Dealmaker Catalyst

Augie Byllott has completed more than 600 real estate transactions using traditional bank financing only twice, built five businesses, and authored four books, but this conversation with Jason Seward centers on something else entirely: what he calls real estate's role as a "wheelchair," a vehicle that carries you toward a deeper purpose rather than an end in itself. Augie traces that idea back to a chance conversation with a colleague at Chase Manhattan Bank in 1982, and forward through a corporate retirement at 50, two years in seminary, and an unplanned pivot into full-time real estate and ministry after moving to Florida. The real focus of the episode is Chair the Love, the wheelchair charity Augie has directed since 2017, which has grown from delivering one shipping container of wheelchairs every two years to twenty containers, over 5,000 wheelchairs, in its best year. Augie shares specific, moving stories from distribution trips to Uganda and Kenya, breaks down exactly how donor dollars are spent, and introduces his own "Real Estate Challenge," donating a wheelchair for every closed transaction. If you've ever wondered what it looks like to build serious wealth and use it as a vehicle for something bigger, this conversation is a direct, personal answer.   What You'll Learn in This Episode How a chance conversation with a colleague in 1982 introduced Augie to buy and hold real estate Why Augie reframes retirement as a "four letter word" and what he does instead How Chair the Love sources, funds, and distributes wheelchairs to people in developing countries What percentage of donor dollars go directly to the mission, and how corporate partnerships stretch that further How to start small with generosity, using Augie's "one or two smiles a day" framework What the "Real Estate Challenge" is and how to build charitable giving directly into your transactions   Timeline Highlights [0:16] – Introducing Augie Byllott: 600+ deals, four books, and chairman of Chair the Love [4:01] – The wheelchair analogy for real estate as a vehicle, not a destination [9:49] – Meeting a colleague named Al at Chase Manhattan Bank in 1982 who changed everything [13:36] – Buying his first rental two years later, and house hacking before it had a name [17:32] – Setting a goal to retire at 50, and entering seminary in his mid-40s [19:12] – Moving to Florida and being pushed into full-time real estate and ministry work [20:33] – Helping homeowners facing foreclosure after 9/11 in Central Florida [22:34] – Redefining retirement: "It should be a four letter word" [31:36] – The first distribution trip that led him to Chair the Love [33:13] – Breaking down the numbers: a container equals 260 wheelchairs and about $52,000 [34:05] – Growth from one container every two years to twenty containers in a single year [36:19] – How Chair the Love selects countries and verifies genuine need [37:16] – A story from Uganda: delivering a wheelchair to a man named Stephen after a nine year wait [40:10] – How donor dollars are spent, and Chair the Love's roughly 80% efficiency rate [42:55] – Corporate partnerships with AdventHealth, Rotary Clubs, and the Philippine Red Cross [44:24] – Introducing the Real Estate Challenge: donating a wheelchair per closed transaction [52:06] – What the world would look like if success were measured by lives changed, not deals closed [59:42] – Starting small: the "one or two smiles a day" approach to building a habit of generosity [1:00:30] – Chair the Love's upcoming gala and golf outing, and where to learn more   Resources Mentioned Chair the Love: https://www.chairthelove.org The Virginia Investor Podcast (Augie's episode with Stephen Glover): https://podcasts.apple.com/us/podcast/the-virginia-investor-podcast/id1823747224 The 7 Habits of Highly Effective People by Stephen Covey 608B Capital: https://608bcapital.com Elite Dealmakers Discount Program: https://elitedealmakers.com/discount   Connect and Subscribe If Augie's wheelchair analogy hit you the way it hit Jason, take it as your own challenge: whatever vehicle you've built, business, real estate, deals, ask what it's actually driving you toward. Go check out Chair the Love if this got you thinking about where your own generosity could go, and consider building something like the Real Estate Challenge into your own transactions. Subscribe, leave a review, and share this episode with someone serious about leveling up. Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.  

Stephen Glover didn't grow up dreaming about property management, he fell into the industry in 2018 through a business partnership and had to learn the entire field from scratch. Today he's CEO and Principal Broker of Peak Property Management, one of the fastest growing property management firms in central Virginia, managing nearly 1,500 rental units across a team of almost 50 people, all built by staying disciplined about a small set of core values rather than chasing every opportunity that came his way. In this conversation with Jason Seward, Stephen breaks down exactly why property management has such a poor reputation industry-wide, and the simple fix his company built its entire culture around: responsiveness and communication, backed by prioritizing relationships and owning the outcome. He gets specific about the biggest mistakes landlords make, especially letting emotions override written screening and delinquency processes, and walks through the hidden costs of self-managing that never show up on a spreadsheet, from deferred maintenance to the sheer opportunity cost of an investor's own time. Stephen also covers several new Virginia-specific landlord laws taking effect, from an extended pay-or-quit period to new requirements around free payment methods, and shares his company's deliberate approach to AI: staying a powerful, human-led team backed by AI on the administrative back end, rather than racing to replace people with agents. He closes with a genuinely generous offer, Peak Property Management will provide free rental analysis and renovation advice to any investor in their market, whether or not they ever become a client. If you self-manage your rentals, are considering hiring a property manager, or are simply trying to figure out what separates a great operator from an average one, this episode is a direct, practical answer.   What You'll Learn in This Episode Why property management has a poor industry reputation, and the four core values Stephen built his company around to fix it The biggest mistake landlords make: letting emotions override written screening and delinquency processes The hidden, hard-to-calculate costs of self-managing, including deferred maintenance and the opportunity cost of your own time Why over-improving a rental for its neighborhood backfires, and how to get a free rent estimate before you renovate Several new Virginia landlord laws taking effect, including changes to pay-or-quit periods and required payment methods Why Stephen's company is staying human-led while using AI for back-end process automation instead of replacing people outright   Timeline Highlights [0:16] – Introducing Stephen Glover, CEO of Peak Property Management [2:17] – How a business partnership in 2018 led Stephen into an industry he knew nothing about [6:07] – Researching why property management has such a negative reputation [8:16] – The four core values built to fix it: responsiveness, communication, relationships, and ownership [11:22] – Peak Property Management's growth: from one team member to nearly 50, managing 1,500 units [13:25] – The biggest landlord mistake: letting emotions override your own written screening process [15:27] – The hidden costs of self-managing that never show up on a spreadsheet [17:42] – Weighing the value of your own time as an investor against the cost of a property manager [18:02] – A real story: a tenant's passing discovered while Stephen was on vacation, handled entirely by his team [19:12] – Another example: a fallen tree handled start to finish without Stephen lifting a finger [21:44] – Why over-improving a rental for its neighborhood backfires, using a real granite countertop example [24:10] – Why Stephen offers free rental analysis and renovation advice, even to non-clients [25:38] – New Virginia landlord laws: the pay-or-quit period extended from five to fourteen days [28:20] – The new requirement to offer tenants a free payment method [31:32] – Peak Property Management's philosophy on AI: human-led, AI-backed on the back end [35:23] – Why Central Virginia and Hampton Roads are outperforming national real estate headlines [39:32] – The property types Peak manages: sub-100 unit apartments and single family homes of any size [41:08] – Why short-term and mid-term rental management remains a "shiny object" they've deliberately avoided [42:07] – How to reach Stephen and Peak Property Management directly   Resources Mentioned Peak Property Management — Stephen's property management company serving central Virginia — https://www.richmondpropertymanagement.net The Virginia Investor Podcast — Stephen's own podcast interviewing investors and operators across Virginia — https://podcasts.apple.com/us/podcast/the-virginia-investor-podcast/id1823747224 608B Capital — episode sponsor, a hard money lender for fix and flip, BRRRR, and value add deals, plus a debt fund for accredited investors — https://608bcapital.com Elite Dealmakers Discount Program — episode sponsor, nationwide discounts at Lowe's, Sherwin Williams, and more for community members — https://elitedealmakers.com/discount   Connect and Subscribe If you're self-managing right now and telling yourself it's saving you money, Stephen's whole point is worth sitting with: what's the actual value of your time, and is this the highest and best use of it? Go reach out to Peak Property Management for a free rental analysis, even if you never plan to hire them, and share this episode with a landlord who's dealing with more deferred maintenance and vacancy than they'd like to admit. Subscribe, leave a review, and pass it along to someone serious about leveling up. Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.

Zach Shepard is only 24 years old, and he's already built a portfolio of roughly 240 to 255 rental units across central Virginia, spanning single family homes, apartments, small multifamily, and mobile home parks. He's the owner and operator of James River Rental Property, a vertically integrated investment and property management company based in Lynchburg, and his path there started with flipping saxophones on eBay as a 12-year-old, not a trust fund or a corporate career. In this conversation with Jason Seward, Zach traces the throughline from that saxophone business through flipping cars in college to leaving school at 19 to pursue business full time, buying his first property at 20, and the creative-finance deal that taught him you can use sweat equity as a down payment if you find the right local bank. He walks through how he scaled from 1 unit in 2023 to 6 in 2024 to nearly 90 acquisitions in 2025 against an audacious goal of 100, including four mobile home parks bought in a single month and a half. The conversation goes deep on how Zach actually sources deals, almost entirely through relationships and networking rather than direct-to-seller marketing, why he prefers direct ownership secured by real estate over syndications, and the underwriting rule he uses to stay conservative even while moving fast, keeping debt at roughly half of gross cash flow. He's also refreshingly candid about imposter syndrome, family priorities, and what legacy means to him at 24 with two young kids at home. If you've ever wondered what it actually takes to compress decades of real estate growth into just a few years, without cutting corners on family or ethics to get there, this episode is a genuinely rare look at how that's being done in real time.   What You'll Learn in This Episode How to use sweat equity and a rising appraisal as a down payment through the right local bank Why the highest-value activity in deal sourcing can be as simple as consistently getting lunch with other investors How to set audacious, barely-believable goals and reverse engineer them into monthly targets Why direct ownership secured by real estate can be a safer position than passive syndication investing What underwriting rule keeps a fast-growing portfolio conservative: debt at roughly half of gross cash flow How to build a team and systems that let a business keep running well even when you step away   Timeline Highlights [0:16] – Introducing Zach Shepard: 240 units across Virginia by age 24 [1:56] – Zach's connection to Jim Ingersoll and the Dealmaker community [3:20] – Leaving college at 19 to pursue business, and the mentor who gave him his shot in sales [6:20] – The saxophone flipping business that taught him value-add thinking as a teenager [9:39] – Learning that wealth is knowledge, and how that showed up in cars, then real estate [12:03] – The first creative finance deal: turning sweat equity into a 20% down payment [17:12] – Partnering with an investor to buy four houses together, and the momentum that followed [18:29] – Scaling from 1 unit in 2023 to 6 in 2024 to a goal of 100 in 2025 [22:34] – Reading Grant Cardone's The 10X Rule and setting a goal that felt almost unbelievable [26:05] – Why deal sourcing became almost entirely about networking and relationships [27:35] – Buying a 32 unit portfolio directly from another investor using seller finance and DSCR loans [28:06] – The current team: two property managers, a project manager, and a maintenance lead [29:30] – The underwriting rule: keeping debt at about half of gross cash flow across the portfolio [31:16] – Why Zach prefers direct, real estate secured ownership over syndication [33:28] – Navigating imposter syndrome at 24, and the faith perspective that grounds him [38:45] – Prioritizing marriage and family, including no work on Sundays and no missed dinners [42:43] – What legacy means to Zach: raising his boys and prioritizing impact over personal recognition [44:26] – How to reach Zach: his buy box, his website, and how listeners can connect   Resources Mentioned James River Rental Property — Zach's vertically integrated real estate investment and property management company — https://www.jamesriverrentalproperty.com The 10X Rule by Grant Cardone (referenced as the book that shaped Zach's goal-setting approach) 608B Capital — episode sponsor, a hard money lender for fix and flip, BRRRR, and value add deals, plus a debt fund for accredited investors — https://608bcapital.com Elite Dealmakers Discount Program — episode sponsor, nationwide discounts at Lowe's, Sherwin Williams, and more for community members — https://elitedealmakers.com/discount   Connect and Subscribe If you needed a reminder that big goals are worth setting even when you don't fully believe you'll hit them, Zach's story is that reminder. Go set the goal that scares you a little, then go find out how far short of it still puts you ahead of where you'd have landed playing it safe. If you've got a deal, a portfolio, or capital to invest within a couple hours of Lynchburg, Virginia, reach out to Zach directly. Subscribe, leave a review, and pass this along to someone serious about leveling up. Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.  

Isabelle Guarino runs one of the only education companies teaching a real estate niche most investors have never even considered: residential assisted living. As CEO of Residential Assisted Living Academy, she's spent over a decade helping investors convert large single family homes into licensed senior care residences, a business her late father Gene started years ago and passed on to her. In this conversation with Jason Seward, Isabelle breaks down exactly how the model works: a large single family home, housing 6 to 16 seniors, staffed by licensed caregivers the owner hires but never personally cares for residents themselves. She lays out the demographic case for the space, driven by the aging baby boomer population and a 1.3 million bed shortage nationwide, and walks through the three ways to get involved, owning and leasing the real estate, being a private lender or JV partner, or owning both the real estate and the operating business. Isabelle gets specific about the numbers too: what size and type of home to look for, the demographic profile of the surrounding neighborhood that actually matters most, how SBA 7(a) and 504 loans can fund the real estate, renovation, and carrying costs all in one package, and real monthly cash flow figures from her own ten-bed home in Phoenix. She's candid about why the space isn't more mainstream yet, from liability fears to the capital required to get started, and shares the personal story behind why she's built her business around education rather than keeping the model to herself. If you've been looking for a real estate niche that isn't oversaturated with gurus, backed by demographics that aren't going anywhere for the next 20 years, this episode is a genuinely different conversation than most you'll hear in this space.   What You'll Learn in This Episode How residential assisted living actually works: a licensed single family home with 6 to 16 residents and hired caregivers, not a large commercial facility Why the demographic case for this niche is unusually strong, with a 1.3 million bed shortage and 76 million baby boomers entering the market over the next 20 years The three ways to get involved: owning and leasing the real estate, private lending or JV partnering, or owning both the real estate and the operating business What size home, neighborhood demographics, and financing structure (including SBA 7(a) and 504 loans) actually work for this model Real monthly cash flow numbers from an operating ten-bed home, and how the business itself gets valued and sold separately from the real estate Why liability fears and capital requirements keep this niche from being oversaturated, and how to mitigate the real risks   Timeline Highlights [0:16] – Introducing Isabelle Guarino, CEO of Residential Assisted Living Academy [1:34] – Why residential assisted living isn't the mainstream niche most investors expect [2:05] – What the model actually is: a licensed single family home, not a commercial facility [4:19] – The demographic case: 76 million baby boomers and a 1.3 million bed shortage [5:35] – Whether it's too late to get into the space, and why the numbers hold for 20 more years [7:53] – Why smaller homes offer dramatically better care and response times than large facilities [10:20] – The three ways to get involved: landlord, private lender, or owner-operator [12:26] – What size and type of home to look for, and how to convert it [14:11] – The neighborhood demographics that actually predict a good location [15:23] – Financing the deal with SBA 7(a) and 504 loans, including renovation and carrying costs [17:17] – Real cash flow numbers from a ten-bed home: $60K in, $10K net per month [18:49] – How to structure an exit: selling the business, the real estate, or both [20:14] – Why this niche isn't more mainstream: liability fears, capital requirements, and myths [24:01] – How passive investors can get involved through syndications and private lending [25:19] – Why finding a coach or mentor matters, and the origin story of RALA's education arm [29:37] – Jason's own mentor story, and the abundance mindset behind teaching competitors [32:18] – Where to learn more: RAL101.com, in-person events, and the Assisted Living Network Podcast   Resources Mentioned RAL101.com — free training, books, webinars, and how to schedule a call with Isabelle's team — https://ral101.com Residential Assisted Living Academy (RALA) — Isabelle's education company, hosting in-person events roughly every 6 to 8 weeks in Phoenix — https://residentialassistedlivingacademy.com The Assisted Living Network Podcast — Isabelle's podcast, new episodes every Friday Living Legacy by Isabelle Guarino — her book on investing in residential assisted living 608B Capital — episode sponsor, a hard money lender for fix and flip, BRRRR, and value add deals, plus a debt fund for accredited investors — https://608bcapital.com Elite Dealmakers Discount Program — episode sponsor, nationwide discounts at Lowe's, Sherwin Williams, and more for community members — https://elitedealmakers.com/discount   Connect and Subscribe If you've been looking for a real estate niche that isn't already flooded with gurus, this episode is worth a second listen with a notebook out. Isabelle's whole business is built on the idea that there's enough opportunity for everyone, so go check out RAL101.com if this got you curious about a space most investors never even consider. Share this episode with someone diversifying into new real estate niches, subscribe, leave a review, and pass it along to someone serious about leveling up. Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.  

Jason Balin has been in the private lending business for nearly two decades, co-founding Hard Money Bankers with his business partner Chris Haddon back in 2007, when there was almost no organized competition in the space. In this conversation with Jason Seward, he steps back from loan mechanics to talk about private lending as an actual business, the kind of decisions that separate a sustainable operation from one that quietly implodes years down the road. Jason walks through the origin story: how a single bad flip taught him that the lender made more money than the flippers did, and how that realization led him and Chris to start a hard money company with no capital of their own and no real playbook to follow. He gets specific about the co-lending model they still use today, why they've deliberately kept their portfolio around $50 million instead of scaling to $75 or $80 million, and the pricing philosophy he picked up in a Russell Brunson mastermind a decade ago: be the most expensive or the cheapest, never stuck in the middle. The conversation goes deep on risk, including a live example of a loan currently sitting in default for over three years, the real cost of chasing deal flow irresponsibly, and why Jason believes so many newer private lenders are quietly heading toward financial trouble because they don't understand that this business is not passive if you're the one operating it. He also breaks down an underused opportunity most new lenders overlook entirely: small balance commercial loans and cash-out loans to buy-and-hold landlords, not just fix and flip investors. Toward the end, Jason talks about the Hard Money Mastermind he and Chris built almost by accident, now home to over 2,600 members, and why they intentionally screen every applicant rather than let anyone buy their way in. If you've ever thought about becoming a private lender, or you're already lending and wondering if you're doing it sustainably, this is a masterclass from someone who's seen nearly every version of this business succeed and fail.   What You'll Learn in This Episode Why one bad flip, where the lender made more than the investors, was the moment that redirected an entire career How to structure a co-lending model where capital partners are the lender of record and you retain servicing Why staying deliberately smaller can be more profitable than chasing portfolio growth Why pricing in the middle of the market is the most dangerous place to be as a lender How to identify the small balance commercial and buy-and-hold cash-out opportunities most lenders ignore Why treating this as a passive investment, instead of an active business, is what quietly bankrupts new private lenders   Timeline Highlights [1:02] – Introducing Jason Balin, co-founder of Hard Money Bankers since 2007 [2:09] – Why Jason and his partner stayed hyper-localized to Maryland, DC, and Virginia [4:00] – The five house flips before the lending company, and the deal that changed everything [6:05] – Realizing the lender made more money than the flippers, and deciding to become the lender [9:23] – Raising capital from people they barely knew, using warm referrals instead of cold outreach [13:31] – The co-lending model explained: capital partners as lender of record, Hard Money Bankers as servicer [20:32] – Why institutional capital flooded into private lending over the last five to ten years [22:04] – The "most expensive or cheapest" pricing philosophy from a Russell Brunson mastermind [28:16] – Why they've deliberately stayed near a $50 million portfolio instead of scaling further [32:51] – The danger of copying an institutional lender's model without seeing their real economics [38:00] – A live example: a loan stuck in default for over three years and the true cost of it [43:24] – Why skin in the game from the borrower changes how hard they'll fight to save a deal [45:34] – Why treating this as a passive income source is the single biggest mistake new lenders make [47:14] – The small balance commercial and cash-out lending opportunities most lenders overlook [48:39] – The origin story of Hard Money Mastermind and why they intentionally screen every applicant [58:07] – A story from March 2020, and why changing your criteria beats quitting the business entirely [1:02:25] – Closing thoughts and how to connect with Jason Balin and Hard Money Bankers   Resources Mentioned Hard Money Bankers — Jason and Chris's private lending company, based in Columbia, Maryland — https://www.hardmoneybankers.com Private Lenders' Podcast — hosted by Jason Balin and Chris Haddon — https://podcasts.apple.com/us/podcast/private-lenders-podcast/id1476153070 Real Estate Reserve Podcast — Jason's second podcast Hard Money Mastermind — the community for private lenders looking to grow their own lending businesses — https://www.hardmoneymastermind.com 608B Capital — episode sponsor, a hard money lender for fix and flip, BRRRR, and value add deals, plus a debt fund for accredited investors — https://608bcapital.com Elite Dealmakers Discount Program — episode sponsor, nationwide discounts at Lowe's, Sherwin-Williams, and more for community members — https://elitedealmakers.com/discount   Connect and Subscribe If you've ever thought about becoming a private lender, or you already are one and something about your business feels a little too passive, go back through this episode with a notebook. Jason's whole message is that this only works if you treat it like the active business it actually is. Share this one with anyone sitting on capital and wondering how to put it to work responsibly, and go check out the Private Lenders' Podcast if you want to keep learning directly from Jason and Chris. Subscribe, leave a review, and pass it along to someone serious about leveling up. Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.