A Product Market Fit Show | Startup Podcast for Founders
00:36:00 · Pablo Srugo, Chris Slowe
[00:36:00] S1: Did you and Steve have an aura at that point coming out of Reddit? Was it easier to hire, easy to fundraise the way that it would be now if you had a Reddit exit? [00:36:11] S0: I think it definitely helped. I mean, what actually did help there too was Hipmunk was also an YC company. Getting back into YC was also easier having already done it once. Part of doing startups is doing startups or doing startups well is you have to be able to get your knocks at some point. Already having had a startup behind your belt and an acquisition behind your belt helps a lot. I think also the other things that came up were like, yeah, we had to exist as architects, set a pretty decent sized product with a decent user base. Therefore, we were pretty good engineers at that point and we knew web development really well. If anything, the learning curve for Hipmunk was that was the time when app stores really starting to take off and so we had to start learning how different the requirements are of dealing with the Play Store and with the App Store on iOS. That was a new muscle, but it wasn't a difficult thing to hire for. It was difficult to do well at that point in history. [00:37:04] S1: At that point, I mean like you said, Reddit, you had to do no marketing, it was all word of mouth this time. Did you get into paid ads or what do you remember? What was your big acquisition channel?
00:37:13 · Chris Slowe, Pablo Srugo
[00:37:13] S0: Some of the early hires we had to do at Hipmunk that never even came to mind at Reddit, we had to hire a BD lead extremely early. That was because that was entirely to make deals with airlines and hotels and larger companies just required attention and it required somebody who had some experience doing BD as a profession. Marketing was also extremely early. I remember actually even at the time back in 2010, 2011, we hired our first social media manager, which having just been at Reddit for so long, the idea of a person whose job it is to manage social media, what the hell was this? How is that a job? Also another thing that came up around that year 2010, 2011 was also the first time I heard the word data scientist. I'm like, data scientist? You mean that has a name now? You just dig through the logs and you get the answer. I didn't know that was a full-time job. The earliest part of the team, the first 12 employees give or take, included at least two people working on BD and at least one person doing marketing and the rest of it was mostly software engineers but there was a customer service element as well where we actually had to have – we were dealing with money and the side effect dealing with money is you have to pay to have a CS team around to answer questions because the last thing you want to do is have some person stuck in limbo with their money. [00:38:30] S1: With Hipmunk, did you guys get to product market fit, would you say?
00:38:30 · Pablo Srugo, Chris Slowe
[00:38:30] S1: With Hipmunk, did you guys get to product market fit, would you say? [00:38:33] S0: What we learned most with Hipmunk was we definitely solved a set of user problems really well and we had some really rampant support, users who really loved using the product. I think what we learned though was economies of scale are a bitch. Having a small product like Hipmunk meant that we couldn't take advantage of just the bulk discounts you start getting when you have volume. Originally we went into it with a bunch of disdain for the large players, because it's like look at how crappy their product is. Yeah, their product is crappy but they're booking a billion dollars in revenue. You can afford a lot of crappiness if you can actually get that much lead gen, because you can spend a ton of money on marketing to get more users. I mean, you can buy a Super Bowl ad and be completely reasonable. [00:39:15] S1: Talking about flights, this is different, but always most flights customer service, when you're in it's just terrible. Sometimes I talk to people about this and I'm like the problem is when it comes down to it, I'm cheap as shit and I'm going to take the cheapest flight that gets me fastest and I don't care if they – they might have yelled at me when I was on the plane but if it's the cheapest flight that gets me fastest, I'm going again.
00:39:15 · Pablo Srugo, Chris Slowe
[00:39:15] S1: Talking about flights, this is different, but always most flights customer service, when you're in it's just terrible. Sometimes I talk to people about this and I'm like the problem is when it comes down to it, I'm cheap as shit and I'm going to take the cheapest flight that gets me fastest and I don't care if they – they might have yelled at me when I was on the plane but if it's the cheapest flight that gets me fastest, I'm going again. [00:39:40] S0: That's the thing too is the flight is the means to the end. You're on the flight because you have to be and you don't have a lot of choice. It's like a temporary purgatory before you're doing the thing you actually want to do. No one takes a flight because they're like, "Oh yeah, I want to spend six hours in this metal tube with a bunch of humanity." It's like, no, you do it because you're going to go to fricking Maui and you have to get in the plane to get to Maui, which is also why we found that it's straight -- that's actually why we chose agony as our sort because everyone hates – there's very few people who are like, oh, I love flying. Even people who have -- at this point in my life, I have 1K status, which as we all know isn't a good thing. It just means I fly enough that I actually got status. It's like the mark of the beast. It's like, oh, I'm sorry, you have 1K. I remember I was in a plane at one point recently and the guy behind me hit his 3 million mile mark, and everyone around him was like, congrats, whoa. It's like, are you okay? [00:40:42] S1: It's like, are you okay, dude?
00:40:42 · Pablo Srugo, Chris Slowe
[00:40:42] S1: It's like, are you okay, dude? [00:40:44] S0: He wasn't old. He was younger than I was. I was like, "Oh man, you've spent a lot of time in planes." [00:40:49] S1: That's rough . Yeah, that's rough. [00:40:50] S0: It's like that George Clooney movie from 20 years ago. He was up in the air and it was like he realized he spent his entire life on planes. Yeah. [00:40:58] S1: No, good. Walk me through, did you guys end up selling that? I'm interested obviously in the transition back in Reddit. Did you end up selling Hipmunk or how do you come back to Reddit? How does that happen?
00:41:08 · Chris Slowe
[00:41:08] S0: I think by about 2015, Hipmunk was in a good steady state. From my standpoint, a lot of the technical problems were solved or were just a matter of playing an existing playbook. There wasn't a lot of difficult work to be done there. What happened for me was I ended up consulting for Reddit mid '15, because at that point they were starting, starting to scale up a little bit more. The company was up to around 70 employees. They were looking at actually building a mobile app. They were looking at doing something that – some of the stuff that I had originally specialized in Retrospect was I became an infrastructure generalist. I became probably one of the first SREs in the team just as nature of the beast. I also ended up being one of the first people to work on what amounts to being – we eventually called anti ego, which is our user safety stuff. I was secondary to another guy, Mike Aldi, who is a good friend of mine now, who was the first – I don't know. At the time he was more the troll poker. He would help to fend off the trolls and put them back under their bridges and got really good at building out the toolkit for making sure the users actually had some amount of safety. Coming back the things that were top of the list for me were working on that safety toolkit, and so I ended up doing some consulting along those lines; talking about mobile usage; talking actually about data science, which wasn't really a function that existed much at Reddit that point, which again, my title at Hipmunk was actually chief scientist, which most of my titles historically was a joke but at the same time actually it was accurate. I was a scientist but also data science had come on the scene around that time, and so it made sense to say, well, Chris can work in analytics. Then by the end of that year, it was – I've made this analogy a bunch of times, but I have to repeat it. It's like it had the same feeling as dating your ex-girlfriend where it's like you dated a long time ago and you broke up for very good reason, but that was like five years ago.