The DealMachine Real Estate Investing Podcast

Are you finding that solely focusing on wholesale assignments limits your ability to capture long-term wealth and leaves you reliant on constantly finding new buyers? In this episode, we speak with Casey Gregersen, who started with his first off-market deal in 2010 and has built a vertically integrated real estate business. Casey will share how he evolved beyond just wholesaling, incorporating in-house construction and property management for his rental portfolio, aiming to complete 100 deals this year across various strategies. Learn how you can expand beyond the constraints of strictly wholesaling by understanding the benefits of buy-and-hold, fix and flip, and even raising capital to build a more resilient and profitable business.Here are three more impressive things about Casey Gregersen:Casey's real estate journey began with house hacking his first off-market deal in 2010, immediately generating cash flow by renting out rooms.Despite starting in real estate early, Casey continued to work a full-time W2 job at Shell for several years, strategically using his income and time off to learn and invest further.Casey made a significant life decision to leave his full-time job at Shell after realizing he was missing important family moments, demonstrating his commitment to aligning his work and personal priorities after building a stable real estate business. KEY TALKING POINTS:0:00 - An Overview Of Casey Gregersen’s Business1:39 - When Casey Did His First Off-Market Deal3:49 - His Next Deals After That7:04 - The Mindset That Allowed Him To Rent Out His First Property9:20 - What Casey Would Say To People Who Think Interest Rates Are Too High13:12 - Is It Too Late To Invest In Real Estate?14:55 - Casey’s Lowest Lows In Business17:25 - His High Points In Business21:06 - What He’d Be Doing If He Never Got Into Real Estate22:20 - What He’s Looking Forward To Most In 202523:25 - The Data That Casey Needs The Most28:18 - The Last Topic He Spoke About At Collective Genius That Made Him Proud29:26 - The Mindset That Led To Casey’s Success31:36 - Tax Cheat Codes & The Entrepreneur Mindset39:02 - Outro LINKS:Instagram: Casey Gregersenhttps://www.instagram.com/caseygregersen Website: Casey Gregersenhttps://caseygregersen.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 real estate calls aren’t random—they follow patterns. In this episode, Erick Gydesen breaks down the 9 most common types of seller calls, from the angry "Remove me!" to the motivated "I liked your offer." You’ll learn exactly how to handle each one, keep the conversation alive, and turn more calls into closings. KEY TALKING POINTS:0:00 - The Nine Different Types Of Seller Calls0:33 - 1: The Removal Call3:15 - 2: The Confusion Call4:16 - 3: I’m Saving It For Later4:45 - 4: On Market Home That Isn’t Selling8:35 - 5: Your Offer Is Too Low10:10 - 6: The Influencer Call11:19 - 7: I’m Selling, But Not For A Few Months12:30 - 8: I’m Trying To Learn More About Your Process14:35 - 9: I Like Your Offer15:14 - Outro LINKS:Instagram: Erick Gydesenhttps://www.instagram.com/ErickGydesen/ Website: DM Forcehttps://dmforce.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/

Are you frustrated by the limited opportunities in traditional real estate and the struggle to find unique, high-potential deals? In this episode, we speak with Bentley Pugh from Seattle, who transitioned from being a real estate agent to specializing in underutilized infill lots and development opportunities. He'll share his journey and insights into how he identifies these unique situations in a competitive market like Seattle, and how his business achieved rapid growth to $12 million after just four to five years. Learn how Bentley's unconventional approach to real estate can provide a fresh perspective on finding less competitive and potentially lucrative deals Here are three more impressive things about Bentley Pugh:Bentley Pugh got into the real estate business simply by being a real estate agent. This suggests a grounded and organic entry into the field that later led to his specialization.His business focuses on underutilized infill lots. This specialization indicates a strategic approach to finding opportunities within a developed area like Seattle, potentially leveraging existing infrastructure.Bentley has a unique approach to finding talent, as evidenced by him observing someone doing good work (like diligently signing ballots) and then hiring that person months later. This demonstrates a keen eye for potential and a longer-term recruitment strategy. KEY TALKING POINTS:0:00 - An Overview of Bentley Pugh’s Business2:50 - How His Life Would Be Different If He Wasn’t Investing3:25 - What Helped Him Become Successful In Business8:34 - Experiencing Tough Times In Business13:16 - The Highest Highs In His Business14:12 - How Do You Find Infill Lots?16:16 - What Bentley Would Say To Someone Who Says Interest Rates Are Too High18:04 - His Mindset On Teaching His Kids About Money19:54 - What He’s Looking Forward To In 202520:45 - Helping Your Employees Grow23:48 - Where He Finds Most Of His Team Members26:27 - Bentley’s Takeaway From Their Day At CG27:24 - What He Would Say To Someone Who Says It’s Too Late To Start27:48 - Closing Thoughts28:07 - Outro LINKS:Instagram: Beachworks LLChttps://www.instagram.com/beachworksllc/ Website: Beachworks LLChttps://beachworks.org/ 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/

Are you overwhelmed by the challenges of scaling your wholesaling operation and building a reliable team? In this episode, we dive into the journey of Corey Reyment, who started in 2016 and has since completed 800 to 1,000 wholesale deals. Corey will share his insights on overcoming hiring pitfalls and developing effective marketing strategies, revealing how he built a business that now closes a significant volume of deals and averages around $23,000 per wholesale transaction. Learn actionable steps to streamline your growth and avoid costly mistakes from someone who has achieved substantial success in the wholesaling industry. Here are three more impressive things about Corey Reyment that weren't mentioned in the intro:Corey quickly transitioned into wholesaling, completing his first wholesale deal just four days after purchasing his first rental property in 2016. This demonstrates his rapid entry and early success in the wholesaling business.His motivation for starting his business was driven by a desire to escape an unfulfilling job and gain more time with his family. This personal drive and clear "intensity" fueled his entrepreneurial journey.Corey's company has a significant marketing budget, spending approximately $50,000 to $60,000 per month, which equates to about 15% of their total revenue. This substantial investment highlights their commitment to consistent lead generation. KEY TALKING POINTS:0:00 - An Overview of Corey Reyment’s Business1:19 - Why He Likes Wholesaling Better Than Flipping & His First Deal3:13 - What He Makes Now On An Average Wholesale Deal5:37 - Corey’s Approach To Marketing8:46 - What He Was Trying To Accomplish When He Started His Business10:38 - The Mindset That Allowed Him To Grow His Business & His Hiring Process15:41 - The Lowest Lows And The Highest Highs He’s Had In His Business19:26 - The Transformation Of DealMachine20:56 - Is It Too Late To Invest In Real Estate?23:49 - The Data That Corey Would Love But Can’t Find26:11 - What Corey’s Looking Forward To Most In 202529:21 - How He Found His First Wholesale Deal So Quickly30:16 - How Corey Would Tell Dave Ramsay That Debt Is Good35:36 - Outro LINKS:Instagram: Corey Reymenthttps://www.instagram.com/foxcities_homebuyers/ Website: Corey Reymenthttps://www.foxcitieshomebuyers.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/

Are you struggling to find profitable wholesale deals in an increasingly competitive market? In this episode, we speak with CJ Moss, who, operating in the tight Rhode Island and Massachusetts markets, is currently closing six deals per week. He'll reveal how his company carved out a niche, focusing on properties four units and under, allowing them to achieve an average profit of $60,000 per deal. Learn how CJ and his team bypass intense competition and consistently generate impressive results, offering a roadmap to transform your wholesaling business. Here are three of the most impressive things from the conversation with CJ Moss:CJ's wholesaling business in a competitive New England market is achieving significant scale, closing around six deals per week and aiming for 300 deals this year. This high volume demonstrates their strong operational capabilities and market penetration.They are generating an exceptional average profit of $60,000 per wholesale deal. This impressive margin highlights their ability to find highly profitable opportunities in their chosen niche of properties with four units or less.CJ and his wife have successfully built a "pretty big team" focused entirely on wholesaling "straight assignments" after starting in 2019. They have also identified clear roles, with CJ as the visionary and his wife as a "sales killer," contributing to their rapid growth and success. KEY TALKING POINTS:0:00 - An Overview of CJ Moss’s Business1:09 - What He Was Trying To Accomplish When He Started His Business1:55 - When He First Started Doing Multi-Family4:21 - His Goal With Building More Passive Income5:55 - Why He Chose To Focus On 4 Units And Less & How He Finds Deals8:01 - How His Marketing Approach Evolved9:04 - How He Found Out About Wholesaling11:44 - What To Say When Someone Says “Can I Pick Your Brain?”16:51 - How David Figured Out His Hiring Process21:42 - David’s View On Improving Performance Of His Employees25:20 - What DealMachine Does To Stay In Front Of The Competition28:10 - What CJ’s Looking Forward To In 202531:54 - The Predictive Index & Other Performance Personality Tests35:11 - David’s Thoughts On Bringing In A Different CEO36:34 - Experiencing Burnout When Running A Business40:20 - Closing Thoughts41:09 - Rapid Fire Questions For CJ44:01 - Outro LINKS:Instagram: CJ Mosshttps://www.instagram.com/MossHomeSolutions/ Website: CJ Mosshttps://www.mosshomesolutions.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/

You don’t need to go fast, spend big, or build a massive team to succeed in real estate. In this 15-minute masterclass highlight, Coach Carson shares how he's built wealth through a focused, steady approach—using simple systems, smart networking, and consistent follow-up. Whether you’re aiming for your first deal or your fifth, this is the blueprint for finding deals without burning out. KEY TALKING POINTS:0:00 - Investor Types Divided Into Tortoise Vs Cheetah1:23 - DealFinding 101: The Fundamentals3:52 - Utilizing Professional DealFinders8:19 - DealFinding 201: Seller Outreach11:33 - DealFinding 301: Advanced Methods15:06 - Outro LINKS:Instagram: Coach Carsonhttps://www.instagram.com/CoachChadCarson/ Website: Coach Carsonhttps://www.coachcarson.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/

Are you tired of the constant struggle to find reliable end buyers for your wholesale deals? In this episode, we speak with Kurt Byers from New Western, a company with 35 offices nationwide that acts as a marketplace connecting wholesalers with over 200,000 pre-qualified investors. Kurt will explain how New Western works with thousands of wholesalers every year and closes close to 800 to 1,000 deals a month, effectively automating your disposition process. Learn how you can tap into their extensive network and simplify your business, moving away from the time-consuming task of buyer hunting. KEY TALKING POINTS:0:00 - An Overview of Kurt Byers’ Business1:51 - Has The Industry Continued To Grow?4:15 - How New Western Works With Wholesalers5:29 - The Best Way To Present Deals To New Western9:29 - Pitfalls When Analyzing A Deal10:35 - How The Greater Real Estate Market Affects Off-Market Deal Investors13:01 - What People Don’t Know About New Western14:20 - Their Role In The Deals They Do17:24 - Where They Find Their Agents18:55 - Strongman Competitions20:16 - How He Found Himself In A Leadership Role At New Western21:20 - The Multi-Market Approach They Help With23:07 - Mindsets That Have Helped Him With Business27:01 - What Strongman Competitions Taught Him About Real Estate29:02 - Outro LINKS:Instagram: New Westernhttps://www.instagram.com/NewWestern/ Website: New Westernhttps://www.newwestern.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/

Tired of the same old wholesaling grind? Today, we have Karl Spielvogel, who uncovers hidden real estate opportunities by tackling the complex problems others avoid. Karl specializes in properties with tangled title issues, judgments, and other unique challenges. He'll share his secrets for turning these complicated situations into lucrative deals with less competition, offering a fresh perspective for ambitious wholesalers.Karl made $249,000 on one deal after finding out two of the owners were deceased. He left a note and a FedEx package explaining the situation to the living owner, and after nine months, she contacted him, leading to the deal. In this deal he bought three properties — one was bought for $57,000 and sold for $125,000! KEY TALKING POINTS:0:00 - An Overview Of Karl Spielvogel’s Business0:45 - Why He Specializes In Harder Deals That Turn Other Investors Away3:00 - What Is A “Variance”?3:57 - Title Issues He Had With A Complex Deal5:07 - The Mindset That’s Allowed Him To Focus On The Harder Problems6:01 - What He Was Trying To Accomplish When He Started His Business8:11 - How He Got His Creativity In Business Deals9:56 - What He Learned Recently12:56 - Using Long Term Investment Strategies & His Exit Strategy15:43 - The Ins And Outs Of Purchasing A Judgment22:08 - What Karl’s Looking Forward To In 202523:15 - How To Get In Touch With Karl And His Deal Criteria24:40 - Outro LINKS:Contact Karl: 704-995-5385Instagram: Karl Spielvogelhttps://www.instagram.com/karlspielvogel/ Website: Karl Spielvogelhttps://www.legacylinkproperties.com/consultants 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 gets on the phone with a seller who isn’t desperate, knows what the property’s worth, and wants $100k for it. In this live call, you’ll hear how David builds trust, asks the right questions, and navigates the conversation toward a creative offer—without playing the lowball game. Plus, he breaks down the deal live on the spot, from ARV to repair costs to contract strategy. KEY TALKING POINTS:0:00 - David Goes Through Warm Leads From Lead Mining Pros3:38 - Seller Explains Why He’s Interested In Selling8:04 - Finding Out What The Property Is Currently Rented For9:05 - Checking On Repairs12:53 - Digging Deeper Into The Seller’s Story13:51 - Talking To The Seller About Owner Financing16:38 - Thoughts After The Call19:19 - Q&A From The Audience24:17 - 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/

With sky-high interest rates crushing cash flow, a lot of investors are sitting on the sidelines. But not Chandler David Smith. In this episode, he breaks down the seller financing strategies that help him lock in properties in today's market — and how you can do the same. You’ll learn how to pitch sellers, structure your offers, and uncover the hidden pain points that make seller financing a win for both sides. KEY TALKING POINTS:0:00 - Algorithmize Your Life2:14 - The Solution To Finding Cash-Flowing Real Estate In Today’s Market6:05 - Why Sellers Are Incentivized To Take Lower Interest Rates7:27 - How Chandler Structures His Deals To Pitch To Sellers13:09 - How He Analyzes Which Deals To Buy14:46 - Outro LINKS:Instagram: Chandler David Smithhttps://www.instagram.com/chandlerdavidsmith/ YouTube: Chandler David Smithhttps://www.youtube.com/@ChandlerDavidSmith 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/