Shows
Real Estate Investing with RealDealChatWhy Security Deposits Are Costing Landlords More Than They Think w/ Andrew BowenLease insurance for rental property explained: Andrew Bowen of LeaseLock breaks down how to replace deposits and protect your assets at scale.In this episode of RealDealChat, Jack Hoss sits down with Andrew Bowen, VP at LeaseLock, to break down why the security deposit model is broken and what smart operators are replacing it with.Andrew brings 30 years across rental housing, SaaS, and InsureTech. He's seen both sides of the table and pulls no punches on what most operators are getting wrong.What lease insurance actually is and how it replaces the deposit with...
2026-04-2631 min
Real Estate Investing with RealDealChatWhat Investors Decide in the First 10 Minutes W/ Scott KellyScott Kelly has helped companies raise over $5 billion. Here's what investors actually decide in the first 10 minutes of your pitch.In this episode of RealDealChat, Jack Hoss sits down with Scott Kelly, founder of Black Dog Venture Partners, to break down how entrepreneurs and real estate investors can raise capital the right way — without wasting time on the wrong investors.Scott has spent 30 years on both sides of the table, helped companies raise over $5 billion, completed three exits of his own, and built a network of 13,000 investors and 40,000 business partners. He brings the kind of di...
2026-04-2435 min
Real Estate Investing with RealDealChat48 Years of Landlording — What New Investors Get Wrong w/ Joel MillerSEO-Weighted First 150 Characters (verified): Joel Miller shares 48 years of rental property investing lessons — tenant selection, cash flow systems, and building real generational wealth.In this episode of RealDealChat, Jack Hoss sits down with Joel Miller, author of Build Real Estate Wealth: Enjoy the Journey of Rental Property Investment, for a return visit packed with hard-won landlording wisdom.Joel has been investing since 1978, flipped over 100 properties, and now runs a hard money lending operation — all while mentoring the next generation of investors, including his own son, who bought his first rental property a week after high scho...
2026-04-2242 min
Real Estate Investing with RealDealChatHe Set a Goal of 40 Units. He Ended Up with 2,700 w/ Jens NielsenJens Nielsen left a 25-year IT career and went from 40-unit goal to managing 2,700 units — here's the exact path he took to scale commercial real estate.In this episode of RealDealChat, Jack Hoss sits down with Jens Nielsen — a former IT professional turned commercial real estate investor and high-performance coach — to break down how he went from a linear 10-year plan to managing over 2,700 units across multifamily, industrial, and flex space.Jens covers:How he started with a fourplex for $115K and scaled from thereWhy he ditched single-family immediately and went straight to small multif...
2026-04-2031 min
Real Estate Investing with RealDealChatWhy the Next 3–5 Years Are the Best Ever for Notes w/ Eddie SpeedEddie Speed has closed 50,000+ note deals in 45 years — and says the next 3–5 years may be the best window for note investing he's ever seen.In this episode of RealDealChat, Jack Hoss sits down with Eddie Speed, founder of NoteSchool, for a conversation 45 years in the making. Eddie has closed over 50,000 note deals, trained thousands of investors, and watched the real estate market cycle through every imaginable condition — and he's more fired up about notes right now than at any point in his career.Topics covered include:Why the next 3–5 years could be the greatest window f...
2026-04-1834 min
Real Estate Investing with RealDealChatYou Don't Own Your Brand (Until You Do This) w/ Joey VitaleJoey Vitale reveals why most entrepreneurs don't legally own their brand — and the trademark strategy that protects everything you're building.In this episode of RealDealChat, Jack Hoss sits down with Joey Vitale, founder of Indie Law and Skybreaker, to break down two things most entrepreneurs ignore until it's too late: trademark protection and offshore staffing systems.Joey shares the frameworks that helped him scale a seven-figure trademark law firm, step away from daily operations, and launch a second company — all while working less, not more.Topics covered:Why you don't legally own your...
2026-04-1632 min
AI & Automation for Real Estate Investors – RealDealCastAnthropic's New AI Can Underwrite Your Deals (Opus 4.7 Breakdown)Anthropic just released Opus 4.7 — and real estate investors should pay attention. Jack breaks down what's changed and what it means for your business.In this episode of RealDealCast, Jack Hoss walks through the Anthropic Opus 4.7 announcement page and translates what the upgrade actually means for real estate investors, syndicators, operators, and property managers.Key upgrades covered:Why Opus 4.7 handles long, multi-step tasks better than any prior Claude modelEnhanced vision — now reads images up to 2,576px, meaning it can process scanned rent rolls, floor plans, dense financial tables, and old paper documentsState-of-the-art score on finance agen...
2026-04-1615 min
Real Estate Investing with RealDealChatWhy Your Investment Property Is Probably Underinsured w/ Michael SilvermanMichael Silverman reveals why most investment properties are underinsured — and the liability gaps that could cost investors everything.In this episode of RealDealChat, Jack Hoss sits down with Michael Silverman of Silver Lining Insurance Agency (slia.agency) — third-generation insurance broker with nearly 40 years of experience — to break down the insurance blind spots most real estate investors don't know they have.Michael covers:Why liability coverage is the #1 most overlooked protection for investorsHow building replacement costs have skyrocketed — and why outdated policies leave you exposedThe water leak detection system that saves investors thousands annually in premiums...
2026-04-1430 min
Real Estate Investing with RealDealChatTurn One House Into 28 Doors with Co-Living w/ Katrina E. RobinsonKatrina 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 us...
2026-04-1233 min
Real Estate Investing with RealDealChatFrom 50 to 270 Deals: How Virtual Assistants Did It w/ Bob-LachanceBob 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, runn...
2026-04-0832 min
Real Estate Investing with RealDealChatA Contractor Stole $104K — Here's What Kirk Built After w/ Kirk WelshKirk 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 yo...
2026-04-0627 minAI & Automation for Real Estate Investors – RealDealCastYou're Burning Claude Tokens — Here's How to StopStop burning Claude tokens — 18 hacks for real estate investors to maximize their Claude subscription without upgrading their plan.In this episode of RealDealCast, Jack Hoss breaks down 18 practical hacks for getting more out of your Claude subscription — whether you're on the $20 plan or the $200 plan.These are organized across three tiers:Tier 1 — Foundational habits: start fresh conversations, avoid pasting full documents, write precise prompts, use bullet points, ask for shorter outputs, and use pre-written templatesTier 2 — Smarter workflows: break big projects into phases, build a context seed file, compress deal data before pasting, use Claude for one...
2026-04-0614 minReal Estate Investing with RealDealChatNearshore vs Offshore Talent: What Actually Works w/ Brian SamsonBrian 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 n...
2026-03-0728 min
Real Estate Investing with RealDealChatWhy Most Real Estate Investors Plateau with John DonnellyJohn 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...
2026-03-0544 min
Real Estate Investing with RealDealChatWhy 82% of Homeowners Regret Their Purchase with Kim CostaKim 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 contentW...
2026-03-0333 min
Real Estate Investing with RealDealChatHow to Increase Airbnb Revenue 23% (Without More Units) w/ Dan RiversDan 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...
2026-03-0136 minAI & Automation for Real Estate Investors – RealDealCastReal Estate Investing: Respond in 60 Seconds or Lose $20KSpeed to lead in real estate investing can mean the difference between closing a $20K deal or losing it in 5 minutes.In this episode of RealDealCast, Jack Hoss breaks down why speed to lead in real estate investing is the difference between winning and losing deals.Leads are 21x more likely to convert when contacted within five minutes versus thirty. You’re 100x more likely to connect in the first five minutes than waiting half an hour. And responding within 60 seconds can increase conversion by nearly 400%.If you’re in real estate investing, that...
2026-02-2504 min
Real Estate Investing with RealDealChatSubject-To Real Estate Done Right with Caleb ChristopherCaleb 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 o...
2026-02-2140 min
Real Estate Investing with RealDealChatHow Self Storage Can Offset 50–90% of Your Tax Bill with Fernando AngelucciFernando 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 c...
2026-02-1941 min
Real Estate Investing with RealDealChatShort-Term Rentals Aren’t Easy Anymore—Here’s What Still Works with Kenny BedwellKenny 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 t...
2026-02-1746 min
AI & Automation for Real Estate Investors – RealDealCastAI Won’t Fix This: The Real Estate Investor Mindset Problem w/ Dr. Noah St. JohnReal estate investing success isn’t just strategy—it’s mindset. Dr. Noah St. John explains the hidden friction limiting investors.In this episode of RealDealCast, Jack Hoss sits down with Dr. Noah St. John to discuss why so many professionals in real estate investing hit invisible revenue ceilings.Dr. Noah breaks down the concept of hidden friction — the internal resistance that keeps entrepreneurs stuck at six figures when they’re capable of seven or eight.You’ll learn:The difference between inner game and outer game in real estate investingWhy 90% of success come...
2026-02-1637 min
Real Estate Investing with RealDealChatWhy Weak Leadership Is the Real Risk to Entrepreneurs with Nicholas LawlessNicholas 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 sp...
2026-02-1546 min
Real Estate Investing with RealDealChatWhy Patience Beats Optimism in Real Estate with Ryan CadwellRyan 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, a Partner at Resolute RDM, 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 wh...
2026-02-1336 min
Real Estate Investing with RealDealChatWhy Design Mistakes Kill ROI in Multifamily with Marcy SagelMarcy 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 outp...
2026-02-1132 min
Real Estate Investing with RealDealChatThe Hidden Risk in Construction Projects (And How to Eliminate It) w/ Gary EastmanAttorney 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...
2026-02-0929 min
Real Estate Investing with RealDealChatWhy Partnerships Make or Break Real Estate Investing with Erik Nordstrom and Eric StromErik 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 peri...
2026-02-0736 min
Real Estate Investing with RealDealChatBuilding Wealth While Building Communities with Dave HolmanDave 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 resid...
2026-02-0534 minAI & Automation for Real Estate Investors – RealDealCastAI for Real Estate: Claude Opus 4.6 Just Changed EverythingAI for real estate just took a major leap. Claude Opus 4.6 beats every other model at complex work tasks—here’s what it means for investors.In this episode of RealDealCast, Jack Hoss breaks down AI for real estate using the newly released Claude Opus 4.6, the first AI model to outperform competitors on million-dollar work tasks.Claude Opus 4.6 introduces a 1 million token context window, improved agentic reasoning, stronger financial analysis, and better reliability across long, complex workflows. For real estate investors, this unlocks entirely new use cases.Jack covers:What makes Claude Opus...
2026-02-0513 min
Real Estate Investing with RealDealChatWhy Grit Beats Talent in Multifamily Real Estate with Mark ShulerMark 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...
2026-02-0339 min
Real Estate Investing with RealDealChatInvest Like a Chess Master: Market Cycles & Predictable Returns with Mike ZlotnikMike 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.
2026-02-0141 min
Real Estate Investing with RealDealChatWhy Creative Real Estate Wins in Any Market with Chris PrefontaineChris 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 subj...
2026-01-3028 min
Real Estate Investing with RealDealChatMost People Overpay Property Taxes—Here’s How to Fix It with Colton PaceColton 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, incl...
2026-01-2831 min
Real Estate Investing with RealDealChatFrom Prison to Building 150 Homes: The Pono Way with Kolaiah Fuzzy JardineAfter 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 ment...
2026-01-2636 min
Real Estate Investing with RealDealChatWhy Every Real Estate Investor Needs a Personal Brand with Nathan SchiessNathan 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...
2026-01-2439 min
Real Estate Investing with RealDealChatBuilding Rentals from the Ground Up with Natalie CloutierNatalie 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 over...
2026-01-2237 min
Real Estate Investing with RealDealChat100% Bonus Depreciation Is Back: What Real Estate Investors Need to Know | Erik OliverCost 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 doe...
2026-01-2036 min
Real Estate Investing with RealDealChatWhy Property Management Is the Real Path to Passive Income with Jason HullJason 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 scr...
2026-01-1837 min
Real Estate Investing with RealDealChatFranchising as a Real Estate Multiplier with Adam GoldmanFranchise 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...
2026-01-1630 min
Real Estate Investing with RealDealChatAnswer the Phone: How Brian Truman Built a Multifamily Business on RelationshipsOne answered phone call launched Brian Truman into multifamily real estate—and built a career powered by relationships, not transactions.In this episode of RealDealChat, Brian Truman shares the unlikely origin story that launched his multifamily career just weeks after getting his real estate license—starting with a Saturday night phone call, a last-minute 1031 exchange, and a connection that changed everything.Brian breaks down why commercial real estate is a relationship business, how a small group of repeat clients can create massive leverage, and what he’s seeing right now in multifamily markets—from emerging tertiary...
2026-01-1436 min
Real Estate Investing with RealDealChatThe Great Tax Escape: How Allen Lomax Rebuilt Wealth After Losing EverythingAfter losing everything in the 2008 crash, Allen Lomax rebuilt his life by rethinking wealth, taxes, and trust—and created The Great Tax Escape.In this episode of RealDealChat, Allen Lomax shares a deeply personal story of loss, reinvention, and clarity after the 2008 financial crash wiped out everything he had built.We explore why high-income professionals often feel trapped despite success, how taxes quietly erode wealth, and why working harder inside a broken system rarely leads to freedom. Allen breaks down his six-phase framework for becoming a capital allocator—covering trusted networks, due diligence, infrastructure, tax stra...
2026-01-1234 min
Real Estate Investing with RealDealChatTrust the Voice: How Nick Prefontaine Turned Trauma Into PurposeAfter 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...
2026-01-1035 min
Real Estate Investing with RealDealChatWhy Smart Investors Are Becoming the Bank | Eddie SpeedEddie 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 bare...
2026-01-0438 min
Real Estate Investing with RealDealChatFranchising, Real Estate & AI: What Investors Miss | Giuseppe GrammaticoGiuseppe Grammatico explains franchising, AI automation, and how real estate investors use franchises to build predictable cash flow and scale smarter.Full DescriptionIn this episode of RealDealChat, Jack Hoss sits down with Giuseppe Grammatico, franchise consultant and founder of GG The Franchise Guide, to break down how franchising intersects with real estate investing, cash flow, and AI-powered operations.Giuseppe shares his journey from Wall Street to entrepreneurship, why franchising is often misunderstood, and how “business-in-a-box” models help investors shortcut years of trial and error. He explains how real estate investors can leverage fran...
2025-12-2939 min
Real Estate Investing with RealDealChatHow to Create Your Own Real Estate Market | Jose BerlangaJose Berlanga explains how he created his own real estate market, why focus beats growth, and the costly mistakes developers make chasing trends.In this episode of RealDealChat, Jack Hoss sits down with Jose Berlanga, a veteran real estate developer and entrepreneur, to break down how he created demand where none existed—and why focus, patience, and clarity matter more than chasing hot markets.Jose shares how he started developing inner-city Houston neighborhoods when they were considered “unbuildable,” why fear actually guided his best decisions, and how saturating a small area with consistent product helped him es...
2025-12-2733 min
Real Estate Investing with RealDealChatGold, Silver & the Dollar Collapse | David Morgan ExplainsDavid Morgan explains gold, silver, real estate, and why the dollar is losing trust—plus how investors protect wealth when the monetary system breaks.In this episode of RealDealChat, Jack Hoss sits down with David Morgan, founder of The Morgan Report and one of the most respected analysts in precious metals, to unpack what’s really happening inside the global monetary system.David shares how his fascination with money started as a child noticing the difference between silver coins and debased currency, and how that curiosity led to more than four decades analyzing markets, banking syst...
2025-12-2332 min
Real Estate Investing with RealDealChatBuying a Business vs Real Estate | David C. Barnett ExplainsDavid C. Barnett breaks down buying small businesses vs real estate, the risks investors overlook, and how to build resilient, cash-flowing companies.In this episode of RealDealChat, Jack Hoss sits down with David C. Barnett, author of The Business Fortress and one of the most respected voices in small business acquisition, to unpack the real differences between buying businesses and investing in real estate.David shares his journey from business brokerage to banking to building a global advisory firm helping buyers and sellers avoid catastrophic mistakes. He explains why business brokerage is fundamentally broken, how...
2025-12-2139 min
Real Estate Investing with RealDealChatHow Brent Kesler Paid Off $1M in Debt Using Infinite BankingBrent Kesler explains infinite banking, how he paid off nearly $1M in debt, and why the wealthy recycle money using the Money Multiplier method.In this episode of RealDealChat, Jack Hoss welcomes back Brent Kesler, founder of The Money Multiplier, to break down one of the most misunderstood wealth strategies in real estate and investing: infinite banking.Brent shares how he and his wife eliminated $984,711 of third-party debt in just 39 months—without changing cash flow, working harder, or taking on more risk. He explains how specially designed whole life policies allow investors to recycle and re...
2025-12-1940 minReal Estate Investing with RealDealChatBuy Rental Properties with NO Money Down | Martine RichardsonMartine Richardson explains how to buy rental properties with no money down, use private lenders, negotiate smarter, and build cash flow for freedom.In this episode of RealDealChat, Jack Hoss sits down with Martine Richardson, real estate investor, lender strategist, and coach, to break down how everyday investors can buy rental properties with no money down—even in today’s market.Martine shares her journey from getting fired at Fannie Mae and having her car repossessed to building long-term freedom through rental real estate. She explains how wholesaling led her to rentals, why private lenders are...
2025-12-1734 min
Real Estate Investing with RealDealChatWhy Most Investors Lose Deals in Follow-Up | Paul do CampoPaul do Campo explains why real estate investors lose deals in follow-up, how value-based messaging works, and why human connection beats automation alone.In this episode of RealDealChat, Jack Hoss sits down with Paul do Campo, founder of REI Omni Drip, to break down one of the most overlooked profit centers in real estate investing: follow-up.Paul explains why most investors overspend on lead generation while leaving massive money trapped inside their CRM. He shares how value-based follow-up, storytelling, and multichannel communication (email, SMS, and direct mail) dramatically increase seller responses—without sounding salesy or sp...
2025-12-1529 min
Real Estate Investing with RealDealChatRealDealCast: Top 5 Tools to Manage Rentals Remotely (Save Hours Every Week)Jack Hoss shares the top 5 tools real estate investors use to manage rentals remotely—covering cameras, smart locks, software, and automation.In this episode of RealDealCast, Jack Hoss reveals his top 5 tech tools for managing rental properties remotely. These are the exact systems he uses daily to monitor properties, communicate with tenants, and save hours every week.From Blink cameras and smart Wi-Fi door locks to Asana, TurboTenant, and his own RealDealCrew platform, Jack explains how each tool helps him manage rentals efficiently — even in rural areas or during harsh winter months.You’ll lea...
2025-12-1007 minAI & Automation for Real Estate Investors – RealDealCastTop 5 Tools to Manage Rentals Remotely (Save Hours Every Week)In this episode of RealDealCast, Jack Hoss reveals his top 5 tech tools for managing rental properties remotely. These are the exact systems he uses daily to monitor properties, communicate with tenants, and save hours every week.From Blink cameras and smart Wi-Fi door locks to Asana, TurboTenant, and his own RealDealCrew platform, Jack explains how each tool helps him manage rentals efficiently — even in rural areas or during harsh winter months.You’ll learn:How to use Blink cameras for property oversight and securityWhy smart locks make tenant access safer and simplerHow to manage main...
2025-12-1008 min
Real Estate Investing with RealDealChatThe Landscaping Secrets That Sell Houses Faster | Steve GriggsLandscape expert Steve Griggs reveals the curb-appeal upgrades that help real estate investors sell faster, boost value, and win emotional buyers.In this episode of RealDealChat, Jack Hoss sits down with Steve Griggs, award-winning landscape designer and founder of Steve Griggs Design, to uncover the most overlooked value-add in real estate: landscaping.Steve explains why curb appeal is the first showing, how the wrong trees and bushes can kill deals, and how investors can dramatically increase perceived value with surprisingly low-cost upgrades. From greening up the lawn to using proper lighting, to designing outdoor “living ro...
2025-12-0532 min
Real Estate Investing with RealDealChatGo Bigger Sooner | Ashley Garner on Scaling Multifamily FastAshley Garner shares how he scaled from duplexes to 196-unit acquisitions, overcame fear, and built a multifamily business powered by outsourcing and relationships.In this episode of RealDealChat, Jack Hoss interviews Ashley Garner of ABG Multifamily, who reveals how he went from flipping student rentals with his father to buying large multifamily properties — including his most recent 196-unit acquisition.Ashley explains why “go bigger sooner” has become his core philosophy, how fear and past failures shaped his decision-making, and why outsourcing has been the key to unlocking scale. He breaks down exactly how he sources deals...
2025-11-2733 min
Real Estate Investing with RealDealChatFrom NFL Sidelines to Beachfront Real Estate | Brooke Kromer’s JourneyFormer sports broadcaster Brooke Kromer reveals how she built a thriving luxury real estate business on Florida’s 30A, helping athletes invest wisely.In this episode of RealDealChat, Jack Hoss interviews Brooke Kromer, founder of Kromer Collective, who shares her journey from NFL sidelines to Florida’s luxury 30A coast.Brooke discusses how she transitioned from sports broadcasting into real estate, built a powerhouse all-women team, and discovered her niche helping NFL athletes and coaches invest in high-return beachfront properties.She explains how storytelling, market mastery, and consistency built her brand — and why emotio...
2025-11-1331 min
Real Estate Investing with RealDealChatDiscover Your Investor DNA | Joey Mure on Wealth Without Wall StreetJoey Mure from Wealth Without Wall Street shares how to discover your Investor DNA, create passive income, and achieve financial freedom without Wall Street.In this episode of RealDealChat, Jack Hoss sits down with Joey Mure, co-founder of Wealth Without Wall Street, to uncover how investors can design financial freedom through intentional strategy and self-awareness.Joey explains the concept of Investor DNA — a framework that helps entrepreneurs and real estate investors align their personality, values, and goals with the right investment vehicle. He also reveals how to calculate your Financial Freedom Score, avoid shiny-object syndrome, an...
2025-11-0832 min
Real Estate Investing with RealDealChatMindset, Massive Action & Multifamily Freedom | Rod KhleifRod Khleif reveals how to build wealth, overcome fear, and create lasting success through mindset, gratitude, and massive action in real estate.In this episode of RealDealChat, Jack Hoss sits down with Rod Khleif, multifamily investor, mindset coach, and host of the Lifetime Cashflow podcast. Rod shares how he built a $50M real estate portfolio, lost it all during the 2008 crash, and rebuilt his empire using the same principles he now teaches to thousands of students worldwide.Rod explains the mindset it takes to succeed in real estate — from goal setting and focus to facing fe...
2025-11-0632 min
Real Estate Investing with RealDealChatTurning Rooftops into Revenue | Dave Riess on Commercial Solar InvestingDave Riess explains how commercial property owners can turn rooftops into revenue using WonderPower’s solar systems to increase NOI and hedge energy costs.In this episode of RealDealChat, Jack Hoss sits down with Dave Riess, CEO and co-founder of WonderPower (WunderPower.com), to discuss how commercial real estate owners can generate new income and protect against rising electricity costs using rooftop solar.Dave shares his journey from electrical engineer to energy entrepreneur and breaks down why commercial solar is one of the most underutilized opportunities in real estate. He explains how WonderPower helps landlords le...
2025-10-3030 min
Real Estate Investing with RealDealChatRealDealCast: Why I’m Rebuilding My Real Estate Websites from ScratchJack Hoss reveals his new plan to rebuild his real estate websites using funnels, automation, and smarter SEO to save time and close more deals.YouTube Video at: https://youtu.be/Hco058Q4GY4In this episode of RealDealCast, Jack Hoss breaks down his complete plan to rebuild and streamline his real estate web presence for better lead generation and automation.After seeing a drop in search rankings, Jack realized that traditional SEO and cookie-cutter real estate sites no longer work. Instead, he’s shifting to a three-part strategy that focuses on authority, fu...
2025-10-2908 minAI & Automation for Real Estate Investors – RealDealCastWhy I’m Rebuilding My Real Estate Websites from ScratchJack Hoss reveals his new plan to rebuild his real estate websites using funnels, automation, and smarter SEO to save time and close more deals.In this episode of RealDealCast, Jack Hoss breaks down his complete plan to rebuild and streamline his real estate web presence for better lead generation and automation.After seeing a drop in search rankings, Jack realized that traditional SEO and cookie-cutter real estate sites no longer work. Instead, he’s shifting to a three-part strategy that focuses on authority, funnels, and full integration with his deal flow system.Yo...
2025-10-2909 min
Real Estate Investing with RealDealChatMastering Negotiation in Real Estate & Life | Robin Kencel’s Proven StrategiesRobin Kencel shares powerful negotiation strategies from her luxury real estate career, teaching how mindset, rhythm, and empathy drive better deals.In this episode of RealDealChat, Jack Hoss sits down with Robin Kencel, top Greenwich, CT real estate agent, ballroom dancer, and negotiation coach, to explore what it takes to master negotiation — in business, relationships, and life.Robin shares insights from her decades in high-end real estate and reveals how emotional intelligence, observation, and consistency can transform even the most difficult deals. She discusses the psychology of luxury clients, the importance of communication tempo, and ho...
2025-10-2824 min
Real Estate Investing with RealDealChatBuilding Wealth with Flex Space & Land Development | Alec McElhhinyAlec McElhhiny shares how he scaled from house hacking a duplex to developing high-profit flex spaces through LandPlay.com and creative land deals.In this episode of RealDealChat, Jack Hoss sits down with Alec McElhhiny, founder of LandPlay.com, to discuss how he went from an actuary crunching numbers to a real estate developer building niche flex space projects across Texas.Alec breaks down the math behind wealth-building through real estate, why flex space is booming, and how to find undervalued land that performs in any market. He also explains the “riches in the niches” prin...
2025-10-2625 min
Real Estate Investing with RealDealChat35 Years in Real Estate: Debbi DiMaggio on Mindset, Authenticity & AIDebbi DiMaggio shares her 35-year real-estate journey, mindset strategies, and how AI & authenticity help agents and investors thrive in any market.In this episode of RealDealChat, Jack Hoss sits down with Debbi DiMaggio — luxury real-estate icon, author, speaker, and coach at CoachWithDebbi.com — to unpack the habits, mindset, and authenticity that built her 35-year career.Debbi reveals how she launched a brokerage during the 2009 recession, built lasting client relationships through transparency, and now teaches agents and investors how to create freedom using systems, collaboration, and AI.You’ll learn why mindset beats the market...
2025-10-2332 minAI & Automation for Real Estate Investors – RealDealCastComparing Vibe Coding Tools: Which AI Builder Actually Works?Jack Hoss compares the top AI vibe coding tools—V0, Bolt, Replit, and Lovable—to find the fastest, easiest way to build real estate funnels.In this RealDealCast episode, Jack Hoss tests four of the most talked-about AI website-building platforms — V0, Bolt, Replit, and Lovable — to see which one actually delivers the best results.He gives each platform the same prompt and compares the output, layout, and usability when creating a simple real estate funnel page. You’ll discover which AI coding tools save time, where they fall short, and how real estate investors can leverage t...
2025-10-2208 min
Real Estate Investing with RealDealChatRealDealCast: Comparing Vibe Coding Tools: Which AI Builder Actually Works?Jack Hoss compares the top AI vibe coding tools—V0, Bolt, Replit, and Lovable—to find the fastest, easiest way to build real estate funnels.In this RealDealCast episode, Jack Hoss tests four of the most talked-about AI website-building platforms — V0, Bolt, Replit, and Lovable — to see which one actually delivers the best results.He gives each platform the same prompt and compares the output, layout, and usability when creating a simple real estate funnel page. You’ll discover which AI coding tools save time, where they fall short, and how real estate investors can leverage t...
2025-10-2208 min
Real Estate Investing with RealDealChatHOA Horror Stories & Homeowner Rights Explained | Attorney Luke CarlsonAttorney Luke Carlson explains how homeowners and investors can protect themselves from bad HOAs, understand their rights, and turn risk into opportunity.In this episode of RealDealChat, Jack Hoss sits down with Luke Carlson, founding attorney of LS Carlson Law and author of The Homeowner’s Guide to Defending Against Bad HOAs, to uncover what every real estate investor and homeowner needs to know about HOA law.Luke shares how he became one of the nation’s leading voices for homeowner rights, the psychology behind “bad boards,” and how to protect yourself when an HOA turns ro...
2025-10-2131 min
Real Estate Investing with RealDealChatFrom Wholesaling Inc. to Joe Homebuyer | Cody Hofhine on Scaling Real EstateCody Hofhine shares how to build a 7-figure wholesaling business, lead better teams, and buy back your time through delegation, systems, and mindset.In this episode of RealDealChat, Jack sits down with Cody Hofhine, co-founder of Joe Homebuyer and former leader of Wholesaling Inc., to talk about how to grow a real estate business that gives you time freedom — not just financial success.Cody breaks down how leadership, mindset, and systems are the real multipliers in real estate. He reveals how he went from working 80-hour weeks to scaling a nationwide franchise, why most investors lo...
2025-10-1941 min
Real Estate Investing with RealDealChatBookkeeping for Real Estate Investors: Avoid Costly Mistakes | Max EmoryMax Emory shares how real estate investors can simplify bookkeeping, avoid IRS headaches, and create “decision-ready” financials to grow their profits.In this episode of RealDealChat, Jack Hoss sits down with Max Emory, founder of Time Capital Bookkeeping, to discuss how real estate investors can master their numbers, avoid tax-time chaos, and make smarter decisions using clean, actionable financials.Max started as a real estate investor and Marine Corps officer, scaled to 25 units, and then built a bookkeeping firm focused exclusively on investors. His team helps clients eliminate messy books, create clear KPIs, and turn data...
2025-10-1630 min
Real Estate Investing with RealDealChatGlobal Investing 101: Real Estate, Citizenship & Diversification | Ladislas MauriceLadislas Maurice, “The Wandering Investor,” shares how to build global freedom through international real estate, second passports, and frontier markets.In this episode of RealDealChat, Jack sits down with Ladislas Maurice, founder of The Wandering Investor, to discuss the power of international investing and how real estate can become your ticket to global diversification, second citizenship, and long-term financial freedom.Ladislas shares his journey from Nestlé executive in Africa to full-time investor traveling the world, buying real estate in frontier markets, and helping clients unlock second residencies and passports through smart investments.Here’s what...
2025-10-1429 min
Real Estate Investing with RealDealChatFrom Real Estate to Franchising: Kim Daly on Building Scalable WealthFranchise expert Kim Daly explains how real estate investors can build scalable, semi-active businesses that create wealth, freedom, and long-term cash flow.In this episode of RealDealChat, Jack sits down with Kim Daly, founder of The Daly Coach and one of the top franchise consultants in the U.S., to talk about how real estate investors can use franchising to diversify their portfolios and create predictable, scalable income streams.Kim breaks down the “semi-active investor” model, explains why franchising is the bridge between entrepreneurship and investing, and shares how she’s helped hundreds of people replac...
2025-10-1241 min
Real Estate Investing with RealDealChatCost Segregation for Real Estate Investors | Save Thousands in Taxes with Gian PazziaLearn how cost segregation helps real estate investors save thousands in taxes. In this video, Gian Pazzia of KBKG breaks down how bonus depreciation, 1031 exchanges, and other real estate tax strategies can accelerate your wealth-building plan.In this episode of RealDealChat, Jack Hoss interviews Gian Pazzia, CCSP and President of KBKG — creators of CostSegregation.com — to uncover how investors use cost segregation studies to maximize deductions, reduce taxable income, and boost passive income from real estate.They cover when cost segregation makes sense, how to combine it with bonus depreciation, and why 1031 exchanges are still one...
2025-10-0932 min
Real Estate Investing with RealDealChatCPA Reveals Top Tax Mistakes Real Estate Investors Make | George DimovGeorge Dimov, CPA, shares the biggest tax mistakes real estate investors make, why proactive planning matters, and how to build smarter portfolios.In this episode of RealDealChat, Jack sits down with George Dimov, CPA and founder of DimovTax.com, to discuss proactive tax planning, common mistakes investors make, and why accounting + real estate go hand in hand.George shares his journey from immigrant beginnings to building a tax practice that serves thousands of clients nationwide. He explains why he invests heavily in real estate himself, how tax strategies like cost segregation and 1031 exchanges really work...
2025-10-0737 min
Real Estate Investing with RealDealChatBreaking Bad House & 400+ Homes Sold | David Christensen’s JourneyDavid Christensen shares how storytelling, mindset, and authenticity helped him sell 400+ homes, including the Breaking Bad house, and rebuild his life.In this episode of RealDealChat, Jack sits down with David Christensen (DavidChristensen.com) to discuss his extraordinary journey—from managing platinum-selling musicians and even working on Titanic research dives, to becoming a nationally recognized luxury real estate agent.David opens up about his path through addiction and recovery, and how mindset, authenticity, and service-first leadership transformed his career. He explains how storytelling is the secret weapon in real estate, why emotions drive home buying de...
2025-10-0229 min
Real Estate Investing with RealDealChatFrom Fourplex to Boutique Hotels: Gideon Spencer’s $6M PlaybookGideon Spencer shares how he scaled from a cash-flowing fourplex to $6M in boutique hotels using automation, creative financing, and the mentor flywheel.In this episode of RealDealChat, Jack sits down with Gideon Spencer, real estate investor and founder of a new boutique hotel community, to discuss how he scaled from a fourplex short-term rental to multi-million-dollar boutique hotels in just two years.Gideon shares his origin story in tech, the family health crisis that fueled his drive for automated wealth, and how he uses systems, teams, and creative financing to scale fast. He also...
2025-09-3038 minAI & Automation for Real Estate Investors – RealDealCastClaude Sonnet 4.5: What Real Estate Investors Need to KnowClaude Sonnet 4.5 brings powerful AI agents, coding tools, and automation upgrades—here’s how real estate investors can use them to save time.In this episode of RealDealCast, Jack Hoss breaks down Anthropic’s release of Claude Sonnet 4.5 and what it means for real estate professionals.From AI agents that can run tasks for 30+ hours straight to improved coding, automation, and Chrome extensions, this update is a game-changer. Jack explains how these tools compare to ChatGPT and Gemini, and more importantly, how investors can use them to cut busy work and focus on building wealth.Y...
2025-09-2913 min
Real Estate Investing with RealDealChatRealDealCast: Claude Sonnet 4.5: What Real Estate Investors Need to KnowClaude Sonnet 4.5 brings powerful AI agents, coding tools, and automation upgrades—here’s how real estate investors can use them to save time.In this episode of RealDealCast, Jack Hoss breaks down Anthropic’s release of Claude Sonnet 4.5 and what it means for real estate professionals.From AI agents that can run tasks for 30+ hours straight to improved coding, automation, and Chrome extensions, this update is a game-changer. Jack explains how these tools compare to ChatGPT and Gemini, and more importantly, how investors can use them to cut busy work and focus on building wealth.Y...
2025-09-2913 min
Real Estate Investing with RealDealChatFrom BRRRRs to 1,000+ Units Managed: Mark Ainley’s JourneyMark Ainley shares his journey from BRRRRs to running GC Realty, scaling property management in Chicago, and lessons from 20+ years in real estate.In this episode of RealDealChat, Jack sits down with Mark Ainley, co-founder of GC Realty & Development, co-host of Straight Up Chicago Investor Podcast, and long-time property manager and investor.Mark shares how he transitioned from house hacking and BRRRR deals to running one of Chicago’s largest property management firms. He explains why property management is often overlooked, how to avoid common investor mistakes, and why focus and systems (like EOS) have be...
2025-09-2838 min
Real Estate Investing with RealDealChatWhy “Passive Investors” Fail | Shawn Griffith on Risk, Homework & MultifamilyShawn Griffith of Kraft Capital explains why no investor should ever be passive, how to underwrite risk, and why multifamily is a long-term wealth game.In this episode of RealDealChat, Jack sits down with Shawn Griffith, managing partner at Kraft Capital Investments, to discuss the reality of multifamily investing, the dangers of being a “passive investor,” and why risk management is the cornerstone of long-term success.Shawn shares his journey from his first LP deal that tripled investor money, to building Kraft Capital with partners and launching a new flex fund. He also explains why sett...
2025-09-2529 minAI & Automation for Real Estate Investors – RealDealCastHow I Use Google’s Nano Banana AI to Save Hours in Real EstateDiscover time-saving AI tools and tech tips for real estate investors in this episode of RealDealCast. From enhancing thumbnails to generating professional headshots, Jack Hoss explores Google’s Nano Banana AI and other automation tools that can save investors valuable time.In this solo session, Jack shares real-world use cases—improving podcast thumbnails, designing hero banners, cleaning up headshots, and testing AI-generated graphics. You’ll see where AI shines, where it struggles, and how investors can leverage these tools to focus on growing their business instead of getting stuck in busy work.Whether you’re new to A...
2025-09-2509 min
Real Estate Investing with RealDealChatRealDealCast: How I Use Google’s Nano Banana AI to Save Hours in Real EstateDiscover time-saving AI tools and tech tips for real estate investors in this episode of RealDealCast. From enhancing thumbnails to generating professional headshots, Jack Hoss explores Google’s Nano Banana AI and other automation tools that can save investors valuable time.In this solo session, Jack shares real-world use cases—improving podcast thumbnails, designing hero banners, cleaning up headshots, and testing AI-generated graphics. You’ll see where AI shines, where it struggles, and how investors can leverage these tools to focus on growing their business instead of getting stuck in busy work.Whether you’re new to A...
2025-09-2509 min
Real Estate Investing with RealDealChatHow to Use Your IRA to Invest in Real Estate & Alternatives | Henry YoshidaHenry Yoshida of Rocket Dollar explains how to use IRAs for real estate, crypto, and private deals—unlocking $18T in retirement funds for alternatives.In this episode of RealDealChat, Jack sits down with Henry Yoshida, co-founder & CEO of Rocket Dollar (a subsidiary of Retired.com), to explore how investors can unlock the power of retirement accounts for real estate, crypto, and private investments.Henry shares his journey from financial advisor to wealth-tech entrepreneur, building platforms that custody over $12B in assets. He explains why traditional advisors rarely mention self-directed IRAs, how Rocket Dollar makes alternative in...
2025-09-2337 min
Real Estate Investing with RealDealChatUnlock $250K in 0% Business Credit | Patrick PychynskiPatrick Pychynski reveals how to access $50K–$250K in 0% business credit, avoid high-interest traps, and become bankable for long-term success.In this episode of RealDealChat, Jack sits down with Patrick Pychynski, founder of StackingSuccess.com, to discuss how entrepreneurs and real estate investors can unlock business funding the right way.Patrick shares his journey from the U.S. Marine Corps to building businesses, struggling with cash flow, and ultimately mastering the art of business credit. He explains how his team helps investors access 0% interest funding while building a truly “bankable” business that attracts long-term financing.H...
2025-09-2136 min
Real Estate Investing with RealDealChatProperty Management, Permits & Profits in Chicago | Michael RootMichael Root shares how he builds value in Chicago multifamily, streamlines property management, and uses in-house contracting to boost efficiency.In this episode of RealDealChat, Jack sits down with Michael Root, co-founder of Root Property Group (RootPG.com), to discuss property management, multifamily acquisitions, and why Chicago remains both a challenging and rewarding market.Michael shares how his team handles everything from general contracting to property management in-house, which helps reduce costs, improve communication, and streamline renovations.Key takeaways from this conversation include:Why clear communication is the #1 challenge in property managementHow...
2025-09-1818 min
Real Estate Investing with RealDealChatInvesting Overseas & Expat Wealth Strategies | Mikkel ThorupMikkel Thorup shares how he built an 8-figure global real estate portfolio, lives in 9 countries, and helps investors create offshore wealth strategies.In this episode of RealDealChat, Jack sits down with Mikkel Thorup, host of the Expat Money Show and founder of ExpatMoney.comMikkel shares his inspiring journey from being labeled with a “learning disability” and dropping out of school at 15, to traveling to 120+ countries, living in 9, and building an 8-figure international real estate portfolio.We cover:How to invest in pre-construction projects overseas for 30–50% appreciationWhy he prefers cash-based, expat-friendly markets like P...
2025-09-1635 min
Real Estate Investing with RealDealChatFrom Hulu to Real Estate Success: Dedric & Krystal Polite’s StoryDedric & Krystal Polite share how they built a real estate empire, landed a Hulu TV show, and created a wealth education platform for new investors.In this episode of RealDealChat, Jack sits down with Dedric & Krystal Polite, stars of Hulu’s 50/50 Flip and founders of Polite Wealth Portal, to discuss their journey from 9–5 jobs to becoming respected real estate investors, educators, and TV personalities.The Polites share how social media led to their Hulu deal, why their motto is “doing good while doing well,” and how they built a business model that blends wealth-building with communit...
2025-09-1434 min
Real Estate Investing with RealDealChatAI, Home Buying & Commission Rebates: Paul Cecil on Disrupting Real EstatePaul Cecil of ReAlpha shares how AI, commission rebates, and acquisitions are disrupting home buying—and what it means for buyers and investors.In this episode of RealDealChat, Jack sits down with Paul Cecil, President of ReAlpha (NASDAQ: AIRE), to discuss how his company is transforming real estate through AI and innovative business models.Paul explains how ReAlpha offers up to 80% of the buy-side commission back to buyers, why technology can make homes more affordable, and how acquisitions are helping them build an end-to-end home buying platform.Here’s what you’ll learn in thi...
2025-09-1128 min
Real Estate Investing with RealDealChatMobile Home Park Investing Myths vs Reality | Brad JohnsonBrad Johnson breaks down mobile home park investing—debunking myths, sharing value-add strategies, and explaining why this asset thrives in housing crises.In this episode of RealDealChat, Jack sits down with Brad Johnson, co-founder of Vintage Funds, to discuss why mobile home parks are one of the most misunderstood—and potentially profitable—asset classes in real estate.Brad explains why one in 20 Americans lives in a mobile home, how this sector solves the affordable housing crisis, and why stigma keeps many investors out of the space. He also shares his approach to building long-term cash flow r...
2025-09-0930 min
Real Estate Investing with RealDealChatFrom $2.5M in Debt to Commercial Real Estate Success | Paul MoorePaul Moore of Wellings Capital shares lessons from losing millions, shifting into recession-resistant assets, and building a fund with 990+ investors.In this episode of RealDealChat, Jack sits down with Paul Moore, managing partner at Wellings Capital, to discuss his journey from engineering and entrepreneurship to becoming a respected commercial real estate fund manager.Paul shares the mistakes that took him from $1.5M in the bank to $2.5M in debt, and the key lessons that reshaped his investing philosophy. He breaks down why chasing shiny objects nearly destroyed his wealth, and why true success in real...
2025-09-0730 min
Real Estate Investing with RealDealChatFinancial Freedom at 29: Tanisha Souza’s Income Snowball SystemTanisha Souza became financially free at 29 using her patented Income Snowball system. Learn how passive income can replace your 9–5 forever.In this episode of RealDealChat, Jack sits down with Tanisha Souza, attorney-turned-investor and founder of Tardus Wealth Strategies, to discuss her journey to financial freedom and her unique Income Snowball System.Tanisha shares how she went from a burned-out attorney with $100K in student loans to financially free by age 29—replacing her income through smart real estate investing. She explains why passive income is the ultimate wealth strategy, how she and her husband built their port...
2025-09-0437 min
Real Estate Investing with RealDealChatFrom Renovations to Ground-Up: Daniel Angel on Single & Multifamily InvestingDaniel Angel of Apex Investments shares how he shifted from flips to ground-up construction, multifamily acquisitions, and a fixed-return Infinity Fund.In this episode of RealDealChat, Jack sits down with Daniel Angel, co-founder of Apex Investments, to discuss his journey from corporate finance to building a diversified real estate investment company in Atlanta.Daniel explains how Apex evolved from single-family renovations into ground-up construction, build-to-rent communities, and multifamily value-add acquisitions. He also introduces Apex’s Infinity Fund, a fixed-return investment vehicle designed for accredited investors seeking certainty and flexibility.Key takeaways from this co...
2025-09-0225 min
Real Estate Investing with RealDealChatHow Billionaires Think: Richard C. Wilson on Wealth, Mindset & AIRichard C. Wilson reveals lessons from interviewing 100+ billionaires, building family offices, and what investors must know about wealth, mindset, and AI.In this episode of RealDealChat, Jack sits down with Richard C. Wilson, founder of FamilyOffices.com and host of Billionaires.com, to discuss his journey building the world’s largest family office investor club, interviewing billionaires, and creating AI tools for investors.Richard has hosted 300+ investor events, interviewed over 100 billionaires and 70 pro athletes, and built AI-powered tools that synthesize insights from 1,500+ talks. In this conversation, he shares:The most common mindset traits of bi...
2025-08-3135 min
Real Estate Investing with RealDealChatInfinite Banking Explained: Richard Canfield on Building Generational WealthRichard Canfield breaks down infinite banking, family wealth systems, and why mindset—not money—is the foundation of generational wealth.In this episode of RealDealChat, Jack sits down with Richard Canfield of CashFollows.com to dive deep into infinite banking, family banking meetings, and how to create true generational wealth that lasts.Richard shares insights from his latest books—including Don’t Spread the Wealth and Diapers to Dollars—and explains why legacy isn’t just about money, but the knowledge, systems, and mindset we pass down.Here’s what we cover:The infinite b...
2025-08-2835 min
Real Estate Investing with RealDealChatFrom Dentist to Investor: How Blaine McLaughlin Escaped 3% ReturnsTired of weak 401k returns? Discover how Blaine McLaughlin pivoted from dentistry to real estate investing and created a real path to retirement.In this episode of RealDealChat, Jack sits down with Blaine McLaughlin, a practicing dentist who realized after decades of “doing everything right” that his 401k was delivering a disappointing 3% return.That gut punch forced him to rethink retirement and turn toward real estate investing as a way to build wealth and gain true financial freedom. Blaine shares:Why the traditional retirement path failed himHow he shifted into multifamily and short-term rental inve...
2025-08-2630 min
Real Estate Investing with RealDealChatDesigning for Science: Jon Howard on Real Estate, Labs & InnovationDiscover how lab design and science-focused real estate is transforming investing, with Jon Howard of HED sharing strategies, challenges, and insights.In this episode of RealDealChat, Jack sits down with Jon Howard, architect and sector leader at HED, to explore the specialized world of designing for science-based tenants — from biopharma labs to advanced manufacturing facilities.Jon shares his career journey, why science-focused real estate is a growing asset class, and how design decisions can make or break a property’s ability to attract tenants. Topics include:Why science and lab facilities are attracting more inve...
2025-08-2431 min
Real Estate Investing with RealDealChatFrom Engineer to Investor: Lane Kawaoka’s Wealth Elevator StrategyFrom engineer to real estate syndicator, Lane Kawaoka reveals how he built financial freedom through rentals, syndications, and forced appreciation.In this episode of RealDealChat, Lane shares his journey from buying his first rental in 2009 to scaling into 11 single-family homes, then making the leap into commercial real estate and syndications. We cover the lessons learned from out-of-state investing, the challenges of scaling with rentals, and why appreciation strategies often beat pure cash flow.📌 Timestamps:00:00 – Lane’s journey from engineer to real estate investor02:00 – First rental property & the spark for financial freedom03:0...
2025-08-2128 min
Real Estate Investing with RealDealChatFrom Flipping Hundreds of Homes to Private Lending Success w/ Rich LennonDiscover why seasoned investor Rich Lennon walked away from flipping and rentals after hundreds of deals — and how he built a thriving private lending business with returns that beat traditional investing. In this conversation, Rich shares his biggest lessons learned, including why expanding outside your market can be costly, the real truth about BRRRR returns, and how “lazy money” partners fit into his lending model.We also dive into his philosophy on wealth-building, mistakes to avoid, and even how he teaches his kids about money with the "Lennon Bank." Whether you’re new to real estate or a season...
2025-08-1926 min