Kevin Dairaghi | Real Estate Coach & Passive Income Strategist
The Kevin Dairaghi Show: Real Estate Investing & Personal Growth
Kevin Dairaghi is a real estate agent, investor, and coach sharing his decades of experience and wisdom with new and existing real estate professionals looking to take their next step toward financial freedom. Tune in each week to join the discussion from Kevin's Tribe - his support network of real estate heroes - as they discuss the personal struggles that held them back from business success and how they overcame them to begin building a community and legacy. You are who you surround yourself with. Join the Tribe!
Author
Kevin Dairaghi | Real Estate Coach & Passive Income Strategist
Category
Podcast website
Latest episode
Apr 13, 2026
Where to listen?
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Episodes
41: The One with Scott Krusemark: Navigating Asperger’s and Building a Legacy in Real Estate Lending 25.03.2025 59:21
Scott Krusemark shares his remarkable journey in the world of real estate investment. He recounts how reading "Rich Dad, Poor Dad" by Robert Kiyosaki inspired him and his wife to embark on their real estate adventure. However, their early days were filled with challenges, including overbidding on properties that eventually led them to bankruptcy. Scott highlights the invaluable lessons learned fro...
40: The One with the Greek Silver 18.03.2025 17:30
In this episode, we explore epic conflicts of ancient history, as we explore the leadership and strategic brilliance that can inspire modern entrepreneurship. Discover how the legendary conflicts of Marathon, Thermopylae, and Salamis reveal timeless lessons in leadership and strategic brilliance. We'll take you through the endurance of a Greek runner, the resolute stand of the 300 Spartans, and th...
39: The One with Dawn Augsten: Second-Gen Wisdom, Softball Coaching, and Rental Arbitrage 11.03.2025 1:04:23
Dawn Augsten from Florida shares her incredible journey as a second-generation real estate investor. Raised in a family of investors, she honed her skills in property management from a young age, and her college years further cemented her path in real estate. We compare and contrast our backgrounds—Dawn's lifelong immersion in the industry versus my first-generation, trial-by-fire approach in St....
38: The One with Jeff Nigh: Computer Engineering to Entrepreneur: Mastering the "Why" and Time Freedom 04.03.2025 58:57
Real estate investor Jeff Nigh shares his journey from computer engineering to success in property investing. He talks about how a mentorship program in Milwaukee reshaped his approach to real estate and the importance of relationships and personal drive in overcoming setbacks. We discuss the balance between entrepreneurship and traditional jobs, and how adopting an entrepreneurial mindset can bri...
37: The One with Ladonna Smith: Naples Property Pro to Purpose-Driven Affordability Philanthropy 25.02.2025 57:36
LaDonna Smith, a seasoned real estate coach from Naples, Florida, joins the show to share her journey from property management to successful investor and mentor. She breaks down the key role of mentorship and a growth mindset in building a thriving real estate career. The conversation also highlights Kevin's evolution from house flipper to entrepreneur, offering valuable lessons and experiences al...
36: The One with Mark Dolfini : The Time-Weary Landlord’s Guide to Becoming Time-Wealthy 18.02.2025 1:03:35
In this episode, we sit down with Mark Dolfini, a landlord coach and author of The Time Wealthy Investor 2.0, to discuss how to become "time wealthy." Mark shares his journey from "time weary" to mastering his schedule, offering practical tips on balancing time and financial wealth. We dive into his early real estate struggles, the crash of his portfolio during the 2008 financial crisis, and the l...
35: The One with Matt Kresko: Real Estate Networking Beyond the Party Scene to Personal Growth Mastery 11.02.2025 51:44
Matt Kresko shares his inspiring journey of leaving a stable corporate career to build a successful real estate business in St. Louis. He highlights the power of networking, particularly through LinkedIn, and why the relationship-driven nature of real estate captivated him. Matt and Kevin also discuss the personal transformations they've undergone, including shifts in lifestyle from partying to fo...
34: The One with Kellie Rhymes: From Short Sales to the Courage to be the "Bougie Baldie" 04.02.2025 1:06:22
When Kellie Rhymes first faced the challenge of scarring alopecia, she never imagined it would lead to the creation of the Bougie Baldie Podcast, an empowering platform for women facing hair loss. Her journey of self-acceptance and vulnerability, from hiding behind wigs to embracing her baldness, offers a powerful testament to the transformative power of sharing one's story. In our conversation, K...
33: The One with Megan Greathouse: Military Resilience, Stoicism, and the Shift to Multifamily Freedom 28.01.2025 1:03:54
Megan Greathouse shares her inspiring journey from military service to real estate success in St. Louis. She discusses her transition from corporate America, overcoming "shiny object syndrome," and staying focused on her goals. She also highlights her work empowering women through STL WIRE and STL REI Happy Hour, emphasizing the importance of networking and community support. Megan opens up about...
32: The One with Dr. Teresa Martin Esq.: The Legal Prophet’s Five-Generation Blueprint for Generational Wealth 21.01.2025 1:21:17
Dr. Teresa Martin Esq. (Dr. T) shares her inspiring journey of overcoming challenges to build a real estate empire. From receiving her first property as a high school graduation gift to passing down her legacy to her daughters, Dr. T emphasizes financial literacy, creative financing, and generational wealth. Key Takeaways: Generational Wealth: Dr. T’s journey started with a property gift from her...
31: The One with Bryan Schroeder: Aerospace Engineering to the Farm-Boy Roots of FasterHouse. 14.01.2025 57:20
Kevin sits down with Bryan Schroeder, a key figure in the St. Louis real estate scene. Brian shares his unexpected career shift from aerospace engineering to real estate, driven by his entrepreneurial roots in Garner, Iowa, and a late-night infomercial that sparked his interest. Bryan talks about the evolution of FasterHouse, his house-flipping and rental business, and how they navigated market ch...
30: The One with Eads Bridge 07.01.2025 31:04
Welcome to the season two premiere of The Kevin Dairaghi Show. Through powerful listener stories and historical examples, Kevin explores the significance of mental real estate, the balance between personal and professional lives, and the transformative power of relationships. Drawing inspiration from the monumental Eads Bridge and visionary leaders like George Washington and Thomas Jefferson, the...
29: Wrapping up 2024 23.12.2024 38:26
In this special episode, we’ll reflect on some of the most transformative stories of 2024, revisiting insightful conversations with our distinguished guests. Their personal experiences have provided invaluable lessons, all centered around our three core principles: The most important real estate is the space between your ears. Your personal growth drives your professional success. Building strong...
28: The One with Tim Grimmet: Farm Boy Roots and a Pastor’s Heart: The Path to Debt-Free Living 17.12.2024 1:03:20
Join us as we wrap up the first season of our podcast with an inspiring and insightful conversation featuring our special guest, Tim Grimmett, a respected figure in real estate investing. Tim shares his journey from corporate life to self-employment. In a chance encounter at Quick Trip, Tim took a leap into real estate, driven by determination and a hands-on learning approach. He reflects on the e...
27: The One with Bryan Housley: Ministry and Law Enforcement to CityScapes Short-Term Rentals 10.12.2024 58:50
In this episode, we are joined by Brian Housley, the founder and CEO of CityScapes Vacation Rentals, who shares his unique career journey and insights into the short-term rental industry. Brian's path to success is anything but conventional—having transitioned from a ministry and law enforcement background to becoming a thriving real estate investor specializing in short-term rentals. Throughout t...
26: The One with Amy Mahjoory: Leaving Dell Computers to Reign as the Private Money Queen 03.12.2024 53:25
Is it really possible to break free from debt and scale your business by leveraging other people's money? Amy Mahjoory shares her remarkable journey from a 14-year career at Dell Computers to becoming a successful real estate investor and coach. She offers priceless insights on private money lending, overcoming financial challenges, and the power of resilience and strong personal relationships. Sh...
25: The Tale of Two Illnesses 26.11.2024 41:33
In this episode of The Kevin Dairaghi Show, Kevin shares his journey from corporate life to solopreneurship in real estate investing. He discusses balancing business growth with his father's battle with cancer, emphasizing self-care, communication, and entrepreneurship's flexibility to prioritize family. The episode highlights resilience and unity amid adversity. Kevin shares anecdotes of rebuildi...
24: The One with Cheryl Zink: 24 Years of Corporate Excellence to Real Estate Renewal and LifeWave 19.11.2024 56:50
In this episode, Cheryl Zink shares her inspiring journey from a 24-year corporate career to becoming a successful real estate investor. After accepting a voluntary severance package, Cheryl found a new path in real estate, connecting with a supportive community of mentors and fellow investors. She talks about how this leap taught her the importance of smart decisions and building strong relations...
23: The One with Ryan Wessels: College License to Top Firm Founder: Building Three Doors 05.11.2024 57:44
Ryan Wessels, co-founder of Three Doors, shares his journey from earning his real estate license in college to building a top real estate firm in St. Louis. He and his partner, Jim, turned challenges into opportunities by embracing mentorship, flexibility, and strong partnerships. Ryan reflects on how his career and personal growth have been shaped by adversity, key business decisions, and the sup...
22: The One with Chad Wilson: Air Traffic Controller and Military Chief to Real Estate Mogul 29.10.2024 56:25
Chad Wilson, a dedicated realtor in St Louis shares his inspiring journey from air traffic controller to real estate mogul, revealing unexpected twists and valuable life lessons. He discusses how a unique opportunity from a pastor led him to build a top-performing real estate team in St. Louis, emphasizing the power of mentorship and strong partnerships. Chad also candidly addresses personal chall...
21: The One with Jonathan Rankin: The Electrician Who Leveraged Construction Roots into Commercial Success 22.10.2024 54:37
Jonathan Rankin, a prominent figure in St. Louis real estate, shares his journey from electrician to successful investor. Starting in 2009, he pursued real estate despite his mentor's advice, balancing both careers until going full-time in 2013. Jonathan highlights the importance of mentorship and the fear that motivated his success. In our conversation, he discusses how strategic partnerships, pa...
20: The Tale of Two Coaches 15.10.2024 39:12
Starting over in a new city can be intimidating, especially when leaving behind a stable career. Yet, that's exactly what Kevin did when he transitioned from engineering to real estate, moving with his then-girlfriend, now wife, Cami, from St. Louis to Asheville, North Carolina. Those steps into the unknown taught Kevin invaluable lessons about vulnerability, humility, and the power of relationshi...
19: The One with Jeff Coffman: Marine Corps Resilience, Manufacturing, and the PPC Marketing Edge 08.10.2024 57:47
Jeff Coffman, a former Marine Corps member who transitioned from manufacturing to becoming a leader in the pay-per-click marketing industry joins us today for another inspiring conversation. Jeff's story is one of transformation, resilience, and empowerment as he navigates the challenges of entrepreneurship and discovers the power of mentorship and strategic partnerships. With insights into his pe...
18: The One with Spencer Argueta: Reclaiming Family Freedom: From Colorado Relocation to Thriving Investor 01.10.2024 50:53
Spencer's move from Colorado to Missouri was a transformative journey. Relocating for her husband's job, she found freedom and a renewed sense of purpose in St. Louis. This episode highlights how major life changes can spark personal and professional growth, underscoring the value of healthy relationships and mental well-being. We discuss Spencer's transition from a reluctant real estate agent to...
17: The One with Adam Droege: Corporate Professional to a 100-Property House Hacking Empire 24.09.2024 50:43
What happens when a corporate professional decides to leap into the unpredictable world of real estate? Meet Adam, our inspiring guest, who narrates his compelling transformation from a desk job to a thriving real estate career. Initially acquiring his license just to purchase a home, Adam and his wife, Michelle, embarked on a journey of house hacking—renovating and selling homes for profit. Despi...
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