Exploring a classic American dream with Sid

Ayush Jaiswal (0:00)

Hey, everyone, welcome to the Startup Grind podcast. I'm your host, Ayush, founder of Pesto. For this episode, I have Sid with me. Sid is the founder of Circle.so, and he's a friend who, you know, I've been hanging out with for quite some time, and his journey of how he got started is one of the most insane founder journeys which I've come across.

Sid, thank you so much for taking our time. Welcome to the Startup Grind podcast.

Sid Yadav (0:25)

Hey, what's up, Ayush? Thanks, thanks so much for having me on the show.

Ayush Jaiswal (0:28)

Yeah, Herb Sand. I know before Circle, you were working at Teachable. Would love to start with the story there. And Teachable is where you met your co-founders as well, right?

How was it like building Teachable for five years into the company it became later on? And when did the idea of Circle came about?

Sid Yadav (0:47)

Yeah, so just to set some brief context, I'm a two-time immigrant. I was born in India.

My parents moved over to New Zealand when I was 10

Ayush Jaiswal (0:55)

Oh, wow.

Sid Yadav (0:56)

I got into tech at a very, very early age. So I actually had a blog that competed with TechCrunch, Mashable, ReadWriteWeb way back in the day. I was also Mashable's first writer, by the way. And I started building products after having written about maybe 3,000 startups on the blog. I'd write five to six posts every night from New Zealand. And New Zealand's time zone, by the way, worked very well because it was daytime in the US. So my journey really started back in New Zealand when I started building products. I actually sold that blog, got a consign degree, and then I immigrated over to the US when I was 20

My parents, by the way, were super confused. They're like, hey, we put in all this work, all this effort in moving to New Zealand, which is literally heaven on earth, why the move. But for me, it was all about being at the center of technology, all of the entrepreneurs that I wrote about, the startup ecosystem, all of that was in the US. And then when I was in the US, my second job, so my first job was a seed state startup, I was like the first eng design jack of all trades hire. That startup did not work out, but I think I learned probably the most in my life during those two years.

After that is when I joined Teachable, I was on the founding team as one of the first eng hires, I was the first designer, stayed for five years, as it happens in hyper growth startups, your role changes every six to nine months. So I went from eng designer to lead designer to product manager to VP of product.

And then about five years in, we were at this very interesting juncture where I thought Teachable was doing reasonably well as a company, we were now at maybe $25 million in ARR.

And I felt like I was at this very interesting time in my career where I thought a lot about why did I even move to the US? Why did I get into tech, right? Is it really to be a VP of product? I had an amazing company, but that constraint always kind of like was at the back of my mind of didn't I put in all the work to immigrate to the US to actually be an entrepreneur, to start my own company?

And additionally, I had the constraints, which is by then I had a wife, I had a four year old daughter. And so I couldn't really leave my job overnight and just start my own company. So that's really where the kernel of doing the next thing started for me.

Ayush Jaiswal (3:29)

How important it is for people early on in their careers to take up challenging roles like this, where the startup is small enough where you can get that flexibility and has the potential so that you can actually make meaningful impact as well. Like if there are young people who want to start up, let's say in future, what's your take on it? Like your experience?

Sid Yadav (3:52)

Yeah, I think it really depends on how you're hardwired. Like for me, I've been actually a founder CEO since I was 14

Even when I ran my blog, I did payroll management for five writers who wrote for me internationally. And I don't know if everyone's wired that way, right? But for me, it was like, it was always the default, kind of always thinking about, you know, how to start a company, how to grow a company, you know, how to make a meaningful impact in the world, right? So when I joined Teachable, what I told him was, look, I'm not the best designer that you can hire. I'm not the best engineer, far from it.