The DealMachine Real Estate Investing Podcast

BRRRR investing can be a game-changer—unless you get it wrong. In this episode, David shares the biggest mistakes he made with the BRRRR method and what he’d do differently. From contractor pitfalls to financing nightmares, learn from his hard-earned lessons so you don’t make the same costly errors.   KEY TALKING POINTS: 0:00 - Guest Breaks Down His Current Situation 0:36 - The Pitfalls David Expe...

Flipping houses the traditional way can be a grind—but what if there’s a smarter, lower-risk approach that saves time and effort? In this 15-minute highlight from our latest DealMachine Masterclass, Casey Gregersen breaks down his strategy for flipping houses with less hassle, more efficiency, and a fresh perspective on making deals work in today’s market.   KEY TALKING POINTS: 0:00 - A New Strate...

David breaks down the four biggest reasons you're struggling to land your first deal—and how to overcome them. He answers real questions from Khang Le's students, sharing hard-earned insights on rental strategies, deal analysis, and the mindset shifts that make all the difference. If you've been stuck on the sidelines, this one's for you.   KEY TALKING POINTS: 0:00 - Introduction 0:19 - How Do You...

David didn’t set out to build a real estate software company—he just needed a tool to help him find more deals. That tool turned into DealMachine. In this episode, he sits down with Dustin Heiner to share his journey from real estate investor to tech founder, the lessons he learned along the way, and the surprising ways his mindset had to shift to make it all work.   KEY TALKING POINTS: 0:00 - Bei...

Most investors leave thousands on the table every year—because they don’t know these tax loopholes. In this episode, David sits down with real estate tax strategist Ana Klein to break down 8 tax strategies the wealthy use to keep more cash in their pockets. From cost segregation to the Augusta Rule, learn how to legally lower your tax bill and maximize your real estate profits. If you're in real e...

When it comes to selling your wholesale deals, do you want more money or less work? James Quigg from New Western breaks down the three main dispo methods—handling it yourself for max profit, using online marketplaces for quick exposure, or fully automating the process to scale fast. Each has its pros and cons, and picking the right one can make all the difference. Tune in to learn which dispo stra...

In this episode, David sits down with Vikram Deol and Cody May from Sheridan Street to uncover the harsh realities that cause most agents to fail and quit. From ineffective sales processes to poor messaging and a lack of strategic follow-up, they reveal the mistakes holding agents back and share actionable strategies to overcome them. If you’re tired of spinning your wheels and ready to level up,...

If you’ve ever dreamed of quitting your job and living off rental income, this episode is for you. David sits down with Dustin Heiner, an investor who replaced his 9-to-5 income with rental properties and became “successfully unemployed.” From out-of-state investing to the debate between cheap and expensive rentals, Dustin shares his strategies for building wealth and escaping the rat race. Discov...

After getting laid off, Micah Johnson turned a setback into a $12,000 payday on his first wholesale deal. In this episode, he shares how he made it happen fast with Ryan’s guidance and the mindset shift that set him up for success. Whether you’re facing challenges or just starting out, Micah’s journey proves that the right support and strategy can change everything.   KEY TALKING POINTS: 0:00 - In...

In this 15-minute masterclass highlight, Liz Faircloth shares three powerful lessons that turned a vacant commercial building into a six-figure success story. Learn how mastering your market, doing competitive due diligence, and strategically repositioning a property can transform even the toughest real estate challenges into profitable opportunities.   Liz Faircloth's Free Market Analysis Tool: h...

Think ugly, cheap houses aren’t worth your time? Think again. In this episode, Stephanie Lombardo shares her secrets to finding rundown properties, adding value, and flipping them for big profits. She explains why mid-level flips are perfect for beginners and how to avoid costly mistakes. You’ll also learn her strategies for working with contractors, deciding between flips and rentals, and balanci...

They bought land for $237K in 2021. Now, it’s worth $32 million just 4 years later. In this episode, Seth and Tori Bolt reveal how they built a $32M short-term rental empire with Bolt Farm Treehouse, boasting 2,500+ 5-star reviews, a $700 average daily rate, and 93% occupancy — all while staying 100% off Airbnb. Turn Your Short Term Rental into a 7 figure business (workshop): https://www.boltfarmt...

Most investors either give up too soon or waste money going too long without results. In this episode, Nicholas Nick joins David and Ryan to break down the numbers—how much marketing does it really take to land a deal? Whether you're cold calling or sending mail, knowing the right benchmarks can save you time and money.   KEY TALKING POINTS: 0:00 - Introduction 0:53 - An Overview of Nicholas Nick’...

Talking to sellers can make or break your real estate deals. In this 15-minute masterclass recap, Jiries Dawaher walks through the entire seller conversation—from the first call to the final offer. Learn how to ask the right questions, present comps effectively, and handle objections like a pro. If you’re struggling to turn leads into contracts, this is the episode you need.   KEY TALKING POINTS:...

Flipping land in the U.S. while living in Ireland? That’s exactly what Ciaran Sheil does, and in this episode, he breaks down his process. David and Ryan dive into how he finds deals, handles negotiations, and closes transactions—all without ever stepping foot in the States. If you’ve ever wondered how to invest remotely, this episode is for you.   KEY TALKING POINTS: 0:00 - Introduction 1:43 - Ho...

Allen Prather is flipping 100 homes this year and building a 100-unit rental portfolio—all while transitioning from car dealerships to real estate investing. In this episode, he shares how he’s scaling his business, the challenges of high-volume flipping, and why wholesaling is next on his list. If you’re serious about growing your real estate business, don’t miss this one.   KEY TALKING POINTS: 0...

Most investors don’t realize they’re using government lists the wrong way—or missing out on better data entirely. In this video, David breaks down the biggest mistakes real estate investors make when pulling and marketing to government lists. Learn how to unlock high-quality leads, avoid wasting money, and tap into hidden data sources that can give you an edge.   Get the 1000 code enforcement city...

Most first-time wholesalers make a few thousand on their first deal—but Dennis Freeman walked away with $50K in just one week. In this episode, Dennis breaks down exactly how he found the deal, how he locked it up under pressure, and why he transitioned from wholesaling to the BRRRR strategy. If you're looking for real-world insights on making big moves in real estate, this is one to tune in for....

Half of all real estate deals never make it to closing—so what’s stopping them? In this 15-minute masterclass highlight, David Olds reveals the hidden pitfalls that kill deals and the simple systems top investors use to keep contracts from falling apart. If you’re tired of losing deals at the last minute, this is your fix.   KEY TALKING POINTS: 0:00 - How Many Deals Are You Losing? 1:37 - The Obst...

Carlos Lujan, an 18-year-old entrepreneur, is already flipping sneakers and watches—but now he’s got his sights set on real estate. In this episode, David breaks down the similarities between reselling and wholesaling, shares key steps to getting started, and gives Carlos a game plan to land his first deal. If you’re looking for practical, no-BS advice on real estate investing, this one’s for you....

Costa Karellas made $120K on his first flip in Boston—but instead of doubling down, he pivoted to wholesaling remotely in Kansas City. In this episode, he reveals why he made the switch, the power of partnerships, and the Marine Corps mindset that drives his success. Plus, David shares insights on balancing investing while running DealMachine.   KEY TALKING POINTS: 0:00 - Introduction 0:10 - What...

How do you consistently close 50+ real estate deals a year without burning out? Chad Klamen shares his journey from mentorship and early struggles to building a business that operates at high volume. He reveals the hiring strategies that made the biggest difference, his approach to balancing wholesaling, flipping, and rentals, and why his focus now is on scaling smarter, not just bigger.   KEY TAL...

What would you do if you lost everything? David Choi has closed over 1,000 real estate deals, but in this 15-minute highlight, he lays out the 7 steps he’d take if he had to start over from scratch. With limited resources and no network, this is the exact blueprint he’d follow to rebuild a million-dollar business—and you can follow it too.   KEY TALKING POINTS: 0:00 - What David Choi Would Do If H...

Codie Chesner flips 50 houses a year—and he’s not slowing down. He breaks down how he finds deals, raises private money through social media, and keeps contractors in check. Plus, he shares the biggest lessons from scaling his business and why he’s shifting gears in 2025.   KEY TALKING POINTS: 0:00 - An Overview Of Codie Chesner’s Business 0:57 - What Drew Codie To Fix & Flips 2:22 - The Average T...

Most wholesalers are leaving deals (and cash) on the table—Zach Cook isn’t. He breaks down how he converts more leads, builds seller relationships, and monetizes deals others walk away from. From cold calling to creative deal structuring, Zach shares the strategies that keep his pipeline full and his profits growing. If you’re in the game, you need to hear this.   KEY TALKING POINTS: 0:00 - An Ove...