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• Importance of domain expertise in entrepreneurship
• The need for resilience and adaptability in business
• The difference between building a company based on knowledge and experience versus following a trend or idea
• The challenges and downsides of being an entrepreneur, including the risk of failure and burnout
• The value of passion and personal connection to a product or industry
• A personal anecdote from Michael Grinich about a business misstep he made when trying to market his company in a way that wasn't effective for its user base.
• The speaker made a strategic decision to lay off a marketing team due to changing company direction
• The decision was difficult and had personal implications, including laying off employees and wasted investment capital
• The speaker reflects on the importance of being able to recognize when a mistake has been made and correct it quickly
• Making mistakes is a natural part of entrepreneurship and can be an opportunity for growth and learning
• The speaker credits their ability to bounce back from the decision to the support of their investors, who expect entrepreneurs to make mistakes and recover from them
• Building a company and dealing with criticism
• Overcoming emotional challenges as a founder
• Learning from failures and down moments
• Balancing risk-taking and conservatism as a company grows
• Maintaining a nimble mentality in the face of increased scale and complexity
• The difficulty of emulating successful companies without understanding their unique history and context
• Apple's shipping philosophy and ability to reinvent themselves annually
• Meta's transition from Facebook and its willingness to take risks
• The importance of discipline and courage in taking big bets as a company
• Companies that are able to adapt and evolve, such as Intel and Boeing
• The concept of "constant rebirth" and the need for companies to be willing to kill their own products
• The tension between speed and perfection in product development
• Importance of commitment to high-quality work and patience during the process
• Need for shared values and willingness to iterate and improve among team members
• Importance of taking time to get it right rather than rushing to ship a product
• Personal satisfaction and pride in creating something at a high level
• Difficulty of finding and working with others who share similar commitment to quality and excellence
• Value of having a small, tight-knit team that can push each other to excel
• Hiring process and looking for great talent across the board
• WorkOS values quality and discipline over company size and growth
• The company's flat organizational structure means everyone contributes to product development
• Flexibility in job roles is encouraged, allowing individuals to find their best fit within the team
• Small companies like WorkOS offer opportunities for people with non-traditional skill sets or backgrounds to have end-to-end ownership and make a significant impact
• Michael Grinich emphasizes the importance of teamwork and the role that his team has played in WorkOS' success
**Adam Stacoviak:** So, Michael Grinich... It's been a bit, man. I met you I think last year sometime, was very excited to talk to you, and I was just a fan of this idea of enterprise-ready. I'm a big fan of you find a scrappy way to get somewhere, and then you've gotta grow. But then that path to grow is obviously har...
**Michael Grinich:** Thanks. We'll have to get you one.
**Adam Stacoviak:** So where do we begin with this story? So obviously, WorkOS is beautiful, and amazing, but I think you've got a great design sense. Whoever's doing that for you all, from the copy to the actual design - just stellar, stellar work, hands-down. But your journey didn't begin here, obviously, because wha...
**Michael Grinich:** Yeah, it is sort of a weird story, because if you look at what we build, it's like an enterprise API infrastructure thing for these protocols like SAML, and things that most developers don't really know about, or don't get drawn in towards. And people often ask me, "How did you stumble into buildin...
**Adam Stacoviak:** Right...?
**Michael Grinich:** When I was an undergrad in college at MIT, I met a bunch of the folks that were working at Dropbox early on. And this is when Dropbox was pretty small. They were like 50 people, or something. Dropbox was started by MIT alums. So they would come to campus, and come to the recruiting fair, and throw ...
So I thought about that a little bit, but obviously not too much. I went back to school, graduated, and then after graduating, I had been working on this email project. It was actually like my capstone project in the computer science department. So the codebase was there... And it was this thing to synchronize email an...
And so I started this company to try to rebuild Outlook or Gmail with a much more modern take. And to build something that's really fast, and elegant, easy to use, and something hopefully that would help people communicate and get their job done a lot better. So I figured if you can help people communicate faster, help...
So I started working on that, took that codebase, and that became the core of the mailsync engine, and then built this app on top of it. And we obsessed around the design. Really obsessed around the experience of this app. I spent like three weeks looking at fonts, just typefaces -- because email's all text, right? The...
I hired a musician that did sounds for video games, and went to their studio for a couple days and just listened to like notification mail sounds that we were going to put in the app... Because the new mail notification sound you hear all the time. So we really went deep on this, right? Like we went really, really deep...
So anyway, we obsessed around the design of this product. We launch it, and people love it. And it was also open source. So developers loved it, it became a top project on GitHub, and we got all these people signing up. And I had just gone through the Dropbox playbook, right? Build a great experience, that people reall...
\[07:46\] So we started getting users everywhere from like NASA, to Uber, to Facebook, to the city of Minneapolis... Every single kind of imaginable type of user was just downloading it, signing in and using it. And the playbook I had was like "Hey, do the same thing as Dropbox. Just go find the organizations that are ...
And what happened is a few years later, as we started getting this adoption, I would go in those companies, like Uber, for example, and say, "Hey, there's 100 people here using Nylas mail. Let's get you guys on a team plan. Let's get you to pay for it for the whole organization." And this was the first time I really le...
Ultimately, this meant we didn't commercialize that product successfully. We got some people to pay for it, but it really wasn't growing in that means... And we've found that "Hey, in order to actually build this enterprise stuff, it's going to take an incredible amount of time." And during that moment, I actually went...
So we ended up just fully open sourcing it, shutting it down, pivoting the company... Nylas is still around, and doing well, and growing... But that idea of building a mail client essentially stopped. That died. And I took some time off, and when I was really trying to think about what to do next, I just kept coming ba...
Paul Graham famously has written and said "Make something people want. If you do that, everything else will take care of itself." And it obviously didn't. There was this missing step. And I realized that getting product-market fit - it's necessary, but it's really not sufficient to building a business. And if you don't...
And what I realized was -- why WorkOS exists is all this stuff that you need, you can really put it into a software layer. And that's what we've done. So things like authentication, and user management, security features, things like audit logging... All this kind of under-the-hood stuff that IT admins need - it's pret...
So I'm not clairvoyant, or anything, I just looked at the hard thing that everyone was doing, the hard thing that I had struggled to do at my first company, and then said, "Hey, let's just kind of go a couple notches down the abstraction chain and solve this from an infrastructure perspective for everyone." And it turn...
**Adam Stacoviak:** \[11:53\] Yeah. So Nylas - I do recognize you sweat the details on this email application. How, whenever you were examining -- because you sweat those details, right? The sound, the typefaces, the look, the feel, the user experience... How when you were sweating those details do you think you gapped...
**Michael Grinich:** I think it's a it's a situation that a lot of founders get stuck in, honestly. And the reason why is I wasn't like hanging out with IT admins. I hadn't worked as like an enterprise IT admin. I didn't have anyone in my network that was like a Chief Information Officer at a public company, or somethi...
I gave a talk on this a few years ago called "Crossing the enterprise chasm." It's like all about this change that companies need to go through as they go up market and commercialize. Some of it is technology. That's what we help people with, and provide, but it's kind of a different mindset. And the change that happen...
**Adam Stacoviak:** Is this like a market-leveler then, basically? Like, that you could be an early company, someone who does not have the engineering staff to build out these features, but you kind of get the Get Out of Jail Free card. I'm trying to find the analogy... Something that gets you past the gate, sooner, fa...
**Michael Grinich:** I was talking with someone once who kind of described what we do at WorkOS as like arming the rebels...
**Adam Stacoviak:** Okay...
**Michael Grinich:** You know, the next generation of software companies, helping them be able to go and compete with bigger organizations, helping them go at market faster... And I think there's a future where this could be possible. I think if we do our job right, at some point you'll be able to have a three or four-...
\[16:04\] It's not totally possible today... Occasionally, things like that happen, but I like to think about this as kind of like democratizing access to technology... And yeah, making it equal access is another way that we've described it. So it's not just the big companies that can go after it. It can also be startu...
**Adam Stacoviak:** Yeah. You mentioned Box earlier, versus Dropbox. And we've collaborated with Apple a couple of times, via -- you know, we produce podcasts; they have podcast indexes, and clients, and stuff like that. They do podcasts. And in our collaboration with them, when we had to like exchange large files and ...
**Michael Grinich:** There's a lot of acronyms... It's a world of four-letter acronyms pretty much everywhere you look in the enterprise.
**Adam Stacoviak:** I bet it. Well, yeah, enterprise tends to have that kind of thing, for whatever reason. SSO, single sign-on. Whatever. A bunch of different stuff. But they didn't necessarily lose or win. Dropbox is still around and kicking butt. I use Dropbox every single day. Now, we're not an enterprise, so I did...
**Michael Grinich:** Yeah.
**Adam Stacoviak:** I'm assuming it's probably because they had certain enterprise features. Now, they probably built those features themselves. The issue, I think, and I want to get at though, is this pause that I think you said before, which is like when you're sort of getting to product-market fit, and you're kickin...
**Michael Grinich:** It's a really tough spot to be for companies. You work so hard to get product-market fit, through focusing on the product features and experiences itself - design, the onboarding, the sharing abilities, things like that... Maybe collaboration features, real-timeness... So whatever is kind of the un...
In the case of Dropbox, they eventually did it. Dropbox Enterprise today is an awesome product; it's being used by thousands and thousands of companies. But in the early days, in a moment, and probably when Apple decided to use Box - because these contracts stick around on for a while...