I spent an hour with the crew at Under Contract Taking Backup, and it turned into one of my favorite conversations this year.
We covered AI in real estate, which you would expect. What you might not expect is how much of it ended up being about fear. The tools are the easy part. The hard part is the agent sitting there wondering if they are already too late, or whether leaning on AI makes them less of a professional. We got into that, along with confidence, ego, raising kids who are not afraid to fail, and why I think balance is a myth.
The full episode is below. It runs a little over an hour.
Jump straight to what you need
The episode is chaptered, so you can skip to the part you came for.
- Get to know the guest
- Using AI and tech in real estate, investing versus spending
- My road into real estate, speaking, and edutainment
- Becoming the first AI certified real estate agent in Upstate NY
- Our children and our inner child: overcoming fear, building confidence
- Balance is a myth, ego versus authentic self, and my favorite mantras
- The Spartan Race story: reality TV versus reality
- Misconceptions about successful REALTORS
- What agents lie to themselves about, and where real estate and AI go next
- Smart ways to use AI as a buyer or seller
- Outside the Corporate Box and beyond: adapting and overcoming
The through line
Every AI conversation in real estate eventually splits into two camps. One says the technology is coming for your job. The other says it changes nothing. Both are wrong, and both are comfortable, which is exactly why people pick one and stop thinking.
AI replaces tasks. It does not replace relationships. The agents who figure that out get their evenings back and spend more time in front of clients. The agents who wait keep doing the busywork by hand and call it dedication.
The reason we spent so much of this episode on fear and confidence instead of software is that the tools were never the obstacle. If you can send an email, you can use these tools. What actually stops people is the story they tell themselves about being behind, being too old for it, or being a fraud for using help. That is the part worth an hour of your time.
Where to start
If you finished that episode thinking okay, but where do I actually begin, here are the two doors.
The free AI guides are the no-cost starting point. They are written for real estate agents, not for engineers, and you can put them to work the same day.
The AI-Cademy Bootcamp is the six-week version, live with me, once a week for 90 minutes, capped at 25 seats so I can actually look at everyone’s work. You bring your business, your pipeline, and your voice, and you leave with an AI system running inside it instead of a folder of notes. The next cohort starts Thursday, August 6, and there is a fall cohort on October 1.
Ready To Stop Reading About AI And Start Using It?
Grab the free guides, or build the whole system with me in six weeks.
About the show
Under Contract Taking Backup is hosted by REALTORS Chelsey Smith and Lindsay Hart out of the Finger Lakes, and they describe it better than I could: imagine if HGTV got a little Bravo drama and a dose of NPR self-awareness. It is real estate, life, and stories, and it is a lot more honest than most industry shows.
Full circle moment on this one. Lindsay came on my show first and told the story of starting at the front desk in 2005 and ending up owning the brokerage twenty years later. If you liked her questions here, go hear her own story.
Follow the show: YouTube, Spotify, Instagram, Facebook, TikTok, and X. You can also find Chelsey at ChelseySmithRealtor.com and Lindsay at LindsayHartRealtor.com.
Thanks to Chelsey, Lindsay, and producer AlexGFilm for having me on and for steering this one somewhere more interesting than a tool list. Watch the full episode on YouTube.
