Ryan Hoover is the founder of Product Hunt. After its acquisition, he then went on to founding Weekend fund, were he now spends time in funding & assisting other early-stage startups.
He’s the editor of the book Hooked. And in this chat, Lenny & Ryan distill on how important launches are for new products, and how they can make the most in the critical stages that come in a product development journey.
Find the episode transcript and Ryan’s references here.
On being a tech celebrity ▶️
- One memorable moment was when he was at a dance party when someone recognized him as the "Product Hunt guy.", which made him realize he is on the public stage and his public actions matter.
- Fame and popularity can be socially exhausting, particularly for those who identify as introverts. “So by hour, like three or four, I'm just like, ugh… uh… I need to use the restroom cause I haven't been able to escape and I'm socially exhausted."
- How do you pick a city to live? Use ROI (Return on Investment) framework to figure this out, ie if the city offers a good 'product' value (healthcare, community, things that matter to you), leading to decisions like, "We're like, this is good., strong ROI. Uh, this is a good product. Let’s- let's move there."
Using Twitter DM's as a content machine ▶️
- Ryan opened up his DM to think about what founders ask him and the DM makes founders more vulnerable. This was also a hack for him to kickstart the day, and it just started with one simple tweet test, and he continues to enjoy it, despite the spam issue on Twitter, he was surprised with the quality of DMs.
- Leverage crowd-sourced questions as prompts: "I found this also kind of as a means to like, do micro- almost like micro blog posts in a way, uh, where the prompt is the question from somebody else."
- Reshare but keeping privacy in mind: "Well, maybe other people have similar questions, and maybe other people have other answers and other ideas too. I would just take a screenshot of my answer and kind of summarize their answer, of course, keeping it anonymous, not sharing anything that would be sensitive."
When should you start a company? ▶️
- Don’t take the decision lightly: "Don't start a company, unless you just like, can't not start a company because it's so hard."
- Funding isn’t always the first step. “I spend time, ironically, like. challenging founders sometimes when they're thinking about raising or thinking about an idea to- to not raise.” Instead of jumping into fund raising, spend time refining the idea, understanding its viability, and seeing how it gains traction.
- Commit long term: Do you see yourself working on this for a decade? This is a litmus test for founders to measure their dedication and enthusiasm for their venture, which weekend.fund looks for.
- The experimental mindset: “It's an experiment is really not about success. Of course you want it to be successful, but the goal is not success… it's really to learn and, you know, see if people want this thing and then kind of adapt.”
Would Ryan raise money for Product Hunt if he could do it again? ▶️
- Ryan considered making Product Hunt into an open-source project. However, he dismissed it, noting that "when you're building a company, you probably don't want to innovate on too many things, including like essentially how to build a product and build a team." Ryan needed the money to pay his team so he went after VC. With his wealth now, he would bootstrap it for a year instead.
- Raise funds from those "who are aligned with you. When you raise a series A, B, C, like you have different expectations and when you raise your preseed or seed round, so have guardians who can guide you in this process.
When should companies launch products? ▶️
- Launching a product isn't always about acquiring customers. It might be for recruitment, fundraising, feedback, or partnerships. The priorities of the business should determine the reason for a launch.
- "Why are you launching? And a lot of people default to things like customer acquisition, but sometimes that's actually not- it's not useful. Launch sometimes doesn't help with that, but there are many other reasons why you might wanna launch."
- Boosting team morale is a valid lanch reason "One of them is team morale. And this- this might- I think this is overlooked. But there is a gr- like a powerful team morale and kinda building moment there where you can all celebrate what you've accomplished and what you built and put it out to the world."
- SEO Benefits: If SEO is a part of the company's strategy, having positive articles and a successful launch can be super beneficial.
What makes a launch successful versus not? ▶️
- Speak like Human, not a PR machine. The language you use to communicate about your product matters. "One thing I've noticed among founders and just people in general is they tend to write like a- a PR person and not like a human. And the people that use buzzwords and- and vague language, it just doesn't click. People see right- people are sick of the PR speech." In line, knowing who you're building for and make sure your messaging aligns with your target audience's needs and desires.
- Copywriting and Micro copy really matter. Every little piece of text associated with your product can contribute to its overall perception, so invest time in getting it right.
- What’s after launch? There is a high with the launch founders experience but post, you’ll have to get back to work so having an idea of what comes after is a way to be 1 step ahead.
How to get to the top of Product Hunt ▶️
- Check Product Hunt Lanch Guide
"Speaking like a human, I think, is important. Also keeping it a little brief. Some people write essays, which might be interesting, but the reality is most consumers, especially people on Product Hunt, you know, they're- they're flipping through a bunch of ideas."
- Use visuals. People are drawn to visuals, so use your gallery space wisely. "The gallery is- is often the first thing that someone is gonna see once they land on the page...Some of the most interesting presentations I've seen is people use the gallery almost like a slideshow, um, like telling a story..."
"Sometimes it's also driven by like the almost like the zeitgeist, like what do people find interesting right now? Like what's sparking people's interest? Because Product Hunt, on one side, you are potentially attracting people who might be future users and customers, partners, and so on, but it's also just a general kind of like zeitgeist of the early adopter tech community."
What Ryan would do differently if he could re-build Product Hunt ▶️
- Vertical growth before expanding horizontally: The attempt to create a "discovery platform" for a multitude of communities presented significant challenges due to differing product experiences and in expanding a community. In hindsight, Ryan thinks they have focused on serving their initial tech community more thoroughly before trying to expand into different product categories like podcasts, video games, or books.
- Start monetizing as soon as possible ~2014. Ryan regrets not having tried to generate revenue, 6 months into starting PH. However, they later found that when they did start generating revenue, it happened quickly, leading to cash flow breakeven within 12 months.
- Delegate: Despite having a competent team, Ryan found it hard to delegate tasks due to being particular and having strong opinions about certain aspects.
- Careful authenticity: "I value authenticity so much, and I thrive around people who are authentic, however, there's this tension with being a founder or CEO where you can't necessarily share everything."
What skill is most helpful for moving into investing and venture capital? ▶️
- Product Management: Product experience provides perspective for evaluating different ideas and, crucially, understanding the founder's thought processes, which are critical to evaluating startup potential.
There are transferable skills one acquires as a product manager whcih are useful not only for founding a company but also for investing, for eg market needs, product ideas, and the thought process of the founder.
What matters most in life ▶️
- Small and quality deep authentication relationships: Ryan's personal journey led him to the realization that what truly matters in life are deep, authentic relationships, quality over quantity. "I care less about having a lot of friends and more about a few deep, close relationships."
- Guarantee “momentum”: Another crucial realization was the pivotal role of momentum in business, especially in startups. "Momentum is reflexive in that, you know, high momentum leads to more high momentum. Low momentum leads to more low momentum because there's this energy that- that kinda goes through companies where, when there is momentum, when people are shipping, when things are going well, other people feel that energy, and they wanna do the same."
- Power Law of Investing: In the investment world, it's often one company that returns more than all others combined. Lenny talks about the mirrors the "gravity" concept that a company is either attracting all resources and attention or losing them.
- Psychedelics as a shortcut to meditation: Psychedelics is as a potential pathway to understanding deeper truths and experiences that are otherwise only reachable through years of meditation that’s helped Ryan out through difficult personal times. "You could either meditate for five, 10 years to work your way up the mountain towards, you know, enlightenment, or you could just take some psychedelics, visit it for a little moment, see what it's like, and then be motivated to, to work on getting there more naturally."
Which ideas Ryan would upvote ▶️
- TikTok over Instagram Reels: Because he thinks Reels is "TikTok, but like two weeks late".
- Topo Chico over LaCroix: Despite identifying as a LaCroix person, Ryan would choose Topo Chico when it's available due to the bottle design.
- Lifestyle over locale for Tech: Ryan prefers LA Angeles over the Bay Area for lifestyle reasons (weather, hiking, more affordable housing), but he suggests that for a recent college grad or someone new to the tech industry, the Bay Area would be a better choice due to the potential for serendipity and networking.
- Light mode over Dark mode: Despite popular preference for dark mode, Ryan prefers light mode. He cautions that founders who prioritize such features over achieving product-market fit might be focusing on the wrong things.
What founders of consumer companies do to succeed ▶️
- Consumer startups are tough, but not impossible: "Monetization is generally harder than like a B2B company," and "you're always fighting for attention.". The consumer social or gaming is probably the the hardest and the one filled with the most failures.
- Identify your unique insight: Ryan suggests using a problem journal or immersing yourself in communities to gather insights and come up with unique ideas, and this takes time.
- Understand and adapt to trends: For eg, Airbnb's strategy shift to cater to the remote working lifestyle as an example of a company that successfully responded to consumer behavior shifts. The other is technology shifts. So, what- what new thing can you build today that couldn't be built yesterday, and why?"
- 'Why now?' Given that many people are likely trying to build something in the same space, a unique answer to the 'Why now?' question can help you stand out.
Deciding to serve a niche or broad market ▶️
Start narrow and expand over time: "the more narrow you're- you're generally... the easier it is to build a great solution for those people, because now you can actually hone in the product experience, the messaging, and everything to serve exactly those people."
Don’t worry too much about your initial target being too niche: A niche market isn't something to be overly concerned about, even if your ultimate goal is to build a larger company. A clear eg being Airbnb, which started by offering a service that many people initially found niche - renting out extra rooms or couches in people's houses.
The surprising parts of angel investing ▶️
Good operational habits matter: When running a fund, it's not just about making smart investment decisions, but also about maintaining a high level of "hygiene.", which includes communicating with Limited Partners (LPs), handling fundraising, and following up with the founders you meet.
Never count out a portfolio company until it’s over: "There are cases when I didn't think the company would make it... And then that company either pivoted or- or some massive partnership or event came through out of nowhere."
Invest holistically, not just in founders: Both as an angel and as weekend.fun, Ryan says "We try to look at it holistically in... I mean, yeah, I mean every investor would say like, 'Yeah, we wanna back, you know, resilient founders that are very driven, insightful, and all those things,' of course."
Use your personal connections for “founder first” bets: "One of the most talented like designers, engineers, product builders... I'm gonna bet on you because I believe in you. I'm not sure about this first idea... but he's probably gonna launch 10 apps, and the 11th is gonna be a massive success."
Advice for folks wanting to get into angel investing ▶️
There are various options today, ie
- Angel: If you have disposable income, you can begin angel investing immediately. There's no sign-offs required. You have maximum flexibility. The risk is that you should be willing to potentially lose all of it, with the hope of making a return in the long term.
- Scouting: Scouting is another option with increasing availability in various forms. Some scouting programs allow individuals to deploy capital on their own, while others require approval for specific deals.
- SPVs (Single Vehicle Investments): SPVs let you raise money from LPs to invest in specific companies. Ryan highlights the advantage, saying, "one, you get deal-by-deal carry," and "it allows you to also bring in maybe very strategic, helpful people into that particular round for that company."
- Raising a fund: More work and responsibility come with this option, but it provides flexibility and the ability to deploy checks into many companies.
If traditional investment avenues aren't accessible, Ryan suggests a unique approach: "you can also do is just like pretend angel invest.And that doesn't mean that you're meeting the founder and like writing a check, but you can write memos, or you can like almost create a fantasy portfolio."
Ryan believes investing and building as interconnected, hinting at his future: "investing will always be a part of my future, but I also love building. Building is the most fun, so creating something is hopefully in my future."
This is a human edited summary of the podcast episode with Ryan, by Gaurav Chandrashekar (@cggaurav, productscale.xyz). To listen to the full episode, go here.