Dealmaker Catalyst

Jason Seward & Jim Ingersoll
  • 5.0 (26)
  • Investing
  • Updated Weekly

Join the Dealmaker Catalyst Podcast for real conversations with real estate investors and entrepreneurs. Learn how they approach deals, solve problems, and build their businesses. Every episode gives practical takeaways to help you make smarter moves in real estate.

  1. 17h ago

    Buying Real Estate Overseas Without Getting Burned | Michael Cobb

    Most people who've ever taken a vacation somewhere beautiful have had the thought: what would it take to own a piece of this? On this episode, Jason Seward sits down with Michael K. Cobb, founder and CEO of ECI Development and one of the most recognized names in international real estate, to answer exactly that. Since 1996, Michael has built residential communities across Belize, Nicaragua, Panama, Costa Rica, Honduras, and El Salvador, and he literally wrote the book on buying property abroad. This conversation is a field guide to doing it without getting burned. Michael breaks down why he built his entire career "outside the competition," how "margarita madness" leads well-meaning buyers into contracts they regret, and the three simple principles that keep you safe when you leave the bubble of North American consumer protection. From the difference between a heart decision and a head decision, to the "time machine" framework for choosing a country, to what international financing actually looks like, this is a grounded, story-rich playbook from someone who's done it for nearly thirty years.   What You'll Learn in This Episode Why the biggest opportunities live "outside the competition," and how Michael built a mortgage business and development company where no market existed What "margarita madness" is and why relaxed, wined-and-dined buyers keep signing contracts they later regret How the three principles — buy what you see, own the community, know the developer — protect you in a buyer-beware environment Why buying overseas is a head decision when it's an investment and a heart decision when it's lifestyle, and how to tell which one you're making How the "time machine" concept helps you choose a country based on whether you want cash flow now or appreciation over time What international financing really looks like, including higher down payments, higher rates, and shorter terms than in the US   Timeline Highlights [0:10] – Jason introduces the show and the Dealmaker Catalyst community rooted in Jim Ingersoll's culture [1:04] – Michael K. Cobb introduced: founder of ECI Development and international real estate pioneer since 1996 [3:10] – The guiding quote: "There is no competition outside; the masses strive to be outside the competition" [5:18] – Creating the game: building a mortgage business where no bank would finance foreign buyers [7:16] – The opportunity most people missed, and how inspecting collateral revealed a development opening [8:26] – Mismatched door handles and single outlets: the "off" product that sparked North American–standard building [9:49] – Where most international buyers get burned, and why it's the process, not the product [10:55] – "Margarita madness" explained: how great vacations turn into regretted contracts [12:21] – Jason's own near-miss buying a condo in the Bahamas after being wined and dined [14:10] – The three principles introduced: buy what you see, own the community, know the developer [15:11] – "Buy what you see, pay for what you see," and structuring payments as things get delivered [15:55] – Own the community: avoiding ghost towns and asking whether renters will actually have a good time [17:34] – Know the developer: why there's no government agency or lemon law to back you up [18:46] – Leaving the land of consumer protection: freedom and personal responsibility overseas [20:50] – Exceptions to the rules, getting your own attorney, and refundable-deposit milestone structures [23:15] – Boiling it all down to one word: humility, plus going slow and stretching the process out [24:26] – Legitimate investment opportunities abroad and how to mitigate risk with critical analysis [26:45] – The "time machine" framework: choosing a country by cash flow versus appreciation [28:27] – Why brands like Marriott and Hilton put "heads on beds" and drive rental performance [29:24] – The rule of thumb on developer pro formas and the question "How many are you keeping?" [31:11] – The HGTV question: how international buyers actually finance these purchases [32:18] – International financing framework: higher down payments, 11–18% rates, 10–20 year terms [34:23] – Why financing suits lifestyle buyers but rarely makes sense for pure investors [36:19] – A smart strategy for scouting property while on a family vacation without ruining the trip [37:21] – Why serious investors should visit in the worst season to see roads and conditions honestly [39:47] – The truth about overseas yields and why diversification, not higher cash flow, is the real reason [41:10] – Putting a price on the intangible: Jason's mom's question about sitting on the deck by the ocean [42:24] – Why Michael wrote the book: heartbreak, 300+ articles, and helping people avoid getting ripped off [44:27] – Where to find the book and Michael's consulting through Development Advisors [44:51] – The Amazon review offer: a personalized hardcover and a Belize chocolate bar (US only) [45:52] – Closing thanks to Michael and the Dealmaker community   Resources Mentioned Dealmaker Catalyst community — https://dealmakercatalyst.com Community discount program (Lowe's / Sherwin-Williams nationwide discounts) — https://elitedealmakers.com/discount 608B Capital Funding (episode sponsor) — fix-and-flip, BRRRR, and value-add lending, plus a debt fund for accredited investors — https://608bcapital.com/   Connect and Subscribe If this episode got you dreaming about a place by the ocean while also thinking harder about the process behind it, that's exactly the point. Michael's whole message is that a great transaction overseas comes down to humility, patience, and asking the right questions before you sign anything. Grab the book, take him up on the review offer, and reach out through Development Advisors if you want hands-on help with due diligence. If you got value from this one, subscribe, leave a review, and share it with someone who's serious about leveling up. Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.

    47 min

  2. Jul 2

    How to Lend Money on Real Estate Deals You Don't Actually Have | Chuck Glover

    Chuck Glover didn't start building wealth until he was 70 years old. Six and a half years later, with no prior background in real estate or investing, he's a private money lender, author of The $5,000 Millionaire, and the architect of a "massive achievement" philosophy that has funded mission trips across the globe. In this episode of Dealmaker Catalyst, host Jason Seward sits down with Chuck to pull apart the exact mechanics of wrap lending, one of the most misunderstood ways to build wealth using other people's money. This is a whiteboard session, not a hype reel. Chuck walks through how he combines a small amount of his own cash with a passive investor's capital to fund a single loan, how the numbers turn a $20,000 stake into a 35 to 40% return, and why none of it works without the education and relationships behind it. If you've ever heard the term "wrap lending" and nodded along without really knowing what it means, this is the conversation that finally makes it click.   What You'll Learn in This Episode What wrap lending actually is and how it differs from traditional owner financing  How Chuck pairs his own capital with a passive "underlying lender" to fund one loan  Why an underlying lender happily earns 9% while the wrap lender keeps the spread and the points  How the math turns a $20,000 position into roughly a 35 to 40% annual return  Why first lien position and full transparency protect everyone at the table  How to shorten the learning curve through mentors, meetups, and relentless follow up   Timeline Highlights [1:03] – Jason introduces Chuck Glover, private money lender and author of The $5,000 Millionaire [3:23] – The March Richmond event that brought a 300 person room to tears [4:06] – "It was time to stop quitting" and why this episode zeroes in on wrap lending [5:12] – Wrap lending explained at its most basic form, and the two types that exist [6:23] – Chuck's model: never telling a borrower "sorry, I can't help you" [7:26] – Where the term "wrap" comes from, with a $20K and $180K example [7:59] – Paying the underlying lender 9% while lending to the borrower at 13% [9:03] – Why passive investors earn 9% and the wrap lender earns the delta [10:41] – First lien position, second lien position, and total transparency [12:52] – Why you cannot jump into this blindly without education [13:40] – Learning from Dorsey Ford and thousands of hours at real estate meetups [19:13] – Vetting a deal, walking the property, and keeping agreements to a page and a half [24:25] – The full math: two points plus the spread equals a 35 to 40% return on $20K [26:46] – Compounding the model by recycling loans and running up to 30 at once [34:44] – Starting at 70 with zero investing background, now 77 and traveling the world [36:25] – The mindset piece: killing "excuse-itis" and never holding a thought that weakens you [39:09] – Where to find Chuck's book and his live wrap lending class on July 14th   Resources Mentioned The $5,000 Millionaire by Chuck Glover — his book on building wealth from a small starting stake: https://massiveachievement.net/merch Massive Achievement — Chuck's book, merch, and his live wrap lending Zoom class (next session July 14th): https://massiveachievement.net Chair the Love (CHAIR) — the nonprofit Chuck travels with to distribute free wheelchairs worldwide: https://chairthelove.org 608B Capital Funding (episode sponsor) — fix and flip, BRRRR, and value add loans plus a debt fund for accredited investors: https://608bcapital.com/ Dealmaker Discount — nationwide discounts at Lowe's, Sherwin-Williams, and more for community members: https://elitedealmakers.com/discount Connect and Subscribe If Chuck's story lit a fire under you, don't let it fade at the end of the episode. Grab his book, look into the July class, and start showing up to the rooms where deals and relationships get made. Subscribe to Dealmaker Catalyst, leave a review, and share this one with someone who thinks it's too late to start. Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.

    45 min

  3. Jun 25

    The Financial Framework That Tells You Where All the Money Went | David Richter

    David Richter is the author of Profit First for Real Estate Investing, founder of Simple CFO Solutions, and one of the most recognized voices in real estate financial management. After working inside a company doing 25 deals a month and watching the money disappear anyway, he spent years helping real estate investors stop the bleeding and build actual financial systems that put cash in their pockets. In this episode, David breaks down why so many investors are skilled at doing deals but still end up broke, and walks through the core Profit First framework including the "golden trio" of bank accounts every investor should set up. If you're a wholesaler, flipper, landlord, or buy-and-hold investor who wants to stop living deal to deal and start keeping what you earn, this one is worth your full attention.   What You'll Learn in This Episode Why making more deals doesn't solve the cash flow problem and what actually changes your financial situation How the wealth formula (sales minus profit equals expenses) works and why most investors have it completely backwards What the "golden trio" bank accounts are and how to set them up even if you're just doing real estate on the side Why paying yourself feels wrong to so many investors and how to reframe it as a business discipline, not a reward How Simple CFO's three-part financial foundation (Profit First implementation, bookkeeping systems, and a financial dashboard) works in practice What trips most investors up when they try to implement Profit First and how to avoid those common mistakes   Timeline Highlights [1:03] – Host introduces David Richter, author of Profit First for Real Estate Investing and founder of Simple CFO [2:26] – David traces his origin story: from college real estate dreams to sitting in the finance seat at a 25-deal-a-month company [3:22] – The hard truth: doing 25 deals a month but spending more than they made, and realizing it wasn't just them [4:00] – Working with investor Rich Lennon, helping him get clarity on numbers, and watching that single shift change everything [5:43] – A mentor recommends the original Profit First book; David reads it in one evening and incorporates it into Simple CFO from day one [7:35] – Why most real estate investors stay broke even when they're good at deals: they never learned the game of money [9:11] – The core reframe: it's not the number of deals you do, it's what you do with the money once it hits your account [14:20] – The wealth formula explained: sales minus profit equals expenses, and why most investors have the formula backwards [16:08] – The Profit First system in plain terms: the envelope method applied to business bank accounts [17:47] – The golden trio of accounts: profit, owner's comp, and owner's tax, and what each one is actually for [21:08] – Why investors feel guilty about paying themselves and why that guilt is costing them good decisions [22:30] – A real investor success story: one account, one dollar amount per deal, six months of reserves built in a year [30:05] – How Simple CFO works: three pillars (Profit First, bookkeeping, and a financial dashboard) and two program levels based on revenue [33:48] – A breakdown of the book's chapter structure and the workbooks available for specific exit strategies (wholesale, fix and flip, rentals) [36:37] – Where to get the book, workbooks, and audible version with additional implementation content   Resources Mentioned Profit First for Real Estate Investing by David Richter: https://simplecfo.com/pfrei-book Simple CFO Solutions workbooks (wholesale, fix and flip, rentals) — https://www.simplecfo.com/workbooks Dealmaker Discount — nationwide discounts at Lowe's, Sherwin-Williams, and more for community members: https://elitedealmakers.com/discount 608B Capital Funding (episode sponsor): https://608bcapital.com/   Connect and Subscribe If this conversation hit home, share it with the investor in your network who's doing deals but still can't figure out where the money goes. David lays out exactly what to do first, and it starts with opening one account this week. Subscribe to Dealmaker Catalyst, leave a review, and keep showing up for conversations like this one. Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.

    38 min

  4. Jun 18

    Attention Became the Most Valuable Asset in Real Estate | Jon Schoeller

    Jon Schoeller has spent 20 years building businesses, flipping over 400 real estate deals, and lending on more than 100 — but the move that changed everything was pointing a camera at what he was already doing. Starting from scratch documenting his house flips in Charleston, West Virginia, he grew to over 1 million YouTube subscribers and 2 million followers across all platforms, generating between 30 and 100 million views a month alongside a thriving flipping and lending operation. This episode is a tactical field guide for real estate investors who know they should be on social media but don't know where to start, keep starting and stopping, or are chasing the wrong metrics. Jon breaks down exactly how content creation fueled his deal flow and private money pipeline without a single direct pitch, why consistency beats quality every time, and what the first three months of building a channel should actually look like. If you've been waiting for permission to just hit record, this is it. What You'll Learn in This Episode How Jon used before-and-after flip videos to attract private lenders and deal flow without ever soliciting investors directly. Why the number of followers matters far less than who those followers are, and how 100 local views can outperform 100,000 international ones for a real estate business. What the first three months of a content strategy should focus on, and why proving consistency to yourself is the only goal that matters in that window. How to structure a short-form video hook in the first ten seconds to stop the scroll and build an audience that actually trusts you. Why going viral on your first post can actually be a bad thing, and how setting an unrealistic baseline early on leads most creators to quit. What gear you actually need to start, and why your phone, a sub-$100 DJI mic, and a window are enough to produce credible content from day one.   Timeline Highlights [1:03] – Jon's background: 300+ house flips locally, 100+ lending deals, and building a channel to 1M+ subscribers by documenting the journey [3:36] – How Jon went from flipping furniture and motorcycles to real estate, and why his YouTube channel started as a real estate and finance channel [9:22] – How the algorithm forced Jon into a lane and why before-and-after flip videos became his most viral content category [11:33] – Why Jon believes attention is the number one asset in the world right now, and what that means for every real estate investor with a business to grow [13:12] – The local audience principle: why 100 targeted views in your market beats 100,000 views from people who will never do a deal with you [17:06] – The danger of letting one viral post hijack your niche, and how to think about algorithm signals without getting sidetracked [18:04] – Why Jon hopes you don't go viral in your first month, and how early wins set an unsustainable bar [22:04] – The husband-and-wife channel comparison: Jon posted every week for over a year before making a dollar; his wife monetized in three months [24:17] – The three-month commitment framework: why the first ninety days are about proving consistency to yourself, not growing an audience [29:03] – What Jon's extreme accountability wiring looks like in practice, and how he showed up to record this episode through a migraine [34:17] – Three things to do this week: switch your phone to 4K vertical, start documenting what you're doing, and move your best five seconds to the front of the video [37:13] – The hook formula: why how you open the first ten seconds determines whether anyone watches the rest [40:13] – When to hire help, when not to, and why bootstrapping content creation for the first three months protects you from a costly mistake [44:37] – Why people are overthinking production quality and what authenticity actually looks like in today's content landscape [47:15] – Why ideas are not what's rare — implementation is, and how that reframe applies to both content creation and business [52:13] – The last-minute podcast cancellation story and what it reveals about how someone will run their business   Rapid Fire Highlights Dangerous early belief: Content had to be perfect. What he had to give up to win on social media: Perfectionism. What he wouldn't do again: Worry about the views. Most recent business mistake: Sent construction draw funds too early before they were due, got over-leveraged with a bad communicator as a borrower. Going forward: no premature draws.   Resources Mentioned The Frugal Investor on Instagram — https://www.instagram.com/thefrugalinvestor/?hl=en Dealmaker Discount — nationwide discounts at Lowe's, Sherwin-Williams, and more for community members: https://elitedealmakers.com/discount 608B Capital Funding — fix-and-flip, BRRRR, and value-add lending plus a debt fund for accredited investors: https://608bcapital.com   Connect and Subscribe Jon dropped a master class in this one, from the attention economy to the three-month consistency test to the exact gear setup that gets you on camera without excuses. Share this episode with someone in your network who keeps saying they'll start posting "when the time is right." Subscribe to Dealmaker Catalyst, leave a review, and help us keep bringing operators like Jon to the table. Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.

    59 min

  5. Jun 11

    The 10 Ways Real Estate Actually Makes You Money | David Greene

    David Greene is a former Bay Area police officer turned nationally recognized real estate authority — bestselling author of Long Distance Real Estate Investing, Buy, Rehab, Rent, Refinance, Repeat, Pillars of Wealth, Better Than Cash Flow, and The Top Producer Trilogy — whose work on the BiggerPockets podcast helped build the investing foundation of an entire generation of operators, including host Jason Seward. He owns Coast to Coast Real Estate, Coast to Coast Getaways, and The One Brokerage, and invests personally in long-term rentals, short-term rentals, and flips across the country. In this episode, David walks through all ten ways real estate generates wealth, pulled directly from his newest book Better Than Cash Flow. He breaks down cash flow, equity, loan paydown, tax strategy, and what he calls the "bonus method" — the often-missed income stream hiding inside real estate expertise itself. If you've ever looked at a deal through just one lens and walked away thinking it didn't work, this episode reframes how you look at every property you'll ever consider.   What You'll Learn in This Episode How real estate investors have been trained to analyze deals too narrowly — and why the single-metric approach is costing them opportunities in today's market What "forced cash flow" and "forced equity" actually mean, and how to manufacture wealth from properties others walk past Why market appreciation cash flow should influence where you deploy capital long before you look at a spreadsheet How to use macroeconomic signals like quantitative easing to time your real estate moves more intelligently What the "bonus method" is and why working inside real estate while you invest in it is a wealth multiplier most people ignore Why knowing your defense in both jiu-jitsu and real estate is what actually frees you up to go on offense   Timeline Highlights [0:16] – Jason introduces David Greene: author, broker, investor, and the voice behind much of his early investing foundation [1:52] – Jason publicly credits David's BiggerPockets work for helping him build a BRRRR portfolio of 100+ properties [3:32] – David shares his first impressions of Virginia and the blue-collar work ethic he found there [4:04] – David explains why the simple cash-on-cash return model no longer works in a competitive market [6:48] – The three groups broken down: cash flow, equity, and miscellaneous — and why stacking them is the real strategy [7:29] – Natural cash flow explained, and why analyzing only year-one rent is a fundamentally flawed approach [9:01] – Forced cash flow: ADUs, unit splits, usage changes, and how apartment operators have been doing this for years [10:41] – Market appreciation cash flow: how to identify constricted supply and rising wages to predict where rents will grow [13:35] – Natural equity, buying equity, and forced equity: what each one means and how to stack them inside a single deal [19:24] – How to combine all ten methods together — and why knowing all of them is what removes fear and analysis paralysis [23:55] – A practical MLS hack: how misreported square footage creates hidden buying equity opportunities most investors miss entirely [30:34] – David's case for apprenticeships over YouTube courses — why working for free beats "what I deserve" every time [33:05] – The Chris Lloyd story: what a producer's mindset looks like in practice and why it's the foundation of every real relationship in business [36:46] – David connects the ten ways, the 32 principles, and the bigger life philosophy underneath all of it   Resources Mentioned 608B Capital Funding (episode sponsor) — fix and flip, BRRRR, and value-add lending, plus a passive debt fund for accredited investors — 608bcapital.com Better Than Cash Flow by David Greene — available on Amazon The 32 Principles by Rener Gracie — recommended by David for business and life application Everything Is Figureoutable by Marie Forleo — referenced for building confidence through reps and experience The David Greene Show — under the Real Talk Real Estate Network Coast to Coast Real Estate — coasttocoastrealestate.com Coast to Coast Getaways — short-term rental property management Dealmaker Catalyst Community — EliteDealmakers.com   Connect and Subscribe If this conversation gave you a new way to look at your next deal, share it with another investor in your network who's been stuck analyzing from just one angle. Subscribe to Dealmaker Catalyst on your favorite platform, leave a review to help us grow, and stay plugged into the operators who are doing this at a high level every day. Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.

    40 min

  6. Jun 4

    What the Best Real Estate Investors All Have in Common | Jim Ingersoll

    Ten episodes in and Dealmaker Catalyst is already stacking up a guest list that reads like a masterclass series — from new construction and note buying to buy box clarity, creative deal structures, and the mindset behind building real wealth. In this episode, host Jason Seward sits down with Jim Ingersoll to look back at the first ten shows, highlight the moments that hit hardest, and give listeners a behind-the-scenes look at where the show is headed. If you've missed any episodes or want a fast-track guide to the best ones to start with, this is your roadmap.   What You'll Learn in This Episode Why Brandon Lindsey's new construction episode might be the most detailed A-to-Z breakdown of the development process ever recorded on a real estate podcast How Michael Zuber built a crystal-clear buy box and why his ten rules for consistent, compounding investing are some of the most actionable content the show has produced What makes Wendy Coles' story one of the most-shared episodes in the Dealmaker community, and why her journey from homeless single mom to investor and speaker resonates with so many people How Major Hiller used creative deal-making — including trading a property for a clam boat — to build a real estate business starting with $1,500 and a copy of Deals on Wheels Why Ali Murphy's challenge to prove your "why" with your actual calendar and actions has become one of the most talked-about sessions in Dealmaker history How reviews and shares on Apple Podcasts directly fuel the algorithm and compound the reach of every episode   Timeline Highlights [1:02] – Jim and Jason reflect on the first ten episodes and what made the show materialize exactly as they envisioned [2:10] – The Brandon Lindsey new construction episode: why Jim half-jokingly said they could package it up and sell it as a course [4:48] – Michael Zuber's episode breakdown: his crystal-clear buy box, ten rules for investing, and why Brian Burnett in Jackson, Mississippi called it out specifically [7:07] – Why podcast reviews matter more than most people realize, and how the compounding effect of five-star ratings fuels the algorithm and expands reach [9:29] – Wendy Coles: from homeless in Buffalo to investor and public speaker, and why her episode on this show and Jim's Burning the Ships podcast both went wide [12:52] – David Greene's appearance at Dealmaker Hampton Roads and the ten ways to make money right now that he walked listeners through [13:44] – Tony Marino from Huntsville: leading with faith and family, and why the most memorable part of his episode had nothing to do with real estate [14:06] – Ali Murphy's episode and her challenge to prove your why with your actions, not just your words [16:57] – Eddie Speed: scratching the surface of note investing and why listeners were encouraged to go deeper with Eddie and his team directly [19:53] – Major Hiller's story: moving back home with $1,500, reading Deals on Wheels, and trading a clam boat to close a deal four years in the making [21:50] – Dave Volpe and the origins of Dealmaker, starting with an "Invest Freedom Without Banks" weekend that laid the foundation for the entire community [24:36] – Tom Olson: vertical integration, knowing your numbers, and what real leadership looks like when you're running multiple companies simultaneously [29:26] – Looking ahead: what topics listeners want more of, upcoming guests, and why Jim and Jason want to cover the messy syndication stories alongside the wins [33:27] – How to get on Jim Ingersoll's newsletter and what makes it worth subscribing to   Resources Mentioned Dealmaker Catalyst Community Facebook Group — search Dealmaker Catalyst on Facebook 608B Capital Funding (episode sponsor) — fix and flip, BRRRR, and value-add lending, plus a passive debt fund for accredited investors — 608bcapital.com Jim Ingersoll's newsletter — email jim@elitedealmakers.com to subscribe Lowe's and Sherwin-Williams community discounts for Dealmaker members — elitedealmakers.com/discount Deals on Wheels by Lonnie Scruggs (mentioned by Major Hiller) Brandon Lindsey's TRP community (referenced by Jim) Freedom Founders mastermind (Dave Volpe) Burning the Ships podcast (Jim Ingersoll) — Daniel Claman and Adrian Smooth episodes referenced   Connect and Subscribe If you've been meaning to go back and catch the episodes from the first ten that Jason and Jim highlighted here, now is the time — Brandon Lindsey, Michael Zuber, Wendy Coles, and Major Hiller alone are worth a full afternoon. Share this episode with someone in your network who's serious about leveling up their real estate investing, and subscribe on Apple Podcasts so you never miss a Thursday drop. Leave a five-star review while you're there — it takes ten seconds and it directly helps more people find this show. Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.

    36 min

  7. May 28

    Why Holding Real Estate Until You Die Is the Most Profitable Exit Strategy | Leon Johnson

    Leon Johnson has been building businesses and stacking assets since before most people even start thinking about financial freedom. At 73, he holds a portfolio that includes decades of buy-and-hold real estate, H&R Block franchises he ran for 20 years, and independent insurance agencies — built on a simple philosophy that employees come first, customers come second, and the right deal structure can outlast any market cycle. This episode was recorded live at a Dealmaker event, the first time host Jason Seward and Leon had ever met, and it shows. The conversation moves from leadership and culture to legacy-driven deal structure, the brutal $400,000 lesson Leon took from a business partner at age 28, and why he says he'd give up 99% of his net worth to get 20 years back. If you're trading time for dollars and wondering how to stop, Leon's been living the alternative for decades and has the receipts to prove it.   What You'll Learn in This Episode How holding real estate long-term and passing it to your heirs through stepped-up basis can eliminate capital gains taxes that would cost hundreds of thousands of dollars in a traditional sale. Why putting employees above customers is the management principle that determines whether your team shows up ready to serve or quietly checked out. What unearned income actually means as an IRS term and how deliberately converting earned income to rents, interest, and royalties changes the trajectory of your financial future. How a 30-year master lease with an option to purchase can solve a seller's tax concerns, management fatigue, and legacy goals all in a single creative structure. Why starting early is the most powerful wealth-building variable, and what the compound effect of time means when you explain it to a teenager versus a 50-year-old. What it really looks like to leave a W2 career for real estate when the income hasn't caught up yet, and how to build the next ship before burning the one you're on.   Timeline Highlights [0:10] – Jason introduces Dealmaker Catalyst and sets up the first-ever live audience podcast with a guest he met hours before [1:43] – Jason kicks off the interview with Leon Johnson in front of a live crowd at a Dealmaker event [2:51] – Leon's Southern background and why the way he communicates immediately puts people at ease [3:36] – How Leon's mindset around freedom from time-for-money thinking started forming early in his career [4:34] – Leon's framework for building businesses: H&R Block franchises for 20 years, independent insurance agencies, and a consistent philosophy [5:04] – Two or three traits Leon sees as common denominators in great leaders across every business he's built [5:30] – The Lowe's story: how one new manager transformed an entire store culture overnight and what that proved about leadership [7:58] – Leon's longest tenant of 23 years, two tenants who stayed 14 years and passed away, and what that says about how he treats people [8:53] – The $400,000 mistake at age 28, buying $4 million worth of houses with a partner who turned on him and what it cost to untangle [10:57] – Why Leon holds almost everything he acquires and the tax logic behind passing real estate to heirs through stepped-up basis [13:18] – The 30-year master lease deal where Adam structured an option to purchase, handled management, and solved a seller's lifelong tax anxiety [15:44] – The $10 billion question reversed: what Leon would give up to be 50 again and what it says about the true value of time [18:03] – Leon's advice for W2 earners mid-career who feel the itch to build something different and why the shift to unearned income is the goal [19:14] – Rents, interest, and royalties as the three pillars of unearned income and how to gradually convert your earned income into them [20:19] – Jason's personal story of putting in his resignation in the same room where this episode was recorded and what it felt like to walk back in   Resources Mentioned 608B Capital — fix and flip, BRRRR, and value-add lending plus a debt fund for accredited investors — 608bcapital.com Lead Dealmakers community discounts at Lowe's, Sherwin-Williams, and more — aleaddealmakers.com/discount The Compound Effect by Darren Hardy Rich Dad Poor Dad by Robert Kiyosaki (Cash Flow Quadrant framework) Dealmaker Catalyst community — dealmaker catalyst.com   Connect and Subscribe If this conversation sparked something for you, share it with someone who's still trading time for dollars and wondering when things are going to change. Leon's story is proof that the answer isn't more hours — it's a different kind of income. Subscribe to Dealmaker Catalyst, leave a review, and keep showing up for the conversations that sharpen your edge. Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.

    23 min

  8. May 21

    Why Mobile Home Parks Are the Most Recession-Resistant Asset Most Investors Won't Touch | Major Hillard

    In this episode, host Jason Seward sits down with Major Hillard — founder of MH Estates and one of the most operationally experienced mobile home park investors in the country. Starting with just $1,500 and a dusty book found in his father's attic, Major built a $50 million-plus portfolio across 1,026 lots, sold 523 homes, and closed over $70 million in combined transactions. Major's story runs from crawling under frozen pipes at 2am as a kid watching his father burn out on residential rentals, to flipping mobile homes out of desperation, to deliberately targeting the ugliest parks nobody else wanted. His competitive edge was intentional: mastering the three financing linchpins that kill most mobile home park deals — vacancy, deferred maintenance, and park-owned homes — because becoming a specialist in what others avoided gave him his pick of the best opportunities. This episode covers creative deal structuring, niche specialization, fund investing, and why when the deal is good enough, the money will always find you.   What You'll Learn in This Episode How Major went from $1,500 and three jobs to $3,000 a month in cash flow within 90 days — and what that first mobile home flip actually looked like Why mobile home parks are the most recession-resistant asset in affordable housing — and why supply keeps shrinking while demand grows The three financing linchpins that kill most mobile home park deals — and why mastering them gave Major his pick of the best opportunities How to structure creative deals with no money down: seller financing, substitution of collateral, and the clam boat story that closed a $1.3M deal What separates a legitimate fund operator from a fee bandit — and the red flags to watch before putting your money anywhere   Timeline Highlights [1:03] – Introducing Major Hillard: $50M portfolio, 1,026 lots, and a $1,500 origin story [3:26] – Growing up on job sites with his father — and the 2am frozen pipe moment that made him say never again [4:25] – The Wall Street movie and why Major decided commercial real estate was the answer [5:08] – Starting as a commercial broker in 2008 — the worst possible timing — and managing a 126-unit Section 8 complex at 23 [6:16] – Three jobs, living at his parents' house, getting fired everywhere — and finding Deals on Wheels in a dusty attic box [8:16] – First mobile home flip: $1,500 in, sold in two weeks on installment sale, $3K/month cash flow within 90 days [9:00] – Why do one at a time when you can buy the whole park? The pivot that changed everything [10:14] – First park: listed at $750K, negotiated to $220K with seller financing and substitution of collateral [13:57] – No mentors, no community — mobile home parks were the black sheep of real estate in 2012 [14:25] – Why he deliberately targeted ugly parks: vacancy, deferred maintenance, and park-owned homes as a competitive advantage [21:30] – The clam boat story: four months of persistence, one in-person meeting, and uncovering the real motivation [23:34] – When the deal is good enough, the money will find you — and why big numbers are just an extra comma [29:14] – How knocking on 1,500 doors in commercial brokerage built the confidence that drives every deal today [33:06] – Why he tried multifamily, industrial, and residential before going all in on mobile home parks [34:45] – Affordable housing demand rises every year while supply shrinks — why that makes parks recession resistant [35:04] – All in or not in at all: why he sold everything after buying his first park [42:10] – How MH Estates Fund works: stabilized parks, predictable cash flow, and investor transparency [43:38] – Fee bandits: how to spot fund operators who collect fees and disappear when deals go sideways [44:26] – Why Major won't call a park stabilized until it's somewhere he'd live with his family [49:30] – Rapid fire: burn the ships, Unscripted, and why your current support system won't be there when you make it   Rapid Fire Highlights Favorite quotes: "Burn the ships." "You're either all in or you're not in at all." "If you want your life to change, you have to change things in your life." Dangerous early belief: That his current friends would still be there when he succeeded — many turned their backs when the wins came What he would not do again: Waste time not being confident — walk into every meeting ready to close, no matter what Key books: Deals on Wheels by Lonnie Scruggs, Unscripted by MJ DeMarco, Never Split the Difference by Chris Voss Red flag for any fund: If they're pushing courses and promotions hard, they're probably not doing well enough on deals   Resources Mentioned Elite Dealmakers community discounts: elitedealmakers.com/discount 608B Capital Funding — fix and flip, BRRRR, and value add lending plus a passive income debt fund for accredited investors: 608bcapital.com MH Estates Fund — Major Hillard's mobile home park investment fund (link in show notes) Deals on Wheels by Lonnie Scruggs Unscripted by MJ DeMarco Never Split the Difference by Chris Voss CCIM Institute — commercial real estate education Major recommends for anyone entering the space   Connect and Subscribe If this episode sparked something for you, subscribe, leave a review, and share it with someone who's serious about building their real estate legacy. New episodes every week.   Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.

    57 min
See All (17)

5
out of 5
26 Ratings

About

Join the Dealmaker Catalyst Podcast for real conversations with real estate investors and entrepreneurs. Learn how they approach deals, solve problems, and build their businesses. Every episode gives practical takeaways to help you make smarter moves in real estate.

Information

  • Creator
    Jason Seward & Jim Ingersoll
  • Years Active
    2K
  • Episodes
    17
  • Rating
    Clean
  • Copyright
    © 2026
  • Show Website
    Dealmaker Catalyst

You Might Also Like