Ryan Hoover always had a natural curiosity about what’s around the corner. When he started Product Hunt in November of 2013, he didn’t have a specific goal for the endeavor besides creating a “place to discover your next favorite thing.” Now, four years after stepping down as the CEO of Product Hunt, he’s focused on Weekend Fund, the early-stage fund he founded in 2017. His work is still centered on finding "your next favorite thing" — he's just focused on backing it this time.

Both his work at Product Hunt and at Weekend Fund highlight a trend in Hoover’s life at large: he doesn’t make a lot of die-hard bets about what lies ahead. His fascination with “the next thing” is less about a desire to call it correctly, and more about a genuine inquisitiveness about where tech, culture, or society could be headed. He just leans into what naturally sparks his curiosity — and things have generally seemed to fall into place from there.

“Every big career shift came organically, almost by accident,” Hoover says, thinking back.

It’s not a totally uncommon story — plenty of founders and entrepreneurs will tell you that you can roadmap and forecast your way to a point, but success is often a perfect combination of preparation and luck. But for Hoover, whose life and career have seemed to largely follow this pattern of happening organically, luck seems especially on his side.

The reality is that this is less a testament to Hoover’s stars sitting in a constant state of alignment and more to his philosophy on luck in the first place: that when you can silence the noise and lean into your curiosity, you just might increase your odds of getting lucky.

At one point in our conversation, Ryan will tell me he’s an introvert — but you wouldn’t know it immediately from our call. He has a natural ease as he hops into our Zoom chat, immediately following his “hello” with a question about what my necklace says (my name in Arabic) and grabbing a La Croix for himself before joking that he’d offer me one if he could, “but we haven’t invented the technology for that yet.”

If the technology did exist, it might be something that Ryan and his team at Weekend Fund would consider investing in. “Years ago, we did invest in a company that was doing drone delivery of food on college campuses,” he remembers. “Then Covid happened. So there’s that.”

We’re still in the pre-interview small talk portion of our call, and already, Hoover has shed light on one of those undeniable realities of startups: a company’s trajectory is largely at the mercy of environmental factors that founders and investors don’t always control. One minute, you’re onto something great. The next, a curveball throws a wrench in your plans. That’s the luck factor at work, for better or worse.

In Hoover’s case, it was more better than worse. As a first-time founder, he didn’t have to deal so much with bad luck stopping him in his tracks. He put in the work, and good fortune seemed to be the wind in his sails.

Product Hunt’s story is one of humble beginnings. It began as a side project that Hoover created while working part-time on product for PlayHaven, a mobile game development platform. At the time, he’d been interested in creating a place for himself and other product enthusiasts to share cool products with one another. Without the engineering know-how to build a site, an email list seemed like the best alternative.

So, on the morning of November 6, 2013, Hoover put the list together on Linkydink in about 30 minutes, invited some friends to collaborate, and officially launched his “email-first experiment” with a tweet and well-received post on the now-defunct social network Quibb.

“Instantly, it got a little bit of traction,” Hoover recalls. “I didn’t have a big audience [on Twitter], but it was just enough to where people would listen. If I’d had zero followers, it would have been impossible. I had just enough to seed the community and build the initial user base.”

The next six years saw a number of changes at Product Hunt, including the company being acquired for a reported $20M by AngelList in 2016 and Hoover eventually stepping down as CEO in October 2020.

“When you build a company, it’s kind of a series of inflection points,” says Hoover. “There’s certain things that work and then they stop working, and we were constantly going through these iterative cycles. We tried a few big swings, and [some of them] got some traction but nothing big enough to really double down on. That’s the nature of building in startups — you work really hard and sometimes the thing doesn’t work. But after seven years, it got a little draining. When we started, I was just having so much fun and [by the end,] I had started waking up not feeling as energized as I used to.”

It was at this point in time — as Hoover began feeling an incongruence between the work he was doing and the work that would excite him — that his curiosity began looking outward at what might be next.

Prior to starting Weekend Fund — and even prior to Product Hunt — Hoover had been curious about investing. “At the time, I [had been] exploring what the next thing [after PlayHaven] would be. I applied to two different startups, and didn’t get the job at either one. I’d always wanted to start investing so I was considering getting into venture. But realistically I would have been an associate at a firm. There’s nothing wrong with that, but I’m an introvert and didn’t want to be doing eight back-to-back coffee meetings. I wanted to do it my own way and in a way I would have energy for, so I realized venture wasn’t a path for me at the time.”

So he tabled the idea of investing, which worked out fine as he went on to start Product Hunt instead. He came into his own as an operator, but the itch to invest stuck. Still, there were a couple of things that kept Hoover out of the game: 1) he didn’t have personal capital to invest at the time, and 2) there was a bit of a stigma around investing as a venture-backed, non-acquired company. “A lot of investors want a founder to only be doing their startup. And there’s some legitimacy to that, but especially back then, it wasn’t normal for a CEO to raise a fund and start investing outside of their day-to-day nine-to-five.”

The shift came with Product Hunt’s acquisition by AngelList in 2017. At AngelList, there was a large focus around encouraging teammates and employees to invest and build up experience in that realm, and it was something Hoover could suddenly do with relative ease — so he decided to give it a shot.

“The next big thing is being built on nights and weekends,” Hoover wrote in a September 2017 post on Medium, announcing the launch of the aptly named Weekend Fund with an observation inspired by a16z partner Chris Dixon. He shared that he’d be dedicating some of his attention to this new endeavor while keeping his main focus on Product Hunt. “Some of the most transformational companies [e.g., Facebook, Imgur, Craigslist] started as a side project driven by curiosity and an eagerness to build something new.”

Using AngelList’s Angel Fund platform as a launchpad, he started his first fund with a $1M target. “It was the smallest fund of all time. It did grow to $3M, but even that’s still comically small.” (Weekend Fund’s second fund in 2019 was less comically small at $10M. The third, at $21M, was their largest to date, but still intentionally small despite demand.)

As Hoover began deploying capital to back early-stage ventures, he found himself reconnecting with that spark and natural curiosity that he’d felt in Product Hunt’s early days.

“At that point, it had been four years of me waking up every morning and seeing what was new on the site,” he says, noting that it felt natural to start spotting intriguing new products and technology with an investor lens.

“The implicit meaning behind ‘next favorite thing’ is something of progress, something of curiosity, something that’s optimistic. And I prefer to be among optimists,” Hoover says, breaking his investing philosophy down to its core tenets. “There is a very pessimistic narrative that we started to see in tech since like 2016, in which a lot of people are just so negative. And it’s easy to be that way because a majority of new tech startups do fail, and people feel smart about it. They like feeling like they called it right. But at the end of the day, builders and creators — the people who are curious to try to turn an idea into something real — are the ones making progress and solving problems.

At the same time, we don’t really know what’s next. We have ideas of what the future looks like, or we have areas of interest, but it’s up to founders to be the ones to create that. So for us [at Weekend Fund], it’s more about being curious enough to understand the shifts that founders are building upon and have a thesis about what it means for the future. These could be technology shifts, cultural shifts, regulatory shifts. We try to meet founders that have an insight into these inflection points and can articulate why the thing they’re building doesn’t exist already.”

There are plenty of companies in Weekend Fund’s portfolio  — Deel, Justpoint, Mindbloom, just to name a few — that align nicely with these “viable theses for the future,” as Hoover calls them. In this way, Hoover’s investing captures this spirit of curiosity that has been a constant in his life and career, but starts bringing that curiosity into stronger alignment by leaning into well-informed hunches about what the world might look like at some point down the road.

Hoover’s story isn’t one about the virtues of blind faith — that kind of thinking won’t get you too far, especially in startups.

There’s an element of serendipity that shows up time and time again, yes. But the more Hoover reflects on it now, the more he realizes that it was his curiosity that helped him create or spot serendipity at different points in his life and career. It propelled him to maneuver in a way that increased his chances of getting lucky, without overthinking the outcome or trying to be too logical.

Tinkering, Hoover says, is what he might consider the third on this list of actions or habits that have created more opportunities for serendipity in his life. By this, he just means taking the time to play with technology and explore it with the intention of learning and satisfying — or perhaps fueling — your curiosity. In doing so, you increase the chances that you’ll come across something that sparks a new idea or inspires your next step.

“If you’re in a creative field like music, for example, maybe you’re playing with production tools or making music yourself in some way,” he says. “If you’re an engineer, I think you have to be playing with LLM. For me, as a product manager, I always saw my job as to see what people were making and learn from that. I would download the top apps and look at their onboarding flows and see if there were particular patterns. I would change my app store to the Japanese app store and download Japanese apps to see how they’re different. And it’s not like I could read the text, but I was just trying to see how it was designed. This was actually part of the inspiration for Product Hunt. I started to think, ‘Why don’t we have a list somewhere of all the coolest products and apps so we can learn from them?’”

At any point in Hoover’s life, curiosity has been a compass. From his days as a product manager in the gaming industry to his time as an operator, to his current role as an investor, his best decisions were made when he tuned into his most basic desire to understand why things worked the way that they did, and what it might mean for how things will work in the future. The series of events in his life has always been a product of acting on intuitive hypotheses without trying to overthink or control what’s around the corner.

“When you live a curious life, you uncover secrets that you may not even realize are helpful at first, either because it seems inconsequential in the moment, or it just feels so natural to you, but not to other people,” Hoover says. “Again, with Product Hunt, I didn't think there was a secret to what we were doing until months in, when it became clear that we’d uncovered something. I think there’s just a lot of over-intellectualization of ideas where you sit at a whiteboard, and you try to think of a startup idea. You can build a company that way, but it's tough. Sometimes it's better just having it be more organic by leaning into what you’re curious about, and what feels fun to you.”

As he continues to reflect on his career to date, Hoover says that his goal is to continue leading with curiosity, but he wants to tap more into his intuition along the way. It’s something that has gone hand in hand with his curiosity at times — when he felt a misalignment and decided to move on from Product Hunt, when he packed up his life and headed to San Francisco.

But to put your curiosity into practice requires more than intentionality — it calls for action and, more often than not, courage.

“Nothing is accomplished in the head alone,” Hoover says. “There’s wisdom to gut or intuition, whatever you want to call it. This year, I’m trying to lean into it more. Most CEOs are more logical and in their head. But sometimes you just have to listen to your heart. And it’s tough, because there are moments when things are hard and you might misinterpret that as your gut telling you to do something else, but that’s not exactly it. What it’s really telling you is that you’re tired and it’s hard, that’s all. But I think it’s about listening to the recurring messages. When you ignore the recurring messages for a long time, and then you finally make a decision, you usually look at that in hindsight and it feels so obvious that your intuition was telling you that all along.”

In practice, Hoover says achieving this alignment between your curiosity and your intuition comes down to reflection — turning your curiosity to not just the world around you, but inwards. Be inquisitive enough to investigate your feelings as they emerge, and take the time to unpack their underlying drivers. Think about what gives you energy and what takes it away, then focus on doing more of what energizes you.

In the end, these are the habits that will stack the odds in your favor.