The Co-Founder "Blood Bond" Is a Myth | Michael Grinich, WorkOS

27 May 2026 · 1 h 11 min · 21 chapters

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In short

Michael Grinich (WorkOS) argues that the “blood bond” myth of co-founders is overstated; most multi-cofounder teams end with one person still running the company. He contrasts solo founding vs co-founding through agency, identity, decision-making, and the speed of modern markets. He also explains how he selected the WorkOS idea and why he avoided pivots.

Guest backgrounds

Michael Grinich is a serial founder and the founder of WorkOS (enterprise SaaS infrastructure via APIs). He previously started another company after consulting/engineering work; he also does angel investing and has worked with startups through ODF and a “Solo Founders Program.”

Key claims

Solo founders have no one to blame; mistakes are fully theirs, which can be crushing or liberating. Co-founder partnerships often dissolve faster now. Pivots are traumatic and should be avoided; iterate/kill features instead. Great ideas often look bad to others; success requires being misunderstood long enough to gain momentum.

Notable examples

“Only room for one Zuck at Meta”; “Lion King” as an institution that persists through personnel changes; references to John Carmack, Jensen, Miles Davis, Beatles (John & Paul), and Steve Martin’s creative process. WorkOS’s focus: making SaaS “enterprise ready” and unlocking revenue without changing the core mission.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

The Myth of the Blood Bond

0:00 to 0:45

Explore why the idea of a co-founder bond is often overstated.

“It's not the blood bond that it was made out to be.”

The Solo Founder Experience

0:45 to 2:27

Understand the challenges and benefits of being a solo founder.

Lessons from Previous Startups

2:27 to 8:06

Learn about the journey and insights gained from starting multiple companies.

Navigating Market Challenges as a Founder

8:06 to 9:24

Discuss how current market conditions affect startup growth and founder strategies.

The Complexity of Co-Founder Relationships

9:24 to 12:14

Examine the dynamics of co-founder relationships and their impacts on business.

The Mental Toll of Entrepreneurship

12:14 to 14:00

Explore the psychological effects and isolation faced by solo founders.

The Importance of Community in Solo Founding

14:00 to 14:49

Learn how building a supportive community can prevent founder burnout.

“I always felt like I was actually open to having co-founders on this company.”

Navigating Co-Founder Decisions

15:20 to 17:58

Discussion on the trade-offs between having co-founders and going solo.

“When you were starting this company, you were open to the idea of co-founders, but at the same time, things just progressed and it didn't end up happening.”

Idea Selection and Creative Processes

17:58 to 22:42

Insights into the process of evaluating and selecting startup ideas.

“Could you share more of your thoughts about idea selection and kind of the process there?”

Learning from Failure and Market Insights

22:42 to 28:00

Exploring how failure and market knowledge influence successful startups.

“It's really a transportation market, not the taxi market for Uber.”
Show all 21 chapters

The Journey of WorkOS: From Concept to Business Solution

28:00 to 30:14

Learn about the initial conception of WorkOS and its focus on solving business problems.

“I was like, I don't think I can raise a seed around and survive long enough.”

Pivots vs. Consistency: The Startup Dilemma

30:14 to 33:08

Explore the dangers of pivoting and the importance of a consistent business vision.

“after the first one, the first business I had, which was by and large like a technology cool thing I built in search of a business.”

Identifying Market Pain: A Founder's Perspective

33:08 to 35:38

Understand the significance of market pain and maintaining a firm focus on solving it.

“You know, the iterative, fast improvement, like launching a feature and it doesn't work and having the courage to kill it and move on.”

The Importance of Business Identity and Structure

35:38 to 38:45

Discuss the need for a strong business identity and the implications of changing it.

“It was office there and I walked past the Lion King on Broadway.”

Navigating the Startup Landscape: Trends and Challenges

38:45 to 41:19

Analyze current trends in startups and the rush to find ideas that will gain traction.

“and you should spend as much time as possible up front to try to figure out like, what's the bet you're making?”

The Contrarian Approach: Finding Unique Business Ideas

41:19 to 42:00

Learn the importance of having a distinct belief in your business vision.

“It's kind of become, it's kind of become like a new sort of socially acceptable thing akin to going to grad school or something.”

The Value of Contrarian Ideas

42:00 to 47:58

Explore how contrarian ideas can lead to startup success and why consensus can be a trap.

“I'm curious if you have any thoughts on that or things that you've seen.”

Founder Sales Philosophy

47:58 to 54:00

Discuss the importance of founder involvement in sales and the learning journey involved.

“now I think you have what about 100 people at WordPress?”

Understanding Sales Dynamics

54:00 to 56:00

Learn about the relationship between founders and sales, and the unique value founders bring.

“I mean, it took me like 10 years to get through this.”

The Founder Journey and Sales Teams

56:00 to 1:01:14

Learn about the importance of the right sales team and personal transformation in the founder journey.

“And what I realized later was like him saying that wasn't, uh, that I had the most sales training that I knew the methodologies that I'd be able to hire reps, they'd be able to scale it.”

The Pros and Cons of Solo Founding

1:01:14 to 1:07:38

Explore the challenges and rewards of being a solo founder, including personal growth and development.

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Transcript

Automatic transcript. May contain errors.

0:00It's not the blood bond that it was made out to be. The most common outcome for people who have multiple co-founders is years in, there's always one person still running it. There's only room for one zuck at Meta. We'll stop. The question to ask yourself is like, are you that person or not? Well, I call it the founder pixie dust. The company is like inside of me. I took the company at tens of millions in ARR. What is like the bear case for being a solo founder? There's no one to blame if things don't go well. Every mistake is yours. Follow it up with the case for solo founding. It's a thing people can't take from you if you make it from scratch and it's just yours The company I find is like this mirror It shows you every imperfection in yourself and weakness all the time It's like this adaptive video game on top of your life.

0:40If you only get one life you get one shot Why not swing as hard as you can? Founders usually do things first that happens when it's co-founded companies as well They sort of do the you know the job or the role and they kind of like bring people in who can do it a lot better than them can you share a little bit about what that experience was like with this company yeah i've gone through a whole different journey around this um well so i think the first thing that's like maybe somewhat notable is like this is the second company i've started and so uh the first one i started pretty much right out of school i'd done some consulting and some like random stuff but i didn't i didn't really know how to like operate a business or what a business was yeah um i had studied engineering i had like built a bunch of stuff and product stuff so there's a lot I figured out but for the second company because I had like such a basis around what a company should look like I kind of did the speed run of like the first couple years and like you know the first three months or so and that that actually counts for a lot for WorkOS like this is year eight and so I actually had like many years as like a boot up phase for me to get good at a lot of things and like make a lot of mistakes along the way and kind of like learn trial by fire but the consequences were relatively low like especially during the covid and post-covid era like you just couldn't grow that fast like you know the light speed in the universe was like low yeah and and so that meant that um we were growing well and compared against that you know um we were doing well but but there wasn't this like time sensitivity in the market i think now it's different and i see this with our customers and i see it with um our own business and i do a bunch of small angel investing and I see what these companies is like when things hit they really hit they hit really fast and they immediately start working and so you don't have this like gentle boot up phase where as a new founder you're like okay cool I get to like spend the next 18 months messing around to figure out how to do like engineering management reading all the books talking to people making some mistakes and it's like no you got to figure that out in the next two weeks and the same thing for all these other areas so I think the learning pace in order to do this your learning rate has to be like extremely high it already needs to be really high but i think it's the demands are much higher to like capture it it's like lightning in the jar capture it you know for for my own experience like when i started this company having you know already done the first one i actually wrote down like a list of all the things that i thought were weaknesses of mine i kind of knew what my strengths were and and i and i built the idea of the company around things that i thought were my strengths because you want to put yourself in a position for success you know don't um like had a bunch of ideas for cool stuff I wanted to build where I had like no experience and I was like that's kind of a dice roll why don't I do the one that's like in line with my experience but um I also wanted to make a list of all the weaknesses I had like what were the risks in the areas that I thought could be things that I could either mitigate or learn and I just kind of like went through those and I was like okay what would I do to learn these and and you know pursue them and who would I hire who would I get as mentors and advisors um who should i spend time around who are the the kind of like kings and queens of this domain who are the ones that have written the books you know who are the idols like i know all the engineering idols you know like you know john carmack people like that you know if i met him i probably would like start stuttering over my words because it's like you know it's like nerd you know jesus or something um but i was like who is that for sales who is that for marketing?

4:14Who is it for operations? Who is that for finance? Like, could I put, pick like a killer CFO out of a lineup and say like, that's, this is a person that's like a, because the CFO is really the like business model architect in companies, you know? Um, the answer was no, I didn't know those people. Um, and I didn't really, at my first company, like look up to them that much. It's not that I looked down on them. I was just like, engineering is what wins, make something people want. You know, if you do that, everything takes care of itself which is not true um and so i spent spent time like trying to figure out in these other domains what could i learn and what could i read and um and was it even possible for me to learn these things and i feel like i've kind of gone through this full cycle now of it where even even the first like probably half of the company there were a bunch of these areas where i i actually believed i would not be able to become strong at them I was like that's just not my personality or who I am or the skills I have you know I was like I just kind of was boxed into something already in my own mind um and at some at some point I kind of just like said like screw it I'm just gonna go figure this out um and you actually can learn like just about anything it's like high agency you know kind of takes over but I think the the solo founding journey there's no there's no one to blame if things don't go well there's no one really to like defer to um every mistake is yours you know like anything i get upset or angry about like you can try to blame other people or blame the market or blame whatever but ultimately it's if you accept your own role in it you accept your agency um you're responsible not a bad thing but um so that can either be like extremely crushing we're like the whole way of the world and more it's on you or if you take this like high agency mindset it's actually the most liberating you're like i have full control over my environment like anything that i'm unhappy about i can change um and my attitude is like the first thing you have to you have to start by changing um but i think that's a it's a very challenging like personal development process to go through and if you are going to go through that personal development process at the same time that you're trying to build a product at the same time that you're trying to discover a new market.

6:38You're just stacking these really hard things on top of each other. I think right now it's in particular really hard because the market's moving so quickly to go through your own personal development, plus company development, plus market development, plus just the raw skills you need to learn. In that environment, it might make more sense to team up with people that have skills that are complementary or people that you know. but that's also hard selecting co-founders. The speed at which things go really quickly with companies nowadays if you have co-founders and maybe things are a little bit on edge, you don't have the perfect matchup of people the friction that you would normally have at a company you might be able to get a little bit of progress over a year or something, maybe things blow up much faster.

7:25I feel like we've helped people start companies and collaborate and find potential co-founders over the last seven years at ODF. And I will say that it feels like nowadays people are creating partnerships, but the partnerships are actually dissolving or collapsing much faster sort of when you talk to people who have co-founders than maybe they were, you know, a couple of years ago as well. It's not the blood bond that it was made out to be, you know, initially. I think there is this maybe spoken, maybe unspoken idea that like if you co-found a company with it someone it's like ride or die till the end i don't know um if you look at many of these companies that had you know four co-founders like facebook had four co-founders it's zucks company yeah full stop you know not not to belittle the accomplishments of the other people or to say they're not for sure smart and like i actually almost worked at asana before starting my first startup so i love dustin and think the world of those guys but but it's zucks company you know and it still is very much still is and i think it's very very hard to find like a stable matching of multiple people together over long periods of time for uh for leadership and so the just kind of similar how the default state of most companies is they don't succeed they get acquired you know that's what acquired podcast is called that because they were they were primarily going to study companies that failed you know because that's the acquisition is the most common target the most common outcome for people have multiple co-founders is years in there's always one person still running it and so i think if you're going to start a business the question to ask yourself is like are you that person or not you can have co-founders or not that's that's fine but i think the question should be like is this the thing where i'm going to be the one that holds it forever um because it's a very different perspective building the company in terms of how you make decisions who you hire when you have that long-term perspective when you just internalize that it's your life's work things can happen markets can change maybe you have to sell the company maybe you run out of money maybe a great opportunity comes along and you merge with another business you know but but having the mindset of like this is like part of me you know it's it's almost like the art and the artist you know um i don't think that when people co-found businesses everybody is making that level of commitment to the organization and the idea i think that there needs to be at least one person but generally speaking the other people are like cool this sounds good yeah i'll do it but i could go do something else or like maybe i didn't get a job over here so i decided to co-found the startup with the you know find a vine or something and it doesn't have this like personal like soul bind on it um and so like some people some people also don't want that relationship with their work yeah too i'm not i'm not professing that this is like the way to work i i actually don't think it's like the healthy way to work it's probably not it's it's an obsession type thing yeah it's it takes over your your mind it's like you can't stop like you can't stop thinking about it like it's just i watch these interviews with people like like you know people interview jensen and he says like he's like i work every day i'm working all the time and people are like oh that's crazy that's like you know work-life balance he had all the stuff don't you have kids and all this stuff but like what what he doesn't say or like what's missed in translation is like it doesn't turn you just can't turn it off it's not it'd be like it'd be like going and sitting down with miles davis and being like when you stop thinking about music and he'd be like what are you what are you talking about like it is the person is is the expression and so if if you feel like compelled to have that type of a relationship with your work or you already do in some way i think those people end up becoming founders and that spirit like that fire is like the thing that that drives it forward and you have you have a very different relationship with your work like when when i hang out with other people especially the kind of founder ceo type of people which have made this decision i almost feel like we all have the same mental disorder you know we've all like kind of encapsulated our work in this way but not everyone has it and not not everyone needs it either um and i think also if you have a bunch of co-founders as a group it might not might even be best if everybody doesn't have it if there's like one maybe two people that have it together because if you have two people that have it and they get at odds it together it explodes and blows up you know there's there's only room for one zuck at meta like full stop you know um and so it's it's kind of this introspection thing about like how you want to work and what you're what you want your life to be like going the solo route like solo co-founding um you know removes like potentially some risk around like co-founder breakups and explosion but it also like applies a lot of other challenges around it um around like you know community and like having someone to bounce ideas off of and like friendships and relationships and like you know the the bond between people that are spending like so much time creating creating something together is like so deep it's like deeper than like most other things that people have in their life that um i have felt the that like pang of jealousy of seeing other people have that when even i know it's probably more of a um uh like an imagined fantasy of what it's like versus what it actually is um you know desiring the type of relationship with someone you know like uh like john and paul had from the beatles you know writing music together like that kind thing it's just like oh yeah it's like juicy um but they also yell at each other all the time it's crazy right like the the amount of beauty they were able to create together but also for a very short period of time relative to a lot of bands totally there's a lot of examples of this where people make really good stuff together and then also like don't get along well together you know you kind of imagine as like they're best friends forever but um having like the best working relationships aren't one that lead to that and if you're if you're in your like you know early 20s you just got out of school you got out or this like college this environment where you're meeting all these new people and everyone's at similar life phase and it's really easy to make friends you go to parties and talk to people and stuff and you get dropped in the workforce suddenly you have none of that it's like hard to meet people everybody's busy dating's terrible you know like it's you don't know who you are and you apply on top of that this like machine of isolation which is the company starting thing it can like mess with your psyche it can like really screw you and i think one of the things that y combinator is fantastic is creating that community element what you guys are doing and others to create that like kind of um you know substrate of like connection uh because without that like people will frequently burn out you know there's only so much you can get you can get online um but i think it is just a really hard thing.

14:21I always felt like I was actually open to having co-founders on this company. I just ended up getting started so fast, actually. As soon as I had the idea, I raised money and hired people and it just started snowballing very quickly. I didn't have anyone waiting in the wings that was ready to jump in and do it. Timing is such a hard thing as well for it. If you're enjoying this conversation, then perhaps you're starting your own company. And if so, you should apply for the Solo Founders Program. I've spent the last seven years working with startups and founders who are figuring things out. And I'll tell you, the ones that make the most progress are the ones who make sure that they have relationships that can help them go the distance.

15:01The Solo Founders Program is about bringing 10 solo founders together so that they can build solo together versus building solo alone. I'll work with you, who will invest$100 ,000, and will make sure that you make the most progress that you possibly can in three months. If that sounds interesting, you should learn more and apply it at solofounders.com slash program. When you were starting this company, you were open to the idea of co-founders, but at the same time, things just progressed and it didn't end up happening. Did you realize sort of the trade-off that you're making is obviously there's benefits to having co-founders if it works and there's benefits to being solo.

15:40But were you thinking about that at the time or was it just things were moving so fast and it just kind of happened? I think so. I was less concerned about it being a liability for the company because this business was something I knew I could execute on, or the first few years of it. I know how to write software, I know how software engineering works, at least enough to make this thing. I knew how to hire engineers, what a good team would look like. I knew how to build things for developers and APIs. Selling software APIs to developers is kind of like, if you're in the community, it's sort of like selling to your friends.

16:19I kind of knew who all the companies would be that I'd go spend time with and could get plugged into that. I think if I had been building a very different product that had other constraints around it, I absolutely would have stopped and not driven the company before finding co-friends. As an example, if I had started anything related to hardware engineering, I think that would be super fun to work on. I'm very interested in that. But I haven't built, I've toured some factories and haven't built anything. That would be a big risk factor on that. If I was building a product, at one point I thought about starting a software company for electronic medical records.

17:03It was like a stuff around the Obama era and modernization. And I just seen, I was like, this is a software problem that could be fixed. But that would require having all these relationships and doing sales with hospitals and partnerships and a whole medical system. That would be a thing that I would probably get a co-founder on, you know, to do it. Where there would be a good, like, parity of skills and experience and depth. But for this one, I was like, am I just going to get, like, another person to write code with me? Like, yeah, I mean, that's great. But there's not this, like, enormous skill gap.

17:36and it was one of the things that led me to thinking I could get the company started quickly as well. I was like, of all the ideas I have of things to work on, which one has the highest chance of working out because the market is great and aligns with my skill set really well. So I kind of selected the problem in a way first and then I think not having a co-founder kind of came out of that. Could you share more of your thoughts about idea selection and kind of the process there? I think that either I read or somebody told me that you had a way of taking notes on various ideas and exploring different things.

18:11I'd be really curious to hear more about that. I spent a year and a half, something like that, a year and change, trying to think about what to do next. I wasn't even convinced I was going to start another company. I was a pretty wide open mindset. but I had read a few different books about like creative process. You know, there's a really good one called Born Standing Up by Steve Martin. And then there's other stuff that, you know, like Jerry Seinfeld and people in comedy, it's like extremely creative act, you know, talk about where you think like a joke is something that just like pops in their head isn't immediately good, but it's like not the case.

18:52Like most of what you produce is like bad, it's garbage. and then the selection of the good stuff is what makes it into the act you see you know and also when they go to the when they go to the comedy clubs they're trying out the material i don't know if you've seen this before but i've gone to comedy clubs in new york city or whatever and you see these famous comedians they just pop in and they yeah they're just like okay that one didn't work and they're like they write a little note on their phone or whatever they're looking at their notebook yeah i mean they're trying stuff you know on to the next one yeah yeah they bomb hard and you know if you've ever been to the comedy cellar in New York which is a great spot they frequently will have these people that just show up you know like it's just like NZ's and sorry you know is there like Chappelle or something and they're not on the lineup because they don't want like a big audience and they'll try new stuff anyway so all this is to say I think having good ideas is actually really hard like in hindsight when something works it seems obvious or everyone thinks it's great but to actually come up with it is very very challenging and so I kind of looked at all this and I was like what would be like a process that I could give myself to try to like get good ideas you know to make sure because after doing the first company I was like it's so hard it's so hard like I only want to do that again if I'm pretty sure it's going to work you know like fool me once you know I'm not going to do it again unless I'm I'm pretty confident it's a good company to bet on and so one of the things that that people talk about is just having a lot of ideas write a lot of jokes see Martin like just wake up and write jokes all day sit down at 9 a.m and just work on it just work work work don't wait for inspiration to strike just like think um and so i tried to do that and and did a bunch of i did a bunch of consulting stuff like small projects we kind of felt like a grease to the machine um but i was just trying to think of new stuff all the time and i wouldn't filter it by what i thought was a good business or a good just like stuff i was interested in like i was curious about so i just like notebook i just carried it on the back of my pocket i still have it somewhere it's just like ripped to shreds because it's all beat up.

20:47And tried to write down things I thought I was curious about, things that were changing the world, things that just kept coming back into my head. And I put more or less an idea on every page. And so I'd write two sentences and the rest of the page would be blank. But I would come back to it if I had more ideas and more pieces of it. And so you could kind of see the ones where there was accumulation of additional ideas or concepts. So that was kind of the raw synthesis of the problem space. after that I tried to think about areas where I had unique experiences because just sitting around and like trying to come up with ideas like if we just sit with a whiteboard and just like you know burn tokens and come up with stuff you're at best you're going to come up with what also a bunch of people you know at you know like Stanford Business School are coming up with or some YC kids trying to pivot their startup or some executives at Databricks or whatever.

21:50You have no unique information. You're just going to spin on the same level. So you might come up with something, but the only place you have an advantage is something where it's some personal experience of yours. And so I tried to also think about what were places where I had seen things that I knew to be true that the market didn't realize yet in that way. and the best teacher of that usually is failure because usually if you failed at something it's because you thought it was going to work and nobody told you it wasn't going to work certainly people gave you money to try to make it work if they invested money and it didn't work failure is a much much better source of information than success and so I tried to think about things I had struggled with or failed there were bits around the company experience I had had that were really actually really hard that i thought wouldn't be that hard um so that was the other you know unique information um the third was uh i tried to find like enormous markets and so something i had sort of sort of learned the hard way is you like can't outrun a small tam like if you sell into a market that's expanding it's like changing that's possible to do like nobody thought uber would be this big but transportation's an enormous industry right But people are like, taxi?

23:09It's really a transportation market, not the taxi market for Uber. But if you pigeonhole yourself too much and you don't see how the market is going to grow, you can win the whole thing, but then you're playing small games, win small prizes. I was like, it has to be an enormous market that feels ripe for disruption in some way. It hasn't like a copycat company, but an area that hasn't been touched. And then lastly, fourth, it has to be something that fits my skills. so not just an observation i had but um you know a thing where i felt like i have the ability to quickly execute on this so i don't have to go like learn from scratch you know i had a bunch of ideas for building like an electric airplane i think it's still a cool idea i was like i'm gonna have to go like get my phd in aerospace on an accelerated basis maybe not the degree but learn all this stuff you know very fast um you can do that like elon did that it's a famous story getting this like yeah Blake Schultz is like stack of books but I was a little bit impatient I was like I want the second one I do to work yeah I want it to work and so de-risk across all of these and for me I kind of picked like the IT sector I was like IT I don't even know what that means it's like just seems gross and old and hasn't had this like Stripe moment you know like fintech kind of seemed boring before Stripe I had built things for developers I knew software I knew infrastructure and I'd seen this problem around this like enterprise stuff at my first startup.

24:33I hadn't solved it but I had stumbled over it. I'd tripped over it because it wasn't an obvious problem to the market and so I was like that together you know feels like it's it's good fodder for ideas and so that's the one I picked to work on. It's sad you can't pick multiple things you can't run bets in parallel because I always wonder what my life would be like if I had started one of the other you know half dozen or so contenders running for it um but i'm very happy with where i landed obviously on this and i'm i'm glad it's a it's a thriving company behind it too so you've got the you've got this notebook just to take it back to sort of that time you've got this notebook you're coming back to different pages where you're sort of filling new things and you're seeing what pages you keep returning to was it clear that at some point you were returning to sort of these these ideas that were more related to IT and enterprise ready and that sort of thing?

25:26Or were you also returning to these pages that, you know, were really interesting, but maybe you just weren't, you sort of talked about that last category of evaluation, which is like, is it a good fit for me as a person with my skills? Was that sort of the deciding factor there? You were coming back to these two types of pages, but then you said, okay, honestly, I really want this thing to work. So I should go work on the one that I have probably the best sort of personal fit with. Yeah, I would say so. That was kind of the filtering aspect towards the end. There was an element of what can I practically do quite quickly on this.

26:02To build an airplane takes many years. I mean, what Blake has done with Boom is incredible. It took them, I don't even know how many years before they flew a jet. A long time. A long, long, long time. And it's just the proto-jet. It's not like the commercial jet. and so um i just felt this like urgency i was like i want to get back after it and so software's like fast to build and easy to explore but many of the other things i kept gravitating towards that i thought were like bigger problems in the world like um you know like an idea i couldn't figure out how to build a company around it but i had this idea to try to build like de-radicalizing technology so if you remember back this is like back in 2017 or something 2018 there was like the YouTube spiral where like if you just people would just watch something and get completely completely rabbit hold and like radicalized based off yeah it's like the autoplay like the algorithm would like you know you'd start off watching like a kid's you know tv show and then like eight you know autoplay videos later you're watching some like ISIS this would happen for kids too totally yeah and in particular it was like people that were susceptible to it were folks that were like living in areas where they didn't have exposure to other things you know and they're impressionable they're young you know um like teenagers and stuff and so i was like what if we like built technology i did the opposite that got people instead of radicalized like kind of you know like conscious in the world and we did through media couldn't figure out how to build a company i think it's cool i think youtube actually they fixed it fixed a bunch of stuff about the algorithm here you know had an idea for building like a software stack for cars it's like it's crazy that cars are still dumb like you can buy a hundred thousand dollar tesla but i can't make my Toyota from 20 years ago smarter in some way I had a whole bunch of different things that I built as ideas that I thought through I would pitch them to people and I'd talk about them I'd work the material but getting down to it many of them conceptually I was more interested in I think the initial conception of WorkOS helping you make your SaaS enterprise ready it's probably a lot of people we weren't able to hire because they didn't think it was that exciting to work on you know it's like it's infrastructure that everybody needs but nobody really wants to do it's not the hot shiny thing you know i had another idea of a company to build that was an ai infrastructure company this is back in deep learning and tracking hyper parameters and like you know artifacts and everybody's like training these models on like their laptop and then like uploading the kernel to like some server to run it's like software the supply chain management for this was like terrible i was like oh i could just build a github for ai training but I thought the timing around that in the market was going to be too long.

28:47I was like, I don't think I can raise a seed around and survive long enough. I won't be able to get customers. This is a cottage industry of people doing this in-house. There was this pretty strict filtering around the practicalities of can I make this into a business pretty much within 12 months. You can extend it to maybe 16 to 18 months but you got to show something working within about a year of getting it going. Otherwise, you can't get investors to care about it anymore you fall off the map practically speaking also your team gets antsy and anxious and they're like what are we doing here you know and so i was like what's the thing that the timing feels right i feel like i can build it i feel like uh the risk profile is low it fits my skills i can sell it you know if not making a ton of money i can get users in it not going to fly the electric airplane you know in 12 months um but i can probably build this like off security thing and it meant that the act of forming the company and then this like second act of starting the process was actually more of a pursuit and expression of like creating an amazing business rather than like it's just a technology exploration like to me work with like the the thing i'm kind of the most proud of is as a company is actually not that technology of amazing technology is that the formation of it is a business solution to companies we help you grow We help you like unlock revenue.

30:07Like we do it through technology, through APIs, but like the business impact we make is so clear to companies. And that was a thing I was like really hungry to find and create after the first one, the first business I had, which was by and large like a technology cool thing I built in search of a business. If you do that, if you start like just a product and engineering thing and then you're searching for the business later, the best case is you get lucky and you slap something on. you add ads or something like that to it or you stumble into some network but you never really create this harmony between the product and the business model and I think if you build it from the beginning with that mindset you can actually integrate the two together so you get this yin yang type of thing together and it feels really good and that was a design principle I had as well I was like how can I like when I was saying about the anti-radicalization stuff it's really valuable for the world but it's not like a postdoc I'm doing.

31:03It's like a non-profit. It's like, I want to make this thing an economic machine. Those gears have to be machined to be perfectly fit together. I spent a lot of time thinking about that. It could be a fit. This is the one that stood out. It feels like there's this giant romantization of pivots in startups. In tech, we really love the pivot as an industry. But at the same time, I feel like a lot of great companies don't pivot. You hear about the great stories of companies that do, but WorkOS, you pretty much had the same description from the beginning as you do now. It's been pretty consistent, right?

31:48Sort of this high-level thing. And it sort of just works. And it feels like, in some ways, because the pivot is such a popular thing to talk about, it kind of feels like perhaps people rush into whatever it is they start working on instead of taking the time to maybe spend the thoughtful process that you did to come up with what you should actually be working on do you think that there's anything to that or like maybe reject reject the premise that I'm laying out there I'm curious what your take is on it because it seems like there was an awful like lot of thoughtfulness on your end to actually get something where you felt like, and I think that you just said this a little bit where you were talking about this idea of it wasn't like we were trying to slap on a business model after the fact, it was that we were really, I was trying to figure something out that had a real business problem that I was focused on first and foremost.

32:39And if I could actually build this and get it out there, which you would have a high degree of confidence in your ability to do, it would actually help these businesses, you know, achieve much more revenue and be much more successful. I think pivots are the most traumatic thing possible to do to a business. I don't, if people romanticize them, they should not. You know, iterating on things and learning for the market and like evolving and trying different things and learning from your mistakes. And like that's a different thing. You know, the iterative, fast improvement, like launching a feature and it doesn't work and having the courage to kill it and move on.

33:17Like that I really admire. but changing what you're about and like why you exist on a whim to me like indicates some type of like lack of integrity on why you exist and and I think it's very hard after you do that for your team or your customers or your investors to like know who you are like what it's about you know you you become you become more a child of the process than actually like the output of what you're trying to do and so i had no interest in pivoting i i had no i had no like romantic romanticizing about like the startup process i was like i'm gonna enter into this like suffering like many years of like suffering and hell it probably won't work out and the last thing i want to do is put myself in the meat grinder as many times i can um i think people should try to avoid pivoting at all costs.

34:16There's this document that I found. I tweeted this a while ago and it was this one pager I wrote about a year after starting the company and I was sending it to early customers and folks and you literally could use it today. It's literally the exact same thing. I think I've spent a lot of time reflecting on why that happened. Some element of it, I think I did get lucky quite a bit. But I think the main thing is I focused on like the pain in the market not my technology like what was it doing for people like who cares who cares about what you're building um i think it's one of the questions in the yc application is like who cares about this and i find myself asking that all the time about ideas or new things and it it doesn't mean that like a lot of people have to care like not at all like the the initial market for work os was like my friends working on other sass startups.

35:12It was like people I know. But the who cares? I almost felt like it was this mission where I needed to go fix this problem because I had tripped over it so hard. And I was like, they're all going to hit it going 200 miles an hour. It's like a big road bump, you know, that I needed to go file down or a pothole or something. And so like picking that and then staying firm about that, but then being flexible and how you go about doing it. And like flexible in the means of what you do uh i see sometimes people do the opposite where they're like um they they like the technology they're working on um so they're adamant about the technology that they're building but then they're very flexible at how it gets applied yeah they're like we might do this or this or this or this we don't know where we can the customer might be yeah they're like we built this thing the first person didn't like it so let's go and try find some other people who might we're building agent orchestration framework, you know, and we're going to go find 12 different markets to figure out where to apply it.

36:10Sometimes it happens. AI might be the one place that AI actually is possible, but like historically in business that has not worked well because you find one dimension and then you find another and you find a third and it starts working and all three are so different. And the question is like, who are you? What's your identity? Who are you as a business? What matters who do you help like why should you exist as a company like what is the myth of the organization that transcends each individual person working there that's this like shared hallucination of the group of people together what is the thing that like outlasts you know each individual person working there um i love institutions this idea of we create things that like go on past each individual person it's like the ship of theseus you know uh you know i was i I was in New York last week.

36:57It was office there and I walked past the Lion King on Broadway. I don't know if you've ever seen it. No, but it's crazy. It's incredible. And it's been around for what, 20 years now? I think more. And they do like 10 shows a week or something and it's a machine. And if people get sick or people have kids or people are born and they die and they go, like the Lion King keeps going. It's gone through different owners. It's gone through different managers. It's the same story. It's an institution that just, its entire purpose is to keep producing the thing that is the Lion King. You know, you can't make that if you change who you are on a whim.

37:31And if you signal that you're able to, you know, that you're willing to do that to your customers. And I think it's even a thing that like your customers look for is when they're sussing out, they're like, are you going to go to the ends of the earth on this for me or not? and if they see you changing who you are for like different types of customers kind of being this chameleon it's hard to believe that that person is like going to be down to you like i i feel like our relationship with that we have with our customers today is one of much more like a partner you know it's much more like i work there at the business a part of me works there and like you know i will be this like durable supplier over long periods of time um you know It's like you're a restaurant and I'm your bread guy.

38:15And I'm going to bring you bread every night of the week at the same time. Because if you don't have bread, your guests freak out. And you just don't have to think about that. But if I start making pizza on the side and then selling croissants on Saturday mornings to someone else, and people are like, oh, is my bread going to show up on time or not from this guy? So I think pivoting is this thing that puts that into question. And people do it. Great companies have done it. but I think it should be an absolute last resort and you should spend as much time as possible up front to try to figure out like, what's the bet you're making?

38:51Like why you should exist? And if that bet is invalidated, you should just kind of like run the algorithm again. You know, it's like form a band, put it on an album. If none of you like the music you made together and it wasn't a very good band, that's fine. Just go start a different band. You know, you look at these like bands that are like super successful and you look at what the people did before and they have this long string of like there were a bunch of bands that all kind of sucked you know like in different ways you know but you learn you try different things you find different people you know it's it's like any anything or like relationships like you know people that are happily married that is after a long string of unhappy relationships you know or like relationships that ended in unhappiness in some form so you kind of only have to be right once and i think when people pivot what you're robbing yourself is the opportunity to actually find the formation that where you'll get it really right again you're holding on to a thing that like didn't quite work and really what you should do is just like recycle it again and it's it's one of the downsides of being able to raise so much capital is it's like kind of inconvenient to do you're like oh we raised seven million dollar seed round incredible you know and like 18 months in nothing's really working what do we do the core thesis we're building doesn't work and now we're a bunch of random people trying to find the new thing that's a really hard position to be in i I really don't envy that.

40:11And I think there should be some maybe better socially accepted mechanic to just run the experiment again. Form a different team, recycle the capital, go into it, and maybe some VC can come up with that structure. That would be really interesting. I think it would work really well if there was a reset button that you could hit if you raised one of these big funds. And maybe it's the same cap structure or something like that, but the team can be slightly different or you can run a different bet. Instead, I see these examples of teams like pivot, pivot, pivot, pivot, pivot. And then it's like, who are you?

40:45It feels a bit like there's a sense, especially now, maybe you can feel it or you see it when you talk to other founders, but it feels like there's a sense that time is of the most important essence now, more than ever before, because of the speed at which things are progressing. And I feel like it's causing people to rush into things maybe more than ever before. And maybe that's also combined with the fact that startups are, and AI is in some ways, like it's cooler than ever before to start a startup. Or it's more, maybe it's actually more socially acceptable than it is cooler. It's kind of become, it's kind of become like a new sort of socially acceptable thing akin to going to grad school or something.

41:25I don't know. I'm curious how you think about how if if if there's some truth to that and also how that relates to people kind of maybe trying to come up with ideas or businesses that a lot of people agree with in the early days. Because it seems like a lot of the best companies, they generally have a lot of people who don't believe in them, who disagree with the idea, like the founder or founders might have a really strong opinion about things that turns out to be true, you know, in months or in years. but a lot of people just don't get it early on. But it feels like a lot of people are trying to start things that a lot of people get in theory, and it maybe leads to more generic companies, maybe leads to more companies that are kind of not actually based off of the individual's personal experiences, but they're just trying to do this almost, maybe it's like overfitting.

42:16I'm curious if you have any thoughts on that or things that you've seen. You know, there's that famous question like Peter Thiel would ask people, like what's one thing you believe that others do not? It's kind of a party trick question you ask. I actually think there's some truth to asking that question around the company. What's the thing that you believe that other people do not? And if you're like, well, what we believe is we need to build a context layer for companies to have information about their internal business process. It's like, other people believe that too, man. You're not exactly on the contrarian angle on that.

42:52And it doesn't mean that's a bad thing to exist. Like, I think it doesn't mean like you're a moron for coming up with that. In fact, like realizing that, like you're probably even ahead of the rest of the world. You know, that thing doesn't exist in general, in general in the world. So you can go buy that. So it doesn't need to exist. It will exist. But if an idea is too consensus, there will not be enough of an advantage building around it to build a company. You won't be able to get enough of a head start. When you're a tiny startup, you've got nothing. You can move fast, but you don't have a weight.

43:30There's no inertia. And so you need to find a place where you can be misunderstood for long enough that you can gain enough momentum that when everybody else wakes up and sees it, you already are outpacing them. And if something is too consensus, you can't do that. Because some exec at Databricks will figure out that this is a good thing to build and they'll be able to convince their senior management to put a team on it and they'll go build it and then they'll launch it. And even if it sucks, they'll own the mind share because they have the market. And so you need to have an idea that people like that will try to pitch and it'll get shot down.

44:03Or everyone will think it's a bad idea. And so there's actually this thing around like everybody wishes fundraising would be easier. You know, like I talked to 30 or 40 people and I only got like two term sheets, which is excellent by the way. Most companies get zero. And you know the second most common is one. So you get two term sheets are already in like upper deso. But thinking like, oh, I just did this big fundraising process and I only got, everybody said no, is actually a prerequisite for success. But the thing that's challenging is it's very close to also having a bad idea. Good ideas always, the greatest, the best ideas always look like bad ideas.

44:43But also all bad ideas look like bad ideas, almost. Occasionally there's bad ideas that look like good ideas. But usually people can discern that they're not good. So I think you actually do need some amount of contrarian pressure in the market. It's also a founder filter. If what gets you excited about building the startup is that everyone's going to think what you're working on is cool, and you're searching for validation from other people, which I understand deeply. I seek it from others. I did in school, from my family, from my friends. you know um if you need that uh and you're and you're filtering your ideas based on it you're you're only going to pluck out the ones that have the highest likelihood of everybody liking it which won't have any advantage of the market and and so it works against you uh in that way which is which i think is this like i don't know a very very like painful element of the mechanic of the startup you have to like almost by definition if you're going to work on something that is going to be successful you have to survive being misunderstood for a long period of time and that just sucks it's like you'll you'll present what you're working on to your friends to your relatives to people you're trying to date and they'll just be like what the hell is this guy doing like he's wasting his time and like again the thing is like it's very it's very simple you might actually be very close to yeah it actually might be a total waste of time too you don't know you don't know right but but it's a prerequisite and so i think like working on something that's too consensus actually you will guarantee failure because you can't can't make it you know you'll you can maybe raise 10 million dollars and squeeze a million dollars in air out of it but it's not going to be enough to like uniquely stand the test of time and and accelerate um and it's it's kind of a leap of faith bet at some point.

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46:35I think that's why if you go back to like, what is the thing that I understand? Like, this is a bad idea, but I uniquely know it's a good idea. I know a secret about the market that nobody else knows. And I'm going to like hook my idea on that because it's some lived, learned experience that I have. If you don't have that, like you're just swimming around trying to find something. And I think that's, honestly, I think it's just a waste of time. is statistically so unlikely that you'll land on the thing yeah so so there is there is a lot of truth in that like the best ideas look like bad ideas um initially and i think if you go out and fundraise this is kind of a maybe crazy thing to say like if you go out and fundraise and you pitch 10 vcs and you get like six term sheets you should reconsider the idea you're building yeah still raise the money get all the money you know get it in the bank but you should immediately come back and be like guys i think this is the wrong idea to work on now that we have all this funding we need to find something that's our unique angle that everybody else wouldn't do and bet on that because otherwise you're just gonna be another kind of like yet another whatever company so when you're starting out you're solo you this is your second company so you um have the advantage of being able to speed run a lot of things that maybe took some time to learn the first time you're starting out solo you eventually build a team now I think you have what about 100 people at WordPress?

48:01Yeah a bit more, almost 120 right at Dunbar's number, it's interesting so you've got this team now I think that in many ways people maybe think that they should be working on what they're best at or they have different ideas around what they should be doing as the CEO as the founder, as the company grows I would love to hear your philosophy, especially around founder sales. When you started to bring out other people, when things started to break with you doing it on your own, that sort of thing. Because I think that oftentimes founders maybe think that they should be getting external sales help, maybe prematurely.

48:43And I'd love to hear your thoughts on that and what your experiences have been. my journey around founder sales like has a few different kind of chapters and phases i think the first one which is just like worth calling out is i deeply believe that i could not become good at it which if i say that with it sounds sounds you know nonsensical um but i actually really believed it i i think i had been told that a lot in school if you're like a cs grad you know the the canonical like nerdy engineer builder you always hire the sales guy and the person comes in and they whip the company into shape you know and you know fire the ceo or whatever and and make it into a real business it's like this trope you know in a lot of cases it's true to be clear um but i i internalized it to the point where it became my reality not someone else's story but it became my story with no with no data around it you know um and i had investors kind of like hint at it or me that and other people in the market.

49:48And the reality is like everything can be learned. You just have to choose to learn it. And so for the first chapter of my kind of sales journey is like I was choosing not to learn this. I was like assuming I wouldn't be able to be good at it. I could never be good at it. So I just didn't pursue it. And I would try to hire other people to come do it for me. But stumble through it a little bit. But really be like I'm stumbling because I suck at this and I'll always suck at this. And so I'm going to hire experts. And the problem with that is there's this incredible thing about doing sales, which is not the mechanized scale it out sales motion.

50:21I'm not talking about that. There's this incredible thing that like sales is the ultimate distillation of like the company value to the market. It's the ultimate performance. It's like writing your jokes and performing them on stage. And if you just wrote jokes and you didn't go perform them, you miss out on the whole thing. You know, it's like you don't realize what you're missing out on without doing that. It's like reading about sex or something. Be like, okay, I got it. It's so different than actually what the reality is. And I think for so many founders, you're robbing yourself of the opportunity to become really good at it and drive forward your company.

51:03And just that it's part of the entrepreneurial experience to become great at this. What other job do you get to learn how to do this? Never. You're never going to go get a sales development job at some other company, probably, or whatever, if you're a builder. It's like the one job where you're going to be able to figure this out. So it's an opportunity to become amazing at it, even passable. And I think it's also essential because it's the ultimate expression of the value of the company. And if you love your customers, which you shouldn't start a company in a dimension unless you love your customers, but if you really, really love them, if you're like, I want to build software for doctors because my family had doctors and I just want to spend time around them.

51:41and I love medical profession, you're going to love doing sales with doctors. You're going to spend all this time around learning about their business. Sales is mostly about asking questions like curiosity, understanding their business. The best form of sales is where you understand their problem so well that you can wrap your product around what they're trying to achieve and achieve their goals. They don't feel like they're being sold to. They feel like you're solving their problem and helping them be more successful. This is an amazing connection you get with them in the market. And I think that's not how sales is framed.

52:11That's not how most people have bought stuff. It's not the experience engineers have when we go buy software. There's so many lousy sales experiences in the world. I mean, literally starting with if you ever like bought a car or something, like major purchase, it's terrible. It's terrible. But I think if you reject that premise and you're like, I'm going to create excellence in this, in the same way I have excellence in all these other areas of the business that I care about, you can become good at it. And it's kind of like that harmony I was saying that, like yin-yang between the two, where if you just decide to do it and read all the books and learn it, you can bring that same creative energy to it.

52:50It also is more mechanized than people understand. They kind of think about salespeople as steak dinner and golf game and wear a suit and be like alpha male. And I got a Rolex and I drive a Porsche and slick my hair back. And that's how sales. It's not at all the case. Certainly not with technical products. We sell to other nerds, super smart technical people that really your stuff has got to be amazing for. It's fun. It's actually one of the things in my job now I like the most, which is crazy to say. Because I get to spend time. You will pry it from my cold dead hands doing this. We just hired our head of sales a couple months ago.

53:27And he's fantastic. And I'm really excited to collaborate with him. But in the process, someone had said, is Michael going to give up doing sales? And I was like, never. Never. Because I want to be close to our customer. I want to do stuff. What we're doing now is building a sales team and an engine around it to scale it. And we need to train and hire a bunch of different reps and go get so many new companies getting started that we could help today. I can't do all of it. But just to contextualize for people who are watching or listening, this is the first time you had a head of sales at the company?

53:58Yeah. So I had hired other, this is the first time I hired a head of sales fully in the the kind of like uh high agency like i'm doing this but i'm going to partner with you to scale it versus i'm hiring this person because i'm going to hand it off yeah that was the previous mindset i had i've gotten it to this point ah i suck at doing this um i shouldn't be doing it yeah my board doesn't like me doing it you know all this stuff and so i'm going to go hire a sales guy i did that a couple times i hired people in with that mindset the problem is people can smell it yeah the people that are coming into that opportunity they're like oh i can come in and get the power i can come in and own this whole thing and i can tell you know the founder that now i own sales and it's like this ego trip and all this stuff the right person you want to come in that's wants they should be really curious about how you've been doing this stuff it should be a collaboration between the two of you it should be like you know like you ride shotgun with each other into these these experiences and like find new products and new ways to grow in the market and then their job is to exclusively run that as your job is to go run a bunch of other things in the company.

55:03But this was a huge journey for me. I mean, it took me like 10 years to get through this. And I remember having this conversation with one of our investors who I love dearly. And I talked to them about this. This is several years ago. And I was like, there's this person we're going to hire as a head of sales. And look, this person's got the amazing track record. And they got everything I'm looking for. You know, they got an MBA. And then they also have a CS degree. And they worked at Amazon. But they also worked at a startup. And like AWS and also a startup. And I was like, this is the profile.

55:34I was like, we should, this is, this is the guy. And this one investor was like, I understand you're excited about the person and we'll close them and we'll get them to hire. But the reason that we invested in you is like, we think you will be able to do sales better than anybody else you will ever hire inside the company. And I remember thinking to myself, that's ludicrous. No effing way. No way. This guy's like off his rocker, you know, no way. Look, I like, how can I be the one? It was, it just didn't register in my mind. And what I realized later was like him saying that wasn't, uh, that I had the most sales training that I knew the methodologies that I'd be able to hire reps, they'd be able to scale it.

56:12None of those things. He was just saying you and buying the product, you'd be able to go out and do that at the market. The special, I call it the founder pixie dust. Like the things that I can do in a sales, cause it's going back to what we're saying earlier, the company is like inside of me, you know, I can do these things that like I'll never be able to do. I'll never be able to expect anybody else to do. And you know, I, I, I took the company at tens of millions in ARR with, with that. Um, and I think it turned it into something that I was like, how do I avoid this? Or how do I build my founder job in a way I don't have to do this thing?

56:43It's kind of icky. And like, uh, I don't like salespeople and like, uh, bringing them in the company that culturally mess everything up, you know? And like a lot of companies, you reach the phase you start having to hire sales people and you're like great now it's the end the end is near we have to hire these jabronis in you know there's a bunch of clowns aren't that smart and i was just like screw that i'm gonna find sales people that are really smart they're hard to hire they're hard to find they're expensive it's great sales people make a boatload of money you would not believe how like the really really great sales people how much money they can make but they're worth it right they drive value they literally drive economic value for the company you can look at it and be like i'm paying them this much but they're bringing in that much okay you know i'll do 3x that deal you know on both sides um so very very hard to find but i just i just said like if i'm going to actually continue doing this for my own sanity i want a sales team that i'm like thrilled to work with people when i wake up in the morning it's like the first person i want to call you know where i'm ecstatic to get on a call with them and i'm going to learn a ton from them around how to scale it and if you just take that mindset and you're like that's the sales team I want then it becomes this thing from like running away or like shying away to like holding on to and being really active I think that's that's kind of the culmination of like my own journey in doing sales and I would I would I would encourage anybody that's like feels like they're on the other side of that where they don't think it's possible it's probably the case that you just haven't met any great sales people that that was the experience I had it's it's not that it's not that I had met like bad sales people but like I mean it's just kind of generally with people with friendships you know you meet people and like you get to know you have friends that are just like so so friends but then occasionally you meet people where you connect with them and you're just like holy shit like I'm just totally on the wavelength with that person we are going to be friends for the next 20 years like you need to hold out to like find those people and then believe that they exist in the world and and I think those exist in all the different domains even if you're kind of like afraid and scared of them.

58:43And so part of it is like put yourself in the position to meet them and succeed. Go pay an exec recruiter to introduce you to a ton of people. I went and interviewed all these like CROs just to find ones that I liked. And there was like two or three of them that I was like, okay, those guys are actually smart. These guys are like not clowns. Like I remember one in particular as a digression. It's this guy named Chris Merritt who is leading sales at Cloudflare. Chris is total brainiac. He's like total engineer mindset. I remember talking with him. I talked to him for like an hour and I had to go for a walk after I hung up the zoom call.

59:17It's like during the pandemic. Cause I was like, what did I do? Who did I just meet? Is this like a, he led sales? He doesn't seem like a sales guy, but totally. It's like totally mechanized, you know, and how he thinks about growing it. It's just really, really smart, very cerebral. Um, and so you just need to look for that in people. And, and sales is a very, very important function of the company. If you lean away from it, if you don't, lean into it to try to make it amazing, you're screwed. Because it's the economic value capture piece of it. It's like, in some ways, one of the most important parts of the whole company.

59:49But I think for everyone going on their own journey, depending on where they are in that process, it's important to know that you can learn it. And that if you haven't been wowed by somebody yet around that, you should make it your personal goal to get wowed. Find the person. It doesn't mean you'll be able to hire that person. Chris, love in pieces he wasn't going to take our head of sales job at our little you know dinky you know probably at the time i met him we were like 30 40 people i was like i think i emailed him even i was like chris would you like he's like i might advise here's my phone number you can call me but like i've just been like cro of a global public company probably not going to join um shoot your shot you know um but at least meeting those people i was like okay i know it's out there i know i can fall in love i know that the people that are there that i can resonate with i just need to like structure now from a process how i can line that up and get that into my company at some point and then just be patient you know and and wait for it to hit but yeah but you know turning it's one of the crazy things about doing startups in this like founder journey is like if i would have told you this like five years ago or six years ago i'd be like a totally different person it's crazy like i just i feel like i've turned over my brain in that way and like i wonder what the version of that is for me like five years from now like where's where's my you know brain evolving it's it's why it's fun it's why it stays interesting and why i continue to surprise myself in it as well okay so last question this is this has been amazing thank you so much for doing it um uh so many people are gonna have so much that they can take away from this um last question is it's sort of a two-parter i think that i would love for you to share sort of what you think is like the bear case for being a solo founder and then follow it up with the case for solo founding yeah I think the bear case um is that you miss out you miss out on you know finding your john lennon like if you're adamant around it you're like okay I get to own more of the company or I get to make all the decisions or I get to not have a you know someone I got to collaborate with a boss or something like that you miss out on this opportunity to have that type of partnership with someone which which like I said earlier like um the allure of it is strong it's like it's still a thing i like fantasize about you know um i would love to have that type of like work relationship with someone in the future um and it's it's not going to happen right now with this company because it's already spun up and going but it could happen in other ways you know it could start something else in the future so you miss out on that um i think also that the the bear case is like it's just so hard to get started with the business it's like everything is trying to kill you i mean that that's not even true because that implies like attention on you it's like it's like you're starving in the desert it's not that you're actively hunted it's like no one cares like nature isn't different but it's still very dangerous yeah it's it's like you know nobody cares nobody cares what you're doing and so we're not built to do that i think as like humans like our psychology it's just you're not you're not supposed to go out into the forest alone for years and just be by yourself we're social creatures we need to be around other people we get energy from other people and and and the the bare case is your you might have an amazing idea for a thing and you might be you know compromising on the outcome you could have because you don't have the network around you.

1:03:17You might find the right product, right time, right market, right opportunity, and the limiting factor is you. And the engine can't take the horsepower or whatever, and you don't make it. I don't know if for my first company, doing it by myself fully would have been sustainable. I don't know. I don't know. I didn't have a large group of co-founders. I didn't have a large network. but I think it's really challenging and you kind of burn yourself out and then you never do it again that's kind of the bare case you're just like wow I just spent two years alone working on this and I was living out of coffee shops and sleeping on someone's couch and I didn't make any money and what do you learn?

1:03:57What do you have at the end? The bold case for it though I think is one of this story of personal transformation in this journey and it's a thing people can't take from you if you make it from scratch and it's just yours like well you know i i don't have i don't have children yet and uh i've always been like envious of like um a bit envious of women that they can like birth a child i think it's just like the most hardcore thing in the world to like make another life form you know as a as a man you participate in a part of it but like it grows in the woman you know it's like it literally comes from your flesh it's it's pretty metal you think about it and so i don't get to do that you know exactly like that you know i i can i can i can write music or make other things but i think this this uh it's pursuit of expressing this thing and having it just be yours um if you're solo it's only yours it's like yours the step came from coming from an idea inside of your head into this thing that exists in the world and along the way you get to go through this journey of personal transformation and learning different things and the company the company i find is like this mirror like it shows you every imperfection in yourself and weakness all the time all the time uh it's inescapable like like your weaknesses the company will find a way to highlight them and make it the hardest obstacle that you have to overcome it's like it's it's like this adaptive video game on top of your life or something it's kind of crazy and so the upside of that is like it's this constant hardcore journey.

1:05:27It's like the extreme sport version of that. So I think there's an upside in terms of the accelerated personal growth and transformation if you want that. And not everyone wants that and not every company pushes, depending on your skills or your abilities or talents or what's required of the company, you're going to get different journeys that you go through. But I think the piece that really is the bold case is you have this thing that uniquely feels like it's yours. and there's something just like really, I don't even really know how to describe it. It's like lasting to have something that you create like that that can just become one of those institutions.

1:06:06You can make it into this thing that will exist and then eventually the people working on it won't even know who you are. Like institutions that just stick around forever. No one knows really. It fades away. I saw this talk from a guy who, long time exec at Disney, who worked on The Lion King, which I was talking about earlier. And The Lion King, the story of it, was their childhood story from their family that they told. And he just had it as a kid and made the movie and then produced the movie and the music and all the stuff. But the story of it, I believe, just came out of this. It was just a thing he had as a kid.

1:06:45And when you go see it on Broadway or see the movie, it's not the story of him. It's the story of the story itself that continues on. It's this kind of self-continuing process, this meme that exists in the world. And I think there's an element of making those things exist in the world. That is the desire of the entrepreneur. Can I get a thing spinning? I'm spinning a plate and then eventually it just flies by itself. And there's an element of it that if it's like it fully came from you, it's just really satisfying. And I think that's when it's with other people. again like the things that go poorly you can blame them the things that are successes are shared you know it's not as this like extreme fully full ownership and agency and that's the double-edged sword where it's also it can be a terrible thing um but when it works it really works it's really special and i think it becomes this thing that like you you like never want to let let go of as well you know and and uh who knows what happens with you know companies at the end of the day it's just a business you know as well like you know it's um he knows where markets go or uh companies merge and sell all the time and stuff but for that for that moment when it starts actually working like where work us is right now like it's we're ripping it's going i'm having more fun right now right now than any time my entire career i never thought i could have this much fun working and feel like this about my job it's crazy and i don't think i i would have been able to get this specifically like this um if i had been a piece starting it with a bunch of other people i just think i wouldn't have the same level of connection to it and so that's it's a vanishingly small number of people that get to the position that i'm in right now i don't even know what this i don't even i don't want to know what the odds are you know um it's like i've gone through all these gates and like survived um but i i think there is a there is a bold case that's like very special around that and and it's probably something that's like not reproducible like i don't know if i'll get another one of these in my career like this it's it's again getting product market fit is like running the algorithm and like rolling the dice it's just very hard to get multiple ones um and and to be part of it from from the beginning where it was just this like scratched idea and my notebook and these things inside my head you really realize like the world is so like malleable.

1:09:05Like a lot of people talk about this idea of like everything around you was just made by people like you. And I remember distinctly like realizing that about the world. But when you build something from scratch yourself and you make every bit of it from the beginning, because it literally starts out as nothing. It doesn't exist. It's a figment in your idea. It's just like, I've heard this quote, like a secret is something that only one person knows. At the very beginning of the company, that's it. only you know it you believe this thing once you go through that experience you really realize that everything in the world like started off like that and that's just a kind of a special connection to like humanity in this way so i think that's it's it's it's extraordinarily you know unlikely and extraordinarily challenging to get to that point um but that is like kind of i think the ultimate you know the ultimate bull case for it and what i would say is it's like worth shooting for because like you only get one life you get one shot you know like why not why not swing as hard as you can what a way to end it yeah it's beautiful thanks for doing this thank you for having me by it's great to see you if you enjoyed this conversation we would love it if you could share solo founders with everyone you know particularly people who are considering starting companies solo or who are already doing it you know the entire goal of what we do is to normalize solo founding encourage more people to solo found instead of end up with co-founders of convenience if you'd like and we'd really appreciate it you can go leave a review on apple you can go give us a thumbs up you can subscribe on the YouTube channel.

1:10:29Anything helps. And of course, if you are starting a company or considering starting a company, you should go look at the Solo Founders program. We work together with you in San Francisco alongside of a bunch of other Solo Founders. The idea is it's much better to be Solo together than to be Solo alone. I'll spend a lot of time helping you. And we also invest$100 ,000 in your company. So if you're excited to learn more about that, go check out solofounders.com slash program.

From the publisher

Michael Grinich built WorkOS solo — now a $2B company and the enterprise infrastructure behind OpenAI, Anthropic, and Replit — with no co-founder. So when he says "it's not the blood bond it was made out to be," it lands. This conversation is his case against the ride-or-die co-founder myth, the question he thinks actually matters before you start a company, and the honest bear and bull case for going it alone.

Topics covered:

  • Why co-founders aren't a blood bond — and "are you the one who holds it forever?"
  • The founder "mental disorder," and why you only need one person who has it
  • The bear and bull case for solo founding — from John Lennon to "the company is a mirror"
  • How to pick the idea: a notebook, four filters, and lessons borrowed from stand-up comedy
  • Why "pivots are the most traumatic thing you can do to a business"
  • The case for founder-led sales — and hiring a head of sales as a partner, not a handoff

Guest: Michael Grinich — solo founder and CEO of WorkOS, the infrastructure that makes startups enterprise-ready.

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