Podcast Episode

84. This Too Shall Pass: Dana Gray on investing, building community, and giving back

The Kevin Dairaghi Show: Real Estate Investing & Personal Growth·Kevin Dairaghi | Real Estate Coach & Passive Income Strategist·23 March 2026·1h 4m

About this episode

Work with Kevin to get the confidence to build the life you want. - - - - The One with Dana Gray In this interview, Dana Gray shares her journey from post-2008 financial crisis to becoming a community builder and real estate investor in St. Louis. Discover her insights on real estate, community engagement, and the importance of giving back, along with practical advice for aspiring investors and tradespeople. 00:00 Introduction and Dana's Background 01:03 Getting into Real Estate After 2008 02:00 Starting with a Duplex and Rehab Challenges 03:27 Living in a Rehab Project and House Hacking 05:38 Advice for Young People: Trades vs College 07:20 Learning to Learn and Education in Social Psychology 09:38 Dana’s Involvement in Recreational Management 12:12 The Value of Fun and Relationships in Life 13:48 Assessing Happiness and Purpose in Life 14:44 Getting into Real Estate During the 2000s Boom 16:12 Managing Rentals and Building Community 19:26 Community Building Through Gardening and Relationships 22:43 Gardening as a Metaphor for Life and Real Estate 24:57 Dana’s Experience with Flipping and Long-term Holding 28:38 Tenant Relationships and Supporting Homeownership 34:22 Overcoming Hardships and Giving Back 36:00 Forging Moments and Building Steel Bridges 39:39 Dana’s Forging Moments and Personal Resilience 41:19 Handling Low Days and Staying Positive 44:25 Dana’s Work with Tower Grove CDC 45:22 Energy Efficiency in Affordable Housing 48:42 Future Plans and Community Impact 50:54 Connecting Real Estate, Art, and Film Locations 53:02 Advice to Younger Self and Overcoming Challenges 56:21 Quotes and Mantras for Tough Days 57:38 Final Words and Contact Information - - - - Kevin is definitely available for more MC and speaking opportunities. Have a group, you'd like him to speak to - Your kid's team? Your team? Your church? Just ask us! New linktree: linktr.ee/kevindairaghi  House Buying Website: www.RestoreSTL.com   Connect with Kevin Dairaghi! Website: www.kevindairaghi.com LinkedIn: www.linkedin.com/in/kdairaghi Instagram: @thekevindairaghishow Facebook: www.facebook.com/kdairaghi Get free access to some of the tools we talked about at www.kevindairaghi.com/tools You are who you surround yourself with. Join the Tribe! RATE & REVIEW this episode on Apple and Spotify. SHARE this episode with someone who needs it!   A huge thank you to our sponsors: Lois Mans with Farmers Insurance - Insurance! ‭(314) 283-1981‬ Greg Mans with Upright Construction - Roofs! (314) 374-1343‬ Adam Droege with CRS Realty - Property Management! (314) 325-8328 Jason Hudson with Red Maples Construction - Turnovers! (314) 312-2147 Nate Tomlin with Tomlin Heating & Air - HVAC! (314) 319-9678 Please reach out to them - they are my real estate team! Tell them Kevin sent ya!   Dealmachine Bonus: http://www.dealmachine.com/KDSHOW