Dealmaker Catalyst

In this solo episode, host Jason Seward steps away from the usual interview format to make an announcement: Dealmaker Catalyst is wrapping up its first season. Jason walks through the six months since the show launched in March, from hundreds of weekly downloads to standout guest conversations, and explains why the podcast is shifting from a weekly format to a seasonal one.

Jason gets honest about the real reason behind the change: his real estate investing business, 608B Capital, has scaled faster than expected, and hosting weekly interviews on top of running and growing that business has become tough to sustain. He shares what's ahead for season two, likely landing sometime in 2027, and invites listeners to reach out with guest ideas for what's next.

• Why Dealmaker Catalyst is wrapping up its first season after six months and hundreds of weekly downloads
• What led Jason to shift the show from a weekly release to a seasonal format of 8 to 10 episodes at a time
• How Jason's growing real estate business, 608B Capital, is driving the change in his schedule and priorities
• What listeners can expect from season two, including a likely 2027 launch window
• How to submit guest ideas or feedback for future seasons of the show

[0:16] – Jason opens solo and announces that Dealmaker Catalyst is wrapping up season one

[0:51] – Looks back at launching the show with Jim Ingersoll about six months ago with no long term plan beyond getting started

[1:12] – Reports hundreds of downloads a week and strong guest feedback since launch

[1:38] – Explains that Jim never wanted to host or conduct interviews himself, which is why Jason took on that role

[2:56] – Credits 608B Capital, his real estate business, for growing faster than expected

[3:27] – Says the bulk of his time now has to go toward building systems, processes, and his team at 608B Capital

[4:32] – Jason and Jim agree to move Dealmaker Catalyst to a seasonal format instead of a weekly release

[5:02] – Confirms this is the season one finale, with season two likely arriving sometime in 2027

[5:31] – Plans to release future seasons in blocks of 8 to 10 episodes to make scheduling easier

[5:54] – Makes clear the podcast isn't ending, just pausing between seasons

[6:14] – Calls out the previous episode with Laura Eubanks as a strong way to close out season one

[7:53] – Invites listeners to reach out to Jim or Jason with guest ideas or suggestions for future seasons

[8:15] – Thanks the audience and signs off until season two

• 608B Capital: https://608bcapital.com
• Elite Dealmakers Discount Program: https://elitedealmakers.com/discount

That's a wrap on season one. If you got value from these conversations, subscribe, leave a review, and share this episode with someone serious about leveling up before we're back with season two.

Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.

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.

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.

Jennifer Steward has spent the last decade doing something most real estate investors avoid entirely: personally cold calling off-market property owners, thousands of hours of it, until she'd built a repeatable system worth teaching. Today, she runs Phone Phoenix Agency, leading a team of more than 200 trained virtual assistants who handle cold calling, lead management, and appointment setting for investors and agents across the country, and is backed by more than 155 five-star reviews.

In this conversation with Jason Seward, Jennifer gets specific about what actually works in 2026: why listening for silence matters more than any script, why cold calling is real, unglamorous labor and not a passive income source, and the honest math behind what it costs and how long it takes to get your first deal. She also opens up about the poverty she grew up in and why she believes real resilience, not talent, is what separates the operators who make it from the 95% who don't. If you've been burning through marketing budget without a real system behind it, this episode is a grounded, no-fluff look at what it actually takes.

What You'll Learn in This Episode

• How to listen for silence on a sales call instead of filling every gap, and why that single habit changes your close rate
• Why cold calling is real, labor-intensive work rather than a passive income source, and what that means for your expectations
• What it actually costs and how long it takes to get your first deal, from $4,000 to $7,000 per deal and three to four months of spending before any income comes in
• Why "specificity of motive" is the real signal a seller is ready to sell, no matter what price they name
• How to structure a virtual assistant team, from a $540 a month starter package to a full-time hire, and what results to expect at each level
• Why making offers, not perfecting your comps, is the actual bottleneck holding most investors back from their first deal

Timeline Highlights

[0:16] – Introducing Jennifer Steward, founder of Phone Phoenix Agency and a 200+ person cold calling and lead management team

[2:37] – Jennifer's connection to Jim Ingersoll and Dealmaker, starting with a client named Lloyd on Upwork

[4:47] – Speaking at a Dealmaker event and watching her income and net worth grow six figures every time

[9:19] – Jennifer's path from cold caller to lead manager to quitting her W-2 job in April 2021

[13:38] – What most investors misunderstand about people: it's what they don't say, not what they say

[14:30] – The psychology of silence, and how the brain rewires around listening the way a blind person's does

[16:22] – The real numbers: one lead per eight-hour shift now versus five per hour before Covid

[17:14] – Why BatchDialer's reputation management feature is critical to actually reaching people

[19:36] – Why Jennifer stopped offering texting services after carrier shutdowns in August 2023

[22:09] – The sales mentor who taught Jennifer to shut up and let silence do the work

[28:42] – Why quality of leads has gone up even as quantity has gone down since Covid

[30:54] – Jennifer's own story of childhood poverty and why she believes it built her resilience

[34:48] – Why military veterans tend to be her most durable clients

[36:22] – When an investor should hire their first virtual assistant instead of cold calling themselves

[38:06] – The real cost of a deal: $4,000 to $7,000 depending on market, and 3 to 4 months before your first close

[43:43] – Why "specificity of motive" matters more than the price a seller names

[48:14] – What working with Phone Phoenix Agency actually looks like, from a $540 starter package to full-time

[54:23] – Why making offers, not perfecting your numbers, is what actually gets deals done

[59:37] – Jennifer's philosophy on legacy, and the mentor who taught her the abundance mindset

[1:03:27] – Closing thoughts and how to reach Jennifer directly

Resources Mentioned

• Phone Phoenix Agency — Jennifer's lead generation and virtual assistant company for real estate investors, wholesalers, and agents
• Jennifer Steward — contact by email at [email protected]
• BatchDialer — the dialer Jennifer's team uses, credited for its reputation management and number replacement features — https://batchdialer.com
• Rehab Valuator — the comps and deal analysis software created by Daniil Kleyman, which Jennifer has used for seven years — https://rehabvaluator.com
• X Leads CRM — referenced as a CRM that can automate offer sending; exact product name and URL could not be independently confirmed
• 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 there's one thing to take from this episode, it's Jennifer's line that the business you're in is the business of making offers. Go count how many offers you actually sent this month, and if the answer is zero, that's the fix before anything else. Share this episode with someone who keeps saying the leads aren't converting, and go check out Phone Phoenix Agency if you want a team like Jennifer's in your corner. 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.

Lindsey Jensen built a $12 million real estate portfolio in under eight years, and she did it as a brand new mom running a marketing business from home. In this episode she sits down with Jason Seward to explain how one weekend creative finance event in 2016 rewired her thinking, how she negotiated a first deal at 0% interest with nothing down, and why she chose to keep properties instead of flipping them. Today she runs over 70 doors on just a couple of hours a week.

What makes Lindsey different is the part most people skip. Plenty of gurus teach you how to buy a house. Lindsey teaches you how to own it without it owning you. She gets into the mentor who backstopped her early 50/50 deals, the master landlording systems she learned from David Tilney, the simple Trello setup her virtual assistant now runs, and how she is starting to use Claude to flag red flags on tenant applications. Underneath all of it is a bigger message: the grind is real in the building phase, and the freedom on the other side is the whole point.

What You'll Learn in This Episode

• How to reduce your risk on your first creative deals by partnering 50/50 with an experienced mentor
• Why consistency beats magic in marketing, and how a simple automated direct mail routine kept her pipeline full
• How to think like a leader, not just a landlord, so a good deal does not quietly turn into a bad one
• How to build a system simple enough that a virtual assistant or a non-technical contractor can run it
• Why the building phase demands a real grind, and how to systematize your way out of it
• How to start using AI to speed up tenant screening without handing over the final decision

Timeline Highlights

[1:02] – Meet Lindsey Jensen, a $12 million portfolio built in under eight years as a new mom

[2:46] – The weekend event in 2016 that introduced her to creative finance and blew her mind

[3:50] – The seller finance, subject to, and lease purchase deals that got her started

[4:32] – Why she partnered 50/50 with a mentor to insulate herself from risk early on

[5:48] – The sales background and Zig Ziglar lesson that made talking to sellers her superpower

[8:41] – Building around young kids, working during naps, and keeping the SEO business on autopilot

[10:11] – Why she focused only on the highest returns and refused to sweat the small stuff

[12:17] – The honest truth about the grind, and why "two hours a week" is not the whole story

[13:38] – Trying every marketing channel, and why she settled on automated direct mail

[15:33] – Why she never obsessed over cost per lead as a small, one person operation

[17:17] – Six months of looking at houses before her first deal, and the foundation it built

[18:53] – Choosing buy and hold over flipping, and the lifestyle book that shaped that call

[21:25] – Why being a great landlord, not just a great buyer, is her real strength

[22:01] – The landlording systems she learned from David Tilney, who learned from Jack Miller

[23:17] – The Trello system her virtual assistant runs, escalating only what needs her

[25:37] – Treating a virtual assistant as a true team member, and keeping them five plus years

[29:46] – Using Claude to surface red flags on tenant applications without giving a yes or no

[33:18] – Why she shifted her energy from grinding on properties to teaching others

[35:04] – Six courses plus one on one help, built by watching what actually worked for students

[37:24] – Why every student interviews with her first, so expectations are honest going in

[40:19] – The abundance mindset, coaching people in her own market, and there being enough for everyone

Resources Mentioned

• Clever Kitty Investing — Lindsey's courses, coaching, and systems training for building rental wealth — https://cleverkittyinvesting.com
• Trello — the simple, card based system Lindsey's assistant uses to run her landlording back end — https://trello.com
• Claude — the AI tool Lindsey uses to flag red flags on tenant applications — https://claude.ai
• 608B Capital — episode sponsor, a lender for fix and flip, BRRRR, and value add deals, with a debt fund for accredited investors — https://608bcapital.com
• Elite Dealmakers Discount Program — episode sponsor, nationwide discounts at Lowe's, Sherwin Williams, and more — https://elitedealmakers.com/discount
• Clever Kitty Investing on — YouTube: https://www.youtube.com/@cleverkittyinvesting, Instagram and TikTok — all under the handle @cleverkittyinvesting
• David Tilney — the landlording teacher whose master lease systems Lindsey learned and built on

Connect and Subscribe

If you have been sold the fantasy of zero down deals and two hour work weeks from day one, this episode is the honest correction you needed. Lindsey's whole approach is build the systems, lead your tenants, and let the freedom come on the other side of the grind. Go check out Clever Kitty Investing if you want to see how she teaches it, and share this episode with someone who is trying to build a portfolio without building themselves a second job. 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.