Dianna Caldwell: 210 Deals a Year in Cincinnati/NKY on Expired Listings and 3-5 Lead Pillars

Want the best insights from this episode and more in bite-sized nuggets? Sign up for our free newsletter at https://undercontractnotes.com/ Guest Bio: Dianna Caldwell leads a real estate team serving the Greater Cincinnati and Northern Kentucky markets, averaging roughly 210 deals a year with a staff of three and about 12 agents. She got her start in the late 1990s as a RE/MAX assistant in Nashville before earning her license in Northern Kentucky, and today runs her business alongside her son, who oversees operations and AI integration. Episode Summary: Dianna Caldwell shares how she built a 12-agent team doing roughly 210 transactions a year across two states, tracing her path from an assistant role in the late 1990s through the 2008 recession, when a hard push into expired listings reshaped her business. She breaks down how her team structures client acquisition around three to five pillars, manages follow-up through a CRM-driven pond system, and uses AI tools led by her son to support pricing and marketing. What's Covered: Dianna describes starting in real estate in the late 1990s as an assistant to a RE/MAX broker in Nashville before relocating to Northern Kentucky and getting licensed She explains two major turning points in her business, hiring a part-time assistant early on to free up time for money-making activities, and pivoting hard into expired listings during the 2008-2009 market downturn Her team structure includes an operations director, transaction manager, listing manager, marketing coordinator, and a recruiting mentor who trains new agents She lays out her advice for starting from scratch in a new city, including targeting a specific neighborhood, door knocking, mailers, and offering to hold open houses or create video walkthroughs for other agents' listings Dianna outlines her team's philosophy of working three to five lead generation pillars simultaneously, such as open houses, database calls, and door knocking, paired with time blocking to manage them She discusses her team's follow-up system, including a structured early outreach cadence and a CRM-driven lead nurturing pond, plus how AI tools and her son's involvement in an AI marketing academy are shaping pricing and operations work Timestamps: 00:38 - How Dianna got her start in real estate in the late 1990s 01:13 - Team structure and roles across 12 agents and 3 staff 02:03 - Team averages 210 deals a year across two states 03:12 - Turning points: hiring an assistant and pivoting to expired listings in 2008-2009 05:24 - Building a business from scratch in a new city with no database 07:55 - Client acquisition strategies and the team's database-first approach 09:23 - Why agents need three to five lead generation pillars 10:24 - Time blocking to manage multiple lead sources 12:36 - The team's follow-up philosophy and CRM lead nurturing pond 13:51 - The one thing Dianna would fix in her business with a magic wand 14:31 - How AI and Tom Ferry coaching show up in the team's operations 17:05 - What it would take to double the business in 24 months 18:14 - Predictions for the real estate industry five years out