The Data Stack Show - The PRQL: Willz Tolbert’s Journey Through Real Estate and AI

Episode Date: April 14, 2025

The Data Stack Show is a weekly podcast powered by RudderStack, the CDP for developers. Each week we’ll talk to data engineers, analysts, and data scientists about their experience around building and maintaining data infrastructure, delivering data and data products, and driving better outcomes across their businesses with data.RudderStack helps businesses make the most out of their customer data while ensuring data privacy and security. To learn more about RudderStack visit rudderstack.com.

Welcome to the Data Stack Show prequel. This is a short bonus episode where we preview the upcoming show. You'll get to meet our guests and hear about the topics we're going to cover. If they're interesting to you, you can catch the full-length show when it drops on Wednesday. Welcome back to the Data Stack Show. We have a special show that we're actually recording all IRL in our studio. So we found another boom, hooked up another mic, and we have Wills Tolbert here. And I'm super excited to chat with you, Wills.

Thanks for joining us. Yeah, man. Thanks for having me. All right. Give us, you're an entrepreneur. You've done a number of interesting things in building software and a lot of it relates to data. So just give us the quick flyover of your career. What were you doing before and what are you doing today? Yeah, so I got started as a commercial real estate broker at Lean Associates. Then I went on to do real estate development and I wanted to start like a tech enabled

brokerage but there wasn't too much tech and real estate that was very good in my opinion. So I kind of ended up starting my own company, MapSheet, that kind of became the company, turned into this SaaS company. I had no idea what I was doing or getting into, but... Building software is like building a building, right? Yeah, I thought so, but there was a few differences that I wasn't really prepared for. So yeah, I got a crash course and data and APIs and coding. And even though I still can't code, so that was fun. All right. And then after Mapsy, what happened and what are you doing today? Yeah, so we sold out a year ago.

Then I kind of took some time off to detox from all that. And then about last summer, last fall, started just tinking around, seeing what's out there. And obviously I've been paying attention to AI a lot. And I reconnected with a guy who was running the revenue team over at Cherry and it happened to be a perfect fit. So we decided to put our heads together and we started a new company called Ready.AI. So, Wells, we are constantly talking about data and AI on this show. I think our last guest is a put our heads together and we started a new company called ready.ai. So, Wills, we are constantly talking about data and AI on this show. I think our last guest was a little bit done with it, but by the end of it, I think we're happy to talk about it more.

But I'm so excited. You're two startups in now doing this data AI thing, one for real estate, one you're going to tell us more about. So we got to dig into that. But what other topics are you excited about covering? Well, I know y'all are excited about talking about commercial real estate data. I'm not as excited about it because I have some scars, but I'm happy to share all my lessons from real estate data because it is pretty complicated. All right. Well, we can do therapy after we're done recording. Yeah. I'd like that.

All right. Let's dig in. Let's do it. All right. That's a wrap for the prequel. The full-length episode will drop Wednesday morning. Subscribe now so you don't miss it.