Remixing Innovation through Effective Leadership with Michael Grinich, Founder of WorkOS

(Intro Narrator at 00:00:00) Today, we're talking to Michael Grinich, founder of WorkOS, about how companies can cross the enterprise chasm and why everything in tech is a remix. You're listening to Joel Beasley, Modern CTO.

(Michael Grinich at 00:00:18) CTO.

(Joel Beasley at 00:00:19) So I was maybe a couple seconds late to the interview because I had checked out your Twitter.

(Michael Grinich at 00:00:24) Oh, no.

(Joel Beasley at 00:00:26) Yeah, yeah. And you had posted about how somebody I know—you had posted that somebody ripped off the WorkOS website.

(Michael Grinich at 00:00:33) It's amazing.

(Joel Beasley at 00:00:35) Yeah, yeah, they did.

(Michael Grinich at 00:00:36) They did.

(Joel Beasley at 00:00:36) They did a pretty good job ripping it off.

(Michael Grinich at 00:00:37) It's pretty good. Yeah, yeah, yeah. It's, you know, sometimes people rip stuff off and do a poor job at it. You know, like, oh, you didn't really capture the essence. But this one, they did. They really captured all the bits and truly cloned all of the good bits of it. So that's fine. It happens when you do good work. We're going to redesign it, you know, in the next few months anyway.

(Joel Beasley at 00:00:58) It'll keep them busy. Then they'll have something better to copy.

(Michael Grinich at 00:01:00) Yeah, totally. Yeah, yeah. That site took us a while to kind of come to a place where, you know, it was really like a new brand introduction for us as a company, new visual identity. And it was a lot of work, not to actually get to the design where we converged to, but just redesigning and redesigning and redesigning. Like, it's not there, it's not there, it's not there. And then finally, it kind of clicked. And I think it's been over two years since we've had it out, and it's kind of stood the test of time during everything that's happened since then. You know? But it's time for something new at some point.

(Joel Beasley at 00:01:31) Yeah. I actually like the strategy of copying an expert, copying the leader. And then when you get enough skill and you can mimic them correctly, then you can start to improve and freestyle on top of it. But I think it's a valid strategy.

(Michael Grinich at 00:01:44) Totally. I mean, it's the spirit of the web. I mean, that's what I did when I was a kid. You know, View Source was my teacher. That's how I learned how the internet worked and how CSS worked and how people made things. The unfortunate thing with people that have, like, minification systems for JavaScript or CSS is it's really hard to dig in and actually see how things are operating. I understand why people do it for performance and because your build systems are huge. But it's one of the most amazing things about the web is actually you can kind of pull back the layers and actually go see what's happening under the hood. And I don't get upset when people copy us at all. I mean, it's the way that people learn. You're totally right in that. It's also just such strong validation that what you made, like, resonated with someone. Someone saw it and they were like, oh, I want this. I want to make something just like this to feel what it's like to get this out. It's fine. It's kind of like a gift that you're giving other people making things. And, hopefully, at some point, they'll, you know, make their own stuff as well.

(Joel Beasley at 00:02:44) Yeah. It's a good way to learn music, right? To feel what the rhythm is like, to understand timing, how long these notes come out. And then you understand how the greatest songs feel to sing and play them, then you're in a better position to write great songs.

(Michael Grinich at 00:03:00) I was reading about the Beatles, you know, how they formed, most iconic band of all time. And they played in a cover band in this pub in Liverpool, I think, for, like, close to ten years or something, playing every single night. And they weren't playing their own songs. They were playing other people's songs and just, like, playing them again and again and again and just ingesting that. And that was, like, the genesis of their creative style and their music. You know? Like, you talk to any musician, of course they play covers. It's how you learn. And so I don't think it needs to be that different in the technology world. I think there's sort of an ego or pride that comes when things get ripped off or people are just kind of, like, personally pissed around it. You know? Like, go do your own thing. But if it's someone just starting off in their career or just trying to learn what it feels like to create something really great, sometimes, you know, imitating excellence is a way to get you to that finish line, and it can inspire you for the next stage as well. I think there's, like, a lot of value in that, and we shouldn't be punishing people or talking down on them for doing that. The role of people that are doing the work that those are copying should just continue to be doing great work, not look behind, just keep looking forward and sort of leading the industry. So the fact that we got copied, I'm like, oh, that's great. It means that we actually pushed the boundary there, and now we have the opportunity to do that again. And hopefully, actually, people will copy the next thing that we do.

(Joel Beasley at 00:04:24) Yeah. Well, it's a great indicator of maturity. If you look back at it upset, you clearly haven't reached that level to where you actually have realized that you are the leader, and this is how people and things grow. So the simple fact that when you look at it, you're like, this is awesome, and you post and you tweet about it. It's like, yep, they get it. They understand what it means to lead.

(Michael Grinich at 00:04:45) Yeah. We try not to copy too much stuff ourselves directly like that. You know, that's quite a direct copy. But we do look at a lot of other work. I mean, internally, we have this Slack channel just called Inspiration. And it's just stuff that people share that they really like, that they kind of see other companies make that they're like, wow, this is super well done or really tasteful or just really creative in a different sort of way. And it's not what you would imagine with, like, just everyone cloning Stripe's homepage with gradients or whatever. There's a wide variety of different things that we look towards for inspiration. And that's kind of how I've approached things in my own life is, like, trying to find things that are either software products that people have made, experiences that people have. Like, we think about our support team, how we support customers. And a lot of our customers are engineers, you know, which are very discerning about the type of support that they want. How do we create, like, an amazing experience for people like that? I'm always looking for new things to be inspired by. I mean, I just bought this on my desk, one of these guys. You've probably seen these around Twitter and everything.

(Joel Beasley at 00:05:45) No, I haven't. What is that?

(Michael Grinich at 00:05:45) There's this company, Rabbit. It's like an AI-connected, kind of like voice interface device. So it's kind of like ChatGPT, but you can talk to it. It just has a button. It's designed by this company in LA in collaboration with the Teenage Engineering folks, which are kind of all the rage on Twitter, their audio devices. It doesn't do much today. You know, it's kind of a little bit of a one-shot device, but the idea around it is like a new way to interact with computers and connect with technology.

(Joel Beasley at 00:06:16) What does it do?

(Michael Grinich at 00:06:16) You can talk to it. You can essentially talk to it like ChatGPT. It has a camera in it, so you can hold it up and say, well, what am I looking at? What is this? Translate this text from Chinese, speak it back to me in English. Here's the stuff in my fridge. What can I cook? Kind of all this stuff is built around the same language models that OpenAI has built. Their idea, though, is that it'll be an interface to be able to do things like play music, connect it to your DoorDash to order food. It's called the Rabbit. People can go Google it listening to this if they want to go poke around. But it's just a new take on technology. It's just very different. You know, you look at this thing, it doesn't look like my iPhone. It looks like a toy. I am intently curious about all these types of things, how technology is changing. And, you know, WorkOS is like an enterprise software API for developers. It has nothing to do with AI today. I mean, we support a lot of AI companies, but we're building this kind of very different type of a product than maybe what these guys are doing. But I still find that there are areas everywhere, if you look closely, that you can draw inspiration or ideas or creativity from. And we have that as a culture internally as a company. Like, it's not just me doing that. Other people are finding interesting stuff. And from a brand perspective, I mean, we draw inspiration not just from, you know, Apple or Stripe or something like that, but from streetwear brands, you know, like skateboarding companies, music labels that are doing events, restaurants, hotels, like all these different areas where people are creating products and experiences. So when we copy things, I think people don't necessarily see it because we're copying something maybe that's from a different industry or a different category and bringing it in. And it feels very fresh, you know, when it's landing in our stuff because people haven't seen it before. But there are traces of it from other places. There's a lot of good stuff that we've brought in.

(Joel Beasley at 00:08:05) So I started this past year making YouTube-specific content.

(Michael Grinich at 00:08:09) Mhmm.

(Joel Beasley at 00:08:09) There's a culture on YouTube that's called copy plus interest. Right? So I'm going to copy you, and it's okay if I copy you as long as I put a twist on it. And so people will do these contents where they're like, a new content format will start to emerge in the algorithms, and people will copy it, but twist it a little bit in their own way. And so everyone's got this feeling, all the creators, because content is iterating at significantly faster speeds than software, right? Because it's just people. And so, yeah. Copy plus interest. And it's even more beautiful. And when we were experimenting with different content, we would do that. We would go over to this vertical where there's a popular style of content and be like, would that kind of work over in this other vertical where they're not used to that content style. And so we would mix and mash and figure out what really took. And that's just great products, and developers appreciate it, by the way. Arguably more so in a corporate product, right? Because you typically find the corporate products' usability lags behind the consumer interfaces and usability.

(Michael Grinich at 00:09:12) Totally. I know there's this documentary, this thing a while ago, called Everything Is a Remix. Like, everything comes from something else. Like, everything in creativity, there's not this pure genesis from the brain of Zeus or whatever that springs out. Everything is a remix from everything you've consumed, where you've drawn inspiration from. I just last week was going to the ballet in San Francisco. I love watching dance. It's just a fun thing. The San Francisco Ballet is incredible. But it's a performance of Swan Lake, which is a Tchaikovsky ballet. And I was listening to it, and I was like, oh my god, I hear Star Wars. I hear Harry Potter. Like, there's pieces of it that you're like, wait, those six notes are in the Harry Potter theme song. And you're like, John Williams ripped off Tchaikovsky. He's copying him, and it's totally the case. He took the best bits from it, and that's why some of these songs are absolutely iconic. And I'm sure Tchaikovsky also copied from other people, you know, at different eras. So if you zoom out on a long enough timeline, everything is connected and there's these patterns across it. I mean, even Apple's design, when you look at it today, there's all these things that they pulled in from Xerox PARC, stuff that Doug Engelbart did, you know, that informed NeXT, which Jobs started, and then Next step. And then on the industrial design side, parallels to, like, Braun and Dieter Rams are just striking. I mean, there's so much stuff there. That doesn't mean what they did is not valuable. It's obviously incredibly valuable, and it's a great combination of things together. But, you know, just because people pull inspiration from different places and compose it together, it doesn't remove, you know, value from it. I actually think it's one of the hardest things to do is to take different pieces and kind of seamlessly blend them together, integrate them together. You know, I grew up playing music too. I almost went to college to be a jazz musician, funny enough. And in jazz, it's all about doing that, composing things together, bringing things together. Like, you can play a solo that's entirely new from your own gut. But people do these things, especially from musician to other musician, where they weave in patterns from other songs. And it's almost like if you know, you know. Like, someone will be playing one song and start riffing and improvising, and they'll pull in a melody from another song that maybe the audience doesn't even know. The combination of those things together and the ability to do it in this sort of super normal way, I think is actually the demonstration of mastery. It's, like, the most insane version of excellence or craft is being able to take those things and put them together, you know, without missing a beat or missing a step in the case of dance. And it's not different. You know, technology, creating products and technology is an extremely creative pursuit. You know, I found it to be much more close to, like, writing a song than, you know, building a building or building something in your shop. It's this extremely, like, deeply creative pursuit. And the inspiration kind of comes from the same place. You know? Software designers, software engineers are a lot closer to musicians and artists than we give them credit for.

(Joel Beasley at 00:12:17) 100%. Yeah. I'm a software engineer and a musician, so...

(Michael Grinich at 00:12:21) There you go. Yeah. Totally. It's not uncommon to go on, you know, talk to people on podcasts or on Zoom, and the background behind them is covered in guitars, you know, or drum sets or painting or photography. You know? These things are deeply connected together. And a lot of the people I've met that, you know, are in software careers today, that's what they make, they didn't start off in that. You know, they started off making music or taking photos or painting or writing or in very different industries, more deemed the traditional creative industries. It's the same thread. You know? I find it's the same, like, the thing that drives you. Like, when you wake up and you're like, what am I going to do today? What's going to get me out into the world? What's driving me to, like, express my humanity, you know, to the world? It's the same thing. It's the same genesis. So, going back to copying and inspiration, I'm absolutely delighted and honored that someone could use what we've built as inspiration in a very direct way. And I hope other people do too, you know, can look at it and pull the bits from it that they think is good and that resonate with them.

(Joel Beasley at 00:13:29) What's the elevator pitch for what you guys do?

(Michael Grinich at 00:13:32) WorkOS—it's enterprise features in a box, or through an API is a better way to say it. So in the same way you can use Stripe for payments or use Twilio for SMS or customer communications, WorkOS is an API service that helps bring all the enterprise features to the SaaS app you're building, the cloud app, so you can go upmarket. You can sell to bigger customers.

(Michael Grinich at 00:13:51) So we help hundreds of companies today with things like single sign-on, like SAML authentication, plugging into directory systems so they can have automated user management, features around security, compliance, encryption, data retention, audit logging. We just acquired a company doing authorization, so access control—all this stuff that's really complicated to build in any SaaS app. We built that as an API, so it's a really easy-to-use, modern developer experience.

(Michael Grinich at 00:14:18) And the result is, if you're building an app, you can go upmarket. You can essentially unlock deals. You can go up to bigger companies and they can say yes and use your stuff. Otherwise, oftentimes deals will get stalled. They're blocked because you don't have these features.

(Michael Grinich at 00:14:30) WorkOS lets you say yes and go upmarket. We're like five years old. We have about 600 customers. A bunch of big ones people know—in the developer tool space, like Vercel, Netlify, PlanetScale. Some fintech companies like Plaid, Modern Treasury, Brex. Webflow's a customer, Indeed.com, Carta. Perplexity actually just launched on WorkOS a couple weeks ago.

(Michael Grinich at 00:14:54) Their Perplexity Enterprise is actually powered by a bunch of WorkOS features. So it's cool. We get to work with a ton of different types of companies, and we're always working with their engineering team, their technology development team, the engineering and product function, because those are the folks that otherwise would have to build this stuff. So we say, "Hey, instead of building it, use WorkOS."

(Michael Grinich at 00:15:10) We'll help you plug it in, get going, and scale with them as we grow. We have some companies paying us just a little bit to get started on a credit card. We have some companies, like a Vercel, much bigger contract, work a lot more closely with them for all of their enterprise customers.

(Joel Beasley at 00:15:25) Nice. Tell me about this acquisition you guys made, Warrant.

(Michael Grinich at 00:15:28) Yeah, so it's authorization, which is different than authentication. People sometimes say "auth," but this is like "authz," authorization, versus "authn," authentication. Authentication is really proving you are who you say you are, right?

(Michael Grinich at 00:15:44) So you say, "I'm Joel. Let me prove it to you based on this external system." That could be your Google sign-in, your phone number. In the enterprise, it's your enterprise identity system like Okta or something, and that system will say, "Yep, you're an employee of this company. You are Joel."

(Michael Grinich at 00:15:55) And that's a lot of what WorkOS has built over the years for the last five years. That's what we help companies with—the user object and the authentication. There's a next step past that, which is: what can you do? What data do you have access to? What capabilities do you have as a user?

(Michael Grinich at 00:16:09) What permissions do you have? And that's really complicated. It's really, really complicated, especially in really complex, data-driven applications when you have a lot of different resources and entities that have relationships between them.

(Michael Grinich at 00:16:25) There's a lot of different capabilities. If it's an app like a Dropbox that might have a thousand users in there in a big company, the authorization is really complex—different roles and different users across the system. And so we acquired this company called Warrant, which is a YC company from a few years ago. And they had built an entire framework for doing this, for doing authorization.

(Michael Grinich at 00:16:46) And it's very flexible. It's sort of like an authorization service layer, and it's modeled after something that Google built called Zanzibar. So Google released this paper, published this paper, I don't know, five or six years ago, about their internal authorization system they built. And they said, "Hey, we had spent ten years trying to solve authorization. We finally came to this design."

(Michael Grinich at 00:17:03) "We're using it at extreme scale. It does something like over 10 million authorization checks per second." Yeah, it's pretty high scale. Like, Google Docs and YouTube and a ton of stuff is on top of it. And they're like, "This is the right design." So in the same way Google released papers for PageRank back in the day, MapReduce for distributed computing, things like Spanner for distributed data storage, and even the attention paper, which is now the GPTs are based on, they released the Zanzibar paper. And they didn't release any code.

(Michael Grinich at 00:17:38) It was just like, "Here's the design. Here's conceptually how to build it. Here's why we know it works. Here's how we came to this." And so a bunch of companies saw this and said, "Hey, we should build it like this." Kind of like Kubernetes—that's the right way to do it. We should build it this way.

(Michael Grinich at 00:17:47) And so there's a handful of startups that are out there that are building this. And we started hearing from our customers, "Hey, we're interested in authorization. We're trying to figure out how to solve this. Do you guys have anything? Recommendations? You guys do authentication. How should we do authorization?"

(Michael Grinich at 00:18:05) So I started looking into it more, started looking at different options. We were considering partnering with different companies, looking at different options, because there's a handful of different startups that are out there with different levels of success—some open source, some not, some kind of web-scale ready, a lot not quite, built with different technologies. And then I met the Warrant guys, and they had taken this approach of building it in Go. It's very fast performance, open-sourcing the core of it, and just kind of building true to the Zanzibar paper, that model. And so as I talked to them more, I was like, "Hey, actually, we were talking about partnering, but I'm like, we could do a lot more if this was actually deeply integrated, if it was part of the WorkOS platform."

(Michael Grinich at 00:18:40) So it wouldn't be signing up for two services. They would play nicely together. In the same way when you use AWS—you know, having compute and storage and network, they're independent things. You can set them up by themselves. But having S3 next to EC2 is really convenient. It's really, really convenient. So, "Hey, we should actually combine forces. You guys should join WorkOS."

(Michael Grinich at 00:19:07) "We should build this together and use that as a new kind of product offering for our customers over time." So we just announced that in the last month. It's still fresh. We're still starting to integrate stuff. But the idea long-term is WorkOS, in addition to being able to do identity and user management and audit logging and authentication, we also can do authorization for even the biggest, high-volume applications.

(Michael Grinich at 00:19:18) And Warrant service is already doing millions of authorization checks. It's not at Zanzibar scale yet, but we think we can get there and empower the next wave of applications.

(Joel Beasley at 00:19:40) Were they physically located near you, or did they relocate? How did that work?

(Michael Grinich at 00:19:44) Yeah, so we're a distributed team. I live in San Francisco, mostly because I just like California and the Bay. It's a pretty solid place. Their team is down in LA, actually.

(Michael Grinich at 00:19:55) So I happen to—I met up with them in person a few times. I happen to be down there and got lunch with the founder of the company and met the team. WorkOS is a distributed team. We have a lot of people in San Francisco, unsurprisingly.

(Michael Grinich at 00:20:09) But we actually bring the team together at least twice a year. We did our on-site a few weeks ago as the Warrant team came and joined forces officially with WorkOS. And now we're off to the races. Literally, right before this call, right before this podcast recording, I was chatting with their team about some new product stuff we're doing.

(Joel Beasley at 00:20:27) Private stuff, I'm sure.

(Michael Grinich at 00:20:28) There's a lot of really exciting stuff coming this summer with WorkOS. We are really hitting our stride. The team is just absolutely cooking, I think, is the latest term. Yeah, it's cooking. Yeah, they're cooking. They're certainly cooking with gas. So, and authorization is one of those things for our customers.

(Joel Beasley at 00:20:46) What prepared you for all of this? What past experiences do you have?

(Michael Grinich at 00:20:51) Gosh. I don't know if anything really prepares you for starting a startup.

(Joel Beasley at 00:20:57) Isn't this your second one?

(Michael Grinich at 00:20:59) Yeah, yeah, yeah, yeah. And so, doing it the first time, certainly. This one's moving faster. It's a bigger TAM, faster-growing customer base and market and all that.

(Michael Grinich at 00:21:07) But, you know, any sort of life experience just helps you. Hopefully you go faster and get better as you grow. When I was growing up, I organized clubs. I ran my school's newspaper. I did kind of stuff like that.

(Michael Grinich at 00:21:20) But I think nothing can really prepare you actually for trying to take something from nothing to something. What the founding moment is, is truly pretty profound, to have something that's in your head that no one else believes in or exists, and you kind of manifest it into reality. It's extremely hard. It usually doesn't work.

(Michael Grinich at 00:21:51) You know, it's literally in 99.999% of cases, because so many things stop before they even become a company. It's just ideas. But when it does work, it's sort of one of these extremely intoxicating things to have been part of. And it happens every day with the company too. The new things that we build, the new things—people taking those from inception to reality.

(Michael Grinich at 00:22:11) But I don't really know, can I compare you? I built a lot of stuff. I was very curious as a kid. I would just make things in my garage and got into software. And then when I was in school, I was actually a physics student at the time, but I started building iPhone apps just to kind of pay the bills and make some money. This is back in, gosh, like 2008-ish.

(Michael Grinich at 00:22:34) No, 2009, going forward. And I probably built like 50 or 60 iPhone apps for random different companies. And I just started—I wanted to get really good at making stuff. Going back to the musician kind of thing—if you want to jam with other musicians and be like a session musician, you just gotta be able to play really well. You gotta be able to hang. You have to have mastery over your instrument.

(Michael Grinich at 00:23:00) You can't be struggling to just throw down chords or keep a beat if you want to play with other folks. And so I wanted to just get good at building stuff. And so I built a lot of mobile stuff, a lot of iPhone stuff at the time, and then a lot of web stuff as well.

(Michael Grinich at 00:23:20) I just love web engineering and understanding how the web works and web services. I think that's what let me figure out kind of what to build next. Now my job is, like, what should the company do? What kind of strategy? Where are we going? And I think the only reason I have any amount of intuition for that is a mixture of creativity about what's—or excuse me, curiosity about what's going on in the industry. And the creativity actually just comes from having built a lot of stuff and experienced it myself. You can make really good music because you've listened to a lot of music.

(Michael Grinich at 00:23:40) I think you talk to any musician, like, how much music do you listen to? You look at their headphones—you've got a pair of Beyerdynamics on, I think, which are great. These are some Sennheisers. You listen to music all the time if you're a musician. Constantly.

(Michael Grinich at 00:23:56) You're constantly absorbing and listening to stuff. And I think that the equivalent to that for startups or people doing is being curious about how people make companies, curious about business. Nowadays, I'm sort of an obsessed student around what makes companies work, how do you build products that people actually care about.

(Michael Grinich at 00:24:24) I started angel investing a few years ago. Not really to make that much money—it kind of, you know—but just to get involved and be like, "Oh, I wonder how this company is going to operate. How do I think about their possibility of success? What are the risks or not?" I think you just kind of get a little curious and obsessed around it. And hopefully over time, your judgment, decision-making, and sort of insight gets sharper and sharper and sharper, just like a musician. And at some point, you know, you pull one of these master-level musicians into a jam session and you just watch them, and just the stuff that comes out of their head or their fingers is just insane, right?

(Michael Grinich at 00:24:48) You're like, "How? Where did that come from?" And it's like, "Oh, well, that's 30 years of listening to music every single minute, playing every single minute, and refining the craft again and again and again." I think it's not dissimilar from one of those creative pursuits. So I don't know what prepared me. I kind of just jumped in.

(Joel Beasley at 00:25:07) Jumped in, got a ton of experience. Yeah. I was listening to an interview with Joe Rogan and Gary Clark Jr. the other day, and he said, to your point, he's like, "Yeah, I just go into the local record shop and I'm like, 'What do you guys got? What are you listening to? What's hot? What's going on?'" He goes, "And then I'll just get the record, and I'll either like it or I won't." He goes, "And I'm just constantly listening to new music and new artists and different ideas."

(Michael Grinich at 00:25:31) And they never stop. Never stop. You see these musicians in their 80s, their 90s, consuming. It's until the day they die, right?

(Joel Beasley at 00:25:40) Well, it's the process. The process is the success.

(Michael Grinich at 00:25:43) Yeah. In some way, I actually believe the effect that they make, the thing that they produce, the actual record itself, is just a byproduct. The products that we build are just a byproduct of the creativity and the drive towards understanding or inspiration or just the need to make something.

(Michael Grinich at 00:26:31) It's not really—I think that's the thing that's really misunderstood about Silicon Valley and tech and builders. I lived in New York for a couple of years and met people in the finance world, and just people could not understand why you would just make something because you want to make it. Just because you're compelled to create something because it's cool or interesting, or the feeling you get when you make it is just so good. You just love that feeling. You just have to do it. Everyone loves listening to music, I think, and engage with music. But I think for a lot of musicians, they make music because they just have to. It's just in their bones.

(Michael Grinich at 00:26:43) They can't not do it. And the record, the effect of it, is just a byproduct that lets them live their life and make enough money to eat and engage with the world and their fellow humanity. But the thing that drives is much, much lower. I've sort of asked myself why I created this job or career for myself, which in many ways is extremely stressful.

(Michael Grinich at 00:27:07) It's not conducive to a nice, relaxing quality of life. And the only place I've come to is it's just something that's either wrong or right with me. But the byproduct of it is making a company, is the startup. But that's not the goal.

(Michael Grinich at 00:27:24) It's actually the effect at the other side.

(Joel Beasley at 00:27:29) People make that mistake when they're trying to get money for the first time, as if the money is the destination. And it's like after you figure it out, you've come to understand that the money is the byproduct. It's the exhaust of being able to do something that's so incredibly useful to people and so valuable that they can't help but give you their money to do it.

(Michael Grinich at 00:27:50) Absolutely. I mean, imagine going and buying a car at the dealership and the guy's like, so what are you gonna use your car for? What are you looking for? And it'll help you find the right car. And you're like, oh, I'm just looking for a car that I can, you know, that's something that'll just burn some gas. You'd be like, well, you can do that with any car. What? You don't wanna go anywhere? You don't wanna do anything? Oh, I just want something that can put a lot of gas in and burn it because that'll feel good.

(Michael Grinich at 00:28:12) And it's like, no, no one does that, of course. You're like, no, I want a car. I have some community work, or I need to drive my family. I need a bigger car. Or I like going skiing. It has to be four-wheel drive or, you know, go into the desert or something. I think the same is true for companies. When investors look and they say, why are you doing this? What compels you? What pushes you to make this happen? It's very hard to be not genuine about it. I mean, people can come up with stories or whatever. But in my experience doing just a very little amount of moonlighting angel investing and talking to VCs, it's so immediately apparent when they're not into it for the right, you know, in my mind, the right reason. When it's just like, oh, I wanna do a startup, so all my friends are doing startups. I wanna do a startup because it'd be cool to say I'm CEO or something like that. Or I'll be able to talk about it at parties or something.

(Michael Grinich at 00:29:00) None of those motivations—yeah, super weird—and none of those motivations are lasting. They are all extremely fleeting. You can maybe hold on to it for a few years. But when stuff gets really hard or you're just pulling out your hair and you're at the ends, the thing that I think leads to perseverance, you know, passion people call it, is something deeper that holds you. I was reading that the word passion is an Italian root, I think, or it's Greek or whatever. But it literally means suffering. It comes from the same root as just to suffer. I'm like, yeah, in a sense, they are really, really connected. And suffering isn't bad. The Buddha says life is suffering. Existence is pain or suffering in that way. But I think there's this piece around finding the way that you can suffer in the way that feels the most like you.

(Michael Grinich at 00:30:01) Yeah, it's like my form of suffering that is really me. I think, you know, everyone talks about follow your bliss. I'm sort of like follow your suffering. Find what's the way that you suffer that just feels so uniquely who you are as a person or what drives you, and just kind of lean into that as your life.

(Michael Grinich at 00:30:23) Bury your shoulder into that.

(Joel Beasley at 00:30:25) Yeah, 100%. People got passion confused with this sort of like sugar, this temporary high of, like, oh, I'm passionate about this fleeting thing. But I heard, to your point, I heard a really good quote a few years back that said, find what you love and let it kill you. And I was like, well, that's technically accurate. You're gonna do something from now until the day you die. So knowing that thing that you're gonna let kill you is a weird way of thinking about it. But to your point of entrepreneurism, as you were talking, I was thinking, I was like, why do I do it? And I have to. And I wish I didn't. I wish I could be the best number two in the world and tag on to some existing company. But the problem is that I'm only a version of me that I respect when I'm doing something incredibly difficult. And I need the freedom and flexibility to do incredibly difficult things so that I push myself.

(Joel Beasley at 00:31:25) And the reality for me is that entrepreneurship is the gateway. It's the excuse to be able to do incredibly difficult things that are highly demanding. Because if I'm not doing that, I'll just devolve into chaos. And I need that difficult thing happening in my life in order for me to be the best version of myself.

(Michael Grinich at 00:31:44) Yeah. The most miserable I've ever been in my life was not when I was working a hundred hours a week, bleary-eyed, going nuts, not seeing my family, not exercising. Oh, it wasn't that. It was when I wasn't working. That's when I was truly the most miserable and in Iraq. And I think you just find the thing that drives and pulls you. I mean, entrepreneurship or startups are a very pure form of that. There's nothing else happening around you. You can't really take it easy. Startups are kind of the extreme sports version of business. It's tough. But I think for people that find it compelling, this is the quote: If you need convincing to start a startup, don't do it. No one would almost advocate—like, someone's like, should I start a startup? I wouldn't tell you to go suffer in a way that's not for you. It's everyone's personal choice, but—

(Joel Beasley at 00:32:43) I will tell you to suffer. So go suffer, because here's the thing. Suffering in a way that's wrong for you, you've done that before too. And you learn a ton from it, and you're like, I don't wanna do that. You learn with certainty what you wanna do when you end up suffering for something you're not that interested in.

(Michael Grinich at 00:33:01) Yeah, yeah. I totally agree. It's finding—you know, I hope that everyone finds that for themselves in their life. If you haven't found it, I think I encourage people to look for it because working a job that you don't really feel engaged with that's not satisfying is a form of suffering. You're losing out on this huge opportunity to have a different type of relationship with your work in terms of what you create. For a lot of people, I think they haven't found that. You know? And they won't.

(Joel Beasley at 00:33:28) A lot of people won't find it.

(Michael Grinich at 00:33:29) Yeah. Unless you push yourself or try, it's very uncomfortable. And I'm not saying everyone should start a company. Absolutely not. And that form of your work, it could be in other things outside of the way you make money too. It could be another dimension, whether you're volunteering in a certain way or where you're putting your kind of creative life force into. There's many different areas.

(Joel Beasley at 00:33:50) I've got some nine-to-five friends that work just normal jobs. And because I've got kids—I've got three kids under seven—and they do that with their family. So they take all that energy and creativity, and they take all of that and they apply it to their family. And they're usually some of the happiest people that I know, right? Because they just go to work, they check that box, they make that check, and then they go put all of their energy into building their family.

(Michael Grinich at 00:34:14) Yep. Yep. Totally.

(Joel Beasley at 00:34:15) Oh, yeah. Crossing the enterprise chasm. You had to throw enterprise in there. Crossing the chasm, the enterprise chasm. You gave a talk on this. Why did you do that?

(Michael Grinich at 00:34:24) Yeah. I mean, so I gave this talk. It's coming up on five years ago, which is wild. And it's on YouTube. You can see I'm kind of sleepy in it. I wrote it the night before and rehearsed it. And it's really the whole thesis around WorkOS, why I started the company. The cliff notes version of it, what I saw was that there were all of these companies that built amazing products. I worked at Dropbox when I was in college. So this is one of the examples. Built these amazing products, and individual users loved. Consumers loved using them. They brought them to work. People at the company started using them. Teams started using it.

(Michael Grinich at 00:34:59) And then when they went to really try to commercialize and grow up market, they stalled out their growth. It was very, very hard for them to actually get usage in the enterprise environments and drive revenue. And I saw it's not just Dropbox in hindsight, but companies like Slack, Notion at some point. And actually, my first company now with this email product we built. We had a very similar thing where it's kind of like Superhuman. We got a bunch of users, and it was very, very hard to get enterprises to use it. And when I unpacked that, one of the reasons was there was this huge technology gap. Essentially, all the features you need to go sell to enterprise were these really obscure, complicated, many legacy integrations that you needed to do that I didn't know how to build. Our team hadn't built them, and enterprise IT admins would essentially block the app if they didn't have it. And so the idea with WorkOS was to build this as a product, you know, in the same kind of scratch my own itch from what I saw.

(Michael Grinich at 00:35:50) But this idea of crossing the enterprise chasm, taking the product you've built and going upmarket, has really resonated with people, connected with folks. And I think the reason why is that it's kind of like a second moment after you get product-market fit. We talk about this in terms of becoming enterprise ready. So you build an app, you set up your Next.js app, you build this thing, you deploy it to Heroku or AWS or whatever. You throw it in Hacker News, Twitter. You get a bunch of users. That's great to get product-market fit, to have it start compounding, and even to raise some initial money. Get into Y Combinator or whatever, raise some seed money, hire a team, start building product. And everyone tries to strive towards that product-market fit, like Marc Andreessen coined.

(Michael Grinich at 00:36:33) But it's not enough. It's really just your ticket to the game, kind of your entrance fee. And once you have product-market fit, the game completely changes. And the game after that is how can you scale? Not can you get product-market fit, but how can you actually get your product into the hands of the most number of people? The bigger companies, get them to pay for it, grow, get more users, and actually build a machine around doing that. Not organic word of mouth. That stuff's great, but it's not enough to accelerate. All these companies that have won their industry, like a Salesforce or something, figured out this other side, going up to enterprise. And I think there's this piece around entrepreneurs or developers should ask themselves, you know, do I have product-market fit or not? If yes, am I enterprise ready? And what is the path to becoming that? Some of that is the technology features. That's what I'm trying to solve with WorkOS.

(Michael Grinich at 00:37:24) But in that talk, I go through a bunch of details. It's not just the technology. Your pricing you need to change, your packaging, kind of the different features that are available in your enterprise version, how you sell. You know, a lot of developers are like, no, just put up self-serve, swipe a credit card, we shouldn't have sales. I was talking to David Kramer from Sentry, one of the Sentry founders. And he has this thing where like, enterprise is dead. You should be able to put a million dollars on a credit card and self-serve, which I totally believe too. I love self-serve products. But it turns out there's this entire category of customers in the world. It's actually the majority of customers who just want to talk to you. They want to talk to somebody if they're going to buy something.

(Michael Grinich at 00:38:01) They're human creatures, we're social, you know, we have eyes to be able to look at each other. We exist in societies together. We need to talk to other people and understand what the product does. We might have some questions. We wanna understand how it maps into our life. And if the impact is really big, if we can understand the value that it's bringing, we'll pay a lot of money for a product or service. That's everything from the food that we eat at restaurants, to the colleges that we go to, to the cars that we drive, to the houses we live in. Those are products that we're buying. Software is no different.

(Michael Grinich at 00:38:34) And it turns out the people that talk to potential customers to help them understand the product, help them figure out the right fit for what they're looking for, so it'll truly be an impactful thing in their life. Those people are called sales. That's the sales team. And so teams need to, companies need to build sales teams as they go upmarket and go beyond just those early adopters, the people willing to use it really fast, test it. The crossing the enterprise chasm phase, which actually I have a podcast by that name, which is all about interviewing people who've done this.

(Joel Beasley at 00:39:06) Yeah. No, you know, let's we gotta promote it. What is it called?

(Michael Grinich at 00:39:08) WorkOS.com/podcast. It's called Crossing the Enterprise Chasm. It's the same name as the talk. I've interviewed the CEOs and founders of, you know, Vercel, Plaid, Netlify. A lot of them are our customers, but places like Cloudflare, you know, how they have done it and gone to market. Ramp, they're on a tear right now growing. All about just my curiosity around how companies go up market. But it's pretty transformative. It's change that needs to happen in the business's mindset, in the founder's mindset, and kind of the whole strategy of the company. And that talk that I gave five years ago or whatever was sort of entirely around that problem that exists in the market. The thing I was gonna say is the crossing the enterprise chasm, that phrase, the word enterprise is in there. People have maybe heard the phrase crossing the chasm. So, you know, talking about everything being a remix and copying other people, I copied that. That's a rip-off.

(Joel Beasley at 00:40:01) Oh, yeah. It's a good one though.

(Michael Grinich at 00:40:03) From this guy, Geoffrey Moore, who wrote a book called Crossing the Chasm, which is great. Everyone should read it. It's kind of one of the standard business books that are out there. Crossing the Chasm talks about in product life cycles, like new product categories in the industry, how you move from having very early adopters or early enthusiasts into the mass market and this gap that exists between the two. And it's really hard for products to get past. A lot of the products, like this one I was showing earlier, I don't know if this is gonna cross the chasm if I'm gonna see mass market people using it.

(Joel Beasley at 00:40:33) I don't think it will.

(Michael Grinich at 00:40:33) Maybe. Maybe. Maybe not.

(Joel Beasley at 00:40:35) It's problem is, hardware-wise, it's another piece of hardware to haul off. The only new hardware that I've introduced to my pocket in a decade is the AirPods.

(Michael Grinich at 00:40:46) There you go. Yeah. Yeah.

(Joel Beasley at 00:40:47) Cell phone, wallet, keys.

(Michael Grinich at 00:40:49) Sometimes AirPods. AirPods sometimes. Yeah. So it's tough to do. You know, Apple did do it with the iPhone, iPod before that.

(Michael Grinich at 00:40:56) I think ChatGPT has crossed the chasm. You know, it's in popular kind of vernacular now, in a sense. But a lot of products don't make it there. And there's actually a lot of techniques and things that people do.

(Michael Grinich at 00:41:08) In this book, Crossing the Chasm, he talks about that as a limiter to technology growth or evolution, just as an idea. And so people talk about how's this product cross the chasm or not. The thesis of the talk I gave was crossing enterprise chasm. I was like, there's a version of this that exists in B2B software, in SaaS. And it's one of the hardest things to do to cross this chasm.

(Michael Grinich at 00:41:30) And I had just seen this pattern of companies struggling to do it or failing to do it, actually, and that leading to in many ways, they're not capturing their whole business market. And what I'm advocating for is that founders, entrepreneurs, people leading technology companies try to do this. Take it seriously. Once you have product market fit, turn your laser focus to, okay, how are we gonna become enterprise ready? How are we gonna cross that chasm and get our software into the hands of the biggest number of people out there? I mean, the TAM for software industry is enormous. You know, Microsoft has like a $3 trillion TAM or something. It's just giant. There's huge opportunities still there, but it's a blind spot, especially for product or engineering led founders who haven't thought about business or growth.

(Michael Grinich at 00:42:14) But it can be learned. You know, people can figure it out. I feel like I've figured it out by trial and error. And I've talked to a lot of people on that podcast that I was mentioning, the one I've recorded, who have done that, you know, over the course of their careers in different companies. You can see different examples of it, different types of companies, different stages, but they all do it. They all do it in some way that leads to their success.

(Joel Beasley at 00:42:36) I always, I pulled up the podcast page. We've had Drata on. We've had a number of common guests.

(Michael Grinich at 00:42:40) Oh, yeah. They're great. I just saw Daniel actually last night.

(Joel Beasley at 00:42:43) Oh, did you?

(Michael Grinich at 00:42:43) I was catching up with him. Yeah. They're great. They're a WorkOS customer. We power a lot of stuff for them.

(Joel Beasley at 00:42:47) Oh, really?

(Michael Grinich at 00:42:49) Yeah. They're awesome. So yeah. He was one of the early guests of the podcast. I actually interviewed a bunch of our customers and other folks.

(Michael Grinich at 00:42:55) Season three is coming out pretty soon, and it's got, we're just finishing recording, it's got a bunch of really awesome people. I just interviewed Sarah Varni, who's the CMO at Datadog. Before that, she was CMO at Twilio, the marketing lead at Twilio. Like, talk about iconic company. Adam Gross, who was CEO of Heroku for a while. He's a killer. So, you know, people around kind of dev tools, infrastructure, developer focused technology products I love talking to. That'll probably be dropping in the next, you know, month or two.

(Joel Beasley at 00:43:25) Yeah. So it's a small world.

(Michael Grinich at 00:43:27) Oh, yeah. Yeah. Yeah. It's really small. Yeah. Yeah. And when I, you know, I mean, I'm not a big shot podcast interviewer like you are. This is a tiny little thing I've been doing.

(Joel Beasley at 00:43:37) Are you enjoying it, though? That's all that matters.

(Michael Grinich at 00:43:41) Yeah. I mean, I just, you know, how do you prepare yourself for it? I was like, I don't know. The first one, I was like, I should buy a microphone. So, you know, I bought a microphone. And I was like, oh, yeah. I need headphones also. Let me get those on. And I think the podcast, I mean, the place I just come to it from, it's honestly my own curiosity. There are these people I'm just like, tell me about your business. I wanna learn about, you know, Twilio had this billboard in SoMa for years that just said, ask your developer. And I was like, that's such a cool, weird thing to put on a giant billboard, you know, super expensive in a major city. And so Sarah, I was like, what's the story behind that? How did you guys think about that? That's such a, you know, I think now it's been very iconic and they've, as a company doing developer marketing, people look to them for leaders.

(Michael Grinich at 00:44:26) But early on, they were pioneers. They were the only ones doing this kind of stuff. And so to actually hear the backstory from that, you know, I have millions of questions for these people. And so I'm gonna keep doing the podcast. Yeah. It's just going there. It's whenever I have time. Yeah. But yeah. It's one of the things of the job I just enormously enjoy. It's always one of my favorite things during the weeks to do an episode.

(Joel Beasley at 00:44:47) Well, Michael, I wanna be respectful of your hard stop. We made a podcast. How do you feel?

(Michael Grinich at 00:44:52) Oh, this is great. Thanks for having me on.

(Joel Beasley at 00:44:54) Thank you so much for listening. And if you found this episode useful, please share it with a friend or colleague who you think would get value from it. And if you have topics that you would like to hear discussed on the podcast, either add me on LinkedIn or send me an email [email protected]. Every time I get an email or LinkedIn message, it absolutely makes my day and inspires me to keep going.