Ryan Hoover on Experiments, Launches and the Mask Every Founder Wears

Hoover says he has moved to Miami, where he and his girlfriend spend about two-thirds of the year, and he had not talked about it publicly to avoid being lumped in with everyone else moving there. His framing is that cities are like products. Each has costs, such as housing, food and taxes, and benefits, and after ten years in the Bay Area and two in Los Angeles he judged Miami a strong return on investment because it was cheaper and many friends had moved there.

Lenny asks about Hoover's habit of inviting founders to DM him questions and sharing some answers on Twitter. Hoover had kept his DMs closed for years, expecting spam, and found it was not bad when he opened them. He started the practice partly to kill time on a bike and partly because he writes less than he used to. A question from someone else works as a prompt, and answering it helps him refine his own thinking, like a micro blog post.

What surprised him most was how candid strangers are. Founders write in to say they have three months of runway left and ask what to do, which people would never post in a public AMA. Hoover describes the mask everyone in business wears, where everything is going great, and says that peering inside almost any company would reveal some kind of chaos. The authenticity of these questions is what he values most about the exercise.

Asked whether people should start companies, Hoover says he sometimes spends time challenging founders who assume the first step after having an idea is to raise money. Product Hunt began as a newsletter, then a website, and it was four or five months before the team incorporated. During that time he asked himself whether he wanted to work on it for many years and whether it was venture-backable, even as investors courted him in the bullish market of late 2013 and early 2014.

His rule of thumb is a decade: can you see yourself working on this for ten years? He does not expect that to happen, since most startups fail first, but he sees it as a litmus test of whether you care enough. He also encourages tinkering before committing, and the team called Product Hunt an experiment because the goal of an experiment is to learn, not to succeed. That is also part of the reason he named his fund Weekend Fund, alongside the fact that he took founder calls on weekends and that many great ideas begin as nights-and-weekends projects.

On whether he would raise money for Product Hunt again, he says the question to ask is what the money is for. He needed it to hire and had no personal capital, and he judges that open-sourcing the product was not realistic. Today he might get a year of development funded himself, and since Product Hunt lacks Uber-and-Lyft style competitors that force a war chest, he might not raise venture capital. He also stresses raising from people whose expectations align with yours, because a founder or CEO, unlike an employee, cannot simply give notice and leave.

Hoover says whether launching is worth it depends on the goal, just as with raising money. Many founders default to customer acquisition, which a launch does not always help with, but there are other reasons: recruiting, creating momentum for fundraising, gathering feedback, finding partnerships and boosting SEO. He also points to team morale, an overlooked benefit, as long as teams do not launch only to chase likes and upvotes. Even a team member sharing an article with their mother matters more than it seems.

Having seen tens of thousands of launches, he says the most common mistake is writing like a PR person. He suggests writing your tagline the way customers describe the product to others, or the way you would explain it to a friend. Buzzwords and vague language do not click, and he adds that more attention should go to the product and to understanding who you are building for and what the value proposition is in the user's mind.

For tactical guidance, Hoover points to the guides and checklists linked on Product Hunt. He recommends keeping the maker's introduction short, since people browsing the site are looking for things that spark curiosity and not essays. He also notes that the gallery is often the first thing visitors see, and the best ones use it like a slideshow that tells a story, such as a before-and-after. Asked what reaches the top, he says it varies: seemingly boring B2B tools can win, silly apps can too, and results often follow the zeitgeist of the early-adopter tech community.

Asked what a product management background brings to investing, Hoover says all early-stage risks ultimately come down to the product. A product background helps him judge how a founder thinks and arrives at insights, more than just assessing market need, and he enjoys jamming on product with founders early on. Lenny adds that PMs have many of the skills a founder needs, and Hoover says the same goes for investors.

His first regret is trying to expand Product Hunt beyond tech. The team experimented with podcasts, video games and books, but he underestimated how different the product experience would need to be and how hard it is to carry a community into new ones; he cites Reddit as a rare exception. His second is that the company raised a seed and a Series A without trying to make money until after the AngelList acquisition. He thinks about 10% of focus on revenue would have brought break-even by 2015 or 2016, since revenue, once started, reached cash-flow break-even in roughly a year.

The third is delegation. Hoover calls himself a controlling person with strong opinions and says that, until shortly before he left, he edited the Product Hunt newsletter every morning at 5 or 5:30 a.m. The team was excellent, he says, and the issue was his own trust. Lenny relates to the urge to make everything perfect, and Hoover agrees that this caring is useful but does not scale, and that more mistakes through delegation are net positive.

Asked for his most painful but valuable lesson, Hoover says he recently wrote a blog post he cannot publish because it could complicate things for others. Speaking generally, he describes hard times at Product Hunt when he felt physically ill and woke up with anxiety in his stomach. Being CEO makes it harder because you must show confidence to be trusted and cannot be fully transparent without passing your anxiety on to others. He values authenticity, so that tension is a struggle.

He says the experience built empathy for founders in tough situations and made him a bit thicker-skinned, adding that what did not break him only scarred him a little. On what matters most, he says he is still working out the meaning of life. Friends and authentic relationships matter more to him with age, and he now prefers a few deep relationships to a large network.

In business, he says momentum matters enormously because it is reflexive: high momentum breeds more of it, as people see others shipping and want to join in, and low momentum drags others down. Lenny links this to Marc Andreessen's point that a company is either gaining or losing gravity. Hoover ties it to the power law in investing, where one company in a portfolio of a hundred can return as much as all the others combined.

In a rapid-fire round, Hoover picks TikTok over Reels and Los Angeles over the Bay Area today, though he says San Francisco was right ten years ago for serendipity. His hot take is that a founder who prioritizes dark mode before product-market fit is a red flag for him. He adds that it depends on the audience and that developers may expect it.

On why most consumer startups fail, he says consumer social and gaming are the hardest. Monetization is tougher than in B2B, where customers pay from day one, and advertising requires massive scale first. Consumer products also compete for attention with everything from Netflix to entrenched habits. He explains that the goal is to become an internal trigger in the user's mind, while you usually start with external triggers, and he notes that consumer problems are fuzzier than something like DocuSign's clear job.

He argues you need some unique insight to build a consumer company. One source is a problem journal, in which he writes down annoyances without trying to solve them, like the lack of laundry in many San Francisco units. Others are immersing yourself in niche communities, watching consumer behavior shifts such as distributed work, and watching technology shifts like mobile. He adds that because more people are building, you need strong answers to why now and why this does not already exist.

Lenny raises the counterintuitive advice to focus on a very small audience first. Hoover says that, with the caveat that context always matters, a narrower audience makes it easier to build a great solution because the product, the messaging and the homepage can speak to one specific problem. It helps both product and go-to-market.

His bias is not to worry that a niche is too small, because over time you tend to find parallels with other communities and problems. He uses Airbnb as the example: it began with couches and spare rooms, which most people in the US, including his parents and himself, would not have considered, yet it grew well beyond that. In his mind Airbnb is now essentially about housing in general.

On what he has learned running Weekend Fund, Hoover first mentions operational hygiene: replying to founders even with a pass, and giving enough context to be useful, and always closing the loop with the person who made the introduction. His biggest surprise is that companies he had mentally written off later pivoted or landed a big partnership, so he says never count a portfolio company out until it is over. The fund has invested in over 110 companies.

He says the fund looks at team, market and product holistically, since the product reflects the team's thinking and it is hard to evaluate founders directly unless you know them well. He does make pure founder bets occasionally, such as a talented builder he had waited years for who might launch ten apps before the eleventh succeeds. Lenny says he only makes founder bets on people he knows.

For aspiring investors, Hoover lays out the options: angel investing, which needs disposable income and a willingness to lose it all; scouting; SPVs, which give deal-by-deal carry but take a lot of work; and raising a fund, which he did in 2017. If none is feasible, he suggests pretend investing by writing memos on companies you would back, as his colleague Vedika did before joining. Weekend Fund is on its third fund, about 30 to 35 percent deployed and 21 million dollars in size, which may be the largest he ever raises since it keeps the fund collaborative and lets it write smaller checks.

Looking ahead, he says he will always invest but loves building and wants to find the right idea. He is interested in owning something fully and delaying venture capital, which he calls a one-way door. He says he can be found as Rhoover on Twitter and at ryanhoover.me.