John Armstrong: The ChatGPT Prompt That Got Bloomington Buyers Their $5,000 Back

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: John Armstrong is the designated managing broker and owner of RE/MAX Rising in Bloomington, Illinois, and leader of the Armstrong Burns home selling team. A second-generation realtor since 1996, he has twice served as president of the Mid-Illinois Realtor Association and is a Hall of Fame member and past Realtor of the Year. He also hosts On the House, a weekly Bloomington Normal real estate radio show he has run for 15 years. Episode Summary: John Armstrong joins Under Contract to reflect on nearly 30 years in real estate, from payphone showdowns for keys to today's AI-assisted transactions. He shares how he builds and rotates a team of new agents, screens for inner drive, and uses ChatGPT as a daily business partner for training, marketing strategy, and even resolving a disputed home inspection dispute. He closes with a philosophy on karma and professionalism that he believes drives long-term referral business. What's Covered: Armstrong traces real estate's evolution from pre-internet days of controlling listing information and driving buyers around to today's bottom-of-funnel buyers who arrive already informed from online listings He describes his team structure as a training ground for brand-new licensees, moving them through stages until they graduate to independent production, while hiring a proven top producer to model best practices for newer agents He explains his interview method for spotting inner drive in potential agents, asking about the first time they made money as kids rather than taking claims of ambition at face value Armstrong details how national headlines miss hyperlocal nuance, citing his market's seller's conditions, five-day average market times during peak season, and a cross-market strategy pairing a seller's market sale with a buyer's market purchase He walks through using ChatGPT to staff internal panels, expand his marketing team into outside client work, and build a timeline of evidence that pressured a seller's agent into admitting undisclosed water damage, recovering a buyer's earnest money He closes on a philosophy of professional conduct and karma in the business, arguing that agents who communicate honestly and protect the deal's integrity earn long-term referrals even decades later Timestamps: 01:33 - Looking back at getting licensed in 1996 and growing up as a realtor's kid 04:45 - How market strategies flip between buyer's and seller's markets 06:17 - Structuring a team as a training pipeline for new agents 14:54 - What separates consistent producers from struggling agents 19:04 - What's happening locally in Bloomington that national headlines miss 21:19 - Lessons from 15 years hosting the On the House radio show 26:01 - Where team business actually comes from at different career stages 35:02 - Rethinking team culture around diversity rather than similarity 36:33 - Doing the right thing even when it costs a deal 43:48 - Using ChatGPT to resolve a disputed water damage transaction 48:42 - Closing thoughts on karma and professionalism in real estate