testing strategies prevents catastrophic lossesBlockchain, automation, and the future of mortgage notesWhy mentorship compresses decades of learning into monthsIf you're a real estate investor questioning your current strategy—or searching for safer, more scalable cash flow—this episode is a must-watch.

Mitchell Osmond explains why high-performing men feel powerful at work but disconnected at home—and how to rebuild marriage, health, and purpose.In this episode of RealDealChat, Jack Hoss sits down with Mitchell Osmond, founder of Dad Nation and host of the Dad Nation Podcast, for a powerful conversation on marriage, masculinity, leadership, and emotional connection.Mitchell works exclusively with high-performing, career-driven men who feel successful professionally—but disconnected, confused, or powerless at home. He breaks down why men are more medicated, divorced, and emotionally lost than ever before, and how cultural confusion around masculinity is quietly destroying marriages.This episode dives into:Why men default to “fixing” instead of listeningThe wiring differences between men and women (and why it matters)Why 70–90% of divorces are initiated by womenHow emotional disconnection—not money or cheating—ends marriagesThe “Powerful at Work, Powerless at Home” identity crisisParkinson's Law and a simple productivity system that restores focusHow clarity, community, and legacy thinking transform menWhy generational wealth is about behavior, not moneyIf you're an entrepreneur, investor, or business owner trying to win at work without losing your family, this episode will hit hard—in the best way.