Itchy Brain

Welcome to episode of the Still Burning podcast. Michael, it's great to have you here. Can you give us a quick introduction?

Sure thing. I'm Michael Grinich. I'm the founder of WorkOS. WorkOS is a company that helps other companies, SaaS businesses, developers, with enterprise features in their app. When you build the next great product and you want to go sell it to bigger customers and grow your business, you'll talk to security IT people and procurement, and they'll ask for things like single sign-on, SSO, SAML authentication, SCIM provisioning, access control, permissions, logging — essentially all this stuff that isn't really the fun stuff to build. We like to say that we help make your app enterprise-ready and help you grow and scale.

And that was obviously a well-polished, carefully crafted message. How did you get excited about enterprise-ready features?

I started a company before this where we had built an email client, kind of like Superhuman or Gmail. This is back in 2013, 2014. We got a bunch of users. People really loved the app. But we hit all these headwinds trying to actually sell it into businesses. And really businesses are the ones that pay for software. I realized that this is just this huge gap. Every single company building products was going to hit it. It fit the same type of infrastructure layer problem space that I'd seen companies like Plaid or Stripe do in FinTech. So I looked at it and I was like, I think you can actually build a service layer to solve it. And I love building things for developers. There's nothing better than building a service or a tool or a platform for other engineers. It's really hard to do, but I think it's the ultimate version of baking software. It's building software for other software people.

Yeah, I think that's one of the interesting things about your position right now is because you're selling picks and shovels into a gold rush, you get to see what everybody's using the picks and shovels for. Are there things about that that have surprised you?

We power these capabilities inside previous era companies — Vercel, Webflow, Carta. We also do it now for ChatGPT and Claude and Cursor and Perplexity and all these AI products. What I end up seeing is that all of these companies actually end up going through kind of the same go-to-market motion as they go upmarket. They all think they're unique and different. But if you look across all of them, you're like, they're kind of all doing the same thing. The biggest change by far over the last year, year and a half, is everybody's growing faster. The software industry is just at light speed. We can all go faster, grow bigger. Bigger companies are adopting software faster than they ever have before. The TAM has gotten bigger. The AI wave is pushing everybody forward, not just the big AI companies.

Yeah, I was at Gusto for a while and we had a similar view into small businesses because we could see their payroll. Before the economic numbers came out, we could see how things were shifting because people have to get paid. Can you see in your numbers that positive second derivative, that growth is growing faster?

Yeah, definitely. We see it in our own revenue as a company. We just raised our Series C a few months ago, and that was directly a result of our acceleration as a business. We're not really building that much different stuff. It's just the tide is bigger. The wave is bigger. And I think it's a few different things. The first is just that it's faster to build stuff. If we only had the coding models, that alone would create a run up in the market, like a super cycle. You've probably seen it using Claude — this thing will take 12 weeks and you're like, nope, we're going to do it in 20 minutes. But we have that plus the capabilities of the AI models make your product better. It's actually kind of like a human computer interaction shift — you can talk to stuff in natural language. I never want to write SQL ever again for BI stuff. I just want to answer the question I have about the company. The third one is that bigger companies are transitioning faster. The most surprising thing to me is the rate at which large companies are changing. I suspect some of it is because of COVID — during COVID, every company had to shift really fast. They did five years of IT transformation in five weeks. And so now they believe they can do it and they're all adopting AI extremely fast. You put all those things together and add capital on top — it's almost like we're activating the entire economy around the transformation of AI in a way we haven't done before, with the exception of maybe building the railroads.

I use the word geek to talk about my audience of people that I've been talking to my whole career and I use GeePaw Hill's definition of geek — someone who's highly creative, highly technical and highly desirous of being both. You strike me as a geek. When did you know that was a thing about you?

I've always been a bit obsessive about when I get into things. I like going deep. Even as a child, I tended not to have cursory interests. I would go deep on stuff and really learn a lot and read a ton of books and just fully absorb it like a sponge. But there was a turning point for me when I realized I could actually make stuff, that I wasn't just a consumer of it. I grew up in this small town in Oregon, McMinnville — a pretty rural area, about an hour and a half outside of Portland. I had this perception that the world was pretty static and not something I could change. It wasn't really until I was probably 18 or 19 that I realized, hey, all of this stuff is kind of malleable. All the people that have made things happen in the world kind of just did that. They just were normal people. They weren't gods that came down from the heavens. They just worked really, really, really hard. And I think that, you know, following that forward, building tools for developers is kind of a distillation of that. If you can build software for other software people, your impact is the set of all the things your developer customers build, all of their customers' customers.

And that creative impulse, that going from — there's this thought in my head which I now can't get out of my head until I make a thing in the world — and then I see the thing in the world and it feels so gratifying. That same kind of itch.

Yeah, I often call it like the itchy brain feeling. The most miserable I've been in my whole life, I think, was when I wasn't working. I had this period between that first company and WorkOS where I took like a year and a half off. And I was just trying to come up with ideas of what to do next, like exercise and catch up on life stuff. I was kind of miserable. I was like a dog without a tennis ball to chew. Just kind of aimless. And so I have found that if there's a thing I can run after and focus on, it helps me feel alive and useful in the world. I think the thing that made me not want to continue in school — not go to graduate school and PhD — I just got this feeling that I wasn't doing anything for the world. I just felt this desire to make things, but as a way to connect with people, as a way to be connected in the world and be sort of part of the global human ecosystem. And yeah, I just wanted to be connected.

Oh, interesting. Yeah, I think my motivation is a bit more selfish than that. I get that itchy brain, and I know it's not going to go away until I make the thing.

I mean, that's definitely part of it too. It's like a compulsion. Sometimes when I hang out with other founders, I sometimes feel like we all have the same kind of mental disorder a little bit. We all have this compulsion to make stuff or produce things. And it comes from different dimensions. But the ones that do it for long periods of time — if you're doing it for the external validation, that actually burns out pretty quickly. But if it comes from this place of just wanting to make stuff, you're just like — I just want to keep pushing and creating and exploring things. I heard this story once of some folks climbing in the Himalayas. An American climber with a Sherpa as his guide. He was getting totally exhausted and the Sherpa was just cooking, just climbing. And the guy asked the Sherpa, what is it that lets you do this? And the Sherpa said — when you climb, you look at the summit and you're constantly looking at the top. And when I climb, I just look at the step in front of me. Just being present and looking at the step in front of you. If you can enjoy the day, you'll enjoy the week. You'll enjoy the month. You'll enjoy your life.

Do you think that do you feel any evolution of your creative impulse coming?

I think at this phase — we're about 120 people — the problems actually get more interesting. I used to think that the very beginning phase was the most interesting, because you have nothing and the world is wide open. But it turns out there's so much that's out of your control at that phase because you're just trying to find something that connects with the market. Now we have a really strong team, we can do a lot of stuff, we can matter in the world. The ability to go and push things forward, to work with these significant companies in the world, to be a small part of their success — I actually find that more satisfying now.

What scares you about this? What wakes you up at night?

I'm generally a pretty big optimist. But what concerns me is that this scale of shift — everyone's talking about AI — but it's so different that I think people are a little bit fatigued. They've seen crypto, they've seen VR, they've seen things that didn't work out. They're like, oh, this is just another technology wave. Not realizing that at its core, it has this momentum around being a labor disruption. It's going to change the way we work, productivity. And that's the reason why it's going to be so enormous. It's also gonna have extraordinary effects across society and across what it means to work and have jobs. We haven't really seen that scale of white collar change before. I think it'll be okay on the other side. Like we'll make it through it. But it's going to be a big shock to the system. And I want more people leaning into it, seeing it — it's like kayaking. When there's a wave coming at you, the most stable position is to go straight into the wave, actively paddling. If you're not paddling or you're sideways, that's when you can get flipped. I just want people to paddle into the wave. Realize that this is a thing that's happening. And it's going to be great, but it's going to be a big wave to go over. And the way to hit it is head on.

All right, thank you so much for your time.

Thanks for having me, Kent. It's great to see you.