Why the Smartest Entrepreneurs Are Choosing Community Over AI | Heather Simpson
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Why does Heather prioritize community over AI in entrepreneurship?
What is up, the entrepreneur? DNA, AI, AI. It's all anyone can talk about. Now, this is gonna be a great topic because everyone wants to talk about AI, except for my next guest. We might talk about it, but she cares more about human connectivity, uh, communities, clubs. Heather Simpson is here. How are you?
Hi, I'm so great. Thanks for having me this morning.
Yeah, I'm excited about it. In in uh you have a wealth of of resume. Obviously we can go into all that, but I really wanted to start out out of the gates. Everyone in their mother wants to talk about the new AI thing and you're leaning in to connectivity. Tell me why.
Yeah. Because I think that far too many people are outsourcing their thinking and that's becoming a really big problem. And the more disconnected, the more plugged in we become, we become disconnected in person. So that has a ripple effect of things that don't impact us as humans very positively and can actually bring on a lot of negative things into our world. As I think we're continuing to see more and more. It's hard to know what's real when you're online, but it's it's so easy to actually like tune in, read body language, read tone and connect with people face to face and be able to tell what's real. And so I think that now more than any time in the pandemic era, I think that now bringing people together and having connectivity in person is more valuable and important than it's ever been before.
Now let's take a step back. You started in the real estate space.
Okay.
I
did. Like most of us awesome entrepreneurs.
Amen, girl. Amen. Right. Uh and so I think my audience knows I have twenty years in the real estate space. And so you made a very brave decision, right? You stood up for what you actually believed in, what you wanted to do. I actually used the the um I don't like the people to say what's your why and follow your passion. I think that's a little cliche and over uh delivered. I actually like to think about what's gonna actually be the longevity of your business. And you're only gonna have longevity of your business if you actually enjoy what you do or at least believe in what you're doing. Hard to believe in real estate, right?
What problem does Heather see with people outsourcing their thinking?
Like I didn't wake up For 20 years, and I'm sure you didn't like God, I love real estate. It drives my you know, you never have those days, right? So, but you did. You said, you know what, I'm gonna make a hard pivot. I'm gonna make the choice to go into a direction that I actually desire to go into. Did you get any Blowback from some of the closest people around you?
Um, I think I've always just taken a different path. And so yes, the people closest to me have always been concerned with the choices that I have made because they rather me take the safer route. And, you know, what I was really doing in real estate at the time was very like agent focused. Like, yes, I did do um property development, I did do help clients buy and sell, but mostly where I found my greatest like gifting and joy was really helping agents behind the scene and develop their brand, eventually help start a couple of brokerages and really be kind of the first one, at least in our area, um, back in like twenty ten where it was like very agent focused instead of brokerage focused. And so deciding to kind of remove just the real estate umbrella from that and see how I can do that just for entrepreneurs in general and specifically for me, my audience is women, that was a very important shift and
And I think it was yes, like what is Heather doing now? But also when you see now and you look back the trajectory of like all of the things that I was doing in real estate and helping build brokerages and helping build people's careers. And now what I'm doing, the common thread is still there. It just changed from just real estate specific to to be like, why don't we do this for all businesses? Why don't we help people? really develop and then now, you know, everybody has a personal brand and And that's not a new thing, but at the time it really was. And it was about a company, um, more than it was about an individual and a person.
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Chapters
8 chapters
1
Why does Heather prioritize community over AI in entrepreneurship?
0:00–2:17
2
What problem does Heather see with people outsourcing their thinking?
2:17–8:28
3
How did Heather’s 20‑year real‑estate career lead to a pivot into community building?
8:28–14:16
4
Why did Heather choose to focus specifically on women entrepreneurs?
14:16–21:57
5
How does Her Connection Hub use AI for systems without replacing the human voice?
21:57–28:33
6
What challenges does a physical coworking space face in the 2026 economy?
28:33–35:27
7
How does Her Connection Hub design its spaces and programs to foster connection?
35:27–40:31
8
What is the story behind the upcoming book “Shattering Glass” and how can listeners get involved?
40:31–42:10
Speakers
1 identifiedMore from The Entrepreneur DNA
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