How to launch and grow your product | Ryan Hoover of Product Hunt and Weekend Fund

00:00I don't know how to articulate that feeling, but that flutter in your stomach that you wake up with in the morning of just anxiety and stress and worry. Being a CEO or a founder makes it slightly harder in some ways because you still have to put on this mask. You have to put on the space of confidence externally 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.

00:29Ryan 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.

00:53Hey 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 see you do the podcast now. It's cool.

01:01Thank you, man. That compliment will go straight to my heart and I will think about it often. I appreciate that.

01:07Cut that and put it on Twitter. There you go. Yeah.

01:09That's the clip. We're done.

01:11Yeah. Podcast over.

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02:13Hey Ashley, head of marketing at Flatfile, how many B2B, SaaS companies would you estimate need to import CSV files from their customers?

02:21At least 40%.

02:23And how many of them screw that up and what happens when they do?

02:26Well, when based on our data, about a third of people will consider switching to another company after just one bad experience during onboarding. So if your CSV importer doesn't work right, which is super common considering customer files are chocked full of unexpected data and formatting, they'll leave.

02:47I am 0% surprised to hear that. I've consistently seen that improving onboarding is one of the highest leverage opportunities for both sign-up conversion and increasing long-term retention. Getting people to your aha moment more quickly and reliably is so incredibly important.

03:00Totally. It's incredible to see how our customers like Square, Spotify and Zora are able to grow their businesses on top of Flatfile. It's because flawless data onboarding acts like a catalyst to get them and their customers where they need to go faster.

03:17If you'd like to learn more or get started, check out Flatfile at flatfile.com/Lenny. 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 a super awkward or super hilarious moment of that?

03:37Yeah, so Product Hunt started in late 2013 and quickly got a lot of traction in the tech sphere. So yeah, people in tech might recognize me. People outside of tech, doubt they recognize me. I actually do wonder subconsciously if I grew my hair out to avoid being recognized. 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 disappear sometimes. But in San Francisco where everybody's in tech, there's a lot of that and probably the moment where I was like, oh, this is a thing, it was probably early Product Hunt. I was at... I don't know.

04:15If you know this, do you know a club called DNA Lounge and they did something called Booty every Saturday. It was like a mashup dance party.

04:23Yep.

04:23Yeah. Super well known in the Bay Area. Really fun kind of experience. Anyway, I remember being with friends and drinking like one does, and somebody turns around and says, "Is that the Product Hunt guy?" That was the first time that sort of happened in that setting where I was like, oh gosh, now I have to think about my actions and I can't just be entirely loose and relax with my friends. And so anyway, there's always pros and cons in those types of things, but it definitely makes you more aware. I'm already a very sometimes anxious and self-aware person in terms of my surroundings.

04:58And 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.

05:05I've actually gotten a little bit through that same experience recently in a much smaller sense where with this newsletter and the growth of this thing, there's meetups happening all over the world, and so I've been going to the SF meetups here and there, and it feels very strange to be known and people, they've taken pictures of me, what the hell's going on? I started this thing as Covid hit and it was like everyone's at home, I was just typing on my computer, don't have to go anywhere. And as the world has emerged, it's become a new thing I'm dealing with on a much smaller scale.

05:37Events are fun. We threw a bunch of them at Product Hunt and yeah, you do a lot of selfies and a lot of handshakes and there's some energy there. I'm an introvert though, so by hour three or four I'm just like, I need to use the restroom because I haven't been able to escape and I'm socially exhausted, but they are fun.

05:56I know exactly what you mean. I am also an introvert and I get so drained doing things like that. I was going to ask you about that. So yeah, along the same lines, 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?

06:12Yeah, you're right. I probably maybe overshare on Twitter and other things.

06:17No, that is not what I'm saying.

06:18There is a list of... No, no, I know what you're saying. But there's also a whole series of things that I don't talk about. Well anyway, I won't talk about the things I can't talk about, but one thing that-

06:18Shoot.

06:31... most people don't know about... I know, there's certain juicy things like everybody has in their life. I recently moved to, well I guess it's been a year, I moved to Miami about a year ago and 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. I don't know. There's no benefit or reason for me to do so. 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. That said, in Miami, we're there about two-thirds of the year, so I'm actually in California right now as the summer humidity comes through Miami and hurricane season.

07:10We're planning to do more of a, I wouldn't call it nomadic and I wouldn't call it bi-coastal per se, but something like that where two-thirds of the year were in Miami and maybe a third were in New York or L.A. or some place else. And I love that. Fortunately we have the flexibility. When I say we, my girlfriend, Susie and I, to just carry our laptops and work anywhere. So it's been a nice lifestyle kind of shift.

07:35I did not know that. That is very interesting. Why did you get pulled into Miami? What pulls you there?

07:40Yeah, so the way I describe... Cities are kind of like a product. So if you're in a supermarket, or supermarket, I sound like an old person. If you're in a store, you're looking at different products, if you're online, you're evaluating different products, and they each have a cost and they have some benefits or values or whatever you want to use to describe it. And for me, each city is kind of like that. And so in terms of cost, there's cost of living in terms of housing, 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 things like that. And so I was in Bay Area for 10 years, L.A. for two, Miami for one now.

08:19They 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 lots of it. It's just cheaper. It's cheaper than the Bay Area. It's cheaper than L.A., when you kind of count all in costs. We had a bunch of friends move there. So we enjoyed the city. We're like, this is good, strong ROI, this is a good product, let's move there. But at the same time, as I mentioned, we are traveling and exploring other cities, so it's kind of the best of both worlds for us.

08:54Very cool. Curious how long you last there and how you like it over time? I love Miami. I always have a good time when I go there and I have many friends living there. 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 offered 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 because this is such a cool offer, and what have you learned going through this and hearing people's questions?

09:26I first opened up my DMs, I had them closed, which is traditionally the default 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 go through. I opened it up quietly and actually didn't get a lot of spam surprisingly. Yeah, people would sell something or promote something, but it wasn't too bad. So I left it open and then I forget one day maybe I was on the elliptical bike or recumbent bike or something and I was just like, I tend to get on the bike and just hold my phone up and just do emails and work.

09:57And so I just said, "Hey, DM me if you have any question, any founders, and I'll try and answer as many as I can." And 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, 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 inspired by any topic. It's sort of like a writer's block. And so I found this also kind of as a means to do almost like micro blog posts in a way, where the prompt is the question from somebody else. I don't have to think about the prompt.

10:34And then the answer is in some ways a way for me to actually think about that topic. Almost refine my own thinking in some sense. And so I started doing that and 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 summarize their answer. Of course, keeping anonymous, not sharing anything that would be sensitive and just put it on Twitter and it's been fun. I do that maybe once every three or four days I share a new question and answer and it's like micro blogging in a way. I guess that's what Twitter is, but it's kind of like a real micro blogging activity for me.

11:16Is there anything that's 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?

11:24I wouldn't say anything 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 going to ask certain things 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, we have three months runway left, we're running out of money. Here's a situation. What advice do you have?" Or just things that everyone has to wear this unfortunate mask is what I use to describe it, this mask in life and business where everything is going great and you're super confident, there are no problems.

11:59You got it all under control. And so the reality is that's not the case. If you peered inside of almost every single company, it probably looks chaotic in different ways. And so I guess maybe the biggest surprise or thing that I value the most is the authenticity of people willing to share some of these vulnerable moments and questions.

12:17Awesome. 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 think is part of the reason it worked, is it's based on people asking me a question and then I answer the question.

12:28Yeah, it's true.

12:29And that ends up forcing you to have concrete actionable advice. So you've kind of developed an even more interesting way of doing it on Twitter where it's more focused. So very smart.

12:39I've always liked your format by the way, in that you are a curator in many sense. You have a lot of experience and good ideas, but you're not trying to answer all the questions. In that, you are really pulling in experts in their domain expertise to find answers or inspiration. And I've always liked that format because one, it, I think, leads to better results, better content, better answers, but also it's arguably easier. Imagine if you tried to write... Well, you're shaking your head almost like maybe it's not as easy.

13:11If I had the answers, I'd be like, oh, here you go, I'm done. The research takes a lot of work and time, but I do agree it ends up being a lot more useful and valuable. 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, 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, what does everyone do and what seems to be the pattern of the thing that works?

13:41And that kind of led to this approach and it takes a lot of time, especially this new series that we're going to chat a bit about that I worked on where it's just endless interviews and chats and researches and watching interviews. But yeah, it works out.

13:55Yeah. How many hours actually do you put into a typical essay?

13:59Oh, reverse question. I would say the median-

14:02Yeah, I don't know if I'm supposed to ask you questions, but I'm curious.

14:05Banned. No, it's cool. I'd say the median post is about 10 hours. I kind of work on it through the week, so maybe a few days through the week. But the most epic posts take hundreds and hundreds of hours that I work on behind the scenes as I work on the weekly posts. So there's a wide range. Some posts take like three hours, and sometimes those do very well. Much better than expected.

14:31Yeah. Yeah, that's exactly going back to my point about it takes a long time to write content that you're proud of. I'm also just very particular about words for better or worse. And so the first draft actually is maybe 20 or 30% of the time, and then the rest is refining it and getting feedback and everything else.

14:49That's exactly how I find it. Question I wanted to ask is, startups are so freaking hard, they almost always fail. It's always just like, oh my God, why am I doing this to myself? My general advice to founders is don't start a company unless you just 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? How should I approach this?

15:16Yeah, I do spend time, ironically challenging founders sometimes when they're thinking about raising or thinking about an idea to not raise. I think people who are in tech, 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 gone through some pretty massive bull cycles where that was possible for a lot of people, but it's a huge decision. So with Product Hunt, it was a side project in the beginning, it wasn't actually intended to be a startup at all. But in the beginning 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.

15:54So it was during that time I was really just thoughtful around should we raise, do I want to work on this for many, many years? What's the opportunity? Is this even a venture-backable idea? All those questions were circulating in my mind for a while. And this was also in a time when the market was similarly bullish. This is end of 2013, early 2014, and investors were using Product Hunt to reach out to me. They were sort of courting me and doing that old song and dance to invest, but I just wasn't sure if I wanted to. And so I don't know, I think a lot of those decisions are very personal and contextual.

16:33However, 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. 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'll probably fail before then 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? Am I really stoked to work on this for many, many years? But then 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.

17:06And Product Hunt, we called it, not even a side project, we call it an experiment. And that framing I think for me has always been helpful because 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 see if people want this thing and then kind of adapt. And so an experimental mindset is helpful. And I think a valuable way to start, it even goes back to why running the Weekend Fund. It's like what are you tinkering with on the weekends and how can you be more curious and experimental in your exploration of new startup ideas?

17:45I 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?

17:50It had multiple meetings. Yeah, it was three meetings. One was that, I started Weekend Fund when I was building Product Hunt, so took a lot of pitches and calls with founders on the weekends. Two, I think a lot of great ideas start by metaphorically speaking nights and weekends, side projects or ideation. And then the third reason was it was more friendly. I don't know, I didn't want to name it Hoover Capital or something like sterile, I wanted it to be-

18:15Wait, that's an awesome name. Hoover Capital. Wow.

18:19Hoover Capital? I don't know. I feel-

18:24Yeah, it's not on brand.

18:28Yeah, not for me.

18:29But it's powerful. As you know I asked people on Twitter what questions they would want to ask you. And so I'm going to inter-splice these questions as we go through this. And you just touched on-

18:29Cool.

18:37... Product Hunt and fundraising, and I'm curious, if you were to go back and do it again, would you raise money for Product Hunt or would you not?

18:45Great question. So at the time, this is also the thing I asked founders is why do you need to raise money? What is it for? And surprisingly, some people are like, I don't know. They don't have a clear answer. For me, it was pretty obvious. We needed to hire, we needed people. I didn't have personal capital to pay people. There was an alternative reality where we actually built it open source. I was thinking like, is that possible? 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's really hard to do.

19:20And when you're building a company, you probably don't want to innovate on too many things, including essentially how to build a product and build a team. So anyway, to answer your question, at the time raising money was the right decision because I wanted to hire and I didn't have personal capital. There really weren't 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 maybe a year of development with this very small team.

19:52So 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 doesn't have direct competitors in the sense of an Uber and Lyft situation where raising is actually kind of mandatory and you sort of have to build a massive war chest to compete. So there is a scenario where if I had more money, then maybe I wouldn't have raised venture capital. But yeah, there's a lot of other decisions and other things that probably bigger mistakes I think I made. Not that raising money was a mistake by any means, I just think the right decision meant.

20:29But yeah, there's a lot of learnings and hindsight's 2020.

20:32The point you made about you just needed money to run the thing, I think that's so overlooked when people bash the idea of fundraising for a startup that maybe didn't need it. You just need money. 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 going to go.

20:53I think it's very important to raise from people who are aligned with you too. Meaning why does this person want to, whether it's an angel or a fund, invest in your fund? I'm sorry, not fund, your company?

21:06When you go down a certain path, when you've raised a series A, B, C, like you have different expectations when you raise your pre-seed or seed round. So I think also understanding what you're signing up for is super important.

21:19What kind of treadmill you're getting on.

21:21Yes. Yeah. Because you can't get off. I mean you can, but it's not like a company. I always say when you're at a company, you could put in two weeks notice, one month notice, you can move on. As a founder or a CEO, you really can't. Now you technically can, but you can't. It's really hard to exit.

21:41Yeah, I look at the Airbnb founders who've been doing this for 15 years and they're doing well in life, but it's very hard to leave. Coming back to Product Hunt. People launch their product on Product Hunt and that's the thing. And I'm curious, founders are always so obsessed with launching and the power of a launch and we got to 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?

22:10Yeah, whenever I share my perspective on stuff, I unfortunately I'm always like it kind of depends, which sounds like a cop out answer. So my answers are usually more nuanced. And the thing about launching is going back to why are you raising money? What's the goal? Same thing. Why are you launching? And a lot of people default to things like customer acquisition. Oh, I want to acquire customers. But sometimes it's not useful. Launch sometimes doesn't help with that, but there are many other reasons why you might want to launch. So customer acquisition is one, to get the word out. Another can be recruiting.

22:45So by sharing your story, getting people excited, it might make it easier to recruit and get people excited about what you're building. Another is fundraising. Sometimes it can create momentum. As other investors, they do read the news and they know that when this company is more public, there might be more heat around a particular deal. Feedback is one. Feedback from users, feedback just serendipitously. And 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 what are the priorities in the business? It might not be customer acquisition at all.

23:23It might be that we need to recruit and hire, let's launch so we can get the word out. Hopefully that will help land our next engineers, designers or whoever. And then I will also say there's these little side benefits too of launching that we see a lot through Product Hunt. One of them is team morale. And 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 the likes on Twitter and the votes on Product Hunt, but there is a powerful team morale and building moment there where you can all celebrate what you've accomplished and what you've built and put it out to the world.

24:03And somebody on the team could share the Product Hunt launch or some TechCrunch article with their mom. And 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 SEO is a part of your strategy. Having articles, positive articles, having a positive Product Hunt launch, things like that can also be helpful.

24:25That's awesome. I love that last point about morale, 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 seen or been, I don't know, an observer of, if that makes any sense?

24:42I should look at our database on Product Hunt and see how many launches we've had because it's going to be a subset of that. By seeing, some of it's very high level, but tens of thousands over the years.

24:52Okay. 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 founders miss with how they launch?

25:05Yeah, this goes back to college, and I won't go on my own rant about education, but 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. So 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. The way that I kind of describe a frame of writing, maybe your tagline for Product Hunt or for your launch in general, is 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 when you're just hanging out?

25:46How 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 vague language, it just doesn't click. People are sick of the PR speech.

26:02And so I think the language and the microcopy copywriting matters so much. And then there's a lot of other things around we should go more to the product and less about the launch. Do you really understand who you're building for and do you understand how to communicate the value prop? Where does it fit in the mind of the user? There's sort of a lot of, I guess, more strategic decisions that go into that before the launch.

26:27I imagine each of those points can be its own podcast and blog post. One of the questions that people asked me on Twitter was the classic, how do I get to number one on Product Hunt? So my question to you is, I know there's not going to be a silver bullet, is there 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 got to get right?

26:50Yeah. So in the post flow there's actually links to a bunch of guides and FAQs and things like that. So it's really easy to find the best practices there. The team also has this checklist. So once you launch, there's a checklist of things, recommendations or tips. And I'm actually forgetting 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 who usually people tend to add some introduction, some context. Generally a lot of people they manufacture PR speak there too. And so speaking more like a human I think is important.

27:30Also keeping it a little brief. Some people write essays, which might be interesting, but the reality is most consumers, especially people on Product Hunt, 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 an essay from the maker. So keeping that short I think is helpful. And then another big one is the gallery is often the first thing that someone is going to see once they land on the page. And so just naturally our eyes gravitate towards visuals.

28:00And 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 communicating 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. There's many different ways to approach it, but a very clean, visually interesting story can also be a great way to capture people's interest in what you built.

28:27Awesome. That was very tactical and helpful. If you were to launch some on Product Hunt yourself and it wasn't hunted by Ryan Hoover, do you think you would get to the top?

28:38I don't know. It's funny because we should do some historical analysis on Product Hunt. I'd be curious to know the actual numbers. But it varies all over the board. So some people they ask me, "Hey, I don't know, is Product Hunt, do B2B companies do well there?" And I'm like, "Yeah, probably more B2B companies than B2C companies actually." And so you see seemingly boring companies that tap into something that people find useful or resonates with them can go to the top. And then you also see the weird wacky stuff. The silly apps also hit the top. So I don't know, it really varies. And sometimes it's also driven by almost like the zeitgeist. What do people find interesting right now?

29:24What'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 zeitgeist of the early adopter tech community. What are they interested in? What do they find compelling in general?

29:41Got it. Okay. So I have a bunch of questions from Twitter that people wanted to ask you. 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 where this goes. Jessica Toy, she's a PM at Angel List, she's actually a friend. We worked together at Airbnb. She asked a great question.

29:59Yeah, Jess is awesome. Shout out to Jess. She's been super helpful on the Angel List side, so she's awesome.

30:05Amazing. Okay, she's the best. She asked what you learned as a PM that has helped you in your venture career?

30:12So my background is marketing and then product management pretty quickly. Used to work in the gaming industry, which is I think an awesome industry. Really hard to make it in that industry, but amazing place to learn. And I think product, I don't know, I have so many biases, so I have to be cautious of that. But having a product background I think is one of the most important aspects of early-stage start of 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 comes down to the product that you're building.

30:45And so I think having a product management or product background is helpful in one, having more, I guess, perspective and evaluating different ideas, and arguably more important, how the founder thinks about things. So it might be less about me evaluating the market need for this particular idea, but it's what's the thought process and how 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's more opportunity to create some sort of impact or help shape the product in a slight way.

31:27Awesome. Basically, if you're a PM, you've got a lot of the skills that you need to be a founder.

31:30Founder, and arguably investor as well.

31:34That's right. Okay, so Leo of Susa Ventures, who's also an awesome dude, he asked if you could back and-

31:41I saw Leo in Miami-

31:44Oh, you did?

31:44... not too long ago.

31:45Oh man. Oh yeah, he moved to Miami too. Oh my God. Everyone's over there. Okay, so 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?

32:01Yeah, I've been thinking a lot about this actually lately. And yeah, 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 an ambition to expand beyond tech into all different types of categories of products. So we experimented with podcasts, actually podcast discovery. We experimented with video game discovery, we experimented with book discovery. And the thesis there was, okay, this could be actually 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.

32:38One, the product experience and product 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 products out there. And two, it's really difficult to translate a committee and expand into other communities. Some have done it like Reddit is maybe a great example, where Reddit has this massive long tail of every kind of community you can imagine, but very few companies and platforms can actually do that. 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 better and with more things, which is effectively what we're doing now.

33:18Another regret, another thing I would've changed is I would've actually tried to monetize and generate a revenue sooner. We raised a seed in a 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 everything you prioritize is at the cost of something else. 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.

33:50But what I really should have done is dedicated maybe 10% of our focus on revenue generation, because once we started generate 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. So if we would've started in 2014 to make some money, we could have been cashflow breakeven maybe 2015, 2016, which would've just given us a lot of flexibility in owning our own destiny and proving out some of the business model itself. And then the last thing, because I've been thinking about this lately, is delegation is a classic founder challenge. I am just generally a controlling person.

34:29It'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 said, we had amazing team. I worked with some amazing people, still people that are at Product Hunt today, six, seven years later. It wasn't anything about the skills of the team, it was just my own trust and my own delegation. And what I shouldn't have done is up until shortly before I left, I was editing the newsletter every morning, for example. Every morning I was waking up 5:00 A.M., 5:30 A.M. editing the newsletter. And that's just kind of silly to be doing that so many years later after starting.

35:09I totally get that drive to just make sure everything you're putting out and that your company's putting out is top-notch. I have the same feeling and it is hard to let go and just like, that's not perfect, but I'm going to be okay with that. I'll do other things.

35:24Yeah, it's really hard. And I think it's a tendency that is, in some ways 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 almost OCD like 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 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, just to [inaudible 00:35:59] your company anyway.

36:01It'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, but that you're also happy about to have gone through?

36:12Yeah, yeah. Actually I recently in the past couple of weeks wrote a blog posts that I'm not really able to publish. Basically there's certain things I want to share that it can make things challenging and complicated for others. So I don't want to put anyone else in a pickle, so someday maybe I'll publish this post. But to speak more vaguely about it, there are some really hard times in Product Hunt we have all faced in different ways as founders, or not even just as founders, just as people. But yeah, there's sometimes where I felt physically ill, many different moments in Product Hunt, and it was just really tough.

36:46And I don't know how to articulate that feeling, but that flutter in your stomach that you wake up with in the morning of just anxiety and stress and worry. Being a CEO or a founder makes it slightly harder in some ways because you still have to put on this mask, you have to put on this space of confidence externally 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. So it's a struggle because I think, I don't know, I value authenticity so much and I kind of thrive around people who are authentic.

37:20However, there is this tension 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 I've, 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 skin for certain things and just provided more perspective into the company building journey.

37:49Okay, 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 a hat and socks and a few other things. And you also get a one-year free subscription to my newsletter and even a goody 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 to make sure you apply by August 14th, 2022.

38:31Again, the URL is Lennyspodcast.com/bonanza.

38:36And 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 wouldn't change, wouldn't undo that, right?

38:50Yeah, yeah. It's kind of like a lot of things. What doesn't break you makes you stronger to some extent. So it didn't break me, it just scarred me a little bit, but it didn't break me.

38:59And turned you into the Ryan Hoover that we have today.

39:02For better or worse.

39:04Maybe one last question from Twitter and Twitter Roddies, from Sandeep. He just wanted to know 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?

39:16Yeah, still figuring it out. I'm still asking the old stereotypical questions like, what the heck is the meaning of life? What am I here for? All those things.

39:26Let me know when you figure it out.

39:28Yeah. And maybe there is no answer. Maybe the question is actually doesn't matter. So if I'm honest, I'm still figuring all those things out. I think 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, I don't know, they just matter so much I think. And the older I get too, I don't know, I care less about having a lot of friends and more about a few deep close relationships.

39:56And I don't know, I feel like that's very different than middle school Ryan, or when you're on the playground, metaphorically speaking, where everyone's trying to be popular and meet a lot of people, and even joining and being in San Francisco in the tech community, you want to meet a lot of people and network and do all those things. That's less interesting to me and less important.

40:18And then more on the business side, the thing I've been thinking about is, 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 high momentum leads to more high momentum, low momentum leads to more low momentum, because there's this energy 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.

40:50It might lead other people to feel less motivated or care less. And so, I don't know, momentum is this weird thing that arguably it's one of the most important things in early stage startups. And of course it's an input to a lot of things, but it's just so important to nail.

41:08Marc Andreessen talks about that last point, that there's 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 an investor, 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.

41:32Yeah, that's a really good point. It also mirrors with the power law of investing, where in most people's situation, its one company is returning... You can invest in 100 companies, one of those companies is probably going to return three to five X in the returns of all the others, maybe combined in some cases. So it's wild.

41:53On the first point that you made earlier about cliches and platitudes, reminds me Michael Paulin and has this point that he makes that cliches and platitudes are cliches and platitudes because we've heard them so many times, but that because they're true. People just say them because they're so true. And as much as we don't want to hear them, there's a reason that we hear them again and again. 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.

41:53Yes.

42:22Okay. People have figured that out. But it was like, I feel that. I feel that right now. But it's true. That's why we're like, okay, shut up. I heard that, that's in a song.

42:33I was listening to a podcast about someone who is basically describing psychedelics as a gateway into meditation and everything, and how it could be one of those things that makes people... A lot of people who take psychedelics come across as another hippie cliche person who repeats the same things we've all heard many, many times. But there's a reason why there's a pattern there. And he describes psychedelics as one way to feel that and learn that feeling that you can achieve with meditation, with experience.

43:03Yeah, I think Sam Harris talks about this where you could either meditate for five, 10 years to work your way up the mountain towards enlightenment, or you could just take some psychedelics, visit it for a little moment, see what it's like, and then be motivated to work on getting there more naturally. This is a good time to play a little game that I invented just for you. Okay, so you're the founder-

43:03All right.

43:26... Product Hunt and on Product Hunt, people up-vote ideas that they like best. And so what I'm going to do is I'm going to give you two options and you tell me which you'd up-vote and it'll make sense once we get going. That sound good?

43:40Okay, cool. Let's do it.

43:42Okay. TikTok or Instagram Reels?

43:45And in context setting, are these within the context of products I like and know?

43:51Products you would choose to use that you like better. Yeah, not like, which will better business. Yeah.

43:57Okay. Okay, got it. TikTok for me. It's funny, Reels I kind of joke with Susie, my girlfriend. I joke that Reels is like TikTok but two weeks late. It's not entirely true, but I feel like I see a lot of TikTok videos on Instagram Reels weeks after they've been published.

44:15We'll see. I have some friends that work on Reels and I'm excited to see where they go. Okay, next. LaCroix or Topo Chico.

44:22Ooh, this is a tough one because I am generally a LaCroix kind of person, but Topo Chico, I like the bottle. So when Topo Chico is available, I'll go Topo Chico. I'm sorry, LaCroix.

44:33Totally get that. My wife's a huge Topo Chico fan. We have many bottles. They're beautiful. They've kind of changed a bit. They're super clear now. They used to have a little tint. Very important topics.

44:34Observant.

44:47Yeah. Okay, next up. Bay Area or Los Angeles?

44:51Los Angeles. Although it depends on my goals. If I was a new college grad or someone young and new in tech industry, definitely San Francisco. You'll create a lot of serendipity. You'll meet a lot of people. But from a lifestyle perspective, L.A. L.A., I just find more enjoyable, weather's better, there's hiking, housing is cheaper. So L.A. today, San Francisco 10 years ago.

45:16Very nuanced answer. I knew you were going to say L.A. and so next is East side L.A or West side L.A. ?

45:23I don't know. We lived in Hollywood up in the hills for a while, so I don't know if that's east or west, but wherever that is, big fan.

45:32I guess that's west, right? It's not near the water. That's a really good question. Hollywood Hills. All right. That'll be a third option. Okay. Electric bike or regular bike?

45:41Nothing against electric bikes, but I feel like if your goal is to get exercise, then just get a regular bike. But I don't have either. I have a recumbent bike at home that I use for exercise. And the reason why it's recumbent and not like a Peloton where you sit up is because I can do bills and work basically while I'm exercising.

46:00Wow. Very productive. Okay, next. Dark mode or light mode?

46:06Light mode. I've never used dark mode ever. Actually I take that back. TweetDeck is the only dark mode kind of app that I use. But-

46:15Wow.

46:15... I don't know. If a founder is prioritizing dark mode before they have product market fit too. It's like a big red flag for me. It's a little bit of a hot take. Some people are going to hate me for that, but I don't know. I don't think dark mode matters for 99% of people.

46:29Wow. Big hot take. What if they just go straight to dark and there's no light mode, does that count against them?

46:36Yeah, that's fine. As long as just one mode. It's the teams that prioritize all these small things that don't matter before the product is actually is useful for people. Or that is where my product manager hat comes in and I'm like, is this the highest on your priority list? I don't know. Now big asterisks, it's all contextual. Sometimes the audience you're building for really cares about dark mode. If you're building for developers, maybe you need dark mode or some version of it, but yeah, I'm light mode.

47:04Awesome. Okay. Did not expect that. Love it. Okay, two more. Wash the dish right away or let it soak in the sink.

47:12I'm looking at the sink over here right now. There might be dishes in there, so that'll be my answer. Yeah. Bad habit.

47:19No, I think there's power in letting it soak. I respect that.

47:22That's what I'll tell Susie next time. There's power. Lenny said there's power in soaked dishes.

47:27There's physics. It's soaking.

47:29Yeah.

47:29Okay, last one. Web3 or Web5?

47:30I don't know what happened to Web4. So I don't know, maybe I'm going to split the difference, I'm going to go Web4.

47:39Okay. We did it. That was the inaugural edition of which would you rather up-vote. Amazing.

47:44There you are.

47:45You killed it.

47:45I like this. All right. It's kind of fun. This could be a fun little segment, I think for a lot of things.

47:52Yeah, it'll plug Product Hunt. It'll be great. We'll see where this goes. Just replace my lightning round, which I experiment with. Okay, but actually I have other questions I want to get through before I let you go if that's cool?

48:02Cool.

48:03There's kind of two topics. One is around consumer startups and just a few things that I've been learning there. And then angel investing and then we wrap. 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 kick-starting and scaling and consumer business. And there's a few things I've learned there that I just wanted to get your take on. One is that, and we talked a bit about this, just like 99% of consumer apps seem to just not work, especially if they're venture scale, if they raise money. Just a reminder of how hard consumer is. When is the last consumer app that really took off?

48:40And so I just wanted to get your thoughts as what's your take there? What should founders do that are starting a consumer company?

48:47Yeah. Yeah, it's tough. Obviously consumer is pretty broad, so there's different levels of difficulty. I think consumer social or games, building games is probably 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 a B2B company. Historically, a lot of it's been advertising driven. And to do that you have to first get to massive scale for advertisers to really care. And then you have to double it and double it and double it again. So monetization is super tough. Versus a B2B company. It's like people have a problem, they have a need, they're willing to give you money on day one.

49:28The other thing about consumer that's tough is you're always fighting different... Essentially you're fighting for attention. And so you might be some consumer social company, but you're kind of competing with Netflix too, which isn't in your direct domain. But people could be watching Netflix or they could be using your product or 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 built-in habits, routines.

49:54This is a big, big part about consumers too, is eventually you want to be an internal trigger in someone's mind where they just without even thinking they go and use your product or services for some reason. Usually you'll start that way. You need external triggers to 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, other products? It's really, really hard.

50:15And then I think a lot of it is like B2B companies, usually you have a clear problem that you're solving and you can talk to customers, you can understand what are their current behaviors, 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 fuzzier. If you take Twitter and you even ask someone, why do you use Twitter? And people will have different answers that are all fuzzy and they ultimately tend to come down to some sort of innate human desire.

50:49For Twitter, it could be about I want to 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 the B2B company, it's super simple. It's 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 what it solves. And so B2B is easier just to navigate that idea maze. And so with consumer, your first blog post on this topic touches lot on the idea side, and a lot of it resonated with me, especially the insight piece. What is the insight that you as a founder have to build this thing?

51:30Because 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 a problem journal just when things annoyed me or when things were less efficient, I would write it down as a note and I didn't try to solve it. I didn't say, oh, here's the solution. I was just like, this is annoying. In San Francisco, one example is a lot of people don't have laundry in their unit, so I'm like, that's kind of annoying. That's a problem. Maybe there's a solution out there. So things like that, I don't know. There's a bunch of different ways.

52:06Your blog post does a better summary, I think, of the different ways different companies ideated and came up with their ideas. But yeah, many different ways to navigate it, but needs an insight of some sort.

52:16Awesome. I hadn't heard that problem journal idea. I was going to 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?

52:30Yeah. Yeah, the problem journal is one, and again, I think it's helpful not to try to come up with a solution, but just simply write down the problem you've observed or experienced. Another one I think is interesting is just to immerse yourself in different communities. Ideally maybe seemingly niche or weird long tail communities. It doesn't have to be that necessarily, but that might be where you'll see more unique insights or gather more unique insights. And you could do that through participating in some Reddit's. Meeting a lot of people who are really excited about some other thing. It could be some weird robotics like niche hobbyist community for example.

53:07And a lot of that I think will hone or just create serendipity for ideas. You might see patterns or you might see problem statements emerge from many people in that community that are facing similar things. And then there's the other component too, which is really about observing trends and changes, whether it's like a consumer behavior shift. Let's take an obvious one today is distributed working. So five years ago when the Weekend Fund started, that was one of our themes. I was like, I think distributed working will be on the rise for a number of reasons. One, it's harder and harder to recruit. Two, there's a subset of people who really value that flexibility and autonomy.

53:46And then fast-forward, we had Covid that accelerated remote working, and now that's a huge consumer behavior shift, not just in how people work, but also going to your Airbnb world. Airbnb has shifted their entire product to support more of this remote working kind of lifestyle. Just the way that the homepage is now, more of a catalog of places that you could explore at different times of the year, or maybe even before it was more like, I have a very specific vacation trip that I want to take during these days in these areas. It's a very different browsing kind of experience. So that's just one example. Consumer behavior shifts is one thing to observe. The other is technology shifts.

54:26So what new thing can you build today that could be built yesterday? And so there's a bunch of categories around there. Like Web3, AI. The biggest shift that we've seen is mobile in early 2010s that unlocked a whole bunch of things. So yeah, I think it's observing those shifts and those changes. Last thing I'll see on that is I think start-ups, since there are more and more people building companies and technology, there's essentially more efficiency. It's certainly not a super efficient market, but there is more efficiency in problem discovery and solution exploration. And so for that reason, you need even more reasons for things to... Sort of answers to the why now? What's changed?

55:09What insight do you have? Why doesn't this exist already? Because a bunch of people are trying to build something in this space most likely. So that's a lot of what we think about, especially on the investing side when we talk to founders.

55:21Wow, there's way too much good advice there. Have you written this down anywhere? Is there a tweet thread people can find your kind approach to coming up with an idea?

55:29I have not. I don't think so.

55:29Cool. All right.

55:29I'd be happy to have a blog post for the future.

55:36Or this is the content for people to save and use. 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 an insight that we both share is that it's really important to get really narrow with who you focus on initially as a startup. For founders, it's often so counterintuitive. It's like, oh my god, why should I focus on 1000 people or 10,000 type people versus the millions that might want to 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 how you're going after?

56:13Yeah, it's effectively the more narrow your idea generally, and this is where I throw in the big asterisks, 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 your messaging... When people land to your homepage, you don't need to create a broader value prop to everybody, but really you can focus on what is the problem this particular audience or community is facing.

56:49And so generally it's just easier. Now, there is always that challenge of like, well, is this too small? Is it too much of a niche if my goal is to build 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 eventually expand well beyond that. I'll go back to Airbnb, you know the story way better than I do, but initially it was just basically couches and extra rooms and houses. And a lot of people, most people in the US would not do that. My parents, not in a million years.

57:30Even me, I don't want to stay in some strangers room. I want my own space, my own house. So that probably at the time seemed really niche and small, but obviously they extended well beyond that. Now Airbnb is housing in generally speaking. Their [inaudible 00:57:47] housing, in my mind, which they haven't yet expanded into real estate sales or long-term rentals per se, but that's a possibility.

57:58This is a good segue to the last topic I wanted to touch on, investing, which I believe you do full-time. Would you say that it's your full-time gig now?

58:06Yeah. Yeah, it is. Yeah, spending all my time there. Yeah.

58:10Cool. 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. So I wanted to ask you a couple questions along these lines. One is what have you learned about investing, angel investing, especially what's most surprised you?

58:27I feel like there's a lot we've learned. So there's things on the operational side. This is the whole category of... Running a fund, there's a bunch of things that go into it from LP communications, LP fundraising. There's also like Vetica who works with me on the fund side, she describes it as hygiene. There's also good hygiene when it comes to running a fund. For example, when you meet a founder, you should get back to them. 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 might just say pass, and that's not very encouraging to a founder if they give you no context, no details.

59:02There'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. We like to know what happened, have them close the loop. And so there's good hygiene, operational things that we've learned and kind of honed over the years. The biggest surprise has probably been, I got to be careful of how this is interpreted in some ways, but there are cases when I didn't think the company would make it. Either the product wasn't working and many months had passed. And it was very clear, well, to me, I thought it was clear that, okay, this probably isn't going to work out.

59:41In my head, I kind of wrote it off. And then that company either pivoted or some massive partnership or M&A kind of event came through out of nowhere. And so I guess the learning is never count a portfolio company out until it's over. And that relies on, of course, backing founders that are very resilient and creative and driven to create momentum out of nothing. But that's been surprising to me and it makes me kind of excited because we've invested in over 110 companies now, and it's fun to be able to see behind the scenes a little bit how all these things kind of play out both the good and the bad.

60:21That's such an inspiring takeaway. Does that change how you invest? 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 a very expensive hobby slash approach because there's so many great founders. How is that informed, how you invest seeing that happen?

60:39I would say we don't have... Again, my cop out, it's contextual kind of answer. Some people are like, we are team first only. Some are, we're market first. Some are, we're product first. And we look at everything kind of holistically. And I think the evaluation of the product is sort of a reflection on the team. So our assessment of the thinking behind the product that they built today, and maybe some of the traction, is a reflection on the team's abilities and the thought processes. So we try to look at it holistically. Yeah, every investor would say, yeah, we want to back resilient founders that are very driven, insightful, and all those things, of course.

61:18But it's also sometimes hard to fully evaluate that unless you really know that person. So we try to take as much data around how the product is working, how they made those decisions leading up to this to evaluate the team indirectly.

61:34That's kind of what I've started to do, is I try not to invest as a founder bet unless I just know them because it's just so hard otherwise.

61:42Yeah. Yeah. There's a few founder bets that we've made. One, going back to consumer social kind of thing. He's somebody I'm known for many, many years. One of the most talented designers and deers, product builders. And I've just been waiting for him to start a company. And so that was one of those, I'm going to bet on you because I believe in you. I'm not sure about this first idea, who am I to judge? But I don't know if that's going to be it. But he's probably going to launch 10 apps and the 11th is going to be a massive success. And so that's sort of the way I think about those consumer social founder first bets.

62:18I 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?

62:27Yeah, I actually wrote a tweet storm and converted it to a blog post on this because we've gotten a lot of, you probably as well, get a lot of emails or people saying, "Hey, I'm thinking about raising a fund. How should I do that?" Or, "I want to get into venture. I want to start investing. What advice do you have?" So yeah, we wrote a blog post on this and there's many different ways to invest. Angel investing is one. So great thing about that is if you have the capital to angel invest, you would do it today, tomorrow, no sign-offs required. You have maximum flexibility, but of course you need to have disposable income. You need to be able to be willing to lose all of it.

63:02And then hopefully you'll be on the other side of that and make some money in 10 years. It takes a long time. They're scouting. That's another opportunity. They're more and more scout funds probably than ever before right now in different flavors. Some of them are dedicated kind of scout programs where you have capital to deploy on your own. Some are more like you still need approval, but you send the deals and you get to carry on those deals in many cases, those have pros and cons too. 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 program or that fund.

63:37You 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 one angle, which works really well for a lot of people. So for those that maybe don't know and listening to this right now, SPVs are essentially a single vehicle 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. One, you get deal by deal carry, meaning the outcome of that company is you get paid when they exit, essentially, assuming there's a positive outcome, versus a fund, you have to return the entire fund first.

64:12Two, it allows you to also bring in maybe very strategic, helpful people into that particular round for that company, which can actually be a strong value add for that founder. The biggest trade-off is it's a lot of work sometimes. 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 raising a fund. So 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.

64:46But it provided me with the most flexibility in a way to deploy many checks into many companies, especially when I didn't and still don't have a ton of money to angel Invest. So anyway, those are different options. I think my blog post goes into more pros and cons for each of those things. But the last thing I'll say actually is let's say none of those are really an option. You don't want to start a fund. You don't have enough relationships to do SVDs, for whatever reason, you can't do a scout, you don't have any money to angel invest. One thing you can also do is just pretend angel invest.

65:21And that doesn't mean that you're meeting the founder and writing a check, but you can write memos or you can almost create a fantasy portfolio. And this is what Vetica before she joined me was doing to some extent. She was writing memos about companies she was excited about, and in some ways she was doing the job before getting the job. And anyone could do that today. And that can be helpful too. If you're applying or trying to prove your abilities, you can say, "Hey, here are the memos, here are the companies that I would have invested in if I had the opportunity, and here's my thought process behind that."

65:56I 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 do that too. Where do you think this all goes for you? Are you thinking of increasing the fund? This is basically the last question, just what's the future of Ryan Hoover at this point, as far as you know?

66:15Yeah, still figuring out the meaning of life as we established earlier.

66:19I thought we cracked that one.

66:20Yeah, yeah. I'll let you know when I figure it out. Yeah, we're on a third fund right now. We're actually about 30, 35% deployed. So we have plenty of capital and we're not going to be raising anytime soon. And yeah, we're just investing in early stage companies right now. But yeah, when I fast-forward longer term, I don't know, I will always be investing. I'm also more of a fan of maintaining a smaller fund. Our latest fund is 21 million, and 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 really collaborative. We can write smaller checks, we can fit into competitive deals.

66:59I think it's a better product for founders. We're not trying to take the entire round. We can try to bring on the Lenny's 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 the most fun. So creating something, whether it's a company, I don't know. I don't know what it's, I'm not going to even call it a company, but building something is hopefully in my future. I just got to figure out the right idea. And maybe reflect on your blog posts too, on the idea generation stuff that you shared because that is helpful.

67:29As long as you let me invest, all is good.

67:34Yeah. Well, I don't know. Part of me is like, do I ever want to raise from venture? Now, it depends on the idea. If I need it, if it's required strategically, then yes, but to be quite honest, maybe I shouldn't say this, I'm kind of really interested in just owning something 100%. And you can always raise venture later. It's a one-way door, so I kind of want to delay that door for whatever I build next, if I can.

68:00I 100% get that. That's how life is with this newsletter operation, and I highly recommend it if you can pull it off.

68:07Yeah.

68:09Okay. That's it. Just where can people find you online? It's kind of a dumb question because you're very easy to find, but where do people go to learn more if they want to reach out? And then how can listeners be useful to you?

68:21Yeah, I'm just easy to find RRHoover on Twitter. RyanHoover.me is a simple website, have a bunch of old blog posts on there, probably with bunch of broken links and broken images. But it's there, the contents there. I don't know. We're investing, we're investing in the early stage companies, B2B, B2C, building something weird. I don't know. DM me, email me. I'm around.

68:43Amazing. 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.

68:59Yeah, thanks, Lenny. Yeah, these conversations are helpful and reflecting on what do I actually believe anyway? So it's just like writing. It's helpful.

69:08And it is just as helpful to everybody else. So thank you again.

69:11Cool. Thanks, Lenny.

69:13Thank 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.