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Guest Bio: Casey McCoy is a real estate team leader with Keller Williams based in Evansville, Indiana, running a five-agent team that has grown roughly 50 percent year over year for the past three years. He got his start in real estate after a rough experience buying his first house at age 20, which led him to get licensed in 2010, and he has since built a business rooted in investment income, relationship-first client acquisition, and early adoption of AI tools.

Episode Summary: Casey McCoy joins Under Contract to share the winding, almost accidental path that led him from a foreclosure-threatened house hack at 20 years old into building a thriving real estate team in Evansville, Indiana. He dives into the mentorship moment that reshaped his entire business model, his relationship-first approach to lead generation and follow-up, and how he is already using AI tools like Claude to build custom real estate technology on the cheap.

What's Covered:

• Casey recounts buying his first house at 20 with three lined-up roommates, only to end up in foreclosure and upside down on the mortgage after a botched roof repair and a market crash, which unexpectedly pushed him into getting his real estate license
• He credits mentor Mike McCarthy with two pivotal lessons that changed his business: hiring help early by asking 'why are you stealing someone else's joy' and building investment income so he never has to pressure a client to transact
• Casey explains his go-to strategy for starting over in a new city with no database, which centers on visiting locally owned coffee shops to get introductions to well-connected community members, plus working expired listings for faster results
• He details his personal lead sources, including ditching business cards entirely to control follow-up timing, a Zillow partnership that converts about one in five leads into referrals, and strategic Thursday open houses paired with 100-door neighborhood knocks
• Casey identifies follow-up in the middle of his funnel as his single biggest current business problem despite explosive top-of-funnel growth, and shares client feedback showing people actually want to be followed up with rather than feeling bothered
• He shares his history experimenting with AI-driven real estate technology, from a $25,000 nine-month platform build in 2014 to recreating similar functionality in a weekend for about $50 using Claude, plus his vision for a client-facing AI assistant trained on his own conversations and local market knowledge

Timestamps:

00:00:39 - How Casey got into real estate after running out of college money

00:03:37 - The roof repair that never happened and led to foreclosure

00:06:03 - Getting licensed with his last $500

00:08:06 - Mentor Mike McCarthy and the turning point conversation

00:10:50 - Why are you stealing someone else's joy, the hiring lesson

00:12:46 - What Casey would do first starting over in a new city

00:17:09 - Why Casey stopped using business cards

00:19:08 - Zillow partnership and referral conversion rates

00:22:14 - Casey's follow-up philosophy and building relationships over transactions

00:26:51 - The one problem Casey would fix with a magic wand: follow-up

00:31:53 - Casey's early AI platform build in 2014 versus rebuilding it in a weekend with Claude

00:36:03 - Using AI-powered seller updates to guide price reduction conversations

00:38:04 - Casey's vision for a personal AI assistant trained on his own client conversations