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📐 The Lab Builders Are Leaving. An interview with Andrew Dai, Co-Founder & CEO at Elorian AI.
🧗🏻 Unfiltered: The System Vanta Built To Grade Its Own AI. How they build language models as the judge, human as the jury, and more.
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HOUSEKEEPING 📨

It’s honestly so simple to outcompete your competition or simply outlive your neighbor. Gambling sucks, and if you have social on your phone, get rid of it. You will be light-years happier and more successful. I am pretty successful with numbers one and two in Shaan’s lift here, and am slowly working on the third.

One thing I’d add to this list is reading. If you read a few pages every night before bed, you will also be outlearning and giving yourself the best chance of getting quality sleep. One of life’s great win-wins. I’m currently reading Dracula. I’m loving it.

INTERVIEW 🎙️

Sid Yadav, Co-Founder & CEO at Circle

Sid Yadav is the Co-Founder and CEO of Circle, the all-in-one platform for community-led businesses, covering membership, courses, events, discussions, and, as of this month, a full website builder. Originally from India, Sid grew up in New Zealand, where he spent his teenage years writing Rev2, one of the internet's earliest tech blogs, before moving to the US as a founding engineer at Teachable, where he eventually rose to VP of Product and helped scale the platform to over $1B in creator earnings before its acquisition. He co-founded Circle in 2019 with Andrew Guttormsen and Rudy Santino, both former Teachable colleagues. The company has raised $33M, with Tiger Global leading the Series A at a $200M valuation, is now profitable, and has crossed $50 million in ARR with 280 people and a customer list that includes Jay Shetty, Tim Ferriss, and Ali Abdaal.

What makes Sid's perspective worth paying attention to isn't just the trajectory. He and his co-founders wrote Circle's values document before they signed their Stripe Atlas incorporation papers, having watched culture quietly degrade at Teachable as it scaled. He accidentally got the timing right too, launching in August 2020 into a lockdown that made digital community feel urgent for the first time, and unlike Zoom and Shopify, Circle never gave back the growth. He also still codes new apps every few days to understand the business. At 280 people, the big question now is whether turning Circle into an AI platform, which is exactly what a major recent launch signals, changes what the community model actually is.

What are you building at Circle?

We started six years ago. It's the all-in-one platform for community-led businesses (we call it an ‘ecosystem’ these days). The thesis we have is that there are all these people building content, making videos, writing newsletters, which is a fantastic way to build an audience, but when you look at a lot of these businesses and creators after a few years, there can be a sense of fatigue and burnout. This feeling of being on a content hamster wheel where you have to keep producing and producing. And on the audience side, there's this feeling of ‘there's a lot of content out there, but am I actually doing something with my life?’

The idea with Circle is to build this ecosystem that gives every creator and entrepreneur the platform to build their dream community-led business. These are really any businesses where people are at the center of the value proposition, versus the content or the audience. They typically have aspects of membership, discussions, events, courses, something for people to show up to, to interact with each other, and get value out of. Not every community-led business is the same. They all vary in shape, size, and outcomes. But there's typically an element of belonging, and an element of transformation, where you don't just show up to hang out in a Discord or a Reddit—you actually show up to grow as a person.

What are the best case studies you have on the platform?

To start with the known names, we're very grateful that we've built a platform used by some of the top creators, like Tim Ferriss, Ali Abdaal, and Jay Shetty. We've got all the Harrises, too (Sam Harris, Dan Harris, and Johnny Harris). They all follow a similar theme, which is that these people have built audiences, and at some point in their creator-led business, they discover that they want to run events. They want their people to have an area to belong that isn't just the YouTube comments. So they need a platform, and especially when they build in-house teams and get serious about it, we tend to become that default platform.

But Circle isn't just for the top creators. It really is for everyone. I have a couple of more concrete examples I find genuinely cool. There's this couple, Dr. Aisha and Dr Dean, who are neuroscientists. An entire career thinking about brain health, operating on patients, doing surgeries, and they had this idea at some point: we can operate on hundreds of people over the course of our lives, but if you actually want to impact the world, you have to do more than that. So they started a community called ‘The Brain Docs’. It takes all of their learnings and builds a community experience around people who want to get better at brain health. They run weekly cooking sessions with ingredients that are best for your brain, and so they've built this audience of people who aren't just passionately watching Andrew Huberman interviews, but actually doing something about it. Here are these people who built a career, who are still doctors, but now also have this business. They've had much greater impact, and all of it has been built on Circle.

Sam and Dan Harris are the ones you'd expect people to know. What do they actually do with their communities?

Dan Harris’ ‘10% Happier’ is a good example. He's written books, been on podcasts, and built an audience around happiness. These creators share ideas, build audiences, get book deals, monetize the ads, but at some point, there's this feeling of ‘we're speaking to these large audiences, and where do they go after that?’ Dan's community membership is really built around just that. There are a lot of people who love Dan Harris but also want to actually live out his ideals with each other. And what a lot of these creators find is that, unlike a Substack or Patreon, where people show up mostly for the creator or the content, with Circle, they show up for the creator, but they stay for the community. Once they engage with each other, there's this feeling of ‘I'm genuinely happy just meeting people who are like me, undergoing the same transformation, and I'll pay for that’. They don't actually need to keep watching the creator's exclusive content to stay engaged.

What was the hardest thing about getting the company off the ground?

Honestly, I don't think I can complain too much, because we had a phenomenal first year. Unlike a lot of other stories I hear, we were starting the company in late 2019, and then COVID happened. The creator economy really entered the mainstream zeitgeist. There was this real need people felt for communities, especially online digital communities. We started the platform at this accidental stroke of luck moment, and we went from zero to a million in ARR in three months, from our August 2020 launch to December. So we don't have the typical struggle of finding product-market fit.

With that said, I had a lot of personal challenges that first year. My co-founders and I are all engineers and designers, very hands-on people. The company is 280 people now, and we're still very hands-on. The challenge was selling the product to all these people and onboarding them while building it yourself. We were engineering and designing the product as it went, which was fantastic for the feedback loop, but we were selling, building, and marketing simultaneously. And then, because we'd raised pre-seed money, building out the initial team, delegated support, brought in more engineers, formed the first leadership team, all in one year. TLDR: it was just a lot of work. No weekends off. So my struggles were really personal struggles around time management and delegation.

Did you worry when lockdowns ended?

Yeah, we were paranoid about it in some ways as COVID was ending. I know it affected Zoom, Shopify, and Stripe; all of these companies overhired and then had to correct for it. For context, our ARR went ‘triple, triple, triple, double, double’ journey, not that we were intentionally optimizing for that formula. But I think the reason we didn't struggle is that the creator economy just kept doing this and growing, unlike virtual events, Zoom calls, or working from home. Those trends reversed, while the creator economy didn't.

On top of that, the creator economy itself just kept getting bigger. Podcasts are everywhere. Creators have bigger and bigger audiences. That never slowed down.

What changed after the Series A?

So we did $1.5M pre-seed, $4M seed, and $20M Series A. The biggest shift, honestly, was resources. In the seed days, there was always this runway countdown. In the pre-seed days, we paid ourselves as founders almost minimum wage, because we didn't want our salaries affecting the burn rate. You're at sixteen months, then fifteen, fourteen, thirteen. Then the seed tops it up a bit; you're at thirty. But then you build out the team, start spending a bit more, do your first offsite in year two, and even that starts to count back down. Then you raise the A, and suddenly the runway is just massive. In our case, the burn was fairly low, and we'd just raised $20M. You can't even really think about the runway anymore. And then the problem flips. Now the question is how fast you can deploy this money across all the areas of the business that really need the best people. And those people now need teams. About a month after we raised the Series A, we hired our head of sales, head of customer success, and head of finance. So the first job was building out that initial leadership team.

For me, as someone who'd been doing everyone's job, it was about backing off a little and helping these people establish their roles. We went through this evolution in phases. Phase one, we did all the work. In phase two, we hired generalists who could handle more of the work while we were still very hands-on. Phase three, leaders building their own teams, those teams needing to be really aligned with your vision and values. And then it's just a delegation, trust-but-verify scaling game from there.

What does your actual week look like as CEO right now?

Every day is pretty different, but I try to maximize my time with my co-founders and a very small number of people in the leadership team. I think about it in terms of leverage. If I'm talking to my co-founder Andy for an hour and a half, he runs all of GTM, which is close to eighty to a hundred people under him. Whatever topics we're covering in sales, marketing, customer success, that's now being taken care of. That frees me up to spend the rest of my time on areas where I'm deeply engaged, which tends to be culture and product, and usually one big project. Recently, it’s been a major launch we led in June.

And then there's being the face of the company internally and externally, which only I can do in my role. So I've completely flipped it from a week full of meetings to trusting the team to run most of that and getting super involved wherever I think I'm the best use.

How did the culture change as you scaled?

One thing we had going for us was that my co-founders and I spent five years on the founding team of Teachable before Circle. I grew up there, went from IC engineer-designer to Product Manager to running Product. The company sold for about a quarter of a billion dollars. But one thing we learned from Teachable is that we never codified our culture or values very well.

A lot of those top values came from experiences at Teachable, where we'd felt them but never written them down. That document still exists today, and it was there when we onboarded our very first team member. The most challenging period for culture was probably when there were 50 to 100 people.

How is Circle using AI operationally right now, and where is it going?

About 18 months ago, we did this AI mandate offsite in Spain. We're remote and international, so we flew the whole company to incredible locations. We spent an entire day with each leadership team and started wondering what this function would look like with AI. It started with an insane process mapping. The philosophy was that this won't be top-down or bottom-up; it'll be both. It's not going to be the leadership team or me dictating how everything changes with AI, but it's also not going to be a free-for-all. So we mapped what everything looked like, assigned AI leaders in each team, and held those leaders accountable to AI outcomes. And we took the approach of defining the outcomes, defining the leverage points, but not being opinionated about the tech stack. If one team wants to use ChatGPT and another Claude, that's fine, as long as they're achieving outcomes. So Circle has achieved a lot across the board, but in this somewhat fragmented state where we haven't unified the tech yet, and that was intentional.

Now we're entering a phase of unification. If sales, CS, and CX are all doing their own AI thing, but they're all dealing with customers, what does that one true end-to-end system look like? And more importantly, how does the product itself change? We're going to be launching a lot of critical AI features, almost turning Circle into an AI platform, so that a bunch of things that currently require human intervention just won’t anymore. Before a ticket even emerges, before someone in customer success has to talk to the person, their jobs evolve to higher-level problems.

How do you get the best out of yourself?

The deeper thing is that, as a Founder, you think you have to be working all the time because there are always more problems. But when you do something like this for yourself, you come back with better energy, a clearer mind, your decisions get better, and you feel it. That's the counterintuitive bit. Investing in yourself beyond a certain point is also investing in the company. You don't have to feel guilty about it.

Extra reading

• Circle's Eclipse Is The Biggest Creator Launch Of 2026 - June, 2026

• The best ways to use Circle MCP - June, 2026

And that’s it! You can follow Sid on LinkedIn or check out Circle on their website to keep up with what they’re building!

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