Inspired with Alexa von Tobel
00:00:00 · Brian Distelburger
[00:00:00] S0: We are gonna go through a civilizational level change management problem. We have not seen anything like this in our lifetime. We're dealing with this this huge level of uncertainty. I don't think anyone can accurately forecast exactly what things are gonna look like in in, you know, ten, twenty years. But there are some things I think we can say today with a pretty high degree of certainty. One is just like the sheer output from agents is gonna be enormous relative to human output. We also know that we have a system in structure in society where individuals are accountable for work. So given those two factors, where you have agents producing all this kind of stuff, humans then become the bottleneck for the output of work. And so figuring out what that looks like for individuals, getting them in the roles where they can be successful and add a lot of value is gonna be a massive change and open up different roles and responsibilities that just did not exist even even two years ago.
00:01:02 · Alexa von Tobel
[00:01:02] S1: Welcome to Inspired. I'm Alexa von Tobel. What if every single employee at your company had a world class coach in their corner, someone who knew exactly what they were working on, where they were struggling, and how to help them grow. That is precisely what Max Shaw, Brian Distelburger, and Mark Tanner are building at Windmill, an AI powered people platform that sits at the center of how companies develop and manage their talent. As AI makes every single employee more powerful, having the right person in the right role matters more now than ever. Since launching in November 2025, they've already reached over a 100 customers and are growing rapidly, including Kalshi, The Farmer's Dog, Rho, and more. We are so proud at Inspired to have led their 8,000,000 seed round and deeply believe in their mission. In this conversation, I sat down with Max and Brian, two of the people that helped build Yext into a multibillion dollar company that they took public. We're gonna talk about why performance management is so broken, how AI is going to make managers dramatically more effective as their teams grow, and why despite all the noise about AI and jobs, they're genuinely optimistic about what's coming next for people at work. Let's dive right in.
00:02:12 · Alexa von Tobel, Max Shaw, Brian Distelburger
[00:02:12] S2: If you're running a startup, we know things like managing equity and communicating with investors are always top of mind. Carta has built a connected suite of tools that over 40,000 companies use to do just that. Their platform of software and services helps you lay the groundwork so you can focus on building. To learn more or get started, visit carta.com. And with that, let's welcome, my two pals, Brian and Max. Guys, first of all, thank you so much for coming on today. I'm really excited to talk about everything you're building at Windmill. [00:02:40] S3: Excited to be on. Thanks for having us. [00:02:42] S2: Since there's two of you, why don't we start with the basics? Could you each just give us sixty seconds on what you've done before Windmill? Brian, starting with you. [00:02:52] S0: Okay. So immediately before Windmill, I founded a company called Yext. Got up to a few thousand employees. We went public in 2017. Before that, I founded a bunch of random companies since I was in high school, a motorcycle shop, landscaping business, and stuff like that. Also on the board of Tech NYC. [00:03:12] S2: Let's go NYC. Max, what about you?
00:03:12 · Alexa von Tobel, Max Shaw
[00:03:12] S2: Let's go NYC. Max, what about you? [00:03:16] S3: Awesome. Well, I met Brian at Yext. I was there for ten years where I led product globally. I would... Did not have any motorcycle businesses, but I'd... I have built a bunch of random apps over the years, a lot with my other cofounder, Mark, who we've met in college together. And the most prominent is probably this app called Gifjif, where you can put your face on a GIF. This is all pre AI, but it was a lot of fun. [00:03:43] S2: So we just announced, and I am so excited that Inspired is your teammate, early stage seed investor here, and everything that we're building with Windmill. And before we just even, like, dive into the future, what is Windmill in plain English from your guys' head?
00:04:01 · Max Shaw
[00:04:01] S3: Yeah. So Windmill's the missing system that I've always wanted throughout my career. I was at Yext. I started as an individual, then eventually managed a small team, and then I ran a pretty big team. And it felt like this... There's this missing system that allowed me to stay on top of my team, to understand how people were developing, and to help them grow in a scalable systematic way. And that system just didn't exist. And in the age of AI, one of the things that kind of been part of the founding story since the beginning is that as each individual employee gets a lot more leverage with AI, everyone is running their army of agents, people end up mattering a lot more. And having the right person in the right role with the right set of responsibilities is now more important than ever. And we think the companies that win in the future are not gonna be the ones that automate the most people out of their jobs. They're gonna be the ones that put the best talent in the exact right opportunity for them to excel. In order to do that, there's this missing system that just doesn't exist. You have your org chart in your HR system. You have all your productivity apps where all the work actually happens. You have, like, a performance review system that's disconnected from both of those. And if you wanna start to use AI to help understand your talent, understand your people, we think the most important asset going forward, you need a new system that synthesizes all this context together. And so Windmill is building that missing link. We call it the context graph for your people. And with that, you're gonna be able to develop talent and to scale out organizations and to orchestrate your teams in an entirely new way. And so we're building that missing foundation.
00:05:38 · Alexa von Tobel
[00:05:38] S2: Let's talk status quo, guys. I, you know, was a manager at a Fortune 50 company. I I I... You know, when I was trying to learn best, I'm very familiar with performance reviews. They're always quite awkward. I think many companies don't even do them. And yet when I think about in my own career, probably the moments that I'm most grateful for have been moments of genuine, thoughtful feedback, where somebody said to me, you're great at this. Keep doing it. You're terrible at this, Alexa. There's always been a long list. Do less of it. Or here's a tool to make the thing that you're not good at better. I mean, truly, and I could not be more sincere in saying that that the gifts of my career have been moments of really thoughtful but critical feedback. Where upon reflection I was like, gosh, feedback is a gift. And I know we all sort of say it, but actually don't mean it because it sucks. It's such a gift. It is such a gift. What's the status quo right now, Max?