Doug Bennett is the founder of DB Wealth Planning and Preservation, a bestselling author, and host of the globally ranked Goals DO Come True podcast, who has spent over 30 years helping business owners find the date when work becomes optional. His own path included two divorces, a motorcycle accident at 95 miles an hour, and near bankruptcy, all of which now shape how he coaches clients through the psychological side of money.

In this episode, Doug joins Chris to talk about the power of writing down specific, income based goals, why the shift from saving to spending is mostly mental, and the lesson he learned watching his father delay retirement until it was too late. Chris also connects Doug's story back to the 3 Paydays® System and why creative real estate deals beat the traditional one time payday.

[1:07] Chris introduces Doug Bennett, founder of DB Wealth Planning and Preservation and host of the Goals DO Come True podcast.

[3:12] Doug shares that both his parents died within 12 weeks of each other, and that his dad never got to enjoy the retirement he'd delayed.

[4:12] Doug explains his mission: helping business owners find the date when work becomes optional and giving themselves permission to spend.

[5:03] Doug says the shift from saving to spending is mostly psychological, shaped by his own two divorces, a serious motorcycle accident, and near bankruptcy.

[6:38] Doug introduces his book, Think Simple Win Big, written from the lessons of selling a chunk of his business for just over a million pounds.

[10:27] Chris pivots to the 3 Paydays System, explaining why creative real estate deals beat the old way of getting paid once.

[13:45] Doug traces his goal setting practice back to 2004, when he rediscovered a goals notebook and found he'd hit 10 of 11 goals he'd written down years earlier.

[15:28] Doug describes doubling his income goal repeatedly, from $100K to $200K to $250K, raising the bar each time he got close.

[16:21] Doug's actual income landed at $250,268 against a $250,000 goal, the moment that convinced him to double the target again.

[16:50] Doug shares that a firm bought a stake in his business for $500,000 in 2019 and another $500,000 plus in 2020.

[17:11] Doug warns that money disappears quickly without a plan, and that his own divorce ended up costing him half of what he'd built.

[17:54] Chris and Doug discuss self imposed limits on goals, and Doug's advice to start with small, believable goals before ramping up.

[21:21] Doug and Chris agree that finding a mentor or community cuts years off the learning curve compared to figuring it out alone.

[22:54] Doug reframes the goal from "retirement" to reaching the point where every choice is open to you.

[24:05] Doug shares where listeners can find his book, his podcast, and his free guide through Smart Real Estate Coach.

1. Write your goals down, even the ones that feel unreasonable. Doug rediscovered a goals notebook years later and had hit 10 of 11 goals he'd written down, several of which he'd completely forgotten setting.
2. The shift from saving to spending is a psychological one, not a math problem. Doug spends most of his time giving clients permission to actually use the money they've worked to build.
3. Don't wait for "someday" to enjoy what you've built. Doug's father delayed retirement to be with his dying wife and passed away shortly after her, having never gotten the time he was waiting for.
4. Start with small, believable goals before you chase the big ones. If you've never hit a goal before, you won't trust bigger ones until you've proven smaller ones to yourself first.
5. Money without a plan disappears fast. Doug's own experience selling part of his business for over a million dollars, then losing much of it to an unplanned lifestyle and a divorce, is a reminder that earning it is only half the job.

Book Your Free Discovery Call https://SmartRealEstateCoachPodcast.com/Discovery

Download: Inside the Deals (Real Case Studies) https://SmartRealEstateCoachPodcast.com/Deals

Explore Our Partner Resources https://SmartRealEstateCoachPodcast.com/Resources Doug's Free Guide (From Financial Struggle to Financial Success) https://smartrealestatecoach.com/doug Goals DO Come True Podcast https://podcasts.apple.com/us/podcast/goals-do-come-true-with-doug-bennett/id1530802197

This week marks our third Wednesday, which means it's time for a conversation with someone from our own community, and I couldn't be more excited to have Derek Dombeck back. Derek's been coaching with us for about a year now at the highest levels of our program, and he brings almost 25 years of his own real estate investing experience to every session. Today I wanted to get his honest, unfiltered perspective on what actually separates the students who take off fast from the ones who stay stuck, since he's seen it up close in a way nobody else has.

Derek gets real about what he's learned coaching inside our community: why showing up to live events and building genuine relationships accelerates everyone's progress, why he's passionate about a communication and negotiation system he built called No Means Not Yet, and why option-based deals on distressed and default properties remain one of the most overlooked tools in creative real estate. He also opens up about a genuinely hard season this year and the way our community showed up for him. If you've ever wondered what's actually happening behind the scenes at the highest levels of a coaching community, this conversation pulls back the curtain.

Key Talking Points of the Episode

00:40 Announcing the show's new format: a solo cast every first Wednesday, a community guest every third Wednesday

01:17 Introducing Derek Dombeck and his coaching role at the Presidents Club and High 6 levels

02:24 The number one difference between students who take off fast and those who stay stuck: showing up and building relationships

04:08 What Deal Lab and Deal Room actually look like, and why nothing like it exists elsewhere in the industry

06:32 What's changed in Derek's own beliefs about the industry after coaching at this level

08:29 Why creative deals beat the old way of getting paid once, no matter the market

10:15 Why some leads people assume are dead can still produce five or six figures once properly structured

11:39 Introducing Derek's No Means Not Yet system and its four steps

12:54 Introducing the Apprentice Program as a low commitment way to meet the team in person

13:23 The recurring "aha" Derek sees: people opening up about personal challenges affecting their business

16:12 Introducing the weekly Monday Rant and why the people who engage with it consistently succeed

19:09 Derek shares the loss of his mother in June and the support he received from the community

20:27 What's encouraging Derek most about creative real estate right now: options on distressed properties

22:24 Derek's message to 10,000 listeners on why now is the time to learn creative real estate

24:12 Closing thoughts and how to schedule a free advisory call

Quotables

"It's not what we do every day, all day, but just knowing that the resource is there and the ability to do those deals are there."

"Is there a better time to do creative? And the answer is every day."

"There is no better time to get started. I don't care when you're listening to this, today is the day to get started."

Links

No Means Not Yet: https://smartrealestatecoach.com/nomeansnotyet

Propsperity: https://propsperity.io

The Generations of Wealth: https://thegenerationsofwealth.com

Book Your Free Discovery Call: https://SmartRealEstateCoachPodcast.com/Discovery

Download: Inside the Deals (Real Case Studies): https://SmartRealEstateCoachPodcast.com/Deals

Watch the Free Masterclass: https://SmartRealEstateCoachPodcast.com/Mastersclass

Learn About the Apprentice Program: https://3PaydaysApprentice.com/Podcast

Explore Our Partner Resources: https://SmartRealEstateCoachPodcast.com/Resources

In this solo episode, I want to hit on something that I think is the single biggest thing separating you from your next deal, and it's not another strategy or skill set. It's clarity. I just got back from our Deal Lab, and for the third time in a row, I watched the exact same lightbulb go off in people's heads: it was never the deal structure holding them back, it was not knowing, with total clarity, what their own path actually looked like.

I use an analogy that's stuck with me for years: imagine buying a thousand-piece puzzle, dumping all the pieces on the table, throwing away the box lid that shows you the picture, and then wondering three days later why you haven't finished it. That's exactly how most investors approach this business, trying to piece together random strategies without ever seeing the full picture first. I walk through my own version of that chaos, the four years after the 2008 crash where I dabbled with pieces instead of committing to one clear system, until necessity forced me into creative finance because I genuinely had no other option.

I also break down the real order of how this works: clarity comes first, then action, then confidence, never the other way around. Readiness is never going to show up on its own while you wait for it. Finally, I talk about our September 3 Paydays Live event, going back to our roots this year with no outside speakers, and how I'm making it easier than ever to attend with a fully refundable seat fee.

If you've been stuck in the "when I'm ready" mindset, waiting for one more course or one more sign before you actually start, this episode is a direct challenge to that thinking.

Key Talking Points of the Episode

00:23 Introducing today's topic: why clarity, not skill, is what separates you from your next deal

01:28 What just happened at Deal Lab and the lightbulb moment investors keep having

02:47 The thousand piece puzzle analogy for how most investors approach this business

03:47 Chris's own story: four years of dabbling with pieces after the 2008 crash

05:15 Why creative finance became his only option, and why it's a better path in general

06:06 The free discovery session offer with the Smart Real Estate Coach team

07:53 The pattern Chris hears constantly at Deal Lab: "I'll start when..."

08:46 Why readiness never comes first, and the real order: clarity, then action, then confidence

09:18 Why every deal affects three or four lives, not just the investor's own

10:27 What makes Three Paydays Live different from typical industry events: no outside speakers

11:38 Announcing the refundable seat fee for September's Three Paydays Live event

13:24 Announcing 3 Paydays Live for September 27th through 29th

14:07 What attendees will see: real deals, real numbers, and the full three paydays model

14:34 New this year: hands-on workshops and extended Q&A after each session

Quotables

"Readiness doesn't come first. It's clarity, then action, then confidence."

"It's not a predatory niche in creative. It's a win win win niche."

"It's costing you tens of thousands, if not hundreds of thousands of dollars by not taking action."

Links

3 Paydays® Live

https://3paydayslive.com/podcast

Free Discovery Call

https://smartrealestatecoachpodcast.com/discovery

3 Paydays® System Mastery Course - Use coupon code for 50% off

https://smartrealestatecoach.com/qls

Coupon code: pod

Apprentice Program

http://3paydaysapprentice.com/Podcast

Masterclass

https://smartrealestatecoach.com/masterspodcast

3 Paydays Books

https://3paydaysbooks.com/podcast

Partners

https://smartrealestatecoach.com/podcastresources

I've been digging into mobile home park investing for some personal initiatives lately, so this was a genuinely selfish interview for me. My guest, Brad Johnson, is the co-founder and CIO of Vintage Capital, and he's got the kind of resume that makes you want to just sit back and ask questions: 20 years across traditional and alternative asset classes, over $3.3 billion in commercial real estate acquisitions closed, and a rare perspective as both a former mobile home park operator and a current capital allocator in the space.

We started with his own jump from Wall Street, leaving a real estate investment bank in his mid-30s, right after having his first kid, because manufactured housing showed the highest cash flow yields paired with the lowest default rates he'd ever seen, a combination that shouldn't exist but does. From there we got tactical: what makes mobile home parks structurally different from other real estate, why owning the infrastructure instead of the homes themselves changes your entire profit margin, and the specific due diligence checklist Brad runs on every deal, from market-level home price ratios down to road and utility conditions.

We also got into the money side that most people never hear about: seller financing on smaller parks, how mom-and-pop sellers with decades of depreciation often want creative structuring more than a cash-out, and the accelerated depreciation tax benefit tied to land improvements that can hand investors an outsized first-year tax loss. Brad closed with a stat that stuck with me: the major players in this space have never had a negative year of net operating income growth in 25 years, a steady 5% annual compound that's almost unheard of in a normally cyclical asset class.

If you've ever driven past a mobile home community and wondered whether there was real money in it, or you're already investing creatively and want to know how this niche fits into a three paydays approach, this conversation is worth your full attention.

Key Talking Points of the Episode

00:44 Introducing Brad Johnson, co-founder and CIO of Vintage Capital

01:04 Brad's 20 years across traditional and alternative asset classes, and $3.3 billion in acquisitions

02:05 Why Brad chose real estate over Wall Street securities: insider knowledge and lower volatility

03:15 Discovering manufactured housing's unusual combination of high yield and low default rates

03:33 Leaving a W-2 in his mid-30s, right after his first child, to buy mobile home parks

05:19 Advice for high income earners stuck and afraid to leave their W-2

07:23 Why mobile home parks structurally have low default rates and declining supply

08:35 Why owning the infrastructure instead of the homes creates higher profit margins

09:42 Park sizes Vintage Capital focuses on: the 50 to 150 pad middle market

11:53 Key due diligence: market-level home prices, population stability, and infrastructure condition

16:20 The accelerated depreciation tax benefit tied to land improvements and infrastructure

17:33 Why Vintage Capital partners with local operators and avoids anti-landlord states

19:34 How seller financing shows up in mobile home park deals, and why

22:08 A real community story: a woman who focused on free-and-clear parks for creative financing

23:12 Why clustering smaller parks into a regional portfolio creates arbitrage opportunities

24:32 How to reach Brad and Vintage Capital directly

25:37 The stat that stands out: 25 years without a single negative year of NOI growth

Quotables

"If I don't do it now, I'm never going to do it."

"You can and should operate with the utmost confidence… it doesn't matter if you're in an up, down, or sideways market."

"The major players in our space have never had a negative year of NOI growth… a steady compound at 5% per year."

Links

Vintage Capital — Brad's mobile home park investment firm and educational resources — https://vintage-funds.com

3 Paydays® Live

https://3paydayslive.com/podcast

Free Discovery Call

https://smartrealestatecoachpodcast.com/discovery

3 Paydays® System Mastery Course - Use coupon code for 50% off

https://smartrealestatecoach.com/qls

Coupon code: pod

Apprentice Program

http://3paydaysapprentice.com/Podcast

Masterclass

https://smartrealestatecoach.com/masterspodcast

3 Paydays Books

https://3paydaysbooks.com/podcast

Partners

https://smartrealestatecoach.com/podcastresources

In this solo episode, I wanted to make a couple of important announcements and get real about why most real estate investors never actually do a deal. Starting now, we're pivoting the Smart Real Estate Coach podcast to twice a month: the first Wednesday will be a solo cast from me, and the third Wednesday will feature someone from our Smart Real Estate Coach family sharing their own success story, many of whom started with zero experience.

I get honest about my own story here too, including hitting a real low point between 2008 and 2012, going from an oceanfront home to a one-bedroom apartment in my mid-40s, starting over completely. What changed things wasn't the market, it was me finally admitting I was the problem, which also meant I was the solution. I break down why most investors don't fail from lack of knowledge, they fail because they never actually get in the game with a real, structured plan.

I also announce the rebrand of what used to be our In The Trenches Bootcamp, now called Deal Lab, a hands-on, in-person experience where you're calling real leads, structuring real offers on a whiteboard, and walking away with real metrics and a plan, not just concepts. I walk through the five step formula I use with every student: get honest about where you are, decide where you want to go, identify what's really blocking you, build a massive action plan with help, and track it relentlessly.

Finally, I announce this year's 3 Paydays Live event, September 27th through 29th, which is going back to our roots this year with no outside speakers, just our family team and coaches who are doing deals in the trenches every single week. If you've been stuck studying instead of doing, or waiting for permission you're never going to get, this episode is the direct nudge to finally get in the game.

Key Talking Points of the Episode

00:23 Introducing new announcements and updates to the show

02:13 The podcast's new format: twice monthly, solo casts and family member success stories

03:16 Why now is the biggest opportunity Chris has seen in 35 years in the business

04:13 The real reason most investors fail: never getting in the game with a real plan

05:08 Why staying in one niche for 3 to 7 years matters more than chasing shiny objects

06:06 Introducing what used to be In The Trenches Bootcamp, now rebranded as Deal Lab

07:03 Chris's own rock bottom: a one bedroom apartment in his mid-40s after an oceanfront home

09:16 Why "drifting" without deciding is the most expensive thing an investor can do

09:38 The four year stretch, 2008 to 2012, that cost Chris millions in missed opportunity

10:00 A real member example: designing a one year, one million dollar three paydays plan

12:09 The advice from a past podcast guest: "just get in a different room"

13:36 How Deal Lab actually works across its two and three quarter days

15:13 The five step formula: honesty, direction, identifying blocks, action, and tracking

16:11 A member's real 90 day metrics, and why numbers turn a hobby into a business

18:07 Announcing 3 Paydays Live, September 27 to 29, with no outside speakers this year

19:24 What's new at this year's event: hands on workshops and extended Q&A

Quotables

"If you're stuck, the good news is guess what, you're also the solution."

"If you don't have numbers, you have a hobby. You don't have a business."

"There's not a lack of deals right now. There's just a lack of knowledge on how to structure the right deals."

Links

3 Paydays® Live

https://3paydayslive.com/podcast

Free Discovery Call

https://smartrealestatecoachpodcast.com/discovery

3 Paydays® System Mastery Course - Use coupon code for 50% off

https://smartrealestatecoach.com/qls

Coupon code: pod

Apprentice Program

http://3paydaysapprentice.com/Podcast

Masterclass

https://smartrealestatecoach.com/masterspodcast

3 Paydays Books

https://3paydaysbooks.com/podcast

Partners

https://smartrealestatecoach.com/podcastresources

Six years is a long time between visits, and I was excited to catch up with Seth Greene, someone I've known and worked with going all the way back to 2017 or 2018. Seth is the founder and CEO of Market Domination, one of the nation's foremost authorities on growing a business through strategic affiliate and referral relationships, and under his leadership Market Domination landed a spot on the Inc. 5000 list of fastest growing companies. He's also the co-host of the Sharkpreneur podcast alongside Kevin Harrington, the original Shark from Shark Tank, a nine-time bestselling author, and has been featured on NBC News, CBS News, Forbes, Inc., and CBS MoneyWatch.

We got into what Market Domination is doing right now, which has changed a lot even in just the last six years. Seth walked me through two of their newest capabilities: a way to place your podcast ads on other people's podcasts to grow your own audience, and a way to pull real time Google search data to build a list of people actively searching things like "sell my house" or "rent to own" in your target city, so you can put your message directly in front of a warm audience.

We also got into the biggest marketing mistake Seth sees investors make, which is simply blending in and looking like everyone else, and who his services are actually built for, established investors doing real volume, not someone on their very first deal. Seth shared his process for building a network of "dream partners," people who already have your ideal audience, and how his own book turns podcast guest appearances into a referral engine.

Toward the end, Seth got personal and told me the single most important thing he's learned recently: who you're being affects how well what you do actually works. It's less about the newest marketing tactic and more about the internal work. If you want a masterclass in both cutting edge direct response marketing and the mindset underneath it, this episode has both.

Key Talking Points of the Episode

00:23 Welcoming Seth Greene back after six years and revisiting his background

02:22 Catching up on what Seth has been building since his last appearance

02:48 The two newest capabilities at Market Domination: podcast-to-podcast advertising and Google search data targeting

04:23 Who the Google search targeting tool is actually built for

05:31 The biggest marketing mistake Seth sees real estate investors make

06:41 Who Seth's services are and are not a good fit for

07:36 Using accredited investor data to help investors raise capital without their own money

08:34 Overcoming the fear of pitching investors by getting reps in and expecting rejection

09:17 Why creative deals and the three paydays model beat the old way of getting paid once

11:39 Whether budget minimums apply the same way to brand new investors

12:40 Seth's pricing tiers, from self-serve resources to a full outsourced marketing department

13:22 How to reach Seth for an exploratory call

14:00 Confirming how long Seth and Chris have worked together

14:39 Other ways to reach Seth: email, website, and LinkedIn

14:57 Where Seth sees AI heading in marketing, and why the human check still matters

16:14 What's changed in AI-assisted marketing just in the last couple of hours of testing

16:31 The three things Seth would prioritize first if he stepped into real estate marketing tomorrow

18:19 Building a network of dream JV partners who already have your ideal audience

19:29 A preview of Chris's upcoming appearance on the Sharkpreneur podcast

19:47 The most important thing Seth has learned recently: who you're being affects how well what you do works

21:17 The $4 Sandwich, the book Seth recommends for mindset work

22:14 Closing thoughts and where to find Seth going forward

Quotables

"Who you're being affects how well what you do works."

"If you say the same things as everybody else, nobody knows how to tell you apart."

"Go have some really bad offer conversations… get some reps under your belt with getting rejected so you improve your technique."

Links

Market Domination LLC (Seth's direct response marketing firm) — https://www.marketdominationllc.com

Sharkpreneur Podcast (Seth's podcast with Kevin Harrington of Shark Tank) — https://sharkpreneurpodcast.com

The Ultimate Guide to Growing Your Business with a Podcast: Turning Warm Fuzzy Feelings Into Cold Hard Cash (Seth's book, 30% off Amazon price for listeners as stated on air) — https://www.amazon.com/Ultimate-Guide-Growing-Business-Podcast/dp/B096LTQBH6

Book a call with Seth (free exploratory call for members of the Smart Real Estate Coach community) — https://bookwithseth.com

3 Paydays® Live

https://3paydayslive.com/podcast

Free Discovery Call

https://smartrealestatecoachpodcast.com/discovery

3 Paydays® System Mastery Course - Use coupon code for 50% off

https://smartrealestatecoach.com/qls

Coupon code: pod

Apprentice Program

http://3paydaysapprentice.com/Podcast

Masterclass

https://smartrealestatecoach.com/masterspodcast

3 Paydays Books

https://3paydaysbooks.com/podcast

Partners

https://smartrealestatecoach.com/podcastresources

In this episode, I sit down with Chris Larsen, founder of Next-Level Income and someone with over 20 years and nearly three decades in real estate. What I love about Chris's story is where it started: he bought his first rental property at age 21, while he was still a college student at Virginia Tech studying biomechanical engineering. From there he has been involved in around $2 billion in acquisitions across development, private lending, distressed debt, commercial offices, and multifamily syndication.

Before real estate, Chris was chasing a very different dream. He was a competitive cyclist with hopes of going pro, until the sudden loss of his best friend at a bike race forced him to ask what he was really doing it all for. That moment set him on a search for financial freedom, and after five years of reading everything he could get his hands on, he landed on real estate as his path. He walks us through the mindset shift from day trading and stress to building something with control, leverage, income, and long term certainty.

We get practical about why now is a great time for W-2 earners to move off the sidelines. Chris shares the story of his very first deal, $3,000 down on a townhouse that he house hacked with two roommates, and how a 1031 exchange years later turned that tiny investment into a seven figure return. He is a big believer that real estate is a get rich slow game, and he makes the case for doing even one creative deal a year and letting time, rents, and inflation do the heavy lifting.

We also dig into where we are in the real estate cycle. Chris breaks down the roughly 18.5 year cycle, why he thinks we are in the second half where it pays to be the bank, and why keeping some dry powder on the sidelines makes sense right now. Toward the end he shares the two free tools his team built, an interactive book and a Chris Larsen AI coaching assistant, for anyone who wants to go deeper. If you have been waiting for a sign to start building passive income, this conversation is it.

Key Talking Points of the Episode

00:00 Introduction and the three paydays philosophy

00:23 Meet Chris Larsen: 20+ years and roughly $2 billion in acquisitions

00:52 Buying his first rental at 21 as a college student

02:32 Why he wrote his latest book to help people engineer freedom

03:04 Starting a nonprofit after Hurricane Helene hit Asheville

03:52 The cyclist dream and why pro cycling rarely pays

04:51 Losing his best friend at a bike race and the emptiness that followed

06:35 The discipline and structure cycling taught him

06:51 Deciding he wanted to live life on his own terms

07:48 From day trading stress to realizing that is not investing

08:46 Why real estate: control, leverage, income, and depreciation

09:37 The 15 year plan to reach ten grand a month in income

09:52 Why creative deals beat the old way of getting paid once

12:05 What Chris is working on now and his latest book

12:48 Moving from residential to commercial and multifamily

14:13 Why now is a great time for W-2 earners to get in

15:20 Real estate as a get rich slow game and the one deal a year approach

16:02 The $3,000 first deal that became a seven figure return through a 1031

17:55 The 18.5 year real estate cycle explained

20:09 Why it is a good time to be the bank

20:31 Keeping cash on the sidelines and staying selective

21:43 The two free tools: the interactive book and Chris Larsen AI

22:42 How high income earners can start investing passively

23:20 Why finding someone who made the mistake first shortens your curve

Quotables

"Real estate is a get rich slow game."

"During the second half of the cycle, it's a great time to be the bank."

"You don't have to time the market, but be very selective right now."

Links

Chris Larsen — Next Level Income (his education and investment company) — https://nextlevelincome.com

Free Book, How to Be Financially Free by Forty (interactive, includes online course access) — https://nextlevelincome.com/financialfreedombook

Chris Larsen AI (24/7 coaching assistant built from Chris's books, content, and podcasts, via Next Level Income) — https://nextlevelincome.com

3 Paydays® Live

https://3paydayslive.com/podcast

Free Discovery Call

https://smartrealestatecoachpodcast.com/discovery

3 Paydays® System Mastery Course - Use coupon code for 50% off

https://smartrealestatecoach.com/qls

Coupon code: pod

Apprentice Program

http://3paydaysapprentice.com/Podcast

Masterclass

https://smartrealestatecoach.com/masterspodcast

3 Paydays Books

https://3paydaysbooks.com/podcast

Partners

https://smartrealestatecoach.com/podcastresources

In this episode, I sit down with Sam Primm, a St. Louis investor, entrepreneur, and best-selling author of Own Your Freedom. Sam made a serious jump from a W-2 corporate job into real estate, and he did not play small. Over the last 12 years he has closed more than 2,000 deals and built a rental portfolio worth around $50 million, all without using his own money.

What I appreciated most about this conversation is how candid Sam was. He walked me through the early days of buying one rental at a time on the side, the moment he realized he could keep scaling with other people's money, and the systemized way he finally left his job rather than jumping in blind. We also got real about the last couple of years, where higher interest rates and a tougher market forced him to lean into personal development and grind through a genuine mental test.

We spent a good chunk of time on mentorship and mindset, because that is where Sam and I are cut from the same cloth. He makes the case for why even the best in the world hire coaches, why poor people look at the cost of something while wealthy people look at the return, and why the fear of failure quietly guarantees that people never succeed. He is also refreshingly blunt about the guru problem in this space and what separates people actually doing deals from those just selling courses.

Toward the end, Sam shares what he is focused on now: repositioning a portfolio that got a little too heavy in multifamily during the 2021 and 2022 run-up, and re-honing in on simple single family rentals, which he believes are the best starting point for 90% of newer investors. If you have been on the fence about getting a coach, scared of debt, or afraid to fail, this one will light a fire under you.

Key Talking Points of the Episode

00:00 Introduction and the three paydays philosophy

00:22 Meet Sam Primm: 2,000+ deals and a $50 million portfolio using none of his own money

01:51 Sam's path from an engineer's son to full-time investor

02:07 Reading Rich Dad Poor Dad and starting to invest on the side

04:12 The original goal of one rental a year for ten years

04:46 Seeing the power of scaling with other people's money and leaving the job

05:33 Whether Sam leaned on mentors and coaches early on

06:10 Merging with a local investor who taught him to build a real company

07:09 The mental game of going from solo operator to running a company

07:48 Why the last two or three years have been a mental grind

09:41 Why mentorship still matters at every stage

10:14 The Tom Brady example: the best in the world still hire coaches

10:55 Poor people look at cost, wealthy people look at return

11:46 A look inside the Apprentice program and In the Trenches Bootcamp

14:44 Context and perspective: a $10,000 dinner versus a $10,000 wealth tool

16:08 Sam's take on gurus who have never done a deal

17:08 Why coaches who stop doing deals lose touch with the market

18:47 What Sam is focused on today and repositioning the portfolio

19:38 The Branson hotel lesson and roughly $20,000 a month in losses

20:13 Why single family rentals are his calling card

22:24 Two closing nuggets: don't fear debt and expect failure

24:08 Why the first deal going sideways is the best thing that can happen

Quotables

"Nobody creates wealth with their own money, or they're already wealthy."

"Poor people look at the cost of something. Wealthy people look at the return."

"People avoid failure, and unknowingly they're avoiding success."

Links:

Sam Primm — Faster Freedom (his real estate education company) — Faster Freedom

Sam Primm on Instagram — @samfasterfreedom — https://www.instagram.com/samfasterfreedom/

Sam Primm on YouTube — https://www.youtube.com/c/SamFasterFreedom

3 Paydays® Live

https://3paydayslive.com/podcast

Free Discovery Call

https://smartrealestatecoachpodcast.com/discovery

3 Paydays® System Mastery Course - Use coupon code for 50% off

https://smartrealestatecoach.com/qls

Coupon code: pod

Apprentice Program

http://3paydaysapprentice.com/Podcast

Masterclass

https://smartrealestatecoach.com/masterspodcast

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Partners

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Keith Gillispie deployed overseas 13 times as an active duty Marine. His kids didn't know who he was. That was the moment he decided real estate would be his path to financial freedom and time with his family. Now he runs two companies, coaches high-income W-2 earners and military investors, and has helped hundreds of investors build businesses that run on systems instead of chaos.

In this episode, Chris sits down with Keith, founder of REI Automated, to talk about what it actually takes to build a real estate business when you are strapped for time. Keith works primarily with active duty military, first responders, executives, and other high-demand professionals who are making good money but have no time to spare. His answer to that problem is automation, and his platform has systematized more than 90% of the repetitive, time-consuming tasks that keep most investors stuck in the weeds.

Keith also breaks down the three ingredients every investor needs to succeed: the right education, the right systems, and the right support. He explains why most people in the so-called coaching space are not actually coaches, how to vet who you learn from, and why asking for help is the one thing most former military investors resist the longest.

One of his clients, an active duty naval officer carrying a full course load, closed his tenth deal in under a year. The excuse is not the issue. The system is.

Key Takeaways

1. Every business that has stood the test of time runs on systems. Once you build the right systems, you can automate the majority of your workflow and let a computer do the repetitive work so you can focus on what actually drives revenue.

2. There are three ingredients you need to succeed in real estate: the right education, the right systems, and the right support. You can have the first two and still burn out or quit without someone in your corner who has been through it.

3. Busy work that does not drive revenue will kill your business. Rule number one is keep revenue in first position. If what you are doing right now is not moving a deal forward, stop and get on the phone with sellers.

4. Most people in the education space are not coaches. Before you invest in someone's program, find out if they are actively doing deals, not just talking about them. Real coaching comes from people who are still in the trenches.

5. Success leaves clues, but you have to meet people where they are. If someone is in chapter 15 of their journey and you are in chapter one, do not copy what they are doing now. Ask them what they did at the beginning.

Key Talking Points of the Episode

00:00 Introduction

00:18 Who is Keith Gillispie?

01:50 Keith Gillispie's Background: From Active Duty Marine to Real Estate

04:41 Helping High-Income W-2 Earners and First Responders

05:36 The Importance of Systems and Automation in Business

06:58 Managing Business Through Virtual Assistants and Checklists

08:35 Learning Creative Financing and Other Strategies Beyond Wholesaling

09:23 Busy Work Vs. Revenue-Driving Actions

10:14 The Three Ingredients for Success: Education, Systems, and Support

11:54 The Advantages of Creative Deals and the 3 Paydays System

14:25 Navigating the Challenges of Growing 2 Companies Simultaneously

16:17 Education, Information and Qualified Coaching

18:11 Free Courses and Resources for Investors

20:18 The Importance of Finding a Mentor

Links

3 Paydays® Live

https://3paydayslive.com/podcast

Free Discovery Call

https://smartrealestatecoachpodcast.com/discovery

3 Paydays® System Mastery Course - Use coupon code for 50% off

https://smartrealestatecoach.com/qls

Coupon code: pod

Apprentice Program

http://3paydaysapprentice.com/Podcast

Masterclass

https://smartrealestatecoach.com/masterspodcast

3 Paydays Books

https://3paydaysbooks.com/podcast

Partners

https://smartrealestatecoach.com/podcastresources

Most people who haven't done their first creative real estate deal don't have an ability problem. They have a clarity problem. There is a big difference between the two, and it is the reason so many investors stay stuck collecting strategies, watching videos, and taking courses without ever actually closing a deal.

In this solo episode, Chris breaks down exactly why clarity is the missing piece for most people considering creative real estate, and why the 3 Paydays™ Live event exists. After the 2008 crash wiped him out after nearly two decades in the business, Chris realized that even experience doesn't give you clarity on its own. What changed everything was proximity: getting in the room, watching real conversations happen in real time, and seeing how deals actually come together from lead to structure to close.

That is the environment 3 Paydays™ Live is built to create. No outside speakers selling from the stage. No fluff panels. No theory-heavy presentations. Just Chris and the Smart Real Estate Coach family team, with over 104 years of combined experience and billions of dollars in transactions, walking you through the complete sequence: how the lead comes in, what the discovery conversation looks like, how to structure a deal that works for both parties, and how the 3 Paydays™ model generates between $45,000 and $350,000 per deal.

3 Paydays™ Live runs September 27 through 29 in Warwick, Rhode Island. Tickets are available now for a $97 refundable deposit when you show up.

Key Takeaways

1. The barrier to your first creative real estate deal is not ability or readiness, it is clarity. Once you see the full process clearly, the action follows naturally.

2. Collecting strategies, scripts, and courses in pieces is like doing a puzzle without the box. Deals happen in a specific logical sequence, and you need to see the whole picture to execute confidently.

3. Proximity accelerates everything. Watching real conversations and real deal structures happen in real time compresses years of learning into months, just as it did for Chris after the 2008 crash.

4. The 3 Paydays™ model replaces the transactional treadmill of one-time paydays with three separate income streams from a single deal, generating between $45,000 and $350,000 per deal across the community.

5. You do not become ready by waiting. Readiness comes from exposure, association, and seeing how deals actually work, not from studying more content alone.

Key Talking Points of the Episode

00:00 Introduction

00:35 The importance of clarity in creative real estate

01:51 How the 3 Paydays™ System is different from traditional real estate

03:21 The value of proximity and real-time exposure

04:10 Why what you're focusing on is crucial to your success

05:08 The real reason most investors stay stuck

06:58 Structuring win-win deals for sellers

07:22 What is a 3 Payday deal?

08:27 Typical earnings from 3 Payday deals

08:52 3 Paydays™ Live 2026: Warwick, Rhode Island

09:33 Learning from experienced coaches

10:14 The Process: Lead intake, discovery, and the quadrant method

13:13 The 1 year $1 million+ model

15:23 Real-life success stories from event attendees

18:14 Event details: 3 Paydays™ Live 2026

Links

3 Paydays® Live

https://3paydayslive.com/podcast

Free Discovery Call

https://smartrealestatecoachpodcast.com/discovery

3 Paydays® System Mastery Course - Use coupon code for 50% off

https://smartrealestatecoach.com/qls

Coupon code: pod

Apprentice Program

http://3paydaysapprentice.com/Podcast

Masterclass

https://smartrealestatecoach.com/masterspodcast

3 Paydays Books

https://3paydaysbooks.com/podcast

Partners

https://smartrealestatecoach.com/podcastresources