Aug 7, 2022 · 1h 9m · lennys-podcast
How to launch and grow your product | Ryan Hoover of Product Hunt and Weekend Fund
0:00 / 0:00
▶ Watch on YouTube →
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this in-depth conversation, Lenny Rachitsky interviews Product Hunt founder and Weekend Fund investor Ryan Hoover on navigating the psychological realities of entrepreneurship, executing high-impact product launches, and evaluating early-stage startups through a product lens.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Lenny holds 25.6% of the talking time here. How this is scored →
Lenny as informed peer 3.2 Guest teaching 3.1 Guest disagreement 1.1 Lenny pushing back 0.1
speaking balance: gold is Lenny, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 46:06 Dark mode red flag hot take
Ryan takes a playfully aggressive contrarian stance, calling a founder building dark mode before product-market fit a major red flag.
Hardest push from Lenny ▶ 13:22 Lenny pushes back on writing speedWhen Ryan asks about essay writing time, Lenny firmly corrects any assumption that deep research can be done quickly, citing hundreds of hours required.
Biggest teaching moment ▶ 32:30 Lessons from premature horizontal expansionRyan delivers a candid educational breakdown of how trying to expand Product Hunt into books, games, and podcasts horizontally diluted focus compared to vertical depth.
Lenny holds their own ▶ 41:08 Lenny connects momentum to Andreessen's center of gravityLenny demonstrates deep venture knowledge by synthesizing Ryan's startup momentum point with Marc Andreessen's theory of companies becoming centers of gravity.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Lenny as informed peer | Guest teaching | Guest disagreement | Lenny pushing back | Why |
|---|---|---|---|---|---|---|
| Handling Tech Celebrity and Public Recognition | 3 | 1 | 1 | 0 | Lenny shares his own relatable experience with growing recognition and introversion. The dynamic is friendly and mutually empathetic. | |
| Relocating to Miami and Evaluating Cities as Products | 2 | 3 | 1 | 0 | Ryan reveals his move to Miami and shares his framework of viewing cities as products with ROI trade-offs. Lenny mostly asks open questions. | |
| Advising Founders via Microblogging Twitter DMs | 3 | 2 | 1 | 0 | Ryan explains using open Twitter DMs as microblogging prompts. Lenny compares this to his own reader Q&A newsletter format. | |
| The Craft and Time Investment of Writing Deep-Dive Content | 5 | 1 | 1 | 1 | Ryan turns the tables to ask Lenny about his writing hours. Lenny breaks down his exact research process and time investment. | |
| The Founder's Decade Test and Experimental Mindset | 3 | 3 | 1 | 0 | Lenny offers his rule of thumb on starting companies, prompting Ryan to introduce the 10-year test and the concept of treating startups as experiments. | |
| Fundraising Trade-offs and the Venture Treadmill | 3 | 3 | 1 | 0 | Ryan reflects on whether he would raise venture capital for Product Hunt today, while Lenny highlights the trap of the fundraising treadmill. | |
| Defining Clear Strategic Objectives for Product Launches | 2 | 4 | 1 | 0 | Ryan reframes product launches beyond mere user acquisition, listing recruiting, fundraising, and team morale as crucial objectives. | |
| Launch Best Practices: Avoiding PR Speak and Storytelling | 3 | 4 | 1 | 0 | Ryan details actionable launch advice, emphasizing concise human copy and visual gallery storytelling over corporate PR speak. | |
| Translating Product Management Skills to Early-Stage Investing | 3 | 4 | 1 | 0 | Ryan reviews historical mistakes at Product Hunt, including premature horizontal expansion and delayed monetization, providing a candid masterclass in startup execution. | |
| The Founder's Burden and Developing Resilience | 2 | 4 | 1 | 0 | Ryan discusses the psychological burden of wearing a mask of confidence during painful moments as a founder. | |
| Examining Life Meaning, Clichés, and Business Momentum | 5 | 2 | 1 | 0 | Lenny cites Marc Andreessen and Michael Pollan to build on Ryan's points about startup momentum and universal life truths. | |
| Rapid-Fire Game: Which Would You Upvote? | 3 | 2 | 3 | 1 | During a lighthearted rapid-fire game, Ryan offers a contrarian hot take declaring early dark-mode prioritization a red flag for founders. | |
| Why Consumer Startups Fail and Uncovering Product Insights | 4 | 4 | 1 | 0 | Ryan and Lenny exchange perspectives on consumer tech dynamics, internal habit triggers, and keeping a problem journal. | |
| The Strategic Imperative of Starting with a Narrow Niche | 4 | 3 | 1 | 0 | Lenny and Ryan align on the counterintuitive importance of targeting a narrow niche before expanding TAM. | |
| Operational Hygiene and Resilient Bets in Early-Stage Venture | 3 | 4 | 1 | 0 | Ryan outlines fund hygiene practices and explains why he never counts out resilient founders who pivot away from near-death experiences. | |
| Actionable Pathways for Breaking into Angel Investing | 3 | 5 | 1 | 0 | Ryan outlines different routes into angel investing, including angel checks, scout programs, SPVs, and simulated fantasy memo portfolios. | |
| Fund Size Strategy, Future Ambitions, and Self-Funding | 3 | 3 | 1 | 0 | Ryan discusses keeping Weekend Fund intentionally capped at 21 million dollars to preserve collaborative dynamics, while expressing interest in self-funded future projects. |
Statements from this episode (30)
Hoover: Miami is cheaper all-in than the Bay Area and LA
“It's cheaper than the Bay Area. It's cheaper than LA. When you kind of counter Kind of like all in costs.”
Hoover: Behind the confident mask, almost every company is internally chaotic
“Everyone has to wear this unfortunate mask is kind of the way I, what I used to describe it, this mask in Life and business where everything is going great and, you know, you're super confident. There are no problems. You got it all under control. And so the r…”
Rachitsky: Median newsletter post takes 10 hours, epic posts take hundreds
“I'd say the median post is about 10 hours. It's like maybe I kind of work on it through the week. So maybe like a few days through the week, but the most epic posts take hundreds and hundreds of hours that I kind of work on behind the scenes as I work on the w…”
Hoover: First drafts take only 20 to 30 percent of total writing time
“The first draft actually is maybe like 20 or 30% of the time. And then the rest is refining and getting feedback and everything else.”
Hoover: Tech culture defaults to immediately raising venture capital on an idea
“I think people who are in tech, especially are certain bubbles of tech. That's the default. It's like the first thing I do, I have an idea now let's go raise money.”
Hoover: Founders should use a ten-year commitment test before starting
“However, I think it's super important that founders see a line of sight to work on this for, I think my rule of thumb is a decade. Just do you see yourself working on this for a decade? And maybe it's not a decade that you actually work on it. It probably won'…”
Hoover: Started Weekend Fund while building Product Hunt via weekend pitches
“I started weekend fun when I was building product hunt. So took a lot of pitch pitches and calls with founders on the weekends.”
Hoover: Startups should avoid innovating on too many operational fronts simultaneously
“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.”
Hoover: Product Hunt might not have needed venture capital if personally funded
“Product isn't the type of company that needs to raise a ton of money. It's also one which is not doesn't have like direct competitors in the sense of like an Uber and Lyft situation where raising is actually like kind of mandatory and you sort of have to build…”
Hoover: Founder CEOs cannot simply give notice and exit easily
“When you're at a company, you can put in two weeks notice, one month notice. You can move on as a founder CEO. You can't like, you really can't. Now you technically can, but you can't, it's really hard to exit.”
Hoover: Product launches are often better for recruiting than customer acquisition
“And a lot of people default to things like customer acquisition. Oh, I want to acquire customers. 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 want to launch. So cus…”
Hoover: Product launches serve as overlooked team morale milestones
“One of them is team morale. And this might, I think this is overlooked. And I would also encourage founders not to get their team to I would say you shouldn't be motivated to launch a product just to get like the likes on Twitter and the upvotes on product hun…”
Hoover: Launch copy resonates better when written like casual conversation than PR speak
“One thing I've noticed among founders and just people in general is they tend to write like a PR person and not like a human and not like, you know, the way that I kind of describe Kind of a frame of writing, maybe your tagline for product or for your launch i…”
Hoover: More B2B companies do well on Product Hunt than B2C
“Some people, they ask me, hey, like, I don't know, is Product Hunt, like, Do B to B companies do well there? And I'm like, yeah, like probably more B to B companies than B to C companies actually.”
Hoover: A product background is crucial for early-stage startup investing
“Having a product background, I think is one of the most important aspects of early stage startup investing. Meaning oftentimes when you're building a new company, there are a lot of risks and there's a lot of important things to nail, but it all Ultimately com…”
Hoover: Product Hunt should not have expanded horizontally beyond tech
“So that's one regret is we should not have tried to expand horizontally. We should have just focused entirely vertically and serve the tech community, you know, better and with more things, which is effectively what we're doing now.”
Hoover: Product Hunt did not monetize until after its AngelList acquisition
“We raised a seed in the series A, we had capital to grow, and we didn't actually try to make money until after we were acquired by AngelList.”
Hoover: Product Hunt reached cash flow breakeven within 12 months of monetizing
“Once we started generating revenue, we did so very quickly and we got to cashflow breakeven. I want to say a year, maybe 12 months after we started generating revenue.”
Hoover: Momentum is reflexive and critical in early-stage startups
“Momentum matters so much. And 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 kind of goes through companies where when there is momentum, when …”
Hoover: In VC, one winner can return 3-5x all other investments combined
“The power law of investing where it's in most people's situation. It's one company is returning. You could invest in a hundred companies. One of those companies is probably gonna return three to five X and the returns of all the others, maybe combined in some …”
Hoover: Early-career tech workers should choose San Francisco for serendipity
“If I was, you know, a new college grad or someone young and new and kind of tech industry, definitely San Francisco, you'll create a lot of serendipity. You'll, you'll meet a lot of people, but from a lifestyle perspective, LA LA, I just find more enjoyable.”
Hoover: Prioritizing dark mode before product-market fit is a red flag
“If a founder is prioritizing dark mode before they have product market fit too, it's like a big red flag for me. That's a little bit of a hot take. Some people are gonna hate me for that, but I don't know. I don't think dark mode matters for like, 99% of peopl…”
Hoover: Consumer social and gaming startups have the highest failure rates
“I think like consumer social or gaming, like games, building games, probably like the hardest and the one filled with the most failures.”
Hoover: Building a consumer company without a unique insight is nearly impossible
“I think it's really hard to build a consumer company without some sort of unique insight, maybe impossible.”
Hoover: Targeting a narrow audience makes building and messaging easier for startups
“It's effectively the more narrow your idea generally, and this is where I throw in the big asterisks, like not for everything, there's always contextual differences, but generally the easier it is to build a great solution for those people, because now you can…”
Hoover: Weekend Fund has invested in over 110 companies
“We've invested in over a 110 companies now.”
Hoover: Raised a fund because he lacked personal angel capital
“So that that's the decision that I decided back in 2017 is I wanted to raise a fund. It's a lot more work to raise the capital and there's a lot more responsibility and managing funds and so on and so forth. But it provided me with the most flexibility and in …”
Hoover: Aspiring investors can break in by building fantasy portfolios
“One thing you can also do is just like pretend angel invested and That doesn't mean that you're meeting the founder and like writing a chat, but you can write memos or you can like almost create a fantasy portfolio. And this is what Vedika before she joined, j…”
Hoover: $21M might be the largest fund Weekend Fund ever raises
“Our latest fund is twenty one million. And that might, I might change my mind on this, but that might be the biggest fund we ever raise. I might keep it around that same size for the next one, because it really allows us to be like really collaborative.”