The DealMachine Real Estate Investing Podcast

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. KEY TALKING POINTS:0:00 - Introduction0:27 - How Dennis Freeman Got His Start In Real Estate3:11 - The Dispo Process For His First Wholesale Deal5:16 - Turning His Garage Into An ADU8:28 - The Difference In Midwestern Markets Vs West Coast10:17 - Dennis’ Advice For New Investors LINKS:Facebook: Dennis Freemanhttps://www.facebook.com/dennis.freeman.54390 Instagram: David Leckohttps://www.instagram.com/dlecko Website: DealMachinehttps://www.dealmachine.com/pod Instagram: Ryan Haywoodhttps://www.instagram.com/heritage_home_investments Website: Heritage Home Investmentshttps://www.heritagehomeinvestments.com/

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 Obstacles And Distractions Investors Face2:33 - Introducing ezREIclosings4:14 - Doing The Math On Lost Deals7:12 - Why Are These Deals So Hard To Close?11:18 - What ezREIclosings Has Done For Investors12:26 - Gaining The Edge In A Crowded Market14:21 - Outro LINKS:Instagram: David Oldshttps://www.instagram.com/davidoldsrei/ Website: David Oldshttps://linktr.ee/davidoldsrei/ Instagram: David Leckohttps://www.instagram.com/dlecko Website: DealMachinehttps://www.dealmachine.com/pod Instagram: Ryan Haywoodhttps://www.instagram.com/heritage_home_investments Website: Heritage Home Investmentshttps://www.heritagehomeinvestments.com/

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. KEY TALKING POINTS:0:00 - Why Does Carlos Want To Get Into Entrepreneurship?1:41 - How Flipping A House Compares To Reselling Shoes4:18 - How To Take The Next Step Towards Real Estate7:56 - Discipline Creates Success10:40 - Outro LINKS:Instagram: David Leckohttps://www.instagram.com/dlecko Website: DealMachinehttps://www.dealmachine.com/pod Instagram: Ryan Haywoodhttps://www.instagram.com/heritage_home_investments Website: Heritage Home Investmentshttps://www.heritagehomeinvestments.com/

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 - Introduction0:10 - What Costa Karellas Learned From Being A Marine Corps Captain5:16 - His Goal When He Started His Business7:47 - The Power Of Leveraging Partnerships11:20 - Getting The Reps12:19 - How Long Costa Has Been In His Market13:32 - Learning Skills Before You Hire Someone Else17:34 - Moving Slow To Move Fast20:34 - David Speaks On Investing Alongside Running DealMachine22:44 - Costa’s Business Partners And Personality Profiles He Looks For26:31 - His Worst Day As A Real Estate Investor31:33 - Why He Decided To Switch To Wholesaling34:03 - Outro LINKS:Instagram: Costa Karellashttps://www.instagram.com/costa_karellas/ Website: Costa Karellashttps://www.kl-propertygroup.com/ Instagram: David Leckohttps://www.instagram.com/dlecko Website: DealMachinehttps://www.dealmachine.com/pod Instagram: Ryan Haywoodhttps://www.instagram.com/heritage_home_investments Website: Heritage Home Investmentshttps://www.heritagehomeinvestments.com/

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 TALKING POINTS:0:00 - Introduction0:31 - An Overview of Chad Klamen’s Business3:44 - Learning Through Mentorship From The Richest People In St. Louis12:15 - Finally Getting Hired By His Dad16:00 - Is Wholesaling Affected By Interest Rates?18:58 - What’s Driving Chad To Grow His Business23:22 - What He’s Learned From Being In CG27:04 - Hiring Executive Assistants And Good Hiring Practices33:59 - Outro LINKS:Instagram: Chad Klamenhttps://www.instagram.com/insta___chad/ Website: Chad Klamenhttps://www.klamengroup.com/ Instagram: David Leckohttps://www.instagram.com/dlecko Website: DealMachinehttps://www.dealmachine.com/pod Instagram: Ryan Haywoodhttps://www.instagram.com/heritage_home_investments Website: Heritage Home Investmentshttps://www.heritagehomeinvestments.com/

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 He Went Bankrupt Today1:05 - Step 1: Create An Entity, Then Get Your CRM And Dialer In Place6:39 - Step 2: Getting Your Marketing Set Up8:07 - Step 3: See Where You Need To Improve Based On KPIs11:06 - Step 4: Going Deep On Your Data12:04 - Step 5: Building Out Your Direct Mail Approach13:24 - Step 6: Lead Management13:48 - Step 7: Leadership14:57 - Outro LINKS:Instagram: David Choihttps://www.instagram.com/davidchoi.biz/ Website: David Choihttps://www.dealsanddollarsacademy.com/ Instagram: David Leckohttps://www.instagram.com/dlecko Website: DealMachinehttps://www.dealmachine.com/pod Instagram: Ryan Haywoodhttps://www.instagram.com/heritage_home_investments Website: Heritage Home Investmentshttps://www.heritagehomeinvestments.com/

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 Business0:57 - What Drew Codie To Fix & Flips2:22 - The Average Time & Profit For Their Flips5:50 - When Codie Did His First Deal7:52 - His Second Deal10:03 - How He Raises Money From Social Media12:14 - Working With Lenders15:13 - His Biggest Challenge Of Getting To 50 Flips Per Year17:08 - Preventing Contractors From Taking Money19:09 - Where He Wants To Take His Business In 202521:33 - Gain Knowledge And Skills First, Then Hire24:24 - Outro LINKS:Instagram: Codie Chesnerhttps://www.instagram.com/codie.chesner/ Website: Codie Chesnerhttps://www.chesnerinv.com/ Instagram: David Leckohttps://www.instagram.com/dlecko Website: DealMachinehttps://www.dealmachine.com/pod Instagram: Ryan Haywoodhttps://www.instagram.com/heritage_home_investments Website: Heritage Home Investmentshttps://www.heritagehomeinvestments.com/

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 Overview of Zach Cook’s Business1:21 - The Marketing Strategies They Use In Their Business4:49 - What Is A Novation?5:49 - How Zach Measures His Success8:39 - How To Tell If Someone Is Actually Serious About Selling10:27 - The Hardest Part Of Zach’s Role12:05 - Their Employee Structure & Getting Licensed As An Agent15:45 - What’s New For Them In 202517:54 - How He Got Started In Real Estate20:02 - Advice For Aspiring Investors21:45 - Outro LINKS:Instagram: Zach Cookhttps://www.instagram.com/zcookrealestate706/ Website: Zach Cookhttps://www.myershousebuyers.com/ Instagram: David Leckohttps://www.instagram.com/dlecko Website: DealMachinehttps://www.dealmachine.com/pod Instagram: Ryan Haywoodhttps://www.instagram.com/heritage_home_investments Website: Heritage Home Investmentshttps://www.heritagehomeinvestments.com/

David sits down with Paul Myers to explore how he turned Myers House Buyers into a $1 million-a-year real estate business. From leveraging postcards, cold calling, and SEO to building strong relationships with agents, Paul reveals the systems and strategies that fueled his success. KEY TALKING POINTS:0:00 - Paul Myers’ Business3:25 - When He Decided To Go Into Real Estate Full Time5:19 - His First Hire In His Business8:44 - Their First Deal12:07 - Finding Buyers At A Local Auction15:49 - How Him And His Wife Felt After His First Deal16:54 - His First Employee’s First Deal19:31 - What Percentage Is A Standard Wholesale Deal?21:55 - Wholesaling And The Changing Real Estate Market22:47 - Where He Wants To Take His Business In 202527:46 - The Power Of Driving For Dollars34:45 - Outro LINKS:Instagram: Paul Myershttps://www.instagram.com/therealpaulmyers/ Website: Paul Myershttps://www.myershousebuyers.com/ Instagram: David Leckohttps://www.instagram.com/dlecko Website: DealMachinehttps://www.dealmachine.com/pod Instagram: Ryan Haywoodhttps://www.instagram.com/heritage_home_investments Website: Heritage Home Investmentshttps://www.heritagehomeinvestments.com/

Discover the five steps to raising private money in 2025 with insights from Jay Conner. This 15-minute highlight from the DealMachine Masterclass breaks down everything you need to know, including where to find private lenders, crafting effective scripts, and securing stress-free funding. Perfect for investors ready to level up their funding game. KEY TALKING POINTS:0:00 - What Is A Private Lender?1:55 - When To Use Private Money2:48 - Why Would A Lender Be Interested?4:57 - Step 1: Identify Prospects5:55 - Step 2: Opening Conversation Script11:05 - Step 3: Stress-Free Investing Audio11:44 - Step 4: One-On-One Appointment12:45 - Step 5: Verbal Pledge13:24 - What To Concentrate On First & Know Your Program14:28 - The Documents You’ll Need15:00 - Outro LINKS:Instagram: Jay Connerhttps://www.instagram.com/privatemoneyauthority/ Website: Jay Connerhttps://www.jayconner.com/ Instagram: David Leckohttps://www.instagram.com/dlecko Website: DealMachinehttps://www.dealmachine.com/pod Instagram: Ryan Haywoodhttps://www.instagram.com/heritage_home_investments Website: Heritage Home Investmentshttps://www.heritagehomeinvestments.com/