Lenny's PodcastHow to launch and grow your product | Ryan Hoover of Product Hunt and Weekend Fund
EVERY SPOKEN WORD
150 min read · 30,003 words- 0:00 – 3:23
Teaser
- RHRyan Hoover
I don't know how to articulate that- that feeling, but that flutter in your stomach that you wake up with in the morning of just anxiety and stress and- and worry. Um, being a CEO or founder makes it slightly harder, uh, in some ways because you still have to put on this mask. You have to put on this face of confidence externally and- and internally as well, where people need to trust you. You also don't want to subject them to the same anxiety that you're feeling and be 100% transparent.
- LRLenny Rachitsky
(instrumental music) Ryan Hoover is the founder of Product Hunt, which you already know. He's also a former product manager, which I did not know. Currently, he's a full-time investor with his fund, The Weekend Fund. He's also an author of a bunch of great blog posts and an actual book called Hooked. He's also really good on Twitter, and in my opinion, a very special human being. Ryan Hoover, welcome to the podcast.
- RHRyan Hoover
Hey, Lenny. Thanks for having me. I've been reading a lot of your blog posts over, I don't know, past two or three years now, and I'm glad to- to see you do the podcast now. It's cool.
- LRLenny Rachitsky
Thank you, man. That compliment will go straight to my heart, and I will think about it often. I appreciate that-
- RHRyan Hoover
Cu- cut that and put it on Twitter. There you go. Yeah. (laughs)
- LRLenny Rachitsky
(laughs) That's the clip. We're done. (laughs)
- RHRyan Hoover
Yeah. Um, podcast over. (laughs) .
- LRLenny Rachitsky
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- NANarrator
At least 40%.
- LRLenny Rachitsky
And how many of them screw that up? And what happens when they do?
- NANarrator
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- LRLenny Rachitsky
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- NANarrator
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- LRLenny Rachitsky
If you'd like to learn more or get started, check out Flatfile at flatfile.com/lenny.
- 3:23 – 9:02
On being a tech celebrity
- LRLenny Rachitsky
You're such a tech celebrity. Everybody knows Product Hunt. Everybody knows Ryan Hoover, at least in tech. And I'm curious, how often are you recognized walking down the street in life? And has there ever been like a super awkward or super hilarious moment of that?
- RHRyan Hoover
Yeah, so it's probably 10, started in late 2013 and quickly got a lot of traction in- in the tech- tech sphere. So yeah, people in tech, um, might recognize me. People I said in tech doubt- doubt they recognize me. Um, I actually do wonder subconsciously if I grew my hair out to avoid being recognized. Um, I'm not sure if that's true or not, but anyway, it's been a couple years or so growing my hair out and I'm like, "Ah, I just kind of want to like disappear sometimes." But, you know, in San Francisco where everybody's in tech, um, there's a lot of that. And probably the- the- the moment where I was like, "Oh, this is- this is like a thing," um, it was probably early Product Hunt. And, uh, I was at... Do you remember... I don't know if you know this. Do you know a club, um, called DNA Lounge? And they did something called Booty-
- LRLenny Rachitsky
Mm-hmm.
- RHRyan Hoover
... every Saturday?
- LRLenny Rachitsky
Mm-hmm.
- RHRyan Hoover
It was like a mashup dance party.
- LRLenny Rachitsky
Yeah. Yep.
- RHRyan Hoover
Yeah. Super well known in the Bay Area. Really fun- fun, uh, kind of experience. Anyway, I remember being with friends and drinking like- like one does, and somebody turns around and says, "Is that the Product Hunt guy?"
- LRLenny Rachitsky
(laughs)
- RHRyan Hoover
That was the first time that sort of happened in that setting where I was like, "Oh gosh, now I have to like think about my actions and I can't just like be entirely like loose and you know, relaxing with my friends." And um, so anyway, there- there's always pros and cons to those types of things. Um, but you know, it- it definitely is, makes you more aware of... I'm already a very like sometimes anxious and like self-aware person in terms of like my surroundings. And so when you combine that with, oh, these strangers might be watching me, it's not the best thing in the world, but it's okay.
- LRLenny Rachitsky
I've actually gotten a little bit through that same experience recently in like- like a much smaller sense where I... With this newsletter and the growth of this thing, there's meetups happening all over the world.
- RHRyan Hoover
Mm-hmm.
- LRLenny Rachitsky
And so I've been going to the SF meetups here and there and it feels very strange to be like known and people get... They're like taking pictures of me.
- RHRyan Hoover
Yeah.
- LRLenny Rachitsky
Like what the- the hell's going on? Because I started this thing as COVID hit-
- RHRyan Hoover
Yeah.
- LRLenny Rachitsky
... and it was like everyone's at home. I was just typing on my computer. Didn't have to go anywhere.
- RHRyan Hoover
Mm-hmm.
- LRLenny Rachitsky
And as the world has emerged, it's become a new- a new thing I'm dealing with on a much smaller scale.
- RHRyan Hoover
Yeah. Yeah. Events are- events are fun. Um, we threw a bunch of them at- at Product Hunt. And, uh, yeah, you- you could do a lot of selfies and a lot of like handshakes and it's- it, there's- there's some energy there. I'm an introvert though, so by hour like three or four, I'm just like, "Uh, uh, I need to use the restroom because I haven't been able to escape and I'm socially exhausted." So, but they are fun.
- LRLenny Rachitsky
I know, uh, exactly what you mean. I am also an introvert and I get so drained doing things like that. I was gonna ask you about that. So...Yeah.
- RHRyan Hoover
Yeah.
- LRLenny Rachitsky
Um, on the same lines, you're- you're a very public person. You tweet a lot, you share a lot. You do a lot of podcasts and things like that. What's something that people don't know about you?
- RHRyan Hoover
Yeah, um, you're right. I- I probably sh- uh, maybe overshare, uh, on Twitter and other things. Um-
- LRLenny Rachitsky
No, that is not what it's about.
- RHRyan Hoover
There is a list of ... (laughs) No, no, I know, I know what you're saying. Um, but there's also a whole series of things that I don't talk about. Um, some of them ... Well, anyway, I won't, I won't talk about the things I can't talk about. Uh, but one thing that, um-
- LRLenny Rachitsky
Shoot.
- RHRyan Hoover
... one thing that most people don't know about, I know, there- there are certain juicy things, uh, like everybody has in their life. Um, I recently moved to, well, I guess it's been a year, um, I moved to Miami about a year ago and, uh, I haven't been talking about it publicly primarily because I just didn't want to be lumped into, oh, another person moving to Miami. Like, I- I don't know, I just, there's no benefit or like reason for me to do so. I- I want my friends there in Miami to know I'm there, but otherwise I don't need the world to know. I guess now they will. Um, that said, in Miami, you know, we're- we're there about two thirds of the year. So I'm actually in California right now, um, as you know, the summer humidity come- comes through Miami and hurricane season. We're- we're planning to do more of, um, I wouldn't call it nomadic, and I wouldn't call it bicoastal per se, but something like that, where two thirds of the year we're in Miami and then maybe a third we're in New York or LA or someplace else. Um, and I love that. Um, fortunately we have the flexibility, uh, when I say we, my girlfriend Suzie and I, to just carry our laptops and work anywhere. So it's been, it's been a nice lifestyle kind of shift.
- LRLenny Rachitsky
I did not know that. That is very interesting. Why did you get pulled into Miami? What pulls you there?
- RHRyan Hoover
Yeah. You know, um, so the way I describe, city- cities are kind of like a product. So if you're in the supermarket or ... Supermarket, I sound like an- an old- old person. Uh, if- if you're at a store, you're looking at different products, or if you're online, you're evaluating different products, and they each have like a cost and they have some benefits, um, or values or whatever you- you want to use to describe it. And for me, each city is kind of like that. And so, you know, in terms of cost, there's cost of living in terms of housing, uh, food, taxes, a bunch of things that go into the cost of living in the city. And then the city provides a lot of benefits and- and things like that. And so in LA ... So I was in Bay Area for 10 years, LA for two, Miami for one now. They each have their own pros and cons. They each cost respectively different prices. And so we visited Miami a year and a half ago, and we just fell in love with lot- lots of it. Um, we also ... It's just cheaper. It's cheaper than the Bay Area, it's cheaper than LA, um, when- when you kind of counter- count like all-in costs. Um, and we had a bunch of friends move there. So we enjoyed the city, we were like, "This is good, strong ROI. Uh, this is a good product. Let's- let's move there." Um, but at the same time, as I mentioned, like we are traveling and- and exploring other cities, so it's- it's kind of the best of both worlds for us.
- 9:02 – 11:15
Using Twitter DM's as a content machine
- RHRyan Hoover
- LRLenny Rachitsky
Changing topics a little bit. Something that I've noticed you do recently, which is super cool, is you offer people the chance to DM you questions that they have about their startup or their journey as a founder, and you just offer to give them free advice, and then sometimes you tweet the DMs to share that with more folks. I'm curious just how many people have DMed you, 'cause this is such a cool offer, and what have you learned going through this and kind of hearing people's questions?
- RHRyan Hoover
I first opened up my DMs ... I had them closed, which is like traditionally the default on- on Twitter for a long time, because I was like, "Oh, if I open them up, I'll just get a bunch of spam and I don't need another inbox to- to cull through." I opened it up quietly and um, actually didn't get a lot of spam, uh, surprisingly. Like yeah, people would shill something or promote something, but it wasn't too bad. So I- I left it open and then, uh, I forget, one day I was ... Maybe I was like on the elliptical bike or recumbent bike or something, and I was just like ... I- I tend to get on the bike and just hold my phone up and just do emails and work. And so, um, I just said, "Hey, DM me if you have any question, any founders, and I'll try and like answer as many as I can." And, um, part of my motivation for that was, I don't know, I was just killing time, and the other was I used to blog a lot. I used to write a lot. Um, I don't know, I've written hundreds of blog posts, but not so much anymore. I rarely write anymore. And part of it's because it just takes so long to write, and sometimes I don't feel like inspired by any topic. It's- it's sort of like a writer's block. And so 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. I don't have to think about the pro- prompt. And then the answer is- is, in some ways a way for me to actually think about that- that topic, almost like refine my own thinking in- in some sense. And so I started doing that and then I realized, well, maybe other people have similar questions and maybe other people have other answers and other ideas too. So 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, um, and just put it on Twitter. And, you know, it's been fun. I do that maybe once every three or four days, I share a new question and answer and sort of like a, it's like microblogging in a way. I guess that's what Twitter is, but like, it's kind of like a real microblogging kind of like, uh, um, activity
- 11:15 – 14:48
The questions most founders ask
- RHRyan Hoover
for me.
- LRLenny Rachitsky
Is there anything that's kind of surprised you or that you've learned from founders, what they ask you about like, "Wow, I didn't expect this was going to be such a common problem or question?"
- RHRyan Hoover
I wouldn't say anything like super surprising. However, a lot of people ... So you could do the same thing on Twitter and say, "Hey, AMA, ask me anything in public." The thing is, people are not gonna ask certain things, um, for a lot of reasons. And maybe the biggest surprise was a lot of people are pretty vulnerable. These are strangers, founders who DM me saying, "Hey, I'm ... We have three months runway left. We're running out of money. Here's the situation. What advice do you have?" Or just things that, you know, everyone has to wear this unfortunate mask, is kind of the way I, what I use 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 reality is that's not the case. Like if you peered inside of almost every single company, it probably looks chaotic in- in different ways. And so I guess, I guess maybe the biggest surprise or...... thing that I value the most is the authenticity of people willing to share some of these, um, vulnerable moments and questions.
- LRLenny Rachitsky
Awesome. What's interesting about your format is, as you were talking, I kind of realized it's very similar to my newsletter format, which I, which I think is part of the reason it worked, is it's based on people asking me a question and then I answer the question.
- RHRyan Hoover
Yeah, it's true. Yeah.
- LRLenny Rachitsky
And that, and that ends up forcing you to have like concrete, actionable advice. So you've kind of-
- RHRyan Hoover
Mm-hmm.
- LRLenny Rachitsky
... developed an even more interesting way of doing it on Twitter, where it's more focused. So very smart.
- RHRyan Hoover
I've always liked your format, by the way, in that you're, um, you're a curator in many a sense. Like, yeah-
- LRLenny Rachitsky
Mm-hmm.
- RHRyan Hoover
... you have a lot of experience and good ideas, but you're not trying to answer all the questions, in that you're really pulling in experts in their domain expertise to, like, find answers or inspiration. And I've always liked that format because, one, it, I think leads to better, better results, better content, better answers. But also it's arguably easier. Um, like imagine if, if you tried to like write... Well, you, you're shaking your head almost like maybe it
- LRLenny Rachitsky
Like if I had the answers-
- RHRyan Hoover
... sounds easy, but-
- LRLenny Rachitsky
... I'd be like, "Oh, here you go. I'm done." You know, the research takes a lot of work and time, but, but I do agree-
- RHRyan Hoover
Hmm.
- LRLenny Rachitsky
... it's, ends up being a lot more useful and, and, and valuable.
- RHRyan Hoover
Yeah.
- LRLenny Rachitsky
And the reason I did that, just to kind of explain that briefly, is when I left Airbnb people kept coming to me and asking me like, "Hey, how did Airbnb do this thing? How'd they do that thing?" And I was just like-
- RHRyan Hoover
Hmm.
- LRLenny Rachitsky
... like, they, they don't know what they're doing, they just did this thing and who knows if that was the thing that helped them or if that was the right way of approaching it. So I wanted to do this like what does everyone do and what seems to be the pattern of the thing that works? And that kind of-
- RHRyan Hoover
Mm-hmm.
- LRLenny Rachitsky
... led to this approach. And it takes a lot of time, especially this new series that we're gonna chat a bit about that I worked on where it's just, like, endless interviews and chats and researches and watching-
- RHRyan Hoover
Yeah.
- LRLenny Rachitsky
... interviews. But yeah, it works out.
- RHRyan Hoover
Yeah. Yeah. You, you have, uh, how many hours actually do you put into, like, a typical essay?
- LRLenny Rachitsky
Oh, a reverse question. Uh, I would say-
- RHRyan Hoover
Yeah.
- LRLenny Rachitsky
... the median-
- RHRyan Hoover
I don't know if I'm supposed to ask you questions, but I'm curious. (laughs)
- LRLenny Rachitsky
This is banned. No, it's cool.
- 14:48 – 18:28
When should you start a company?
- RHRyan Hoover
else.
- LRLenny Rachitsky
That's exactly how I find it. Question I wanted to ask is, startups are so fricking hard. They almost always fail. It's always just like, "Oh my God, this is... Why am I doing this to myself?" My general advice-
- RHRyan Hoover
(laughs)
- LRLenny Rachitsky
... to founders is like, don't start a company unless you just like can't not start a company, because it's so hard. What's your take there? What do you think? What do you advise founders for when they're thinking about, "Should I start a company? Should I not start a company?" Which, "How should I approach this?"
- RHRyan Hoover
Yeah, I do, I do spend time ironically like challenging founders sometimes when they're thinking about raising or thinking about an idea to, to not raise. I think people who are in tech, uh, especially our 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. And we've, we've gone through some like pretty massive bull cycles where that, that was possible for a lot of people. But it's a huge decision. So with, with Product Hunt it was a side project from the beginning. It wasn't actually intended to be a startup at all. But in the beginning, you know, it was a newsletter then it was a website, and it was about four to five months before we even incorporated. And we got a lot of traction. So it was during that time I was really, uh, just thoughtful around like, "Should we raise? Um, do I wanna work on this for many, many years? Um, what's the opportunity? Is this even a venture-backable, like, idea?" Like, all those questions were circulating in my mind for a while. And this was also in a time when the market was pretty... was similarly bullish. This is, uh, end of 2013, early 2014. And investors were, were using Product Hunt to reach out to me, they were sort of courting, courting me and, um, kind of doing that whole song and dance to invest, but I, I just wasn't sure if I wanted to. And so, I don't know, I think a lot of the- those decisions are very personal and contextual. 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't. It e- it'll probably fail before then, (laughs) as most startups do. But I think it's a good litmus test for yourself to be like, "Do I actually care about this enough?" And am I, am I really stoked to work on this for many, many years? But then, you know, the other thing is, I think a lot of people also think, "I need to start a company, I need to start a startup." And they skip to that step without just tinkering and building and... You know, Product Hunt, we called it not even a side project, we called it an experiment. And that framing I think is, for me, has always been helpful because it's... An experiment is really not about success. Of course you want it to be successful, but the goal is not "success." I put that in quotes. It's really to learn and, you know, see if people want this thing and then kind of adapt. And so, like, an experimental mindset is helpful and I think a valuable way to start. It even goes back to like why ... running the Fund, Weekend Fun. It's like, what are you tinkering with on the weekends, you know? And how can you be more curious and experimental in kind of your exploration of new startup ideas.
- LRLenny Rachitsky
I didn't know that's why it was called the Weekend Fund. I thought it's because you worked on it on the weekends. Or is it both?
- RHRyan Hoover
(laughs) It had like multiple meanings. Yeah. It was th- three meanings. One was, was that I started Weekend Fun when I was building Product Hunt. So took a lot of pitch, pitches and calls with founders on the weekends. Um, two, I think a lot of great ideas start by like, metaphorically speaking, nights and weekends, um, kind of side projects or ideation. And then the third reason was it was like more friendly. I don't know. I didn't wanna name it Hoover Capital or something like sterile. I wanted it to be-
- LRLenny Rachitsky
Wait, that's an awesome name.Hoover Capital, wow.
- RHRyan Hoover
Hoover Capital. Right. (laughs)
- LRLenny Rachitsky
(laughs)
- RHRyan Hoover
I don't know. I- I feel, well, I will-
- LRLenny Rachitsky
Yeah, it's not on brand.
- RHRyan Hoover
I'll, I'll, yeah.
- LRLenny Rachitsky
But it's powerful.
- RHRyan Hoover
Yeah, not on brand for me.
- LRLenny Rachitsky
Yep.
- 18:28 – 21:48
Would Ryan raise money for Product Hunt if he could do it again?
- LRLenny Rachitsky
- RHRyan Hoover
Yeah. (laughs)
- LRLenny Rachitsky
As you know, I asked people on Twitter what questions they would wanna ask you, and so I'm gonna intersplice these questions as we go through this. And you just touched-
- RHRyan Hoover
Cool.
- LRLenny Rachitsky
... on Product Hunt and fundraising, and I'm curious if you were to go back and, and do it again, would you raise money for Product Hunt or would you not?
- RHRyan Hoover
Great question. So at the time, this is also the thing I ask founders is, "Why do you need to raise money? Like, what is it for?" And surprisingly some people are like, "Uh, I don't know." Like, they don't have a clear answer. For me, it was pretty obvious, like we needed, we needed to hire. We needed people. Like, I, I didn't have personal capital to, to pay people. There was an alternative, uh, reality where we actually built it open source. I was thinking like, "Is that possible?" Like, we're building something for the tech community. I'm sure a lot of people would love to work on this. Could we build it in an open source way? But that, like, that's really hard to do, and when you're building a company, you probably don't wanna innovate on too many things, um, including, like, essentially how to build a product and build a team. So anyway, to answer your question, if... I, I don't, I don't know what the right... At the time, raising money was the right decision because I, I wanted to hire and I didn't have personal capital. There really weren't, uh, any other realistic options, I don't think. Today, I could get further with my own- I'm not super wealthy and I'm super illiquid, but I have at least enough money where I could have funded, you know, maybe a year of development with this very small team. So today, it might be a little bit different, in which I might not raise venture capital because Product Hunt isn't the type of company that needs to raise a ton of money. It's also one which is not, um... It doesn't have, like, direct competitors in the sense of, like, an Uber and Lyft situation where raising is actually, like, kind of mandatory (laughs) and you sort of have to build a massive war chest to compete. So there, there is a scenario where if I had more money, then maybe I would to raise venture capital. But yeah, there, there's a lot of other, like, decisions and other things that probably, uh, bigger mistakes I think I made, um, not that raising the money was a mistake by any means. That was, I just, I think the right decision then, but yeah, there's a lot of learnings and hindsight's 20/20.
- LRLenny Rachitsky
The point you made about, like, you just needed money to, like, run the thing, I think that's so, so overlooked when people bash the idea of fundraising for a startup that maybe didn't need it. Like, you just need money.
- RHRyan Hoover
Mm-hmm.
- LRLenny Rachitsky
Like, you don't have just money to burn and go into debt. That makes sense to raise some money and see where this thing goes without really knowing where it's gonna go.
- RHRyan Hoover
Mm-hmm. Yeah, especially if it's... I mean, I think it's very important to raise, raise from people who are aligned with you too. Meaning, like, why does this person want to, whether it's an angel or a fund, invest in your fund? Um, sorry, not fund, your company. Um, when you go down certain path when you've raised a series A, B, C, like, you have different expectations than when you raise your pre-seed or seed round. So, I think also understanding, like, you know, what you're signing up for is super important.
- LRLenny Rachitsky
What kind of treadmill you're, you're getting on.
- RHRyan Hoover
Yes. Yeah, 'cause you can't get off. I mean, you can, but it's not like a company. I always say, like, when you're at a company, you could put in two weeks notice, one month notice, you can move on. As, as a founder or CEO, you can't. Like, you really can't, um... Now, you technically can, but you can't. (laughs)
- LRLenny Rachitsky
Yep.
- RHRyan Hoover
It, it's really hard, um, to, to exit.
- LRLenny Rachitsky
Yeah. I look at the Airbnb founders who've been doing this for 15 years and, like, you know, they're doing f- well in life, but they also,
- 21:48 – 24:52
When should companies launch products?
- LRLenny Rachitsky
it's very hard to leave.
- RHRyan Hoover
Mm-hmm.
- LRLenny Rachitsky
Yeah. Coming back to Product Hunt, people launch their products on Product Hunt. That's the thing. And I'm curious, founders are always so obsessed with launching and the power of a launch, and we got off launch. Do you think launches are worth it for a company? Is that something founders should be spending time on, or is it often better just to not even spend time on that and just build slowly?
- RHRyan Hoover
Yeah, I, I, I always kinda... Whenever I share, like, my perspective on stuff, I, I unfortunately always, always like, "It kinda depends," which is kind of, like, sounds like a cop out answer. So it's, it's more, my answers are usually more nuanced. And the thing about launching is, is going back to why are you raising money, what's the goal? Same thing. Why are you launching? And th- A lot of people default to things like customer acquisition. "Oh, I wanna 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 wanna launch. So customer acquisition is one, to get the word out. Another can be recruiting. So by, you know, sharing your story, getting people excited, it might make it easier to recruit and get people excited about, you know, what you're building. Another is fundraising. Sometimes it can create momentum, you know, as, as other investors they do read the news and they know that, you know, when this company is more public, there might be more heat around a, a particular deal. Feedback is one, um, feedback from users, feedback just serendipitously, and, and sort of another one is partnership. So as you launch, you might also encounter more partnerships, more opportunities. I think there's a serendipitous effect of launching. So I think understanding, like, what are the priorities in the business? Like, if you... It might not be customer acquisition at all. It might be that we need to recruit and hire, let's launch so we can get the word out. Hopefully that will help land, you know, our next, you know, engineers, designers, or whoever. And then I'll also say there's, like, these little side benefits too of launching, um, that we see a lot through Product Hunt. One of them is team morale. And this, this might, I think this is overlooked, and I, I would also encourage founders not to get their team too, um... I would say you, you shouldn't be motivated to launch a product just to get, like, the likes on Twitter and the upvotes on Product Hunt. But there is a gr- like, a powerful team morale and kind of building moment there where you can all celebrate what you've accomplished and what you've built and put it out to the world. And, you know, somebody on the team can share, you know, the, the, the Product Hunt launch or, you know, some Tech Crunch article with their, their mom and, you know. Like, that seems like a trivial, kind of meaningless thing, but it actually matters for a lot of people. And then the other thing is SEO. So if SEO is, like, part of your strategy, having articles, positive articles, having a, a positive Product Hunt launch, things like that can also be helpful.
- LRLenny Rachitsky
That's awesome. I love that last point about morale. I- I hadn't thought about that. You've seen probably more launches than any person out there. How many launches of startups would you estimate you've kind of like seen or been, I don't know, an observer of, if that makes any sense? (laughs)
- RHRyan Hoover
Um, I should look at our database on Product Hunt and see how many launches we've had 'cause it's gonna be a subset of that. I mean, by seeing, uh, some of it's very high level, but tens of thousands over the years.
- 24:52 – 26:27
What makes a launch successful versus not?
- RHRyan Hoover
- LRLenny Rachitsky
Okay. So when you think about that, do you have any sense of what correlates with a great launch versus just like an okay launch? What do, what do founders miss with how they launch?
- RHRyan Hoover
Yeah, I mean this goes back to college and, and the, you know, I won't go on my own rant about education, but you know, English class and writing class, a lot of teachers teach people to write with big words and fill pages of content and basically not speak like a human. And so one, 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 not like, you know, the- the- the way that I kind of describe kind of a frame of, of writing maybe your tagline for Product Hunt, um, or for your launch in general is like how, how do your customers or your users describe your product to other people? Or another frame is how do you describe it to your friends? Like when you're just, you know, hanging out, like how do you describe what you do, what you built, what it's for? And that language I think resonates with people because it feels way more authentic and the people that use buzzwords and, and vague language, it just doesn't click. People see right, people are sick of the PR speak. And so I think the language and the microcopy, copywriting matters so much. And then there's a lot of other things around like which go more to the product and less about the launch, like do you really understand who you're building for and do you understand how to communicate the value prop? Like where does it fit in the mind of the user? There's sort of a lot of, um, I guess more strategic kind of like decisions that go into, to that, uh, before the launch.
- 26:27 – 30:01
How to get to the top of Product Hunt
- RHRyan Hoover
- LRLenny Rachitsky
I imagine each of those, uh, points can be its own podcast and blog post. One of the questions that people asked me on Twitter was j- the classic, "How do I get to number one on Product Hunt?" So my question to you is, I know that's like there's not gonna be a silver bullet. Is there like a guide that you point people to that's like, "Here, just follow this advice." And or, I don't know, two or three key things that you just gotta get right?
- RHRyan Hoover
Yeah. Yeah, so we, um, in the post flow there's actually a, a, link- links to a bunch of guides and FAQs and things like that. So it's really easy to find like sort of the best practices there. The team also has like this checklist, so once you launch there's like a checklist of things, um, recommendations or tips. And I'm actually forgetting like what each of them are specifically right now. But some of the things that I've noticed that make a big difference is we've already talked about the tagline copy that goes to not only the post but also the maker, usually people tend to add like some introduction, some context. Uh, generally a lot of people will, they, they manufacture PR speak there too. And so speaking more 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
- NANarrator
(laughs)
- RHRyan Hoover
You know, they're, they're flipping through a bunch of ideas, they're looking for things that spark their curiosity and interest, and they're probably not particularly interested in reading like an essay, you know, from, from the maker. So keeping that short I think is helpful. And then another big one is the gallery is, is often the first thing that someone is gonna see once they land on the page. And so just naturally our eyes gravitate towards visuals. And some of the most interesting presentations I've seen is people use the gallery almost like a slideshow, like telling a story, where each slide is, is communicating like a different, well, a story of some sort. It could be like, "Here's the before and after with our product." Or, "Here's the evolution of what this product can do." Um, there's many different ways to approach it, but like a very clean, you know, visually interesting story, um, can also be a great way to like capture people's interest in what you built.
- LRLenny Rachitsky
Awesome. That was very tactical and helpful. If you were to launch something on Product Hunt yourself and it wasn't like hunted by Ryan Hoover, do you think you would get to the top?
- RHRyan Hoover
(laughs) I, I mean, I don't know. It's, it's funny because if you, we should do some like historical analysis on Product Hunt 'cause I'd be curious to know the actual numbers, but it varies all over the board. So some people they ask me, "Hey, like, I don't know, is Product Hunt, like do B2B companies do well there?" And I'm like, "Yeah, like a, probably more B2B companies than B2C companies actually." And so you see, you know, seemingly boring companies that tap into something that, that, that, uh, people find useful or resonates, resonates with them, um, can go to the top. And then you also see the weird wacky stuff, you know, the, the silly apps also hit the top. So I dunno, it really varies and sometimes it's also driven by like the, almost like the zeitgeist, like what did 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, like what are they interested in? What do they find compelling in general?
- LRLenny Rachitsky
Got it. Okay. So I have a bunch of questions from Twitter that people wanted to ask you. (laughs) And so let me ask you a few of those and they're kind of a little bit all over the place, but we'll see, we'll see where this goes. Jessica Toy, who's a, she's a PM at AngelList. She's actually a friend, we worked together at Airbnb. She asked a great question.
- RHRyan Hoover
Yeah. Jess, Jess is awesome.
- 30:01 – 31:39
What skill is most helpful for moving into investing and venture capital?
- RHRyan Hoover
She, shout out to Jess. She's like been super helpful on the AngelList side, so she's awesome.
- LRLenny Rachitsky
Amazing. Okay. She's the best. She asked what you learned as a PM that has helped you in your venture career?
- RHRyan Hoover
Yeah. So my, my background is marketing and then product management pretty quickly. I used to work in the gaming industry, which is like I think an awesome industry. Really hard to make it in that industry, but like amazing place to learn and, um, I think product, I don't know, I have so many biases so I have to like be cautious of that. But I, 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, to nail, but it all ultimately comes down to the product that you're building. And so I think having a product management or product background is helpful in, one, having more, I guess, perspective in evaluating different ideas and, and, and arguably more important, how the founder thinks about things. So it might be less about me evaluating the, the, the market need for this particular idea, but it's what's the thought process, process in how did this founder come to these product ideas and these insights? And so I think having a product management background is helpful for that. And I don't know, I also just find it really fun to jam on product with founders. And when it's early, early days there, there's more opportunity to create some sort of impact or, you know, help shape the product in, in a slight way.
- LRLenny Rachitsky
Awesome. Basically, if you're a PM, you've got a lot of the skills that you need to be a founder.
- RHRyan Hoover
Founder and, and arguably investor, um, as well.
- LRLenny Rachitsky
Own and... That's right.
- RHRyan Hoover
Yeah.
- LRLenny Rachitsky
Okay. So, uh, Leo of SUSE Ventures, who's also
- 31:39 – 38:57
What Ryan would do differently if he could re-build Product Hunt
- LRLenny Rachitsky
an awesome dude, uh, he asked if you could go back and-
- RHRyan Hoover
I saw Leo in, uh, Miami-
- LRLenny Rachitsky
Oh. Oh, you did?
- RHRyan Hoover
... uh, not long ago.
- LRLenny Rachitsky
Oh, man.
- RHRyan Hoover
Yeah. Yeah.
- LRLenny Rachitsky
Oh, yeah. He moved to Miami too. Oh, my God.
- RHRyan Hoover
Yeah.
- LRLenny Rachitsky
Everyone's over there. Okay. (laughs) So, uh, he asked, if you could go back and build Product Hunt again, what would you do differently? We talked a bit about this, but anything else?
- RHRyan Hoover
Yeah. Um, I've been thinking a lot about this actually lately and, um, yeah, I mean, there's a few things. One, Product Hunt in the very beginning and still today is very much focused on tech, and there was at one point ambition to expand beyond tech into all different types of, you know, categories of products. So, you know, we experimented with podcasts actually, podcast discovery, we experimented with video game discovery, we experimented with book discovery. Um, and the thesis there was, okay, this could be actually a discovery platform for all of these communities to discover all these different products, and I think there was a lot of good ideas in that. However, I severely underestimated how difficult it would be to do two things. One, the product experience in Product Hunt is very different than how you would want to discover video games or maybe in the future fashion and a bunch of other types of, um, products out there. And two, it's really difficult to translate a community and expand into other communities. Like some, some have done it, like Reddit is maybe a great example, where Reddit has this massive long tail of, you know, every kind of community you can imagine, but very few companies and platforms can actually do that. So that's one, one regret is we should not have tried to expand horizontally. We should have just focused entirely vertically and, and served the tech community, you know, better and, and with more things, which is effectively what we're doing now. Another regret, another thing I would have changed is I would have, I would have actually tried to monetize and generate a revenue sooner. We, 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. And my thinking at the time was, and to some extent there's some truth to this, is like everything you prioritize is at the cost of something else. You know, you're, you're essentially taking focus from one thing to direct it to something else. And what mattered most was growth and to grow the community. But what I really should have done is dedicated maybe 10% of our focus on revenue generation because, you know, it was... Once we started generating revenue we, we did so very quickly and we got to cash flow break even, I want to say a year, maybe 12 months after we started generating revenue. So if we would have started in 2014 to make some money, we could have been cash flow break even, you know, maybe 2015, 2016, which would have just given us a lot of flexibility and kind of owning our own destiny and proving out some of the business model itself. And then like the last thing, 'cause I've been thinking about this lately, is, is delegation is, is a classic founder challenge. Um, you know, I, I'm, I'm just generally a controlling person. It's something I'm working on. And it's really hard sometimes when I have such strong opinions and I'm very particular about certain things to fully delegate and fully trust everybody. That, that said, like we had an amazing team. Like I worked with some amazing people, still people that are at Product Hunt today, like six, seven years later. It wasn't anything about the skills o- of the team. It was just my own trust and my own delegation. And what I should have done is, you know, up until shortly before I left, I was editing the newsletter every morning, for example. Like every morning I was waking up, you know, 5:00 AM, 5:30 AM, editing the newsletter and that's just kind of silly, you know, to be doing that so many years later after starting.
- LRLenny Rachitsky
I totally get that drive to just make sure everything you're putting out and that your company's putting out is top notch. I, I have the same feeling and it is hard to let go and just like, "That's not perfect, but I'm gonna, gonna be okay with that and I'll do other things."
- RHRyan Hoover
Mm-hmm. Yeah. It's, it's really hard. And I think it's a tendency that is, um... In some ways it's, it's good in that you care so much about the product as a founder, you care so much about what you're building, you care so much about the details and you need that kind of like almost OCD-like, uh, behavior. However, you also just can't scale yourself, nor are you the best person at everything. So I don't know. With hindsight, I'm like, "All right, I should have delegated more. I should have trusted people more." And yeah, there'll, there will be mistakes. I make mistakes all the time. But at the end it's going to be way net positive because you kind of have to do this to scale, your company anyway.
- LRLenny Rachitsky
That's a good segue to a question Harry Stubbings asked that he finds interesting always. What's the most painful lesson that you've learned and, but that you're also happy about to have gone through?
- RHRyan Hoover
Yeah. Yeah. There's... Actually, I w- I recently in the past couple weeks wrote a blog post that I'm not really able to publish 'cause it's, it's basically when you... There's certain things I want to share that it, it can make things challenging and complicated for others. So I don't want to put, uh, anyone else in, in a pickle. So someday maybe I'll publish this post. But to speak more vaguely about it, like there are some hard, really hard times in, in Product Hunt. Like I...... you know, we, we have all faced in, in different ways as founders or not even just as founders, just as people (laughs) . But yeah, there are some times where I felt physically ill, many different moments in, in product time. And, um, it was just really tough. And, you know, you ... I don't know if ... I don't know how to articulate that, that feeling, but that flutter in your stomach that you wake up with in the morning of just anxiety and stress and, and worry. Being a CEO or founder makes it slightly harder in some ways, because you still have to put on this mask. You have to put on this face of confidence externally and and internally as well, where people need to trust you, you, you also don't want to subject them to the same anxiety that you're feeling and be 100% transparent. So it's, it's a struggle because I think I h- I don't know, I value authenticity so much and I, I kind of like thrive around people who are authentic. However, there is this like tension with, with being a founder or CEO, we can't necessarily share everything. So anyway, everyone's gone through hardship building a company. The positive aspect of that is like if ... I think hopefully grown some empathy for founders who are going through hard situations. I think it's made me a little bit stronger, maybe thicker skinned for certain things, and just provided more, more perspective, you know, um, into the, the company kind of like building journey.
- LRLenny Rachitsky
Okay, listen to this. If you can take 15 seconds to leave this podcast a rating on Apple Podcast or Spotify or any of your favorite podcasting apps, you can enter to win $1,000 in cash plus other fabulous prizes, including a one-hour coaching call with me, a box of custom swag that I've just created that's full of really good stuff like an awesome water bottle and hat and socks and a few other things. And you also get a one-year free subscription to my newsletter and even a goodie box for Athletic Greens. It's a giveaway bonanza and all you have to do is go to lennyspodcast.com/bonanza to learn more and enter the contest. Just make sure you apply by August 14th, 2022. Again, the URL is lennyspodcast.com/bonanza. And we talked about how hard startups are and how many people should not start a company, but at the same time, part of this question, which I think you would agree with, is you're probably very happy you went through all that and, and wouldn't change, wouldn't like undo that, right?
- RHRyan Hoover
Yeah, yeah. It's kind of like, uh, you know, like a lot of things, you know, what doesn't break you makes you stronger to some extent. So it didn't break me, it just scarred me
- 38:57 – 43:13
What matters most in life
- RHRyan Hoover
a little bit, but didn't break me (laughs) .
- LRLenny Rachitsky
And turned you into the Ryan Hoover that we, that we have today.
- RHRyan Hoover
Yeah. For better or worse.
- LRLenny Rachitsky
(laughs) Maybe one last question from, from Twitter, Twitterates from Sandeep. He just wanted to know what, what have you found matters most to you or mattered most to you in life and in business versus what you thought would matter most?
- RHRyan Hoover
Yeah. Um, still figuring it out and, and I'm still asking the, the old stereotypical questions like, what, what the heck is the meaning of life? Like, what am I here for? Like all those things.
- LRLenny Rachitsky
Let me know when you figure it out.
- RHRyan Hoover
Yeah. And maybe, maybe there is no answer. Maybe the question is, is actually, um, doesn't matter. So I mean, if I'm honest, I'm still figuring all those things out. I mean, I think in, in life some of the things that I've reflected on is so damn cliche, but sometimes the cliches are true is like friends and authentic relationships have been, I don't know, they just matter so much, I think. And the older I get too, it's less about, I don't know, I care less about having a lot of friends and more about a few deep close relationships. And I don't know, I feel like that's very different than like middle school Ryan or like when you're in, on the, the playground metaphorically speaking, where everyone's trying to be popular and, you know, meet a lot of people. And even, even joining and, and being in San Francisco and in the tech community, you know, you want to meet a lot of people and network and all those, do all those things that's less interesting to me and less important. And then more on the business side, the thing I've been thinking about is like, again, I think this is obvious to a lot of people, but I think there's some nuances to it, which is 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 people are shipping, when things are going well, other people feel that energy and they want to do the same. But in the reverse, someone who might be slowing things down, not shipping, not really performing very well, that actually does the reverse too. It, it might lead other people to, to feel less motivated or care less. And so, I don't know, momentum is, is this weird thing that, you know, arguably it's one of the most important things in early stage startups and of course it's an, an input to a lot of things, but it's just so important to nail.
- LRLenny Rachitsky
Marc Andreessen talks about that, that last point that there's like a word for it that I forget that a company's either becoming a gravity and pulling in all resources and funding and attention or losing it. And it's really important as a company to know which one of those are you. And as, as an investor, you, you often want to bet on the company that's just like they're just becoming the center of gravity here and there's not a lot you can do to change that once they reach a certain point.
- RHRyan Hoover
Yeah, yeah. That's a really good point. I mean, it, it also mirrors with like the power law of investing where it's, it's in most people's situation, it's one company is returning ... You can invest in 100 companies, one of those companies probably going to return three to 5X in the returns of all the others, maybe combined in some cases. So it's, it's, it's wild.
- LRLenny Rachitsky
On the first point that you made earlier about cliches and platitudes reminds me, Michael Pollan has this point that he makes that like cliches and platitudes are cliches and platitudes because we've heard 'em so many times but that because they're true. People just say them 'cause they're so true. And as much as we don't want to hear them, like there's a reason that we hear them again and again. Uh, I had a similar recognition when I was on a little psychedelic journey where I'm just like, "Man, love is all you need. Love is all you need, man."
- RHRyan Hoover
(laughs) . Yes. Yeah.
- LRLenny Rachitsky
It's like, okay, people have figured that out (laughs) . But it was like, I feel that, I feel that right now. But it's true. That's why people, that's why (laughs) we're like, "Okay, shut up. I've heard that. That's in a song."
- RHRyan Hoover
(laughs) . Yeah, I was listening to, to a podcast about someone who was, um-... basically describing, like, psychedelics as a gateway into, like, meditation and- and everything. And- and how it could be one of those things that makes people ... It- it ... A lot of people who take psychedelics come across as another hippie cliche, like, person who repeats, like, the same things we've all heard many, many times. But there's a reason why there's a pattern there. And, you know, he describes, like, you know, psychedelics as- as one way to feel that and learn that- that feeling that you can't achieve with- with meditation, you know, with experience.
- LRLenny Rachitsky
Yeah. I think Sam Harris talks about this, where 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,
- 43:13 – 48:05
Which ideas Ryan would upvote
- LRLenny Rachitsky
visit it for a little moment, see what it's like (laughs) , and then-
- RHRyan Hoover
Mm-hmm.
- LRLenny Rachitsky
... and then be motivated to- to work on getting there more naturally.
- RHRyan Hoover
Yeah.
- LRLenny Rachitsky
This is a good time to play a little game that I invented just for you. Okay, so you're the founder-
- RHRyan Hoover
Darn it.
- LRLenny Rachitsky
... of Product Hunt. Okay (laughs) . And on Product Hunt, people upvote ideas that they like best. And so what I'm gonna do is I'm gonna give you two options, and you tell me which you'd rather ... which you'd upvote. And it'll make sense once we get going.
- RHRyan Hoover
All right.
- LRLenny Rachitsky
(laughs) That sound good?
- RHRyan Hoover
Okay, cool.
- LRLenny Rachitsky
Okay.
- RHRyan Hoover
Let's do it.
- LRLenny Rachitsky
Okay. TikTok or Instagram Reels?
- RHRyan Hoover
And- and- and is context setting, are these within the context of products I- I like and know, or ...
- LRLenny Rachitsky
Products you would choose to use, that you like better. Yeah. Not like, which will do-
- RHRyan Hoover
Okay.
- LRLenny Rachitsky
... business ... better business, yeah.
- RHRyan Hoover
Okay. Okay, got it.
- LRLenny Rachitsky
(laughs)
- RHRyan Hoover
T- TikTok for me. It's funny, Reels, I kind of joke with- with Suzie, my girlfriend. I joke that it's like Reels is like TikTok but, like, two weeks late. Uh-
- LRLenny Rachitsky
(laughs)
- RHRyan Hoover
Not entirely true, but I feel like I see a lot of TikTok videos on Instagram Reels, like, after, you know, weeks after they've been published.
- LRLenny Rachitsky
We'll see. I have some friends that work on Reels, and I'm excited to see where they go. Okay, next-
- RHRyan Hoover
Yeah.
- LRLenny Rachitsky
... LaCroix or Topo Chico?
- RHRyan Hoover
Ooh, this is a tough one because I'm- I'm generally a LaCroix kind of person, but Topo Chico, I like the bottle. So when Topo Chico's available, I'll go Topo Chico. I'm sorry, LaCroix.
- LRLenny Rachitsky
I- I totally get that. My wife's a huge Topo Chico fan. We have many, (laughs) many bottles. They're beautiful.
- RHRyan Hoover
Mm-hmm.
- LRLenny Rachitsky
They've kind of changed a bit. They're, like, super clear now. They used to have a little, a little tint.
- RHRyan Hoover
Hmm. Hmm.
- 48:05 – 55:33
What founders of consumer companies do to succeed
- LRLenny Rachitsky
consumer startups and just a few things that I've been learning there, and then angel investing. And then- and then we wrap.
- RHRyan Hoover
Mm-hmm.
- LRLenny Rachitsky
So around consumer, by the time this post comes out, I'll have released some portions of this series that I'm working on, on kickstarting and scaling a consumer business. And there's a few things I've learned there that I just wanted to get your take on. One is that ... One ... And we talked a bit about this, just, like, 99% of consumer apps seem to just, like, not work, especially if they're venture scale, if they raise money. Just, like-
- RHRyan Hoover
Mm-hmm.
- LRLenny Rachitsky
... just a reminder of how hard consumer is. Like, when is the last consumer app that really took off?And so I just wanted to get your thoughts as, what's your take there? What should founders do that are starting a consumer company?
- RHRyan Hoover
Yeah. Yeah, it's tough. I mean, there, there's... Obviously, consumer is pretty broad, so there's, like, different s- levels of difficulty. I think, um, like, consumer social or gaming, like games, building a game is probably, like, the, the, the hardest and the one filled with the most failures. And I think a lot of that is because a few things. I think, one, monetization is generally harder than, like, a B2B company. Historically, a lot of it's been, like, advertising-driven, and to do that, you have to first get to massive scale for advertisers to really care, and then you have to, you know, double it and double it and double it (laughs) again. So monetization is super tough versus a B2B company. It's like people have a problem. They have a need. They are willing to give you money, you know, on day, day one. The other thing about consumer that's tough is you're, you're always fighting different... Essentially, you're fighting for attention. And so you might be some consumer social company, but you're, you're kinda, like, competing with Netflix too, which isn't in your direct domain, but, like, people could be watching Netflix or they could be using your product or your, your social app, let's say. So now you're competing with so many different things. Many of those are incumbents where the consumer also has, like, built-in habits, routines. Like, this is a big, big part about consumers too is eventually you wanna be, like, an internal trigger in someone's mind where they, they just, without even thinking, they go and use your product or services for some reason. Usually, you don't start that way. You need, like, external triggers to, like, pull people in, but eventually, you have to get to that point. So how do you overcome those internal triggers they have for other services and other products? It's really, really hard. And, and then I think a lot of it is, um... Like, B2B companies, usually you, you have a clear, like, problem that you're solving, and you can talk to customers. You can understand what are their current behaviors, what, what solutions are they using now? What do they like about them? What do they not like about them? Whereas consumer, there's a little bit of that, but it's, it's fuzzier. You know, if you take, like, Twitter and you kind of even ask someone, like, "Why do you use Twitter?" And like, uh, people will have different answers that are all kinda, like, fuzzy, and they ultimately tend to come down to some sort of, like, innate human desire. Like, it could be, um, for Twitter, it could be about, like, I wanna be informed with what's happening in the world, or it could be I want to feel less lonely or connected to more people or something like that. Whereas if you go to, let's say, DocuSign I think is a great example of a B2B company. It's, like, super simple. It's, like, uh, a way to get legal docs signed online. That's what it does. It's a thing that people have to do. It's very clear, like, what it solves. And so B2B is just, like, easier just to navigate that, like, idea maze, um... And so with consumer, your, your first blog post on this topic touches a lot on the idea side, and I, I... A lot of it resonated with me, especially the, the insight piece, like, what is, what is the insight that you as a founder have to build this thing? Because I think it's really hard to build a consumer company without some sort of unique insight. Maybe impossible. And you can get that in many different ways. It could be through your own experiences. I used to write, like, a problem journal, like, just when things annoyed me or when things were, like, less efficient, I would write it down as, like, a note, and I didn't try to solve it. I didn't, didn't say, "Oh, here's the solution." I was just like, "This is annoying." Like, in San Francisco, one example is a lot of people don't have laundry, like, in their unit, so I'm like, "That's kind of annoying." Like, "That's a problem. Maybe there's a solution out there." So things like that. And I know, the- there's, there's a bunch of different ways, like, your, your blog post does a better summary I think of, like, the different ways different companies, like, ideated and came up with their ideas, but, uh, we have many different ways to navigate it, but it needs an insight of some sort.
- LRLenny Rachitsky
Awesome. I hadn't heard that, uh, that p- problem journal idea. I was gonna ask you if you have any suggestions for how to come up with a startup idea, and that's a really interesting one. So I guess it'd be cool to hear where that came from and what that led to or if there's anything else you found to be useful around that.
- RHRyan Hoover
Yeah. Yeah, the problem journal is one. And again, like, I think it's helpful not to try to come up with a solution but just write. Just simply write down, like, the problem you, you observed or experienced. Another one I, I think is interesting is just to, like, immerse yourself in different communities. Ideally, like, maybe, like, seemingly niche or weird long tail communities. Doesn't have to be that necessarily, but that might be where you'll see more unique insights or, or gather more unique insights, and you could do that through, I don't know, participating in subreddits, meeting a lot of people who are, like, really excited about some other thing. It could be, like, some weird robotics, like, niche hobbyist community, for example. And a lot of that I think will, will hone or just, like, create serendipity for ideas. You might see patterns or you might see, uh, problem statements emerge from many people in that community that are facing similar things. And then there's, like, the other, other component too, which is really about, like, observing trends and, and changes, whether it's, like, a consumer behavior shift. Let's take, um... An obvious one today is, is, like, distributed working. So five, five years ago when The Weekend Fund started, that was one of our themes. It was like, I, I, I think distributed working will be on the rise for a number of reasons. One, you know, it's harder and harder to recruit. Two, there's a subset of people who really value that flexibility and autonomy. And then fast-forward, we had COVID that accelerated remote working and, and now that's a huge consumer behavior shift, not just in how people work but also, like, going to your Airbnb, like, world. Like, Airbnb has shifted their entire product to support more of this remote working kind of lifestyle. Just the way that the, the homepage is now more of a catalog of places that you could explore at different times of the year versus Airbnb before was more like, "I have a very specific vacation trip that I wanna take during these days in these areas." It's, like, a very different, like, browsing kind of experience. So that's just one example. Consumer behavior shifts is one thing to observe. The other is technology shifts, so what, what new thing can you build today that couldn't be built yesterday? And so there's, there's a bunch of categories around there, like, Web3, AI, um... You know, the biggest shift that we've seen is, is mobile in, like, early 2010s. That unlocked a whole, whole bunch of things. So, so yeah, I think it's observing those shifts and those changes. Last thing I'll say on that is, like, I think...... startups. Since there are more and more people building companies and technology, there, there's essentially more efficiency. It's certainly not a, an efficient, super efficient market, but there is more efficiency in problem discovery and, and, and solution exploration. And so for that reason, you need even more reasons for things to ... sort of answers to the why now, like what's changed? What insight do you have? Why isn't this exist already? 'Cause a bunch of people are trying to build something in this space, most likely. So it's a lot of what, what we think about, especially on the investing side when we talk to founders.
- LRLenny Rachitsky
Wow. There's way too much good advice there. Have you written this down anywhere? Is there a tweet thread people can find, like, your kind of approach to coming up with an idea?
- RHRyan Hoover
I have not. I don't think so. I don't think I have-
- LRLenny Rachitsky
Cool. All right. Now, we have it
- 55:33 – 58:03
Deciding to serve a niche or broad market
- LRLenny Rachitsky
in-
- RHRyan Hoover
Maybe that's a blog post for the future. (laughs)
- LRLenny Rachitsky
Yeah. Or this is the, uh, this is the, the content for people to save and use.
- RHRyan Hoover
Yeah.
- LRLenny Rachitsky
Thanks for sharing all that. That was really helpful. One other question I wanted to ask you along these lines is around the target audience. And, uh, an insight that we both share is that it's really important to get really narrow with who you focus on initially-
- RHRyan Hoover
Mm-hmm.
- LRLenny Rachitsky
... as a startup. For founders, it's often so counterintuitive. They're like, you know, it's like, "Oh, my God. Why should I focus on a thousand people or 10,000 type people-"
- RHRyan Hoover
Mm-hmm.
- LRLenny Rachitsky
"... versus the millions that might wanna use this thing?" What's your sense and where have you kind of seen that become important, just the idea of getting very narrow on who you're going after?
- RHRyan Hoover
Yeah. It's effectively the, the more narrow your, 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 actually hone in the product experience, the messaging and everything, to serve exactly those people. And it can help with the product side. It can help with the marketing and go-to-market as well, where you, your messaging, when people land on your homepage, you don't need to create kind of a broader kind of like value prop to everybody, but really you can focus on like what is the, the problem this particular audience or community is, is facing. And so generally it's just easier. Now, there is always that challenge of like, well, is this too small? Is it too, too much of a niche if, if my goal is to build like a massive company? My bias is not to worry too much about that, because what you probably find is over time opportunities to expand beyond that. You'll see parallels maybe to other communities or other problems, and a lot of companies, you know, eventually expand well beyond that. Like, I go back to Airbnb. You know the story way better than I do, but you know, initially it was like just, you know, basically couches and extra rooms and houses and like a lot of people, most people in the US would not do that. Like my parents, not, not in a million years. Even me, like I don't wanna like stay in some stranger's like room. I want my own space, my own house. So like that, that probably at the time seemed really niche and like small, but obviously they extended, extended well beyond that now. Now if you ... Airbnb is like housing in generally speaking. Like their, their TAM is housing in, in my mind, which they haven't yet ex- expanded into like real estate sales or like long term rentals per se, but like that, that's a possibility.
- LRLenny Rachitsky
This is a good segue to the last topic I wanted to touch on, investing, which
- 58:03 – 1:02:12
The surprising parts of angel investing
- LRLenny Rachitsky
I believe you do full-time. Would you say that it's your full-time gig now?
- RHRyan Hoover
Yeah. Yeah, it is. Yeah, I spending all my time there and yeah.
- LRLenny Rachitsky
Cool. So from what I can tell, the weekend fund is killing it. I'm not an LP, but it feels like it's kind of this underrated juggernaut that's just doing very well. And so I wanted to ask you a couple questions along these lines. One is-
- RHRyan Hoover
Mm-hmm.
- LRLenny Rachitsky
... what have you learned about investing, angel investing? Especially what's most surprised you?
- RHRyan Hoover
I mean, I feel like there's a lot, lot we've learned. So there's, there's things on the operational side. This is a whole category of, of, um, like running a fund. There's a bunch of things that go into it from LP communications, LP fundraising. There's also, like Wenedica who works with me on the fund side, she, um, she describes it as like hygiene. There's also good hygiene when it comes to running a fund. For example, you know, when you meet a founder, you should get back to them. (laughs) Like if it's a pass, you should let them know. And then there's a lot of different ways that you can do that. Some people, you know, might just say like, "Pass," and that's not very like encouraging to a founder if they like give you no context, no details. There's also an element of hygiene, which is we always follow up with the person that introduced us to that company, and we just feel it's kind of like that's what we appreciate. Like, we like to kind of know what happened, like have them close the loop. And so it's like good hygiene, operational things that we've learned and kind of honed over, over the years. I mean, the biggest surprise ... The biggest surprise has probably been ... I gotta be careful of how this is interpreted in some ways, but it's there are cases when I didn't think the company would make it. I, uh ... Either the product wasn't working and, you know, many months had passed and it was very clear that they, they ... Well, to me, I thought it was clear that, okay, th- this probably isn't gonna work out. In my head I kind of wrote it off. And then that company either pivoted or, or some m- like massive partnership or M&A kind of event came through out of nowhere. And so I g- I guess the learning is like never count a portfolio company out until it's over. And you know, that relies on, of course, backing founders that are very resilient and creative and, and, um, you know, driven to, to create momentum, you know, out of nothing. But, but that's been surprising to me and it makes me kind of excited because, you know, we've invested in over 110 companies now and, uh, it's, it's fun to be able to kind of see behind the scenes a little bit, how all these things kind of play out, both the good and the bad.
- LRLenny Rachitsky
That's such an inspiring takeaway. Does that change how you invest? Like to me that's like, all right, I guess I should just take more bets on founders that are awesome, although I find just founder bets, it's like a very expensive hobby/approach-
- RHRyan Hoover
Mm-hmm.
- LRLenny Rachitsky
... because there's so, there's so many great founders. How has that informed-
- RHRyan Hoover
Mm-hmm.
- LRLenny Rachitsky
... how you invest seeing that happen?
- RHRyan Hoover
I would say we don't, we don't have like um ... It's again my cop out, it's contextual kind of answer, like you know, some people are like, "We are a team first only." Some are, "We're market first." Some are, "We're product first." And we, we look at everything kind of holistically and I think the evaluation of the product is, is sort of a reflection on the team. So-... our, our assessment of the thinking behind the product that they built today and maybe some of the traction is a reflection on, like, the team's abilities and, like, the thought processes. So we try to look at it holistically and, um, I mean, yeah. I mean, every investor would say like, "Yeah, we wanna back, you know, resilient founders that are very driven and insightful," and all those things, of course. But it's also sometimes hard to, like, fully evaluate that unless you really know that person, so. So we try to, to take as much data around, like, how the product is working, how they made those decisions leading up to this to, to evaluate the team sort of indirectly.
- LRLenny Rachitsky
That's kinda what I've started to do, is I, I try not to invest as a founder bet unless I just know them because it's just so hard otherwise.
- RHRyan Hoover
Yeah. Yeah. There, there's a few founder bets that, that we've made. One, going back to the consumer social kind of thing, he's someone that I've known for, uh, many, many years. One of the most talented, like, designers, engineers, product builders, um. And I've just been waiting for him to start a company and, and so that was, that was one of those I'm gonna bet on you because I believe in you. I'm not sure about this first idea. Um, you know, who am I to judge? But I don't know if that's gonna be it. (laughs) But he's probably gonna launch 10 apps, and the 11th is gonna be
- 1:02:12 – 1:09:37
Advice for folks wanting to get into angel investing
- RHRyan Hoover
a massive success. And so that's sort of the way I think about those consumer social founder first bets.
- LRLenny Rachitsky
I love that. Last question along these lines. For someone that's hoping to get into investing or angel investing in the near future, do you have any advice for folks around that?
- RHRyan Hoover
Yeah. I actually, um, wrote a tweet story and, like, converted it to a blog post on this 'cause we've been, gotten a lot of... You probably as well, get a lot of emails or people saying, "Hey, I'm thinking about raising a fund." Like, "How should I do that?" Or, "I wanna get into, into venture. I wanna start investing." Like, "What advice do you have?" So yeah, I wrote a blog post on this, and there's many different ways to invest. There's, you know, angel investing is one. So great thing about that is if you have the capital to angel invest, you can do it today, tomorrow. Like, you, there's, there's no, no sign-offs required. You have maximum flexibility. But of course, you need to have disposable income. You need to be able to... You will need to lose all of it, and then hopefully, ya- you'll make... You'll be on the other side of that and make some money in 10 years. It takes a long time. There's scouting. That's another opportunity. There are more and more scout funds probably than ever before right now in different flavors. Some of them are, like, dedicated kind of scout programs where you have capital to deploy on your own. Some are more like, um, you still need approval, but you send the deals and you get carry on those deals in many cases. Those have pros and cons too. Like, they're easier to start and get into than raising a fund typically for most people, but you also are sort of reliant on that, that program or, or that fund. Um, you might have less autonomy in what you can invest in and what you can't. And then there's a few others. There's SPVs is, is one angle, which works really well for a lot of people. So, um, for those that maybe don't know, uh, on listening to this right now, SPVs are essentially like a single vehicle, um, investment into one company. So you raise money from LPs, from other investors, to invest in this specific company. And there are a few great things about that, like one, you get deal by deal carry, meaning, like the, the outcome of that company is, is you get paid when they exit essentially, assuming there's a positive outcome. Versus a fund, you have to, like, return the entire fund first. Two, it allows you to also bring in maybe very strategic helpful people into that particular round for that company, which can actually be a, a strong value add for that founder. The biggest trade-off is it's a lot of work sometimes. You, you have to basically do a fundraiser every company you invest in, and that's super time-consuming for a lot of people. And then the last thing is, like, ra- raising a fund. 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, and there's a lot more responsibility in managing funds and so on and so forth. But it provided me with the most flexibility in, uh, in a way to deploy many checks into many companies, especially when I didn't and still don't have, like, a ton of money to angel invest. So, um, so I mean, those are, like, different options. Like I, I think my blog post goes into more, like, pros and cons for each of those things. But, uh, the last thing I'll say actually is let's say none of those are really an option. You, you, you don't wanna start a fund, you don't have enough relationships to do SPVs, you... For whatever reason, you can't do a scout, you don't have an- money to angel invest. One thing you can also do is just, like, pretend angel invest. (laughs) 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. And this is what Vedika before she joined, joined me was doing to some extent. She was writing memos about companies she was excited about. And in some ways she was, like, doing the job before getting the job, and anyone can do that n- today. And that can be helpful too if you're applying or trying to prove your, your, your abilities. You can say, "Hey, here are the memos. Here are the companies that I would have invested in, you know, if I had the opportunity. And, you know, here's my thought process behind that."
- LRLenny Rachitsky
I love that. I'm curious about the logistics of knowing the prices of all these startups. But anyway, we don't have to get into all that. That's an awesome idea. I've seen people on Twitter-
- RHRyan Hoover
Yeah.
- LRLenny Rachitsky
... do that too. What... Where do you think this all goes for you? Are you thinking of increasing the fund? This is basically a last question, just, yeah, what's-
- RHRyan Hoover
Mm-hmm.
- LRLenny Rachitsky
... what's the future of Ryan, Ryan Hoover at this point as far as you know?
- RHRyan Hoover
Yeah. Still, still figuring out the meaning of life, uh, as we established earlier.
- LRLenny Rachitsky
I thought we cracked that one.
- RHRyan Hoover
Yeah. Yeah. I'll let you know when I figure it out. Um.
- LRLenny Rachitsky
Okay.
- RHRyan Hoover
(laughs) Um, yeah, we're on our third fund right now. We're actually about 30, 35% deployed, so we have plenty of, of capital. We're not gonna be raising anytime soon. And yeah, we're just investing in early stage companies right now, but when I fast-forward, like, longer term, I don't know. Um, I, I will always be investing. I'm also more of a fan of maintaining a smaller fund. Our latest fund is 21 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 f- like, really collaborative. We can write smaller checks. We can fit into competitive deals. I think it's a better product for founders. Like, we're not trying to take the entire round.We can, you know, try to bring on the Lennys of the world as co-investors, things like that. And so, investing will always be a part of my future, but I also love building. Building is, is the most fun. So creating something is, whether it's a company, I don't know, I don't know what it is, I'm not gonna even call it a company, but building something is hopefully in my future. I just got to figure out the right idea. And maybe, maybe reflect on your blog post too, uh, on the idea generation stuff that you shared, 'cause that, that is helpful.
- LRLenny Rachitsky
As long as you let me invest, all is good.
- RHRyan Hoover
(laughs) Yeah. Well, I don't know, I don't know if I'll ... Part of me is like, do I ever want to raise from venture? Now, it depends on the idea. If, if I need it, if it's required strategically, then yes. But to be quite honest, maybe I shouldn't say this, like, I'm kind of really interested in, like, just owning something 100%. And you can always raise venture later. Like, it's, it's a one-way door. So I kind of want to delay that door, you know, for whatever I build next, if I can.
- LRLenny Rachitsky
I 100% get that. That's how life is with this newsletter operation, and I highly recommend it.
- RHRyan Hoover
Yeah.
- LRLenny Rachitsky
If you can pull it off.
- RHRyan Hoover
Yeah.
- LRLenny Rachitsky
Okay. I am ... That's it. Just a couple, just where can people find you online? It's kind of a dumb question 'cause you're very easy to find, but where do people go to learn more if they want to reach out and then, and then how can listeners be useful to you?
- RHRyan Hoover
Yeah, I'm just, uh, easy to find. @rrhoover on Twitter, ryanhoover.me is a simple website, um, have a bunch of old blog posts on there. Probably with a bunch of broken links and broken images, but it's, it's there, the content's there. I don't know. I'm, we're, we're investing, we're investing in early stage companies, B2B, B2C. If you're building something weird, I don't know, DM me, email me, I'm around.
- LRLenny Rachitsky
Amazing. Ryan, thank you so much for being here. It's kind of a surreal experience interviewing you, and I'm really honored that you came, and I can't wait for people to hear this. I'm really happy about all the nuggets that I was able to extract out of your head, and thank you for sharing them. Thanks for being here.
- RHRyan Hoover
Yeah. Thanks, Lenny. Yeah, these, these conversations are, are helpful in, like, reflecting on, on what do I actually believe anyway. So it's, it's just like writing, it's helpful.
- LRLenny Rachitsky
And it is just as helpful to everybody else. So thank you again.
- RHRyan Hoover
Cool. Thanks, Lenny.
- LRLenny Rachitsky
(instrumental music) Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.
Episode duration: 1:09:37
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