Teachable Employee to Circle CEO/Co-Founder— Sid Yadav's remarkable story

I was actually on the founding team of Teachable. To do what I want to do, having to leave the company for about 3 months, I did nothing.

You guys decide you want to start this other company and your biggest investor at that time are the people from Teachable.

At this point, he had basically invested 90% of his liquid net worth. So that's kind of how much he believed in me.

It's always a delight and pleasure for me to speak to CEOs because they get to see things from a very different level. And it's even better when they start out at the very early stages of a company so they can see all the different growth stages. And so that's why I'm super excited to be speaking to Sid. He's the co-founder and CEO of Circle, something that we use, full disclosure, a big fan of. You know, we use both Teachable, and there's some history there, and Circle, and we've seen it go through some growing pains and it's starting to get into a rhythm where I think it's actually very usable now. So Sid, for people who don't know who you are, Sid, can you please introduce yourself, give us a little background of your story, and then we can go from there.

Yeah, first off, thank you so much, Chris, for having me on the show. I mean, my co-founder and I talk about you guys using Circle. We're always like, Chris is the dream customer. So if we can make Chris happy, I know we're building a great product. So love how everything kind of is coming back full circle. So yeah, my name's Sid Yadav. I'm the co-founder and CEO of Circle. We're an all-in-one community platform for creators and brands. Started in 2019, now a team of— I think this month we're going to be 140. Wow. Yeah, yeah, it's been a, it's been a crazy few years, but it, it really feels like we're, we're just getting started.

Yeah. And so here's the interesting thing. So we can rewind the tape before I get into like what you're doing now, what you're seeing. Is we both have connection to Teachable. Like Teachable is the platform we use to host our courses and we love it. We just did an event with some of the team from Teachable. And you know, the funny thing is it never occurred to me, this is how smart I am. I was taping a TV show and they're like, this is a Teachable moment. I'm like, wait a minute, is that a plug? And I never realized Teachable is used in that way. I'm like, what a dummy. And I mentioned it to Olivia And she goes, "Yeah, duh, where have you been?" But it was just kind of neat for me to see like when a name can be used like that and so integrated into the conversation, super cool. So the question I have for you is this, is if I got my story right, you guys decide you want to start this other company and your biggest investor at that time are the people from Teachable, right? Did I get that part right?

Yeah, not only that, so I was actually on the founding team of Teachable. So I was the second engineer and first designer at Teachable. As was my, uh, uh, one of my co-founders was, uh, uh, Teachables, who actually went on to be, uh, Teachables VP of Growth and Marketing. So, you know, we saw that journey actually fairly up close and it, your, your story just made, made me think of, um, the, the moment where actually, so when I joined Teachable, we're not called Teachable, we're, we're called Fedora back then.

Oh, okay.

Terrible name. We all hated the name, including Ankur, the founder and CEO and my boss. And we were like, hey, Hey, this name needs a name change. And we went through these exercises we would do to come up with the name. Teachable was always my favorite name. And then people point out that a teachable moment is actually kind of negative. Like, you know, that's like a, you know, you, you're, you're being pointed out something that, um, that you didn't know before and it has a somewhat negative connotation. And I always looked at it as like, well, that's exactly the point because post the teachable moment, you're now enlightened. You now have a new insight. And yeah, so we had big debates about that actually. And in hindsight, just very glad we came up with that name.

Yeah, well, I've, you know, this is kind of interesting about perspective and lenses because I'm an instructor, a teacher. I've been doing this professionally for 15+ years. I'm also, I run my company and I believe the position of a CEO is one of a teacher. And we can get into the debate of that if you wish. But when we look at a bad situation happening, we lost a client, our servers crashed, there was a security patch that we didn't figure out, and so we're just really in a negative state. Then we ask ourselves, what is the teachable moment? How do we turn this disaster into a powerful lesson? And one of the things I love to share with people is failure is the tuition you pay for success. Like a lot of us have success and we're never quite sure what we did to reach this moment. Sometimes we think it's our talent, luck, timing, all these kinds of things. But when we fail and we learn from that, it's pretty clear we know at least one way it doesn't work and that way doesn't work. So I always looked at a teachable moment as how you pull victory from the jaws of defeat. So I'm glad the world is glad that you changed it from an awful name, Fedora, to Teachable.

Yeah, I actually do not know if I'd be talking to you right now if we'd stuck with the name Fedora. But no, that is so true, by the way. And that's kind of how I I look back at my journey at Teachable. So I was at the company for 5 years. I was the VP of product, you know, first designer, first engineer. And basically everything that I feel like we're getting right at Circle today is likely as a result of something we failed at and had to learn from the Teachable journey. So my co-founder and I joked that we made pretty much every mistake that there is to be made., you know, as founders, as product people, as designers, engineers, et cetera. And so a lot of our life today, you know, where we celebrate our victories or when we appreciate certain things that we got right, it's as a result of having done it wrong and had, and having had maybe thousands of those, those teachable moments while at Teachable.

So there you go. You see like how many times we're using Teachable right now? This is awesome.

Okay.

Yeah.

So here we found like a Teachable podcast.

Yeah, no, that's wonderful. And there's a lot of synergy between the two. Okay, everybody has a moment like this, I think. You're working at a company, things are going well, you're playing a significant role, you're making a lot of progress, you're learning, you're growing. At some point, it comes an opportunity or a frustration or something that you're like, you know, this is your company, you get to do it your way, but we have other ideas. What was that point for you guys to say, like, you know what, we think there's this community-driven thing that we can do. Tell— take me to that point in which it's like it's become clear to you, you must leave, and tell me why, and then tell me how you leave such that you cannot create bad feelings.

Yeah, yeah, this is a big turning point in my life actually. So just taking everyone back to early 2019, so I'm at Teachable, I'm 5 years in, VP product, business is amazing, you know, we had and Teachable, I think, continues to have incredible product-market fit. And what I realize is, you know, I'm actually a two-time immigrant. I actually immigrated to the US from New Zealand with the whole intention of starting my own company and becoming an entrepreneur. This is back when I was 21. And I just realized that, you know, if I was to look at my work at Teachable, very proud of it, you know, having become an executive, having grown the company, but Um, just personally speaking, I felt like starting a company was in my DNA and I hadn't done that yet. I hadn't done that to the scale of, um, kind of what my intentions were. Of course, I had many different like projects and apps and I even had a blog at one point. Um, so that was kind of one driver. The other driver was, um, I was actually in love with, uh, the, the customers that we had at Teachable. Kind of customers that are very much like you. And what I found was, you know, they're not the typical sort of— it's not a consumer startup, so you're not trying to like, you know, limbic hijack millions of people to, to make a bunch of money. It's not an enterprise startup, so you're not in these like boring, you know, sales demos and super long sales cycles. You're actually helping people build their own business. That's ultimately what it comes down to.. And the frame that we had at Teachable was very much around the education frame, right? Hey, let's help people build courses, build their own course business. But 5 years in, my co-founder and I realized that there's actually another frame, which is education. A course is actually a subset of a much bigger thing, which is really about community and engagement, right? And so if you, if you change the, the lens a little bit, what you realize is As a creator, you really go through kind of 4 phases. Phase 1, you're starting to build your audience. That's when you're building your email list, your newsletter. You know, maybe you're getting big on TikTok, Instagram, YouTube. Phase 2 is you're starting to engage that audience. So that's when you may start a community or build a course or even write a book or start a newsletter that you do, you know, twice a week and Your audience really gets to know, know you and know a lot about you through that. Phase 3 is you're monetizing. So you're turning aspects of what you've gotten right so far. And by the way, at this point you may be doing coaching, consulting, et cetera, turning that into business. And then phase 4 is scale. So you're, you're kind of picking the, the various product lines, the various initiatives that you want to scale up. And maybe you've tried a whole bunch of things and some of those haven't worked and you're kind of letting go. So when I thought about that journey at Teachable, I realized that courses always felt to me like they were one key aspect of what engagement could look like. Uh, and still is that way, but there's a larger opportunity around what is possible with communities, with memberships, uh, with coaching, with consulting, et cetera.

Okay. So it's driven by a couple different things. Number one, your dream to start and found your own company. I get that part. And you're seeing that courses are cool, but maybe that's just smaller part to a bigger piece of the puzzle. And so you guys are thinking, you know what, community engagement memberships, we think we can develop a better mousetrap for the education market, the creator economy, right? So you guys have the desire. So tell me how you guys get into this. Okay, we're gonna do this. We're leaving the company, job security, everything's great. And how do you do that in a way that gets your previous employer, founder of Teachable, to say, you know what, we want it, we believe in your vision too, so we want to invest in your company. Tell me how that went down.

Yeah, this was a nerve-wracking conversation, right? Because, you know, my boss, founder of Teachable, Ankur, he's the one who actually set me up for the career path. I was just some designer engineer, this little kid from New Zealand who he kind of made a bet on, promoted me to VP of product kind of 3 years in, and I went on to kind of build out the product team, hire PMs, and go through that motion. And so this is a person who's actually trusted me to be on that, like, on that journey, on that mission, and hopefully not just for 5 years but, but for a longer period of time. So I think the thing, the thought process that I went through was, you know, what would Ankur do? So Ankur himself is a entrepreneur. He's a founder. And I find that founders typically have a bit of a— I don't, I don't know if you'd call it like a rebellious streak or something that makes them go independent, right? And I always felt like I had that. But at Teachable, I was, you know, you're an employee, right? I mean, no matter how early you are to the game, and I was pretty early at Teachable, you're still looked at and will feel like you're an employee. And more importantly, like, you're not owning, um, uh, a meaningful stake in the business such that you shouldn't be an employee. So, you know, you're not, you're not being rewarded, um, as a founder would. So, um, the thought I had was I should just have a direct conversation with him without telling him I'm leaving the company, without, you know, trying to scare him and say, hey, here's where I am in my stage of life, which is I moved to the US from New Zealand to become an entrepreneur. I— you've enabled so much of that through the journey I've had. There's so much that I've learned from you and from the experience, etc. I feel like I'm now at the next leg of that journey, um, and really to, to do what I want to do, the next step involves unfortunately having to leave, leave the company. With that said, what I would love to do is keep you as a mentor, friend, coach, advisor for life. Um, because, you know, whenever we interact, whenever I get to learn from you, there's just so much that I think is kind of mutually beneficial. Um, and hey, maybe someday— and by the way, this is not a time when I had the idea for Circle, so that came much later— but maybe someday you may go on to invest in the company that I start. And there's nothing I would love more than to, to have your, uh, kind of buy-in and belief and, you know, skin in the game, etc. And to my kind of surprise, because I kind of expected that perhaps not to go so well, because you're ultimately telling someone in a very— and you're in a leadership role and you're telling your boss, who's the CEO of the company, that you're not going to be here in the next, let's say, 3 to 6 months. But to his credit, I think he took it as well as anyone in his situation could have. And we, we started to chart out the, the exit path. And I was also— one other aspect of this is I offered to stay for as long as he needed me to help for a smooth transition. So, you know, that, that made sure that his life wasn't going to get harder as a result of me wanting to take the step.

And before I do my follow-up question and summarize, is it public knowledge? I think you've disclosed how much they invested or whatever. Can you share that so that people understand what's going on here?

Yeah. So, uh, you know, Circles raised, uh, over $30 million to date. Uh, our first pre-seed round, um, so the first ever round we raised was early 2020. That was a $1.7 million pre-seed round. Encore, uh, invested about, uh, one-fifth of that. From his personal bank account before Teachable was sold to a company called Hotmart for about a quarter billion dollars. And later I learned that at this point he had basically invested 90% of his liquid net worth into Circle. And so that's kind of how much he believed in me. He didn't tell me that, and I probably would have tried to talk him out of that at the time, but Yeah, it, it all kind of worked out for us.

Yes, I'm trying to do the math. It's not quite $400,000, probably $350K that he's invested in your company, basically draining his liquid assets so that he can invest in this.

Yeah.

And I want to point out to our, our community here a couple of different things that you've done so well. First of all, beautiful conversation between the two of you and the way that you handled it and the way that he responded to it is how we think this should ideally go for every company. And it's a great sign of leadership and friendship in that he goes on to say, "Yes, I will be your mentor and your friend and I will make a sizable investment in your venture and I believe in you so much." And the way that he handled this is this, 'cause there's a lot of people regardless of your age, kind of immaturity that comes into this thing where we feel like we've put in our time, they owe us something, we're gonna go away and we're like, screw you, I'm doing my thing. But the way you ended it and the way that you said it's like, I'm thinking about this. You've actually groomed me this entire time. I was kind of like CEO in training because second engineer in and you're hiring and managing people. He's allowing you to go through all the process of leadership building and then you can inherit those skills. You're like, hey, I came here as an engineer and designer, but actually I have the chops to be a CEO because this is essentially what I'm doing. Maybe not by title, but this is kind of what I'm doing. And you're getting your reps in. So he's very generous in seeing talent in you and assigning responsibilities, and you in return say, hey, I'm thinking about this. I don't have an exact timeline. I want to let you know well in advance because I'm sure when I leave you'll have to replace me with somebody, but I'm willing to stay here as long as I need to so that this doesn't become a burden to you. And in, in gratitude, I would love to continue this relationship. It's not the end of one, it's the beginning of a new one. And you did it in such an open way. I don't know the exact dialogue, but the way you described it sounded beautiful.

You nailed it. And actually, um, to tell you some of the postscript of that specific day, obviously Ankur is not very happy after that conversation. And not happy in the sense that, you know, he thinks I'm betraying him, but sad in the sense that, hey, I'm not gonna— we're not gonna get to work together as closely as we did. And that evening he says, let's grab a drink. Uh, and, and there he's able to process, uh, a lot of the emotions actually with me. And I think some of the worst things you could do in these situations is, one, you don't want to burn any bridges, right? So you don't want to be like, hey, um, you know, I put in my 5 years and I'm done, and I'm going to build something much bigger and cooler than Teachable. You don't want to do that. That's the absolutely worst thing. And you don't want— also want to over-formalize it. Right. So one approach I could have had was to come in and say, here's my, uh, uh, 3-week notice, 4-week notice. Uh, you know, and all of a sudden the dynamic we had of like mentor, mentee, uh, friend, et cetera, is, is gone. And now we're just, we're speaking to each other as an employer-employee kind of, uh, dynamic. Uh, because quite honestly, Circle would not have started without my experiences at Teachable and without Encore backing us. And a postscript to this conversation is, you know, Ankur invested at a, say, $6 to $7 million valuation. Circle's last valuation as of 3 months ago was a $250 million valuation. So it's also been one of, if not the best investment that he's made to date.

It's beautiful. I love it. This is one of those like Hollywood fairytale scripted stories that work out. We usually see the Facebook version of this as lie, cheating, and pushing people outta companies because somebody made a perceived transgression. Okay, now we start the company. You're in it, you're starting it, you're running it. It's not quite bootstrap, but you're kind of beginning again. You have $1.5 million in pre-seed venture capital. You're building your company. Take me through those early stages because I have my experience on the consumer end. And then there's of course the real story, what's happening on the backend. Now you get to call the shots, which means all the responsibility is on you. Every decision is between you and your co-founder, and you can make a lot of wrong decisions. Take me through some of the struggles and tell me the thinking process and how you work through it.

Yeah. So firstly, it was important for me to take some time off after Teachable for about 3 months. I did nothing but sort of just, you know, actually live life with my wife, with my daughter. We traveled a bunch. I reconnected with, you know, long-lost friends and so on. And that put me in a mindset where I was open to the next big thing, and I didn't know what it was going to be, but I was kind of in that mindset of, you know, true openness, true creativity. I could do anything from this point onwards, and it's on me to figure out that path forward. Now, at the same time, you know, I gave myself 3 months. It wasn't like, you know, Sid Yadav goes on a holiday forever. It was like, I have 3 months to kind of re-energize a bit, and then I'm gonna get working on my, on my next thing. So a couple things happened. One, after those 3 months, I started consulting about 3 days a week with one of my kind of old friends. His name's Sahil Lavingia. He's the CEO of Gumroad. And cool thing about Gumroad is, you know, he hires people who could do 2 days a week, 3 days a week as a designer engineer. You get to build stuff. And pays you pretty well. So I was doing that, that made sure that there were— there was cash flow in my bank account. You know, Teachable hadn't exited. I have a wife, I have a daughter, we're living in Brooklyn. So this is important to me. So that bought sort of personal runway to work on my own idea 2 days a week. Second thing I did was to kind of establish the founding team, which I kind of had an inkling while I was at Teachable, but was then formalized. So, you know, I have two co-founders. One of them is, uh, his name's Andrew Gutormson. He also started at Teachable about when I did. He was Teachable's VP of growth and marketing. We were kind of best friends at Teachable. Um, he is sort of, if, if I'm the technical founder, he's a non-technical founder, but, you know, marketing, sales, customer success, those are his, um, skills and he's exceptional at it. And we always joked that we'd try and recruit each other after we'd leave Teachable. So I kind of reestablished my connection with him and got him to at least informally agree to work on ideas with me. And the other dude, his name's Rudy Santino. I think he knows Ben Burns from your team pretty well. Rudy and I have known each other for now maybe over 10 years., and I look at him as my product design soulmate. So Rudy's a designer, Rudy's an engineer, so am I. Um, we are able to deconstruct, uh, products, deconstruct businesses, uh, rebuild— we built many, many apps together, um, separately, etc. Uh, and then what's cool about Rudy is he also worked at Teachable for a little while. He then left Teachable and became a sort of contract CTO consultant, about 30 course creators. So while I was at Teachable, I had the product perspective, um, as an executive. He had the outsider's executive, um, in that he actually worked very closely with our customers to help them build their course business and community. So 3 of us had different things to bring to the table. For me, it was sort of being a designer engineer, but also having the kind of business product backing and sort of being that, you know, that sort of synthesizer of the creative side of building a company as well as the revenue, the money side of the company, as well as the culture side of the company. Rudy, with his design product background and a very direct connection to our potential customer, Andy with his marketing sales background and the ability to grow a product that had product-market fit. So we kind of established a group together. Now we still didn't have the precise idea for Circle, but we essentially spent about 6 months talking through maybe over 10 different ideas that we could be working on. And so what we would do is we'd hop on every Thursday, every Friday, and we'd have like a 12-hour Zoom call.. And we would just talk about ideas, you know, it'd fire up Figma. Actually, back then there was Sketch, it was right before Figma. We would start mocking things up. We would hop on with potential customers. So Thiago Forte was one of my friends from back in the Teachable days. He would hop on, he would help me deconstruct what his day looks like, what his business looks like. And we were just looking for inspiration. And a new mission to, uh, to put ourselves in service to was really the goal. Um, and then what happens over time is certain parameters start getting formed. So we realize, okay, we want to continue to work in the creator space. Um, you know, this is inherently fulfilling to us to build products for, uh, uh, for creators as opposed to your typical consumer or your typical enterprise B2B company. So we want to do that and we want to build a SaaS business. So it's gotta have recurring revenue so we can make money from day one, because eventually we want to be profitable. We want to own our own destiny. So these types of constraints start forming. And we talk about community a lot. Again, thinking about the thing that threads not just courses, but other aspects of engagement, right? Which is, you know, as a creator, you're bringing people together. You're enabling them to connect with each other. They're kind of connecting with you. And one realization for us is there's all sorts of stuff you can do with that, even if you're not trying to directly monetize it. So for example, if you're Figma or if you're Webflow, if you're Circle, you have your own community as a startup. And community in that context is also as important as the context of, you know, creator building community. So Community kind of keeps coming back up over and over again. Eventually we actually get into designing a prototype. That's when we booked out this Airbnb in Santa Monica for a week. You know, I have a family, Rudy has a family, so we realized we just needed to be in a space together for at least a week where we could just have those 16 to 18-hour days building. And that's when we came up with the first prototype for Circle.

Why did you choose to do this in Santa Monica? Why not do it somewhere else? Why Santa Monica of all places?

Honestly, it was just very random. I think Rudy had spent a few months living in LA and Santa Monica in that area. Um, I live in New York. I live in, uh, uh, today I live in Great Neck, Long Island, but back then I lived in Brooklyn. So we just needed to be like close to a beach somewhere where we can walk for hours and hours, um, and just have an Airbnb which completely kind of, I don't know, isolates us from the rest of the world so we can just focus and build together. And it's just one of those places that came to mind.

I'm imagining like a scene from Silicon Valley, the TV show on HBO, where you got some laptops, maybe energy drinks, and just slamming like, yeah, Post-it notes, let's go. Is that exactly key detail?

Yes. The first thing we did was we went to, I think, B&H and we bought ourselves monitors for just that week that we then returned at the end of the week. So we very much wanted that like early startup vibe of like you got monitors, we bought ourselves a whiteboard, we wanted that at least for a week, you know, because we actually, we collaborated remotely otherwise. Rudy lived in, lives in Portugal, but it was important for us to have that like founding moment together in one spot.

Mm. So describe to people why it's important for that moment where you're actually sharing physical space, as much as we're all doing remote work in different time zones, the beauty of being a digital nomad or something, you can live wherever you want. What do you think is so special about people coming together for a brief but intense period of time? What kind of magic can happen only in person that just seems to be lost when we're doing Zoom calls?

Yeah. And just for context, Circle is a remote international company. So we have 140 people spread across 30 different countries today. So we're like the epitome of like a remote startup, but we still do 2 to 3 offsites a year where we bring the whole company together in one place. We just did one in Italy, Thailand, Mexico. We're about to do one in Turkey. And just going back to now the initial days of Circle. There's just no way in the world I see us having started Circle if we hadn't had that week-long founding moment, because I think remote to me is amazing for execution, right? The ideas have been established, the team is there, you need to be heads down and you need to build or support customers or close sales calls, etc. Once the team knows what everyone is doing, once you've established, you know, the org chart and the relations, etc., I think remote is an amazing way to scale a business, scale a company, right? One advantage of remote is that, you know, it forces you to be async. So literally half the company is in a time zone that's not shared with the other half because we're both, you know, people in Asia and in Europe and in North America. So we need to communicate with each other through channels that are not like hopping on a Zoom call. So it's great for that. What remote is not great for is ideating, is brainstorming, is, you know, you have a completely blank slate, you want to be in a room together, you want to talk about every potential idea possible. You don't want an end to the meeting. Right. Then that, that meeting could go on forever. Maybe you, you take a nice walk, just take a little break. Maybe you come back, you know, you start screen sharing and looking through competitors. You want that chaos, that almost sort of organized intentional chaos to seed different paths forward. And then to have the ability to say, okay, out of everything we've looked at and talked about today, what are like the next 3 steps, what are the things that we do from here? And I think we did a lot of that, and at least that, that first week together.

I'm there with you. I think there is something magical that technology hasn't been able to replace yet. When you're in the same room, you can see people, you can see how they react. So if they get excited about an idea, those little micro expressions or body language tells you a lot so that you're not dealing with with the like postage stamp size feedback. Like, what are they even— is the video static? Are they even still here? And you just get the energy, right? So like when we're in the same room, we feel it. And I just finished doing a 2-day, uh, on-site here where, where my managers came in. We had to like power through some tough things. And I think we also get a better sense of who we are as people versus just we're here for a Zoom call, we're going to be gone in a second. So there's something magical there, and I love that. Okay. You guys are doing Circle and I remember in the early days, it must be Rudy who was talking to Ben. He's like, hey, there's this new company. They wanna, they think of us as their ideal customer. They're willing to do whatever we can to help build the right platform. In that moment in time, I think we're still on Facebook and Facebook is great for lots of things. It's horrible for other things. One, it's ubiquitous. Everybody knows how to use it. It's super fast. It understands algorithms. So the things that are most engaged pop up at the top. So it's very easy to get sucked into it. To kind of keep in touch. What it's horrible at is it's a distraction factory because you get on it and your intention is to read the thread or whatever, but then you're pulled to like somebody's cat video or somebody's mom had a birthday and you're like, what? No, no, stay focused, stay focused. And then there's ads and then there's no way to organize topics and threads. And so you guys came along just the right time where like, this is painful. We're kind of kludging parts together to make this work. Oh my gosh, this is super difficult. And then to, in full transparency, and I love the arc in which you've been on, which was initially jumping on made a lot of sense. We overdid it. We created too many threads and people are like, where do I start? It's overwhelming. The simplicity of Facebook, you give us the tools and we go crazy. But one of the challenges was speed. It made me appreciate the massive amount of engineering brainpower that goes into creating a Facebook. With the servers that, you know, that, that infinite scroll. You could literally scroll forever and it never gets stuck. And I don't know what kind of caching and technologies are being used here, but you can scroll forever. And here we are in Circle, it's like, uh, wait, Circle. Yeah. And it was tough. And checking messages, like, one, one thousand, two. But now it's speeding. And I was telling Ben, if they don't fix this, we have to leave because I can't even respond to messages. Talk to me a little bit about how you guys overcame those things and how you were able to prioritize the things that mattered, the have-to-haves and the nice-to-haves and where you drew that line.

Yeah, I mean, all I can say is like, I think we had some incredibly patient customers in more ways than one in that first year, like customers like yourself and Thiago and others who gave us a chance, right? So yeah, we know it's slow, but hopefully they'll work on it. Hopefully they'll get better.

Right.

So first off, that trust is key, but also for us, you know, you kind of have to balance two things, right? So one is you're expanding the paradigm of Facebook. So Facebook is one thing, but your point, what it's lacking is it's lacking context, right? So when you want to establish a direct connection with your audience, with your customer, with your member as a business, what's cool about Circle is you get that, you get that mindshare. So when they're on the future membership area, they're not thinking about all the other things they could be doing with their time. They're thinking about, you know, how do I get the most out of my membership, um, here, right? Uh, and what Facebook has kind of going against it is the distractions, right? Just one click, change tab, and all of a sudden they're watching cat videos. So, you know, on the one hand, we were kind of expanding and extending the paradigm, which involves experimentation. You know, trying out different things, maybe then backtracking on certain ideas that you had. And then on the other hand, customers still expect, and should very rightly so, the polish, the speed, the reliability. Um, and when you're in year one of building a startup, you're learning the hard way. So what you're talking about with the infinite scroll, with the loading times, with caching, all of that stuff, we had to learn and get better at the hard way. Because the reality was, you know, a Chris may give us a chance for a week, a couple weeks, but if we just— if we stayed that way and you weren't looking at or observing the, the progress that the product was making, you would have at some point given up or asked Ben to move platforms. And I think a lot of that honesty just involved building out a real team and going from generalists like Rudy and me building the product writing the code, doing the mockups, to specialists in every area. So today we have, I think, 45 or so engineers. Rudy has a design team of about 10 folks. And the best thing possible for a founder CEO is that they're better than you in so many ways. So like, if you're still the one responsible for like I don't know, challenges like caching or reliability in like year 4, year 5. You built it the wrong way. You want people who are like 10x better than you. In fact, you want teams of people who are like that, and you want to break up the problem so that, you know, you have groups of people, groups of teams kind of obsessed about certain key problem areas, all working together. Now you're still guiding them, and you're still, you know, I still give them feedback about all of the various things that I don't like about Circle that I think we could be better at. But thankfully we have people who are sort of specialists in industry obsessing about and owning these problems. And then it's on me to kind of trust that they deliver and, you know, trust but monitor. But really it's about kind of giving away a lot of the responsibilities to folks who are better than you.

For people who don't quite fully understand this, myself included, there's this, there's this talk about venture capital, seed funding, and, and then pre— what, there's so many different terms that you guys will use. And you're, you need this money because you have to build out the engineering team, the design team, and, and onboarding clients while you're building the product. So there's not a ton of revenue coming in initially, but the heavy investment. At some point you reach a point of stasis where you don't need to burn venture capital where it's self-sustaining and then it gets into a realm of profitability where you're generating orders of magnitude more than you're burning. Where are you at in that and where do you plan to be?

Yeah, so I'll give you our numbers actually, you know, I like to be public with numbers. So for year 1, we launched, so we built the product in a private beta throughout 2020. We launched in September. We had about I think, say $500,000 a year in revenue in September of 2020, having, by the way, given, you know, over 1,000 demos each as founders to the initial cohort of customers in the private beta and having individually made those sales. So you couldn't sign up to Circle and start a community, you had to be guided first. So we went from about half a million dollars in ARR to a million, uh,— within 3 months, 2020. So we end 2020, we're at $1 million in ARR. It's also when we close our first— or actually our second funding round, which is seed round. So that was a $4 million round at a $40 million valuation. That's 2020 ending at $1 million ARR. 2021, we grow from $1 million to $4 million in ARR. That's a 4x year. By the way, 2021, obviously not great for the world in terms of COVID and other things, but it turned out people are spending a lot of time online, especially that year, you know, starting virtual communities and taking courses. It was a great year for, for actually for the business that we're in. So that's 2021. '22, we go from $4 to $8, and then '23, last year, we went from $8 to $16 million in AR. And this year, you know, we want to double again. So roughly that sort of 2x year-over-year trajectory at this point onwards. Now, from a funding standpoint, we raised, as I mentioned, over $30 million. And the last big funding round was in 2021, was back in the good old zero interest rates. I'd say we got very fortunate with some, some very, very generous valuations. Uh, but thankfully we've been able to use that to get to what I think should be the ultimate goal for any entrepreneur, which is really to be profitable, to be cashflow positive, uh, to own your own destiny. And at this point it looks like we're about roughly 12 to 14 months away from it. Um, so, you know, I've set up this one big goal for the company, which is we want to be profitable by mid-2025. That's the one goal which doesn't change. There's a lot of other moving goalposts, but that one goal doesn't change. Right now we're tracking to be profitable by, by March of next year.

Some people are going to have a hard time fathoming that you're going to do $32 million in just a few years out, but more remarkable than that is not yet fully profitable or cash flow positive. Where's all the money going? Help us understand that.

Yeah, um, so honestly, most, most of what we spend on, I think It's that way for most companies, startups that are scaling like us, are the people, right? And so you have, I look at it as sort of there's two types of costs. There's one type of cost, which is a pure investment. Like you don't have to invest in those people, you choose to. And for me, R&D is largely that, right? So if Circle wants to expand into a new business line, if you want to build live streaming or events or payments or courses, well, that's going to require more engineers because we don't want to get the, the people building your feed and scaling that and say, hey, you're now building courses, you're now building XYZ. And so, you know, we're spinning up new teams of people as a product line expands, and that's pure R&D. And then the other aspect of the business is your sort of non-technical orgs, right? So customer support, sales, customer success, and a lot of that is really a function of other numbers that are not entirely in your control. So for example, you know, the amount of leads that we get on the marketing side every day. Yes, that number is something we can influence over a large course of time, but we don't, you know, we don't plan for those leads to show up. They show up and now a certain percent of them need a sales call, need a demo call, and we know that we can convert some of those folks into customers. If we have a sales rep. And so, you know, we have models, all sorts of models actually, that try to predict that inbound, that try to predict the close rates, capacity, etc. As it is with customer support, that's more a function of number of support tickets and how that maps your customer growth. And with customer success, which is really, you know, how many of these customers, or rather what percent of your customers do you want to give like the best white glove experience too, where it's not just about helping them with their pain points like support tickets, but actually it's about helping their businesses grow. And so we have team of folks doing that. And so for me as a founder CEO, it's about deciding which areas of the business to invest in to grow, which areas to pause. And one key tool One key thing that I've discovered in the last 6 months of aiming to be profitable is kind of the power of pausing certain initiatives, right? Because there's all this momentum, people want to work on everything, and you don't always get to be in these conversations where stuff gets worked on. But you do get to say at times, hey, you know what, we've done enough in this one area, we're going to pause for a little bit so that team can maybe refocus on certain certain other things, because if we just kept building, we'd have like 4 or 5 people just doing that, and then we would need new people for other things. So it's almost this like this art around investing in certain aspects of the product, investing in growth, and you know, what is that ideal composition that values both the customer— so the product improves, experience improves— and the business, which is your you're, you're getting to grow and make money, uh, from all of those investments.

In terms of like the, the servers, uh, that you have to use, how much of that percentage-wise in terms of your operating capital? So I heard staff that are on the product team, then there's a sales and marketing team, and there's customer success which includes service. So it's heavy people, it's labor intensive. But what about just the technical stuff like servers that you have to purchase or rent or lease? What percentage does that make up?

Yeah, so that's about 10% of our revenue. So if you were to look at our COGS as a composition of servers, infrastructure, and customer support, you know, we're— I think our gross profit margin right now is about 80%. And so the 20% that does get spent, you know, it's kind of split across servers, infrastructure, like non-optional. Like, you need to keep the site up and super reliable at all times, uh, and you need to support the, the customers who do have issues or who do need that help. Um, and that's almost unavoidable. Now, the great thing about a software business, and actually great thing about the internet, is that 80% gross margin is like amazing. Because if you look at most other industries, you know, you'd be lucky to have like a 50 to 60% gross margin. And that allows us to scale, you know, profitably over time because we're not, we're not losing most of the dollar that we, that we earn.

Yeah. What else is contributing to the cost of goods sold besides the servers? So people understand cost of goods sold is it scales with the number of customers that you have. Overhead doesn't necessarily, but cost of goods sold, it's like, what does it cost you to service one new customer? And so you're saying for every new customer, we spend 10% just on the servers alone because it's non-negotiable. You need the server space, it needs to be fast, it needs to be reliable, redundant. What other things contribute to cost of goods sold?

You know, for us, it's really just those two. It's the infrastructure and it's the support. But I'll say that infrastructure, you know, we can simplify it and say it's about the servers. But when you look at the infrastructure bill, there's like, you know, 20 different costs associated with that, right? So Circle sends over 100 million emails, uh, a month, um, for just transactional notifications. So now there's an email service, you know. We have a live streams feature where people can go live on Circle, and that has its cost. So you break that down into just various components, um, of, you know, quote unquote, keeping the site up. And of course, when you're a customer of Circle, you know, you don't look at that and say, oh, it's really this one service that went down. For you, it's about Everything being reliable or not. And, and for us, it's a matter of these things being kind of table stakes.

Yeah, this is fantastic. Okay. Um, I mean, it's, it is the dream of most corporations to spend 10% as a cost of goods sold, kind of all in. This is fantastic. There was a couple other things that you mentioned. I want to be sensitive to people who aren't entrepreneurs, who aren't CEOs. You said ARR, that stands for annual recurring revenue, and you're just looking at that number, like, what are you going to be able to do reliably predicted you'll do next year. And the idea is to continue to grow. You're talking about 2x. You mentioned R&D. I think everybody knows what that is, but just in case, it stands for research and development. So there's the product itself and there's the things that you need to do to continue to serve the unarticulated needs of your customers. So that requires you to pay attention to what's going on, look at trends. And that leads me to the next question, which is, who do you see as potential or existing competitors to what you do? Because there's a lot of platforms that service content creators and educators?

Yeah. Where do I, where do I start with this question? Yeah, we, we have a lot of, I'd say potential competitors or somewhat competitors. We have very few direct ones actually. So, you know, I would say actually our two biggest competitors from the perspective of we either lose people to them or people may not use Circle because they're pleased enough with them, or actually just Facebook groups and Slack. Right. Because many people are like you, which is, you know, hey, I've got a Facebook group. Why do I need to move them off somewhere else? Everyone in the world uses Facebook. I'd say actually vast majority of creators are in that headspace until they start to scale up a community experience within Facebook and, you know, run into all the various pain points. And some may even struggle with engagement because, yeah, you are on Facebook, which has over a billion DAUs, but you're also competing with the rest of the world. And so for us, we actually spent a lot of time just thinking about that, which is, you know, at the top level you have people who are maybe happy enough or pleased enough with Slack and Facebook Groups, and for that reason they may not be giving Circle a shot, or maybe they give Circle a shot and then say, you know what, I'm just going to go back to Facebook Groups, it's free. So For us, it's really— those are the tier 1 competitors. And then tier 2, you know, we have other products in the space that go kind of more head-to-head. You know, there's obviously Discord, there's Mighty Networks, there's actually a whole plethora of these types of competitors. And where we try to differentiate is to say, you know, we want to be the all-in-one, right? So eventually we want the future or the next future to run most of their business, not just community on top of Circle. So that includes courses, events, maybe in the future newsletters, consulting. And that's our point of differentiation, which is yes, you're not on Facebook, which over a billion people use, but your entire business is on Circle. And that's a different kind of value prop now, which is, you know, you've built this ultimate member experience., that you're either selling to or offering your, your members. Um, and because everything's in one place, it's easy for your members to engage with various parts of your business, for you to upsell them into multiple different types of experiences. So may— maybe you're logged into community and then you see that, you know, Chris is running an event. Hey, I'm gonna RSVP into that. Or, you know, you check the newsletter tab and you start reading posts. So it's, it's about kind of unifying that experience. Um, and that to me is our ultimate future value prop. You know, we're working our way to that. And that's also the ultimate challenge, right? Which is Circle eventually ends up being not just one product, but like, you know, 5 to 6 different products that we have to get right.

I guess I want you to look into your crystal ball. Can you share with us whatever you're able to disclose, some things that you're very excited about in terms of features you're working on that will be released sometime in the near future? Or at least give us a clue, tease us a little bit, will you?

Yeah, um, so just going back to what I just said, you know, when I look at the all-in-one pie of a creator business, uh, like yours, um, you know, I just feel like we're, we're maybe like at the halfway mark, uh, but there's a lot of stuff that we don't do yet, um, that I hope we can get into, as well as with the stuff that we do, you know, the other half we want to get right and we want to be the best version of. So Um, in terms of, I think, what would make for an exciting teacher, actually there's a lot that I could talk about, but I don't want to make our engineers, um, uh, freak out over this podcast, uh, if they happen to be listening. Um, what, what I will say is the following. So I think at the start of the, the show I spoke about, you know, start, engage, monetize, and scale. So those are the 4 steps to the journey of a creator. I really feel like over the last 4 years, we've been very obsessed with the engage part of that journey, right? We assume that people already have an audience before they start Circle. And then we launched, you know, payments a year and a half ago to help them monetize. We haven't been as focused on the start and scale aspects of the business. Start aspect would be, you know, are we helping people even build an audience? You know, why is it that you need to build an audience? Maybe in an email list product or newsletter or TikTok before starting Circle. So can we expand the pie of customers at the, the top of the funnel? And I'll just kind of leave it at that. And on the scale aspect, it's really about, you know, helping the future futures stay on Circle, right? Which is we don't want you to have to outgrow us. We want to support you as you guys become, you know, $10 million business, $100 million business, I imagine eventually there'll be a billion-dollar business. Um, hopefully, uh, if not on Circle but in the wider world, uh, a billion-dollar creator business to me seems inevitable. And we want to build that ultimate product which people can start with and then scale to. Uh, and yeah, there's a lot going on there. Which are both sort of weaknesses of Circle today, a lot of pain points that we want to solve for, as well as opportunities, because we know that if we solve for them, we're going to be helping a lot more customers start, engage, monetize, and scale.

Okay, a couple of questions I have for you, and feel free to plead the Fifth or be evasive if you wish. We're in the political season anyway, so nothing would surprise me, right? I noticed something that Facebook and many of the social platforms do, which is they don't give you chronological feed. It's built on engagement and understanding how people react and respond to things. Is there any desire to do that? Because there are threads that are created and it's like, I gotta scroll down to find them. And just because it's newer, it sits on top, doesn't mean it's the best thing to be seen. Uh, so are— is that something that you're looking into? What can we expect there?

Oh yeah, 100%. So I think there are two types of problems people struggle with with Circle, right? So one is a problem of engagement, which is literally the opposite of that, which is, you know, there's crickets in my community. Yeah. And then for the folks who nail engagement to some extent where there's a lot of activity, there's, you know, posts and comments and threads and there's stuff happening all over the place. It's like, oh my God, this is too much. Like, what should I even be looking at?

Or.

Responding to. And, you know, again, over the last 4 years, we've really been focused on that, the problem of the crickets and the avoiding that, that kind of silo, um, you know, the feeling of sort of non-vibrancy, sort of static feeling experience. And to the extent that we've done that for customers like yourself, um, we are only starting to scratch the surface on solving for basically a smart feed, which would be kind of version what you're talking about, showing the best of. And by the way, there's also other ways to do that. So, you know, we have a weekly digest that goes out that could be a lot smarter, let's say. And one really cool part about working on these challenges right now, as opposed to, let's say, 3 to 4 years ago, is that AI just keeps getting better and better. So when we're now approaching these challenges with the tech, the AI tech that's enabled to us, especially in the last like 6 months, you know, there's a whole new sort of tool belt that we have to undertake these challenges. So I'll kind of leave it at that, but very much kind of hear you on the core problem. And I think there's a lot that we need to be doing here over the next year.

Okay, oh, you kind of already opened the next can of worms for me, which is AI, to be able to use AI-enhanced everything, feed summaries for calls or thumbnails. One of the features that I really like is when I make a post, we know that visuals help to create excitement and always have time to figure out what's going on so that your early integration and play to include Unsplash as an ability to just create something, here's a quick thing, I think that's good. I think the next level of that is let me just type a few keywords or it intelligently already knows what I've written about here. May we suggest a few AI-generated images? Click a button, boom, get it in there and it to, to do that so that it's not stock, right? I, I think something like that would be beautiful. Some other things I think about are, and I, I just curious to, to, to get your take on this. I think we're a fairly unique and demanding client. We have so many weird ways that we monetize, either through courses, uh, through just downloadables like PDFs that we can sell. But we have coaching communities, and we have different payment plans and ways to structure it. So one community, it's just pay-as-you-go, open enrollment. The other one is open specifically during certain windows, and you must commit to 3 months of building, uh, because we, we know that 90 days is what it takes for you to form a habit. We don't want you to dip in, be a looky-loo, and then jump out. There's not enough time for us to show you that your life can be transformed. That's one of the challenges. Is that something that you would be— that you would consider working on or prioritize so that we can then make this a more seamless thing? So it's like different ways of onboarding people, different payment thing, plans. And so that it's, we're removing all the friction for people to sign up.

Yeah, absolutely. I'll take the second one first, actually. So my co-founder Rudy calls this connective tissue and a problem we've struggled with from day one is like, we don't want to create silos of experiences, right? But at the same time, we want everything to feel connective and cohesive. And by the way, like the whole reason you would want your entire business on Circle is really that, right? It's to offer both your members an experience that feels cohesive and connected, and also for you as a business to have these opportunities to upsell, cross-promote, have sort of seamless transitions from one aspect to your business than to the other. And I think that again, the last 4 years have been about having those building blocks in the first place, right? So it was about like building events, building payments, building courses, live streams, et cetera. Now when we do these design sessions, you know, Rudy and I like to spend at least 3 to 4 hours every week just kind of just thinking about the future, ideating, you know, I mean, you're, you're a design sort of connoisseur/guru, so you know this, but you know, we like to go pretty far out, right? So what is Circle look like in 2025, 26, 27? And what's cool about being a design-led company, really feel like, you know, it's two designers running Circle. We get to do these thought experiments and start to see some of the mockups and the prototypes taking shape. I think the more we do those exercises, we discover almost an n-squared number of these types of opportunities around the connective tissue. Actually, Rudy shared me— shared with me something, uh, just, just today is that I think he did a 3-hour session with Ben from your team about this very topic. Yeah, so I'm sure they've gone pretty, pretty deep on this, but it's definitely kind of the next sort of frontier of the product, which is, hey, now that we have all of the building blocks, how do we both build a cohesive experience ourselves and help our Communities provide that to their members.

Yeah, I, it's something that we talk about a lot in our internal meetings where it's like we want an experience as one username, one password. Yeah, okay, there's a Zoom thing and then there's a Slack thing and there's a lot of other things we've got to— there's a Teachable account versus this and it's just we, we, we want to make it like an elegant experience. You saw, you call it the connective tissue. Where someone can log in with one username and find all the things they've purchased. They can chat with their friends, they can see what's going on in events, and it's all brought together in an elegant way. It's the best way I know how to describe it. And without getting into like a case of feature-itis where you're just putting the kitchen sink and everything else in, to build on the core foundational components and then to integrate parts that make a lot of sense to kind of remove that friction. Now I want to say this on behalf of everybody who's listening. What is— what the heck are we even talking about, right? So I'm going to describe it from the user's perspective because I think that's going to give you the most honest portrayal. And then feel free to correct me where I may have misspoke, Sid, because I, I'm not just having any random CEOs on the channel. I, I'm— if I don't believe in what you're doing, if I can't talk about it in an honest and effusive way, then I'm not sure it's a good use of either of our time. So let me just tell you something, okay? So everybody who's paying attention here, I'm just going to go on a little monologue here, okay? Our mission is to teach and to leverage the power of the internet, social media, to teach as many people in as, as low money commitment from our students as possible, because we believe in the power of education being transformative to get people out of poverty. And the people we want to serve the most are the least likely to afford what we do. So we create lots of content for free behind no paywalls, then we would go broke. And the way that we make a living here at The Future is that some people say, you know, we love you so much, we feel so grateful for you that we would love to either give you money just to participate in your communities, to go deeper and have greater access, or to have more organized materials in courses. And that's how The Future continues to run, and that's a business model we're on. So as an educator-creator myself, I have to look for technological platforms that allow me to do this in the most elegant way. Many of you are familiar with the Teachables of the world, which is course creation. They're, they're very good at doing that, especially if you have one or two courses. But when you have a variety of educators, lots of different curriculum, that starts to even break and strain the system. And we know this. It's like if you enroll in a course and students have work that they'd like to have feedback on or to be able to reach out to you in an office hour or just to get some critique, That platform doesn't seem ideally suited for it. And this is the beauty of a community-led platform like Circle. So you can have courses that you can open and unlock as you wish. There is a live chat function which shows you a thread that's chronological. It's pretty cool. That's a new feature. There's obviously messaging. You can go back and forth, uh, and there's lots of different ways to organize events and posts so that they feel and look like the way that you want versus you must, you must use the templates in which Facebook or one of these big companies have created for you. So there is that sensitivity to the needs of a designer or creative person. Sometimes you want list view, sometimes you want thumbnail view, sometimes you want big bold images and sometimes you want, and it depends. And we love that there is for the most part one tool, one platform that allows to do this. It's getting better every day. Used to be that sending messages was like a pain because it would take forever for it to cycle. Now it's quick, at least it's quick enough for me to use. I'm excited about it again. And we see all the smart decisions that you're making. So for, for the, for the, this broadcast in this point in time, I'm a big fan. And I'm saying that I'm not getting paid. There's no money being exchanged here. If you're an educator and you're trying to figure out how do you make a living doing what you love and you love to teach and help people to create the kind of transformation we're talking about, I highly recommend you guys check out Circle.

Wow, that was beautiful. You've pitched Circle, I think, better than I ever could. Thank you so much. That means a lot.

Well, as a user and as a believer, as the song goes, I'm a believer, you know, uh, I, I can talk about it and not feel like I'm being some kind of slick car salesperson. I'd love to end our podcast today with a question that allows people who are interested, curious, from a CEO point of view, something that they can do, some actions they can take. Maybe they're inspired, maybe there's some lessons here. But the way I'd like to frame this is this, 'cause you have a unique perspective, is if you look back on your life and you could tell your younger self something, some key insights. And I want you to literally think about you 10, 15 years younger. What would, what are the 2 or 3 things you would say to your younger self to accelerate this process or to make some of the hard decisions much easier?

Yeah, wow, what a great question. I think key thing that comes to my mind is I feel like I wasted so much time. You know, like I think I did a lot of the right things, but It really feels like, you know, the things that ended up mattering the most in my life were the smartest friends that I had, the ones that I got along with, you know, my co-founders Rudy and Andy, you know, Ankur, my boss and CEO, uh, at Teachable. And when I look back at it, there's so much that I was doing that didn't involve either working with them, learning from them, you know. So for example, right, I would attend a lot of these meetups when I first moved to New York City, and for a while they were fun. I was just getting to know the city, but eventually I was kind of like, hey, am I really learning something here when I could be at home kind of building an app or talking to, talking to Rudy about building apps and so on? I think so. One thing that comes to mind is like, you know, you want to be, you want to maximize the amount of time you're spending, actually building stuff, or talking to your smartest friends about building stuff, as opposed to, for example, uh, like thinking about building while not doing it. Um, and of course there's a balance of that, and there's— everyone needs inspiration, everyone wants to learn, right? But it has to be applied And it has to be sort of in action. Uh, and without that, I think what a lot of founders face, what I faced honestly before Circle is that, you know, I'd get started with something and then I'd get into kind of either learning mode or procrastinating mode. And then I'd give up on that thing and then I'd move on to the next thing. And I've probably done that countless times before Circle, whereas if I look at what really What really made Circle or what really kind of went behind it, it was the fact that Rudy and I were— spent that week in Santa Monica. Ankur was a big believer when I, you know, Slacked him a prototype of the product and offered to wire us that check. Andy agreeing to hop on as a co-founder and all of us just really being in sort of build mode as opposed to think/procrastination mode of talking about the ideas without actually doing the work. So You know, if I was to sum it up, I'd say kind of just do the work and maximize the amount of time with your smartest, closest friends, especially if you see them as close collaborators. Because every moment that you're not doing that and that you're spending, you know, watching cat videos or trying not to think about work, etc., those are just wasted, wasted moments. I'm 31 right now. Maybe I could have started Circle, you know, 4 or 5 years before when I actually did. And so I think about all that time that was, that was kind of lost, not, not being in this mode, because what I find right now is I am the most fulfilled. So of course, running a company with over 100 people is like super challenging. Of course, my days are filled with sort of problems and crises and whatnot.. But I know for a fact that I'm utilized, uh, my brain is utilized to the extent that it can with the hardest, most rewarding problems. And I haven't had that for, for a lot of my life, dare I say, before I, um, before I joined Teachable. So yeah, I just kind of encourage folks to, to do the work.

Hmm. Okay. That was excellent. Well said. So there's this thing that all creatives get into, whether you're an engineer, designer, or classically trained artists, which is you do a lot of thinking. And one of the things that gets in the way of you publishing work and putting your ideas out into the world is this perfectionism that we all kind of fall under, or we get into deep research mode, we'll call it that. And so you're looking for all the ways it can fail versus just finding out if it could succeed. And I love the way that you said that you, you have to make this choice. Either to take action to build what you want, or at least express the intention of taking that action so that someone else can hear it. And that way you're vulnerable enough to put the idea out there for it to be tested within the realm of thoughts and communication versus just keeping it locked into yourself. So for a lot of you who may not have founder friends like the ones that you were able to meet, even just journaling and publishing your thoughts is good enough because you're gonna get feedback from the world. They're gonna surprise you. They'll get really excited about something. You're like, that just a little thing? Or the thing that you think is gonna be the winner, no one cares about. Everybody's like yawning. So the best way to do that is to share, to express, and to publish and let the chips fall where they may so that you don't wind up looking back 5, 10, 15, 20 years and saying, my God, I wasted the best years of my life. Your most productive, energized moments physically that you're so capable. And now you're coming to that realization fairly late. Let this be a kind of a wake-up call for some people. Look at this young man. He's 30 years, 30, a little bit over 30 years old, and he's running a company that's projected to do $32 million with a $250 million valuation. His former boss invested 90% of his liquid assets, and it seems like they're on a very high trajectory. They're going places and he's just a baby. He's barely 30 years old. Come on. This is fantastic. So I don't think you wasted any time at all. You're doing great things. And I just think it's like the Asian immigrant in you is just like, you can do more. Why aren't you a billionaire already?

Actually, if I could share just one thing, uh, as you're talking, I thought of this. So when we, when we first built the prototype of Circle, um, and we raised that pre-seed, I had this inclination to think, okay, maybe we're going to spend the next 2 years building Circle and then we'll announce it and then we'll launch it. I think, you know, a lot of entrepreneurs when they're given that kind of runway, because we're looking at the $1.7 mil, we're barely paying ourselves anything. We're thinking, hey, we don't have to actually launch this thing until, you know, someone like Chris thinks it's like super fast and reliable and all that. Maybe we shouldn't even talk about it. And then there's a key moment where I just kind of tweeted that, you know, moving on from Teachable, starting a company. I didn't even mention Circle. And it was just a very offhanded tweet. This was not an announcement. It was just kind of updating mostly kind of friends and people I'd known on the internet. And that tweet got way more attention than I ever thought it would, with people asking me what that, what that next big thing was. A couple days later, we just, we put together this very bare bones marketing site for Circle to start a waitlist off the back of that tweet. And I just tweeted that again, not with the intention of announcing my next big thing, but just kind of putting it out there that, you know, raised this pre-seed and now I'm committed to building this. That was one of the best decisions I've ever made because that tweet got us, I think the first 5,000 leads on that waitlist who we then spent, you know, the months of January to October selling and onboarding into the platform. Now, obviously a lot of those customers didn't convert or may have just expressed interest in my company, but we're not really potential customers. But just to share one example of what kind of putting yourself out there can enable, as opposed to kind of bottling up the the creativity, bottling, you know, just making your— convincing yourself that you need to have the best version of XYZ to put yourself out there. Um, because really that feedback loop that this creates, uh, which then honestly energizes you to deliver on the promises that you've shared with the world. Uh, and so I just wanted to share that.

You know what, when you were saying all this stuff, you reminded me of something that Guy Kawasaki says There's a famous Bobby McFerrin song, "Don't Worry, Be Happy." And so it's, "Don't worry, be crappy." It's okay to ship a product that has elements of crappiness in it, but just don't let it be the forever perpetual state. You have to work the crappiness out. And let's just say it did ship with a little bit of crappiness in it, but you work through it. You can attach to that. Yeah, yeah. It was a little slow, it was difficult to use, but, you know, eventually you got it. Guys, you'll figure it out. And for everyone out there who's afraid to put their ideas or their artwork out there, you're sitting there trying to eliminate all the parts of crap and you never ship. And it's better to ship something with elements of crappiness in it than it is to never ship at all. Okay. I enjoyed our conversation. You were super generous and transparent. I hope our— and I'm pretty sure I'm speaking on behalf of our audience. Uh, thank you very much. Thank you very much for doing this. It's always awesome to talk to CEOs who are as forthcoming and transparent as you. Thank you very much, Sid.

Hi, my name is Sid Yadav. You are listening to The Future.