In this special recap episode, Jason Seward sits down with Jim Ingersoll, the founder of the entire Dealmaker community, to look back on some of the standout guests and lessons from recent episodes. They revisit Zach Shepard's early hustle flipping saxophones, Lori Eubanks' fearless approach to opportunity, and the father son story of Chuck and Stephen Glover, while Jim shares his own early hustle buying clearance golf balls at Walmart and reselling them on eBay. The conversation also covers real community news. Dealmaker's local meetups are expanding into new markets like Palm Beach, while Hampton Roads shifts toward quarterly daytime events to protect family time. Jason shares an update on his own investment fund reopening to new accredited investors, and Jim closes with a grounded, practical take on navigating today's interest rate environment. If you have been following the guests on this show, this episode connects the dots between many of their stories and the community that made them possible. Timeline Highlights [0:44] Jim's philosophy on why hearing a guest's losses matters more than hearing only their wins [2:56] Revisiting Zach Shepard's origin story flipping saxophones as a teenager [4:38] Jim's own early hustle. Buying clearance golf balls at Walmart and reselling them on eBay [6:59] Reflecting on Isabelle Guarino's memory care model and creative cash flow strategy [7:38] A teaser about Lori Eubanks' newest big project and a story involving a Michael Jordan property [9:31] The story of Lori meeting a lifelong friend by chance at her very first Dealmaker event [10:21] Revisiting the father son story of Chuck and Stephen Glover [16:41] Jim shares a personal update from a recent visit with a Dealmaker meetup leader in Jackson [19:03] Restructuring the Hampton Roads meetup into a quarterly daytime conference to protect family time [20:20] Community updates. Breakfast meetups in Charlotte and new meetups launching in Palm Beach [21:36] Advice for listeners who want to start a Dealmaker meetup in their own market [23:25] Sharing real numbers from the Dealmaker discount programs with Lowe's and Sherwin Williams [27:12] Jason shares an update on his own investment fund reopening to new accredited investors [31:25] A grounded take on today's interest rate environment and how to stay unafraid of the math [34:08] Why seller financing can make today's interest rates almost irrelevant to a deal Rapid Fire Highlights Favorite recent guest stories: Zach Shepard's saxophone flipping origin story, Lori Eubanks' fearless approach to opportunity, and the father son dynamic between Chuck and Stephen Glover Community wins: Hampton Roads restructuring toward quarterly daytime events, new meetups launching in Palm Beach, and a breakfast format taking off in Charlotte Practical advice shared: do not let fear of rising rates paralyze a fundamentally sound deal, and seller financing can make the current rate environment far less relevant Resources Mentioned Dealmaker Meetups: https://dealmakermeetups.com 608B Capital: https://608bcapital.com Elite Dealmakers Discount Program: https://elitedealmakers.com/discount Connect and Subscribe If any of the guests referenced in this episode caught your attention, most of their full episodes are already in the feed, so go back and give them a listen. This community only works because people like you show up, share it, and bring in the next great guest, so if you know someone with a story worth telling, reach out. 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.
Lori Eubanks started investing in real estate in 2012 as a single mother on one income, looking for any way to make ends meet. Since then she's built a portfolio of more than 120 properties across Richmond, Virginia, using seller financing, strategic partnerships, and a habit of buying properties in bulk rather than one at a time, all while raising three kids and eventually retiring from her corporate job at 33. In this conversation with Jason Seward, Lori breaks down the mindset and relationships that took her from "just find one deal to survive" to buying ten-property portfolios in a single transaction, her simple underwriting rule of staying at or under 70% loan to value, and how she protects her family time as a non-negotiable boundary. She closes by sharing her newest, biggest project yet: a memory care, assisted living, and independent living campus she's building with her partner, funded through seller financing and, in part, by Jason's own lending company. What You'll Learn in This Episode How to go from "figure it out" survival mode to buying property portfolios ten at a time Why leading with "how can I help you" builds stronger mentor relationships than simply asking to be mentored A simple way to stress test any deal: shop it to four or five hard money lenders and see who says yes The 70% loan-to-value rule and $300-per-door cash flow threshold Lori uses to decide what to keep as a rental How to protect family time and mental health as a fast-growing portfolio and business scale up How opportunity zones and refinancing can turn a growing rental portfolio into a tax-advantaged wealth engine Timeline Highlights [0:16] – Introducing Lori Eubanks: 120+ properties built through creative and seller financing [3:25] – The trigger into real estate: single income, three young kids, and a free local investor meetup [4:39] – Leading with "how can I help you" instead of asking to be mentored [6:04] – The first flip that became a rental, and the mind shift toward buying portfolios [8:12] – Ryan Mellon, the friend who pushed Lori to think bigger and ask for seller financing [10:41] – Why leading with value, not just asking for help, made people want to mentor her [16:01] – Advice for new investors: stop overanalyzing and lock deals up under contract first [17:53] – Starting low: offering half the asking price and getting comfortable with rejection [18:20] – The stress test: shop a deal to four or five hard money lenders and see who says yes [19:23] – Retiring from her corporate job at 33 after her rental income replaced her salary [22:06] – The anxiety of leaving a stable paycheck, and rebalancing the portfolio to keep a safety net [26:40] – Lori's underwriting rule: 70% loan to value, and $300 per door in cash flow to keep as a rental [29:45] – Passing deals to trusted friends when the numbers don't fit her own portfolio [30:10] – Protecting family time: a hard stop on business talk after 6pm [34:10] – Why business is a tool for family memories, not the priority itself [35:30] – How buying a mansion as a family gathering space changed her kids' view of real estate [38:11] – Introducing the new project: a memory care, assisted living, and independent living campus [41:27] – How Jason's own lending company ended up financing the additional land next door [44:36] – Closing thoughts and how to connect with Lori directly Resources Mentioned Vitalized Properties: https://www.linkedin.com/in/lori-eubanks-58181031 608B Capital: https://608bcapital.com Elite Dealmakers Discount Program: https://elitedealmakers.com/discount Connect and Subscribe If you've been stuck trying to figure out the "right" strategy before making a move, Lori's whole story is proof that locking up a deal and figuring it out along the way works better than waiting for certainty. Go build the kind of relationships where you lead with value, not just an ask, and watch how much faster doors open. 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.
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.