Real Estate Investing with RealDealChat
Real Estate Investing with RealDealChat is a podcast featuring interviews with experienced real estate investors, wholesalers, flippers, landlords, and operators actively closing deals. Each episode breaks down: • Real estate investing strategies • Deal sourcing and wholesaling tactics • Fix and flip systems • Rental property scaling • AI and automation tools for investors • Deal operations and lead management Hosted by Jack Hoss, a real estate investor and founder of RealDealCrew, the show focuses on practical execution — not theory. Whether you're wholesaling houses, flipping properties, building a rental portfolio, or scaling a real estate investing business, this podcast delivers real-world lessons from operators actively doing deals. Follow...
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From $100K to $15M Raised: The Passive Income Blueprint w/ Bronson Hill
<p>Bronson Hill shares how he went from $100K raised to $15M in 18 months and why single family investing is holding most people back.</p><p>In this episode of RealDealChat, Jack Hoss sits down with Bronson Hill, author of Fire Yourself and host of The Mailbox Money Show, to dig into what real passive income actually looks like and how to build it through syndication and alternative assets.</p><p>Bronson covers:</p>Why trading time for money traps even high-earning professionalsHow he went from 4 single family rentals to a 225-unit syndication dealThe difference between a property manager and...
From Immigrant to Real Estate Mogul: Doren Levi's Journey
<p>In this conversation, Doren Levi shares his journey from being an immigrant to becoming a successful real estate developer. He emphasizes the importance of human connection in business, the lessons learned from early ventures, and the significance of betting on oneself. Doren discusses the challenges of partnerships, the power of mindset, and the need to create meaning beyond financial success. He also shares insights into his current projects and future aspirations in the real estate market.</p><p>Takeaways</p>Doren Levi is a real estate investor with a unique background.His journey from immigrant to developer was driven...
Why Security Deposits Are Costing Landlords More Than They Think w/ Andrew Bowen
<p>Lease insurance for rental property explained: Andrew Bowen of LeaseLock breaks down how to replace deposits and protect your assets at scale.</p><p>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.</p><p>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.</p>What lease insurance actually is and how it replaces the deposit with...
What Investors Decide in the First 10 Minutes W/ Scott Kelly
<p>Scott Kelly has helped companies raise over $5 billion. Here's what investors actually decide in the first 10 minutes of your pitch.</p><p>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.</p><p>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...
48 Years of Landlording — What New Investors Get Wrong w/ Joel Miller
<p>SEO-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.</p><p>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.</p><p>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...
He Set a Goal of 40 Units. He Ended Up with 2,700 w/ Jens Nielsen
<p>Jens Nielsen left a 25-year IT career and went from 40-unit goal to managing 2,700 units — here's the exact path he took to scale commercial real estate.</p><p>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.</p><p>Jens covers:</p>How he started with a fourplex for $115K and scaled from thereWhy he ditched single-family immediately and went straight to small multif...
Why the Next 3–5 Years Are the Best Ever for Notes w/ Eddie Speed
<p>Eddie Speed has closed 50,000+ note deals in 45 years — and says the next 3–5 years may be the best window for note investing he's ever seen.</p><p>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.</p><p>Topics covered include:</p>Why the next 3–5 years could be the greatest window f...
You Don't Own Your Brand (Until You Do This) w/ Joey Vitale
<p>Joey Vitale reveals why most entrepreneurs don't legally own their brand — and the trademark strategy that protects everything you're building.</p><p>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.</p><p>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.</p><p>Topics covered:</p>Why you don't legally own your...
Why Your Investment Property Is Probably Underinsured w/ Michael Silverman
<p>Michael Silverman reveals why most investment properties are underinsured — and the liability gaps that could cost investors everything.</p><p>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.</p><p>Michael covers:</p>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...
Turn One House Into 28 Doors with Co-Living w/ Katrina E. Robinson
<p>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.</p><p>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.</p><p>Katrina covers:</p>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...
