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In this episode, host Jason Seward sits down with Alie Murphy — business operations strategist, consultant, and founder of Let's Talk Business — for a practical deep dive into the bottlenecks that stall most growing businesses and the systems that break them open.
Alie helps founders turn chaos into clean, scalable operations. Her background spans healthcare administration, real estate, and high-growth startups, and her no-nonsense approach to CRMs, delegation, and execution has helped business owners scale without burning out or resenting what they built. She and her husband Corey live proof of the model — traveling the country following their daughter's rodeo career while their business runs cleanly behind them.
This episode covers the most common bottlenecks founders face, why ego is the biggest obstacle to delegation, how to do a time audit that clears 50% of your calendar, and what it actually means to build a business to sell — even if you never plan to. Alie also opens up about letting go of profitable businesses that didn't fit the life she wanted, and why shrinking her business made it more successful and set her free.
What You'll Learn in This Episode
Timeline Highlights
[1:03] – Introducing Alie Murphy and her background in operations and business consulting
[3:52] – How Alie and her husband built their life around systems — traveling for their daughter's rodeo career while the business runs without them
[4:16] – Why documenting everything from day one changes what you can hand off later
[8:05] – The two biggest bottlenecks: doing everything yourself and not setting boundaries
[9:13] – Why most entrepreneurs use their CRM as a storage facility — and what they're leaving on the table
[10:19] – Shiny object syndrome: why jumping platforms is often just expensive procrastination
[11:34] – How to think about the ROI of hiring help before you feel like you can afford it
[13:23] – Hunt rabbits, don't cook them: the mindset shift that unlocks your first real delegation decision
[15:21] – The fear of hiring: what happens when your failure starts affecting someone else's livelihood
[18:00] – Step-by-step task handoff: how to document a process so completely that anyone can run it
[21:51] – The time audit: two weeks, every 15 minutes — and how it cleared 50% of one founder's calendar
[23:49] – Why most entrepreneurs grind without a clear vision of what they're actually building toward
[26:08] – Building businesses that didn't fit her life — and letting them go to build something she could actually live
[28:54] – Why scaling back revenue sometimes is the step forward no one talks about
[30:20] – Going deeper on your why: what "my family is my why" actually means — and when it becomes a cop out
[35:41] – How ego shows up in every founder's journey — and why people who aren't ready to let go can't be helped yet
[37:35] – When to hire a consultant versus an employee — and why assistants should never be outsourced
[39:33] – Rapid fire: holy discipline is the highest form of self-respect
[40:00] – Dangerous early belief: working harder is the answer. It's not.
[40:34] – What she gave up: clients and relationships that didn't fit — and how releasing them unlocked her growth
[42:14] – What she would not do again: scaling before the systems were ready
[43:51] – Defining failure: scaling something that wasn't ready — the pressure, inconsistency, and constant fires that stole her peace
Rapid Fire Highlights
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Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.
In this episode, host Jason Seward sits down with Major Hillard — founder of MH Estates and one of the most operationally experienced mobile home park investors in the country. Starting with just $1,500, Major built a $50 million-plus portfolio across 1,026 lots, sold 523 homes, and closed over $70 million in combined transactions — all by specializing in the ugly, underperforming parks nobody else wanted.
Major's story runs from crawling under frozen pipes at 2am as a kid watching his father burn out on rentals, to flipping mobile homes out of desperation with his last $1,500, to engineering a $1.3 million loan approval with a fake proof of funds document that cost him $500. He learned everything trial by fire, without mentors or a community, and built a framework around the three deal-killing variables in mobile home park financing — vacancy, deferred maintenance, and park-owned homes — because mastering what others avoided gave him his pick of the best deals. This episode covers creative deal structuring, niche specialization, fund investing, and why the money always finds a deal that's good enough.
What You'll Learn in This Episode
Timeline Highlights
[1:03] – Introducing Major Hillard: $50M portfolio, 1,026 lots, and a $1,500 starting point
[3:26] – Growing up on job sites with his father — and the 2am frozen pipe moment that made him say never again
[4:25] – The Wall Street movie, Michael Douglas, and why Major decided commercial real estate was the answer
[5:08] – Starting as a commercial broker in 2008 — the worst possible timing — and managing a 126-unit Section 8 complex at 23
[6:16] – Three jobs, living at his parents' house, getting fired everywhere — and finding Deals on Wheels in a dusty box in the attic
[8:16] – First mobile home flip: $1,500 in, sold in two weeks on installment sale, cash flow within 90 days
[9:00] – The moment he realized: why do one at a time when you can buy the whole park?
[10:14] – First park acquisition: listed at $750K, negotiated to $220K with seller financing, 40-year amortization, and substitution of collateral
[13:57] – Why mobile home parks were a black sheep niche — no mentors, no community, learning everything alone
[14:25] – Why he deliberately targeted the ugly parks: vacancy, deferred maintenance, and park-owned homes were his competitive advantage
[22:00] – The clam boat story: four months of persistence, one in-person meeting, and uncovering the seller's real motivation
[23:12] – How Major got approved for a $1.3M loan with a fake proof of funds that cost him $500
[25:14] – Closing with no money down — and receiving a $20,000 check at closing. That property sold 36 months later for $3.3M
[26:25] – The rule that guided every deal: when it's good enough, the money will find you
[34:59] – Why he tried multifamily, industrial, and residential before going all in on mobile home parks
[36:32] – Why affordable housing demand rises every year while supply shrinks — and why that makes parks recession resistant
[37:15] – You're either all in or you're not in at all — why he sold everything else after buying his first park
[43:00] – How MH Estates Fund works: stabilized parks, predictable cash flow, and investor transparency
[45:02] – Fee bandits: how to spot fund operators who collect fees and disappear when deals go sideways
[47:03] – Why Major won't call a park stabilized until it's somewhere he'd live with his family
[51:41] – Rapid fire: burn the ships, Unscripted by MJ DeMarco, and why your network will change as you grow
Rapid Fire Highlights
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Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.
In this episode, host Jason Seward sits down with Tom Olson — licensed general contractor, investor, developer, and founder of multiple real estate businesses operating out of Gary, Indiana. With over 2,000 transactions, 1,200-plus flips, 700 investor rentals, and 45 mid-term rentals under management, Tom has built one of the most vertically integrated real estate operations in the Midwest — and he did it with a mission at the center: flip the city of Gary, Indiana, and make it a place people move to instead of from.
Tom's story starts at 12 years old swinging hammers, runs through the 2008 crash that took him from $120K to $20K in income overnight, and culminates in a multi-company empire guided by clear core values, business operating systems, and asset leaders running each vertical. This episode covers business structure, goal setting, knowing your numbers, the danger of scaling too fast, and why most real estate investors are solopreneurs masquerading as business owners.
What You'll Learn in This Episode
Timeline Highlights
[1:03] – Introducing Tom Olson: 2,000+ transactions, 1,200 flips, and a mission to transform Gary, Indiana
[3:13] – How Tom and Jim Ingersoll met on an IRA cruise — and discovered they were both from Jamestown, New York
[9:04] – Starting in construction at 12 years old and why he never wanted to let it go
[9:48] – How Rich Dad Poor Dad introduced him to the idea of cash machines — and sparked his investing journey
[12:01] – The 2008 crash: going from $120K to $20K overnight and making cold calls for the first time
[12:35] – The investor who told him he was the first contractor in 30 years to show up on time, quote on the spot, and finish on budget
[14:54] – Wholesaling 1,300 to 1,400 homes between 2009 and 2015 with a partner
[15:12] – How the partnership split led to building every vertical himself: construction, property management, brokerage, and lending
[18:31] – Why not everyone should have 11 businesses and 43 employees — and why that's okay
[19:41] – Scaling Up and Traction: the two books that changed how Tom ran his companies
[21:26] – Which businesses are actually sellable assets and which are just jobs with an LLC
[24:06] – Moving his family to Gary, Indiana during the crash — and the moment God gave him the vision to flip the city
[26:24] – Why every business decision must fit inside two goals: give to missions and transform Gary
[29:05] – SMART goals, quarterly rocks, and why you should never reach all your goals
[33:43] – Core values as a hiring filter: charity, stewardship, community, growth — and the 20-minute onboarding video that weeds people out
[37:05] – The three departments every business has: sales, operations, and admin — and why sales is always most important
[39:59] – Why payroll over 50% of gross profit is a warning sign you cannot ignore
[43:42] – The two reasons businesses fail: not knowing numbers and scaling too fast
[49:52] – Why scaling too fast turns businesses into Ponzi schemes — and how to know when to hit the brakes
[54:11] – What real profit actually means: you've been paid back, the business pays you a salary, and it's consistently profitable quarter after quarter
Rapid Fire Highlights
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Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.
In this episode, host Jason Seward sits down with Dr. David Phelps — dentist turned real estate investor and founder of Freedom Founders — for a conversation about what it really takes to break free from a high-income career that's quietly running your life.
David's story starts in 1980 when, as a broke first-year dental student, he convinced his father to co-invest in a rental property at a 30.5% mortgage rate. That deal split $50,000 four years later and planted a seed that grew alongside his dental career for two decades — until his daughter's health crisis forced the question: do I have enough passive income to step away? He did. That moment is at the heart of everything he now teaches through Freedom Founders, a mastermind built specifically for dentists, doctors, lawyers, and other professionals trapped in what he calls the golden handcuffs.
Jason and David cover the mindset shift from Wall Street defaults to self-directed investing, how to evaluate masterminds without getting burned, how to vet passive investments without losing all oversight, and why patience and liquidity matter more right now than chasing the next deal.
What You'll Learn in This Episode
Timeline Highlights
[1:03] – Introducing Dr. David Phelps and his path from dentistry to financial freedom
[4:51] – Why real estate was on his radar before dental school — reading investing books in college
[6:18] – The golden handcuffs: why high-income professions feel like security but demand everything
[7:30] – His first deal in 1980 at 30.5% interest — and the $50,000 gain that changed his thinking
[11:26] – The golden handcuffs defined: earning well while trapped on a hamster wheel
[12:20] – Would he do it differently today? What he'd tell an 18-year-old about college and credentials
[15:29] – The shift from hands-on investing to passive — and what you give up in each direction
[16:28] – His daughter's health crisis: the moment that forced the question of whether he had enough
[17:14] – Why time eventually becomes the most valuable commodity — and how assets buy it back
[19:43] – The first step for a high-earning professional: slow down before going tactical
[23:02] – What separates a real mastermind from a glorified networking club
[27:28] – How Freedom Founders helps members vet passive deals: checklists, community review, shared due diligence
[30:35] – How to evaluate any investment operator: the best ones lead with the nightmare scenario first
[31:30] – David's take on the current environment: liquidity, patience, and waiting for better opportunities
[33:09] – The K-shaped economy and why W-2 earners are falling further behind asset holders
[35:19] – Why location matters more than ever: landlord laws, political environment, and where he won't invest
[37:43] – What Freedom Founders looks like: live events, business succession frameworks, and next-generation planning
Rapid Fire Highlights
Resources Mentioned
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Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.
In this episode, host Jason Seward sits down with Eddie Speed — founder of Note School and one of the most experienced note investors in the country — for a high-level introduction to a corner of real estate that most investors have heard of but few fully understand. Eddie has been buying mortgage notes for over 45 years, has been involved in more than 50,000 note transactions, and built an entire educational platform to help investors learn what he learned the hard way starting in 1980 as a broke cowboy in Mississippi mentored by the man who would become his father-in-law.
The premise of this episode is simple but powerful: the landlord gets paid last. After the bank, the insurance company, the tax authority, the plumber, the roofer, and the property manager all take their cut, the landlord nets whatever is left. The note investor gets paid first — every month, without tenants, without toilets, and without the management overhead that slowly erodes rental margins. In a market where fix and flip margins are shrinking, multifamily is under pressure, and inflation has cut rental cash flow nearly in half for many investors, Eddie makes a compelling case that now may be the best time in decades to be the bank instead of the landlord.
Jason and Eddie walk through how notes work, how to source and underwrite them, how to finance note purchases without needing all the capital yourself, what happens when borrowers default and why a cushion factor makes it manageable, and why using a licensed loan servicer removes most of the administrative burden entirely. This episode won't make you a note investor overnight, but it will open a door most investors didn't know existed — and point you directly toward the resources to walk through it.
What You'll Learn in This Episode
Timeline Highlights
[1:04] – Introducing Eddie Speed and his 45-year career in note investing
[2:50] – How Eddie accidentally got started: a fireman father-in-law in Mississippi who figured out notes beat rentals during inflation
[5:03] – Defining note investing in its simplest form: becoming the bank
[6:39] – Why market timing makes notes compelling right now — multifamily, flipping, and rentals are all under pressure
[9:22] – The landlord gets paid last — the note investor gets the first money every month
[10:06] – How Eddie sources notes: 45 years of brand, marketplace relationships, and 22,000-plus portfolios purchased
[11:48] – The Lexus pre-owned checklist: how Eddie's due diligence framework removes the biggest barrier for new note investors
[13:36] – Mechanics of buying a note at a discount: what you paid doesn't change what you're legally entitled to collect
[15:25] – Why burnout landlords are flooding into note school — and how seller financing can increase net income 2.5x on the same house
[17:43] – How to fund note purchases: you don't need the money in your checking account
[19:44] – Using other people's money, retirement accounts, and fund structures to scale note investing
[20:41] – What happens when borrowers default: why the cushion factor means you're usually okay
[23:28] – Why every note Eddie sells goes to a licensed loan servicer — and why you should not service it yourself
[25:43] – How note investing compares to owning rentals with a property manager: you're involved in a tenth of the decisions
[27:14] – What to expect from Note School: the podcast, YouTube channel, and the free starter series built for Dealmaker listeners
[30:21] – Jason's parallel: how getting curious about lending led him down the path to running a fund
[30:45] – Rapid fire questions begin
[31:07] – Favorite principle: compound interest — the eighth wonder of the world
[31:37] – The dangerous early belief: that he couldn't buy notes because he was broke
[32:00] – What success cost him: growing faster than his infrastructure could handle
[32:38] – What he would refuse to waste time on again: not knowing who to spend time with — he now knows exactly how to find the right people
[33:23] – The mistake that still shapes how he underwrites risk: junk property. Good people will default on a bad neighborhood to protect their family.
[34:29] – What most investors misunderstand about money: earning interest — run the math and it changes everything
Rapid Fire Highlights
Resources Mentioned
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Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.
In this episode, host Jason Seward sits down with Tony Moreno — mechanical engineer, real estate investor, and Huntsville, Alabama-based father of one — for a conversation that is equal parts origin story and tactical playbook. Tony was born in the Dominican Republic, moved to Cleveland at nine, bounced back to the DR, and eventually landed in Huntsville when his father Googled "best places to live in America" in 2009 and went with the number one result. That same methodical, engineer-minded approach now drives everything Tony does in real estate.
Tony's entry point was a moment of clarity at his first engineering job, working 60-plus hours a week in automotive manufacturing, realizing no job title or salary would ever give him what he was actually after: control, purpose, and time. A single book — Rich Dad Poor Dad, read during Thanksgiving break 2019 — lit the fuse. What followed was a deliberate, step-by-step progression: studying the fundamentals, analyzing 300 properties at ten per day before ever making an offer, cobbling together capital from a car lien and a 401K withdrawal, and closing his first two deals in the middle of a pandemic.
Since then Tony has navigated the 2021 frenzy by pivoting into subject-to deals, expanded into mobile home parks, and is currently underwriting a 24-unit apartment complex — all while maintaining his W-2 and supporting a wife who left teaching to be home full time with their two-year-old son. This episode is a masterclass in calculated action, intentional sequencing, and building a real estate portfolio the right way when you don't have a wealthy family or a safety net to fall back on.
What You'll Learn in This Episode
Timeline Highlights
[0:00] – Introducing Tony Moreno and his background in engineering and real estate
[3:35] – Growing up in the Dominican Republic: Christian roots, his grandfather's legacy, and what poverty looked like up close
[6:45] – Why Tony's father moved the family to America — and why he says to this day he doesn't fully know why, but doesn't regret it
[7:48] – His father's immigration experience: re-validating an engineering degree from scratch over three years
[8:55] – Cleveland to Dominican Republic to Huntsville: the full immigration timeline
[9:51] – How his dad Googled "best places to live in America" in 2009 and chose Huntsville based on the number one result
[13:52] – First career out of college: automotive manufacturing, 60-70 hour weeks, and the moment that broke him
[15:37] – The confrontation with his plant manager that made him realize he needed to build something of his own
[16:51] – Moving jobs and realizing no job was going to solve the real problem — purpose and control
[18:35] – The mindset shift toward real estate: a mix of wanting freedom and searching for purpose
[20:06] – Rich Dad Poor Dad during Thanksgiving 2019 — the book that opened the door
[21:06] – How Tony reads books: as an engineer, he takes notes, flags formulas, and goes back and forth until he fully understands
[22:06] – Training camp: analyzing 300 properties at ten a day before ever making an offer
[25:27] – Setting a weekly offer goal of three per week — right in the middle of Covid uncertainty
[27:29] – Two offers accepted at the same time in August 2020 — and the panic that followed
[29:07] – How he funded the deals: collateral loan on a paid-off Honda Civic and a 401K withdrawal
[33:36] – The worst case scenario exercise: if tenants stop paying, can I still make the mortgage? Yes. Pull the trigger.
[39:04] – 2021 market frenzy: offers going nowhere, pivoting to courthouse steps, then discovering subject-to
[41:33] – How Tony approached subject-to ethically: presenting sellers all options before stepping in
[44:29] – Current portfolio snapshot: 25-plus units, mobile home parks, and a 24-unit apartment under underwriting
[44:50] – Why he dropped his hard W-2 exit date — and the airport conversation with Alicia Merryman that reframed his thinking
[45:31] – His wife's decision to leave teaching to stay home — and why he called it the best thing they could do
[51:31] – Rapid fire questions begin
[51:58] – Favorite life quote: "Your life is not about you" — Maximilian Kolbe
[53:07] – The dangerous early belief: that this was a solo game and connections didn't matter
[54:13] – What he gave up to win: social time with friends he loved but who weren't aligned with his goals
[55:25] – What he would not do again: go at it alone from day one
[57:37] – The failure that still influences him: letting feelings drive a deal — the third flip where he lost money and cost his father money too
[59:11] – His wife, his son, and why being present matters as much as building the portfolio
Rapid Fire Highlights
Resources Mentioned
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Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.
In this episode, host Jason Seward sits down with Brandon Lindsey — Richmond-based real estate investor, licensed contractor, and creator of The Rehab Playbook — for a ground-level master class on new construction investing. Brandon has spent years mastering both sides of the business: the construction process and the real estate strategy behind it. That dual fluency is rare, and this conversation makes full use of it.
Brandon walks through the entire new construction process from start to finish — deal evaluation, due diligence, permitting, site preparation, phased construction, listing strategy, financing, and cash flow management — drawing direct comparisons to fix and flip rehabs throughout so experienced flippers can see exactly where they already have transferable skills and where the learning curve sharpens. His core philosophy is that a builder's most important job is not swinging a hammer, but playing air traffic controller — coordinating subs, inspectors, vendors, and timelines simultaneously while keeping the project moving and profitable.
Brandon also opens up about the business side that trips most people up: building to the market instead of your own taste, knowing when to bring in an interior designer and stay out of the way, understanding plan B exit strategies before you break ground, and protecting cash flow above everything else. He built his coaching community, The Rehab Playbook, and its inner circle, The New Build Group, around exactly these lessons — helping investors get into new construction with systems, checklists, and a network behind them rather than learning through expensive mistakes alone.
What You'll Learn in This Episode
Timeline Highlights
[0:00] – Introducing Brandon Lindsey and his background in construction and real estate investing
[2:59] – Brandon's first Dealmaker event in 2020: hiding in the back, faking phone calls, and running to the bathroom to avoid conversation
[5:01] – How Brandon evolved from that introvert who couldn't shake hands to running his own group and speaking on the main stage
[7:00] – Why networking transformed his business — and what introversion actually means versus what people think it means
[8:27] – Setting up the new construction master class and who this conversation is built for
[9:43] – Step 1: Evaluating the deal — how new construction underwriting compares to rehabs
[11:21] – Optimizing square footage to maximize return before you ever break ground
[12:42] – Step 2: Due diligence — site prep, zoning ordinances, setbacks, special use permits, and variances
[16:57] – Why knowing your municipality's appetite — and the people in it — is the most important thing a new builder can do
[20:55] – Why checklists are non-negotiable across every phase of new construction
[23:10] – Step 3: Planning and permitting — what's in your permit package and why contractors need a business license in every municipality
[25:51] – The contractor question: what non-licensed investors need to account for in their underwriting
[26:43] – Brandon's cost per square foot benchmarks — and why economies of scale matter more than most people realize
[29:25] – Breaking ground: site preparation checklist, construction entrance, silt fence, permit box, and clearing
[30:31] – Phase 1: Footings, foundation, framing, and drying in — and how this maps to a full gut renovation
[32:07] – The air traffic controller concept: why heavy communication, not hammers, is the real job
[34:15] – How to schedule subs 3 to 4 weeks out to minimize gaps and keep timelines tight
[37:01] – Phase 2: Roughing — plumbing, HVAC, electrical, roofing, framing inspection, insulation
[38:15] – Phase 3: Interior veneer — drywall, trim, doors, floors, tile. By the end, no framing members visible
[39:25] – When to start working with your realtor — before the build is done or even listed
[41:10] – Why Brandon runs every 50/50 decision through his realtor and lets them lead on finishes
[44:23] – Why he hires an interior designer and steps back — so he can focus on air traffic control
[48:49] – What to do when the house doesn't sell: plan B exit strategies and why price point matters more than construction type
[52:15] – Financing options: banks, hard money, private money, JV structures, and lines of credit
[53:41] – Why cash flow kills more new construction businesses than bad deals do
[56:02] – The importance of liquidity and building a full tool belt of financing options before you need them
[59:01] – How to get involved with The Rehab Playbook and The New Build Group
Rapid Fire Highlights
Resources Mentioned
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Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.
In this episode, host Jason Seward sits down with Michael Zuber — author, investor, and founder of One Rental at a Time — for one of the most tactically dense conversations the show has produced. Michael started investing in 2002 while working a demanding full-time tech career, buying his first rental in Fresno, California and building his portfolio one property at a time over the next two decades. He survived the 2008 crash, scaled past 100 units, and reached financial independence in his mid-forties before walking away from his W-2 entirely.
What makes this episode different is the framework. Michael doesn't deal in theory or motivation — he shows up with seven specific rules he has refined over nearly 30 years in the game, and he walks through each one with clarity and conviction. From establishing a buy box and committing to 20 minutes of daily discipline, to writing 100 disrespectful offers and auditing the people and content you consume — every rule is actionable and immediately applicable.
Michael also pulls no punches on what holds most investors back: chasing the wrong goals, diluting their focus across too many markets and asset types, and refusing to do the boring repetitive work that actually builds wealth. The conversation goes deep on offer volume, pipeline thinking, the danger of C-class properties, and why real estate is a 5-to-10 year commitment — not a get-rich-quick play. For anyone stuck, spinning their wheels, or just getting started, this episode is required listening.
What You'll Learn in This Episode
Timeline Highlights
[0:00] – Introducing Michael Zuber and his One Rental at a Time origin story
[2:22] – How Greg Dickerson connected Jason to both Jim Ingersoll and Michael Zuber seven years ago
[3:57] – Jim Ingersoll gave Michael his first speaking opportunity — why he will never forget it
[4:55] – The networking rule Michael missed for the first five years: meet two new people a week
[7:37] – Rule 1: Establish a buy box — what it is and why it changes everything
[10:57] – Why having multiple buy boxes means you have lost
[11:43] – Rule 2: Daily discipline — 20 minutes a day, seven days a week, no exceptions
[14:33] – Rule 3: Grow your network — two new people a week compounds into a thousand in a decade
[18:04] – Rule 4: Learn average first — you can't write great offers until you know what average looks like
[19:32] – Rule 5: Bad things will happen — learn and move on, but never repeat the same mistake
[21:57] – Celebrating a $1.2M loss so the whole team learned from it
[23:57] – Rule 6: This is a 5-to-10 year commitment — why 2020-21 created more failures than fortunes
[25:21] – Rule 7: Audit your network — fire the poison, including the content you consume daily
[28:37] – Why most investors fail before they start: writing too few offers and fearing rejection
[29:46] – The wrong goal: "I want to buy a deal this year" — and what the right goal actually is
[32:16] – How Michael did 56 flips in 27 months by writing disrespectful offers relentlessly
[34:10] – Why real estate agents should stop avoiding investor clients
[38:05] – Rapid fire questions begin
[38:28] – Charlie Munger's three L's that destroy wealth: ladies, liquor, and leverage
[39:34] – The dangerous early belief: thinking he was smarter than everyone and could do it alone
[41:49] – What he gave up to win: balance, weekends, and family time — and his honest reflection on it
[44:23] – What he would not do again: buying C-class properties
[45:38] – How a Bruce Norris event in 2007 led Michael to sell everything and 1031 into apartments before the crash
[46:58] – The failure that still shapes him: his relentless work ethic is both his superpower and his Achilles heel
[48:16] – Why he started his YouTube channel and what has always been his North Star
Rapid Fire Highlights
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Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.
In this episode of Dealmaker Catalyst, host Jason Seward sits down with Wendy Coles — real estate investor, agent, private lender, and one of the most compelling voices in the Dealmaker community — for a deep dive into the strategies and mindset shifts that transformed her investing journey.
Wendy's story is not a straight line. She entered real estate at 47 with no resume, no retirement, and no roadmap — just a closed gym business and a determination to build something lasting. For her first two years, she operated in isolation, figuring things out alone and leaving enormous opportunity on the table simply because she didn't know what she didn't know. It wasn't until she walked through the doors of her first Dealmaker event — nervous, hoping no one would notice her — that the trajectory began to shift.
This episode focuses on the tactical and emotional progression that follows that first uncomfortable step: learning to network as an introvert, discovering creative financing and DSCRs, leaning into private lending, and finding a sense of purpose through humanitarian work with Share the Love. Wendy also opens up about the failure that knocked her off course — two emotionally driven property purchases that deviated from her system and set her back — and what it taught her about discipline and staying in your lane. Raw, relatable, and packed with practical takeaways, this is exactly the kind of episode that makes someone decide to finally walk through the door.
What You'll Learn in This Episode
Timeline Highlights
[0:00] – Introducing Wendy Coles and what makes her story so widely resonant
[4:08] – Operating solo for two years and not knowing what she was missing
[5:38] – Why Wendy entered real estate at 47 with no resume and no retirement plan
[7:05] – Walking into her first Dealmaker event hoping nobody would notice her
[8:13] – Imposter syndrome, negative self-talk, and feeling like she didn't belong
[10:07] – The conversation with Jim Ingersoll that made her feel like she wasn't alone
[13:28] – The icebreaker question that makes networking easier for introverts
[15:09] – What the Dealmaker community revealed about creative financing and DSCRs
[17:06] – Sitting next to Leon Johnson without knowing who he was — and what that taught her
[19:00] – How Share the Love entered her life at a pivotal personal moment
[20:38] – Nine humanitarian trips and the real estate education that came with them
[23:28] – From back of the room in 2022 to front of the stage — the full circle moment
[24:18] – What she's speaking on at the Dealmaker event: obstacles to opportunities
[28:45] – Rapid fire questions begin
[29:26] – Her favorite life quote: "You are the director of your life"
[30:16] – The belief that kept her stuck: that success required a path she had already missed
[32:22] – What she had to give up to start recognizing her own wins
[34:27] – What she would not do again: intentionally going slow when the deals were there
[36:21] – The failure that knocked her back: two emotional property purchases outside her system
[39:23] – What the next five years look like: lending, creative finance, and buying outside the country
Rapid Fire Highlights
Resources Mentioned
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If this episode sparked something for you, subscribe, leave a review, and share it with someone who's serious about building their real estate legacy. New episodes every week.
Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.
In this special launch episode, host Jason Seward sits down with Jim Ingersoll — founder of the Dealmaker community and widely known as "The Godfather of Richmond Real Estate" — to introduce the Dealmaker Catalyst podcast and lay out the vision driving it forward. Recorded on the heels of a major three-day Dealmaker event, the intent is clear: this show exists to change trajectories.
Jason and Jim reflect on how a single podcast episode can plant a seed that grows into a full real estate career — Jason shares how a BiggerPockets episode introduced him to the BRRRR strategy and rewired the direction of his investing life. The Dealmaker Catalyst is built to be more than motivational. It's designed as a field-level education, pulling in experts from every corner of real estate to break down the mechanics of what they do and how they got there. Whether you're brand new or a seasoned investor looking to expand into a new niche, this show will meet you where you are.
Jim also opens up about his own origin story: leaving corporate America as an engineer, the early failures that forced him to build real systems, and the culture of authentic connection he has spent two decades cultivating through the Dealmaker brand. This episode sets the tone for everything that follows — tactical, real, and built for action takers.
What You'll Learn in This Episode
Timeline Highlights
[0:00] – Introducing the Dealmaker Catalyst and host Jason Seward
[1:05] – The energy and vision behind launching the podcast
[4:14] – How a BiggerPockets episode changed Jason's investing trajectory
[6:16] – The range of strategies and asset classes the show will cover
[9:52] – Jim's engineering background and guests who succeeded without a diploma
[11:29] – Expanding Dealmaker chapters nationwide
[11:55] – Introverts in real estate: Jim identifies as a recovered introvert
[13:48] – Why introverts are naturally gifted networkers
[15:09] – The icebreaker question Jim learned from Leon Johnson
[16:14] – How authentic transparency builds real connections
[18:20] – Jim's first Tampa event 20 years ago — nervous, unknown, and about to change everything
[21:56] – Rapid fire questions begin
[23:21] – What he had to give up mentally when leaving the 9-to-5 world
[25:30] – What Jim would not do again: selling properties he wishes he still owned
[26:30] – First failure: the Jamestown duplex and the systems it forced him to build
Rapid Fire Highlights
Resources Mentioned
Connect and Subscribe
If this episode sparked something for you, subscribe, leave a review, and share it with someone who's serious about building their real estate legacy. New episodes every week.
Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.
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