Real Estate Investing with RealDealChat

byRealDealCrew / Jack Hoss

BusinessEntrepreneurshipInvesting

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...

Episodes(40 episodes)

The 3 Silent Budget Killers Destroying Your Flip Profits w/ Kevin Dairaghi

Kevin Dairaghi built a house flipping operation in St. Louis and reveals the 3 silent budget killers that crush real estate investors before they ever scale.In this episode of RealDealChat, Jack Hoss sits down with Kevin Dairaghi of Restore STL to talk about what really happens when you go from doing a few flips a year to running a real operation.Kevin covers:The 3 biggest silent budget killers investors overlook on every flipWhy doing 10 houses a month almost broke him mentally and financiallyHow personal development drives professional performance in real estateThe 5-step recipe for...

Published: May 12, 2026Duration: 38m 27s

They're Building Homes with Grass. It Actually Works. w/ Josh Dorfman

Josh Dorfman explains how Planted is turning fast-growing grass into structural building panels now used by DR Horton, the largest home builder in America.In this episode of RealDealChat, Jack sits down with Josh Dorfman, CMO of Planted and founder of climate media company Supercool, to break down one of the most unusual innovations hitting the construction supply chain right now.Planted is replacing traditional lumber and oriented strand board with panels engineered from a perennial grass that grows 10x faster than trees, can be harvested one to two times per year, and locks carbon...

Published: May 10, 2026Duration: 35m 33s

Why Most Financial Advisors Avoid Real Estate w/ CJ Davidson

CJ Davidson explains why most financial advisors can't help real estate investors — and how Proxy Financial is built to actually bridge that gap.In this episode of RealDealChat, Jack sits down with CJ Davidson, founder of Proxy Financial, to dig into what's broken in the financial advisory industry and why real estate investors are often left without real guidance.CJ shares:Why real estate has to be at the core of every financial plan, not an afterthoughtHow most advisors avoid real estate conversations because they're not equipped to have themThe "art and science" model be...

Published: May 8, 2026Duration: 40m 57s

Why Billionaires Only Put 20% in the Stock Market w/ Bob Fraser

Bob Fraser reveals why billionaires keep only 20% in public markets and how private alternatives can protect and grow wealth — without chasing returns.In this episode of RealDealChat, Jack Hoss sits down with Bob Fraser, CFO and chief macro strategist of Aspen Funds and co-author of the USA Today bestseller Invest Like a Billionaire, to break down how the ultra-wealthy structure their portfolios and why most investors are playing the wrong game entirely.Bob covers:Why billionaires keep only 20-30% of their wealth in public marketsThe difference between diversification and true mathematical uncorrelationWhy the S&P...

Published: May 6, 2026Duration: 33m 0s

Why 11% Beats the S&P 500 (Without the Risk) w/ Jay Patel

Jay Patel reveals how PropTechs delivers a consistent 11% return backed by real estate collateral — and why it outperforms the S&P 500 without the volatility.In this episode of RealDealChat, Jack sits down with Jay Patel, founder of PropTechs — a real estate investment fund built for passive investors who want consistent, collateralized returns without the headaches of active ownership.Jay breaks down:Why PropTechs is structured to pay investors their 11% before the fund makes a single dollarHow 150% collateral coverage protects capital in any market environmentThe three verticals inside the fund: short-term transactions, long-term holdings, and a 25...

Published: May 4, 2026Duration: 41m 2s

Why 90% of Success Has Nothing to Do With Strategy w/ Dr. Noah St. John

Dr. Noah St. John reveals why 90% of success is your inner game and how head trash is the hidden friction capping your income and business growth.In this episode of RealDealChat, Jack Hoss sits back down with Dr. Noah St. John, bestselling author, performance coach, and creator of the Afformations Method, to dig into what's actually holding investors and entrepreneurs back from their next level.Noah breaks down:Why 90% of success is your inner game, not your strategyWhat "head trash" is and how it creates a revenue ceiling you can't push throughThe difference between...

Published: May 2, 2026Duration: 36m 48s

From $100K to $15M Raised: The Passive Income Blueprint w/ Bronson Hill

Bronson Hill shares how he went from $100K raised to $15M in 18 months and why single family investing is holding most people back.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.Bronson covers: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...

Published: Apr 30, 2026Duration: 32m 22s

From Immigrant to Real Estate Mogul: Doren Levi's Journey

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.TakeawaysDoren Levi is a real estate investor with a unique background.His journey from immigrant to developer was driven...

Published: Apr 28, 2026Duration: 33m 39s

Why Security Deposits Are Costing Landlords More Than They Think w/ Andrew Bowen

Lease 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...

Published: Apr 26, 2026Duration: 31m 27s

What Investors Decide in the First 10 Minutes W/ Scott Kelly

Scott 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...

Published: Apr 24, 2026Duration: 35m 8s

48 Years of Landlording — What New Investors Get Wrong w/ Joel Miller

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.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...

Published: Apr 22, 2026Duration: 42m 3s

He Set a Goal of 40 Units. He Ended Up with 2,700 w/ Jens Nielsen

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.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...

Published: Apr 20, 2026Duration: 31m 27s

Why the Next 3–5 Years Are the Best Ever for Notes w/ Eddie Speed

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.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...

Published: Apr 18, 2026Duration: 34m 46s

You Don't Own Your Brand (Until You Do This) w/ Joey Vitale

Joey 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...

Published: Apr 16, 2026Duration: 32m 3s

Why Your Investment Property Is Probably Underinsured w/ Michael Silverman

Michael 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...

Published: Apr 14, 2026Duration: 30m 7s

Turn One House Into 28 Doors with Co-Living w/ Katrina E. Robinson

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 us...

Published: Apr 12, 2026Duration: 33m 37s

He Never Sold a Property. Now He Has 30 Buildings. w/ Onyi Odunukwe

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 lo...

Published: Apr 10, 2026Duration: 32m 34s

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

Bob Lachance went from 50 deals to 270 deals a year using virtual assistants — and built one of the top VA companies in real estate. Here's exactly how.In this episode of RealDealChat, Jack Hoss sits down with Bob Lachance, former pro hockey player turned real estate investor, co-founder of Fortune Builders, and CEO of REVA Global — one of the leading virtual assistant companies serving real estate investors.Bob covers:From ice hockey to real estate: how a $32K first deal turned into a full investing businessWhy the first deal exposed everything: no systems, no marketing, runn...

Published: Apr 8, 2026Duration: 32m 41s

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

Kirk Welsh lost $104K to a contractor, then rebuilt with systems, accountability, and personal development. Here's the framework that changed everything.In this episode of RealDealChat, Jack Hoss sits down with Kirk Welsh — licensed architect, real estate investor, flooring company owner, and personal development coach — to have the conversation most real estate content avoids: the inner game of running a business.Kirk covers:The path from licensed architect to real estate investor to flooring company owner — and why entrepreneurship exposed everythingHow being the "doormat" (not the boss) led to a contractor walking off with $104,000Why yo...

Published: Apr 6, 2026Duration: 27m 59s

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

Michael Coxen burned out chasing deals, ended up hospitalized with colitis, and then built his best business by becoming more mindful. Here's how.In this episode of RealDealChat, Jack Hoss sits down with Michael Coxen, Las Vegas real estate broker, investor, and host of The Mindful Agent Podcast, to explore the intersection of mindfulness, health, and business performance — and why intentional living turns out to be a better growth strategy than hustle.Michael covers:How ulcerative colitis hospitalized him multiple times and forced a complete resetWhy becoming more mindful was an accident — and how it l...

Published: Apr 4, 2026Duration: 40m 7s