Ryan hoover

Ryan Hoover

Founder and Investor Product Hunt and Weekend Fund

Ryan Hoover is the founder of Product Hunt, the place to discover the latest in tech. He is also an investor in early stage startups, investing out of a fund he started in 2013 called Weekend Fund.


Ryan took his love of products and created Product Hunt, a place to share and discover new products, which sold to Angel List for a rumored $20M. Ryan shares what makes a great product, what he looks for in products as an investor, and how you can get started in product management.

Show Notes


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[00:00:08] (Music) Welcome to the CodeNewbie Podcast where we talk to people on their coding journey in hopes of helping you on yours. I’m your host, Saron, and today, we’re talking about Product Hunt. A little over five years ago, Ryan posted a tweet. It read, “Just announced a new experiment, Product Hunt.” It got 36 retweets, but that link to an email newsletter prototype turned into a full product, a full startup, and a few years later it sold to AngelList for a rumored 20 million dollars.

[00:00:40] RH: My name is Ryan Hoover. I’m the Founder of Product Hunt, also do some investing out of a fund called Weekend Fund and I do a lot of things but mostly just working on Product Hunt is my day-to-day.

[00:00:51] SY: But the thing is Ryan isn’t an engineer. He knows a bit of code, but he’s more of a product guy. In fact, he spent years researching, writing about, and developing products, and then created Product Hunt, the place where you can discover products. He shares how he built Product Hunt, what he’s learned about product management, and what he looks for in products and founders that he invests in. After this.

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[00:04:01] SY: So you are probably best-known, at least to our community, for Product Hunt, which is the place to discover your next favorite thing, and the rumors are that it was sold to AngelList for about 20 million in 2016. I don’t know if you’re able to confirm or not, but that’s the rumors anyway. And so in building a company that was so successful that it got acquired and is such a darling, people freaking love this thing. They love Product Hunt. How were you able to do something that feels very technical without being super technical yourself?

[00:04:34] RH: So I’ve always dabbled with technology. Back when I was a kid, I built websites for fun, hacked my Xbox for fun, and I think video games is probably my gateway into a lot of the world of technology and IRC and all these other things. So I’ve always dabbled with technology and built things. Oftentimes though when I built them, like the first website I built was actually largely powered by like Dreamweaver.

[00:04:56] SY: Yeah.

[00:04:57] RH: And so for me, I’ve always enjoyed making things and actually this goes even beyond I think code in products and websites, but I also used to film and like create a lot of videos. So when I was dabbling with things, a lot of it was just hacking things together and figuring out like, “How do I use the research and skills I have to create something that maybe it’s an MVP or just kind of a kernel of an idea?” But that was usually kind of how I started.

[00:05:22] SY: So when you were growing up and you were building all these things, both technical things and videos and more creative other stuff, did you ever hit a wall where you said, “Man, if only I really knew how to code I could do these things and because I don’t have that skill, I’m stuck”?

[00:05:41] RH: You know I taught myself HTML and some basics of how to get a website up when I was in high school. I took some classes in college, minored in computer information technology, and I actually took some CS classes as well in addition to that and I actually found it just not fun, not as enjoyable once I got to a certain place, and certainly with anything that you learn you hit a sort of wall and you have to like really power through it and I just didn’t have enough motivation to power through it. I didn’t see myself as someone who would sit at a computer and code like as a primary function of my role. I much more enjoyed the aspects of design and product design and marketing and later on more community building, but certainly I wish I could code. I wish I could do a lot of things, but you have to ultimately prioritize and like focus on the things you want to do and the things that you are good at, I think.

[00:06:31] SY: I really appreciate that because being the founder of CodeNewbie, you might assume that I think everyone should code and I don’t. I think that if you want to code, then you should do it and we’re here to support you and encourage you and make sure you cross the finish line if that’s what you want. But if you try it and it sounds like between your computer science classes and the minor and computer information technology and all that, it sounds like you gave it a very honest effort and you’re like, “That’s not for me.” And that’s totally cool.

[00:06:59] RH: Yeah. Yeah. It takes a lot of different skills and talents to build a great product, a great business. And so I feel like in the past decade, we’ve had a lot of focus on engineering, that’s the thing that you do if you want to get into technology. Not everyone needs to be an engineer. Not everyone should be an engineer. And if everyone is an engineer, then we actually wouldn’t build great businesses if it was purely focused entirely on that.

[00:07:22] SY: That is a good point. So you describe yourself as being a product guy. What does that mean?

[00:07:27] RH: Yeah. I don’t even know if I like that term anymore because it’s so vague, but what I mean by it is I really and this is why Product Hunt started really is I just love playing with products and exploring them. I love the creativity of building a product and I used to, prior to Product Hunt, really I would browse the App Store in Japan and just see what was popular and what people were playing with and I just found it fascinating and interesting to see how they were different than maybe some of the products I was familiar with.

[00:07:54] SY: I’m curious. What differences did you see in the Japanese app market compared to the US?

[00:08:00] RH: Yeah. So some of it, and this was back in probably 2010, 2011 is when I was really kind of exploring. It was around the time I moved to San Francisco. It felt more complex actually, but a lot of it felt a little bit more colorful, more complex in terms of number of features and things. If you look today, there’s actually a really good video by Connie Chan from Andreessen Horowitz that she published recently that goes into some of the differences between the business models of the east and the west and how companies like Tencent have… they basically build the modern day LOL homepage in some ways within a mobile app with transactions and if you look at WeChat is one example. It has built-in app store essentially along with peer-to-peer payments, so many other things unlike many other western apps, which really usually focus on one kind of singular use case.

[00:08:50] SY: That’s true. Yeah. So I want to talk about what happened before Product Hunt and how you ended up building and creating Product Hunt. Let’s go back to that minor in computer information technology. After you graduated, what did you do? What was the plan?

[00:09:07] RH: So it was actually my senior year in college. I grew up in Eugene, Oregon, went to school there at the University of Oregon, and the senior year in college I actually found out there was an internship opportunity at a video game company. It was an unpaid internship and so I applied. I got it and that internship after I graduated turned into a full-time role which then I moved to Portland, Oregon, and so I learned a lot about marketing. I quickly moved on to product management role at that company and then ended up segueing into, well, moved to San Francisco in 2010 to join another company in the gaming industry.

[00:09:40] SY: Yeah. So marketing to product development feels like a big jump. How did you make that transition?

[00:09:48] RH: It’s one of the hardest roles to get a job in, in part because there’s just so few product managers relative to engineers or even designers and other functions in most companies and so there’s a lot less supply, I guess, of jobs. And the other challenge is that most companies won’t hire someone unless they have product management experience before. So then it has another challenge like, “How do I get in?”

[00:10:11] SY: Yeah.

[00:10:12] RH: For me, it was very organic and I was fortunate in that I was doing marketing initially, but I reported to the VP of product and we collaborated a bunch and we would jam on different product ideas. At the time, we were focusing a lot on Facebook’s API and building our platform on top of Facebook. And so I would constantly be digging into Facebook’s API changes and actually try to observe like what are they doing and how could we leverage or change the direction based on some of the new capabilities that they’re offering. So there’s a lot of these conversations with Tony that led eventually to him bringing me on as a product manager because they were looking for someone in the role.

[00:10:50] SY: So at that point, did you have side projects you are working on or a personal portfolio where you were doing some product stuff or was it mostly that interest in that research?

[00:11:01] RH: At that time, I was not doing any side products. I was focused pretty much a hundred percent on work, but I was constantly like tinkering and exploring ways that I could take these weekend learnings and apply into things we are building or working on in the company.

[00:11:15] SY: I think the other thing that makes the product manager position a little tough is you need to have product management experience, but you also need to have management experience, right? Because you’re managing a product, but usually that also means kind of managing engineers and other coders and kind of bringing the team together towards a specific goal. And that’s tough. It’s tough to get that management experience. How did you manage that?

[00:11:43] RH: Well, kind of couple different ways of putting it. I would say it’s ironically product management. Even though it has the word management in the title, I never managed anyone directly. I had no direct reports and I’ve seen this pretty common in product management roles unless you’re like VP level or something like that. A lot of times the product manager is an individual contributor and they have no authority in some ways. So they have to earn it and it becomes a role that requires just clarity of thinking and communication. And since you’re sort of interacting with pretty much everyone in the company from sales team to engineers, to designers, to customers, external customers, you just have to be really good at communicating. And I think that’s one of the most important aspects of that role.

[00:12:31] SY: Yeah, absolutely. So I think the last thing that you did before Product Hunt is PlayHaven. Is that the company that we’re talking about?

[00:12:40] RH: So the company that I first joined was called InstantAction and then I joined PlayHaven in 2010 and moved to San Francisco.

[00:12:48] SY: And how was PlayHaven? What were you up to there?

[00:12:50] RH: Yeah. So that was also a product management role and so I followed one of the execs that actually worked at InstantAction and he was joining this new company called PlayHaven, about 10, 12 people at the time when I joined, and we were focused on supporting mobile game developers, like building tools for them. And that was a really awesome experience, learned a ton. The scariest part though was shortly in the beginning. When I joined, moved all the way from Oregon to San Francisco, the company, it wasn’t in a bad spot, but we were at this place where the product that they built when we joined wasn’t a product that would scale to be a venture-backable business. And so it was sort of at these crossroads where the company and the team needed to figure out, “We can’t just go down this direction forever. We need to figure it out. We need to change directions entirely and essentially pivot.” There were some layoffs and I ended up surviving some of those layoffs and we ended up, me and Andy, the CEO, and the rest of the team, really got together and thought about like, “What does the market need and what are we observing? What are we learning?” We know that, long story short, building out these tools that we realize that a lot of game developers were basically reinventing the wheel, they were creating ways for them to message their users in game, to do cross promotion between their various titles. Basically all these things people were building in-house themselves. And so instead we said, “Well, why don’t we allow these game developers to focus on building the game and we’ll focus on building the tools so you don’t have to do all the other stuff?” We did well, grew from ten people down to six to like a hundred or so before I left.

[00:14:25] SY: Oh, wow! That’s a comeback. That’s pretty good.

[00:14:30] RH: Yeah. Yeah, it was a good experience. Now today it’s the company and we’ll see where they go, but it’s the ups and downs of startups. I guess I experienced that pretty quickly once I moved to San Francisco. 

[00:14:40] Coming up next, Ryan shares his biggest takeaways over the years of doing Product Hunt. He also tells us what he looks for in the products and people he invests in and how you can get started in product management after this.

[00:14:55] We’ve talked about open source a bunch of times on this podcast, but frankly, open source is so big and complex and fascinating that it needs its own show, and it has one. It’s called Command Line Heroes. It’s produced by Red Hat and it’s hosted by me. That’s right. I’ve got another tech podcast talking to incredible people about all things open source. We talk about the history of open source, the introduction of DevOps and then DevSecOps, and we even do an interview with the CTO of NASA. And that’s just the beginning. We also dig into cloud and serverless and big data and all those important tech terms you’ve heard of, and we get to explore. If you’re looking for more tech stories to listen to, check it out at redhat.com/commandlineheroes. Link is in your show notes.

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[00:17:25] (Music) Tales from the Command Line. It gives us a chance to dig into one particular part of the episode and hear a different perspective from a really experienced developer in the field, Scott McCarty.

[00:17:37] SM: Yeah. My name is Scott McCarty. I am a Principal Product Manager and I focus on containers, like all the technology within containers that enables Red Hat Enterprise Linux and OpenShift.

[00:17:51] SY: Let’s begin. So Product Development, do you remember the first product you ever managed?

[00:17:55] SM: Technically, I’m actually in the first product I’ve ever managed.

[00:17:59] SY: Oh, okay.

[00:18:00] SM: I was at a startup before I came to Red Hat and I actually was like an engineer that helped develop some of the products and then maintain some of the products, but I wasn’t the product manager. There wasn’t even really a product manager per se. We were like a seven-person company, but technically my first product management role is the product because there’s kind of multiple pieces and parts of products that I’m managing right now.

[00:18:22] SY: What are the products that you’re managing? What are they?

[00:18:27] SM: So I manage containers, like the container technology for Red Hat Enterprise Linux and the underpinnings of OpenShift. So like my role basically bridges a few pieces of technology that are in both Red Hat Enterprise Linux and OpenShift.

[00:18:40] SY: That seems like a lot of stuff.

[00:18:42] SM: They’re very technical products.

[00:18:44] SY: Yeah. Yeah. Very intense. Did you kind of level up to eventually have all these under your belt or just right away you were just doing all this stuff?

[00:18:55] SM: There’s a particular framework for approaching product management called “Pragmatic Marketing” and they use a system where they describe 37 different functions that you basically need to meet to get a product out the door.

[00:19:07] SY: Okay.

[00:19:07] SM: In a very small company, a product manager would do all 37. As the product obviously gets bigger and sells more and has more sophisticated features, you break up those 37 boxes into different roles. Product management and product marketing are probably the two big roles, but then you also have sometimes competitive product people that will go analyze competitive products. A lot of times there will be architects that live in the engineering group, but they will do some of the 37 boxes. A lot of the times you may have public relations teams that handle explaining what’s going on. I was an engineer, then I moved into technical sales, then moved into technical marketing. So I was already doing a lot of those 37 boxes and then I moved into product management. So now I’m kind of really doing a lot of those 37 boxes.

[00:19:55] SY: So in your current role, managing all these products, I assume it involves a lot of meetings, maybe a bunch of Trello boards. What does that actually look like?

[00:20:05] SM: I joke probably more than 50 percent of my work is unplanned.

[00:20:11] SY: Surprise tasks?

[00:20:12] SM: Yeah, surprise tasks. Your day as a product manager can consist of talking to legal about three different legal issues, talking to engineering about 42 different things that could go wrong that are going to prevent the product from releasing, talking to QE who’s saying that they can’t test the stuff that engineering is building because engineering is doing it wrong, talking to support because support is annoyed because QE won’t test that thing and so they’re like, “Well, we’re not going to support it unless QE tests it.” It involves talking to consultants who are mad because they’re trying to deploy the stuff on site and it’s not supported because QE wouldn’t test something because engineering didn’t build it in the right way and then you can talk to sales because they’re complaining because they want some new feature that can’t be built because you’re going and fighting the other fire, like there’s just all these different functions that interface with you.

[00:21:00] SY: And remind me again. What is QE stand for?

[00:21:03] SM: Sorry, Quality Engineering.

[00:21:04] SY: Quality Engineering. Okay.

[00:21:05] SM: So they’re the people that build all the tests to make sure the stuff that engineers build actually works, right?

[00:21:11] SY: That sounds important. So it sounds like when you are thinking about product development and you’re managing all these pieces, it sounds like there are a lot of things that could go wrong. I’m wondering what is the worst product development related experience that you’ve had?

[00:21:26] SM: Large product launches are much, much harder. So when I was at a startup, it was actually quite easy. Specific customer that you were helping would come to you and say, “Hey, it’d be really cool if you built X, Y, Z for us.” We would be like, “That sounds like a good idea. Let’s do that. Maybe we can sell that to some other people.” Big revenue streams have lots of customers that are very sophisticated. So when you’re providing a very differentiated product to a large group of people, which is typically what happens when you’re making a lot of money, the requirements are just so much more sophisticated and so then customer X, Y, Z will come to you and say, “Hey, you should build this cool feature for us.” And we’re like, “Whoa, wait a minute. That sounds like that feature could be cool, but it would require changes to all this other stuff and affect all these other customers. I don’t know if that’s the best idea.” You’re always minmaxing. You’re always looking, “Okay, yeah, there could be some incremental revenue we’d gain here, but we might lose revenue over there,” and you got to start to analyze and that’s the hardest part for a product manager, right? I’m putting out all these fires day in and day out but at the same time, I’m looking to the future of our product now, how we’re going to continue to grow the revenue and keep making money, keep producing differentiated features that customers want to pay for.

[00:22:42] SY: Yeah.

[00:22:43] SM: That’s probably the hardest piece of my job right now.

[00:22:44] SY: One thing I’m appreciating is that you didn’t say the most technically challenging products are tough. You said the ones that generate a lot of revenue and I’m really appreciating the fact that the fires you put out are not always technical fires, they’re money fires and business fires.

[00:23:03] SM: Yeah, money fires, legal fires, yeah, all kinds of fires.

[00:23:06] SY: All kinds of things. Yeah. So when you think about your job balancing the purely tech side of things versus the bigger picture of the company and the finances and the revenue and the clients, what percentage of your time, of your abilities is spent in each world?

[00:23:25] SM: You know it depends on what kind of change you’re trying to make to the product. Sometimes there’s legal changes, sometimes there’s pricing packaging changes like how you’re going to sell the product. Obviously, there’s always technical stuff. You’re always adding new features. The biggest problem is talking to customers, figuring out what they need, figuring out what’s realistic, and then backlogging work so that we can get new stuff out the door. Sometimes competitive stuff is harder like a competitor just came out with a new product that is released at a different price point than yours and you’re like, “Oh, my gosh, we got to come out with a competitive thing like a subversion of ours that’s got a smaller feature set that competes at that price point.” PMs in a nutshell have to build buy or partner. They have to decide, you know, build buy or partner, that’s the highest level thing that they have to decide or at least try to influence the organization to do.

[00:24:09] SY: You mentioned earlier that it’s not always the big company. It’s the size of the product which may or may not be related to the company. But is there something about working at a huge company that complicates the product development, product management journey?

[00:24:24] SM: I don’t know if it’s cause and effect in that way. I think that it’s correlation for sure, which means that you have to be worried about it as a problem. Say you’re an engineer right now, say you’re a senior engineer or maybe even an architect and you’re like, “You know, I think I want to get into product management.” I would say at a bigger company it’s still harder. That’s for sure. But I don’t think that’s causal because the company’s bigger. I think it correlates when the company’s bigger because it has better products that are more complicated that generate more revenue. So in that scenario, yes, the requirements for a PM are just harder. To be really successful as a PM and drive a really important product within a big organization is probably one of the harder jobs there are.

[00:25:06] SY: So if someone listening is interested in getting into product development and getting into product management and kind of heading off the team and doing a lot of stuff that you’re doing now, it’s fascinating because you’ve taken such an interesting path to get here. You’ve done so many different things to get to where you are today. But if you were giving advice to someone who would like to end up where you are, what would that advice be?

[00:25:29] SM: I would say the same advice that was given me, just be really good at what you’re doing right now. If you’re an architect, help the PM, help them deal with legal, help them deal with finance and all these things. There’s going to be technical challenges to every one of these legal or finance or competitive challenges that there are or feature requests and things. There is the opportunity for all of these different roles to kind of move into the other ones, but I have to admit you have to be really good at what you’re doing and be a really good expert at what you are and then there will be a natural point where you’re like, “Okay, I’m pretty good at this.”

[00:26:01] SY: Do you feel like you needed all the stuff that came before it in order to do the job you’re doing now well?

[00:26:08] SM: Yes. So I follow a guy named Steven Sinofsky. He’s become like an angel investor, but he was at Microsoft early on. His argument is that you should spend about three to four years in any given role. It should not be a year or two years because in a year or two years, you’ve only barely seen like one product release. You need to see about two big product releases to really be an expert at your role. You might release the first product and you learn a lot during that first launch, but then when you launch the second one you go, “Oh, yeah, here’s all the things we screwed up in the first one. Let’s fix this.” The second one you rock it and then you’re like, “All right, now I’ve outgrown these britches. Now it’s time for the next thing.” Enjoy the journey because you got a long career. We’re all going to be working longer than we probably want to. So enjoy the process.

[00:26:59] SY: And now back to the interview. So when you were at PlayHaven, I believe is when the idea for Product Hunt came to be. Is that right?

[00:27:10] RH: So it’s about three years into working at PlayHaven. I started to get the itch and there are two kind of themes. One, I felt like I wasn’t learning as quickly as I did in the early days. The company was more mature. There is more process, just more people, and there was also some challenges with what we were building like a lot of technical event and some other things. And then two, I really want to build something for myself, something that I was a consumer of, those two realizations I thought “Maybe it’s time for me to move on and find something new.” So I gave notice and didn’t know what I was going to do next actually. It’s sort of in between that moment that the idea of Product Hunt came up and I started to work on that on the side.

[00:27:53] SY: Yeah. And so why Product Hunt? Was it the main thing? Was that the idea that initially grab your attention or where did that particular idea come from?

[00:28:03] RH: I’ve been tinkering with some other ideas and kind of experimenting with like landing pages and just playing around with different concepts, but Product Hunt was the one that really stood out to me because me and my friends are at the time and still today we share what products we’re using, what apps we’re discovering, sort of a combination of one we’re sharing and talking about these products, but then where do you do that online? Where is there a destination to really geek out about these products and intellectually kind of talk about what we think about the onboarding flow? We were nerds in that sense. We like to go deep on some of these things and really thought that there was a hole on the market to host a conversation like that and bring people together that also had similar passions around technology.

[00:28:43] SY: Yeah. So I’m really fascinated by how you validated this because when we think about lean startup and MVP and all that, there are so many different ways to actually implement it. Is it just a landing page? And if you get X number of subscribers or people who hit it, then it’s validated. Is it the number of people who actually contribute to a fully developed platform? At what point do you say, “Okay, I have something here”? So besides your personal interest and your close friends validating it and saying, “We do this anyway, might as well have an online place to do it,” how were you able to validate that this was bigger than you?

[00:29:23] RH: Prior to all of that, maybe the year prior to Product Hunt started, I started writing a lot and blogging and writing a lot about technology and I really enjoyed using writing as a vehicle to learn. By doing that a bunch, I wrote 150 articles in 2013 and some of those were really short, but it’s actually a lot. Every morning I was writing. By doing that, being really active on Twitter, I started building a small but big enough audience where at least when I tweeted or put something out there, there were some people that would notice. When Product Hunt started, I had the idea [INAUDIBLE 00:30:07] and couple weeks prior actually saw this product that was built by this team out of Europe and was called Linkydink. And I saw this product and I thought, “Oh, this is really creative.” It’s a way to host collaborative email digests where you could invite a friend or group of friends and basically they would just post a link and then every day at 5 P.M. the system would actually just email everyone that subscribed to that list these links and so there’s a pretty broad open use case and I thought, “Well, I love products and I love discovering products and sharing with friends. What if I create an email list? I’ll name it Product Hunt because it’s about products and it’s sort of like hunting for products. And what if every day we just shared together through these email list products that we thought were cool and interesting?” And so that’s how it started which took about 20, 30 minutes to actually build that email list and then tweet it out and write about it.

[00:30:52] SY: That’s awesome. That’s very minimum.

[00:30:54] RH: Yeah. It was very minimum and a lot of people assume they hear about the email kind of first approach of Product Hunt and they think that I was curating and I was writing this email every day, but actually it wasn’t even me. I was in some ways curating I guess the people, but the people were curating from day one the products and everything. So Product Hunt has always been community-driven and always been collaborative even it’s like tiny email kind of MVP.

[00:31:18] SY: So when you put that email prototype out into the world, what were you expecting? Did you have your own personal goals of, “If I hit a hundred subscribers, then I’m good. I got it.” You know what I mean? Did you have like milestones for yourself at that point?

[00:31:35] RH: I did not. The way I thought about it and the way I’ve always thought about I guess side projects is, I actually didn’t even call it a project, it was called an experiment in the very beginning. The whole purpose of an experiment is to learn. It’s not to necessarily win or to get to a finish line necessarily, but it’s actually to learn whether it’s working or it’s not or other things like that. So a lot of it was just being very experimental and open-minded and learning how people were using it. It was after, I don’t know how many subscribers we got up to, but several hundred, not anything crazy, but several hundred and then a bunch of people also like kind of coming up to me and saying they enjoyed the email. That was sort of some validation that there was something there. There’s a kernel of an idea that could grow into something much bigger.

[00:32:20] SY: At what point did you say, “Okay, experiment is over, now we need to take the next step,” whatever that step is?

[00:32:29] RH: Yeah. It went from experiment and then it was around Thanksgiving actually, 2013 Thanksgiving. I emailed my buddy Nathan Bashaw and I emailed him initially asking, “Hey, Nathan, I have these email lists called Product Hunt. It’s starting to work, but obviously I want to build a website that people can comment on that’s more interactive, that can build community.” And I asked him, “What would you recommend I use to build this? Should I learn Ruby on Rails? Should I use Telescope?” which at the time was like an open source framework to build kind of like reddit-style communities. Nathan is a really unique person. He is a designer. He’s a product person. He’s also an engineer. So he’s a great guy and we worked on it then kind of remotely as he was back at home we were jamming on different product ideas and specs. As he was sort of focusing on then executing on like building the actual product which was just a simple way to post a link, have comments and upvote, that was basically it, I was then also working a lot on… collaboratively working on the product but also then seeding the community and getting people excited and so getting beta testers in, getting their feedback, emailing people that were kind of signing up, like a lot of really manual community building efforts to get things off the ground.

[00:33:46] SY: Yeah. Yeah. And that brings me back to the beginning of this conversation when you were saying that there’s so much more than code and so much more than being a great engineer required to make a product work indefinitely to make a business work and it sounds like you were doing a lot of the other stuff, the community building, the marketing, the branding, the engagement, even when you think about setting up a beta, that takes organization, logistics, you got to track stuff. There’s a lot of stuff that goes into it that’s outside of a code base.

[00:34:15] RH: Yeah. And we’ve seen a lot of Product Hunt for X, so Product Hunt for different categories of things, and we’ve also seen direct rip-offs, in fact pretty early in the first year. So we had like a Korean version of Product Hunt, a Japanese version of Product Hunt, and a bunch of others and there was even kind of like an open source Product Hunt and none of them took off, none of them sustained, and it’s largely because the process of building Product Hunt, the technology is not what is defensible and what’s most compelling. It’s really the community and the people in it and the brand.

[00:34:46] SY: How did it feel to watch all the rip-offs? Did you take it as a compliment or were you pissed off?

[00:34:52] RH: I wasn’t pissed off. It was validation for sure, especially when people started describing their product as Product Hunt for health foods, Product Hunt for YouTube videos, Product Hunt for music, all of that.

[00:35:05] SY: Yeah.

[00:35:06] RH: You’ve seen that with like Uber, Uber for X, Airbnb for X. So it’s definitely validating. And while I think it’s wise to be cautious of competitors, potential competitors, it’s also like the old saying is like, “It’s probably not the competitors that are going to kill you. It’s usually yourself in most cases.”

[00:35:22] SY: Yeah. When you were building out, especially that first year or two, when you were building out the features and moving it from this email thing where I assume the features are already built for you, you’re just using it, and moving into building a platform yourself, how did you decide what to build? Did you rely heavily on customer interviews, on your gut, your years of product development, know-how, or where did those ideas come from?

[00:35:51] RH: One, always have a vision of what you want to build, sort of what’s your North Star, like what’s the purpose of this thing? But then with that, a lot of the inspiration for what we’ve built has been just looking at how people use the product especially if they’re trying to use it in unexpected ways. I think it’s a really good source of ideas and also source of validation that if you build this thing people will use it. So every now and then we would share mock-ups actually of what we were building and using vision to just annotate and show or rather give people an opportunity to annotate on the mock-ups themselves. A lot of times people would say, “I don’t get this,” or, “This doesn’t make sense,” or, “Hey, what if you did X, Y, Z?” People felt involved and like really part of the process and they were and even if we did listen to them. But even if we didn’t listen to any of their ideas, the reality is by demonstrating and involving them in the process and giving them a preview of what we were building, that built a community and built kind of the brand that we have today.

[00:36:48] SY: Yeah. When you mentioned the North Star, it reminded me that there are different levels, I guess, of a product, the North Star probably being the top level, the high, this is the general direction, this is where we’re all headed towards, and then there’s the, “Okay, to do that, we need to help people do these types of jobs with these types of tasks. Okay, now we’re going to go even further in.” And say, “Okay, but the way you do these tasks is through these three button clicks.” And the buttons will be orange, right? So there’s kind of different layers of feedback for people. At what point did you incorporate users or user feedback in deciding which of those layers to change or to modify and which of those did you decide to do based on what you thought was best?

[00:37:36] RH: Yeah. There’s always the balance and struggle with the things that users ask for. They ask for all kinds of things and they may not have the full picture of what you’re building. So I guess that’s one thing to always take into consideration is the biggest and most strategic moves are really difficult for a user to actually tell you because they don’t have the full picture of what you’re kind of building. So a lot of it is trying understand why are they asking for this particular feature because sometimes the solution that they’re coming up with is not necessarily the right solution, but the underlying problem or need that they’re trying to solve is. So maybe an example of this is we noticed early on that people were creating their own list of products. So they were using other tools like Trello or other list collection tools to write down and copy and paste links on Product Hunt to different tools and they name them “free startup tools” or “design tools I love” or whatnot.

[00:38:31] SY: Yeah.

[00:38:32] RH: So we noticed this happening and we thought, “Well, we see this behavior. Why don’t we make it easy for them to create these lists themselves on Product Hunt in just a single click or a couple clicks?” And that has been successful in kind of building for behavior and now people create all kinds of collections and it’s used for not only storage of like remembering and bookmarking these things, but then it also allows us to segue that feature into a way to curate products.

[00:38:58] SY: Yeah. That makes sense. Was there ever a thing that you saw people do the you said, “No, that’s not what we’re doing here, that’s not what we’re building, that’s not where we want to go”?

[00:39:07] RH: I think one of the most common requests has always been around personalization and people often say, “Hey, why don’t you make the Product Hunt homepage entirely personalized?” and all these other things. And I think personalization is this common trap, actually within social products and consumer products in general is that either one, it will go against what you’re building and I’ll describe kind of why I think it doesn’t work for Product Hunt. But two, it oftentimes will have very marginal impact unless you’re a massive scale. The desire for personalization is a common one and the reason why I don’t think it’s right for Product Hunt, I mean, we do have aspects of personalization, but the reason why I don’t think we should change our homepage entirely to a personalized feed is that the whole purpose and where people get value out of Product Hunt is the watercooler effect and having this front page where people can say, “Hey, I’m number one on Product Hunt,” or, “Hey, did you see that thing on Product Hunt yesterday?” If we had entirely personalized feeds, we couldn’t have those conversations and it wouldn’t have the same watercooler effect that it has today.

[00:40:07] SY: Yeah. That makes a lot of sense. So Product Hunt is going well and you actually got accepted, you applied and got accepted into YC.

[00:40:16] RH: Yeah, that’s right.

[00:40:18] SY: How was that? Was that the moment when you thought like, “Okay, this is going to be big”?

[00:40:22] RH: We are maybe four or five months into past the email list when it first started and Y Combinator, the current batch, a lot of them were using Product Hunt themselves and they were launching.

[00:40:31] SY: Oh, nice.

[00:40:32] RH: What’s funny is I just spoke with Garry Tan, who used to be at YC a few days ago and we’re just reflecting on this. One of the founders of Algolia who was in YC at the time, he DMed me on Twitter and said, “Hey, Ryan, what are you doing with Product Hunt? Are you thinking about doing Y Combinator? Garry Tan would love to meet you.” So I met with Garry at The Grove here in San Francisco and chatted with him. This was right at the crossroads where it was, “What am I going to do with this thing? What’s the long-term plan? Do we build this into a business? If we do, do we raise capital, raise VC and go that route or do we find a different path?”

[00:41:07] SY: And at this point, you were still at PlayHaven?

[00:41:10] RH: This point I was not at PlayHaven anymore.

[00:41:12] SY: Okay. So you left at this point. Okay.

[00:41:13] RH: Yeah. Yeah I had left and I worked at PlayHaven part-time for a while, which allowed me to pay my rent basically. But yeah, I had left at that point, but I was still figuring out, and we were actually making I think it was around $4,000 a month which paid like our [INAUDIBLE 00:41:38] bill and things like that.

[00:41:31] SY: Yeah. So even in its side project phase, you’d left. And at that point, did you leave specifically to pursue Product Hunt or did you leave and thought, “Maybe Product Hunt will be the thing. Who knows”?

[00:41:42] RH: It was more the latter. I was thinking, “Maybe this will be it,” but I really want to be thoughtful, especially when it comes to raising capital and this was my conversation with Garry. The primary reason why I wanted to meet him was one, get his feedback and advice because he’s before that had started companies because it’s a one-way door. You can’t really give money back. I mean you can, but it’s really messy and I would not advise it.

[00:42:08] SY: Yeah.

[00:42:09] RH: And so I wanted to be assured that this was the right thing to pursue long-term. So I talked to Garry and there were some words that stuck out for me. He said, “Very infrequently do people catch lightning in a bottle,” like Product Hunt was at the time especially, and what he meant by that was, “We dabble and we build and we try to build a product that people use and love and most of it’s not going to work out, and in the moments where it does start to work and show signs of being something really meaningful, you got to really double down on that and really recognize that.” And so after that conversation, I met with Kat, I met with Kevin Hale, I met with Alexis Ohanian and then decided to apply to Y Combinator and ended up getting in in the summer 2014.

[00:42:51] SY: Wow! So you had some pretty big conversations with some pretty big people before you even decided.

[00:42:57] RH: Yeah. Yeah.

[00:42:57] SY: That’s awesome.

[00:42:58] RH: I mean part of it was they were trying to recruit Product Hunt is the reality. They wanted Product Hunt to be in and so speaking with them, but I still went through the whole process, did the video interview, did the in-person interview, did the whole application.

[00:43:11] SY: So you were part of YC in 2014. Now it is many years later, you have been acquired by AngelList. Over the past, what, four or five years, what has been the biggest product changes of Product Hunt?

[00:43:27] RH: Yeah. We built a lot of things. Some things have worked, a lot of them haven’t, which is expected I think with anything. I think a lot of what we’re noticing, a lot of what we’re shifting towards over the past, particularly the past year or so, is Product Hunt is known as really kind of a launch pad for new companies, new products, as a place to discover what’s new and what’s coming up, and that’s kind of what we’re known for, but what we’ve noticed is there’s a lot of desire within sort of the maker and technology community of people wanting to connect together and help each other and get feedback. I’m reflecting back on when Product Hunt first started, there was really no place for me to, one, even connect with other people that were outside my network to like get help whether it’s with design or engineering.

[00:44:14] SY: It’s true. Yeah.

[00:44:15] RH: And two, I fortunately had a small audience through blogging as I mentioned earlier, but most people don’t have enough people. They have just their friends and their friends might be fine beta testers, but at the end of the day your friends are probably going to be overly nice and say how awesome your product is and perhaps they’re not even the right users either. So reflecting on that, what we really are exploring more of and building on is how do we make Product Hunt more of a social network in a sense that this is a place for makers and people building technology and whether it’s a side project or any startup, a place to get help, share their goals, have social accountability, get feedback, get beta users and really connect with other like-minded people across the world that are also really into technology.

[00:45:01] SY: Yeah. And so when we think about a social network, what does that actually translate to? Is that a discussion forum? Is it a live chat? What are the features or actual products that come from that, at least for Product Hunt?

[00:45:19] RH: There’s a number of things. There are some very I would say relatively minor or tactical things and this goes back to what I said earlier about observing user behavior. What we noticed is oftentimes people in the Product Hunt comments when there’s a product being launched, there’ll be a conversation between maybe the maker and some other person and they’ll basically take the conversation offline, whether it’s, “Hey, I’ll help you with this. Oh, email me here,” or, “Hey, I have experience building in this space. DM me on Twitter and I’ll love to give you advice or feedback.” And so we noticed this behavior happening and obviously that’s kind of inefficient and people generally don’t want to share their email on a public forum like that either. So we introduced private messaging where you can just simply message another user on Product Hunt, which not the most innovative, crazy idea, but it’s very simply based on clearly there’s a need for this, clearly there’s a desire to communicate privately. And we also built some very native authentic ways of that. So if you see a comment on Product Hunt, you can actually click the message button which will basically include a snippet of that comment. So there’s context around why this person is messaging you.

[00:46:25] SY: Oh, nice! Yeah.

[00:46:27] RH: So there’s things like that that we kind of built in to allow for more of those connections and then a lot of what we’re building, actually the thing I’m super excited about that I haven’t talked about yet is we’re kind of building this platform for people to share their goals, whether it’s get a hundred beta users, share, redesign my website. What we’re seeing is people are organically kind of reaching out and saying, “Hey, I’m happy to read a draft of your blog post before it goes out,” or, “I would love to beta test your product.” So we’re doubling down on that with some really interesting… I don’t even know if this is the right messaging but kind of like virtual co-working is we want to build.

[00:47:04] SY: Yeah.

[00:47:06] RH: And ways to increase social accountability, help people share what they’re working on, and ultimately help people help each other.

[00:47:13] SY: Oh, I love that. That’s wonderful. So now you are still running Product Hunt, but you’re also an investor with Weekend Fund, which I understand is a $3 million fund for early-stage startups. So between doing Product Hunt, selling that, being a product guy for many, many years, what do you look for in other products and in people who are hoping to turn their products into businesses?

[00:47:38] RH: Yeah. So I’ve learned a lot in investing over the past, almost a year and a half now, and I’m focusing in very early stage. I spoke with a founder a couple days ago and someone I’ve known for a while. So I have a lot of trust and know their background, but they just started two weeks ago. They have no product and I committed to invest. So sometimes there’s very early stage companies like that. In other cases, they have a product out there and there’s some traction, but generally it’s pretty early. And when it’s early, you either don’t have data or you have such a limited data that’s really hard to evaluate by because retention numbers, that’s really what matters, like retention and the usage and it’s always going to be artificial in the beginning and you never really know how retentive a product is in the very first three, six months sometimes. So a lot of what I look for is combination of, I mean, there are certain things that every investor says like team and market and all of that and that’s true. My girlfriend’s also an investor and she has a saying like, “Clarity of Vision,” and I like that saying because when you speak with the founder and there is very clear vision of what they’re building, it’s very telling and actually the way that they communicate, I think communication is so important as a CEO or a founder is that it really informs how well they’re going to be able to fundraise, recruit, sell, all of these things. And if they’re able to have a strong perspective, that means a lot, a perspective of the future. And so there’s an example of one company that hasn’t launched yet that I committed to invest before they had a product. In fact, they didn’t even have a full pitch deck ready because he had such a strong vision of what he’s building for and is one of those conversations where I learned some things coming out of it.

[00:49:30] SY: That’s always good.

[00:49:31] RH: Yeah. In cases where I don’t necessarily learn something, it’s not because I think I know everything by any means, but when you can kind of predict the answers that they’re going to say or the direction that they’re going to head, then you’re like, “Well, if they’re thinking about this 24/7 and I thought about those same ideas, something’s off.”

[00:49:48] SY: That’s a good point. Yeah.

[00:49:51] RH: So those are some different lenses or criteria I kind of look for when I’m speaking to founders.

[00:49:56] SY: Yeah, that makes sense. So what advice do you have for folks listening who are hoping to build an awesome product one day or maybe get into product management themselves?

[00:50:04] RH: Honestly, I think my biggest piece of advice is just build, just tinker and experiment, like think about what would you want to build or what ideas do you have, and I think building is a great way to of course learn whether it’s learning how to be a better coder or different frameworks, how to design. I see it very similar to other forms of art, being a musician. Musicians, if you’re a drummer, you practice all the time and I feel building and just creating things is kind of like practice for being a founder or being a product manager or engineer or whatnot. And there’s a lot of I feel like pressure. People put pressure on themselves to build a startup and then name themselves founder and assume that they’re going to go raise money, but I think it’s fine just to build stuff too, like build stuff because you think it’s cool and interesting and that will go a long way. If you want to get into product management, I mentioned earlier it’s really hard to get a job if you don’t have product managing experience. The best thing next to that though is having side projects and basically being your own PM. You can have product management experience by building stuff on your own and showing in your resume or when you’re speaking with recruiters saying, “Hey, I built X, Y, Z and here’s my thought process and how I went about it.”

[00:51:19] SY: Yeah, make your own Trello board, write those user stories, you can do a lot of the same stuff, just do it for yourself.

[00:51:23] RH: Exactly.

[00:51:24] SY: Well, thank you so much Ryan for spending so much time with us and telling us a story of Product Hunt and product management. You want to say goodbye?

[00:51:30] RH: Thanks a lot for having me. Appreciate it.

[00:51:32] SY: And that’s the end of the episode. Let me know what you think. Tweet me at CodeNewbies or send me an email, hello@codenewbie.org. For more info on the podcast, check out www.codenewbie.org/podcast and join us for our weekly Twitter chats. We’ve got our Wednesday chats at 9 P.M. Eastern Time and our weekly coding check-in every Sunday at 2 P.M. Eastern Time. Thanks for listening. See you next week.

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