Most of the people we’ve interviewed for this series have been seasoned entrepreneurs with great business successes behind them, either large, profitable businesses or enviable exits.
Ryan Hoover is a bit different.
At just 29, Ryan’s best successes are undoubtedly ahead of him.
Ryan is very much still in the weeds. Although his company, Product Hunt, has many hundreds of thousands of users (400,000 in October, and “much, much more than that” today), the company has a lot of work to do in building a sustainable—and profitable—business.
But he and his team have accomplished a lot in the last couple of years.
We talked to Ryan about how he prepared himself to be an entrepreneur, left his job to take a chance on a side project, and ended up building one of the most popular sites in tech.
How Product Hunt Went From a Side Project to One of the Hottest Sites in Tech
An Early Start
Ryan isn’t the first entrepreneur in his family.
His dad has been hustling since Ryan was born…
When he was an adult in the late 80’s or 90’s, he used to sell video games out of the back of his car. This was back when video games were not in WalMarts everywhere, and of course you couldn’t just download them online yet.
Games just weren’t that easy to get, and so eventually he opened a video game store in Eugene, Oregon. That was just one of the many different businesses that he ran over the years, and I think a lot of my entrepreneurial passions come from him giving me opportunities to do entrepreneurial things at an early age.
In his early teens, Ryan was already allowed to do some managerial work.
When I was 11 or 12, it was my responsibility to manage the gumball machines, which didn’t mean I would do a whole lot of work, but as a very young kid I had to buy more gumballs, Runts, Reese’s M&M’s, that sort of thing. I’d fill them up and make sure they were stocked.
I’d collect all of the coins and quarters.
As a kid, holding a giant bag of quarters was meaningful. Share on XIt was heavy, and maybe it was only $5 or so, but it felt like a lot of money.
I’d collect the money and then I used my grandpa’s old Apple computer to record revenues and expenses in a spreadsheet.
That was cool as a kid, because I learned “oh, I can do this thing that can turn into actual money.” That’s how capitalism works in some ways and it doesn’t have to be through a traditional job where you get paid hourly.
It wasn’t long before Ryan found other entrepreneurial inspirations…
I also started selling these game walkthrough handbooks.
I’d go to gamefaqs.com—at the time, it was the best resource to get walkthroughs—and I would print them out and put them in these little handmade books and then sell walkthroughs to the new Zelda game, or to Goldeneye or whatever. My dad always encouraged me to get creative with ideas like this as a pre-teen.
And while Ryan’s dad’s businesses have little in common with a platform like Product Hunt, Ryan says he still took away valuable lessons from working in more traditional ventures:
I think a lot of the fundamentals of entrepreneurs are true in both [brick-and-mortar and software companies].
For example, my dad has always said “find a hole and fill it.”
What he means by that is that you should find a need that someone has, and fulfill that need.
You have to create something that has value for people, whether we’re building a product, or a community, or a store for video game enthusiasts to buy, trade and sell their games. It’s a simple statement but sometimes overlooked by product or company builders.
Entering the Workforce
Despite Ryan’s entrepreneurial teenage years, he opted for a more traditional route out of college, when we took a job with InstantAction, a video game startup in Eugene where he interned as a student.
There, Ryan worked for about a year before things began to get choppy…
Unfortunately, we got to a situation where everyone was jumping ship, and it was pretty clear that it needed a miracle to survive long term.
And that’s when a note from a former executive, Andy Yang (now CEO of Upsight), changed Ryan’s course forever.
Like a lot of others, I was casually looking for companies that I might want to join. I wanted to stay in technology and work in a startup, and San Francisco was a magnet for me.
Andy had left InstantAction shortly after I joined and ended up moving to San Francisco to join Playhaven. He dropped a hint that he was looking for a product manager, and that planted a seed in my head.
I told him that it sounded exciting. I liked what they were doing, and I really wanted to live in San Francisco, so I began to talk to him about it and ended up flying out to interview with the rest of the team and eventually getting the job.
Learning the Skills That Would Shape Product Hunt
It was at Playhaven that Ryan truly began to hone his product manager chops.
I joined Playhaven as employee number ten; the first product manager.
We went through a lot of changes, and a lot of startup challenges.
Every startup goes through a lot of unknowns, and when I joined we had this product that was sort of working, but it wasn’t heading in a direction that we believed would be super meaningful, so we went through a bunch of changes and eventually did a slight pivot.
It ended up working, and we grew from ten people about 100 or so when I left. In my 3.5 years there, I was working with anything and everything related to the product.
I worked with the team to improve the product, met with customers (big and small game developers), communicated roadmap internally across the team, and everything in between.
When asked whether he thought his background as a product manager makes him a better CEO, Ryan didn’t hesitate:
Absolutely. I feel like product manager is one of the best roles to get into if you want to eventually become a CEO, in part because your job is very diverse.
It’s talking to a lot of people—from internal teammates, designers, marketers, salespeople and the CEO to external people like customers or clients—and as the CEO your job is to communicate to everyone. That overlap has been really helpful.
I’m sure I have a bias, but I also feel that more product-oriented CEO’s are better suited for some companies. It depends on what you’re building, but for many the product is the thing that has to work. If it doesn’t, you’re in trouble, and if you’re the leader of the company and you don’t have the skill set to understand that and know how to guide the team on what to build, then I don’t see how it could work.
Obviously a lot of people still become great CEO’s or founders without that, and a lot of people have product management experience without the product manager title. You might be an engineer, but you still might be filling a product management role. But I do think that those skills that you build in product management tasks are really helpful.
Deciding It Was Time to Move On
After three years at Playhaven, Ryan was no longer as excited about his work as he had been when he started.
I really like what we were doing, but I just started to lose passion for it, in part because we were building a tool set for mobile game developers and that wasn’t me, I wasn’t a game developer.
While I respect, appreciate and like games, it’s something I couldn’t wake up in the morning and get super excited about after 3 years.
The other thing is that we had grown a lot by then, and I wanted to move to something smaller again where I could learn and grow more, so I thought, “ok it’s been three years, I think it’s time for me to move on and do something different.”
I told my team and my boss that I was moving on, and that I didn’t know where I was going to go, but that I’d give them two months notice, which would give me some time to transition and find something new.
Well, that two months actually turned into me transitioning to helping the company part-time for almost six months, which was incredible. I still got to make some money and not worry too much, and I had the time to find the right startup to join and work on various projects.
The Earliest Seeds of Product Hunt
Product Hunt, like many popular products, didn’t start with grand dreams.
Instead, it was a side project that Ryan initially didn’t intend to become a business.
It started as just a simple email list in November 2013. Share on XI thought, “how can me and my friends find cool products and share them with each other? Why not have a place for us to do that?”
And so the idea was pretty simple, and the easiest way to build something like that was an email list rather than a site. I wasn’t an engineer, so I wasn’t going to invest the time or money in building an entire site from the start, but I could build an email list really easily.o I started one and invited a few dozen investors, founders, and other friends of mine who I thought might like this, and who had an inside track of what kind of tech products were cool.
The way it worked was they could submit new things they found to this email list, which would then get distributed to anyone that subscribed to the list. It would go out each day automatically using a service called LinkyDink.
Once it was up, I shared it on Twitter and Quibb, which was this network of entrepreneurs and startup people sharing and discussing articles.
From those efforts, I got a few hundred subscribers on the email list pretty quickly, which wasn’t mind-blowing but it was enough to say “ok people are going to read this, that’s cool.”
In the next two weeks or so I just kept working, people kept submitting stuff and it started to get some traction.
More and more people were subscribing, and then a few different people emailed me, or I’d see some people in person and they’d tell me, “hey that product hunt email is cool, I look forward to it every day.”
That’s when the spark hit me.
I thought, “hey, I like this thing too, it’s a lot of fun and useful. Maybe it could turn it into something even more meaningful.”
Since it was just an email list, it lacked a lot of functionality.
I had some time since I was only working part-time while looking for other opportunities, and I reached out to a few people.
One of them was my friend Nathan Bashaw, and I told him that my idea was to take this email list and turn it into a community where people could submit on the website and then comment on it, sort of like reddit or Hacker News.
It wasn’t anything new per se, people understood the model, I just wanted to apply it to this new type of community.
I planned on learning to build it myself, so I asked Nathan how he would recommend I go about doing that. And he offered to help, excited to work on it while visiting his parents over Thanksgiving break.
So over a five day period, he and I collaborated over the phone and online, and when we were done we had this really basic version of Product Hunt.
A Period Of Rapid Growth
To say that Product Hunt grew quickly would be an understatement.
20 days after launch, the company had 2,000 active users.
Ryan shared some of the tactics he used to get those initial users in a Fast Company article, including, of course, plenty of one-by-one outreach.
The strategy worked, and it worked fast.
It wasn’t long before Product Hunt became a magnet for tech press – starting with Carmel DeAmicis’s article on PandoDaily, which Ryan scored after having written guest articles for the publication months prior.
Makers of all types were participating on the site, from teenage developers in Europe to well-known founders and CEO’s.
A lot of people in our community were saying “hey it was really cool when Mikey, co-founder of Instagram, came in chatting in the comments about the new Instagram update” and at one point people just started asking questions in the comments, and it seemed like this really positive authentic discussion.
So we thought we could make an actual feature out of it, with a schedule of really cool people coming up and doing live discussions.
And so we got to work building up this schedule of a bunch of different people from different industries, from technology to entertainment to books to podcasts to gaming and all over.
Product Hunt has since hosted LIVE Chats with B.J. Novak, Jessica Livingston, Jack Dorsey, and over 200 others.
But, Ryan says, “it didn’t happen overnight.”
For a year, a year and half, we were just building relationships with great people. It took a lot of work, and slowly people began seeing other people that they know on Product Hunt, then they would think “ok, this is a community I’d like to participate in”, so over time it gets easier and easier to get more people in. Jack Dorsey, for example, agreed to join us after sending him a tweet because of the reputation we’ve built.
But it didn’t happen overnight.
Ryan’s Biggest Challenge as CEO of a Growing Company
Like any rapidly scaling business, Product Hunt’s growth hasn’t come without challenges.
But, Ryan says, the hardest part of being CEO has nothing to do with his users.
The hardest part is that when you’re 3, 4, 5, 6 people, it’s almost impossible not to know what everyone’s doing. Plus, I tend to keep a lot of it in my head, and I might know everything that’s in my head, but everyone else doesn’t. And when I talk to people and I explain what’s in my head, I only talk to 1, 2 or 3 people out of the entire team, and so what I realized is that I need to communicate clearly and repeat things I’ve discussed with only a subset of the team.
It’s so, so important to be a good communicator, and to not just communicate what you’re doing to the team, but why you’re doing it.
That last part, according to Ryan, is critical.
I’m naturally skeptical about a lot of things, so I always approach things with why is it like that, or why make that decision, because ultimately I want to find the best marketing message or the best product decision, and if someone comes in and says we’re doing this, but I don’t know the background or thought process behind the why of that decision, I remain skeptical.
People do need to understand why we’re doing what we’re doing, and once they understand the why and the trade-offs, then people are more bought in. They understand that we’re doing something because there’s a good reason to do it and not just because Ryan says so.
Going Back to “School”
In the summer of 2014, about six months after launching, Product Hunt joined Y Combinator.
There typically wouldn’t be anything unusual about that; except that Product Hunt was already hot. They had a growing user base and impressive name recognition; a contrast to the very early-stage startups that YC often attracts.
And in fact, Product Hunt joined YC because the YC team had heard about Product Hunt and reached out to Ryan.
The value that the team got from the accelerator, Ryan says, was huge.
It had a lot of value in so many different ways.
Just being in the program, you’re surrounded by incredibly talented people who are all hustling over ten weeks to grow a business. It’s incredibly motivating.
YC partners are very experienced and succinct in their feedback, and I mean that in the best way possible. When they do office hours—and these office hours are twenty minutes max—you come out with new perspectives, and Kevin Hale and Qasar Younis were my group partners and they were just really good at questioning things. Alexis Ohanian, co-founder of reddit, was also very helpful in guiding us through YC.
Having that boot camp process was just incredibly helpful to our company as an accelerant.
And then there’s also the YC network itself; once you finish YC, it’s still accessible. There’s still the alumni,office hours, and YC has been fantastic when it comes to the brand recognition that being a YC company brings, especially in the field we’re in.
Looking Ahead
There’s no question that the business is a promising one, and that Ryan and his team have a massive opportunity ahead of them.
And with several million dollars raised, they have the opportunity to think about getting as many users as possible without worrying too much about cash… yet.
It’s something that we’re definitely thinking about, and we’ve done a lot of exercises in thinking more thoroughly about different opportunities. With that said, we’re not focusing on it right now.
It just comes down to trade off; if we focused on generating revenue—which we could do today—is that more important than building new features that might grow our audience?
So in the end, we’ve consciously made the decision to not focus on revenue right now. We’re lucky to have investors that are very supportive of our decision to do that.
Ryan’s Required Reading
As with every $100K interview, we asked Ryan for his required reading for all entrepreneurs.
One particular blog I’m going to have to recommend is Nir And Far.
I’ve known Nir for about three and half years, and he’s become a friend. I also worked on his book with him.
The blog makes some really powerful but hard-to-understand stuff easy to apply to building products and technology. It’s just really fascinating to read, and for anyone building a product, there’s a lot you can learn from what he’s writing about. It’s one of the best product oriented blogs out there.
Your Turn: Ask Ryan Anything
Ryan has (very) generously agreed to answer your questions in the comments of this interview.
We’re going to be watching closely and trying to learn as much as we can ourselves, so don’t be shy.
Post your questions for Ryan in the comments below.