How He Scaled Circle to $50M ARR in 5 years (Sid Yadav, Circle)

after maybe 9 months in like private beta. Shot straight up from like $200K in ARR, opening up the floodgates to like $1 million in ARR within 3 months. That's about when we closed our seed round, which was $4 million round at a $40 mil valuation. You know, one day I remember asking him, I might have been like 10 or 11, like, hey dad, like, what is a doctor's salary? Gave me some number. It might have been like, I don't know, $100,000 or whatever. And then I was like, what is Bill Gates' salary? So he does a search and he's worth like billions of dollars. And I was like, oh, okay. That's interesting. So why does everyone want me to be a doctor? Why can't I just be Bill Gates? I think you kind of need that blind optimism. Yeah, right. Especially if you're like an immigrant and you're not like born in Silicon Valley.

Raising a million, a couple million doesn't mean anything if you can't survive afterwards.

To build software for people who then go on to start businesses and become millionaires like that just felt to me and still does like the most fulfilling thing that I could do.

Take me back to the first 10 years of your life, which kind of sounds insane to say, but you moved from India to New Zealand. Talk to me a little bit about that experience and about what that taught you about being resourceful. I know your family moved there with basically nothing. Let's start there. I think that's fascinating.

Yes, I was born in 1991. Family moved to Uganda, age 4, for a couple of years, then moved back. I was basically like this very outdoorsy kid. So actually I never used my first computer until I was like 10.

Right.

And so I had this like pre-computer life and post-computer life. And the pre-computer life is basically that, you know, I'd go to school, come home, and I'd just be outside like till my mom asked me to come home and it'd be like playing cricket on the street. So we literally like, we had these streets in India that you'd like block the street to play cricket. And then when a car comes through, you'd be like, all right guys, pause game.

Now we have to pause.

Yeah. Yeah. And I had a lot of friends actually in the neighborhood. And, you know, it's like, it's kind of different, I feel, in like places like New Zealand and US where I moved to after. But in India, it's like the whole neighborhood kind of just knows you. And so people would like come to my house and we would just start like playing stuff. And then if you got bored, you're like, all right, what's next? Well, let's play badminton. Yeah, let's play volleyball. Yeah. So it's very, very like different life to the life that I live now or in the post-computer days. But I think the one thing that I, I feel like I've carried through is being exposed to like people of different strata, like in India is very common. Like some of my best friends actually like lived in slums and huts and stuff. It didn't matter. Like we never thought about it. We were just kids out there, like having fun.

Playing badminton or cricket.

Yeah. And the spirit of adventure. Like, we would go off, like, biking up a hill, which, by the way, like, I don't know if a parent should let their child do that when you're like 7 or 8, but I'd do that, you know, all kinds of crazy stuff. Or like, also, I think it's a different time, like '90s and early 2000s, where parents didn't care as much what the kids are up to.

Yeah, they felt they could trust you.

Yeah.

Or trust society.

Yeah. I'd actually even ride a scooter.

Really?

Around my, my little town.

When you were like 10?

Yeah. That's insane. 10. So I'd be on the scooter just like, you know, and my mom wanted like groceries or whatever. Yeah.

Like, go get them.

Yeah. Just go out, get the groceries. But yeah, I think my life really changed once we moved to New Zealand.

Right. And you had your computer in New Zealand, right?

Yeah. And that's a funny story too. So, so imagine me being this like super outdoorsy kid. Yeah. Like never used a device before. It was all about like playing sports and stuff. And we moved to New Zealand, like the south of New Zealand, the southernmost city of New Zealand. Next up is like Antarctica, place called Invercargill. And it's a completely different environment. I mean, one, it's like super fresh and modern and like streets are clean, people are nice, but at least that like in my neighborhood, like there's no friends.

Yeah.

So like, what do you do all day? Yeah, right. Completely different. Lifestyle. And so we do this one thing because it took my parents about a year to find a job. The New Zealand has this very, very generous, like, welfare system for people. So in that year, we would just go to garage sales every week and I'd be like, oh my God, like, there's so much cool stuff for like $2, for $5, for $10. And in one of those garage sales, my dad found our first computer for like, I think it was couple hundred bucks.

Yeah.

An old Windows ME computer. And so he brings that home and then I'm just like, I'm just obsessed with this computer. And it wasn't surprisingly like the games, like I wasn't playing any games on the computer. It was like I went straight into like somehow I don't know, I found myself on like AngelFire, GeoCities, building websites on like webmaster forums. Yeah., getting like, like learning HTML, CSS.

Yeah.

And yeah, that rabbit hole I think was very, very responsible for like me being here today.

Yeah. Why do you think you, you did go like, do you think it was the fact that there was like a lack of community outside of the household that just made it so much more interesting to be basically in this, this box of information that you could just access forever and ever? Where it's like, do you think that's the reason you gravitated more towards being on the computer and like learning things online?

Totally. I think when I look back, it was like, I was an adventurous kid. And so pre-age 10 in India, I was like outdoor adventure. And post-age 10, it was like adventure in like the cyberspace. And yeah, there's something about like, I don't know, not having friends in your neighborhood anymore and just having this device and you come home and it was basically TV and computer. And honestly, like, it's funny to connect the dots because when I look back, it wasn't even like, 'cause blogs weren't around like in 2001. It was actually like forums that got me into like programming. So, you know, like the idea is like, I'm building my first website. It's called Sid's Pokémon Website.

Great name. Yeah.

It's got a Pokédex. It's got like the history of Pokémon. It's got my favorite Pokémon., and now I need help with like aligning tables and navigation. Yeah. And what do you do? So you look up like, you know, HTML help tables, whatever. And you'd find these forums where people would share like great tutorials. Mm-hmm. And one rabbit hole another led me from like learning how to do very basic like HTML, CSS, CSS programming to like blogging in 2002. 'Cause blogger.com had just launched. Yeah.

And that made it much easier to to write and post things. Yes.

Yes. And so I remember discovering my first blog and I was like, oh cool, this is a journal. Like I could have like Sid's Journal.

Yeah.

So I started actually my first, my second website was like sidsfunstuff.com. I clearly love the domains. Ah, no, I don't. But I love the, like the Sid's X branding. There's, you know, back when, back then, like you had all these websites, like there's one called emotioneric.com. It was this guy Eric who just posts photos of himself like making goofy emotions. And that was like viral.

For the entire website.

Yeah. And so you had these like individual websites. So I started a blog just out of, again, like sheer boredom and curiosity and just started writing online.

Yeah. Can we, I wanna talk before we get into the blog, you've also mentioned being really interested in like, you know, technology and Bill Gates and these types of founders early on. How did you discover those, you know, like American tech icons at that age? What was that discovery like?

Yeah, so it's super funny. It's like, it's by sheer accident. So, you know, until maybe about age 12 or 13, I just want to be a doctor. Like when you grow up in India, like at least back then, your parents just wanted you to be like a doctor or an engineer. Like they're like two professions, right? And actually, like my grandfather's a doctor. So all of my cousins and I, like, we dreamt of being a doctor. My dad is someone who I have a lot of conversations with about just life, philosophy, business. So, you know, one day I remember asking him, I might have been like 10 or 11, like, hey, Dad, like, what is, what is a doctor's salary? Because I think a lot about what my dad's salary was because, you know, he's finding a job and then we'd like keep up with like, oh, this job is now a higher salary. So I was like, what is a doctor's salary? And he gave me some number. It might have been like, I don't know, $100,000 or whatever. And then I was like, what is Bill Gates' salary? And so he's like, oh, good question. Like, let's check it out. So he does a search and he's worth like billions of dollars. And I was like, oh, okay, that's interesting. So why does everyone want me to be a doctor? Yeah, why can't I just be Bill Gates? And my dad kind of like honed in on that curiosity and remember like reading some very early books about Bill Gates. I think there's like a couple biographies he'd written. Mm-hmm. And then I went into another rabbit hole of like reading about the Google founders, reading about the Yahoo founders. Yeah. And then slowly but surely developed this like fascination of, oh, basically the path is to like get into Harvard and Stanford, to drop out, and then to start a company in the garage. And to do that, I don't— I shouldn't be in New Zealand. I need to be in America. Yeah. And it was like, it was really as simple as like just reading these books, reading about these people, being like, oh, like this doesn't make any sense whatsoever to aspire to have like a doctor salary when I could be like Bill Gates.

Yeah, that seems like so— like it seems like such sophisticated— it's so simple but so sophisticated level of thinking at that age. Is that when you were really drawn to going to the US and starting a company and really leaving New Zealand as well?

Yeah, so I think, you know, at that point it was like this like pipe dream, right? It was like, oh, like when I grow up, I want to go to America and like get into Harvard or Stanford and then drop out and then start my own company. But it was like, you know, it was like a child's like dream to be like, I don't know, people, like the way people dream about like astronaut or like being a sports star or whatever. Yeah. I think the actualizable plan to move to America actually started a little further down the line when we get into my blogging days.

Yeah, I mean, we can go there right now. Revzi.org, we can talk about it. Um, what, what made you start that blog specifically, and how were you able to grow to 100,000 active users, uh, you know, with even more website visitors at a single month? Like, how are you able to do that at such a young age?

Yeah, so, um, So, so I had my journal initially, right? 2002 era. And the thing I'd do is I'd get home from school, I'd like get on the internet, I'd learn about new products, I'd download new tools, I'd play around with them. So one day I just remember writing an article about Blogger.com, like the tool on which I was writing this, because I remember it was actually acquired by Google. And that was like a big event that Google has now bought blogger. So I wrote about that. And at some point, I think it might have been like 2003, 2004, came like TechCrunch.

Yep.

Right. And so this is like early Web 2.0 days, post-dot-com bubble crash, et cetera, where all of these new things started launching. Right. So there's like Ajax, there's like Flickr, MySpace, et cetera. And my thing was I just started writing about them and at some point I was like, okay, no one's gonna read like Sid's journal on like Sid's fun stuff. Like they're not gonna take me seriously. So I need a better brand. And so I was like, what, like what is this? A Web 2.0 like revolution, like Revolution 2.0, Rev2. How about Rev2? Yeah. So registered the domain rev2.org. And basically turned that into a tech blog essentially. So it was like way back in the day there was TechCrunch, Mashable, GigaOM, ReadWriteWeb, and Reptoodle. So I was very proud to be like number 4, number 5 in that, in that early blogging era.

Yeah, it's insane. I can't believe you started it. I think you mentioned like changing the name and being really aware of the branding. You told people like, I'm not a kid, like I'm a chef who works throughout the day, right? Like you had a whole alternate persona that you told people you were.

Yeah. So basically until I showed up to America at like age 20, I had this alter ego on the internet, which was more like, okay, it's still my name and everything, but it was like, oh, but Sid Yadav is like a chef by day who lives in New Zealand and then like blogs at night. Like that was kind of my alter ego. And the thinking was very basic. Like if people find out I'm like 14, then like they're not going to take my like 10,000 blog posts on like Facebook. And there was a post that I did on Facebook that was like a 10,000-word post. Yeah. Wrote about every single feature that the product had back in the day. Like they're not going to take that stuff seriously. Right. So it was just like, and people would ask me, so eventually when I had freelance writers, they would ask me like, like, hey, like, why are you not online, like, during the day? Like, you're in New Zealand. Like, why are you— why do we only see you, like, after, like, 6 PM or whatever? And I was like, oh, because I'm a chef.

Yeah.

And so it kind of started like that. And then that turned into my, like, alter ego. Yeah. Online. And then a big milestone actually with Rev too. So, you know, I start blogging and now my routine turned into, like, come home from school, write about 5 to 10 startups, product launches, VC investments. Yeah. And then do my homework and then go to bed.

Yeah. Repeat.

Yeah.

That's insane. How do you keep up that stamina? That feels like quite a lot of time and commitment into writing those.

Honestly, it was all just kind of innate, innate passion, right? It was like I discovered this, like the coolest invention ever. Like I wanted to be Bill Gates.

Yeah. Oh.

I'm like 12, I'm like 13, right? So what do I do in the meantime? It's like, well, why don't I just write about these startups that exist in America? And so there wasn't that much more thinking behind it, but there was like this intrinsic motivation to be like, oh my God, Flickr just launched tags. Like, that's a big event. Now, and I'd like, I'd dig into that feature. I'd be like, oh, like, so how does this change? Like, the behavior and what happens to like RSS feeds. Can we get RSS feeds for every tag? And so just kind of nerd out about these topics. And then so slowly the readership developed and then I had like 100,000 readers over time and then made my first dollar on the internet selling ad slots.

What was that like? Did you tell— I mean, you're close to your dad, you mentioned. Did you go home and tell him like, oh, you were home and you're like, Dad, I just—

Oh, all the time. Yeah. So two things about my, my dad and my mom too, it's like they would talk about this stuff very openly. So they'd be like, oh, what do you like? What are you up to? And I'd be like, oh, I'm like, I just launched my blog or like, you know, I just wrote about Flickr or whatever. They'd be like, okay. They never verify, by the way. And that's a crazy thing. It's like they just kind of trusted that I was doing this stuff. And so like one day I start making money and, and the thing back then was like, I didn't have like a bank account, right? So how do you get paid? I was like, PayPal only.

Yep.

And back then PayPal had no way to get the money into New Zealand, into a New Zealand bank account. So even if like I want to transfer it to my dad's bank account, they didn't have that.

You just couldn't.

No. So, so guess what I do? So it's like, okay, well I can have an eBay account and I can use my PayPal funds on eBay US, right, to buy stuff to get it delivered right to New Zealand. So then, you know, I started buying like my first Xbox, you know, my first like PSP, first iPhone. It was all just like using the blogging money on PayPal to buy stuff.

And your parents like, where, where, where's this coming from? Who's ordering this stuff?

Honestly, it's like back then they couldn't afford a lot of this stuff too. So it's like, they were like, okay, cool. Like he's just going to buy stuff for himself. And then eventually, like, you know, I'd sponsor my own trip. So at some point I figured out how to get some money out. Into some like debit card. And then it was like, oh cool, I can sponsor my trip to America at 16 or India at age 17.

Yeah, that's awesome. I want to, I want to get into that, but I want to ask one question because I think you scaled up the writing side as well. And so like, I imagine this was your first, you know, sales, marketing, hiring. Like, what, what were those experiences like? And how does that translate to, you know, today in terms of you know, how were you able to manage a team? What lessons did you learn? Because I imagine that's quite jarring for a teenager to be like, all right, now we've got 4 writers, 5 writers. Can you tell me a little bit about scaling that and how that was like?

Yeah, I mean, I had to do the whole thing, right? So it started with like me having to do like, let's say, up to 10 blog posts a day. And then, you know, I would get exhausted by night, right? And then I had homework and stuff. So I was like, man, with the money I'm making, like, and back then it might have been like, I don't know, $2,000 a month. And then $3,000 a month. I was like, oh, I could maybe afford to pay someone like $20 an article. Yeah, right. And I was like, oh, then I wouldn't have to write that myself. That'd be pretty cool. Yeah. So I just put a post out on the blog saying we're hiring freelance writers and slowly we got to like, we have 5 writers. And so basically what I had back then is like I have this email thread every day where I would like get home from school read whatever's happened in America, make a list of like 10 possible topics, send this over to like the freelance writers, and we would just kind of divide and conquer. So it'd be like, oh, I'm doing the Google buying YouTube thing and you can do like the, I don't know, the Feed— whatever FeedBurner acquisition. Yeah, right. And so it's a very simple setup of like just one email thread. People take a topic, and then, and then I had to pay them out at the end of the month. So it's like, okay, PayPal payment. So kept it very simple initially. So it wasn't like I was interacting with my writers a lot, but I was reviewing drafts. You know, at some point Google Docs launches and then that was great. I was then like editor-in-chief of rev2.org.

Yeah.

Reviewing all of these drafts. So I don't know if like I intentionally like was thinking about like, oh, I'm now a manager.

Yeah.

It was more like, oh, I'm making a bit of money and I'd love to have some help like running this business. And it was very kind of gradual. And so there's so many things that I didn't do right, which I later learned to do. So like there was no like one-on-ones, there was no feedback system. It was just if you wrote good posts, I'll pay you X amount. And then eventually it was like $50 a post. Yeah. And if you don't, sorry, I can't. I don't accept it.

I'm not paying for this. It sucks. The ultimate meritocracy. Yeah, that's amazing. Um, I think it's really interesting how you're very online and you're very willing to just, you know, write these posts, find writers, um, figure out these problems. And you've talked about around this time, you know, I want to talk to you about going to the US for the first time and also cold emailing, like getting an interview with the, uh, the YouTube founders. I want to talk to you about that and what made you do both of those things? Yeah.

So the YouTube thing I can talk about. So our placement in the blogging ecosystem was the following, right? So it was okay, TechCrunch is like number 1. Mashable is number 2. Number 4 or 5, depending on the day, would be like Rev2. And so you had all these entrepreneurs in like Web 2.0 heyday, like wanting to launch their startup who couldn't get a TechCrunch article written about them, right? For whatever reason, there's just so many products for TechCrunch to cover.

Yeah.

So they'd reach out to me being one of the five. And so the YouTube founders did that really way back when it was like a dating site. Yeah, right. And so I was like, okay, cool, there's a dating site. So for me, it was like just like any other startup that I was writing about. Yeah. But, you know, okay, I noticed I think one of them like worked at PayPal before. I was like, that's kind of interesting. By this point, I was kind of tired of like writing the same type of post.

Because how long have you been doing it for at this point?

This would have been like 2005 or 2006. So probably like been running it for like 3 years.

Okay.

Yeah. And so, you know, these guys, Chad Hurley, Steve Chen, reach out and so I was like, hey, I don't really want to do like a typical like launch post, that's kind of like, I mean, I'm just doing those every day and all that. Why don't I do an interview with these guys?

Yeah.

And so, so they were like very down, right? Because they weren't getting written about. Yeah. So I basically like, yeah, yeah. And so it was actually written interview. I'm like, hey, like, here's like 10 questions. And they just wrote about like their vision for like video and how video affects dating. And like Flash was like a big thing back then. So they were about like I don't even think like HTML5 existed. So it was like video on Flash and how like people could have cool like dating profiles. And then I wrote about that and like it, things moved so fast. Like within months they had pivoted to like youtube.com, like a video sharing site. One fun fact I remember, by the way, I really feel like this is the key to like how YouTube went Like viral.

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They used to have an iPod Nano giveaway, like a daily iPod Nano giveaway to incentivize people to watch and like videos.

Really? So if you watch a couple of videos, you'd be eligible for like some giveaway?

Yes, they were giving away one iPod Nano a day. To random people who are liking and, um, watching, liking, and sharing videos.

Yeah.

Right. And I know this because I did that for 30 days because I wanted an iPod Nano.

Did you get it?

Uh, I didn't, unfortunately. And at some point I told people in my school, so we had an entire classroom of like little kids, um, in their like technology class, like sneaking in YouTube videos to be eligible for like an iPod Nano. I don't even know, like why I want— I think like I could have afforded it, but it was this fun, like, oh cool, if I just do this, like it's so tiny. Like, I don't know if they have that many users. Like I might just win an iPod Nano and that'd be pretty cool.

Yeah.

Uh, it'd be cool story to tell my friends. And I, and I really feel like it was right after this phase that, um, YouTube just went bonkers.

Yeah.

So I don't know if there's like direct like causation. Yeah. But it's definitely correlation to like some kind of a takeoff event.

Yeah. Did they, did they do that for a long time? Do you remember? Or was it like temporary?

Maybe for like 2 to 3 months.

Oh wow. Not too long.

No. And then I remember like videos just started to go viral.

Yeah.

Right. And so you had all the early hits, you know, like the Numa Numa guy, you know, the Star Wars kid, etc. The classics. And these would happen one after another, by the way. So it'd be like, there'd be like a viral event. I would watch it. We'd all watch it at school. We'd share it and it'd be like the new thing.

Yeah, interesting. That's maybe— yeah, maybe it is the fact that, you know, people like you were sharing it to other people.

Like, I think you have to incentivize like demand somehow, right? So you've got like a bit of supply. How do you get people to engage with it?

Yeah.

And I kind of feel like that was their like very initial hack. Yeah, that might have played a part.

That's interesting. Did you ever think like, I want to join these guys, what they're building, or you were still like, no, I like, I like blogging and I want to keep blogging because, you know, I mean, at this point I just had school, right?

So, so I was like, 8th grade and then 9th grade and then 10th. And then I just like, I hated so much of school.

Why?

Because what they were teaching me, I could tell was not very relevant to like this world that I like wrote about and followed. Yeah, right. And so it was like, why do I need any of this stuff when I can write? Eventually I could code, I could make money. Yeah. And so I would just think all day about like, hey,, do you have to get into Stanford and Harvard and drop out, or can you just like drop out of school and then you could start a company? Like, maybe that's even better.

Yeah. Just don't even go the whole route. Just go quicker.

Yeah. But the problem was I was in New Zealand, right?

Yeah.

And so when I talked to my dad about it, he was like, but you do need like, you do need a degree to get an H-1B visa.

Yeah.

To then get a job. And I was like, oh, shit. I guess it makes sense. Yeah. Okay.

Because let's talk about then because Around 16 or so, you go to the US for the first time. Is that also when you started working less on Rev2.org or?

At this point, I think I was still kind of active. Okay. It trailed off and I sold the business when I was like 18, like graduating high school.

Yeah.

I was actually going to college and I don't— I didn't think I could like keep up that writing routine. But yeah, this was 16. So using that blogging money, you know, reached out to like a distant cousin.

Yeah.

Who, you know, through some family relative I heard, like, lived in Silicon Valley.

Like, I need to meet this guy. I need to go there.

And actually his father, right, was actually like a success in the Valley. Wow. He'd worked, I think, at Sun Microsystems.

Nice.

Yeah. Like way back in the day and actually had like started a company and given a hit. And so I met his grandfather actually, on a trip to India, just like very randomly. And he was like, oh, what do you do? And I was like, I blog. And he was like, oh, that's cool. I live in Silicon Valley and you should visit us. Yeah. Um, and so I was like, I kind of took him up on it. Yeah. And so he had his, um, uh, his son, uh, whose name's Rishi. So my like second cousin, um, who's very welcoming. He was like, yeah, dude, come on over. Like, you know, and he just graduated from Stanford. I think working, he was working at maybe Slide, some Max left and Slide.

Yeah.

And he was like, just come on over to the US for a few days. Happy to host you. And so, yeah, I just booked that ticket and I get picked up by Rishi. Actually, no, spent a couple of days in like a very, very low-cost hotel in San Francisco. And I don't have any money.

Yeah.

So I'm just eating like like 2-minute noodles off the like $20 I had or whatever. And then I get picked up by him. Oh my God. In his like very fancy car. And he takes me to Stanford because he just graduated there and his sister, I think, was at Stanford. And then he takes me to Google where his sister worked. And I'm like 16 and I'm like, you know, I've written about all of this stuff and I'm like seeing it in person. And I was like, like, oh my God, like, I need to get here, like, pronto. Like, I need to figure out a life path to get here. Yeah. Because this is clearly, like, the place to be.

Yeah, that's beautiful. Was it that clear in that moment? You were just, like, in shock and awe, like, I need to be here.

Absolutely. Yeah, absolutely. It was like, oh my God, like, yes, like, this is where the action is. Like, why do I need to graduate high school? Like, why do I need to, like, be in New Zealand for the next few years when, like, I could be here and it felt like things were taking off, right? This is like peak Web 2.0, like Twitter and Facebook and everything. And I kept feeling like, damn, I'm missing it. Like, I'm missing like that. Like, because I'd read a lot about the dot-com bubble. I was like, I'm missing like a bubble right now.

Yeah, that's painful. So you get back and then what? Because I imagine you get back, you might feel a little bit hopeless. Like, you know, I'm stuck here. I still have to finish high school. Like, is that when you started charting a path or what was that experience like when you're back at home?

Like, shit. Yeah, absolutely. So, you know, I'd have conversations with my dad about this very openly. That's right. I want to go to America.

Like, what do I do?

And so he would explain to me how the visa system works. My dad, by the way, is like a visa genius. Like, you know, the way we ended up in New Zealand is like he went to Cyber Cafe and like applied for like a New Zealand permanent residency and we got it. Like, so he was very good at looking up this stuff. So he's like, okay, well, if you need the H-1B visa, like like, you kind of need to like graduate. And he's like, and so back then, actually, I wanted to go to Stanford and Harvard. And he was like, I suggest you do your CS degree here because it's going to be very expensive. I was like, okay, well, we'll figure it out. Like when I get into Stanford and Harvard, like how we're going to pay for it. But for now I'm taking the SATs. So I think I was one of 10 kids in New Zealand one year.

Thai country.

I studied for the SATs at took the SATs. By the way, no one in New Zealand knows what SATs are. What is SAT? Yeah. I was like, nope, I need to get into Stanford. I took the SATs. I think I had a good score, but not Stanford-worthy.

Okay.

And so that was kind of disheartening. And then eventually I was like, okay, maybe I should just follow my dad's advice. New Zealand is very, very generous with their student fees. There's basically no interest. I can go to University of Auckland, get my computer science degree, it's very accessible.

Yeah.

And then maybe after that, you know, I can, I can actually move over to America. So, so that was a plan that I developed. And to this day, I feel like the only reason I got a computer science degree is because it was an H-1B visa requirement.

Really?

100%.

Were you thinking about getting anything else or was it just like, hey, I need the visa. Okay, it's this.

It was, it was just the visa and it was like, okay, well, I know how to program. I know how to like build apps. And I'd launched this like this chart-topping app for the App Store, which we could talk about.

We should.

Yeah. And so it was like, well, but maybe I should learn like actual programming from like first principles. So that might be helpful too.

Yeah.

But that was like a very side thing. It's like, I don't know if I need that to like start a business or get a job, but maybe I should like, right, actually learn like the fundamentals of computer science.

Yeah. It's like you could have learned the fundamentals. You already knew a little bit. So it felt like safe in a way. Totally. And I had the visa. Uh, let's talk about that. You mentioned the app. Um, so you're still, you know, you've got Rev2Org, you've come back from the US. Uh, what are those sort of years before you start the CS degree look like? And, and, you know, what things were you building?

Yeah, so, um, you know, the way I got into programming was interesting, right? So I'm blogging on like a WordPress site and I'm installing plugins for all kinds of stuff. And then there's certain plugins that don't do like what I want to do. So I'd like, I'd be in the PHP code, like then learning a bit of PHP to like make the plugin work. Um, and then at some point I had the idea of like, hey, why don't, like, I write about products and startups all day and I don't think of myself as like a programmer, but like, why don't I just like learn a bit of programming by building an app?

Yeah.

Uh, and this is like 2007. I think the iPhone had just been announced and then launched kind of later in that year. And so I was like, what should I build? And, you know, thought about it. And I was like, it's interesting. Like Twitter's taking off and Twitter's all about like the 160 characters. And at the same time, when we write like journals, when people have journals, it's like super long form.

Yeah.

So what if you made an app where the entire idea of this, like journaling was like just 5 tweets to yourself every day. And so I created this app called Memairi. And, you know, it's like my dad still recalls, like, and by the way, like most of my conversations with him, he'll remind me about Memairi because like one of his fundamental memories is like me, like, so I lived like downstairs. I'd go up to his room and be like, Dad, like I've got a killer idea for like a journaling app. And he'd watch me like pace around, like talking about what it is that I want to build. Then I'd pull an all-nighter and I'd actually like a couple days in, I'd like, I'd actually build it, which is how Memari was born. Yeah. And then, you know, within a couple of weeks of that, it was written about on TechCrunch. Like for me, that was actually a bigger accomplishment than like writing about it myself because TechCrunch was like the number one.

Yep.

And then within a couple of months of that, I had an iPhone app for Memari that launched on the App Store, like within like 2 to 3 months of the App Store itself launching. So we were maybe one of the first like journaling apps.

Yeah.

On the App Store. And it was basically featured by Apple.

Yep.

On, on the App Store, which led to like 100,000 downloads.

It's insane. Insane. And while this is happening, are you thinking like, okay, maybe this is the thing that I can do instead of high school, instead of a CS degree? Or are you just like, hey, this is just a fun side project?

These are side projects. No, I mean, having read about and been inspired by like the Bill Gates and Steve Jobs of the world. I was like, like, that is clearly the actual ambition. This is like, because I also read about actually what these guys did in their like teens. Yeah, right. So Bill Gates had coded some stuff. I think he coded like a game. He'd coded like some kind of a device that like counted like the number of cars that like, oh yeah, on a road. And so I was like, oh, this is my version of that.

Yeah, right.

So it's like, oh, when they write a book about me, it was very like grandiose, right? When they write a book about me, this is going to be like one of the early, the early parts of that story. So I was very like, I think naive, grand, and like just delusional, honestly.

In a good way.

I think so.

Yeah.

Yeah.

I mean, if you didn't do that, you know, it would have been a much, you know, probably the programming degree would have been much harder. You probably wouldn't have even have seen the path going to the US as an option or potential, you know, really path you could go down that could lead you to where you want to go. Like you had a very clear mandate and vision because of that.

I think you kind of need that blind optimism. Yeah, right. Especially if you're like an immigrant and you're not like born in Silicon Valley, you kind of like, because your first goal is like, how do you, how do you get to like the Mecca first? Like to even be in the game, right?

Yeah.

And so, yeah, all of this was a part of kind of the bigger picture. Yeah, that journey. And yeah, so that app launched and featured by Apple and I sold it for like a dollar. So made a bunch of good money through Memairi.

Yeah.

Until about a few years ago, actually, there's still like—

they're still going?

Thousands of users using Memairi.

Wow.

And I like hate myself for the fact that I let the hosting and domain expire.

Because you could have just kept selling it back to the—

Or just like it was a cool thing to just keep going.

Like there's all these people who kept journaling for years and now they can't anymore.

No. And I lost the domain. I lost the hosting. I think about this like once a week, actually. I'm like, once a week, dude. I mean, all these memories that people wrote down, they're gone. They're gone. Yeah.

Who let it expire?

I did, because I wasn't checking it after, like, moving to America and stuff.

Oh, shit.

And I kind of thought like, oh, it's maybe dead. But then, yeah,, you know, realize, no, like there are actually people, because I heard about them when it expired. I was like, oh crap.

Yeah.

Cause everyone put a message like, yo, yeah, it's like, hey, what's wrong with Memari? I was like, oh my God, it's like 2018 and you're still using Memari.

You ever found anything better?

Right.

That's amazing. That's, I'm curious is what is then we can get into this, but like, you know, with you today at Circle, but I imagine you've built you know, these are projects you're not building to last and not to endure. And like, there may be more so just like, oh, how can I learn? Or this fun— this is fun at the moment. When you started your CS degree, um, did you start thinking about, hey, what is something I would want to do that's like longer term, um, very, very heavy investment? Or was it still like, hey, what are some interesting things I can work on right now?

Um, it was more of the latter. It was like just side projects because I kind of had a very keen awareness of the fact that, like, I wasn't in the game, like, until I got to America. Like, I'm not playing the game, right? So, like, I'm not going to start a company in New Zealand. Actually, my biggest nightmare was, like, graduating with a CS degree and ending up as, like, a Java developer for some, like, healthcare company in New Zealand. Yeah. Earning, like, $50,000 a year.

Yeah.

Like, I would, like, dread that life path because I just knew so much about the world where I was like, well, America is the place to be. New Zealand is not the place to be if you're into, like, programming. I mean, it's great for, like, skiing and snowboarding and, yeah, like, like, you know, adventure stuff. Yeah.

It's not Silicon Valley.

Yeah, it's not. It's not Silicon Valley. It's not America. It's not even New York City. No. And so for me, it was all about like getting into the game. It's like, how do I get to the game? Yeah. And then I'll like start my— the big thing.

Yeah. Interesting. Okay, so you go through your degree, you build up experience, you've got some side project. What was— were there any notable ones we should touch on? Because I feel like you've done a lot of Like interesting side projects.

Oh my God, there's so many, dude. There's one called Committee. And the idea with Committee was like, it's kind of like, it's like from the creator of Memari comes Committee. It's like the idea is like, hey, you have a bunch of goals. Like let's say you want to like work out or you want to get fit or whatever. Like the idea was like you commit to that goal and you check in once a day with like a note about how you did that day. And then you could invite your friends to the app. And they would also commit to goals and they could follow each other and like—

Accountability.

See, yeah, so it's like basically accountability plus goal tracking plus semi-social network. That also like, that did okay. It wasn't as successful as Memari, but I do remember I think got like 20,000 users or so and it did get written about on like TechCrunch.

That's amazing. That's awesome. I love how your sort of, your shit like Picasso like painted Thousands of paintings, right? And most of them no one's ever seen. And it's like you're out here just putting, you know, putting up shots like it's just project after project after project. Like you've got an insane volume.

Yeah. And you know what it is actually? It was like I kind of like I was such a nerdy, like, tech kid, right? I really felt at that age that, like, life is meaningless unless I'm working on—

Wow.

Something like this. And then I'd be all in. And then it's like all-nighters, that's all I would think about. That's all I dream about. I'd show it to like everyone around me, obviously show it to my dad and he'd be like proud of me. And then I'd launch it. And then it's like that rush is something that I got very used to and I had like multiple times, thankfully. And, you know, there's something about like being in the zone and just like something takes over you when you have an idea that you are passionate about. Yeah. And I wasn't even a great programmer, but I learned how to program only because I wanted these ideas to exist. Yeah. And really, like, looking back, I was like, yeah, it's that rush that I kind of chased, but then eventually chased at a bigger scale. Yeah. Once I got to America.

Did you get bored of certain scales once you'd hit them? Even during this time, like with some side projects?

That did happen. Yes. So, so yeah, this would last like the rush would last maybe like 3 months or so. 6 months and then you'd get all these like requests, right?

Okay, can we update the product or—

Oh, all the time. It's like, so I maintain a spreadsheet of like all the requests. I would reply to all the emails. Memari at some point was getting like 20 emails a day with like, hey, you should add like an RSS feed or you should add like a calendar view, right? And what would happen is like eventually it'd be like, because there's very little monetization, with this stuff and I didn't see these things like becoming company. I was like, I'm kind of bored of just like improving the product and like, you know, fixing the bugs or whatever. And then I'd move on to like the next thing. I'd still keep this running, but it'd be like, I need a new idea.

Yeah.

And it was just like project after project.

Yeah. Do you think you built a muscle for spotting opportunity around this time? Because you start a lot of different things. Like, you know, a blog is very different to an app, but you found product market fit. To quite a big extent for both of them, do you think?

Yeah, totally. Yeah. I mean, so worth noting that I was blogging, right? So I was writing about thousands of startups. Yeah, I probably did like 5,000+ posts on just like startups in that era. So I had written about like basically every kind of product business model, like its marketplace, early SaaS, etc. Right. So in my own way, I was kind of like mapping out the industry, though that was not the intention. Yeah. And I kind of knew what it took because I then write about like the venture rounds, right? Yeah.

So, so like you could see the success.

Flickr raises like a Series B or YouTube raises B and then gets bought by Google or whatever. Like that was big news.

Yeah.

And so I could see patterns in terms of like what actually took off and turned a big business. Yeah. And I wasn't delusional enough to think like, oh, I can tell turn Mamari into like a big business. It was like, no, this is like a fun project. Maybe I can make a bit of money.

Yeah. A little bit delusional, not delusional enough.

Yeah. It was like a grand delusion at a longer time horizon.

Right. You're like, this is like when they write the book about me, this is going to be one of those footnotes in the first chapter.

Right. Right.

That's amazing. Well, tell me about when you moved finally. This must have been amazing. You must have felt euphoric finally moving to the US. Tell me about what that was like and why you chose the company you ended up working for.

Yeah. So last year of doing my CS degree, I had a bad breakup. So, okay, during CS I had a very normal, like, college life. Yeah. And actually very fun times in New Zealand. Yeah. New Zealand is a very fun place to, like, be in university and just, like, you know, watch, like, go out for rugby games and go to bars and just, like, have a normal fun life. I mean, also attend lectures and stuff, but I had a bad breakup. I was fairly depressed and I was like, what do I do? Like, I'm about to graduate in a year. Maybe I should make a trip to America again because the last time I was like, I was so inspired. Like, I'm kind of starting to feel like I'm losing that mojo a little bit. I'm starting to feel like maybe I'm like, I'm never going to end up in America. So why don't I just like go there, visit for like a month or so and maybe just even apply for a few jobs.

Yeah.

So made a trip out again, this time to New York City. I had a cousin who was studying at Stony Brook in Long Island, and the idea was, oh, maybe I could just stay with him and then like just go into the city and just kind of roam around. Yeah. So basically for a month, that's what I did. So I just— I'd come in this— come into New York City walk around like all of Central Park, all of Brooklyn Bridge, Times Square. I'd just be, I'd just be walking around and thinking of like ideas to get to America. And I feel like I know like every inch of like these spots because I've done so much walking and dreaming. And at the same time, I was kind of applying for like gigs, right? So it's like, hey, I'm visiting from New Zealand. I would love an internship. I don't care about the money. I just want to work for a startup. So I'd be writing in these job applications. A day before I'm supposed to go back to New Zealand, one of my other cousins is going to NYU. He intros me to these guys, Michael and Stefan from Whisper. It's a very early-stage startup. It's basically Clarity.fm before Clarity.fm. Yeah, very cool idea. Super early. They didn't have a team, right? And so they had like a bit of seed funding, but no team, like around $1 million, I think, or something. Yes. And so I'm like, okay, well, actually, this cousin, like, I didn't always trust his, like, recommendations on this kind of stuff. So I almost like, I like, I didn't feel like this interview is going to be worth it. Right. And so he was like semi-interning for them. He's like, he talks me up and that's his way of getting like credibility, I guess, with the founders he was interning for. And I was like, you know what? Like there's like literally nothing to lose. Like I'm going back to New Zealand tomorrow. And I still remember this is like, this could be in a movie, by the way. Like I, like I'm late for the LIRR train because I'm coming in from Long Island and I just get in without a ticket. 'cause I'm late for the interview, right? And the ticket conductor like is walking over, back then, like, I don't know if they do this now, but back then they used to check every ticket. And I realized, oh, in my bag I have like $50 worth of like quarters. And so essentially the guy comes over, I'm like, hey, sorry, I didn't buy a ticket, but would you like me to pay in quarters? He's like, take your time, take your time. And then he like, does the walk around. And then I get together like $20 worth of quarters in a bag, hand it over to him, then thankfully make my interview, which is in Times Square. I walk in and then I don't know what takes over me, but I'm like super confident. I'm like, I deserve to be here. Like, this is my chance. Yeah, I'm no longer having these thoughts of like, this thing's not going to work out. So we do the interview. I, you know, I show them like Memari and like my blogging experience and all that. They're kind of impressed by that. And basically they offer me a job on the spot, not knowing that I was flying back to New Zealand. Yeah. The next day.

Yeah. What'd you say?

So, so then I have to like reveal it to them, right? I was like, so actually, so would you guys mind if I like come back in a few months if you can sponsor my visa and I just work remotely? Yeah. And so they're like, Okay, so I think they were maybe desperate too. I don't know. So I fly back to New Zealand and I have like one semester remaining and then I just start like moonlighting for these guys and start working. They then fly me over. So I don't know, Michael and Stefan, like, oh, all the credit to them for allowing you and getting me into America. Yeah, that's my first break.

Yeah, that's amazing. That's such a cool story because you go in and you say like, I'll do everything, right? I'll do anything. And I think you've even, you know, you go there and you become the first engineer, but you're also designing and you're also doing all this other bunch of stuff. Um, you finish the semester and you go to New York. They sponsor the visa. What's the first day like? You get there and it's like, it's still a very small company. Uh, to your point, like, they maybe were a little bit desperate and needed your, your help too. Uh, what was that grind like?

Um, yeah, so actually I had flashbacks of the first my first day because it was actually in this neighborhood.

Oh, okay.

I remember being in a McDonald's and I was trying to think of like whether it's the McDonald's right opposite this building.

Yeah.

But there's some McDonald's I walk into and I'm like, this is my first day, right? And I'm just having a nervous breakdown. Like I'm all the way here. Like it's my first day for a job in New York City.

You don't know anyone else.

No, I don't know anyone else. And like they could just fire me and like now I'm back to like New Zealand, right? So like I remember that trip to McDonald's like before I show up to work. And, you know, it's like, it's a very classic, like, I guess, first day of like, you know, walk in and Stefan, the CTO, like sets me up with my computer. He gives me like the walkthrough and we'd worked together a little bit, I guess, remotely. So that, that helped. But I wasn't the best programmer. Right. And they kind of started to notice that, or like my intention to program stuff was just because like I cared about the thing I was building. Right. I just wanted to exist.. And so I was taking a ton of shortcuts, right? And like they had a ton of patience with that too. So like they, like I would just walk in with like crappy code or crappy work and Stefan would kind of sit me down and be like, hey, like this is not how you should do it. And he would kind of like tutor me on the spot. And then I learned from that. And then thankfully they hired like an eng2, eng3, et cetera. And then, and then I got better over time. And I really had to like learn about like, okay, well, the code is not the product. Like, right. The code is the code. And like these guys I'm working with, like they really care about the code and they're working within my code. Like I'm no longer building these like one-person apps where like the code basically doesn't matter. Yeah. You know, kind of like the Nomad List guy, right? Yeah. Like the PHP file, Peter Levels, right? Yeah. No, like the code actually matters. And so they taught me that lesson in that first year, but also to their credit, they gave me a lot of autonomy. So, you know, after a year I was basically like also like designing, PMing. I was kind of giving the other engineers guidelines. I was translating their vision into like mockups.

Yeah.

And so they let me do a lot actually.

Yeah. And you're only 22, 23 at this time, right?

Yeah, I might have been like 20 or 21. Yeah. What was—

because you tell me a little bit more about the company and give some context for listeners on what the company did and how your role evolved, like you're saying, after those engineers got hired and after you start making those mockups.

Yeah. So one thing to keep in mind is I was here on a 1-year visa, right? So New Zealand has like a J-1 visa and I was like, okay, well, I have to kind of crush it in year 1 for them to sponsor my H-1B. And so the company is basically Clarity.fm. So if you want to find an expert on any topic whatsoever, you log on, you go into the category, You find someone, and then the key differentiator. So unlike Clarity.fm, which might have been the wrong move actually, but it was very ambitious. It's like you can actually like, you could talk to the expert right then because they built a, or we built a Skype integration.

Instantaneous.

Yes. So it's like, hey, if you're struggling right now to write code or like you need mental health advice right now, you can log on and find people who are online right now on Skype, pay up, get connected via Skype, talk to them right now. And then it was just like very insane, like complex marketplace matching problem because it wasn't just like matching like, you know, buyers and sellers or whatever. It was like real-time active, like people who are active right now. And so liquidity was like a very, very tough, very tough challenge.

Yeah. Should have done the iPod Nano giveaways.

Yeah.

To get people on board.

Yeah. And actually, like, I think we were very bottlenecked on the on the like coach side. So like the, the people that you could talk to, it was like you might only find a couple of people and maybe they don't respond to you.

Right.

So there are a lot of lessons. Like we, I think, failed to raise our Series A.

Okay. Why?

We just never had product market fit. So the traction never happened. Yeah, but I learned like so much in that job, like trying to do it all and trying to get to product-market fit, right?

I think it's interesting you mentioned that because, you know, you, you, you have the one year and then you don't go back, um, to the company. What is your state of mind in that moment? Like, do you then decide, okay, I need to now join this type of company and learn these skills? Or after that year, how did you reflect on what you needed to level up, or what was the next steps for you?

Yeah, so what happened is, um, you know, my visa was expiring, right? The 1-year visa. And this is another story and tangent, but I basically met my wife at month 9 because I was online dating.

Okay. Before it was like really popular.

Yeah. Yeah. So this is on like OkCupid. Yeah. I was going on dates, go on a first date. The date lasts like 12 hours. Actually, before this, we chat for like a week. Okay. Constant chatting. We take a 1-day break. So like things are still fresh on our first date. And I remember telling my roommate, it's like, either I'm going to get married to this woman or I'm going to get kidnapped. It's going to be one or the other. And so I don't know, like, it just— it was like classic, like first love, like very, like romantic New York City vibe, right? And what happened is, so once we started like dating each other, the idea was, well, now I have to go back because my visa is expiring. I have to.

Yeah.

And so essentially we got married. We had— I had to stay out of the country for a year while my green card processed. So our entire family flew to New Zealand for the, for the wedding. And, and yes, in that year is when I actually met one of my first co-founders, Rudy, in Australia.

How? Let's, let's talk about that because This is a very monumental year.

Yeah. Yeah. So, so get back to New Zealand, get married. I'm just waiting for my like green card paperwork to arrive. We're like, hey, why don't we just travel in the meantime? So why don't we go to like Australia? So end up in Melbourne. I'm looking for like, I know by this time, by the way, I'd left Whisperd. Right. I also couldn't work for them kind of legally. Yeah. And so I'm basically looking for like short-term agency jobs in Melbourne while my green card processed. And so happened to interview for this agency where Rudy was like the technical director. So he hired me for this agency role. And, you know, we'd have this like we'd have a daily lunch essentially where we just talk about like everything. So this really felt like, okay, this is not any other like contract gig.

Yeah.

Because I tell him like all this stuff that I've just told you and he'd be like, man, like we got to like— But this is something.

Yeah, there's something we do.

And so we just we couldn't quite hit upon an idea to work on, but there's definitely like future co-founder vibe.

Yeah.

With him. And we do stuff like, you know, he took me like flotation tanking because he'd do that once a week and I'd be like, man, this like, this guy's like super interesting. He's much older than me. So getting to learn a lot from him. And then, you know, green card arrives in the mail. Mm-hmm. Fly over to America. Now I'm like fully legal. And now I can finally like enter the game of, yeah, you know, building my own company.

Yeah. What you've been trying to do for like a decade, basically.

Right, right. But the funny thing is actually by this time I had enough wisdom, like through the Whisperd experience to be like, I probably shouldn't just start a company because like companies are like very hard. And I found out through like Whisperd, right? Maybe actually what I need is like some work experience for like a, like a startup that actually finds product market fit. Right. And for me to like really level up my skills, learn from great people. So I had a lot of humility, you know, which I didn't have, I think, back in New Zealand. I was like, man, like, yeah, you need a whole team. Like there's so many like variables in product market fit. So it makes sense to kind of learn, right? And so basically start looking for jobs on AngelList. I get this email from this guy named Ankur, which says, hey, I don't want to play Tinder with you on AngelList, can we chat? And I'm like, there's something about that email, by the way, and like the way he phrased it, I was like, what the hell is this guy like?

Fascinating.

Yeah. And so that definitely stood out, right? So I walk in for an interview and it's like 4 guys and 2 of the co-founders and the early team and they're like, they just kind of grilled me for like 3 hours and then—

3 hours?

Yeah.

Wow.

Yeah. And there was no like one-on-one. It was like just these guys and these guys and me and they're just throwing all sorts of questions to me. And by the end of it, I was like, man, I like, I love these guys. Yeah. Like, I want to actually grab a beer. Like, I want to hang out with these guys even if I don't get a job. Like, I'm going to reach out to them just to hang out.

Yeah.

But thankfully, you know, Ankur offered me a job., as a first designer, first, uh, front-end engineer at Teachable.

Yeah, that's amazing. I can't— what, what, what was— you mentioned about Rudy as well, co-founder of Material, and you've talked about this, um, this interview. What was it? What create— what characteristics or traits did these people have that you're like, these guys are so interesting, I want to be around them, I want to learn more, that there's something there? Like, were there any patterns or tangible things that you felt like, well, this is really interesting?

I think that's one factor is definitely like just intellect, like sure, intellect. And like, you know, when you feel like, hmm, like I generally feel like I'm smarter than most people, but I don't know if I'm like smarter than this person in this area or many areas. Right. So there's definitely like a bit of like wanting to learn, but also like this sense of like being kind of intimidated by the intelligence. Right. And then there's like pure passion, like just the way they talk and the way they show up to things. It's like, man, like, yeah, let's like, let's do this. Yeah. There's like energy, right? Yeah. And, you know, it's just kind of— it's a vibe. It's like the vibe of someone and you just hit it off. You're like, oof, I could just keep talking to this person about ideas all day and like, maybe we could actually like build something cool.

Yeah, that's amazing. I think Warren Buffett says like there's 3 traits you want for, you know, someone you work with or a co-founder, like energy, Intelligence and integrity. And I think the energy one is very— I don't know if he calls it energy, but it's something similar. And I think it's very underrated, like energy transfer and being around people that are excited about what they're doing and, you know, just have raw horsepower. Like, that's super underrated.

I feel like 100% and you can't fake it, right? It's like either you have it or you don't.

Yeah.

Obviously being young kind of helps too. Like, you know, when you're like early 20s, mid-20s, you like, you naturally are like super curious and hungry and want to prove to prove yourself, etc.

Yeah.

But yeah, it was really just like that sense of, oof, like, yeah, I call Rudy my product soulmate. So it's that feeling of, oof, this person feels like a soulmate in one vector of my life.

Yeah, that's fascinating. I love that. That's a great framework. I mean, everyone, all of those guys at Teachable, Fedora back then, they were all super young as well.

Yes.

So you get this offer. You decide, I'm going to go for it, I'm going to become the first front-end engineer/designer. Um, now what? You know, how do you make sure this doesn't turn out to be a company that can't raise another round? Because as you know, you know, raising a million, a couple million doesn't mean anything if you can't survive afterwards. So like, what was your mindset going into that experience?

So going into that, um, I think where the company was is, uh, so Ankur had personally built the app himself because he was a Udemy instructor and Teachable, for those who don't know, is like a Shopify for online courses.

Yeah.

And so he built the app himself. But like me in the early days, it was like terrible code, you know, like the— you could just go to like slash, I think it was like stats.php on any Fedora school and just see all their metrics. So stuff like that. And so he— but he'd raised like a seed round from folks like Naval. Yep.. And so I was like, okay, like at least there's a shit ton of runway here and there's a bit of product market fit and the product exists, but he's now building out this early team to like rebuild the product. Yeah. And that was like, okay, well what I like about that is there's a product with semi product market fit. There's not a lot of revenue, but people like it, right? Unlike Whisperd where we kind of had to like invent every detail of the product, it was like, oh, Task number one is we just have to clone this guy's PHP app in way better code in Ruby on Rails and maybe build a bunch of features on top of that. But it's like there's a clear path to like something I can work on for like a year or two years. And he's got the funding and he seems very charismatic, like very good at raising. So like I can see more of a path to like potential, like exponential takeoff, like product market fit situation. And so, yeah, we were all in our like early 20s. I think I was the youngest, but like people are not far ahead.

A little bit older.

Yeah. So Ankur might have been like 25, 26. And there's a ton of energy. So yeah, we just show up and we'd work till like 8 PM, 9 PM. Just like we moved around like 6 WeWorks. And for 6 months, we, it was just all about getting his app to launch.

Just cloning it and then launching it.

Yep. Yeah. So then there's like a migration effort too, right? Because we had to move the early PHP customers over and that was a big deal.

Do you lose any or like, was there any problems in getting them to move over to this new app?

There are many problems. I don't recall if we lost any, but it was like, it was a lot of like, because we changed stuff on them, right? Yeah. Features that they were used to. And unlike a lot of other consumer apps, like they had built their business on top of Fedora, right? So like you're making money off this thing and like we change stuff on you. That part was not, was not fun. But like it wasn't extremely challenging. We kind of just pulled it off. Yeah. And it was weird timing too, because actually, so by this time my wife was pregnant.

You're young. You're in a country that, you know, you're an illegal alien. You're a legal alien now finally. Yeah. And that's incredibly scary, isn't it?

Incredibly scary. And actually she's pregnant before I found my job at Teachable. And so that was like, that was like a pure like YOLO mode of life of like, yes, I'm going to move to America and have a kid and join and join a startup and then start my own company one day. So the week that my wife gave birth to our daughter, like the week before that is I think when we had launched. And so like I remember like being in the delivery room, like debugging, uh, like right next to her.

Wow.

And just being around for like bugs and issues and stuff.

That's crazy. I think you said there was only like 2, 3, 4K MRR at that time as well. Um, that's kind of an insane— like, you've done obviously up until this point in your life in the story like some pretty wild things, but this is definitely like the most risky. Um, how did you think about like the asymmetric side of this? Like, you know, how did you make sure that worst case scenario, you guys were fine, or, you know, what were you thinking about that at all? Or you're just like, this is going to work?

I think back then I had the confidence to be like, hey, if I'm in America, I could probably get an engineering job. And if they let me go, I could probably get another one. So like for me, like just moving to America was such a big deal. Yeah. That I wasn't worried beyond that. I was like, once I get there, like once I'm in, I'm going to be set. And so sure, like, you know, I mean, it's very young age to have kids and like, that's like, try it at your own risk. It's definitely worked out for me, but like, you can never tell. But, but it was also like, I wasn't thinking much about the backup plans. It was like, it was a burn the boats type situation. And also I think I was just elated to just be in America where it's like, yep, this is the place to be. And there's so many opportunities and we'll figure something out.

It's like worst case scenario, I'm still in America.

Right, right. Like, you— like, it was so— like, it was so different from, like, my years, like, wanting to come to America and then, like, being on that 1-year visa that I was like, this feels, like, super secure to me. Yeah, from that perspective.

Yeah, because you finally didn't have this nagging thought, probably, like, I have to go back, or I have to figure out a way to stay here permanently.

Exactly.

Yeah, that makes a lot of sense. In the early days, talk— talk me through the experience of building Teachable, what ends up becoming called Teachable, because you were there for a while and it grows quite rapidly and your role sort of changes quite often. Can you walk me sort of step function through those changes and what the biggest sort of lessons were from your time there?

Yeah. So, so it started off as like the only designer, front-end engineer. So I just, I do mockups, I'd show it to the guys and then I just—

And then you'd build it.

Build it or build the front end of it, right? Yeah. We had way better backend engineers than me, by the way, thankfully at Teachable. And so I kept doing that and, you know, we launched and actually like MRR started to like grow. We hired my other co-founder Andy as our head of growth. Actually, back then he wasn't head of growth. He was almost like an intern too. So he has his own like story kind of like mine.

But like, I'll do anything.

Yeah, I'll do anything. You don't have to worry about paying me. And then, but within 6 months of that, he was head of growth because he had such great ideas and Through his contributions and through honestly Ankur's contributions, we started to grow and really find product market fit. Like, you know, going from like a million to I think might have been like 3 to 4 million or like something crazy like that.

Yeah.

In a year. And at this time the team starts to grow too because now it's like, well, we can afford to hire devs. And, you know, we kind of honestly, we, a couple of the hires that we made weren't the best. They didn't work out. And so I was kind of learning from that. Yeah.

What, what, what'd you learn?

So we, because we're all so young, we thought, okay, well, it's time to bring in devs who actually know what they're doing.

The adults.

The older devs, right? Yeah. And so a couple of devs that we hired were, were definitely older and more experienced, but they didn't have the energy, like the, the like passion, the mission-oriented like energy it takes to like keep up with what we needed. And we didn't have like the, the coding expertise that they had. So they were like technically very smart, right? And so this is a cultural mismatch, right? And I'd be the type of person along with actually like our very early team who I like, I love those guys. We'd just be like, we'd be the ones who cared so much. We'd be the ones like up at like up on a Saturday, like shipping stuff. I remember our CTO was like, we just work weekends because we cared so much. Right. And so Ankur noticed that. And actually when, when I agreed to join Teachable, I remember telling him, I was like, hey, like the reason I'm joining this company is I want product experience because I want to start my own company. So I'm going to join as a—

just got the job—

designer. But just so you know, like, I actually want to be a product manager. Yeah, right. I kind of just dropped that in there. And so a year in, you know, I was doing— so doing all the design work, and we then hired like an experienced product manager. That person, again, it's a similar category to the senior devs that I was describing. It's just a culture misfit. And also, I think we were too young too. So I don't just want to blame those guys. It was like we also were like young and crazy and stupid in many ways, right? And so we hired a product manager. That person didn't work out, but the devs would trust me, right? Because I was the designer. I was also part of the OG team, front-end developer. And we then hired an experienced head of product. That person didn't work out either. So I think that person lasted like 3 months or something. Yeah. And so eventually it's like, well, what do we do?. And so Ankur and I were talking, it's like, hey, like for now, just why don't you just do product? And back then there's no titles, do product. So on top of design, I was doing product. I was like trying to manage like the, you know, the GitHub cards and like the boards and stuff and also writing the specs. Cause that was kind of easy for me cause I was already doing the design anyways. Oh, I can just document my design and that's a spec. Yeah. And at some point I remember Ankur kind of called me into his office and he's like, hey, so decided that you're going to be the VP of product. And I was— and by the way, this is not a role that I'd asked for. Like, I just wanted product experience.

I just want to do product.

Yeah. So he was like, we're not going to hire over you.

Yeah.

You're not the VP of product. You should now figure out how to build your own product team and scale this thing. And I trust you.

Yeah.

And so that was like a major, major breakthrough. Yeah. So I kind of skipped a few steps, honestly. Like, I never had— like, I think I might have had for a couple of months the job title like a product manager before I was like VP of product at like a 50+ person company. Yeah. And tasked to like, not just like do product, but build, hire PMs and structure our teams. Um, because you know, this is a time when the, the eng team was growing too. So we were growing beyond like, we were, we used to be all in one room, like, you know, 10 devs or whatever at some point, or like 20. And we didn't have teams. So that was interesting. Or like, you're just like 20 people who are like, who could work on anything and there's no like functional areas or whatever. It's just like, oh, I'll do this and you do that and you just pair up. So we clearly needed a structure.

Yeah.

And so that structure started to form once I was promoted.

Yeah. And I think it's really interesting as well. You get this role and you sort of, you're always actively seeking out information and you do something with it. I think is very smart. You say, okay, who are the people in the city who have these roles? Let me just meet with them and try and learn from them. Like, what was— were there any insights from those conversations that you then directly applied to building the team, building the functions and sort of the structure?

Oh, a ton. Yeah. So my first thing was I just started reading like product books.

Yeah.

So like Marty Cagan, you know, there's like, I think Scott Belsky might have written a book. There's all these books. About just product management. I had to learn the function. So at some point I'm like, I got to meet PMs and heads of product. If I'm going to be recruiting one, like a PM, I need to know like what all this is about and learn from people who are way more experienced. So I basically just reached out to like any head of product I could find on LinkedIn that was based in New York. Yeah. And offered them like a coffee on me. And I did those meetings like roughly once a week. Yeah, I'd meet a head of product. Show up to their office or like meet at a cafe, pick their brain for like half an hour, an hour. By the way, people are so kind. Yeah, you do that. I still don't know, like, why a lot of them took that meeting with me because there's no, like, nothing transactional. Yeah, but it was a genuine outreach, right? It's like, hey, I've just been promoted. I don't know what I'm doing and I want to learn from you. Yeah. And so in those meetings, you know, they just talk about like how to structure teams. Like, that was a big thing. It's like, how do you structure teams. So you don't have one monolithic product org.

Yeah.

All sorts of things around like running like sprints versus like Kanban and like the point system and all that stuff. And then, you know, just getting great advice of like by the time I was then I hired PMs and I was managing PMs, it's like, hey, like your job is not to do their work, which is like, which came very naturally to me because I was actually like I was doing the design and front end at some point and I could do their work, but it was very overwhelming. It's like your job is actually to like give them structure, give them like a strategy to orient around so they do the work and you can be there to kind of guide them and look around the corners. And so at some point I was like, okay, I guess my job is to like basically translate the vision which Teachable's co-founders had, and then work with the engineering team and with work with the product people to actually make that come to life. Yeah.

Do you think that's— we'll jump ahead a little bit here. Do you think that's translated really well to you running Circle now? And sort of, I imagine, you know, with a company of your size now as well, like you can't be doing everyone's job. That's just impossible. And so you also have to sort of translate this vision into a strategy. Um, what sort of action, like actionable lessons have you taken from that experience into running a company? 'Cause I imagine at Teachable, you know, you're growing whilst you're learning all of these things. And so were there things that worked out at a smaller scale that didn't at a larger scale, or what was that sort of experience like of setting that up?

So I think at Teachable, I definitely learned a lot of things based on like what not to do and just learning through failure, honestly, right? I don't actually wanna give myself credit for like doing anything exceptional at Teachable, 'cause I was still learning mode. Okay. And, but I failed a lot. And so like, it's like you make the wrong hire, you hire someone super junior and you feel like you want to micromanage them and then you're doing their job and then you're doing your job and you're getting stressed out. Yeah, it's like, okay, let's not do that. And maybe by the tail end of my tenure at Teachable, like I was much, much better at all of this stuff. But really I feel like the key takeaways were more oriented around like learning by doing and failing. Right. And so it was just like all these experiences of like, oh, like, why did I mess up in this capacity? Or why are we not like shipping fast enough? Reflecting on that and then being like, okay, like this is what I do like differently next time. So to give you a very basic example, like, you know, at Teachable, I always felt like our actual vision and values were not super well, like documented. Right? It was kind of like in our heads and we all had our like versions of that vision in our heads. And obviously it's like Ankur's vision that actually mattered, right? But at Circle, we're like very intentional about like, and we've been that from day one. It's like, here's the vision, here's the values. We do update them, but there's never any lack of clarity on like what the vision and values are from the top down for folks to anchor to.

Right.

And then there's a ton of autonomy for the team leads and ICs to actually then anchor themselves to that versus like this lack of clarity where it's like, I think it's kind of like this and I think it's kind of like this. And you're like stepping on your— on each other's toes.

Is that the most important reason to have that setup is for, you know, for that clarity?

100%. Yeah. Yeah. It's clarity. And I think this is what empowers people to then have the autonomy Right? So you can't just be like, hey, I'm hiring someone super smart. And by the way, you got to be autonomous and figure it out. I don't think that's enough, right? I think you have to kind of inspire them and really make sure they're anchored to the vision. Trust but verify. And then over time you end up giving them a ton of autonomy and because they earn it, right? And then so, so if I was to like compare and contrast my style, like year 5 into Circle going way back to Teachable, it's like back then I was all about just like doing people's work. Yeah. And just getting frustrated when they weren't doing the work like I wanted them to do it.

Which is probably all the time.

All the time. Now I'm entirely about like the player coach thing of like, hey, like I'm here to set the vision, set the strategy, to coach people when they need it and to kind of like help them see around the corners. I don't really want to do anyone else's job because my job alone is like a lot, a lot to do. Yeah.

Did you, is it, you mentioned that like reflecting back at Teachable, talk to me about leaving Teachable and specifically also like, you know, the player coach aspect. Did you already have that at that moment as well, do you think? Or has that also developed over time?

That's definitely developed over time. So, you know, year 5 into Teachable, I kind of felt like, hey, I'm, one, I'm like, I'm fairly burnt out actually. And I feel like this company probably deserves like a more experienced head of product. Than I was back then, though Ankur was super generous to give me that role. And I really felt— I actually really wanted the company to do well. Honestly, it was like, like, I feel like I'm not getting something right here that the company deserves, right? So that was one factor. But then there was a sense of, hey, like, but I've been trusted to do this job. And so I'm going to let my boss down if I go to him and I'm like, hey, I feel I'm leaving, right? But So this is a funny tangent, but essentially at one point I make a trip to London for like a day. Yeah, right. And so because I'm like, so like it's like learned helplessness, right? You're like, I can't change anything. I can't even quit. I'm stuck. So I go to London for a day. I meet with an old friend. We just walk around London. We're not talking about any of this stuff. I come back and I'm just— I'm in this like very different mindset. And so that Monday I remember being like, okay, like we'll figure it out, but I just have to like tell Ankur like, I'm leaving. Yeah, right. And I want to cooperate with everything. I'll help like find my successor if I have to, like, you know, do the knowledge handoffs or whatever. But I just kind of have to do that. And so that Monday I came back from that trip and I was like, all right, I'm leaving. Back then I didn't have like a true backup plan or anything, but it was just this instinct to be like, I think now's the time. And then also this feeling of like, I know enough people by now and have enough experiences where actually, like, I think I want to start my own thing and I don't want to be like just another, like, head of product. Not that there's anything wrong with heads of product, but it's like, that's not why I moved to America in the first place. And so there's something in my brain being like, now's the time to like actually go do it.

Yeah, that's scary though, that conversation, because you— I'm sure, you know, you probably were building that feeling up over time. And it's probably that trip that forced you like, okay, now I'm actually gonna—

Oh, it was very scary. And it was sad, honestly, because, you know, I had that conversation. I remember at the end of the day, so Ankur and I and my co-founder now, Andy, we would like go to a bar after most workdays. And that was our way to like debrief and kind of learn from each other and share news and stuff. And so that evening, I remember being at the bar and like, and it was like, it was kind of the three of us, we felt like we were in the trenches, right? Says running product and he's running growth. And it was like, oh, like I'm letting these guys down. And there's a feeling of like sadness and having let them down. And yeah, that was really tough, honestly. But also feeling of like, man, if I can come out of this and like start my own company, like Ankur's the guy like I actually want to like support from and like he might even fund it. And so there's also a feeling of like I don't think our journey ends here, but this is the next step that I, that I kind of just have to take at this point.

Yeah, I think it's interesting that you felt so strongly and then, you know, you don't immediately go and build Circle. It's not like, okay, I've, you know, we found my successor, I leave next day, I'm starting Circle. And so you have this really strong urge to do so, but you're still patient enough in finding what it was. Can you tell me about, you know, those couple of months in the wilderness, if you will, and then the early days of Circle, because I think it's really interesting that you were so intentional yet still patient enough to find the right idea and the right co-founders.

Yeah, so I end up leaving, you know, mid-2019. And at this point, actually, I was very lucky to have a friend named Sahil Lavingia, who runs Gumroad. And actually, he's basically my age. And we were also like teenage programmers. So like, we've known each other since we were kids, like 15, 16. And, you know, I was talking to him and he basically offered me a contract gig at Gumroad because remember, I had like, I had a daughter, I had like massive debt. Yeah, I still needed to like earn something, right? So that, that kind of became like my cushion, right? So it's like, okay, well, I can contract for Gumroad for 3 days a week as an engineer, designer, and then work on my own ideas 2 days a week. So that was super helpful.. And then in those 2 days, what happened was I ended up reconnecting with Rudy, the guy from Australia I met in Australia. And actually Rudy had also like flown out to New York and worked for Teachable for a few months. And so he'd become— so he'd built our marketing site. He'd then become a consultant, like almost like a fractional CTO to like 30 course creators. So while I was VP of product, he was kind of on the other side, like helping those guys. So we would like often exchange notes about what these guys needed. Yeah. And so I was like, hey, Rudy, like, why don't we do like a vacation? Like, bring your fiancée. I'll bring my wife and daughter in Portugal. Let's shoot the shit. Let's like jam. Let's talk about ideas. So booked a vacation in Portugal. And, you know, essentially we'd— so we'd have these like very, very cool nights, like sitting out on the balcony, looking up at the stars in Portugal, being like, man, like, we want to build something. And there's something here about like the creator space that's so inspiring. That's like to build software for people who then go on to start businesses and become millionaires. Like that just felt to me, and it still does, like the most fulfilling thing that I could do versus building like super consumer apps or super enterprise apps. Right. So it's like there's got to be something in this space akin to Teachable and Shopify that could be built. So we just, we'd stay up all night while our wives and fiancées were asleep and we talk ideas. And one of these ideas happened to be around like the idea of community. I don't think we were so concrete as to be like, we're starting Circle, right? But it was like, there's something about the community thing because what a lot of these entrepreneurs want actually is like they want constant engagement from their audience. And so when they launch like online courses, they basically don't like— they, they don't really have a business until they engage an audience. Right. And they don't get to keep doing what they're doing until they like do it for a long time. Right. And so there's a very like vague intuition of like there's something about the community thing, something about the engagement thing That's here. I remember that night we shook hands. We were like, all right, we're doing this.

Yeah.

In Portugal. And we then kind of had this routine of basically for the 2 days a week, Rudy then also contracted for Gumroad. So we had the same routine. But for those 2 days, we would just get on a Zoom call and we just talk for like 10 hours about all sorts of ideas in this ecosystem. So everything from like banking for creators to like a website builder to like, you know, definitely spoke about community. Another course platform is just— we just circle all these ideas. There's an idea that we were very excited about with a terrible name called Upfront, which is basically the idea of, hey, imagine if someone shows up and you could be like, okay, you have an audience or you have knowledge and we can help you be an entrepreneur. Like, what would that app look like? Yeah. And long story short, one of these ideas we kept coming back to was like the community thing, right? So we then dug into like your Slack, Discord discourse back then and eventually became convinced to be like, actually think there's something way bigger here of like if we can build the ultimate platform for communities. Yeah, like that could be like a Shopify-scale business because over time what's going to matter on the internet for all these entrepreneurs is like selling belonging, selling learning.

Yeah.

Through the internet. And there's still no platform that's actually like hit out of the park.

Does all of them at the same time. Is that also then how you built the product strategy and the product vision is from that sort of like what should exist and how can we combine, you know, these needs of these, these entrepreneurs?

Yeah. So, so what really helped actually was like, so I had all of these Teachable customers like Tiago Forte. Yeah. Who offered to hop on just open-ended calls. It's again like the head of product type thing, right? It's like, hey, like, I don't know what I'm doing. I just want to learn. I just want to talk to you and learn. So like he would then screen share and he'd be like, let me show you my course stack.

Yeah.

Let me show you how I like edit my videos or whatever. And I'd get inspired from that. And one of those conversations I showed him like the mockups of Circle, the one, and he was like, oh dude, We're running a cohort. I hate Slack. We would run the next cohort off you. And I was like, oh, cool, it's working. If you run it, I will build it. Yeah. And Rudy at the same time had this— had very similar conversations with his clients who basically offered the same thing. It's like, yeah, sure, if you're building it, like, we'll trust you to run like a cohort or like have like a second community which we could then transfer people over to. So we had very generous, like, I think our first 10 customers, like truly a bet on like the founder. Clearly there's no product. Yeah. And so I still joke with our sales team that I like back then, like we sold like initially we were selling no products, we were selling like Figma mockups, but then we were selling like posts and comments. Like the entire product was just like a Facebook group. It was like posts and comments.

That's amazing. Is— do you think what's, what's the significance of like having some of those anchor early customers? Because, you know, he's still with you till this day.

Yeah.

What's the importance of a startup like that, you know, developing this product around these early customers?

I mean, it's everything, right? So one, it's the accountability, right? You make a commitment to someone like a Tiago and you're like, oh my God, if Tiago is going to use this thing, like with his audience and he's trusting me with that, this thing better work well. So I'm going to like really dig in to make it work. And we had that experience with all of our like first 10 or so customers. So the trust and like they had my phone number, they had Rudy's phone number, they could like literally text us or Slack us at any time. And then just the feedback, right? The learning loop of like, I still remember one of my closest friends now, Will Mannen, was actually running Thiago's community and he would send us like basically daily Loom video with feedback as he was launching Thiago's cohort. And we would, we would then action that feedback. And that routine then turned into like basically having a waitlist when I shared that I'm working on Circle. Yep. And, you know, basically sharing that like, yeah, I'm building this company and we need users. So please join the waitlist. And through that process in the private beta phase, reaching out to like, I don't know, 10 or so people a day, hopping on demos. So I did like 5 to 10 demos every morning, get the feedback or like learn about what people needed for us to close the deal, then spend the next like 5 to 8 hours coding and then end the day like clearing the support inbox. Rinse and repeat for like a year while we were in private beta.

That's insane. And once you guys, you know, during this time, the product's obviously getting much better. When do you decide it's time to raise money?

So thankfully, this happened actually very soon. So, you know, while I was— the first thing we did was build this like very basic like prototype. Figma mockup. Yeah. That turned into like a, you know, a very basic product based on a hackathon that Rudy and I did in Los Angeles. So actually, at this point, we'd also convinced Andy, from Teachable to join us as a co-founder. But he didn't have anything to sell. So he's a growth marketing guy until we had the product, right? So for a few months, like, why don't you guys build the product? And then, you know, then I'll start. And so we built this like prototype over a week in LA, rented an Airbnb. I had to get away from like the wife and kids to like be super focused, right? And I sent a link of that product to Ankur. And to Conrad, Teachable's co-founder. And they were both like, hey dude, you should, you should do this. Like, and Ankur was like, count me in for $250K first check. Conrad, $100K. I think they committed actually basically the same day. And it was like, whoa, like, man, maybe I don't have to do the contracting thing. But I was like, there's something nice about like having the comfort of the contracting gig and working on this for 2 days a week. But I remember them giving me the advice of being like, no, like, you got to go all in. Yeah. Like, if you're doing this, if we're funding you, like, you got to go all in on this. And this is— this could be another tangent, but I'll give you like the high-level details of how I raised our first funding round, which is Thiago actually introduced me to a guy in New York. His name is Brian Tobol. He's a serial founder. And so him and I just met, just by the way, he gave no context. So another one of these like random meetings at a bar drinking Old Fashioneds. And I pitched him the idea and he was like, yeah, you have to like raise, like this idea is so good that you got to like raise and raise like $1.5 million. And I was like, maybe you just need like $500K, like, because these guys are already giving me like $350K. And he's like, no, like do $1 million, ideally $1.5 million. I'm going to intro you to like every VC. In New York tomorrow, you're going to crush it. You already have like the track record and all that. And he's the one honestly who made me kind of see like the potential of like raising the round and kind of going all in. And, you know, next day there's no emails. But the day after that, there's like 10 emails in my inbox, an intro to like every seed investor in New York and ended up having a great chat with this guy named Nicholas Shirls, who runs Asylum Fund now. Back then, ran Notation Capital, who essentially offered to like take the whole round. So we raised $1.5 million within like, within 2 weeks of meeting this guy Brian. So it's funny how it works out with like Tiago as a Teachable customer, Tiago as a Circle customer, to that random intro, to this meeting with Nick. And then within like 2 weeks of that, we have this round closed with like 10+ angel investors.

Yeah. It's insane how quickly you go from closing the round and then, you know, getting customers. And I feel like this is where things start iterating much more, much quicker. Um, you know, you've closed round, you know, there's still a lot of work to be done, and now, you know, you're sort of opening up this bigger vision. What was sort of the process in the months or, you know, weeks afterwards where you've gotten this capital?

Um, so process was, okay, now we have like a million and a half, and we have like, okay, between three of us, we have like years of runway actually, because we weren't paying ourselves much. But it was like, okay, well, I don't just want to build this myself. I also like, I knew by then, like very clearly my limitations as a programmer, as a Drudy. So we're like, let's hire like the first couple developers, let's hire someone on support, which means, hey, at least I don't have to do like all the support tickets, we could just divide and conquer between me and the support hire who then, by the way, is still our head of support. She now runs a 30-person team.

Yeah.

Um, under CX. Um, so her name's Keisha. Um, but yeah, it was like the simple, like, early hires of, like, hiring engineers, first support person. Andy was still the only, um, go-to-market person. And a deal I had with him was, because I knew how good he is, like, as a marketer, uh, and as a salesperson, right? And the deal is like, dude, we're not going to fake our way to product-market fit. Like, I know you can do it. I know you can grow pretty much anything. But for the first year, we're going to go through the hardship and just put in the grind of like 5 to 10 demo calls a day. And remember, it wasn't just me, right? It was like it was Andy, it was Rudy as well. And we're going to take all that feedback. We're going to build an amazing product that grows organically. And then maybe in year 2, we're going to have a sales, marketing, customer success team. So for the first year and a half, I think we just had Andy doing like all of GTM and Rudy and I just doing all of, you know, product and engine. I was doing all the like ops and culture and HR and vision setting and all that. And that was the deal. And it really worked out because we, you know, we launched publicly in September of 2020 after maybe 9 months in like private beta. Shot straight up from like $200K in ARR, having done like the onboarding, like founder onboarding, like sales demos to like opening up the floodgates to like $1 million in ARR within 3 months.

Yeah.

That's about when we closed our seed round, which was, I think, $4 million round at a $40 mil valuation.

Yeah. That's insane. It's insane how quick it goes from here as well. And I think it's very interesting. When did you get that? Like, when did you realize, okay, we do need to start building out the GTM function outside of just, you know, the original team? Like, what, what made you feel like you were ready for that? Because I feel like it's very unusual, uh, especially if you're growing so quickly, to be like, hey, let's actually pull off the gas a little bit and be a little bit more thoughtful about building the product.

Yeah, so I think, um, maybe after year 1, it was like, well, Andy's doing a ton of demos because, by the way, at this point it was like, hey, like Rudy and I cannot do all the demos. We're like building product. There's so much product to build. Andy, you do the demos, right? So at some point he's just doing the demos like himself.

Yeah.

And just to free up his time, we're like, maybe we need like, like one account executive, right? So we thought pretty small actually. We didn't even have marketing. It was like one AE. So like one guy, again, if Andy could split the demos with an AE or two, that would help. Right. And, you know, we had this very simple model, by the way. I love like simple models. And sometimes I'm like, man, remember the days of like just having a very simple spreadsheet where Andy and I would just look at it and be like, okay, well, here's the growth targets, here's the number of demos, here's like our runway, here's our burn rate. That's all that mattered.

Yeah.

And then after we hit $1 million in ARR though, so end of 2020, we're at $1 million. We forecasted out, we're like, pretty sure we can grow this to like 3 to 4 million in ARR. But we're not going to do it unless, unless we like hire some GTM folks. So that led to like initially hires, and then that led to us realizing that no, actually, like, we should probably just hire a very experienced like head of sales, a head of customer success, wasn't quite yet a head of marketing. That still took like a year after that. But at least on sales and customer success, it was like basically by the end of 2021. So a year after that, we had a very experienced head of sales who was actually a Circle customer and a very experienced head of sales.

That's awesome.

Which really helped. And then Andy could hand off like the demo part to him and then focus on building the rest of the GTM org. In the meantime, I was building our leadership team and our eng org. So by the end of 2021, we might have had like 30 to 40 team members, maybe like 10 to 15-ish devs. And all the leaders started emerging, right? The head of finance, head of people operations, promoted Keisha to head of support and also started forming our dev team. So I knew, by the way, Teachable days of like not scaling like monolithic with like just one giant team working on whatever. So by the time we had our like 6th or 7th engineer, we knew, okay, like this person's just going to focus on building out a payments team and then turn into like livestreams and courses and mobile. So iOS, Android, and so on.

Like product function specific teams.

And right. And what's crazy, by the way, is like all of those in like ICs that we hired, like the person who built our initial like payments codebase now leads a payments team of like 10+ people. The same is true for the person who built our live codebase and for like 4 other people like our iOS person, Android person. They're all like leaders now and they built the thing from scratch. Yeah.

That's insane. Well, okay, well, so tell me about scaling then from this point in time, because it's end of 2021, your revenue is scaled a ton too, and by this point you've raised, you know, another $25 million. How do you make sure the organization— you said you love simplicity and you want to go back to those days of the spreadsheet. How do you make sure as these teams are scaling, as these people are scaling in terms of what they need to do and how many people they need to manage, how do you make sure that simplicity is really kept and the focus is, you know, still kept that you're rolling in the same direction?

Yeah, I have very complex feelings about this.

Okay.

So I think the ship for like sheer simplicity has sailed. And not just for us, I think it tends to sail for like most companies which are in hyperscale mode, like you have to accept some level of complexity. But I think what you trade that off for is clarity and cohesion. So what I'm about now is not quite like keeping things simple and like, oh, we can just show up and have a grand old time and have fun. Like, that's not the goal. But the goal is like, can we as a 200-person team today have a ton of clarity top down on our vision, on our values? Everyone knows like why we're doing what we're doing, what the strategy is, etc. And then can we translate that to cohesion? As a company so that everyone's giving it their best with a ton of autonomy, right? So no one's being like micromanaged and like handheld. And basically where that comes from, I realized is like it's very top-down, right? So Andy, Rudy, and I meet every week. We call it our weekly board meeting, right? We spend basically 2 hours talking about every aspect of the business that needs our attention. We translate those discussions to thoughts that we share with our teammates. There's a lot of memo writing that I do, so I love memos. You know, the Bezos kind of crisp memo thing is something I'm a big fan of.

Yeah.

So I'm basically writing like a memo a week at this, at this point. And I love that as a way to be like very clear and concise with my thinking.. And I think our team members like it too, to be like, hey, like, I don't want to hear like Sid ramble. I want to hear like the 5 bullet points that actually like truly matter. Right. And they don't have to fully accept it, right? They could push back or they could give their own like 2 cents. But that really helps. We have a founder pact between the 3 of us, which developed after like, you know, first couple of years of not aligning on certain things. We've never had a fight, honestly, but it was more like not making the right hire and being like, oh, like, I don't know if we're all on the same page. And so we developed this founder pact, this like private talk between the three of us to be like, here's how we work together, here's how we resolve conflicts. Thankfully, we haven't had a single argument since.

But if you— yeah, that's amazing.

But yeah, you kind of need to now develop like these systems, right? And so it's like, it's basically all about like filtering down clarity in a world that's very dynamic. So it's not just like, hey, there's a set vision and we're just doing that vision, right? It's like the vision evolves, the vision changes. Maybe in a certain year, like we're more focused on this aspect of the vision versus that aspect of the vision. And I'll give you a great example. You know, we became profitable 3 months ago, which is a big milestone. But that, that goal was actually set 18 months in advance. So in 2023, I remember like the VC ecosystem just being very down overall, right? It was like, oh, no startup's ever going to raise a Series B again, it seems. So set a loose mandate to be like, hey, we got to get profitable by like early to mid 2025. So all our models then just forecasted out to profitability. Our hiring plans changed. Our revenue goals changed. But the goal was also we have to grow as fast as possible. So it's not just become profitable.

It's like, how do you maintain those in balance?

Let's 2x every year. And thankfully we did 2x last year and the year before, roughly 2x while becoming profitable. It was just like mega hard goal, but I said in advance. And so what I'd remind people is like, look, I'm not talking about getting profitable like next quarter. I'm talking about getting profitable in like a year and a half. Yeah. Which is totally doable because like all our models kind of point in that direction if we make a certain set of trade-offs. And so the metric we focused on a lot is the rule of 40.

Okay.

Circle now operates at a rule of 50 plus. Back then we were rule of 30. And so it's a great measure of like basically the trade-off between your growth rate. Yeah. And your operating margin. And so the reason it's 40 is if you're at 40, it's like you're making the right trade-off. So either you should have like super high growth and crappy operating margin or have great operating margin and like super low growth, but you'd have to have like exceptional operating margin. But even there, there's like a minimum threshold.

Yeah.

But ideal, it's like the balance.

Yeah.

That everyone strives for, right? So it's these like goals that you have to introduce with a long time horizon for everyone to get to the— get the memo to be like, okay, well, that's what we're working towards. Yeah, be very clear about it. Be very clear about the why, which is like, hey, we're actually going to be like, we're doing this because we want to own our destiny. We don't want to be on the VC hamster wheel forever. And hey, guess what? If we accomplish this, there's nothing stopping us from like a billion ARR, like funded by our profits. And wouldn't that be super, super cool? Yeah.

Walk me through that decision. And then specifically, you've talked about those memos, you know, being inspired by Jeff Bezos and Amazon. Like, walk me through what the memos look like whilst you guys were sort of steering the ship towards that 18-month profitability goal.

Yeah, I actually don't like to have a set format for the memo. I've tried in the past to be like, okay, this, this is Amazon's format. Yeah. I actually find it to be more of an artistic thing of like, I'll just sit down and I'll have this like thought. So I remember the profitability memo was like, let's get default life, like the title of that memo, right? Or AI memo recently was AI or die, right? So I like to come up with a title that's like very direct. Yeah. By the way, another one was we have this plan called Circle Plus. It's our highest tier plan. Which wasn't working out for some time, is now crushing it. And so that was like, let's make Circle+ great again, right? So you start with the title and why is that so important?

Why is starting with such a concise and clear title important to you?

I think you kind of have to make the point with the title because most people I found sadly, like, aren't going to read the whole thing. So like, if they could read just one sentence, it's like, what do you want them to get out of that?

Right.

It can be something boring so ideally it's like—

AI or die!

It catches you right? So like "AI or Die!" It's not like, you know, "AI synergies." Like it's like—

Read this.

Let's get Default alive is like that's the goal, right? And so these memos I think it's a lot of kind of me, I just start writing like I start with generally like context love for people to know the why behind any of these decisions, right? It's like, hey, here's kind of where I'm seeing the market or where I'm seeing things headed. If we don't do this, there's always a point in the memo, by the way, where it's like, if we don't do this, we're long-term screwed.

Always.

There's always like that part. But then there's like, but here's what doing it could look like. Right. And so you lay out like the steps and all the trade-offs or the hard decisions. And then you end with the reward, right? Which is like, guess what, guys? Once we achieve this, here's the type of company that you'd be working for, that I'd be working for. Here's what happens to potentially our multiple or valuation or, you know, if we ever raise or sell the company or whatever, like here's like kind of the goldmine at the end of it. Yeah. But it's— but then it's like, it's not going to be easy. You know, you're like, you kind of have to set the right expectations, right? And then I love the longer time horizon thing. So I don't like memos which are like, this is what we're doing next week, next quarter, or next week. I like memos which are a little more like, this is where things are headed and we kind of need to change the trajectory of our company to head there.

Yeah, that's interesting that you talk about like these long-term goals and this really clear expectation setting of like, hey, this is what it's going to cost. This is why we need to do it. Can you tell me, I love how you also have investor updates frequent ones. Um, and I think your level of internal clarity and internal sort of long-term thinking and communication, I think that translates really nicely into how you communicate to your, your investor base. Can you talk a little bit about the similarities there and why that's also really important to, to do?

Yeah. Um, so I've written a monthly investor update basically from month one when I onboarded Tiago in January 2020.

Yeah.

Right. So that's 5+ years of, um, investor updates every month. I used to write them for our investors. Now the investors obviously still on the list, but I write them for employees actually, because there's way more employees now, like 200+ than investors on our cap table. And I find that to be such a clarifying thing. Like, I, I'm not a fan of like, here's what I'm telling employees and here's what I'm telling the investors. Like, I like to have very simple, cohesive update on here's how the business is doing. It's super honest, super transparent. Here's the wins. Maybe sometimes here's like something that didn't go right or that we were expecting to go better. And just that consistency. Right. And it's very like meditative for me. Like, you know, every— these days I send it out on the second of the month to give our finance team the opportunity to close the numbers. So it's not just me like taking figures from our bank accounts and stuff.

Just a screenshot.

Yeah. Yeah, there's a lot of like math behind it now because of how complex the business is. But yes, it's a very meditative thing of like, I sit down, I'm like brutally honest in the investor updates of like the, the one key thing I need to communicate. Also, like a lot of it is just celebrating people's hard work and wins and send it out, go for a nice like cold plunge, kind of meditate on the month past. And that's turned into a bit of a ritual.

Interesting.

And the employees love it, by the way. Like, they love the investor updates at this point. I feel like they kind of know, like, what to expect, when to expect it.

Yeah.

And I try not to BS in those. It's like, it's just the stuff that everyone needs to hear about us right now.

Yeah. What's like, have there been any moments of feedback from employees specifically where you're like, wow, I didn't realize that's how this impacted someone or how they interpreted this, like, in a positive way?

Oh yeah, many. I mean, when we set the profitability goal, we introduced a countdown in our investor update in the metrics section, right? Months to profitability. And actually, it just— it didn't just have the number of months, it had like the date. So like, we are expecting to be profitable in like June 2025. For many months I'd used to say that, right? We thankfully, by the way, like beat that and got profitable in April. But I remember like I'd get a question once in a while when that goal shifted a little bit and it would only shift by like, let's say 1 or 2 months. Someone would reach out to me like, hey Sid, just curious, like why, why are we not expecting to be profitable in like June? Like you, like you said or whatever, has something changed or like, are we burning more or whatever? And so it's that kind of attentiveness to like little like details where I'm like, whoa, like this stuff actually matters.

Yeah.

And then the reward is like when you celebrate a good month, like the month that we became profitable or like the way we ended last year having like nearly doubled, it's like, it's so rewarding because like everyone's been following that journey. Yeah. And, you know, I just sent out our most recent update yesterday and it's like, hey, now I'm reporting like free cash flow figures. And so now I'm hearing from investors being like, holy crap. Like, I still remember you being like, oh yeah, in a few months, you know, we're going to get profitable. And now you have like money showing up and like free cash flow. So it's a cool way to like have a very transparent narrative, keep yourself accountable, be very simple in your messaging and not make things too complex. And it's like a forcing function to do that.

I mean, you can't now stop. No. Like you have this level of transparency. You're communicating so clearly. If you stopped, it's like there's a clear correlation that's between Okay, the strategy of the business is probably a little bit too blurry, right? Do you ever worry? Like, are you just so— it's so clear the road ahead where you're like, I just know that what we're going to do for the next like 2, 3, 4 years. Or is there any moment in time we're like, okay, we need to really hunker down and rethink the strategy or direction we're going in?

I think we're constantly revising our strategy. So as I said, we have weekly board meetings.

Yeah.

Because the founders are just we are the board. So like we're very, very actively calibrating the strategy. Yeah, right. And informing people of that. So that's not something I worry about too much about communicating. I mean, like I'd say the very long-term strategy is still roughly like very similar to what we started with, but something details to be like, hey, actually this quarter, like this matters more than this other thing that I said mattered like a year ago or whatever, right? So there's a definite need for recalibration. But I'd hate to be in the position where I'm ever having to communicate like a major strategy update, because that means we haven't been dynamic enough and real-time enough when the strategy shifts needed to occur. Yeah. What I prefer are just more like micro shifts, right? So it's not like, I mean, the AI or DAI was maybe the closest we came to like, yeah, this really matters. But that was like months after, like we were working on plenty of AI projects, but it was like, hey, I need to kind of deliver this message to the entire team to be like, the world is changing, we need to adapt. And it's not just a nice-to-have thing. It's like a long-term existential thing.

Right.

And everyone has a part to play. Right. And there's like, you know, we did like process mapping at our offsites. We came up with a list of agents and it was a very kind of cohesive memo. It was actually very actionable. Yeah, I basically took like a month to write that memo because we were doing this stuff in advance. But yeah, that was the last time I think of like it being like a major thing, like, hey, this has to happen, right?

Ideally, it's still a little bit of a shift that you guys did. It's not like, oh, by the way, now drop everything you're doing. We have to change how we're doing it. So you're already on these projects.

Totally. And even with that, we emphasize like, I think a lot of AI memos emphasize like efficiency. Which I think is just the wrong way to look at it. It's not like there's a fixed amount of work happening and the goal is to get the AI to do that work instead of humans. I don't think that's how the world works. That's not how business works. Yeah, I think it's more like there's a dynamically shifting environment where everyone's going to be using AI to some degree. Obviously, the newer teammates will— or the newer companies will use it more than the older ones. And to keep up with that, we need to not just use AI, we need to use AI to deliver better experiences, increase the quality of the product, make things better for our customers. And ideally, actually, customers should never notice that we're using AI for anything, right? A customer should just be like, holy crap, like Circle is just getting way better and they're shipping so much and it's all super high quality. Yeah. And so I had to drill in that point only to emphasize that it's not about swapping your jobs with AI and like delegating that work and then like I don't know, working 4 days a week. It's about shipping a better product because in this rapidly changing environment, we're going to be competing with a ton of AI leveraged products. Ours just needs to be the best one. And so for that, it's not drop everything you're doing. It's a little more like be very intentional and thoughtful about how you're leveraging AI, how you can use it to improve the quality of what you're doing and have like a long-term arc that gets you to, okay, like these parts have been delegated, these parts are very enhanced thanks to AI. And then maybe there's always going to be some parts that are like human-centric. There's always going to be humans in the loop.

Yeah.

And so it's a very like realist take that I was proud of taking.

Yeah, I like that. I think that's not the take you see frequently, even from companies that are AI-first, so to say. Um, it's not the idea of we can just leverage this to be better for the customer, um, but it's maybe a little bit more like, hey, let's just make the AI more core to the product, or like, let's focus more on delegating more work and that's it. How do you, as a leader in your executive team, like, sort of distill that message from the top down, uh, to make sure that's like actually the focus? Because I feel like that's very unique, um, in the messaging from AI or Die, which most people don't, you know, think about?

Yeah. So what we did for this one is, so I had a draft memo which I didn't share with anyone except my co-founders, right? Yeah. And this is like, hey, vaguely speaking, these are the principles, what I just mentioned to you, right? It's like quality matters. It's not just about efficiency, et cetera. Um, and, but all of this is long-term existential. Um, and then, so we do like 2 company retreats a year. We're a remote international company. We have over 200 members in over 30 countries. So at our most recent retreat in Spain, yeah, earlier this year, um, we essentially held a leadership session with each of the teams per day and the founders, where essentially the founders gave like the team leaders— so imagine like it's not just the head of sales, but it's like 2 or 3 people who are also the sales managers, and same thing for customer success and marketing and other teams. And the idea with this was like, we need to get them in a room and we need to first communicate like what we're observing at a very high level of all the AI stuff. Like just we're technical people, we're following all this stuff. Others may not be as technical or as like, you know, tech, like grounded, right? So there's like a part of like imparting like, like what, like what is an agent? Like, like the one-on-one stuff.. And then from them, what we expected is a process map. So like, walk us through how stuff works right now in your org. So like, from the customer's perspective, like, what is the first thing that happens when they sign up to Circle? And let's say they write their first customer ticket, right? And so you just take the CX angle of like, when they write support tickets, or why do they even write support tickets, and you just dig in, and you have this process map. For, let's say, customer support. We did that for the entire company, for all the teams. And then we could look at that process map and say, okay, well, you know, what we could do is like actually build an agent for this step. So like the sales team could build an SDR agent that scouted leads and reached out to them on our behalf instead of like having real SDRs do that. So that's a real agent that we built and is working super well. We don't have SDRs anymore. The SDRs have been promoted to AEs and retrained. That's awesome. Right. So but imagine that example for all the teams.

Yeah.

Right. And so we have this now, this list of agents, some that are way more practical to do now versus later and some that like, hey, we should just hold, hold back on. It's like that's a pipe dream. Like, I don't know, like the concept of a CSM clone that you can talk to. I'm sure it'll be possible at some point, but not just yet. But let's not even focus on that. Let's focus maybe for now for CS. I remember realizing as they walked us through the process map. Oh, it's mostly about call prep and post-call action, like basically customer success people and a lot of salespeople. Like, that's what they do.

Yeah, right.

So, okay, can we make a call prep agent such that I came up with the hangover test of imagine you're hungover as a CSM, you, you like, you're late to work, you have a call, you rock up and you see this agent and it preps you on the call you're about to have. Like within a minute or two, and then you hop on and you seem super smart. Yeah, because the agent's giving you the full brief on, you know, what the customer has been up to and any issues they've had or any like points of expansion they could talk about, etc. And so it's like, okay, well, let's build a call prep agent and build that super well. So we had this list of agents and I have my chief of staff kind of call them our AISR administer that with people within those teams who we call agent builders. And so very practical, right? So now what I did after these like workshopping exercises and process mapping is I then turned that into a memo.

Okay.

So AI or Die, the first part is like the, the guiding principles.

Yeah.

For me, the second part is like, here's literally a list of all the agents we're building. Here's who's building them. Here's the quarter in which they're being built. And by the way, we're going to have a weekly update for all the agents, which my chief of staff will seek and then we'll share with the company. And we're going to have an AI Slack channel where everyone can talk about this stuff and we're going to celebrate the agent builders and we're going to make them feel like they're software developers because they are that important if they're building like a part of an entire function. Yeah, right. And so that then became the final memo, which is, I think, a good combination of like top-down and bottom up. Yeah. And very actionable. Now it's like, okay, now it's super clear. Like, this list of agents, here's who's building it. And then at our most recent all hands, we did a full review of here's all the agents that are like green, yellow, red. Here's what we learned. Here's what worked out. Here's what didn't work out.

Yeah.

And that's now like rinse and repeat for every quarter.

Yeah, that's beautiful. And now that's something that's key to the company culture. People are getting celebrated for building these things. Totally. Probably more people are coming up with ideas on agents to build, or that they're seeing things and opportunities that they otherwise might not have been thinking about. Absolutely. That's— I love that it's still repeated, and that it's like— that seems like a very hard balance to get from top-down and bottom-up, uh, you know, getting the right balance to make sure it's actually something sustainable within the company.

That's why you need a beautiful resort in Spain for people to call to, and then you kind of lure them in with like the, the beauty and Spanish wine and then you give them agents and, uh, you know, 100%, that's part of it. And probably one thing we learned, um, in, in the first quarter of doing this, right, is, um, it's actually not even just about like doing the work for each agent. It's actually more about impact. And so in the first quarter we emphasized like, hey, like just if you can build the agent, like great, we'll celebrate you. Yeah. Now it's not enough to build an agent. To be celebrated. It's like, what's the impact of the agent?

Wow.

So like the SDR agent, we have a shout out to Clinton from our team. Like he just shares like, like money numbers and like number of demo calls that the agent has produced basically every week. Yeah. Now we're looking at impact and now we're kind of treating the agent almost as an employee, like creating impact. And so the lesson there was, hey, like Now that we have a bunch of these agents, let's focus on adoption and impact. It's no longer just about the 0 to 1 thing.

Yeah.

And for maybe some of the agents that aren't working out, maybe we need to like go back to the drawing board and like rethink from first principles, like whether this agent even makes sense, or maybe there's some other part of the, the, the flow which we could semi-automate. So to take an example of customer support, like, is it more sensible to build an agent to help a CX team member respond to a ticket? Or is it better to have an essentially AI copilot in your product, which talks to the users and tries to help them on the fly before they even write a ticket? It's kind of the same knowledge. You're just solving for one upstream. Now we're doing both. We're trying to— we're actually starting to find a lot of success on the copilot. Really?

And so we're seeing a lot of testing this then with different sets of customer support issues or? Like, how are you determining which one's the right one to—

Oh, it's, it's, it's basically all anything that I can answer.

Okay.

And yeah, it actually, it deflects 80% of the tickets.

Geez.

So, so now when you reach out, it's like, okay, you can talk to someone, but we're going to try and help you.

Yeah.

And if you don't find that to be helpful, then you get the chance to have a live chat and then it's a full-on support ticket. Yeah.

Well, there's two questions I got from that. I have to say them so I don't forget, but we'll focus on one at a time. But how do you then retrain potentially the people who are no longer answering those support tickets would be one question I have. And then the second one, which we can get back to afterwards, is how do you decide what to build internally? Because there's a ton of companies— might be the most popular thing that AI companies are targeting is like, you know, customer support. So talk to me about retraining internally if needed at all. And then we'll talk about, you know, how do you decide what to build internally? Yeah.

So retraining actually hasn't been a problem for us because we were short-staffed on support to begin with and still are. It's just growing so quickly. But what it's meant actually is the support support team has relatively fewer tickets to answer, and at least not the basic ones. But ironically, the effect that it creates is like, well, all the easy tickets have been like deflected by the AI, and now the tickets that are coming in, when I look at it, I'm like, okay, clearly like a human needs like 5D.

Yeah.

Or maybe it's not even about like just like self-serve support. It's maybe like they just need to talk to someone about their business because we get a lot of these customers like launching new businesses, launching these communities where it's not about the product, right?

It's also advice.

It's a little more psychological. It's a little more like coaching-oriented sometimes. And so we're lucky/unlucky to like have that problem. But I do have a long-term solution to that. So what I've shared with our head of CX, Keisha, by the way, also our first team member, right? Yeah. Is I think the philosophy we should have long term. So long term, let's say it is possible, right? Well, guess who knows more about the product than anyone else? Our support team. They know more about the product than any other team in the company, right? Because they're dealing with issues like all the time, right?

Yeah.

What if we were to now leverage that knowledge to make the product better, to prevent a lot of these issues? Instead of simply like getting back to customer when they face the issue. So what about having some of them like become part of our dev teams, at least starting with like feedback sharing, but eventually even like, hey, that's the support liaison that represents the customer and everything, which is not even the PM, by the way. The PM might have like a vision or like the eng lead might have like their own strategy, right?, but the support person is like, no, like I know how a customer will respond to this copy that you guys are shipping and maybe you want to adjust it to say this instead. Like, I think there's plenty of opportunities like that long-term. Yeah. Um, I think in the short-term, honestly, there's going to be way more tickets than, than we would like, um, for them to take care of. And I think that's okay. Um, and what it does mean is our highest paying customers, our higher paying customers get really good support. Right? Because now these guys have the time to not be dealing with like simple stuff. So they could actually just go like really deep into like some high-end customer's issue and really give them like the best service, which otherwise wouldn't be possible.

Yeah, they just got a ton more time. I love that. When you mentioned bring support teams into like other functions of the organization, kind of reminds me a little bit of Stripe who like invite customers to their board meetings, you know, to make sure they're represented. I think that's maybe the way things are going to go for support in general long term.

That's awesome. One meta point about AI, by the way, I think it's that tacit knowledge that's going to be really hard to automate and solve for. So it's the knowledge that only a customer and a customer support person knows, right? It's the stuff that is when you're abstracted from like that specific instance, right? You're like, you're not thinking about like that very specific thing. Yeah, but that's knowledge. Yeah, right. So a support person might know like, oh, when customers ask for this toggle, actually what they want or what they're asking for is this other thing. Yeah, but for now they solve it in the product with this toggle. Yeah, right. But the customer may not ever express that to you, right? A customer is never like, hey guys, you should just build this instead of like me having turned on this toggle. I mean, some advanced customers do, but very not frequently do you get this like very pointed feedback, right? So it's that tacit knowledge, which I think even long term, like I'm not super, super bullish on AI solving for that because I just think it's a very experiential, it's very like multidimensional need that, that people have.

Yeah, it's not just like, here's the information of that the user is constrained by the UI and that's why they're making this decision.. And maybe to your point, like most of them aren't saying, oh, I'm only doing this because of X reason. Like you have to intuitively be very aware of why they're doing it and sort of the 2 or 3 dimensions behind that to understand, oh, they don't want to just press this button. They actually want to do XYZ thing, but this is just the only way to get there.

Totally. And you know, in our case, we have this very fairly complex product actually where we have 18,000 communities now serving 12 million members. Each of those communities. Yeah, that's crazy, right?

That's crazy.

Big number. That's a huge— Yeah.

After only a couple of years.

Yeah. I mean, when I compare that to like my Memari days or Rev2 days, it's like, oh my God, that's a different scale, right?

Yeah.

No, but one of the product philosophies we have for Circle is bring your vision to life, right? So our, our vision is like, hey, like we want to build a platform for you, much like a Shopify. Yeah. To show up and like, you tell us what you need. Or even better, like, you just work with the product on what you need. So if your community or course or events business needs XYZ features, if you need a website, you need email marketing, we have all of it. You might— you definitely don't need all of it, but we're here to give you the stuff that you need. So it's a very complex product. Yeah, right. And there's very different types of businesses that use Circle. Yeah. And even the member behavior is fairly complex. So the types of tickets we get, it's rarely ever like, oh, if we just solve this one issue, like it's going to help everyone. It's, it's more frequently like, okay, so this type of a customer who's building a like community-led business with us for this type of an audience would benefit from like these improvements. Yeah, right. So to take an example of like we're building breakout rooms with our live streaming tech and it's like there's so many ways you could build breakout rooms. We're not going to solve for all the needs. Yeah, but we have some sense of what our customers, or at least enough of them, need. And even then we're going to have disappointed customers being like, oh, like if you guys just had this like one toggle or like if you guys implemented this way, I could do so much more. And so that's a constant battle with us.

Yeah. I mean, how do you go about that battle, especially if you scaled with so many different types of users, so many different types of users with different levels of businesses themselves as well? How do you prioritize? I can imagine you guys get a ton of feature requests. How do you prioritize that with such a complex product? Because I imagine because of its complexity, it might be very easy to say we need this, we need that, we need everything if you're trying to satisfy every single user.

Totally. So one thing is my co-founder and I are super hands-on, so I still run product. So there's no head of product at Circle.

It's you. Yeah, that's what Brian Chesky says the founder should be.

So yeah, so I have like 14-ish direct reports. Half of them are like our business leaders, right? Head of finance, head of people ops, my co-founders, head of support. And the other half are our eng leaders who report directly to me. And so I, along with my co-founder Rudy, we're in like 14+ planning meetings, roadmap meetings every quarter. So first thing is like it's fairly top-down. From a like, this is the roadmap standpoint, but it's very bottoms up in the feedback standpoint. So actually one of the ways in which we use the AI is we now have these amazing feedback packages. So we had our chief of staff and someone work with him on preparing like a feedback package for each team, which looks at all the tickets in the area, looks at all the sales calls, looks at customer success feedback. We solicit subjective feedback from each team. So we ask each team like, What are the top 3 features you would want from Team X? Let's say it's payments or the live team. And so before these meetings, it's like we have this feedback report, we look through that, and then in the meeting it's very top down and that, hey, like, yep, we know like there's like 50 things that people want, but we're only going to work on these like, yeah, 10 to 15 things which we know is like super critical. And even within that, actually, like the must-ship priorities are like these like 3 things. So if some of these other things slip to next quarter, that's totally fine. We've been doing this, by the way, from basically month 1 at Circle. So Rudy and I would just used to do this like in the early days. So it's a system that I think our dev leads appreciate a lot because there's a lot of clarity, right? It's like as leads, you don't have to worry as much about the impact part. I always say like if the impact sucked, it's more on me. Not on the devs, right? You have to worry about the execution part, right? So if we have a roadmap, what we expect is for our teams to ship roughly 80% of the roadmap. It's never 100%, by the way, because you never want it to be like, then you're only shipping the roadmap and we're not listening to anything during the quarter, right? Um, so it's very top-down in some way, but it's also very bottoms-up in the execution. So we're not in like sprint meetings. We let each team like run their own like product processes. So some teams do biweekly sprints, other teams do daily standups, like we don't care. As long as you're shipping stuff and it's like, it's really good. And then from a vision cohesion perspective, what I think a lot about these days is the idea of like progressive disclosure. So the idea is like, okay, you have a complex product like Circle with like hundreds of features, right? Obviously, when someone joins, they don't need all of those features on day one, they need like a subset, So imagine like starting a new community or a course business. You just need like, like 3 to 5 things, right? The idea we have is, hey, like, what if the product could only serve you those things when you're starting out? We could have then our AI copilot work with you on giving you the rest as you need it. So at some point you're like, I want to start running events and it's like, oh, what types of events do you want to start running? And boom. So now you're kind of like, it feels a little more like vibe coding.

Yeah. Versus you're building your own circle app.

Yes. That's what we want the process to feel like. Yeah. And, you know, I give the example of vibe coding all the time because I love vibe coding. I'm building tools for myself all day. I just built like a headcount planner for the company and I'm like, yeah, I don't need to deal with like all the complexity that a vibe coding tool has to offer on day one. Yeah, I start telling it what it needs. It gives me that. Why doesn't Circle feel like that? So that's something we're working towards. And the insight there is the features are not the problem. Like, it's great to have a platform that can do everything because we want to be that one and only stack for every creator, right? Every business, every brand beyond like their social media presence. Right, right. We want one product that does like the website, email, community events, essentially everything, but you don't need all that day one.

No.

And you're going to expand into those things as you need it.

Yeah.

And then the act of expansion should feel more like you're just talking to the product and you're like, okay, now I need this. And even better, like it could help you plan an event, right? It could be like, oh, you're about to run a virtual Q&A using Circle livestreams. Well, here's the best practices to running such an event. Here's a potential agenda. We can make it super delightful. So that's kind of the vision of the product, honestly, is like, like making it feel like you're vibing with the product.

Yeah.

While the product expands with you. So you never have to be like, okay, now I want to run events or now I want to like have a group chat and then I need a different product.

Yeah.

Right. And then what's great for creators and members is it's one product. Like it's the home, right?

But it doesn't feel overwhelming because they're discovering it as they go along.

Yes.

That's interesting. Are you testing that already? Because I imagine conversion, if done correctly on that, theoretically should be a lot higher because you're serving them like, oh hey, you need events. Like that's part of this subscription. Like, oh, I need that right now. Like that's when I'd probably upgrade instead of being overwhelmed by all these options. What are your thoughts on like the conversion aspect of that discovery? Because I agree with you. I think a lot of apps should go that way. And I love— what did you call it? What was the term?

White coding?

No, no, the discovery, the preemptive, progressive disclosure. Progressive disclosure. I love that. Yeah, that's a beautiful term.

Yeah, we're not testing anything right now. So, and caveat with what I just laid out to you is the vision. It's not like Circle today. Yeah. Right. That's what we're working towards. We can watch this back in a couple of years and be like, yeah, but I feel comfortable kind of forecasting it because we're so like deep into this vision that it's like, it's, we're gonna do it. It might not work, but like, we're gonna do it. Yeah. And I think, yeah, we will have to be mindful of like, it's like, can you really predict what someone wants at any moment? And that's the bet we'd be making on the AI element, right? And obviously the nightmare scenario is like, well, now we've taken features away from their perspective and they don't have the thing that they need. Or maybe it's even like they don't know that something even exists to know to ask for it.

Right.

Whereas right now in the product, we kind of, you know, we have like landing pages for all the features that are possible. So there's definitely like, it's like tread with caution.

Yeah.

But I can see the vision like so clearly in my head of like, yeah, you like in the exact way that people vibe code apps, people should be vibe building businesses. Yeah, right. And we should have a product that goes layer beyond just the app element of what they're building with like business strategy, tips on like executing certain things, like growing your audience. Yeah, it should be that one like, like end-all product, which by the way is like it shares a lot of similarity to that Upfront idea that I told you about. Yeah. And Rudy and I talk about this all day, which is like, oh my God, it all just goes back to Upfront where like The idea is someone should be able to show up with their skills, audience, whatever, and launch a, and launch a great business. And the product helps them with that because the product guides them into success. Right.

That's so cool. I love that. Have you, you know, the company owner.com? Yeah. They've kind of done this a little bit recently where they have, you know, all the features for the restaurants, but now they've also got the AI element where it's like, hey, you know, you can actually increase your, your, your marketing, or like your conversion rates by just adding an extra email. And oh, that's okay, like we'll do all of that for you. But I love what you mentioned about it, it is that upfront vision really was like, just come on here, uh, help sort of steer the direction and we'll sort of guide you in what's possible when you need it.

Totally.

Do you think all— do you think a lot of businesses or a lot of B2B businesses are going to go in that direction the next couple of years, or do you think it's specific to something like Circle or Um, you know, I hope they do.

Um, I frankly don't hear enough about this idea.

Yeah.

Like this idea is just something that we've come up with as a solution to the complexity problem, right? Yeah. Because for years we thought, oh my God, like the product's getting super complex. There's so many features. People don't know what to do. And then thankfully AI happened and then thankfully vibe coding happened and now it's like, okay, well I kind of, I have an intuition of what it would feel like to use Circle in that way, right? Where it feels like you're just vibe building an entire business. I don't know the exact solution. There's definitely many memos to go around towards that vision. But I really like in the abstract at least, right? Like obviously you never know like on the execution details, but I know even like Shopify, for example, has Sidekick, which tries to do a version of this, but I think it's still fairly basic. Yeah. But in the abstract, I think the vision's like absolutely there.

Yeah. 100%. It makes sense. It's just too early probably right now.

Totally.

But it will get there. I want to ask you a couple like quickfire founder advice type questions, and I want to, you know, sort of go a little bit deeper on some of those. You're very like— all the memos you've talked about, AI or Die, preemptive disclosure, like these are all very concise, clear ideas with tactical things underneath them supporting them. I think you're And I admire this about you. I think you're a very strong communicator. Um, can you tell me a little bit about why that's important and how you hone that skill maybe as, as a founder and how that's evolved over time? I can imagine, you know, it maybe helped that you were a blogger, but you're probably a lot better than you were, uh, now than you were back then. Can you tell me about that specifically when it comes to being a founder?

Yeah. Uh, communication I think is like, is everything pretty much, uh, especially at the job that I do now. Um, by the way, I think I'm, I'm a decent like written communicator. I'm still working on like verbal communication.

I think you're crushing it so far.

Actively took a coaching session this morning and still honing that because I feel like, okay, that's like the next frontier for me to like really get better at. But yes, so I think on the written part, I think the issue is the following, right? Which is as you're scaling your company, you've got all these new people joining that have biases to their last company, right? And one bias I like I have to deal with the most is like people generally were not fans of the CEO in their last company. And so I have to do a lot to prove myself to be like, look, like I'm not like the others. Like you'd always reach out to me with feedback and all that, right? You know, all these people with like the lack of context. And now the question is, well, what are you going to do to align them? And then even over time, as they like really sink into the business, they want to give it their all. They just need to know from you, like, what are the boundaries and what's the vision and what are the guardrails and how will I know if I'm failing and all that. I think you have to get into like a writing practice. And for me, it's like I was thinking about this the other day. Like if I'm actually next to like a blank page, it's very hard for me to write.

Yeah.

So sometimes I can write a memo, but, but usually it's because I've already thought up the memo in my head for like days. And then I sit down to write. It's very easy for me to answer a question and then end up writing a memo to answer the question.

Interesting.

So what we do for all hands is, you know, we have like a quarterly all hands, lasts like 3+ hours. Every team presents. People generally love it, but we don't do a Q&A as part of the all hands. We do an async Q&A where the entire company can submit question async anonymously. Most of them are the ones that I tend to answer because it just kind of relates to stuff that I have stuff to do with, but not always. And in those async questions tend to be like pure gems, like prompts, right? It's kind of like you need the good prompts and oh my God, some of these questions. So in our most recent one, someone asked like, what is your definition of success in the next 10 years look like? And that got me thinking super deeply about it.

Yeah.

And essentially I ended up writing like, like I think it might have been like a 5,000-word essentially memo. To answer that question. Yeah. So, you know, when we do these Q&As, I love the format of an async Q&A. So one question in our last one was like, hey, how do you define success in the last or in the next 10 years? And I basically took that as a prompt and I started writing and ended up with like a 5,000-word memo in response to that. I just— I couldn't lie to that question, right? It's such a good and genuine question. Yeah. And so I went like just nuts, like thinking about like, yeah, well, what do the next 10 years look like for us? Right. But yeah, I think when you're writing memos, I think you can't underestimate like a good prompt. Also just Q&A, like love async Q&As as a way to source like what do people actually want to know? There's all this stuff that I could share, right? Some stuff I need to share because like the AR/DAI thing, it's like, well, that's more coming from me and no one needs to ask me a question, right? Other things might come more from like an idea or curiosity that an employee has, which could be expounded upon because I realized it's like, well, X% of our company just joined like, I don't know, like 3 months ago and they don't know any of this stuff. Right. And so they need that refresher.

Right.

So yeah. So I think, yeah, using these prompts, using it like the strategy of self-prompting to get yourself to write and to share are super important as you scale. And again, it goes back to the clarity and cohesion thing. It's like that's basically all that matters. And the more you're sharing— but, and it's not just brain dumping, right? It's like you really have to be concise.

Yeah.

And you have to get to like the heart of like what actually matters. So with the AI thing, I could tell people about AI all day, but actually the one thing I needed them to know is like It's the quality that matters, and AI alone will not get you to that quality. So counterintuitively, what I'm saying is the human-in-the-loop part of AI is actually super important. And I'm emphasizing that like repeatedly in every conversation I had.

Yeah.

And that just came from like I started having conversations and people kept thinking like, oh, is my job on the line? Like, what happens to me if AI takes over my job? And I had to specify that. I had to be like, no, like Actually, we'd be, and you'd be very fortunate if AI could take over your job, but we're like nowhere near, like, there's like so much work to do and it's not even, I don't even think it's like gonna take over a lot of these jobs.

That's fascinating. I love that so much that it's like the clarity part of that. It's like, no, it's, it's not about replacing your work. It's about enhancing the results and just using AI as a tool. Like that's the key thing. You're not getting replaced.

Totally.

Tell me in a quickfire way, what are some of the most important founder lessons you've learned over the last 5 years having started the company that's, you know, scaling incredibly quickly in a huge market? Like, you know, what can you tell other founders that are the most important things?

Yeah. So number one, I think it just goes back to the team and very specifically even like your co-founders and your leadership team. Because let's say if, if someone listening to the show is where I am and you're leading like 200-person company, well, guess what? You're not interacting with like 200 people all day, right? Most of your time is spent with, you know, your co-founders if you have any, your leadership team, maybe one level below that. And, you know, I have a— I do this thing where I have like an intro chat with all the new employees that join Circle. And I ask them like how they're feeling and stuff. And they generally say like, oh my God, it feels like the best job. I've ever had so far, blah, blah, blah. And I point them back to like, wow, like basically after the first 30 people, I haven't hired personally that many people at Circle. There's a few, right? But most of the hiring has been done by like people who I hired. And now it's like people who they hire.

Yeah, it's like a couple of degrees.

And I'm now talking to these people who've been hired by someone who I— who was hired by someone else who was hired by me.

Yeah.

And a lot of that credit goes to just the vision and values, the clarity, the team members that we hired. And so one, it's like value your team. It's probably lesson number one and set a good foundation, like share the vision and values, make sure they're bought into that and also be quick to like fire or part ways with people, give them great severance. Doesn't always work out. That's all good. Number two, I think like it's really the founder's energy, which I do think like runs the ship a lot of the times. And I don't just want to credit myself, but by that I also mean like my co-founders and all the founders, right? I don't know. There's something about when you're so deeply invested in a business like I am with Circle, like it's my life's work. I don't have company 2, 3, 4, 5. It's like Circle is what it is, right?

Yeah.

And I'm channeling all my energy into it. You know, it's my expression of like what I'm seeing in humanity and how we want to solve for it. Mm-hmm. That energy can never be let go or can never fade, right? Like, if your energy is all that matters, like, you have to be very intentional about how you, like, hone that energy, how you conserve that energy at times. So for me, it's like, it's habits like I cold plunge once a day, just got a sauna. So now I sauna and cold plunge once a day. I never want to rock up to Zoom call with a bad attitude. Yeah. Or like feeling like I want to rush it. So I'm very mindful of like my own mood. When we do these offsites, like, you know, we invite the entire company over, 200+ people now. We book out a resort or sometimes even resort and a half. And it's just all about energy exchange. And these offsites cost a lot of money. And what I tell our head of finance is like, yeah, there's no like clear metric to an offsite, but I can guarantee you the fact that if I ever— if we had to make an announcement to our employees and I just have to say, hey, we're doing one less offsite next year, like people would not be very happy. Right. And so how do you measure that? Like, what's the metric there? Right. Which goes back to the team thing. It's like because we value the team and we value this energy exchange, we're going to do the offsites. Yeah. And we're going to expect that things pay off in non-measurable ways. Yeah. And that's all that matters. So, so yeah, team energy, two key things. I think there's an element of also like sheer humility on the product front, like never feeling like, you know, your customers so well that like you have all the answers, like the world is so dynamic, like there's competitors that emerge every single day. I'm sure every single day our customers have thoughts about other things they could be doing instead of like running their Circle community, etc. Right? That's who you're competing with. That's what you're competing with. Expectations change. And so there's something about, you know, I love the movie There Will Be Blood.

Yeah.

You know, the first 10 minutes where he crawls out of the oil field and then like You know, like, I think he's like broken his arm or whatever. And like, he crawls his way back to his like township and like, he's clearly hurt, but he's like so damn happy because he's just discovered a new oil mine.

Yeah.

So my friend and I have this saying of, you know, we call it like touching the oil. Like at that point of the movie, at the start of the movie, he's like touching the oil.

Yeah.

At the end of the movie, he's clearly not touching the oil and he's gone like crazy. Yeah. Right. The goal is to be like Daniel Day-Lewis at the end of There Will Be Blood, but touching the oil. I think that's the entire goal. And touching the oil requires like humility.

Yeah.

Strength. It's like, hey, like, I actually don't know any better. I just have to be there by myself, like crawling through the mud if I have to, because things change.

Yeah.

So that's been like a key lesson for me. It's like, just like, remember to touch the oil, stay humble. Stay grounded. Yeah, because the world is super dynamic.

Yeah, I love that. Expectations change. Customers aren't always just thinking about using Circle. They might want to be doing other things outside with their business. I, I love that as a, as a thing to part and end the podcast on. So Sid Yadav, appreciate it, man.

Thank you so much for having me. This is super fun.

Yeah, this is awesome.