Rebuilding Customer Support for the AI Era

Harj Taggar 0:00 [upbeat music]

Harj Taggar 0:05 Hi, everyone. Uh, I'm excited to be joined here today by Marty, Robert, and Advith, the co-founders of Pylon. Pylon went through YC in the Winter '23 batch, and is one of our fastest-growing companies over the last few years. Uh, I think what's especially exciting about their story is they took a while to find the idea and pivoted through several ideas, so we're gonna chat about that today. Uh, guys, thanks so much for joining us.

Advith 0:27 Thanks, Harj.

Harj Taggar 0:28 Why don't we kick this off by just telling us, what does Pylon do? What's the problem it solves?

Marty 0:32 Yeah. So Pylon is an AI customer support platform specifically built for B2B companies. We replace products like Zendesk, Intercom, Salesforce Service Cloud, but very AI-native and built for a B2B persona.

Harj Taggar 0:43 Could you give us a, uh... Share anything, um, to give us a sense of the scale that Pylon operates at today?

Marty 0:48 Yeah, so I think we're 79 people as of this week. Um, we're three years old, uh, three years since, uh, we spoke to and met you, Harj, um-

Harj Taggar 0:56 The Winter '23 YC batch.

Marty 0:57 Winter '23, and yeah, I mean, back then, it was just the three of us. Um, we actually pivoted through many ideas, as, as we'll talk about. But, uh, yeah, 79 people today, three years old, um, eight digits in ARR, uh, and last year we grew 5.35X.

Advith 1:12 Over 1,000 customers now.

Harj Taggar 1:13 Nice. Can you mention any of the biggest customers you have?

Advith 1:16 Yeah, folks like Honeycomb, Linear, Incident IO, Applied Intuition-

Marty 1:21 Deel. Yeah.

Harj Taggar 1:22 And how many rounds of funding have you raised?

Marty 1:24 Um, so we're Series B now. We've raised 51 million total from, of course, YC, General Catalyst for our seed, Andreessen for our Series A, and Bain Capital Ventures for B.

Harj Taggar 1:33 Cool. I wanna come back to sort of Pylon as it is today in a little bit, but I actually think what's really interesting about your story is it took you a while to arrive at this idea. Um, so why don't we kind of actually go all the way back, and maybe just tell about- tell us a little bit about each of you individually, so of your, your backgrounds, um, why you got interested in doing startups, and then maybe we can talk a little bit about how you started thinking about startup ideas.

Marty 1:56 Yeah. Advith, you wanna start?

Advith 1:57 Yeah, I can start. So I think... Uh, so Robert and I went to Caltech, and I think in college at least was when I first started getting interested in startups. I was considering being, like, a math major, and then when I went to college, I was like: "Oh, I guess I... Computer science is some applied version of math." And then met Robert freshman year doing, like, a puzzle competition. Um, we're both super into puzzles, and then we ended up running our school hackathon to- together for a couple of years, which ended up being basically like running a company, minus building a product. It's a lot of, like, organizing tons of people, raising money, just, like, holding an event, essentially. So like, building a team that does something, minus building a product. And so, uh, through that, uh, like, I guess, built the muscle of how to work together, with Robert especially, and then that-

Robert 2:37 Yeah. I think the funny thing is, we were, uh, work colleagues in college. Like, we weren't really friends. [chuckles]

Advith 2:42 Yeah, yeah. So we, like, had a great working relationship where we'd work on stuff. Like, Robert would take the night shift of, like, midnight to 8:00 a.m., and then I would take, like, the rest of the day shift, like answering emails and, like, doing all these, like, company logistics stuff. And then that summer of sophomore, Robert's sophomore year, he did this program called KP Fellows, which is this, like, entrepreneurial, like, internship program, and, uh, he was at DoorDash that summer, and I, I was interning in the Bay as well, but I just... That program has a lot of f- ex-fou- or, like, people who become founders later, and so got to see what was going on through that. And then the next summer, I did it, which is when I met Marty. I was interning at Slack. Marty was at Airbnb. And I guess the TLDR about why starting a company is just wanted to do it even in college, just didn't have a thing to do it about. And so, um, uh, like, a couple of years after, um, graduating, w- we were all at startups, and then I messaged Robert, like, right after the pandemic, being like: "I feel like I'm wasting my life." So my... It was on my 23rd birthday. It was like a existential crisis of a sort. Just felt like I wasn't really doing anything. I was getting bored, and messaged Robert and asked him-

Robert 3:40 That was on your birthday? [chuckles]

Advith 3:42 Yeah, yeah. We actually started our first meeting, like, on, on my birth- like, 6:00 a.m. on my birthday. Yeah.

Harj Taggar 3:47 One thing I'm actually curious about, um, quickly is, so you both- you... Remind us, where were you doing the internships?

Advith 3:52 I was at Slack.

Robert 3:53 I was at DoorDash.

Harj Taggar 3:54 Yeah, so those are both great companies. And Marty, you were-

Marty 3:56 I was at Airbnb. Yeah.

Harj Taggar 3:57 Airbnb. Okay, so all three of you were at, like, fantastic companies. I'm just curious, like, um, why did you decide to start your own thing versus joining one of those companies?

Advith 4:06 I, I, I just felt like at ev- every internship I was trying to work at a smaller and smaller company. I actually just felt like I was wasting my time, for lack of a better word. Like, my main... Not to insult Slack, 'cause our- a lot of our [chuckles] products today-

Harj Taggar 4:18 [laughing]

Advith 4:18 ... are based off of Slack. But at that scale, it was maybe a couple hundred people, and, like, my core internship project was they were doing a rename from, like, calling stuff teams to calling stuff workspaces, and most of my project was literally rename [chuckles] like renaming, and I just thought it was-

Harj Taggar 4:34 Pre-AI.

Advith 4:34 I thought it was super waste of my time, and I actually quit. I, like, asked to leave the internship early 'cause I thought I was wasting my time. Yeah.

Marty 4:41 Yeah, I, I think on, on my end at least, um... U- so in high school, I actually wanted to be a musician to start, so I had, like, written an album. I was in a band. Um, and then I saw The Social Network, and I saw Pirates of Silicon Valley. So I actually feel like movies made- like, just opened up the idea, like, some sort of, like, visualization of, like, what starting a company could look like, and the fact that anyone can kinda do it with a computer, um, with no resources. So I was already, like, personally interested in, uh, programming, had, like, watched some YouTube videos, got, like, JavaScript for Dummies, like, from a garage sale at some point, and so, you know, was doing that. Uh, and then watching those movies kind of made it, like, real that, like: "Oh, this could be much more than just, like, a fun little hobby." Yeah. And, and one way we've actually all described it is, I feel like at some point we just realized we couldn't not start a company. Like, you're just, like, sitting, doing whatever we were doing at other companies, and it's like, you just, in your gut, you already know the answer, which is you have to go try starting something, and, like, nothing is gonna make you happy outside of that. Like, you have to just go try it, even if it's a mistake.

Harj Taggar 5:45 How about you, Robert? How did you know you wanted to-

Robert 5:46 Uh, yeah, I mean, I grew up in the Bay Area, so I've been surrounded by, like, tech startups my entire life. Um, I always imagined engineering as just like, like a hammer, and I- while I love hammering nails, I'd, I'd rather build a house than think about the house overall. Um, so that's always been my goal, and I think, like, every internship, I just kept going to startups or companies just to observe how people build companies and just, like, kind of gather up all the different ways people-... build a team. And I, the, and the, that's why the DoorDash experience was really cool, because I got to see, like, what a great, uh, company looks like at such an early stage. I really didn't start my journey, um, full throttle until Advith did reach out to me that one night. I was like, "Sure, let, let's do it." [chuckles]

Harj Taggar 6:27 So yeah, just talk us through the story that, like, after you reached out to Robert, then talk us through what happened next, and how the three of you came together.

Advith 6:34 Actually, while I was- w- at that point when I was reaching out to Robert, I was living with Marty. So Marty and I were roommates after we graduated.

Robert 6:40 At that time.

Advith 6:41 Uh-

Robert 6:41 No.

Advith 6:42 No. Or we were-

Robert 6:43 It was during COVID.

Advith 6:43 It was during the pandemic, so we might have moved away for a bit-

Robert 6:45 Yeah

Advith 6:45 ... but, like, yeah.

Robert 6:46 Yeah.

Advith 6:46 So Marty and I were roommates after we graduated, uh, for, like, a couple years, and Marty has w- had already, I think, taken the plunge before that, and, like, had started trying to do his own thing separately. At that point, I wasn't... I guess I wasn't ready to... I felt like Samsara, the company I was at, doing really well, so I wanted to just do it on the side for a bit. And so, messaged Robert, and, and then we started basically every morning... Or I guess it started at a weekly cadence, just, like, brainstorming. And then it very quickly turned into, like, user discovery, where we tried to turn to, like, the first set of people that, um, basically are good candidates for user discovery, based on, like, this book, The Mom Test. I think, like, YC's super all about too, and that was school administrators for us, 'cause we spent a bunch of time running our school hackathon. So we reached out to a bunch of the admins at school, just asking them what their problems were, and we landed on one problem that's not really a problem, [chuckles] but, uh, we thought it was a problem at the time for, like, the career center. The lady who runs the career center was someone we worked with a lot when we were in college.

Harj Taggar 7:39 Mm-hmm.

Advith 7:39 And so yeah, it was basically, can we build a tool, like an alumni portal, so that students who have already graduated can reconnect with alumni for, like, career advice? And yeah-

Robert 7:47 And we made all the mistakes, uh, going through Pivot Hell. Like, we built it before really validating with anybody. We were trying to build something in edtech, which we know is, like, a probably a bad space to start out in. Um-

Harj Taggar 8:00 And you guys were working full-time jobs at this point?

Advith 8:02 Correct.

Robert 8:02 Mm-hmm.

Harj Taggar 8:02 Yeah, I mean, a question I feel like we get a lot at YC is, um, from people who want to start a company someday, is, "How do you do that? What does that look like day to day?" Like, you're working a full-time job, and you're trying to make progress on an idea.

Robert 8:13 Just... I think we were f- really fortunate because it was COVID, so that because everything was remote, we [chuckles] could actually take a lot of the calls-

Advith 8:19 There's a lot from home

Robert 8:19 ... on the side. Yeah, yeah.

Advith 8:21 And I think at that point, at least I felt like I had gotten pretty good at my normal job, uh, if that makes sense, and so, like, could still be pretty effective without, like, putting in the same amount of time. And so we started with early morning calls. I remember at, like, 6:00 a.m. we would talk, and then at night, and then it was, like, on a weekly cadence to start, and then it became daily. And then we started filling in all of the empty slots within our days with essentially customer discovery calls.

Robert 8:42 Yeah, I remember my coworkers would make fun of us, 'cause we had a calendar event called Grind Time.

Advith 8:46 Oh, yeah. [chuckles]

Robert 8:47 And they'd be like, "What is that?" [laughing]

Harj Taggar 8:48 [chuckles] Sure. And Grind Time is when you work on your startup ideas?

Robert 8:52 Oh, yeah, when... Yeah, yeah, yeah.

Harj Taggar 8:52 Oh, yeah. Um, how about you, Marty? How were you, um, exploring ideas to them?

Marty 8:55 Yeah, so I think a, a little before, um, you guys started messaging, working on stuff... And first off, I wanna call out, like, um, I feel like none of us were sitting still at any point. Like, I... Advith was making, like, a card game with someone else. Like, you built an escape room while we lived together in India. So I feel like even, like, while working at full-time jobs, I feel like all of us were probably doing something. Um, and so yeah, for me, I was at Airbnb for maybe, like, a year and a half, and I was just, like, kinda miserable. I was, like, looking around myself at everyone else, and I was like: Okay, do I wanna be an engineering manager? Do I wanna be a VP one day? Um, like, who around me would I trade places with? And the answer was no one. I just wasn't interested at all in switching roles with anyone who was ahead of me career-wise. And m- at the same time, I was looking at founders who were just kind of, like, pivoting around and, um, trying to build companies, and I still, like, thought that looked way more exciting. And I was like, "Damn, if I spend, you know, the next five years just working my way up at Airbnb, I'm- I already know I'm not gonna enjoy that outcome." At the same time, I'm looking at founders, even if they're not that successful, and just saying, like, "I'd switch places with them." So, you know, during Airbnb, I started doing, like, side projects with all sorts of people, many different sets of co-founders, um, and many different projects. Like, everything from, like, like, a dentist app thing to, uh, like, a 3D clothing manufacturing thing. Um, like, ev- anything I can think of.

Harj Taggar 10:20 Were there any differences in, like, your approach to testing out startup ideas early on versus the two of you?

Marty 10:26 Um, I'm guessing that... We haven't talked about this explicitly.

Robert 10:30 No.

Marty 10:30 Um, I think I, I can explain at least my philosophy, which was, like, find any problem [chuckles] and then just try to see if you can solve it. I think for me, well, one, you kind of, like, look at your own problems, and then, like, comb through that list. Uh, I feel like quickly you run out of things. Um, I feel like I didn't have that many problems that weren't, like, fun-oriented back then. Um, and then I started, like, just talking to people. And so for example, like, this, like, 3D, like, clothing printing thing was, uh, the... One of my friends who I met, um, in, in SF, he, like, h- had an idea related to that, so, uh, he came up with that. Then there was actually one of our ex-roommate's, um, ex-girlfriends was in dental school, and so, like, I started talking to her about, like, the, that dental thing. Um, and then eventually, at least for me, I realized I was only gonna make so much progress while working full-time at Airbnb. I, I wouldn't say I was, like, in a place where I was so comfortable that I could just, like, easily not work that much, and it was still in person. I think during the pandemic, like, you could just be at home.

Robert 11:32 Yeah.

Marty 11:32 For me, I just realized I'm miserable at work. Um, I actually have enough money saved up to, like, take some risk, and then I... This was really helpful for me. I just, like, made a, like, best outcome, worst outcome doc, where I was just like, "Here's, like, the best thing that could happen if I leave Airbnb and try to start a company." And so, you know, wrote out, "Okay, it goes really well, like, make a bunch of money. Like, I love the job, and I no- I don't look back." The worst case is, like, "Okay, a couple of years of opportunity cost to being a software engineer. Um, you know, I, like... Maybe I struggle to find a job again," um, but, like, realistically, it didn't feel that bad. I felt like I would just get another software engineering job two years later. So yeah, I think writing it out helped a lot to understand, yeah, what, what is, like, the worst case, and then also then, um, pairing that with knowing I was gonna be unhappy for sure if I stayed.

Advith 12:20 ... Yeah, I guess our process was, at least for finding ideas, it was kind of similar. It was, like, looking to the people closest that we felt like we could source problems from. I think we understood that we had [chuckles] no problems ourselves to, like, actually solve. And so, and luckily, we had been working for a few years, so there was... I think we made a long list of stuff related to what I was working on at Samsara, what Robert was working on at Affinity, and tried to, like, explore those threads. They ended up not leading to what felt like the biggest possible opportunity, but-

Robert 12:45 I think the cool thing is, like, of all those ideas that we had looked through, they do end up becoming good companies, uh, in some respects. Because a lot of our customers today were also ideating on the same ideas, and then they did get somewhere with them. So we- I think one of the conclusions that I've pulled from it is, if you're very good, and, like, diligent, and can grind it out, you can probably get some idea somewhere, uh, to some successful point, so.

Advith 13:11 So then, yeah, through each of the iteration process, we learned something. Like, the first idea, we learned to not build something before we, like, have very clear validation. And I, I, I think for each of- e- each successive idea, we just refined our process for, like, how to validate an idea.

Robert 13:24 Yeah.

Advith 13:25 Yeah.

Harj Taggar 13:25 Um, and then how did the three of you come together and decide to team up to find ideas?

Marty 13:30 Yeah, so I had left Airbnb, worked with one guy for a year on a health tech idea. That didn't work out. Then spent six months, um, working with another guy, who is at- actually still at Airbnb, and then, you know, six months in, he's- it's clear he's not gonna leave Airbnb. So it's like, okay, back to the drawing board. I personally learned during that experience that co-founders matter a lot, and to be honest, I just didn't care about the idea that much anymore, personally, and I was just looking through my network of, like, who are people who I would just want to work with? And I'd lived with Advith for three years before, um, I considered him one of my best friends. And I was like, "Okay, like, we've never worked together, but this is someone I think it would be really fun to build a company with." And so I reached out to Advith, um, and then what was going on for you guys at that time? [chuckles]

Advith 14:11 Yeah, Ro- Robert and I were, were working together, and, um, it basically felt like since we're at this stage pre-idea, that it was actually counterproductive to have even more people trying to brainstorm together, and so it felt like not the right time, and it felt more like, oh, once anyone has something that might actually be a- an idea, let's all pile on, type thing. And so we were reluctant, for sure, at first, [chuckles] to, like, all work together.

Robert 14:32 We rejected him. [laughing]

Marty 14:33 Well, well...

Harj Taggar 14:33 [laughing]

Marty 14:33 No, no, no, no.

Advith 14:34 Be truthful.

Marty 14:34 It was, it was even worse than that to start because they were vague about it. [chuckles]

Advith 14:39 [chuckles]

Marty 14:39 They were like, "Oh, yeah, sounds great," and then, like, crickets for, like, the next two weeks. And I'm like, "Like, okay, so, like, when are we doing this?" [chuckles] And they're like, "Oh, like, what do you mean?" [laughing]

Advith 14:49 [chuckles]

Marty 14:49 And being super vague and, like, not direct communicators about the whole thing, [chuckles] which I feel like has been a trend for us continuing.

Harj Taggar 14:57 [chuckles]

Marty 14:57 But a- at least for me, I was like, okay, this is, like, uh, at, uh, the top of my list, um, you know, working with Advith, and then I started getting to know Robert through, um, our conversations. And they basically said no. I, I personally started just, like, continuing to work on ideas. Um, there were some that I tried to bring to them. Um, one actually that I feel like we spent way too much time in hindsight is the-

Advith 15:17 Met collection?

Marty 15:18 ... uh, no, the land idea.

Advith 15:19 The metaverse.

Robert 15:20 Oh, right. [chuckles]

Marty 15:20 [chuckles] This was, like, when crypto, like-

Advith 15:22 [chuckles]

Marty 15:22 ... the metaverse stuff was, like, really big.

Advith 15:25 [chuckles]

Marty 15:25 And so there was this, like, one investor in LA, and I was in LA at the time, who was, like, trying to... He was like, "If you guys go build a company where you, like, sell digital land in the metaverse, I will fund it." [chuckles] And so I was like... We, like, explored that idea for a bit, and we're like, "Okay, where could that go?" So yeah, just stupid ideas in hindsight.

Harj Taggar 15:41 While we're on the topic, like, what did you all learn, would you say, during this process about co- like, finding co-founders, especially at that earlier stage when you're trying to figure out the idea to even work on? Like, what, what works and what doesn't?

Advith 15:52 We learned the same thing that he just said, which is, like, you shouldn't base your, uh, co-founders based on the idea. There were several iterations where we were, like, about to start this company in the logistics space. We actually feel like we validated the problem, and we, we felt like what was missing was, like, sales experience in the logistics space or some entrenched network. And so we were considering co-founding with these, like, two other guys who were just, like, deep logistics, like, sales veterans, and we just n- we actually just could never acquire, uh, end on an equity split that made sense, so we're actually quite close to, to-

Robert 16:20 I don't think we ever built trust enough in them, either.

Advith 16:22 Yeah, just, like, couldn't, and-

Robert 16:23 They were just too different of people.

Advith 16:25 Yeah.

Robert 16:25 Um...

Advith 16:25 And so I think we reached the same conclusion, that you wanna pick someone you wanna work with, and that you will have a good relationship with, not-

Robert 16:30 Especially if you pivot the company, and the idea changes off of that industry, then those people don't make any sense anymore. So you just wanna work with people who long term you can actually work with.

Marty 16:39 Yeah. That's something I learned with a first co-founder I was working with. He was, like, very related to the idea, and we were working on, like, a Parkinson's app, and he, um, was, like, very involved in that community. And so that was the only idea that it made sense to work on him with, and so, like, I think that also prevents you from pivoting later when you should, right? 'Cause you kind of, like, start realizing it's not working or struggling, and then, like, you're just like, "No, we have to..." You, like, kind of are focused on that. I actually think that's one of the reasons that passion is not, like, the best reason for starting a company, too, passion for, like, an idea or space. Because it might blind you to building a big business, if that's what you actually wanna accomplish.

Harj Taggar 17:14 Yeah, what do you... 'Cause so much of the common advice in the, the, to, um, [lips smack] original YC advice is around, like, you know, make- solve your own problems, make something you want-

Marty 17:23 Yeah

Harj Taggar 17:23 ... like, be the user. Um, over time, it actually feels like so many more of the startups are successful with solving someone else's problems.

Marty 17:30 Right.

Harj Taggar 17:31 Like, what, what do you think about that advice and, and how it applies?

Advith 17:32 Yeah, I don't think it's important, either, because I think if you're intellectually curious, it's pretty easy to put yourself in the shoes of a user that you haven't been in the past. Maybe you, like, have some, like, built-up unique insights if you happen to have, you know, lived that problem for a long time. But you can speed-run that by just, like, being super deep in the space, I feel like, so.

Marty 17:48 I, I also... I mean, we aligned early on some of the key reasons of... or the key components of, of building a company. So first off, like, the motivation for building us- it for us, um, a lot of people will say, like, "Oh, money," or yeah, "Passion about this space," or, like, maybe there's some, like, ego thing. I think for us it was very clear it was motivated by fun and adventure. So, uh, it was just, like, exciting, right? It was just like, that's the most fun thing that we could come up with doing. So the why was pretty aligned between all of us. Um, the what, so we definitely wanted to build a big, fast-growing company, and it didn't really matter, like, what the company did.... um, so I think that, that's actually a superpower in some sense, because then if you know you just wanna build a big company, it doesn't matter what or, like, which industry, then, um, you can just, yeah, clearly, like, work backwards from, from that outcome. And then, like, the how is also really important for us. So of, like, we wanted to build kind of like, the, "Hey, live together," like, "grind it out really hard." And, like, even the people you guys were considering working with, right, in the logistics space, were definitely gonna be like: Hey, like, kind of live separately," which sounds normal for everyone else, but that's, like, not the vision that I think a- any of us had for-

Advith 18:53 Yeah

Marty 18:53 ... starting a company together, yeah.

Harj Taggar 18:55 Um, one of the approaches I've had to sort of finding ideas is you start by, um, at least defining, like, the attributes of the type of idea you would want to work on. Like, um, Drew Houston used to give this talk at YC constantly about how he found the Dropbox idea by... He didn't know what the idea was, but he knew he wanted to d- build something that he would use himself, that was a deeply technical problem, that, um, monetized, like, from day one.

Marty 19:17 Mm.

Harj Taggar 19:17 Um, did you guys do anything like that when you were brainstorming? I'm just curious what, what your thoughts are on that.

Marty 19:22 Yeah, I think we iterated, like, a lot, uh, in terms of the i- uh, like, what type of idea. So I, I guess, like, one component is, okay, we wanna build a really big company. Um, we definitely were-

Advith 19:31 What does that mean, though?

Marty 19:32 Yeah, exactly. Exactly. So defining it more explicitly, these days, we'd tell you, like: "Okay, we work backwards from a billion dollars in revenue or a $10 billion company." Um, and so we actually looked at public, uh, companies, uh, public B2B SaaS companies at the time, who were worth over $10 billion.

Advith 19:47 Hey.

Marty 19:47 And turns out, there aren't that many. Um, there were, at the time, 26 of them. Um, and so when you look at that list, you're like: "Oh, shoot, that's, like, not a lot. How do we, like, understand why they got to that size?" Um, and so-

Harj Taggar 19:59 And what does that... How do you do that?

Marty 20:00 Yeah, so I mean, this, this then goes back to, like, when we came back with our ideas, right? So when we f- when we started working together, uh, I had one idea I was working on. You guys had an idea. You were working on the logistics one. And this is actually, I think, such an important part of the story. The fact that we came together with different ideas and had to battle test them against each other was actually so helpful, because-

Harj Taggar 20:20 Ah, ha, so you were, you were all sort of, like, researching your own ideas-

Marty 20:22 Yeah

Harj Taggar 20:22 ... and digging into markets-

Marty 20:23 Yeah

Harj Taggar 20:23 ... and then convening together-

Marty 20:25 Exactly

Harj Taggar 20:25 ... to, like, debate them?

Marty 20:26 'Cause then it was like, they were excited about their idea, I was excited about my idea, and then it's like: "Okay, which one should we work on?" And so then we literally- we spent, like, I think, like, probably half a day, one day, maybe, working on, like, the, the fintech idea I had. And, and we spent, I think, more time on the logistics idea, but then we literally made a Google sheet. I, like... I've looked back on this a couple times. It's really fun. Uh, with, uh, we started with two tabs. Tab one was this fintech idea, and we did a bottoms-up analysis of, "Hey, like, how big could this company be?" And so the conclusion was, like, if we, like, crush it, it's gonna be worth, like... or we will make t- high tens of millions in revenue. Then we did the logistics one. If we crush it, we're gonna make, like, hundreds of millions in revenue, and that's, by the way, the whole market. And then finally, we had this impression that, like, B2B SaaS, or, like, something that you could sell to any company, was kind of an end state for a lot of people who were pivoting. They try, like, all sorts of, like, v- verticals and then just, like, eventually pivot to some sort of horizontal SaaS category. Um, and so we took Rippling as, like, a model company and made, like, a third tab for them, and we're like: "Okay, like, how big can Rippling be? And what- how... If we did the same exercise for them, how big is their market?" And what we realized was actually their market is orders of magnitude bigger than, like, the things that we were looking at. Like, you just take, like, everyone who gets paid and multiply them times a subscription, and it's like, holy crap, that's like... It, it's clear why some companies can be so much bigger, is you will, you will inherently just be capped by the market you choose initially. And so then it, it was kind of like, I think there was a little bit of sadness for... It's always sad when you, like, invest into an idea and you're like-

Harj Taggar 21:55 But-

Marty 21:55 ... oh, like you think it's gonna work.

Harj Taggar 21:56 On that note, like, you were at Airbnb. Airbnb is, like, the classic example-

Marty 22:00 Yeah

Harj Taggar 22:00 ... of the same timing with-

Marty 22:01 Right. No, no, but, but the thing, the key thing here is, like, it, it's, it is an established big category, right? Travel is a huge category. And then, so and this is an important dimension. It's like, okay, there's the, the big category that exists already, um, and then there's some sort of emerging trend within it, which ideally we could latch onto and then grow with in an existing market. And so, like, uh, Airbnb is a great example of this. Um, cr- like, Bitcoin would be a great example of this, where, hey, you'd say crypto is small, but crypto is, like, part... It's like the emerging way of doing things, potentially, in financial systems-

Harj Taggar 22:32 Like moving money around, yeah

Marty 22:32 ... money, like, and that's a massive market, right? And so you kinda latch onto the emerging trend within the really big market, and your bet is that that emerging trend is gonna grow really fast. And so for us, like, okay, we kinda looked at all these, like, bigger SaaS companies. Um, the, the biggest company on the list was Salesforce at the time, um, like, $300 billion market cap, and one thing that was really interesting... I can't say, like, it really played out exactly like this, but it's a nice story. Like, uh, Sal- [chuckles] it turns out Salesforce, like, their biggest revenue driver was actually Salesforce Service Cloud, which is their customer support platform. So everyone knows them for their CRM, but actually, their biggest revenue driver, um, I think as of the end of last year, um, $10 billion in revenue for, um, Service Cloud.

Harj Taggar 23:11 Mm.

Marty 23:11 And that, that's their, where they make the most money. Um, and so yeah, kinda looking at those companies, like, realizing we needed to be in something more horizontal, wanting to, uh, work on, like, kind of a, a big, a must-have pain point as well. That's, like, something we investigated a lot. Um, and then yeah, so big market, emerging trend, and then, yeah... Do you guys wanna talk about, like, how we explored from there?

Advith 23:32 Yeah.

Marty 23:32 Yeah.

Advith 23:32 One more thing is like, yeah, we were pretty focused on B2B, because it, uh, basically, in B2B, you can actually reason about why someone would buy your product. It feels like you're actually solving a specific pain point, and so, like, it's... y- you can, like, convince yourself more easily that the thing you're building is, like, a, an actual, like, thing that people need. And then also, if you're in a general s- large space, you can, like, not know the huge vision at the beginning and still expect to be a large company, because you can kinda pivot, or mini pivot, or gradient descent into, like, whatever the massive thing in the space is. And so as long as you have some beachhead in, like, a large space like B2B or, like, some functional technology in B2B, then you can end up with somewhere big, and so you don't have to know the end state before you start.

Marty 24:11 Yeah. Oh?

Robert 24:12 I think it's also important to dig into, like, the why now, and that was very important to us, to try and figure out, like, why companies succeeded at any point in time. We like, like looking at all the anecdotes and all the different examples, like Salesforce having Cloud to beat out Siebel System, and that's why they ended up winning. For us, the why now ended up being realizing that companies talk to each other over Slack, but, like, we didn't even realize there were other why nows, uh, that helped us, helped propel us, and I think, like, now- nowadays with-

Marty 24:39 ... YC companies, AI is like the why now, but we didn't even know that would be a thing, uh, back when we were pivoting.

Harj Taggar 24:45 So let's go, so, um-

Marty 24:47 Yes

Harj Taggar 24:47 ... talk us through the story of actually arriving at the, um, Pylon idea, customer support, um, and maybe where does YC fit into that arc?

Advith 24:56 Yeah, I guess the way the idea came about is we were just talking to a bunch of people. One of our friends basically said they were facing this problem at their job. Essentially, this idea that they were talking to all their customers over Slack, which is a very new thing, and, like, that meant they couldn't, like, scalably reach out to all their customers, and they were losing track of all their messages. And for whatever reason, that felt like it resonated as like a, a kind of world view shift of, like, how people are operating, and it, it... Like, it was easy to draw the through line of, oh, a bunch of, like, the way you do your kind of customer processes would start breaking. And then we all gathered around that, hit up our whole network of, like, startup folks that we knew. It seemed like a bunch of people were actually at that very moment in market for a solution because they were like, this why now was a problem they were facing, and so that was very compelling. And the people who were not felt like they were on the right trend line. Like, you could see that in the future they would run into the problem, or they were bought into, like, this way of operating, which felt like it would lead to problems later on that we'd be able to solve.

Marty 25:48 Yeah.

Advith 25:48 Yeah.

Marty 25:49 And, and tactically as well, like, one thing we did when we... W- we, we wanted to focus on one type of persona as well, and so we did try to look at, like, post-sales roles. I forget how we concluded on that exactly.

Advith 26:00 I think we thought, like, these type of roles were newer-

Marty 26:02 Yeah

Advith 26:02 ... and so it was, like, another why now depe- dimension. People like solutions engineers or customer success managers felt like newer, th- newer as a concept. Yeah.

Marty 26:10 And, and so what we ended up doing, each of us, every day, we'd wake up, and we'd DM people on LinkedIn. At the time, it was, like, 40 max, uh, like, connection requests that you could send per person, and so every morning, that was, like, our first task. So 40 messages each, uh, personalized. We'd go on LinkedIn and, and just message people, and it was basically something along the lines of, "Hey, you know, we're founders who are pivoting around. Like, we- we're trying to learn more about, uh, solutions. Um, do you have 15 minutes to, to chat?"

Harj Taggar 26:35 Do you have any opinion on... One of the common questions I get asked is, um, is it better, like, for exploring ideas, is it better to do that, "Hey, we're pivoting, we're trying to learn more about customer support," or is it better to say, "Hey, like, here's a solution. We'd love to sort of pitch you on it and, um-

Marty 26:49 Yeah

Harj Taggar 26:49 ... and see how people respond?"

Marty 26:50 I think it depends on where you're at in the, like, ideation process. At that point, we literally had no idea. So [chuckles] we were just like, "Okay, like, this category seems big. We're looking for the trend within it." And so, um, we actually didn't have an idea to pitch at the time. Maybe there were, like, a couple that we were, like, floating around. I think, like, when reaching out on LinkedIn, it's good to, like, put some little nugget in there to, like, pique their interest-

Advith 27:11 Mm

Marty 27:11 ... and then that in and of itself is signal whether they actually accept the friend request or not. Um, 'cause the response rate on LinkedIn, it was like 1 to 5% or something like that.

Advith 27:20 Yeah.

Marty 27:20 It was, like, something abysmal, um-

Advith 27:22 Which is fine, though, 'cause imagine if you're messaging, let's say, like, 120 people, that's, uh, what's 5% of that? It's like-

Marty 27:29 Yeah, still-

Advith 27:29 ... o- over five people.

Marty 27:30 Which is pretty good.

Advith 27:31 Yeah, that's fi-

Marty 27:32 Yeah

Advith 27:32 ... you're booking your calendar for the next week, right? And so, um, it- at that point, you can, let's say, like, talk to 30 people that you're trying to, uh, do discovery with the, the next week. And so, yeah, we were basically, as Advith said, looking for these, like, new roles and messaging them. Um, we knew we were in, like, a bigger, broader category, and then, yeah, kind of like listening for problems. And to give you a sense of what we did on these calls, we would just be like: Tell us about what you do. Tell us a- about what you care about, what tools you use. Like, what do you hate about your job? What does your boss care about? What do you measure? Um, kind of like getting, like, the full landscape. And so I think when, you know, Advith was on that call with, with, um, uh, our friend of like: Okay, you know, they have this Slack problem, or, like, there's some vague problem around it. Um, we also could, like, look back at all these conversations we had and, like, oh, actually, like, no one mentioned this as an explicit problem maybe, but, like, it's clear that other people, like, kind of mentioned this in the periphery of, of what they were talking about. And so it, it did start to come together, um, after that one person explicitly was saying, like, "Hey, this is a problem." More tactically, I think we... It's useful to spend, like, 80% of the call, like, trying to dig into, like, some idea you already had, but then leave 20% for, like, them to just say random stuff that could seed, like, the next thing that you think about or, like, that's like, you know, uh, creates the next set of questions you ask to the next person. And also related is, I think, at least for me, it felt like a lot of the leverage of quit- at this point, we had quit our jobs, uh, entirely, all of us, and so it felt like the main thing we got from that is actually the ability to iterate every day versus every week, which that cycle time affects the speed you get to your idea a lot, I think, or way more than I would have expected. I would have thought before I could balance everything. But I think the issue when we were working while still at a job is we would only change the questions that we asked, like, every week, for the most part, and we'd be, like, in the same headspace during the week. And so changing your questions every day just means, like, you're actually iterating every day.

Harj Taggar 29:19 And you're doing so many calls at this point. You're, you're doing so much discovery work. Um, exactly what was it that people were saying was, like, the problem with Slack?

Advith 29:26 Specifically, what resonated for me at least, was that, oh, this is a new way... Like, this is changing how people talk to each other. Like, that feels pretty deep. Like, um, the- you never think of Slack as like a c- like a platform where you communicate between businesses. It's always historically been like, "Oh, I'm talking within my company." And so it felt like, oh, post-pandemic, everyone's moving online, so everyone's using these tools. Like, literally random businesses have to use some kind of tool to, like, talk both amongst themselves but also between each other, and so it felt like a big kind of shift in, like, how people operate. The specific pain point was like, "Oh, I have 100 customers, and I talk to them in th- over Slack. I have a s- shared Slack channel with them." Like, a simple use case of, "I have an outage. How do I let all these people know I have an outage if this is the way that I talk to them?" Like, "I have to literally go into every single channel and copy and paste a message." Like, you... The pain point is pretty visceral for even just that, even though it's, like, a pretty small slice of, like, what you would expect-... issues to arise, and if you assume this trend of people talking to their customers in this new way.

Robert 30:27 Yeah, it was pretty night and day in terms of passing the mom test. I think, like, all of the... I think each of us went to, like, one of our friends-

Harj Taggar 30:32 For people who don't know, what, what is the mom test? And then tell us how it applied here.

Robert 30:36 Uh, yeah, the mom test is essentially, like, uh, if you ask your mom, like, "Hey, would you buy this thing?" Of course, she's going to say yes. So you have to ask questions around it to see, like, whether she would actually buy your thing. [chuckles] Um, but to back out into the, uh, our idea and how we thought of it, like, we each went to one of our friends' companies, and we were like: "Hey," like, we mom tested them, and it pretty much passed with flying colors around, like, yes, they would buy something there. They're actively looking for something. They tried to build it in-house but couldn't do it. Like, they went out and looked for other vendors, but they were all kind of bad. So, like, it, it was pretty clear that, like, we could find, like, a bunch of customers in these first set of people. I think also, like, we had originally... Like, it was kind of, like, right in front of our face, too, at, like, our past companies, where we had kinda seen this, too, from, like, the vendor perspective, where our companies had Slack channels with customers. Um, and we just never thought of it as, like, an idea until that moment. Yeah.

Marty 31:30 Yeah. Also, I mean, um, to, to paint the picture here as well, so Advith, um, when he first spoke to, to, uh, this person on the phone and... Or spoke to this person who had this problem, um, he called Robert and I. Robert was, like, in a car ride from LA. I was living in a hacker house at the time. And so, you know, Advith's all excited. I think it's a Sunday night. You know, we hang up the phone. I, like, immediately... I was living in a hacker house called Mission Control, um, and I, like, went upstairs and spoke to another founder who was living there, Tejas, uh, founder of Hightouch. Um, and so I went up to him. I was like: "Hey, do you guys have this problem of shared Slack channel support?" He's like, "Marty, you're not gonna believe this, but we're actually looking for a solution right now."

Robert 32:08 Hmm.

Marty 32:08 And actually, that they had worked on the same exact idea. So right after he told me, "Hey, like, you know, we're, we have this problem," and explained it, he was like: "Don't do this idea. We tried it. It didn't work."

Robert 32:18 Yeah.

Marty 32:18 Um, and in fact, f- uh, fun fact about them, their name, Hightouch, is, uh, short for high-touch support, which was over Slack channel.

Robert 32:25 Yeah.

Marty 32:25 So it's, um... So yeah, basically, it took i- 30 seconds to find, like, prospect number one after that phone call, which, uh, was pretty incredible.

Harj Taggar 32:32 Since they had tried the idea, what's your advice to founders when they're... A common thing when they test out an idea is go speak to other people who have tried the idea in the past. Like, is that a good idea, or should they avoid those people?

Marty 32:41 You, you should definitely... I think it- there are so many reasons why ideas cannot work out, and I feel like most of the time it's execution, or, like, they give up, or, like, there's co-founder drama. Like, I feel like most YC companies, you could t- say this better than we can, is, like, co-founders break up, right? And it had nothing to do with the idea. I think one great example of this is during our YC batch, it was the first batch after ChatGPT came out, like, the most common idea was, like, AI for customer support.

Robert 33:03 Yeah.

Marty 33:03 And, like, almost all of those companies died. And, like, it's not like there aren't companies now that are doing really well as, like, AI support agents. If they had stayed with that, they could have been really big. Um, so I think there are all sorts of reasons. I counted at one point, I think we were... Are, like, the 13th company to try this exact idea.

Robert 33:20 Yeah.

Marty 33:21 And in fact, a lot of them pivoted away and are now our customers for this idea-

Robert 33:24 Nice

Marty 33:24 ... uh, which is quite funny. So yeah, I think... Yeah, I, I think you should definitely, like, think from first principles if you think the idea is good. Yeah.

Advith 33:31 Yeah, I think you just have to have a reason that it'll work for you, that it didn't work for other people, and that is enough. It, it could be that, yeah, some team died, or that you know way more about the domain, or, like, your execution's gonna be better. Like-

Marty 33:42 What was it for you guys with the-

Advith 33:43 The... I think it was actually timing was a big part of it, and I think our execution is, like, pretty solid as well. But, um, I think the timing was pretty big. The combination of, like, this trend of post-pandemic, a lot of these businesses are talking to each other, are forced to talk to each other in this, like, conversational way, plus conversational AI means you can, like, extract and make use of all of that data, felt like two great, like, kind of market signals. Yeah.

Robert 34:04 Yeah.

Marty 34:04 Yeah, even when we were in YC, we were very worried about timing. Like, I feel like we... This was one of the existential crises during that three-month period that we kept coming back to of, like: Oh, like, is it too early? Like, is the market big enough? Um, and so we, we asked these questions. I remember we spoke to, um, during office hours with you and, uh, Dave Lieb, and he was basically saying something along the lines of, "Well, like, you know, th- this is a risk. That's right. Um, the market might not be big enough yet, but, you know, hey, that's, like, a risk I'd be willing to make." [chuckles] And I feel like that personally gave us-

Robert 34:36 [chuckles] It's great

Marty 34:36 ... a lot of confidence, um, that, hey, like, you know, oh, if a YC partner is saying, like, that is fair, then, like, yeah, that's probably valid for us. But that was, like, constantly something that we thought about, and even over the course of the next year, you know, our, our first product actually wasn't a big platform or anything like that. It was actually just a very niche integration to help customers who have shared Slack channels, um, ticket conversations from there into a ticketing system like a Zendesk or an Intercom. So we actually, to start, were just, like, this integration. We built it in, like, a week. We, you know, got it running with, with Hightouch, uh, during that same period. Um-

Harj Taggar 35:12 Is it because that Hightouch said that, "Hey, this is the specific thing that we want?"

Robert 35:16 Yeah. Mm-hmm.

Marty 35:16 Yeah, and so that... Yeah, and there were many problems around, like, this new conversation happening, like, over, over new channels. And it wasn't just Slack that we saw. We saw Slack. Microsoft Teams was starting to become really big, so at the time, like, M- Microsoft was investing a lot there. Um, you know, Discord was becoming a place where communities are. Um, WhatsApp, already around the world, that's where a lot of B2B communication happens. Telegram. And so, yeah, we definitely saw this trend continuing long term, and not just across one channel, but many. So it did feel like, okay, all these, like, business workflows and systems that rely on email traditionally for B2B, um, that same data model of email no longer works for, uh, kind of these conversations and new channels.

Harj Taggar 35:57 You get the insight, you get the idea, you figure out the MVP v- for your first customer.

Marty 36:01 Yeah.

Harj Taggar 36:02 Then where do you go from there?

Advith 36:03 And right before the first customer, we basically sprayed... This is another leverage point for us specifically doing B2B, is that we've been in the startup world, I guess you could say. And so we- a lot of our friends are founders, or, like, we were able to hit up a bunch of people to quickly get validation, where maybe that's a bit of an unfair advantage for us specifically in B2B. And so we had hit up, like, 20 or so people, and either... Several people, one of- someone who had tried to recruit me for their startup, Robert's friend from Affinity, who had started his own company, all were in market for a solution. And so felt like the validation was obvious, and we had, like, an immediate set of early people that we could, like-... try to give our, our product, too. So yeah.

Marty 36:37 Yeah, and also, um, one thing, so when we were thinking about, like, working on specific verticals versus something more horizontal that any company could buy, regardless of what industry, um, there is an advantage in, hey, like, if we're selling something into customer support, that all companies need customer support, and so you can start in tech for us, which is an industry of early adopters, people we already know, um, and then eventually expand to more. And, and so I think, yeah, like, if you go into healthcare, if you think about it, like, you're gonna have to go to conferences, you're gonna have to build relationships. It's gonna take a long time to even, like, really, like, get your foot in the door. Whereas if you build something more horizontal that's more applicable to everyone, then you can start in, like, one... Yeah, start in whatever market that you have connections in.

Harj Taggar 37:16 Well, one thing with B2B you often have to think about is, like, the size and stage of company that you're going after.

Marty 37:20 Mm.

Harj Taggar 37:21 Like, how did you think about that early on?

Marty 37:23 Yeah.

Advith 37:23 Yeah, that's also, I think, very related to, like, whatever idea that you have. Like, um, it started off where our idea was almost this, like, additive thing that you could purchase, like, at any stage of company, and so we could sell to larger companies because you actually, in fact, need some amount of the pain to even need to buy a solution, AKA you have to have a certain number of customers, so it pre-selects for, you know, a, a certain size of company. And then, um, the core value prop there was, like, "I already use all these systems. I don't want another system, but I just want all the systems to work together. So plug in the place that I talk to my customers with my existing tools, AKA like Zendesk or Intercom." So it, it's just skewed towards larger companies to start. But then, like, a year in, we end up doing, like, this coming to terms with what we might be building, and that was like, "Oh, maybe we can actually be the core system in the space," where you have to start again, bottom of the market, and go up. And, um, like, inherently, you can't build the surface area required to, like, sell to someone bigger because you're trying to build this, like, core system of record maybe. And so then we started again with small companies a- and then built our way back up. So I feel like it's very much a property of the idea you're working on, and each one has their poisons [chuckles] yeah.

Marty 38:20 Yeah, I do think that a bit of it was luck, though, that we had a bunch of friends, and maybe this is speaks to our competitive advantages again. But, like, because we had so many friends at, like, the Series A through C companies, we were able to find a bunch of customers that actually had this as a burning need, versus a lot of the prior competitors had started in s- selling back into, like, the YC batch or something like that, where the pain isn't as great. So, uh, it just didn't look like a very appealing idea to a lot of other companies who had tried the idea.

Harj Taggar 38:46 Yeah, it's something that comes up a lot for us at YC. If you look at so many of the big companies that have done that, especially within the YC network, is, like, Stripe or, or, uh, Gusto, um, and they all really have this s- strategy. Brex is another one, like, are really selling into the batch, which made sense for those products because, yeah, taking payments, payroll, um, getting a company card are all things that affect people in the batch. But if you're, like, um, I don't know, if you're Fivetran, or if you, if you were building, like, ETL pipelines, uh, that you can't sell into the batch.

Marty 39:15 Sure.

Harj Taggar 39:15 And so, um, it's one of the things we spend a lot of time on with people is, "Hey, like, actually, like, you have to figure out, like, it's great to sell into the batch or s- early-stage start-ups, if that's who you have lots of connections to, if they have the actual problem."

Marty 39:26 Once we had the initial insight from, uh, these first, uh, prospects, um, it's just like, how do you find more of them? So just, like, how do you, uh, duplicate this person?

Advith 39:34 Yeah, so what... How does that look like? So you start off with, like, high-touch, you already you know, and then you sort of expand out to sort of, like, your broader network.

Marty 39:40 Right.

Advith 39:40 What... How do you make the leap from that to, "Hey, like, we're gonna have customers who we have no connection to?"

Marty 39:44 We had already started to see this problem a little bit in our LinkedIn outreach and the calls we were having, so we already had, like, a repertoire of people that we could go back to, uh, and be like, "Oh, they mentioned Slack during this," and we recorded a lot of the calls, right? And so we could discover, hey, these people mentioned Slack, or it's likely that they also operate this way, so we could go back to them quickly and, and validate. But at the same time, it's like we were already doing the outreach, and so we could just continue to do the outreach. Um, I don't think we explicitly changed the format of our, like, outreach message, so it still remained like, "Hey, we're exploring ideas." But eventually it, it became, "Okay, we actually know we're trying to just solve this problem for people, so let, let's switch the message from, 'Hey, we're exploring ideas,' to, 'Hey, do you offer Slack support? Maybe we're [chuckles] we're, we're building something around that, um, that, that could help.'" And so I think, like, of our first 10 customers, probably, maybe, like, half of them were more in-network, and then half were, were out-of-network, and mostly through, like, LinkedIn outreach. Maybe a couple were through, uh, like YC, like... Well, I think one was from the batch, one was from, like, a happy hour with alumni. Um, yeah.

Marty 40:46 And then also, Robert, do you want to talk about how we got into YC? Because, um, you basically had a connection.

Advith 40:50 Yeah. [chuckles]

Marty 40:51 It was kind of not the traditional path, actually.

Advith 40:53 It was a weird, yeah.

Marty 40:53 I don't know if you remember this.

Advith 40:54 I remember this.

Marty 40:54 Yeah.

Advith 40:54 What was the...

Marty 40:55 Um, one of my friends was friends with one of the admissions people- [laughing]

Harj Taggar 40:59 [laughing]

Marty 41:00 ... and said, "You guys are trying out this new thing for people who are pre-idea," and so they were like, "Do you want to talk to a partner?"

Harj Taggar 41:06 Like office hours, like open office hours.

Marty 41:07 Yeah.

Advith 41:07 Oh, okay. Yeah, we did a bunch of that.

Marty 41:09 Yeah.

Harj Taggar 41:09 So we get on the call, and it's not a partner. It's just him, and, like, the day before, we had found this idea, and we were like: "Hey, like, here are all the ideas that we've ever tried. What do you think of all of them?" Um, he ended up saying that the logistics idea was great, this idea was, like, okay, and all the other ideas that we had were really bad. Um, it actually lined up with what our gut kind of, uh, said, uh, about everything. But I think for us, we really wanted to go through YC with a, a validated idea and try to take it from zero to one versus, like, pivoting, because we already had built that skill of pivoting. And so that's where we were like, "Hey, like, can we spend, like, a week or two trying to close that first customer and build out the initial product, and then we'll come back and do the interview?" And so that's basically what happened.

Marty 41:51 Yeah, so, so we came out of the call, and he's like, "Okay, do you want to, you know-... like, your ideas aren't that good, but we like you guys. Um, so do you wanna do an interview with YC, um, either tomorrow or two weeks from now? And so we said, "Okay, let's do two weeks from now," so that we could, you know, do that-

Harj Taggar 42:07 Use as a deadline.

Marty 42:08 Yeah. And so... And this was also Thanksgiving was in the middle of that, and so we were basically hustling to close, uh, Hightouch or, like, anyone else we could find. Um, and at the time, it's like we had, like, a Gmail address- like, we were, like, sending out calendar invites to, uh, Theresa, the, at the time, head of support engineering at Hightouch, and it's like: Hey, like, you know us, with our Gmail account, scheduling calls with her, um, try- no, no name of the company, no nothing, and she's actively looking for tools to solve a real business problem they have. So, you know, we show up on the call. We're both like, "Hey, like, you know, we can build this, but also, what do you need?" So [chuckles] you know, trying to, trying to play that game. And, um, yeah, she, she actually was evaluating other tools. Um, we beat out those other tools, which was awesome. Um, and so by the time we show up to the YC interview two weeks later, um, you know, we had... They were, like, just about to deploy it, um, our, our instance of Pylon. We unfortunately couldn't get them to do it over Thanksgiving, but they were, like, right there. I think they were ready to go. So we had a lot that we could say during the interview process. Um, we hop on. I think it was, like, 10:00 AM on, like, a Tuesday or Monday. Um, you, of course, are there, uh, with a few other YC partners, and for anyone who doesn't know what this is like, you basically... I don't know, is it still Zoom or no? It's Zoom, right?

Harj Taggar 43:17 Uh, it's a mix.

Marty 43:17 Okay.

Harj Taggar 43:18 Most of the... We do more in-person ones now.

Marty 43:19 So yeah, for us, it was, like, at, at the tail end of the pandemic. I think we were the, we were the first batch where things were gonna move to back in person, and so we hop on this 10-minute call in the morning. Um, they kind of like... You know, Harj is peppering us with questions of like, you know, "Why do you deserve to exist?" [laughing] Like, "What are you..."

Harj Taggar 43:36 [laughing] No, you didn't ask.

Marty 43:37 It's not part of the questions, but, but you know, it's... They're, they're basically digging into the business, and, like, one thing, um, that we actually had prepped a lot was there's this, like, online, um, Paul Graham simulator thing-

Harj Taggar 43:48 [chuckles] Nice

Marty 43:49 ... um, where it's just, like, a bunch of common questions that you guys ask, and then it changes every 10 seconds. So the idea is, like, you have to answer in 10 question- 10 seconds and, like, rip through them, and so yeah, like, uh, we go through that. It goes by really, really fast. Um, and then later that evening, um, you give us a call, and you're like: "Hey, you know, we like you guys. Do you wanna do YC?" And I think at the time, we were- we still, like, didn't know for sure. At the time also, I think YC was going through, like, kind of a, a ch- shift as well, right? It was like pandemic, kinda changed everything around the world. And, um, and so yeah, we... Our thought process for doing YC, which I think is, is helpful for, for other people, is like, hey, YC fee- felt like much more than just investment dollars, essentially. And so, and, um, the... I think one thing, uh, that, that felt true was, like, every person we spoke to who was an alumni of YC was like, "You should do YC," like, "and YC's great." Everyone who hadn't done YC was like, "Oh, they take so much equity, like blah, blah, blah." And so, like, it's kinda telling that anyone who's actually done it is, like, saying you should do it, and then anyone who's not kind of probably, like, feels, like, insecure that they didn't do it, and then also, yeah, is just complaining about stuff that doesn't actually matter as much.

Advith 44:55 It's like a startup rite of passage, it, it, it almost feels like, so it's always cool to be part of that. And then I at least left the interview feeling like there's no way that, like, in 10 minutes, anyone can understand what we're doing. It just felt like a, almost, like, fake, [chuckles] like... Yeah, it's like there's no way in 10- But now I feel like interviewing so many people, I feel like I could tell in, like, 10 minutes. [chuckles]

Harj Taggar 45:10 Yeah, your idea, you can actually tell pretty quickly.

Marty 45:13 Yeah, yeah. And, and that's the other thing. I mean, this is same with, like, choosing co-founders is, like, the idea matters a lot less, and it's more of, like, how do they think?

Advith 45:20 Mm.

Marty 45:20 And, um, one piece of advice I've given to people interviewing with YC is just, like, hey, if... Like, just try to know your space really well so that they can't find gaps that you haven't thought about in the 10 minutes, right? Like, if in 10 minutes they can discover, like, like, obvious flaws with the idea that you've never thought about, and this is supposed to be your main thing-

Advith 45:39 Mm

Marty 45:39 ... then that's probably a problem, right? And then, like, how are they supposed to trust you to build a big company over time? So yeah, I think, yeah, I, I agree with that as well. But those 10 minutes, and then I remember, so we're in the apartment at the time when we get the call. Um, and I think, like, yeah, you're on speaker probably, and we're just like, "Should we do it? Should we do it?" And I, I think we said yes, like, on the phone, right?

Harj Taggar 45:58 I think we did it on the spot.

Marty 45:59 Yeah.

Harj Taggar 45:59 I think we might have muted you, and we're like, "Uh..." [laughing]

Advith 46:01 Yeah. [laughing] Nice.

Marty 46:02 And, and I feel like this also falls in line with, like, okay, why do people start companies? For us, like, fun and adventure, and clearly YC was the fun option. If you just think about your life, and you're like, "Oh, like, I should have done that or, like, been part of that thing," um, I feel like we would have regretted not doing YC, for sure. Um, and so at least once in our life, we wanted to go through it, and so yeah, we, we said yes. And then I will say, at that point as well, for context, like, we weren't paying ourselves. Um, so, you know, we were super, super scrappy, like, lots of McDonald's. Like, that was, that was also... We felt, I think, in some ways, proud about how scrappy we were, right, and, like, how frugal we were. Um, now YC is saying, "Okay, here's 500K. Like, go open up a bank account," and so we, like, go rush to do that. Um, and yeah, like, we didn't touch that money for a long time. Like, y- we didn't even start paying ourselves 'cause we were, like, afraid to touch it. It's like, "Oh, we're never gonna, like... This is, like, all we have. Like, we can't waste it, um, on paying ourselves or, like, you know, food or what [chuckles] whatever it was." [chuckles] And so we, like, get the money. We open up the bank account, and then also, I think we were, like, in hardcore mode. Um, and still, I think we're probably a lot more hardcore than other people, where w- so YC's gonna start. You guys have this, like, retreat in Sonoma- [chuckles]

Harj Taggar 47:13 [chuckles]

Advith 47:14 We used to.

Marty 47:14 ... as, like, opening it. Yeah, used to.

Harj Taggar 47:15 [chuckles]

Marty 47:15 Okay, used to, and this was, I think, for kind of-

Harj Taggar 47:16 We got more hardcore, too. [chuckles]

Marty 47:18 Yeah.

Advith 47:18 Yeah. [chuckles]

Marty 47:18 So there we go. There we go.

Advith 47:18 [chuckles]

Marty 47:18 To be honest, it was actually really good. I think, like, all the-

Advith 47:22 That was a great retreat.

Marty 47:22 Yeah, yeah, it was a... [laughing] Like, you know, at the time-

Harj Taggar 47:25 Meeting the other founders is super valuable.

Marty 47:27 Yeah, and, and that's the thing w- we, we realized is, like, the community is what made it so valuable for us. It's like, I, I think it's like equating, like, going to school. It's like, at least f- uh, for, for most of us, it's like I don't think our classes were what built most of, like, the value of, like, going to, to college, for example. It was more of the people you met, the clubs you were a part of, like, the extracurriculars you did, of, like, hackathons, for example. And so w- I felt like YC was kind of the same like that, where, hey, you're just, like, learning a lot from everyone around you. They're all saying, "Hey, here's how we thought about this idea, this market. Like, here's what our product's doing," and suddenly there's this, like... You, you can just, like, learn from so many directions at the same time. Like, a lot of people might be like, "Oh, what is that advice that YC partners have that is so valuable that it's, like, worth, you know, um, worth the deal?" And it's, like, not just that. It's like-... everyone else. And so, yeah, you're just s- speed learning so much faster than everyone else, uh, because you have literally, I think, what, 300 probably other people in our batch, um, hundreds of other companies, and so who all might be like working on things that are adjacent, uh, and that we can learn a lot from. So yeah, the retreat was actually great. [laughing] Um, we, we were wrong, um, and it was, I- yeah, we wouldn't trade that experience, yeah.

Harj Taggar 48:37 Let's talk a little bit about how the product's evolved, um, over time. You start off with like a, a Slack ticketing integration. Um, maybe actually, what is the product today? You know, what does, what does Pylon do in its entirety? And then maybe we can work backwards to how you arrived there-

Marty 48:50 Mm.

Harj Taggar 48:50 ... and what were the signs of product market fit along the way.

Marty 48:53 For the first year of the company, we were building this, like, uh, solution to solve the Slack channel support problem, where I have a ticketing system like Zendesk, I have customers who are in shared Slack channels, and I need the tickets to go into my ticketing system. So that's what we focused on for probably, uh, the, uh, most of actually our first year of the company. We got to probably around 400K, uh, in ARR with that. Um, and then we were thinking about where does the company evolve, where does it go? And one thing that was interesting was a lot of our customers were asking us for a lot more functionality that was not our responsibility. So we were very focused on just, like, this omni-channel piece, um, but they were asking for, like, adjacent features that were much more part of the core ticketing system. And so, um, we were kind of like observing that. We were observing startups starting to tell us, "Hey, I don't have Zendesk yet. I just want to use Pylon. Like, can I just use Pylon?" And we're like: No, no, you have to wait. You have to go buy this other thing in order to use us. And they're like, "No, if you just had, like, one more feature, like, you know, it's fine. I don't even need Zendesk." And so we started getting that feedback. Um, and then finally as well, Zendesk had been acquired by private equity just, uh, like, actually the day after we started the company, and over that course of the year, uh, people were starting to feel the effects of, um, that product not evolving. Um, AI's coming out. Like, the- like, it's not the modern product anymore. Like, in 2023, at the time, like, that is- that can't be the most modern tool, uh, to do customer support with. So all of those things started coming together of, hey, um, people don't actually like the incumbent that much. Um, people are asking us for more functionality, which we are realising is, um, all B2B specific, and actually maybe there's something around building, like, a support platform for B2B companies specifically. And then also, yeah, just AI is, is, is coming into the world. So all that came together. We decided, okay, um, we definitely aren't gonna build a really big company off of just this integration, and we need to expand. At the same time, our customers are pulling us in this direction of, "Hey, build, like, something that's way more B2B specific and actually the full platform," and there's an opening in the market to do that, so.

Harj Taggar 50:47 Maybe on AI specifically, something I'd be curious to hear about, like, you guys, you guys sort of launched and started work on the product just before the ChatGPT really took, took off and, and really had its moment. Um, and you've adapted really, really well to becoming AI-native and really baking that into the product. Um, how have you done that? And then what's your advice for founders who are maybe in a similar spot to you? This, this might be like Series B or C companies who sort of built a solid SaaS product pre-AI and are now trying to figure out how they fit in in this sort of post-AI world.

Marty 51:17 Yeah.

Advith 51:17 I think really early on, we were actually very sceptical of AI, and we were very resistant to adding any AI into the product. But I think, like, we just did the same product iteration around, like, listening to the customers, what their pain points are, and thinking about all the, all the possible solutions, and AI happens to be the best way to solve a lot of those problems.

Harj Taggar 51:35 How do you separate out... One thing I've definitely seen people get pulled in is, like, customers are saying they want AI because, like, they're reading about it, and they're like, "We want AI stuff." Like, how do you separate out sort of that from, like, actual signal on something that will solve their problems?

Advith 51:47 People still do that today all the time for us, where, like, they want some, like, silver bullet solution of, like, just the canonical thing in customer support is just, like: "Answer all of my questions for me," or, "I'm, like, a two-person startup. I just, like, want something that just, like, answers [chuckles] all my customer questions for me." I feel like it's still not, like, a specific answer, but understanding, you know, where the technology is, where you are in the market. We serve B2B companies, so for example, in consumer, the types of questions, like, Uber Eats gets about refunding orders are way easier to answer. Like, a lot of the volume is in the same set of questions, and the margin for error is, like, much larger, where it's okay if you mess up five in every 100 questions. For, like, B2B, the segment of the market we were in, like, if a million-dollar customer asks you a question, you can never answer them wrong, and you never want it to feel impersonal. And so I, I feel like it's more about sequencing than, like, not doing something and waiting for either the technology or, like, market sentiment or, like, your own product vision to be in the right spot. And so at least today, maybe the high-level guiding philosophy could be there's certain workflows that make sense for AI to do entirely and should be agentic. Most workflows, I feel like, at least in our space, are, oh, it's a combination of people and AI that should be working together, and then kind of there's some things that just people should be doing, like building relationships, and then how do you, like, cater the product to that, like, world view? Yeah.

Marty 52:57 Yeah, so I think it's, it's good that we were slower to... Well, we were basically more sceptical of whether AI is, like, the silver bullet for everything and much more approaching the problem of, like, yeah, there are many problems. Out of all the solutions we could build, like, which is the best, and AI just happens to be the right solution for a lot of them. Um, another thing to mention is our core data set with Pylon, if you think about customer support tickets, um, to start, is all conversational data. So, like, when you think about what, like, LLMs enable, it's like, okay, taking con- like, text and structuring it so that you can build workflows off of it or do thinking on it. Um, suddenly, that's, like, incredibly applicable to our core data that we, we house, and so that means all this unstructured data that used to be really hard to turn into structured workflows is now structural. And so that has been a huge unlock for us, where, um, like, it- there are just so many things that you ideally would have wanted to do off of, like, applying AI to, like, a conversation or, like, lots of data about a customer that are now possible. And so we definitely get to think from first principles on, like, okay, what are, what's, like, the, the grand vision or effectively, like, if you had a really smart, like, B2B ticketing system and CRM, like, what would you want to build? Um, and AI, like, turns out, can enable so many workflows within it-

Advith 54:11 And-

Marty 54:11 ... with this data, yeah.

Advith 54:12 For all the existing f- like, companies, I feel like they can do the same thing of just trying to introspect on, like, what is the core- what is, like, the core data source you have? Is it very, like, amenable to using AI? Like, what are the core workflows in your product? Which ones, like, have this low margin f- or, like, kinda can, can-... be fine with AI messing up sometimes, but still provide a lot of value, and like kind of bet on the technology improving and like sequence your product roadmap to like benefit from how that's gonna play out.

Harj Taggar 54:37 Um, how about we sort of look towards the future, um, here? Tell us a bit about kinda what should we expect to see from, um, maybe Pylon, like the product, what's coming that, um, that you're really excited about? And then maybe just as a company, like how do you think about growing the company and the kinds of people you wanna attract?

Marty 54:53 Yeah, I, I guess I can start on the, the product side and, and where we wanna go. Um, so we started with the core ticketing system, and, you know, this, this omni-channel wedge of, hey, Slack support team, support whatever. First off, that trend turns out is way bigger than we thought. Like, that is still one of the core reasons people come to us, so, um, that, that has continued to re- remain important now. But long term, uh, what's gonna be relevant is more and more customer-facing teams are going to build workflows, um, out of... in Pylon. They're going to live off of data in Pylon, and all these customer teams should be able to like work together off of conversational data. So, um, we, we started with ticketing. We're adjusting that well, building good workflows there. We're expanding into customer success and account management teams who want to handle customer data post-sale. Um, and then even adjacent teams as well. So for example, "Hey, um, I want to know all my feature requests." Um, and like the support team might wanna pass that data to the product team. So we can structure all of that data and give that to the product team now. Um, "Hey, the marketing team wants to know... um, we wanna do a blast to our customers who have asked for this feature in the past. Like, um, help me gather a list of those customers so that we can go send that data out." So, um, it's going to turn from like just core ticketing system into more almost like CRM. And so realistically, like very long term, this is gonna look less like a, like a AI Zendesk and more like a AI Salesforce. Yeah.

Harj Taggar 56:12 How about the company?

Advith 56:14 We're going multi-region, so we're opening up a New York office. Probably we'll have a office somewhere in Europe as well later this year. Um, now we have like a V1 leadership team. We'll probably have like, um, several layers of folks within the company, and we were very [chuckles] resistant to a lot of these like normal company building things, like very, very resistant to like having managers or tracking work or like doing anything that most companies do.

Harj Taggar 56:35 [chuckles]

Advith 56:36 But we're basically refiguring out from first principles or like running into these problems ourselves, why people do any of these things, and so-

Robert 56:41 And I think it, it was important that we didn't implement it all at once at the beginning, and we figured out why these things work. 'Cause I think a lot of people just like implement what they see at giant companies without really thinking like, does this actually push the company forward?

Marty 56:54 Yeah, so, uh, it, the- [clears throat] yeah, so basically, I guess for the com- the, the business, um, we're still focused on getting to a billion dollars in revenue. That is still like the end goal and the, the win conditions for this game that we're playing. So yeah, um, if you like joined one of our, our meetings between the three of us, it's always like, "Okay, are we on track to do that? Um, what market should we be exploring? Um, you know, where are we gonna run out of, uh, space with the current like wedge product that we have?" And, and so yeah, um, still focused on a billion dollars in revenue. Product, uh, is really well-positioned to expand a lot, given our data set and w- where we live about around the customer and, and the, the roles. Um, so yeah, there's, uh, a lot of room to grow.

Advith 57:32 And maybe a main change is like basically being way, way more intentional about like literally everything that you might have assumed was happening just naturally before. So like being intentional about what we make product bets on, like where we hire people, what regions we expand to. Basically, all decisions, trying to become like way more intentional about them.

Harj Taggar 57:47 Um, how about we finish up here? I'm just curious, does each of you have sort of like a, a reflection on, um, how... Like what's sort of one area, one specific thing that you've really grown in as founders, um, since you started the company?

Advith 58:01 You kind of hear this before, that like people are what make the company, but actually, like in our roles, like the biggest leverage is people. Like, just like h- you're essentially trying to use people to like do like bigger and bigger and bigger tasks, and just like, how do you do that, I guess? And just knowing that that's like the most important thing, I feel like I never internalized it until like we reached a certain scale where everything, like instead of turning to you doing it, then you have to turn to somebody el- You like operate in a different mode, where you're like actually trying to figure out how to get a broader set of people to do it, or who's the right... Aligning work to the right set of people actually cr- creates like a really big outcome if you do it in the right way. And so all these like people things I actually feel are what make the company, yeah.

Robert 58:39 Yeah, my answer is kind of similar to that [chuckles] actually, yeah. 'Cause I thought a lot of it would be like a lot of critical thinking on our end, of like, oh, we get together as a leadership team, and we like work on a problem. But like most of it is just as, as the tree gets bigger and bigger, you're further and further away from the IC.

Harj Taggar 58:53 Yeah, you go from being like the person doing all the work to getting other people to do the work-

Robert 58:57 Right

Harj Taggar 58:57 ... do it well and consistently.

Robert 58:58 And it's still important to be able to dive all the way down and see what's happening at, on the IC level, but like, I think a lot of the work is actually just talking to people all the time, yeah.

Marty 59:09 I think we are very in the weeds still with a lot of the projects, and I think that's good. Um, I think the, the longer we can stay, like, very involved, um, in, in like being evaluators and editors on work, I think, uh, will be very helpful for the company. And it is crazy to think, like when we think about company planning and, like, direction, I mean, it's all up to us. [chuckles] Like, there's like no one else that like-

Advith 59:31 Yeah, I guess-

Marty 59:31 ... has the context

Advith 59:31 That's another realization.

Marty 59:32 No one else is, like, paying attention in the same way. Like, you might think, like, oh, investors over time are gonna, like, be able to, like, guide you of whatever. No, it's, it's just you. Like, you [chuckles] like, like the three of us right here are going to determine the futures of all 79 people, and like-

Advith 59:45 Yeah

Marty 59:45 ... everyone who joins. And like, if we take our eye off the ball or stop working as hard, like, yeah, it's, it's... We cannot. Um, and so I think, like, yeah, there's, there's the founder mode piece to make sure that we're involved, so we can make sure the right, like, uh, decisions are being made internally, and then also kind of the, the higher level, like, we have to steer the ship because no one else is gonna do it. And yeah, yeah, that determines the, the long-term fate of the company.

Harj Taggar 1:00:07 Nice. That's the exciting part of being a founder.

Marty 1:00:08 Yeah.

Advith 1:00:08 Yeah.

Harj Taggar 1:00:08 Cool. All right, I think that's all we have time for. So thank you so much for joining us, guys. It was really interesting to hear the story.

Advith 1:00:13 Thanks, Harj.

Robert 1:00:13 Cool. [upbeat music]