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Ep 4: How Product Hunt’s Ryan Hoover Built A $20M Community From Scratch

 
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Shaan Puri: And so you sell the company, you got money now. What happens that first day money hits the bank? Were you sitting there refreshing Wells Fargo?

Ryan Hoover: Some people, they love to go celebrate with a big thing. Actually me, I flew to LA that day. I think it was a Friday and we actually just went to a restaurant and I ordered of course a rotisserie chicken, and some Brussels sprouts.

Shaan Puri: All right, so let me start with this. I wanted to have you on because A, you’re my friend, we haven’t caught up in a little while because you’ve been traveling and doing all kinds of interesting stuff. B, you’re probably unique. Most of the people I have on this show-

Ryan Hoover: I’m special.

Shaan Puri: Yeah, you’re special. You’re a special snowflake.

Ryan Hoover: Yes.

Shaan Puri: Most of the people I’m trying to have on this show are the greedy capitalist pigs. I like that, I’m like, oh you found out that you can buy and sell this one arbitrage, and you levered up and you did this crazy thing, but you’re very different. You’ve done well in business but I think that’s a by-product. To me, you’re a really thoughtful dude who has built a really cool business yourself, plus invested in a bunch of other interesting companies and you’re different. You’re the nicest guy I know in tech who’s around town and I want people to get to know that side. Most people know the journey. Here’s my short version of the story. So, Product Hunt started as a project, not even a company. Is that fair?

Ryan Hoover: Actually, I call it an experiment. So, not even a project. It was pre-project.

Shaan Puri: We’re talking weekend experiment? Or what were you thinking at the time?

Ryan Hoover: I was tinkering. It was an experiment, that’s what I called it actually, if you look back on the Tweet, the word I used was an experiment. There wasn’t really an intention or a goal other than just exploring. Do people find new products really interesting? Do they subscribe to this email list I created? That kind of thing.

Shaan Puri: Right, and you reached out to me and the way I felt was, I geek out about every new product and want to talk about it and see new things all the time. Are there other people like that? I think I know 100 of them and let’s start with that 100. How many people were on that initial outreach mailing list for Product Hunt when you started it?

Ryan Hoover: It was an email list in the beginning. Anyone could subscribe in the very beginning and a couple hundred people subscribed in the first couple days but from the beginning, it wasn’t me curating the products. From the very beginning it was like, okay, I know a lot of people, founders, investors, people who are in technology who are always exploring new things like yourself. And I think it was 20 or 30 people were sort of the curators. The people that were just sharing new products they found.

Shaan Puri: Right. That’s the set up. It’s basically, “I’m Ryan Hoover.” At the time, you had just left a job at Play Haven. Is that right?

Ryan Hoover: Part-time. I half left.

Shaan Puri: You half left. Okay.

Ryan Hoover: I was part-time actually.

Shaan Puri: Okay, so side project, side experiment almost, 20, 30 people on the list. You call the thing Product Hunt and what I liked was that it was A, a community of people and B, these were not apps that we had all already heard of because I would have pretty much immediately discounted it if it was Facebook.

Ryan Hoover: Yeah.

Shaan Puri: Obviously that would have been ridiculous. But even just the stuff we all read about in Tech Crunch that day, no point in posting it again on this little site. This was genuinely sometimes just little useful things that I never heard of that people were using to lists and whatever. And then sometimes it was really cool funky projects. There’s a community of people posting products, apps, that you have never heard of. So it became this must check place for what’s new in a city where everything’s new.

Shaan Puri: So, that was cool and the summary is, it becomes the water cooler, the whole tech scene is on here. If everybody in Silicon Valley either uses Product Hunt or just likes Product Hunt but is too busy to use it, but generally is on board with it.

Ryan Hoover: One thing I’ll note though, even though it started with a lot of people in Silicon Valley, those 20, 30 people were people I had met, friends of mine. Quickly it was global, the very beginning. And quickly we started seeing not only visitors but contributors around the world. Even today, almost six years later a perception like, “Oh, it’s a bunch of Silicon Valley folks?” I checked the metrics the other day and it was less than 1.4% of visitors in the past 30 days were from the Bay Area.

Shaan Puri: Wow.

Ryan Hoover: That’s expected when you get to a certain scale but it’s a tiny micro subset.

Shaan Puri: What about the people who post? Was that the same thing? For a lot of people, they didn’t even mind. I knew people who were in Florida or in India who were checking it and one of the reasons they liked it was, “Hey, I don’t know anyone in Silicon Valley. This is where they’re posting and talking about stuff? Cool I get to be a part of it.” Even if they didn’t even have the ability to post themselves at the time. What about the curators? Were they mostly Silicon Valley people or not?

Ryan Hoover: In the beginning, yeah. Frankly, it wasn’t super thought through, there was like a lot of experiments, you just want to quickly test something and throw it out there. And in the beginning it was friends who happened to be geographically located around me, so a lot of people in Silicon Valley. And the thing is, those people of course would post products and things from just around the internet. So it wasn’t like they were only looking for founders in the Bay Area to post their product. It was really apps and Chrome extensions and physical products and things like that. But over time, its extended and we’ve intentionally try to extend it to all corners of the Earth in terms of getting perspectives from Berlin tech scene and Bangalore and Toronto and everywhere else.

Shaan Puri: Love it. And so just if I finished the kind of summary, it’s basically you get the momentum, you become a company at some point, you go into YC, you raise money from Andreessen Horowitz, you eventually sell the company. I think publicly it’s come out that you just sold a company, $20 million to AngelList. You were an AngelList app right now-

Ryan Hoover: I am.

Shaan Puri: And now you’re there and now you’re both running product on AngelList as well as you have something called the Weekend Fund. So we’ll go into all of that. But I want to start with in a way I was there at the start. This is kind of our personal relationship was in many ways I’m the godfather of products. Would you agree with that?

Ryan Hoover: Kind of. I don’t know if godfather is the right title, but almost like, you could have been the one that killed Product Hunt.

Shaan Puri: Yeah, I’m like the evil stepdad or something. There’s something weird. So the back story is, I had seen you blogging because for many, many years you were talking about products and you were blogging. And this is kind of like, I’ll call it before the blue check Mark Ryan Hoover. There’s like, before the check Mark and after the check Mark. This was before the check Mark and I was like, “This guy’s really interesting. I wanted to hire you.” So I reached out and I was like, “Hey, let’s get lunch, let’s talk.” We started talking. Turns out you were thinking about moving on from where you were currently at, and we both got really excited and we went through a process of like seeing, are you a good fit for where I was, which was Monkey Inferno, this idea lab at the time and I thought, “Hey, it is a great product.” After the idea lab, long story short, we go through the interview process, doesn’t quite work out.

Shaan Puri: I let you know, “Hey man, talked to the team. It’s not going to work out, but I’d love to stay in touch because I’m not just like lip service, genuinely really like you think you’re really good, so let’s, let’s keep in touch.” I don’t know, 10 days later or a week later you started the experiment. Is that… that’s my memory. Am I right?

Ryan Hoover: I don’t remember exactly how many days, but yeah, fairly shortly after that and, I remember the email, I mean it’s still in my Gmail somewhere, that you sent to me that was really thoughtful in telling me why you didn’t feel I was a good fit for the role. And actually when I reflect on that, I think you were right. Even in hindsight, I think you were right in your assessment of… especially at that time, I’ve always been a very passive person, someone who’s not… I don’t like confrontation and I didn’t feel qualified to tell people what to do. And I know that was one of the pieces of feedback is you’re… and I forgot the exact way you phrased it, but it was something around leadership and a decisiveness. And that was a very valid point, which I think when Product Hunt started kind of fast forwarding, I’m now sort of forced to learn some of those things.

Shaan Puri: Right.

Ryan Hoover: And it’s the thing, I still work on to this day, but I’m much better than I was six years ago at some of those very valid reasons for not hiring me.

Shaan Puri: Right. And I think that in this situation, I would say 90% of the credit goes to you because most people, I know me, if I didn’t get hired somewhere or get rejected that feels bad, there’s no way around it. I would’ve been like, “F those guys.” And I know that’s the initial reaction I would have had, even when I was typing that email. I remember the phrasing I use, I said I’m going to go on a limb here, I hope this is not salt in the wound, I’m going to give you some detail on what the actual feedback was.

Shaan Puri: Normally, I literally wrote I said, normally the email ends here of like thank you for your… sorry not this time, let’s keep in touch. I was like, normally it ends here, but I’m going to actually give you the feedback because you seem like a dude who wants to learn and get better. If I was in your shoes, I’d want to know the real reason. Here’s the real reason. Hope that’s not salt on the wound. Hope this was productive and helpful. And to your credit, you took that and you were like… we stayed friends right away and so tell me about that. Because I think that’s unusual and there’s going to be a lot of people listening to this who are either have faced rejection, are going to face rejection or currently putting themselves out there and maybe something’s not going to work out. You clearly had a happy ending, but even in that moment you took it.

Ryan Hoover: Yeah, you’re right. Most employers don’t do that. They don’t do it for a few reasons, usually one, either they just want to quickly move on. Two they’re afraid of hurting someone’s feelings and telling the honest truth or three, there’s sometimes legal reasons why you maybe don’t want to say certain things. I appreciated that and I actually, I do some investing in when we meet companies and the reality is we don’t say yes to every company. Surprise, surprise. And we actually have to say no to a majority of companies that we do meet with. And I’m trying to get good at this, but we try to, for every face to face or video to video kind of conversation we have with the founder, we always reply with details of why we’re not investing right now.

Ryan Hoover: And I feel that’s an important for a founder to hear because it’s really a bummer when you’re pitching and you’re going through that whole process, getting a lot of no’s and everyone’s saying like, “Sorry, no thanks.” But no details. There’s no feedback loop. There’s no way for me to learn from this experience. And although it can be kind of painful sometimes, having received rejection myself, but also, being on the other side of it, it’s helpful. I think it’s valuable to our ecosystem, I guess to get that kind of feedback.

Shaan Puri: Right. It’s valuable on both sides, because you’ve got to really think if you’re going to write down why, you got to be clear about why and being forced to kind of articulate your thinking, it’s good for the kind of giver and for the receiver, which is cool. And most investors don’t do that. Why don’t most VCs tell you why? They basically always say not right now. They don’t even say no.

Ryan Hoover: Yeah, some of it is just time. And some laziness perhaps, and they want to move on the next deal. Some of it is they, they never say no. They just say, “Let’s stay in touch and…” Part of that is because it’s such a relationship driven market. And when you say no, some founders will immediately take that as, “Okay, I’m never going to talk to that person again.” So I’m doing a seed now when I go to my Series A, I’m never going to talk to Bob because he said no.

Shaan Puri: Right.

Ryan Hoover: And I don’t think that’s the right way of doing it. I think if you deliver the no with authenticity and being truthful, they’re actually more willing to trust you and keep you in the loop. Seen this happen where founders will follow up three or four months later and say, “Hey, just want to give you an update. Here’s where we’re at.” They’re not asking for money or anything. It’s just that they want to keep me in the loop to potentially convince me otherwise of sort of prove me wrong, but not in like the egotistical way.

Ryan Hoover: It’s more that, they want to share this information with me because they still want me involved.

Shaan Puri: Right. And I remember during the job interview, we always set it up where you do a case. So it was like, “Hey, here’s a product that we are actually building and here’s the challenge we’re facing. Take a day, think through how you would approach that, and then basically we’re going to present that tomorrow. So we’ll talk through it.” And you did an amazing thing. We had this app that was a pretty bad idea, but it was a side project that two of our young guys were kind of hacking on at the time, which was, it’s a site called [Boya 00:11:35] and that basic idea was, it was like you would say stuff about your life, so you’d be like, “I’m Shawn, I once won $1000 in a poker tournament.” Or, “When I was young I was into movies.” This is real things, so I put those on my thing and then anybody can come and ask questions. So it was like a Q and A site, but you would give people a little bit of material to go off of of like, what the heck should I ask you?

Shaan Puri: Because if I don’t know anything about you and you’re not already famous, what the hell do I know to ask you? And we gave you that case and I remember you did the amazing thing and anybody who’s applying to a job, I would recommend you do this even if they don’t ask you for a case. You took the product, you not only had your own ideas of what you could do to make it better, but you went and talked to a bunch of users of our product and you talked to more users of our product and the guys who were building it in our lab, had talked to at the time. And I remember being like, “That’s a really good sign.” You were like, “Here’s Jacob. I had talked to him. Here’s what he thinks about the site today and here’s some ideas based off of my conversations with the users.”

Shaan Puri: That was pretty amazing, and I will recommend that to anybody who’s applying for a job of like, put your hands on the… don’t send your resume and hope that it just stands out, put your hands on the product, go talk to the users, show that initiative. Have you seen that in people who are applying to Product Hunt or AngelList, have you seen anything that stands out?

Ryan Hoover: Yeah, I think if you… especially with any company that has a lot of demands, people that want to hire, you’ve got to stand out somehow. If you can illustrate the value you can create, then it’s almost… in some cases it can be a no brainer to hire that person. One example of this actually is [Andreas 00:13:04]. Andreas was a CTO of product for about four ish years. He transitioned into AngelList actually after the acquisition and, he and I initially connected through Twitter and Product Hunt and he was playing around with it. He was at the time in Vienna, I’m in San Francisco and one day he launches a Chrome extension for Product Hunt. And so this was also, again, experimental phase, not even incorporated, but he launched his Chrome extension, which he created by scraping the site. We didn’t have an API or anything back then, scraping the site.

Ryan Hoover: And every time you’d opened up a new tab, you’d see the days most up-voted products every day. And that caught my eye and I was like, “Whoa, this guy clearly is interested. He has ability for us to build cool things and come up with new ideas because just him like doing design product engineering and clearly has an interest in product in general.” And so we actually connected and then he was actually working on kind of a hiring type play. He was exploring his own startup idea too. Long story short, he ends up joining, super early on and became the CTO and is a large part of Product Hunt’s I guess success to where we got today. And he did so by just building stuff.

Shaan Puri: Right. Sometimes you do the work before you get the job, if you have no other way to sort of stand out in that sense. We had a crazy guy send in. Some people try to stand out in weird ways. We had somebody send in a piñata and then it was like a layered puzzle. It was like, you break the piñata then it’s like, look under your desk and there’s a box under my desk. I’m like, “Where did this come from? How did this guy do this?” It was a bit creepy. Don’t be creepy.

Ryan Hoover: Don’t be creepy.

Shaan Puri: Don’t be creepy as a general rule. Get that tattooed on your forearm just as a reminder. And so you weren’t just looking at us, you were looking at Medium at the time. This is again pre-Product Hunt and, what were you thinking back then? What was your mindset? You’re applying to a couple of companies, what was going on?

Ryan Hoover: Yeah, I was at Play Haven up until three years. I joined as number 10 then we downsize to 6 people and then we grew to about a 100 people. So, learned a ton, built some cool things, and after about three years I started getting… a couple things happened. One, I started feeling like I was learning less and like we’re moving a little bit slower in this, partly reality of just the stage that we were at in the company.

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Ryan Hoover: And the other thing is we are building tools for game developers and as much as at the time, especially love gaming, I’m not a game designer, I’m not a game developer. I really wanted to, one, stretched myself, challenged myself and two, work on something that I’m a consumer of a user of, a user of. So you mentioned Medium actually, this sort of path was okay. I’m going to leave three years in. I was fortunate to get into kind of a part time role and transition out, but meanwhile I was exploring different startups to join and so Medium was a site, this is 2013 so pretty early days for that platform. I was on it. I was logging a bunch. I love the space. I believe if we can help more people share their ideas, I think it’s generally a good thing for the world.

Ryan Hoover: I was just looking at my home screen and Medium was of course like that, one of the things on my home screen that I was using and so I just really wanted to explore working at companies of products that I used. And I ended up interviewing with Jason Sturman who is, I think he was CEO at the time and Ev Williams interviewed with him and they were… I think they were like 10 maybe 15 people.

Shaan Puri: What’s that like? You interview with Ev Williams. This is the creator of Twitter blog or Medium. What’s that interview like?

Ryan Hoover: It wasn’t really an interview. It’s more of a conversation, which I really enjoy it. We talked a lot about the platform and just writing in general. I think we may have, memory’s a little bit fuzzy but ideated on various things. And actually before this, I should take a step back. Before this, I was trying to illustrate, really tap myself into the team actually. As I was using Medium and getting really involved, I actually hosted a Medium brunch in San Francisco and invited a bunch of Medium employees.

Shaan Puri: Nice.

Ryan Hoover: Because I’m like, “All right, if I want to work at this company, there’s two things that can happen from that, one, they’re going to at least get to know me a little bit better and two, I’ll get to know them a little bit better too.”

Shaan Puri: Right.

Ryan Hoover: I did [crosstalk 00:17:36]-

Shaan Puri: Was just employees or there was also like just other people who liked Medium?

Ryan Hoover: There was also some other people that like Medium. It was a combination and I think about 15 20 people showed up and it was a combination of bloggers and writers. There was some commonality around, okay, here are a bunch of people who writing on Medium about interesting things, mostly around tech or other subjects.

Ryan Hoover: That was I think, helpful in getting that meeting with Jason and with Ev. But ultimately, they were early on, they only hired designers and engineers, that was sort of, they had a whole ocracy kind of org structure and we sort of ended in part with, I don’t know what you do here Ryan respectfully. And again it was kind of right kind of like, Ev was right. I don’t know exactly what I would’ve done, maybe I would have been a good fit. But the way they were structured there wasn’t a clear job rec. There actually was no job rec for what I was trying to apply for.

Shaan Puri: Right. You did Product Hunt as an experiment. Did you do any other experiments at the time that nobody’s ever heard of because Product Hunt the one that takes off and gets all the attention?

Ryan Hoover: I did a couple of small tiny things as I was writing and blogging a bunch. One thing that I wanted to experiment with was, how do I get more people to share my writing? How do I essentially get more readers? One thing I noticed is there some people on Twitter who would take a snippet and quote a sentence or so from blog post and then share it on Twitter. I actually thought, okay, what if I could in my blog, which was on tumbler, but on tumbler you have access to basic, you can add Java script and other things. I hacked my way together through like… I’m not even an engineer, so I hacked my way together to create a simple little JavaScript utility to be able to allow authors and bloggers to select and highlight specific texts in their blog posts.

Shaan Puri: Right. So this is my money line.

Ryan Hoover: Yeah.

Shaan Puri: Go ahead and share.

Ryan Hoover: Go and click it and it opens up a tweet intent with the quote field and tags me or Hoover on Twitter. It was a little side project. I had no ambitions of turning into anything. Also from a code base it wasn’t real, it was just kind of for me, so no ne else really could use it but I was like, “Okay, let me tinker with this idea and see where I get.”

Shaan Puri: Right. So you were a scratch your own itch kind of guy, which is, I’ve had somebody who came on who was like… the first question I typically ask is, so how’d you make your first million? He was like, “I made a soap opera blog. I’d never seen a soap opera, but I made a soap opera website that became the most popular soap opera website and I sold it for $9 million in cash.”

Shaan Puri: And it’s like, to some people are like, “I go where the opportunity is.” And you’re like, “I build things that I’m curious about. I want, and I don’t know if they’re going to be companies or not, most likely not.” What do you think about that approach? Because I’m sure you see founders that are in both camps. How do you think about that?

Ryan Hoover: I don’t think there’s… I even wrote a blog post about this a long time ago. There’s no right way to start a startup, in the sense that, yes they are kind of best practices and guides and everything, but you can find counterexamples to basically everything including the scratch your own itch sort of advice or my father for example, my parents, they’ve been entrepreneurs, well my dad pretty much his entire life almost and, they’ve been operating in business for a long time, since I was I think 16, 17 years old, they’ve operated this business in the waste management space.

Ryan Hoover: My father really doesn’t have any particular interest in waste management. I think a lot of people who are in the industry aren’t passionate about waste necessarily, but he’s an entrepreneur that has had a lot of success just finding a problem or finding a need and filling it. As a saying that he would tell me when I was a kid is like, “Find a need and fill it.” And he gets a lot of motivation, excitement around the process of solving problems and building businesses, less so, scratching his own itch, for example.

Shaan Puri: If your parents were entrepreneurs, did you think, I’m going to be an entrepreneur? Or you went and got a job at Play Haven where you were like, “I’m going to do the career thing. I’m going to be an employee, then I’m going to become a manager and then an executive may be someday.” What were you thinking?

Ryan Hoover: Even when I was a kid, I tinkered with entrepreneurial things like buying and selling on eBay and modding Xbox’s and doing stuff like that. I love the idea of how do I avoid getting paid by the hour? How do I find a way to make money for my impact or my output? And I always kind of hated getting paid by the hour because it’s always this thing where you could work really, really well or terribly and you get paid the same amount. That was just never super motivating for me. I had always tinkered with entrepreneurial things, but I didn’t move to Silicon Valley in 2010 and say, “I’m going to start a company and I must start a company.”

Ryan Hoover: It wasn’t something that I required of myself. And fast forward to probably 2013 that was very organic in how it formed. It wasn’t supposed to be a company. So, again I don’t think there’s a right way of approaching it, but I’m I’m happy starting companies. I enjoy the autonomy and having the ability to get rewarded both monetarily or in other ways because there’s more than just money in startups for more than just my time.

Shaan Puri: Yeah, for sure. I know that you said there’s no right way to do it. There are some wrong ways to do it?

Ryan Hoover: Yeah.

Shaan Puri: In general there’s actually typically more wrong ways to do something then, it’s better to focus on those and just eliminate those as possibilities than try to say, “Oh, this is the right way to do it because X person did it that way.” Because you’ll find another person did it in a different way. Success typically has many, many flavors. Failure sort of boils down to the same five. That’s what I’ve seen so far.

Ryan Hoover: Actually that’s how you build usually a lot of good products. It’s very unclear what the right product is, like the right UX, the right thing, but there’s some obvious pitfalls or some obvious things that you should avoid. In some ways, when we build new features, we think a lot about, okay, we’re not going to do X, Y, Z because we had high confidence that these are going to be not the right solution, but we don’t know about these but they have potential.

Ryan Hoover: So we’re going to explore them and figure out quickly do they actually work. Which is a lot of what you’ve done it. With all of your entrepreneurial and products you’ve worked on is quick iterations and testing.

Shaan Puri: Sometimes too quick. You launched Product Hunt, you have less… let’s take it from, how’d you get from 0 users to 30? You said that was people you knew in the Bay area who you thought might like this. 30 to kind of let’s take it to 300 and 3000. Tell us how you made those jumps because I think as an entrepreneur… I moved to Silicon Valley six years ago and before that I was sort of reading and digesting everything from afar. I was living in Australia, so the other side of the earth and, I remember the part that I felt there was the least clarity on was like, “Okay, I know how you come up with ideas and get it started, find co-founders and go do that, and I know what growing looks like.” But what about that in between part when… how do I get my first 100 people, my first 1000 people.

Shaan Puri: How did you go about doing that for Product Hunt?

Ryan Hoover: Yeah. The things you do in the beginning are different things you do later on. In the beginning, a lot of is just like, how do you get, first 100 1,000 10,000 and so on? Certain strategies worked really well in the beginning and then they of course had diminishing returns, we had to find new strategies. In the beginning it was friends. 20, 30 people friends. First few 100 subscribers were through Twitter primarily. Twitter and [Quibb 00:24:21] actually. Quibb was the entrepreneurial community where people shared mostly articles that they found on the internet. And so through those two channels, I just tweeted it out, put it on Quibb, got a couple 100 people subscribe, that sort of one tiny milestone. And then, fast forward some weeks later, there was some organic growth of people sharing it.

Ryan Hoover: That 200 subscribers turns into four five 600 and then we got to the point where… well, the email list was just the starting point, we knew that we wanted to build a website where people could interact and collaborate and have more contributions. Building the website then enabled us to unlock other ways of kind of growing the audience themselves and so there’s a bunch of things we did. A lot of it was word of mouth, which I know is, when you’re building a new company, when you ask how are you going to get users? Word of mouth.

Shaan Puri: Terrible answer, but great when it is the answer.

Ryan Hoover: It’s great when it’s the answer but don’t rely on it because it’s probably not going to happen. But we did certainly have a lot of word of mouth because-

Shaan Puri: What was the word of mouth… Why were people talking about this?

Ryan Hoover: They were talking about it because I think it filled a hole in the market in the sense that on the internet, in the technology world you had Twitter and you had Subreddits and you had blogs and publications, but there wasn’t a sort of community or a place for all the tech world to come together and kind of geek out about the new products and the new things that are happening in technology, increasingly so as blogs and publications kind of killed their comment section. It’s never been a core part of their business and so, I think part of it was a combination of, there’s a sort of hole in the market, that we sort of filled and combined with the fact that also it was a community based products and when people came on it’s something that they wanted to talk about, wanted to involve their friends and so on.

Shaan Puri: One of the things I remember was that I felt like you were building this company brick by brick and the reason I say that is I remember somebody would join or do something, and you would personally reach out on Twitter, and personally give him a little public kind of love but it wasn’t generic, it was like, you’d start a conversation with them or you would say something that does clearly, you wrote it, this is not a bot.

Shaan Puri: You would send emails to people who join and you would ask them questions like, how’d you hear about it? Or what do you think of this? Here’s what we’re thinking of… Like I just pulled up, this is November 22nd, 2013 this is in my email. I don’t know what the first email you sent was, but this is the second. So you said, “Hey Shaan, my Product Hunt LinkedIn MVP.” You’re using LinkedIn at the time, “… is showing signs of traction. I haven’t promoted it outside my own blog, Quibbe and a couple of tweets, and I go about 175 subscribers and 30 kickass contributors. But what’s even more encouraging is the unsolicited emails and face to face conversations people telling me they love it. I think there’s an opportunity to turn it into a real thing. I’m working with my buddy Nathan to build this out and I would love your opinion. Would you mind if I shot you the mockups and a couple of questions?”

Shaan Puri: I think that this worked beautifully on me. I mean I wrote back like a essay because you were… the people who liked Product Hunt in the beginning, were that Silicon Valley know-it-alls of the world. We love products. We love giving our opinion. We love seeing mockups. It’s like I’d rather see a mock up than a live website, because there’s something about that early early that you are giving us.

Shaan Puri: And you kept that going for a long time. I remember you had public mockups up available for the whole community to look at before you would release a feature. And so you are doing this stuff brick by brick and that’s what I want to highlight because most people just build it and sit and wait. I remember you were pounding emails out, pounding tweets out. Tell me about how you were doing that and why did you even think that was the right thing? because that’s rare. I would say most people don’t really do that.

Ryan Hoover: Part of it was just fun actually, to be honest. A lot of what I’ve experimented with in different products is just like, this just sounds fun. I woke up every morning and sort of had this bug that I just had to explore this further. Part of it was enjoyable. Two, what I realized and knew quickly was, with communities, you need to feel alive and it needs to feel like there’s momentum. I knew that, okay, I should just continue to do what’s working, which is doing a lot of manual things, like welcoming people directly and personally through email and Twitter and so on, and just keep doing that and make sure that we can trickle in more users and get more activity going so that when you come here next week, it actually is, “Whoa, there’s more upvotes. There’s more comments. Oh there’s this that I know through the technology world is now commenting.”

Ryan Hoover: It starts to feel like there’s this buildup and that just attract people or is like, people want to be part of something new and cool, especially in this demographic of like tech early adopters. I think that sort of advice and realization was once you find something, just keep doing it and do it until it stops working.

Shaan Puri: Right. And so you were just waking up 5:00, 6:00 AM, grab a coffee, sit in a coffee shop and talk to people all day. Is that right?

Ryan Hoover: A lot of it. Yeah. A lot of that. And using things like Intercom to see who is signing up and, there is even a moment when it was kind of cool when Intercom has this feature where you can see in real time who’s on your website. And when you build something and people use it, it’s like a satisfying feeling. It’s like the most amazing feeling and it’s even more better when you can see, oh this person I know is on it. Ashton Kutcher signed up one day and Kevin Rose and I was like, “Whoa, these people that I’ve followed in my head for a long time, they’re like using this thing we built, that’s really cool.”

Shaan Puri: Right. And I remember you were almost amplifying it because I remember I have a different email here where you’re like, “Hey Ashton Kutcher signed up and he wants to do X or something like that.” And you were like, “I’m thinking about sending him this. What do you think?” And I felt like Ashton Kutcher signed up for my goddamn app in that moment because I was like, “This is exciting. Yeah. We should try this.” And I was like, “You would take a nugget of something good and like amplify it.” And I think that I’ve joked around with friends that I feel like you were the first guy to build your business on Twitter that had nothing to do with Twitter. And today in this other company we invested in Lambda School, the founder Austin already he’s doing the same thing. He shares every victory on Twitter and people love it.

Shaan Puri: And he’s basically building the… he’s… there’s this drum beat of good news and interesting stuff on Twitter every day. Have you seen what he’s been doing there?

Ryan Hoover: Yeah, yeah. I think he’s done an amazing job of telling the story and, I think the best way to do so is to highlight other people’s wins. I think the other day he tweeted something like, “This is the first time one of Lambda School students actually is making more money…” [inaudible 00:30:15] kind of job, “… making more money than anyone that’s…”

Shaan Puri: Anyone that’s [crosstalk 00:30:18]-

Ryan Hoover: Including Austin himself and I’m like, “Wow.” I joked him like, “Austin, you should probably go through Lambda school then, maybe you can make more money.” It’s pretty impressive what they’ve done.

Shaan Puri: That’s amazing. All right. You take it to use that sort of manual building block strategy. You get up into the few thousands subscribers. What happens from there? How does this become… and give us a sense for the scale, I mean millions of visitors every month is where it got to, correct? How did you go from there to there?

Ryan Hoover: Beginning it was friends than it’s some word of mouth and then it’s a lot of manual inviting and part of that’s to… actually one thing I didn’t mention is there were also moments where I see people who are engaged and I would actually email them and say, “Hey, do you know two people, two people that might be interested in contributing and being a part of this which.” Today if I do that, two more people using Product Hunt’s not going to be meaningful. But then, actually it was, getting a couple more people and email 20 people, it actually is meaningful and so, the other strategy that was useful in the beginning actually was press. And this is again something that most startups need to avoid. Press is usually going to drive a lot of users, especially not sustainably, but for us it was relevant because the tech press, the people that read TechCrunch or The Next Web or others, those are the same people that want to visit Product Hunt.

Ryan Hoover: And so I did some guest blog posts in Fast Company and some others. In fact, there’s posts on Fast Company about how we got our first 2000 users that kind of goes through some of these details. And then we also like built a really good relationship with press by basically trying to help them in their job. So we’d find really cool, interesting products and companies and every now and then I would email someone at let’s say [Josh Constin 00:31:52] at TechCrunch and say, “Hey Josh, I know you’re really interested in consumer social, here’s this new app that we found through Product Hunt it’s really cool.”

Ryan Hoover: Hopefully it was helpful. In some cases they’re like, “Oh cool Ryan, whatever.” In other cases they’re like, “Oh this is really cool. Can you introduce me to the founder.” Or, “Oh yeah, let me write about that.” What that would do is they’d feel like an obligation to link back to Product Hunt because that’s sort of where they found it through me. Then they also just hopefully thought I was being helpful to them in their job and whenever you’re helpful to someone it keeps you top of mind Ultimately.

Shaan Puri: How do you know if press is good for you or not?

Ryan Hoover: I think it depends on the goal. Press can be good, sometimes for use acquisition, sometimes it’s a fundraising strategy. Sometimes recruiting strategy. If you have a really good New York Times piece that might add more legitimacy to future hires. It kind of depends on the goal that you’re trying to achieve. And again, most companies getting tech presses not actually going to lead to actual users, but if it is like Product Hunt, then why not pursue it and double down on that strategy.

Shaan Puri: Right. So you grow the company. Were there moments along the way, where things just totally weren’t working? Where either you’re like, “Oh, we’re AFT here.” This company’s going to die, or were you’re just like, “I totally think this is going to work and, blup, nope. That didn’t work.” Tell me about some of the kind of the downs that happened along the way.

Ryan Hoover: I think the… definitely a lot of those, not going to lie, which is expected. Not everything you build is going to work ultimately and that’s why it’s so important to have really smart guesses, but then figure out which ones actually work as fast as possible, which usually means you got to build it or build some sort of MVP or something. We’ve gone through a lot of failures around the product development and the features we build. Probably the biggest costly mistakes which I take full responsibility for, was, this was about 2015 or so. This was after we raised our Series A, we had long runway lots to explore. Part of the vision and the direction was okay, we had a really amazing community in technology. Cool places to discover new apps in tech products and so on. We believe that this can expand into other categories that have similar dynamics. For example, gaming, had come previously from the video game world.

Ryan Hoover: The gaming community has similar dynamics where game creators, they also really want distribution. They need users. They want feedback from a community. And there really wasn’t a great community place to discover, here the new games today and a discussion with the creators of the games and the people that love the games. Same with books. Books is a similar dynamic where their books coming out every single day. How do you find the coolest new books every single day? How does an author communicate even with their readers? Right now that it really doesn’t happen all that much. It’s mostly authors going on podcasts even today and that’s about it.

Shaan Puri: Right.

Ryan Hoover: And then the third piece was podcast too. Podcasts has a similar challenge. Podcast creators want distribution, want discovery want community. We started building out these verticals and we changed the product design deck, kind of have these, almost like our own version of Subreddits to an extent, except they were very minimal in that.

Ryan Hoover: Here’s a place to discover the newest games today. Here’s the places to discover the newest books and then podcasts. And over several months we spent designing these experiences and building them out and and even hiring people to kind of lead on the community side in each individual vertical. The problem is, ultimately what we found is, it didn’t lead to growth and we just didn’t build a good product actually is the main issue, for those categories.

Shaan Puri: What happened? What’d you get wrong?

Ryan Hoover: There are a few things. One, it all starts with number… one is the product experience. We didn’t want to clutter the overall product.com experience by drastically changing the experience to adapt to all these other verticals. And so let’s say gaming as one example, we want to keep it simple, daily feed, up folk comments, et cetera.

Ryan Hoover: It’s similar and it feels familiar to the rest of the community. But the reality is in gaming you don’t want X-Box and PC and mobile, all these games mixed together in the same feed. You probably play one, maybe two different consoles or PC. That’s what you play on. You don’t want to see all that mixed together. So, the experience for someone who’s a really hardcore PC gamer is pretty awful because you have all these different types of platforms being surfaced and it just was a terrible experience, you know? And then podcast also, it wasn’t ideal experience because this was a web based, primarily desktop focused experience. You’re not going to really go generally to a website to listen to podcasts, you want to on your phone where you’re at the gym or you’re commuting. That was the major issue. it’s just the product experience was not great.

Ryan Hoover: There’s two big directions we could take. We decided to incorporate it all in the same domain, but we also considered spinning it out into gamehunt.com and podcaston.com. We didn’t do that because that would just also require a lot of effort. However, it would have allowed us to be more flexible in the UX and really create something authentic and native to that community. if we went that direction, maybe things would be different. But we ended up failing on that and then kind of backtracking and killing off those categories.

Shaan Puri: You end up deciding to sell the company. You sell it to AngelList. You told me a little bit about how that came about because I was in the process of selling my company. I said, “Hey, how the hell do you do this?” And you told me about this walk you took with Naval. Tell me about the walk with Naval.

Ryan Hoover: Yes. Naval invested in our seed round. We raised two rounds. One was a seed round basically going into YC and got a lot of great people involved and then towards the end of YC we raised a Series A and so we had two rounds. Naval was part of both of those. Going back, I always admired AngelList. I used to browse AngelList looking for cool products and companies and literally on a Saturday morning I would just do that and command, click on a bunch of URLs and say, “Oh that’s cool. That’s cool.” Because I’m a weirdo. But obviously-

Shaan Puri: That’s my Coachella.

Ryan Hoover: Yeah. That’s [crosstalk 00:37:44]-

Shaan Puri: 22 AngelList tabs. That’s my Coachella.

Ryan Hoover: I’m that guy. But obviously AngelList was not built for product discovery and everything but, so I’ve always kind of admired what they’ve done and what they built and so fast forward, this is 2016 Naval had been an investor, so he’s been in the loop and the whole process and everything. We were in the process of exploring do we raise Series B or do we pursue acquisitions? So kind of, I think one important thing for founders to take to heart is optionality. Optionality is everything, doesn’t mean you have to pursue all options, but if you have an acquisition offer and a Series B offer that’s like 10 times better than just having one offer.

Ryan Hoover: Naval and I spoke and… I’m trying to try and remember exactly how the conversation proceeded, but it was sort of a mutual thing. I went to him and in the back of my head I’m like, “I wonder if there’s an opportunity to work together?” And then meanwhile he… I think he-

Shaan Puri: You strike me as somebody who’s not going to bring it up though. It’s like, this would be great, but I’m not going to force it. I have too much respect almost to bring it up kind of overtly. It seems like almost he brought it up and you’re like, “Hell yes.”

Ryan Hoover: He was the first one that explicitly brought it up. It’s kind of like in dating when you’re friends with someone and you maybe start to flirt a little bit and then you’re both kind of know, “Okay, I think he might be in to me. She might be into me.” So I think it was sort of like that and-

Shaan Puri: So you kissed?

Ryan Hoover: Yeah. Me and Naval kissed. It was very affectionate. He’s got soft lips. I hope he doesn’t hear this. From there we had more serious conversations of figuring out, okay, what would this look like and how would this work? And we have a distributed team, your team is centralized. How are these cultures going to blend? It was maybe three or four months of sort of discussions and diligence to come to a final conclusion there.

Shaan Puri: Right. You sell the company, you’ve got money now, what happens the first day money hits the bank? Were you sitting there refreshing, Wells Fargo over again or what?

Ryan Hoover: Some people, they love to go celebrate a big thing. Actually me, I flew to LA that day, I think it was a Friday and my girlfriend lives in LA and we’ve been together four years now and we actually just went to a restaurant and I ordered of course a rotisserie chicken and some Brussels sprouts and I think I had one glass of wine, that was at Eric’s sparkling wine and that was it.

Ryan Hoover: Now I don’t know because the feeling of leading up to that was just a lot of stress, as with any acquisition or fundraise process. It’s super anxiety inducing and especially this situation because there’s like… when you’re raising money, you have this… you’re sort of in the middle as a founder and a CEO, you have your teammates. You have your investors. You have yourself. You have the acquire. And you’re sort of stuck in the middle of how do you make everyone happy and, inevitably not everyone’s going to be perfectly happy. There’s going to be trade offs. That was the most stressful time in my life to date, was the leading up to that because I was at any moment a deal could fall through and I’m sort of responsible for all these people’s jobs and investors and everything else. I think for that day it was a sigh of relief, a little bit, more than anything.

Shaan Puri: So you told the waiter, bring out the sparkling wine.

Ryan Hoover: Give me one glass of sparkling wine. A Prosecco please.

Shaan Puri: I think that’s when the kids call Molly.

Ryan Hoover: Yeah. I know Molly that night. Then it was really just back to work I guess. I mean back to work in, in terms of like how do we make sure everyone is comfortable? Everyone feels taken care of. How do we work together in this new organization? But now it’s been two and a half years later and we’re still just back to work I guess.

Shaan Puri: I love it. My goal with this podcast is interesting people telling their true, which happens to be really interesting stories. And then the other part is a level of transparency around numbers and money so people can get educated because money’s this weird taboo thing we’re like, “Don’t talk about how we got it, how we spend it, how we invest it, how we earned more of it.”

Shaan Puri: Which is strange because the more open we are, the more people can kind of better their own situations. It won’t effect your situation. Give somebody who’s listening to this and people who are listening to this the way I imagine it is, you’re commuting to work. You’re an employee at a job today. You dream of startups. You’re there working at a startup or you dream of starting one one day and they can relate to kind of your story by saying, “Hey, he was at Play Haven.”

Shaan Puri: What were you making when you’re at Play Haven? What was your salary then?

Ryan Hoover: I think it was… I got one or two raises over the years, but I think I ended at 120,000.

Shaan Puri: Right. So you’re making $120,000 a year. Great salary. You’re got this job. You got the certainty, you ended up taking a leap of faith going and starting your own thing, which is fantastic. And now fast forward to today. How do you think like… I guess what’s your relationship with money today? Are you… is this something you’re really driven by? Do you not even look and don’t even care? Are you trying to explore new ways to make money? Tell me about how you’re thinking about money now.

Ryan Hoover: Yeah. I think I… so I was able to buy a condo in San Francisco, which is a huge milestone that is hard to achieve here after that acquisition and that was partly an investment decision as well, which so far according to Redfin is in well. let’s see.

Shaan Puri: You got to love that Redfin estimate.

Ryan Hoover: I know, I know. We need more housing here in San Francisco, that’s for sure. For me, I’ve been fortunate I came from like a middle-class family, so I’ve never had challenges or worries about food or a shelter or anything like that. I’ve also been able to go to college without having to pay for it. I did work through college, but as a part time job but it wasn’t like I had to work to pay off $80,000 in debt or things like that. I’m super fortunate in that sense. In some ways money hasn’t changed dramatically, now today however, where I think about it as I’m trying to think longterm in my sort of professional career. I have multiple things going on right now.

Ryan Hoover: One, Product Hunt is still primary focus and frankly a lot of my net worth is tied up in AngelList so I’m incented to make sure this is successful, with private time being part of AngelList. That’s sort of one piece, and then I have, the fund I started two, which is another piece which I’m trying to-

Shaan Puri: And that’s called the Weekend Fund?

Ryan Hoover: Mm-hmm (affirmative)-

Shaan Puri: Love it.

Ryan Hoover: And that’s partly to learn, I always wanted to invest in, partly to learn but also like we’ll see in six, seven, eight years if I make any money on it. But that’s another opportunity for me to make money and kind of gain leverage in a different way. Naval actually talks about this and a lot of this podcast around how do you gain leverage and-

Shaan Puri: You should probably just stop listening to this podcast and go listen to the Naval’s podcast. That’s what I would do if I was you. That’s my actual recommendation. I would start with that and then somehow wander back here eventually.

Ryan Hoover: He’s got a lot more insights than I have, that’s for sure. But I’m really trying to explore, okay, how can I have multiple parallel things going on that gain leverage and either create money in some way or impact in other ways. And that’s not using my time so this is going back to what I said before. I hate getting paid by my time. With the fund of course I spend a lot of time on it, but my time doesn’t have a direct input in the outcome.

Shaan Puri: Right.

Ryan Hoover: It’s really do I-

Shaan Puri: Pick the right companies.

Ryan Hoover: Pick the right companies and did they succeed over the long term and does that return capital to me in the LPs in the fund. And the same is kind of true for Product Hunt and AngelList too, is if we’re successful when we do really well, the stake and equity that I have an AngelList will hopefully grow as well. I’m sort of… ‘my real payday’ is still TBD and it’s out there because a lot of it’s kind of invested in the fund in AngelList itself, but for me, I don’t know.

Ryan Hoover: I don’t have to worry. We don’t have to worry about food and shelter and unless something bad happens, but I certainly can’t retire that. I’m far from that.

Shaan Puri: Plus you basically eat rotisserie chicken anyways, every male.

Ryan Hoover: Yes. Yes.

Shaan Puri: I think you’re safe no matter what-

Ryan Hoover: And I buy [crosstalk 00:45:07]-

Shaan Puri: $7 at Costco? What are we talking here? Where are you getting your chickens?

Ryan Hoover: The pro tip actually is a… I eat the same things all the time and then a lot of it’s like spinach salads and stuff and so, but on Instacart there’s like a bulk, it’s not a Costco, but it’s actually where all the restaurants go for bulk foods.

Shaan Puri: Right.

Ryan Hoover: You can buy at two and a half pound bag of spinach for $4 there. AI just buy that and that lasts me in quite a while. Pro tip.

Shaan Puri: Nice, the Ryan Hoover diet. Fit 90 days while building your company. This is your new-

Ryan Hoover: That’s my next book. That’s my other lever. I’m going to write a book.

Shaan Puri: Of course. If you ever written a fitness book, are you even trying? Is kind of the way I feel about it.

Ryan Hoover: That’s the name of it actually.

Shaan Puri: All right. What if you’re 21 today? Let’s say let’s take product underway. You have your time back. You have your youthful energy back. You’re 21. You want to make $1 million. What sort of thing would you do today? Where would you spend your time?

Ryan Hoover: I mean, my path has always been spending my time on the things that I find fun and interesting, and I find that motivating because one, is just, if you’re having fun, then you’re not going to stop. It’s going to be the thing you want to wake up and do or the thing you want to do on a Saturday afternoon. I would prioritize those types of things.

Shaan Puri: What’s fun for you nowadays?

Ryan Hoover: I mean there’s the non-work stuff like going to, live music is fun, but when it comes to more professional fun, I really enjoy investing and speaking with founders and researching spaces and that’s really enjoyable, Project Hunt is still fun for me of course. Partly because we’re building new things. We are building entirely new site and brand so I’ll tell you about offline actually. [crosstalk 00:46:40] Twitter as well-

Shaan Puri: We are going to go grab some Chinese food and talk crazy ideas after this, but I do want to wrap it up on one note. So you have the Weekend Fund. Tell us a little bit about that. How should entrepreneurs reach you? What types of entrepreneurs are you looking for? Tell us how you’re going to turn my $10,000 from the Weekend Fund into $10 million. That’s what the people want to hear.

Ryan Hoover: I don’t know if I can do that. I’m not going to lie. $10,000 to $10 million. It’s investing in early stage. Usually it’s the first round of funding so, I say that because different definitions of what pre-seed even means or seed stage and it is broadly focused. So invest across everything from an audio and voice company to B2B, SAS to shipping logistics. So, all over the board. Now there are some spaces I’m really excited about. I could go deep into why I’m excited about them, but audio and voice is really interesting. Promote distributed working is a super interesting category. Lots of problems to be solved there. And then another one that I’m personally interested in, low and no-code tools. Things like Retool or Airtable or Glide and others that just allow people to build things, faster and more efficiently that maybe aren’t engineers.

Ryan Hoover: Maybe they are maybe they’re not, which actually if that space does really well, Product Hunt will also, just see more activity and more engagement and more… there’ll be a bigger need for Product Hunt to exist if that [crosstalk 00:47:54]-

Shaan Puri: Double leverage.

Ryan Hoover: Double leverage. Invest in the company that then leads to more products being built, then leads to more launches on Product Hunt and so on and so forth. I’m just investing early stage 50 to a 100 K check size typically. And it’s been fun. I brought on an awesome teammate to work with me part time as well. [Vetika 00:48:13] she is in London and she’s just helping a lot and has been a cool partner to kind of work with on this as well.

Shaan Puri: What’s the right way for an entrepreneur to get your attention nowadays?

Ryan Hoover: That’s a good question.

Shaan Puri: Launch on Product Hunt?

Ryan Hoover: Maybe. For the past almost six years, I wake up every morning and see new products at launch. I see so many things, and a lot of what I tried to understand if it’s super early and there’s not much traction or data to even prove out that this thing is working, is to understand like what’s unique or different about their approach or their thinking around the space. And some might call it like, “What’s the insight or the non obvious thing that this founder, this team discovered?” Because oftentimes I’ll meet an entrepreneur and not that I am… I certainly am not the smartest person in the world, but if I can almost foresee all the answers to their questions, that something wrong, meaning they should know way more than me about a space. They should almost be educating me and surprising me with something that they’ve seen that the market doesn’t see.

Ryan Hoover: Sometimes it’s requires kind of weird out there ideas. This can make it really great investment sometimes or sometimes they’re just weird and out there and no one wants to think you’re building. I like to just discover sort of the things that are non obvious that haven’t been proven, that are… might just seem weird.

Shaan Puri: We have Ryan Hoover. Ryan Hunt [crosstalk 00:49:29]-

Ryan Hoover: I’ve gotten that before. People have called me Ryan Hunt [crosstalk 00:49:32] article-

Shaan Puri: Is there a famous Ryan Hunt? I feel like there is.

Ryan Hoover: Maybe. Maybe.

Shaan Puri: There is a baseball player, but nobody watches baseball anymore. All right, we have Ryan Hoover founder of Product Hunt, investor in the Weekend Fund. You can find him on Twitter. You can find him, I believe in LA nowadays so, if you’re trying to go bump into him on the street, that’s the place to find them but, thank you so much for coming on the podcast man. I really appreciate it.

Ryan Hoover: Yeah, thanks Shaan.

Shaan Puri: Sweet.

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