The Exchanges

Q my God, this is, why am I doing this to myself? My general advice 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?

A 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, especially are certain bubbles of tech. That's the default. It's like the first thing I do, I have an idea now let's go raise money. And 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 product and it was a side project in 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 want to 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, uh, early, and investors were, were using products that reached out to me and they were sort of courting, courting me and, um, kind of doing that little 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 decisi…

AI assessment note: “my rule of thumb is a decade. Just do you see yourself working on this”

Q Cool. So from what I can tell, the weekend fun 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 of questions along these lines. One is what have you learned about investing, angel investing, especially what's most surprised you?

A I mean, I feel like there's a lot, a lot we've learned. So there's, there's things on the operational side. So the 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 Vedika 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. 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 it gives 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 was 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, either the product wasn't working and, you know, many months had passed and it was very clear …

AI assessment note: “the biggest surprise has probably been... there are cases when I didn't think the company would make it”

Q 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?

A Yeah, I actually, um, wrote a tweet storm and like 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. Like how should I do that? Or I want to get into venture. I want to start investing. Like what advice do you have? So yeah, 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 angel investor, you would do it Today, tomorrow, like there's, there's no, no sign offs required. We 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. And then hopefully, you know, you'll make, 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. 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 relying on that, that pr…

AI assessment note: “there's many different ways to invest. There's, you know, angel investing is one.”

Q As you know, I asked people on Twitter what questions they would want to ask you, and so I'm gonna inter-splice these questions as we go through this, and you just touched 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?

A Great question. So at the time, this is also the thing I asked founders is why do you need to raise money? Like, what is it for? And surprisingly, some people are like, 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 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 with that? Like that's really hard to do. And when you're building a company, you probably don't want to 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 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 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 a very small team. So today it might be a little bit different in which I might not raise venture capital because Product isn't t…

AI assessment note: “at the time raising money was the right decision because I, I wanted to hire”

Q If you'd like to learn more or get started, check out Flatfile at flatfile.com slash 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 around the street in life? And has there ever been like a super awkward or super hilarious moment of that?

A Yeah. So product and started in late, and quickly got a lot of traction in, in the tech tech sphere. So yeah, people in tech, um, might recognize me. People last night 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 of 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 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 every Saturday. It was like a mashup dance party.

AI assessment note: “in San Francisco where everybody's in tech, um, there's a lot of that”

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

A I mean, I don't know. It's, it's funny because if you, we should do some, like, historical analysis on Product Hunt because 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 B to B companies do well there? And I'm like, yeah, like probably more B to B companies than B to C companies actually. And so you see, you know, seemingly boring companies that tap into something that, that, that, uh, people find useful or resonance 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 on, 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?

AI assessment note: “I mean, I don't know. It's, it's funny because... it varies all over the board.”