EP 141: Why AI Makes Human Connection More Important

Welcome to Real Estate AI Flash, the podcast that helps you understand how AI is changing real estate and the strategies you can use to win. I'm your host, Rajiv Saja. As AI becomes more capable, one thing is becoming increasingly clear. The agents who thrive won't be the ones who automate relationships. They'll be the ones who use AI to build stronger ones. In this episode, I sit down with Sky Michaels, founder of With Heart Coaching and former national coach at Compass to discuss how AI can help agents remove the friction that helps them from connecting with the people who matter most. We explore practical ways to identify who to contact, when to reach out, and what to say, while using AI to personalize conversations, create hyper-local content, and build the consistent habits that drive long-term success. If you're looking for practical ways to use AI to deepen relationships while staying authentic to your personal style, this conversation will give you ideas you can start applying right away. Here's my conversation with Sky. Welcome to another episode of Real Estate AI Flash. And today we have a featured guest, I should say, not just a guest, a featured guest, Sky Michaels. He spent 25 years in various roles. I'm sure we'll get into it in the real estate industry. And most recently, he's running his own coaching company. Prior to that, he spent several years as a managing director and national coach for a little known company called Compass. uh so we're gonna get into all things coaching and ai sky welcome to the podcast

I'm so thrilled to be here. We've crossed paths many times in our Philadelphia journey here. So it's great. Yeah,

for sure. And we are the listeners. He's also, by the way, a division one athlete at Syracuse University. Little known fact. Yeah. Which I discovered this morning before I got on. So, Sky, I gave you a very elevator pitch intro. Yes. For a career of 25 years. So walk us through how you got into real estate and bring us to today.

Yeah, yeah. So my quick and easy story, I graduated from Syracuse University. I was on the crew team there. Great college career. And I grew up poor. So, you know, growing up as a paperboy at the age of 12, I was always an entrepreneur growing up. But, you know, when you grow up poor, you crave stability. And I also knew I loved teaching, right? Teachers impacted my life. So when I graduated from Syracuse, I was a teacher and I was so excited. I got a job at Haverford High School. We're in Havertown, PA. Great school district, great job. I'm like, wow, I'm living the dream. And I woke up and I realized very quickly I was still poor. So very early on in my teaching career, I recognized I needed a side gig, you know, as most teachers have. Some people paint, move, do whatever. And I randomly fell into real estate and was like, oh, maybe I'll do this as a side gig. And that was 2002. And long story short, after two years of doing both, it very quickly did not become a side gig, it became a main gig. So I find myself working two full time jobs, and I had to make a decision. So 2005, I made the hard decision to leave teaching and I went full-time real estate. Long story short, I've done