A Product Market Fit Show | Startup Podcast for Founders
00:00:00 · Alex Halliday, Pablo Srugo, S2
[00:00:00] S0: So I was talking to Sam Altman before ChatGPT was a thing and I said, "Hey, what's got you excited at the moment?" Or some vague question like that and he's like, "the AI stuff's getting really good." And I had no frame of reference for LLMs. We got to a million in Q1 of 2024, and then we hit thirteen in Q4 of 2025. It was the machine starting to work, the positioning getting better, as I mentioned, and just it really clicking with the market. [00:00:27] S1: When was the moment when you felt you'd found true product market fit? [00:00:30] S0: I think when I stepped away from the business for a week and we closed $300k or $400K in new ARR. And I came back, and I had nothing to do with any of those processes. [00:00:43] S2: That's product market fit. Product market fit. Product market fit. I called it the product market fit question. Product market fit. Product market fit. Product market fit. Product market fit. I mean, the name of the show is Product Market Fit. [00:00:55] S1: Do you think the product market fit show, has product market fit? Cause if you do, then there's something you just have to do. You have to take out your phone. You have to leave the show five stars. It lets us reach more founders, and it lets us get better guests, thank you. Cool, man. Well, Alex, welcome to the show, dude. [00:01:12] S0: It's great to be here.
00:01:12 · Alex Halliday, Pablo Srugo
[00:01:12] S0: It's great to be here. [00:01:13] S1: So you just raised a $40 million Series B from Greylock not too long ago, and you're in this world of which there's a few players. So we're actually going to talk about what you do differently and even just maybe broadly about competition. Because it's a huge topic these days but what you do is you help, kind of like there's SEO to rank up on Google, and now everybody's trying to rank on all of the different chat apps. Whether it's ChatGPT or Claude or Gemini, and you help companies do that. So, we'll get into how that all started. Maybe that's a good place to start, tell me a little bit about what you were doing before you started AirOps. Just give me that context. [00:01:47] S0: Yeah, for sure. I mean I've been in early stage companies for now about eighteen years. I got started pretty young. First half of my career was spent as a founder in the UK. I ran a social networking platform for five years. We had about fifty employees. We were battling Marc Andreessen's startup at the time. Can you believe it? And then I went to San Francisco. Originally for six months, ended up staying for ten years and during that time, I was the first product hire through to an established product design engineering org for three Series A companies. And I took them all through Series CD, including MasterClass. Which is the one most people have heard of. So I've always lived at the kind of intersection of product growth and engineering. That's where I'm meant to be in the world. [00:02:33] S1: And when did you start AirOps?
00:02:33 · Pablo Srugo, Alex Halliday
[00:02:33] S1: And when did you start AirOps? [00:02:35] S0: We actually incorporated the company during the pandemic, and I was building with my co-founder for a full almost two years before we raised any money. And this was nights and weekends, tugging ideas, playing with things, and also forming the relationship. Because, you know, I've had many co-founder relationships in my life, and that is the bedrock of the whole thing. So we founded in 2020, but we ended up raising money and really finding our initial team at the end of 2022. [00:03:01] S1: Just tell me a little bit more about maybe the origin story for AirOps specifically. How did you decide to get into the space?
00:03:01 · Pablo Srugo, Alex Halliday
[00:03:01] S1: Just tell me a little bit more about maybe the origin story for AirOps specifically. How did you decide to get into the space? [00:03:06] S0: Yeah, so we actually spent a couple of years in the idea maze. So the initial area we were exploring was really building for ourselves. Having run incredibly complicated teams in marketplace businesses and the fact that our teams never had the right data at their fingertips to run their roles. So we were dealing with product teams and frontline teams. It was just this mess of spreadsheets and CSVs. So we actually initially built a workflow tool to help those users and basically help us in a form of life. And that was a good six to nine months of building in that space. We launched a couple of products with different takes on the problem. We got our first ARR from our first few customers and then right in the middle of 2022, we actually started, I actually started playing with the early OpenAI models. So I was talking to Sam Altman before ChatGPT was a thing and I said, "Hey, what's got you excited at the moment or some vague question like that." And he's like, the AI stuff's getting really good. And I had no frame of reference for LLMs. [00:04:09] S1: Did you know Sam or is that an event or what? [00:04:11] S0: I knew Sam, yeah. So we met when I first moved to San Francisco, walking down the street. Actually, during San Francisco Pride. We were just wandering down the street with ten thousand other people and he was walking next to me. We got chatting. We've been friends ever since.
00:04:11 · Alex Halliday, Pablo Srugo
[00:04:11] S0: I knew Sam, yeah. So we met when I first moved to San Francisco, walking down the street. Actually, during San Francisco Pride. We were just wandering down the street with ten thousand other people and he was walking next to me. We got chatting. We've been friends ever since. [00:04:25] S1: No way! That's just crazy coincidence. [00:04:28] S0: Yeah, it's crazy. Well, that time in SF as well, you just would walk into a coffee shop and Jack Dorsey would be there or Kiefer Boyce or Peter Thiel. I look back now and I realize how insane it was. But yeah, that was the origin story there. So he got me onto LLMs, and I just totally fell down the rabbit hole, and the business started moving in that direction. And that was kind of one of the big inflections in the business that changed its direction. [00:04:53] S1: Yeah, tell me more about that time because I can imagine as you're playing around with these tools is right before ChatGPT. On the one hand, I'm like, yeah, I could see how you play around. You're like, wow, this is so impressive. It's not that easy to connect that to a business opportunity, like you figure out, OK, here's how I'm going to use this. What were some of your initial guesses?
00:05:12 · Alex Halliday
[00:05:12] S0: Yeah, it's such a good point. I remember I was on a plane flying to Atlanta and I was like, OK, I'm going to go do this. I'm going to try this OpenAI thing and sign up for an account. So I remember my first few prompts I put in were actually around SQL generation. It was like, can it create credible SQL for actually working with Shopify stores randomly? That was my initial throw at it and when it started coming back with kind of joins and, let's say, plausible SQL in those days. I just felt like the laws of physics that govern software were changing. It was just one of those moments where you're like, wow, there's this general purpose intelligence, and I didn't really have. Honestly, a fantastic business case for it back then. We started applying it initially to generating SQL and explaining data tables for customers. We released a little Chrome extension on Product Hunt. We started, you know, just kind of creating little experiences for existing customers. But there was this pulling of a thread that took us about six months that led us to our eventual customer, which were marketing teams. But what I realized was that there was going to be this explosion of use cases and businesses that would use this technology. And for me as a founder, the idea of being truly horizontal and trying to do everything for everyone just kind of lowkey terrified me. I remember feeling very strongly that we needed to pick a customer that we wanted to build for a decade and we had people using our tool in all these different ways. And I just looked at this map, and I felt if we try and serve all these people, no one is going to be happy. So we ended up picking marketers. It was a great choice. They found us, and then we doubled down on them.