The Startup Ideas Podcast - Building From Scratch with Ryan Hoover

Episode Date: June 10, 2022

Do you trust your gut? In today’s episode, we explore how the world's most disruptive innovations begin with just one small insight, share why successful founders need to embrace their niche, and why the best products & brands always seem obvious in hindsight. Hosts Sahil Bloom and Greg Isenberg are joined by Ryan Hoover, the builder who gave us Product Hunt and now runs Weekend Fund, an early-stage VC committed to “backing your next favorite thing.” Ryan is a serial entrepreneur and deep thinker who offers unprecedented insight into the future of fundraising and how one can generate wealth from hustle alone in this episode.►► Want more community? Learn more here: http://trwih.comSPECIAL THANKS TO OUR SPONSORS►► This episode is brought to you by Fundrise. Fundrise is on a mission to use technology to build a better financial system for the individual. With over $2.4B AUM and 250k active investors, it’s the largest direct-to-investor real estate investor platform in America.Their platform is so easy to use and they make it so easy to diversify your portfolio. For a limited time if you sign-up, you can get $10 bonus. Just go to www.fundrise.com/room►► This episode is also brought to you by LMNT (http://DrinkLMNT.com/HAPPENS). LMNT is a delicious electrolyte drink mix with all of the things you need and none of the junk. It contains a science-backed electrolyte ratio: 1000 mg sodium, 200 mg potassium, 60 mg magnesium. LMNT can help prevent and eliminate headaches, muscle cramps, fatigue, sleeplessness, and other common symptoms of electrolyte deficiency. It tastes amazing and is great after a workout or one too many drinks :)Right now LMNT is offering our listeners a free sample pack with any order. That’s 8 single serving packets FREE with any LMNT order. Get yours at http://drinklmnt.com/HAPPENS. And it’s so good they have a no questions asked refund policy but you won’t need it.THIS EPISODERyan Hoover: https://twitter.com/rrhooverSahil Bloom: https://twitter.com/SahilBloomGreg Isenberg: https://twitter.com/gregisenbergProduction & Marketing Team: https://penname.co/FIND US ON SOCIALTwitter: https://twitter.com/_trwihInstagram: https://www.instagram.com/_trwihTikTok: https://www.tiktok.com/@_trwihWeb: https://trwih.comSpotify: https://open.spotify.com/show/6aB0v6amo3a8hgTCjlTlvhApple: https://podcasts.apple.com/us/podcast/where-it-happens/id1593424985

social products, community products, especially. It's not like you need everybody on there. You actually probably don't want everybody on there. You just want like a really tight-knit group of people who are really excited about what you've built. And then that kernel can grow into something much bigger. Dude, it's great to finally have you on. I feel like this has been a long time coming and we're excited to get a chance to jam. And hopefully do some like kind of live ideation on some ideas and different things along the way as well.

Cool. Yeah, yeah. I've listened to a number of your podcasts. I think I'm a third of the way through the Tim Urban one from, I think, like, a week ago or something. He's a fun one. Tim is a fascinating guy and a deep thinker on a wide, wide variety of things. I mean, that was like, I was sitting there having that conversation with him, and none of those things were on my bingo card for the day.

That was kind of how I felt coming away from it. Like, I never thought I would learn about boots void, you know, the massive expansive space that is unoccupied on a random Friday afternoon. But go figure. Yeah. Today's episode is brought to you by Element, a tasty electrolyte drink mix with everything you need and nothing you don't. That means lots of salt with no sugar. It contains a science-backed electrolyte ratio, a thousand milligram sodium, 200 milligrams potassium, and 60 milligrams of magnesium, but none of the junk. No sugar, no coloring, no artificial ingredients, no gluten,

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Ryan, do you listen to a lot of podcasts? Because I feel like I see you on Instagram posting stories of you listening to a lot of podcasts. I think you're referring to my, so I have this semi-new ritual. So I've been lifting weights for a long time. Like, that's been my like exercise, the kind of activity. And maybe a few months ago. I was like, I should do more cardio, but I really don't like running. And so I got a recumbent bike, not like a Peloton where you have to like sit up. I got a recumbent bike where you get a sit back and email and tweet. And I have like my iPad set up here. So I watch podcasts. And so I think that's what you're seeing is my promotion of the recumbent bike multitasking podcast email.

There's a powerful learning in there, by the way, of like pairing behaviors. You know, like pairing a behavior you dislike, but you want to, you know, adopt with one that you like or find productive. I've always done the same thing. Like, whenever I need to try to get back into cardio, I'm the same as you. Like, I have always been a lifting nerd from back into baseball days. And so I'm still that way, but then I neglect cardio for long periods of time and realize like, hey, I'm 30. I should probably, you know, take on more of this, whatever. And I've always paired it with listening to something, watching some show. I've been wanting to watch, you know, like reading. emails, whatever it is, something where I'm like, oh, okay, I just unlocked 30 minutes a day,

make up the number of time that is now considered productive that I can like justify doing this thing that I generally hate. Yeah, there's a, I'll give you a shout out to Huberman podcast. I don't know if you've seen his stuff. It's, it's quite dense. It definitely feels like I'm in a lecture like back in college, but it's great. I mean, for those that don't know, he basically goes into the science of psychology around a number of different things like how dopamine works or, you know, anxiety, depression. And he talks, he actually has one podcast on, I forget the exact topic, but he talks a lot about that same thing and how he actually recommends not listening

to podcast or music if you enjoy it at the gym every single time because you start to, essentially your brain starts to expect that and it doesn't get as much joy over time. And this is the unfortunate reality of like how dopamine works. and I know very little about it, to be honest. But it's unfortunate that, like, what goes up must come down. And over time, you start to acclimate. It's kind of like Hidonah, kind of like treadmill that we're all on, start to acclimate to those things.

So he sort of recommends that, like, actually don't always do all the things you enjoy. Maybe don't listen to podcasts at the gym. Just like enjoy the gym as it is and maybe the next time listen to your podcast that you enjoy. And I find that interesting because I'm a very habitual person. I do the same thing all the time. and make the same copy in the morning. I'm very, very routine. But always listen to where it happens at the gym, please.

He mentions that, yeah. I know. There's something about the Where It Happens podcast. Yeah, I think he did recommend that. He's actually, I have him coming on the show this summer. I want to do like a kind of layman's version of his podcast. Like what are the 10 things that every person should try to adapt into, you know, adopt into their life to make them a healthier, happier person and do like the takedown

version of Huberman Lab on our show. So I've got him coming on this summer. He's supposed to be in New York a couple times. So I'm going to try to get him live. Yeah. I think they'd be great. I do, I would like a TLDR. Yeah, totally. Because I've listened to several of his, I mean, he's kind of the Lex Fridman, you know, Joe Rogan. Like it's that length sometimes and density where like they'll do an episode on sleep that is at, you know, unbelievable. Like with Matthew, Matthew Walker, I think is that sleep scientist's name. But like, like, I'm sitting there for three hours learning about sleep. Like I kind of want the, you know, what is the Cliff Notes version of this that will get me 80% of the way there with, you know, 10% of the thought.

Yes. Yeah. I mean. It's our, it's our era of, you know, low attention spans. I'm actually amazed that people sit through and listen to a really long podcast. But people do. You know, those long episodes, people love them. Yeah.

I actually like, I like conversational podcasts. I like Joe Rogan for the format in part because it's, it's one of those. things you can kind of dip in and out of you can multitask too. I don't watch all of them, but sometimes they're an interesting guess. I don't know. It also feels like you're in the room with other people. And I think, you know, I think more and more people are understanding that, that format and kind of adopting that format more and more. But I don't know, it's, it's better than like the sterile, like, interview, question, answer, back and forth format in my mind. I agree. I mean, that was the original insight of where it happens, too, by the way. It was like,

you know, it was the room where it happens. It was like, we know that these conversations are happening behind closed doors, though. And so, like, smart people or interesting people are having interesting conversations that generate insights that are then creating innovations in the future and changing the future. And so how do we open the door to those type of conversations and basically just bring guests on, you know, super smart people that think about the future for a living like you and just jam on interesting things that are happening and, and publicize that conversation and, you know, and go put it out so that other people can hopefully benefit from it in some way.

So that's kind of the spirit of it in general as we've thought about it. And selfishly, you know, both Sahl and I have Twitter, Twitter audiences. And we were talking about like, how can we build affinity basically with our audiences? There's one thing about actually going in tweeting 200 and some odd characters. But, you know, being in people's ears all the time, definitely build affinity. I'm wondering, you know, would you ever start a podcast? Why or why not? think about that. Yeah, so early productant days, well, I've listened to podcasts like probably you as well,

like for many years and I really enjoy them. And I used to mow my parents lawn with gun mucks on with my old school like, you know, headphones underneath them. And listen to like stupid financial podcasts. Like I don't know. I just would love to soak up like information and insight and perspectives. And so I've listened to a podcast forever. And then Productant started and I was like, shoot, now I have an opportunity to actually start a podcast. Like it makes sense. Like we have an audience, we have a brand. You know, it kind of wrote itself.

The product and podcast was actually very similar format to kind of this to some extent. We bring on one or two people who are interesting. Maybe their investors, founder, someone in technology. And we just talk about like what products do you love? What's in your home screen? Like what things have you seen recently that you're excited about? And we did that for a while. And then I stopped doing it just because it wasn't like the highest ROI thing.

we'd never really crack the growth thing for the podcast. Like, you know, the people who were most engaged in product content would listen to it, but it wasn't anything that reached like hundreds of thousands of people, let alone millions. So the growth part of podcasting is the hardest part. It's kind of like Twitter itself. Twitter's really hard to grow your audience for most people. It takes many, many years in some cases to grow a sizable following.

And I feel like podcasts are bad, but even harder because you don't really have built-in like social dynamics to grow it and get those feedbacks, feedback loops that you kind of get from social media. But I thought about starting a new podcast and I'm just hesitant to anything right now. I'm just like, do I really want to do that right now? Can we get into the, what you hit on is like an interesting insight more broadly around building products. And it's like driving and creating these like incentives and referral loops that kind of

create growth and create community. And it strikes me that like product hunt was a great example of that in the early days, like how you built this incredibly fervent community of product lovers and product minds. You know, I imagine, and I don't know the whole story. So I actually would love to hear it of like the earliest days of like planting that seed of growth that then sprouted and obviously has become something really massive globally. I would love to just hear a little bit more about that. Like how did you think about creating those in, you know, referral loops and

incentive loops, getting people to share, getting people to interact and build that, you know, community fire that you could then kind of pour gasoline on. Yeah. Well, so I was talking to a founder yesterday who's exploring some different social community ideas. And so I'm going to almost counter my own advice or experience. On one side, he has a lot of really good ideas. He's brilliant kind of designer, product thinker. And people like him can be challenged with. overthinking things because we like to think in systems we like to think in flywheels we like to think of like oh if we have this thing and unlocks this thing and unlocks that thing and that's important i think very valuable to like dissect and try to understand however you can also become paralyzed and

like over engineer a product if you think if you think you're too if you're like too clever basically and what i mean by that is i've made mistakes in the past where we built new products within product that were like way too complicated like because i thought i was so smart i was so clever i was like oh, we can do all these things and what about this feature and that feature? And we ended up spending way more time on it to bring out the V1 than we needed. So going back to product in the very beginning, I wasn't actually trying to build a company or a product. I just was like, I like finding cool new products.

You know, why do we have to like hunt for the link inside of TechCrunch articles? Why isn't there just a simple list of here's what's cool that launched today? And I was also kind of weird that was like brass in the app store and various countries. And I was browsing angel lists looking at new companies just to see. what people were building basically. And so the initial idea was there was no systems thinking, there was no like grandmaster plan. It was just, oh, what if I started a newsletter? Because that's easy to do first of products that launched or products that people find interesting. And that was sort of the spark that, you know, proved out that, okay, some people, some other people, not just me

like this type of content. And then it sort of naturally fell into, okay, well, newsletters a great start, but obviously we don't have any place to like curate this. at scale we have no place for comments there's so many things missing that can make this better and so a lot of the i would say like first 12 18 months of product had the roadmap sort of fell out it was just like almost obvious um based on what people were doing the feedback we were receiving and then over time we started thinking more like system that sort of organically meaning i'll use an example um so initially when the product and website launched it was kind of like reddit we're like let's not reinvent the wheel let's have post

and comments and upvotes and keep it simple. And what we found was makers, the founders, the founders, and people that built those products, would increasingly come to the site and be like, oh, I made this thing in the comments. Like, if you have any feedback, if you have any, like, questions, let me know. And then it was, like, very obvious to us. It was like, okay, why don't we actually productize that

and make it clear that this person made the thing or these people made this thing so that people in the community could identify those people. And now that might seem like obvious and kind of trivial, but actually what that unlocked is you think about it like a system. It unlocked a really interesting dynamic where, okay, people follow these people, know these makers. Maybe they want to know what their friends launched or people that they follow launch. So it led us to unlock sort of these engagement loops through email.

So like if Greg launched, you know, his new like islands back in the day, everyone that knows Greg or follows Greg on Product Hunt would now get notified. And those would have really high open rates and engagement rates. And then, of course, the next part of the system is, oh, now you can build the profile. You can have this profile of things that you made and kind of show it off to other people. And for a certain subset of people, especially like indie makers or like young entrepreneurs, they're like very proud of that. And so all those things sort of like unfolded sort of naturally in the roadmap. But but yeah, if I tried to like think of all those things from day zero, in some ways it might

have been like paralyzing because it's like, okay, we have all these ideas. But like at the end of that you have to just prove out like the core dynamic, big core, like, value problems early on. Yeah, two things you hit on that I want to double click into. One, you know, you mentioned like overthinking and paralysis. And I mean, you guys are both builders and it built multiple different products and different things over your years. I've always thought that like overthinking tends to come from inaction. And it's not that you're like not acting.

And so you start over it's sort of like when you're not acting and when you're not, you know, having that bias to just get things. out, tests, learn, iterate, etc. That's when you find yourself prone to overthinking and overanalysis because you're just you're sitting there and you're like, I'm not going to act, let me just pause, wait, et cetera. And so you get caught in that. And so I'm curious just for your guys' perspectives on that.

Like, have you found in general that overthinking results from inaction? So consumer social, first of all, is its own beast, in my opinion. And when you think about zero to one consumer social, it's probably, 90% art, 10% science. Now, once you actually build some level of product market fit, that changes over time. And if you think about like Facebook, like, you know, they had Instagram and then they're like, they bought Instagram and they're like, okay, let's just sort of like bring what we learned on Facebook and apply it and optimize it on Instagram. So then you end up just running experiments and it becomes 90%. science, 10% art.

So I think what Ryan is saying, and correct me if I'm wrong, but I think what you're saying in the early days, it does feel a lot more organic when you're building community or social products. And you kind of have to just go with your intuition a lot of the time if you have a unique insight in a particular field. Like you understood at the time, like, and I was there, like, SF, tech, products. makers, like you understood that and it was under, it was underserved. And correct me if I'm wrong. Like the first time I heard of product hunt was, I think I was invited to a brunch.

And we did do some brunches. Yeah. Yeah. Yeah. And yeah, I'm wondering if you can talk a little bit about in the early days the importance of, you know, the events and brunches. because when you think about building a tech product, you don't really think about over easy eggs that much. There you go. I don't know. I think of over easy eggs immediately, Greg. Yeah, that's a good like...

Avocado toast, actually. That's a good chapter title for your next book. Yeah, I mean, so a lot of this was organic too. So even before a product and that was actually doing some brunches and the kind of meetups with like other founders and people. And I don't know, I was trying to build like, you know, relationships with people and learn. And I was basically trying to soak up as much as I could.

Meeting people in person, especially when you're in San Francisco, was enjoyable. And so when product kind of like, well, when we hit some level product market fit, we had just as I felt obvious to me like, oh, why don't we just meet up in person? We've been like talking about this tech, you know, online. And so we started our first meetups. And then over time, other people in the community like, hey, can I do a meetup in Bangalore? Can I do a meetup in Berlin? So I don't know how many we've had, but maybe over a thousand meetups across the world.

hosted by the community where, you know, we support, but basically they run it all. And that's been just really effective in building more tight-net community. And it really is almost like an IRL version of what's happening on product in some ways where people want to connect with the people, people want to learn about technology. They want to geek out about this thing. And there was kind of a, you mentioned this earlier. There was sort of, that was missing to some extent on the internet. Yeah, there's subreddits for tech.

There's Twitter. But there wasn't sort of this destination for new products and like this. optimism that we were trying to to encourage. So I think it goes back to like to do things and scale component. Like I think social products, community products especially, it's not like you need everybody on there. You actually probably don't want everybody on there. You just want like a really tight knit group of people who are really excited about what you built. And then that kernel can grow into something much bigger. Do you think, and this is a question for both of you guys, I guess, just from your product building experience, do you think that the best products feel

extremely obvious. Like you said that Ryan in the early days of product. Like you were just letting customers guide you. And like every, you know, the product roadmap was informed by things that just felt obvious. Like, oh, we definitely, like we obviously need to do this because all the customers are asking for it. We had a discussion with, with Greg's friend, this guy, Nick Salterilli from Midday Squares. And he was like, there was this change that I just had to make, which made no sense on paper as like a financial move. But it was just so abundantly obvious from the consumers and from the people that cared about the product that I needed to make this change. And it started getting me thinking about this loop of like,

is a good heuristic to just say like the new rollouts need to be the things that just feel so obvious to you when you're going and doing them? Do you think that's an effective heuristic or do you need to, you know, kind of be more dynamic than that? I'm curious to get Greg's take on this. I mean, hindsight is always obvious as the challenge. Right. Because if you look back at some ideas and you're like, you know, let's take Snapchat, you know, it's in hindsight like, oh, it makes a lot of sense why, you know, kids were sending ephemeral photos.

But in the moment, you know, most people didn't get it. Most people didn't realize that that opportunity. So I think a lot of it is there's another kind of like question to ask that's related to this in my mind, which we asked a lot on the investing side, which is, you know, what's changed? Like, what is there a regulatory shift? Is there a consumer behavior shift? is there a technology shift? What's changed in this world to enable this new thing to emerge? And going back to Snapchat, I wasn't obviously in the company.

And I don't know all the details about Snapchat, but a big shift. A big part of that was kids on Facebook just didn't want their parents and their teachers to see their posts. They were also concerned. I think this is also the rise of like cancel culture kind of emerging and other things like that. And so the ephemorality was very counter to older generations who want to. save everything and go back to those things. That's really not what a younger generation, you know, wanted. So I don't know. I think a lot about that, like what's changed. And especially in consumer

products, there's always, even if you just take the generational shift, like people that grew up in different times, like grew up with smartphones, have very different expectations and ways of speaking and engaging that that maybe don't adapt or align with like today's modern day, like, giants. Like, you know, let's take Facebook as an example, Facebook.com. So I find that really interesting. I try to understand that when I'm speaking with founders. It's almost like, I guess the nuance or like the tweak I would make to what I said originally is like the initial insight, if you want to build something huge, world changing, et cetera, the initial insight has to be contrarian, really. I mean, it has to be something that no one really agrees with you at the time

and then everyone agrees with you later. That it's like, oh yeah, Snapchat, you know, you use that example. It's a great example. At the time, you're like, probably no one agreed with it. There was most people, because if everyone agreed with it, someone else would have built it. There would have been a thousand Snapchats already. And so it was like an initial insight that was novel and contrarian that in the future everyone agreed with. And that's kind of as an investor or as a builder. That's what you want. You want to build things that everyone agrees with you on later in the future. There's some great kind of quote, investing adage around that. But maybe it's that that initial insight has to be contrarian and very different.

But then as you get that flywheel going and like as product market fit exists, you're able to be led by the customers into things that feel very obvious. And so then like the next layer of rollouts, the next product, the roadmap starts to be informed in a way that feels really more obvious because your customers are kind of leading you directly there post PMF. Yeah, I think the way people's brains. work is everything seems obvious in hindsight. So people will say, oh, my God, obviously that product would fail because of

XYZ in hindsight or obviously that product would work because of XYZ in hindsight. And I think the truth is when you're building consumer product, it's all about having some key insight in a particular niche and being like weird, basically being weird and building a product that's weird and weird that's in a good way for the people in that niche and weird that the people outside that niche are kind of like, well, that's weird. Why would I ever use that? And that basically buys you time to iterate on a product in that particular niche and really, really serve them in a remarkable way. And like Snapchat, you know, Snapchat was a product for Los Angeles high school students

to send nudes, basically, initially. And it was for them, like, the best product in the world for a period of time. And then they expanded that and expanded that and expanded that. So much to the point where now there's, you know, hundreds of millions of daily active users. So, you know, I'm not recommending, you know, create products that send nudes to people. But what I am recommending is, is go into that niche, go into that niche and serve them well. I mean, Nikita did this, right? Like with TBH and with any, like, you know, new stuff he's working on, it's like he, even if it's not some, like, amazing insight about people, it's like, you know,

what high schoolers are already doing. They're gossiping about each other. They're talking about each other behind their backs. They're saying things about each other. And so like, what is a product that you can build around that natural human instinct for gossip? And there's a ton, right? There's just like having a small insight or being willing to kind of like play to a natural human instinct or desire, it can be a really powerful building insight if you're going to go create things. And the truth is you need as a maker, you need one. small insight, which could absolutely transform your life. That's a good point.

Yeah. Like, if you come up with one small insight in a particular niche, it could literally, literally change your life. Just like, you know, you can have one tweet that gets 100,000 likes or 500,000 likes, and then all of a sudden you have this new audience, and it might transform your life. So just changing gears a little bit, because I do want to get into some, like, ideation. stuff. Ryan, what are you working on now? Like, I know you're not formally working on product stuff anymore. What's your focus day to day? What are you, what are you thinking about or getting

excited about? Yeah. So I'm investing full time now. And we're investing early stage, pre-seed, you know, seed stage companies across everything. So we do love weird consumer stuff. We're investing in Web3 stuff. We're investing in boring SaaS stuff. Like really, lot of our through line there is like what is what is change what's the consumer behavior shift what's the technology shift and part of that thinking is obviously startups are not private market startups are not 100% like efficient but they're getting more efficient because more and more people are building and trying new things so that's why we think so much about the why now like what's changed kind of question on the investing side so um so vatic and i are working on on the fun side

we're also constantly trying to experiment with different things I would say like we kind of break up the And like one is, how do you say it? Business as usual, meaning you meet founders, you evaluate founders, you do diligence, you support founders, sort of like the table stakes of investing. And then there's another thread which is like experimentation. And we're always experimenting with different ideas. We've had, I don't know how many experiments we've done. But basically we try to build things, not necessarily products, but build different products,

not in the software sense. So the most recent one is operator LP. is what we're calling it. I don't know if it's a great name, but that's what we're calling it for now. And the idea is we're seeing a lot of our friends, a lot of people that we know, raise funds. And a lot of them, of course,

raising a fund from LPs is very difficult for a lot of people. Furthermore, we also have a strong belief that investing is increasingly customer-driven, community-driven, network-driven, and that's why we raise from 370 LPs in our latest fund. So we raise from tons of operators, like some top designers, data scientists, engineers, salespeople, we have hundreds and hundreds of LPs who are financially invested in our success

and therefore the portfolio success. So we started this experiment called the operator LPs, basically like a GP demo day to connect operator LPs. So not necessarily the fund of funds and the endowments, but really these are people that might write 10K checks, 100 K checks into funds who are excited to get involved and back these GPs. Mostly smaller funds is what we focused on, like mostly like sub-20 million dollar funds. And our selfish goal is, well, our selfish goal is really to build a stronger network with LPs and with GPs to sort of help, but we're not taking, we're not charging for this, we're not getting economics, we're just experimenting to see kind of where this can play out. And so far we've run two GP

demo days with three people in each demo day. First one, we had about a $1.1 million in interest. Second one is $1.5 million in interest. So, you know, we're still kind of gathering data points to see, like, is this valuable to people like this? And sort of the next step is to figure out, okay, what does V2 look like? How do we expand this to more GPs to more LPs, just to really decrease the friction from the fundraising side? And what we really want to do is push the industry forward towards more collaborative, more community investing beyond just the investor founder side, but GP and LP side as well. If you're anything like me, your portfolio is a mix of the usual suspects. stocks, bonds, and mutual funds.

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think it's an amazing initiative. I know more and more people are interested in investing, you know, have some unique network or some unique angle value at, et cetera, but don't have the LP relationships or don't really know how to go about, like, sourcing deals or deploying capital at scale. Like, if you were for either one of you, and I'm happy to weigh in on it as well, if you were kind of like dropped with nothing and wanted to begin angel investing or begin investing in earlier stage companies, what some of the advice or what actions would you take in order to kind of establish yourself and start to execute against that? I'll jump me real quick. So I'm going to speak on Vedica's behalf. So her and I are the two

on the fun, met her over three years ago. And she was a product manager working in a company, but she was writing fantasy memos, is what she called them. So she was looking at companies. I remember Retool was one of them way back in the day and writing up a memo as if she was investing, almost like an analyst would, as if she was proposing an investment in this particular company. And she wasn't sharing that with anyone. It actually wasn't even online,

which maybe she should have shared it online. But she wrote it for herself as like, almost like practice, like an exercise. And anyone could do that today. You don't need money. You don't need connections. You don't need any of that. But what it will do is help you,

I think, refine your thinking if you were to invest. And furthermore, it creates a paper trail. When I interviewed her for the role, she just sent me these fantasy memoirs. I was like, oh, my gosh, you're basically doing the job already. And I can see your work and can see how you think. So I think that's an obvious, like, brilliant step. And if you don't want to do that, then maybe you shouldn't be investing. Like, that's the job, to some extent.

At least that's part of it. So that's my progress recommendation. That's such a cool example, too, because there are real case studies of people doing that now. in a very public setting. I think of both Pachy and Mario at the Generalist as like two examples of people who built a, you know, owned audience via their newsletters through writing and dissecting

and deconstructing businesses and trends and principles. And then on the back of that, are able to go and say, like, you know how I think about businesses. Like to LPs or to people at scale, you can go say, like,

you know how I analyze businesses. You know how I think about bull cases, bear cases, etc. because here look, here are like the 10 cases where I've written about it in a specific context. And so you can go on the back of that and like leverage the information you've generated at scale to go and raise capital and deploy it. The other one I always think of that I think is just an untapped opportunity for, it's mostly like for, you know, people that I think have a lot of ambition or like a hustler mentality is just the opportunity to be a scout for some of these like emerging managers that have come out. You know, I think about like, I think Sahelabinia has like a scout program more formally, which is great. It's like a formal construct.

But this whole idea of like, you know, for people that don't know it, it's like you're a scout. Like you kind of go out and search and hunt for deals. And when you find one, you kind of like bring the deal to some manager. And if they do it, you get economics in that deal, i.e., you know, future profits if it goes really well, a portion of the carry. And things like Angel List make it amazingly easy to do that on a deal by deal basis, which is to your point, earlier, Ryan, on like, what has changed in an industry that enables some great thing to happen. That is something that has changed. 10 years ago, it was super complex.

Like, you had to go hire lawyers and pay them $25,000 probably to, like, dock up some, like, simple thing like, Kerry and splitting it on a deal by deal basis. Within a fund, it would have been too hairy. Like, as a manager, I would have been like, ooh, no, it doesn't make sense for me to do that. Now, if a kid comes to me and says, like, hey, I have this deal, it's a close friend of he's starting this, he's at, you know, MIT's building this, this and this, precede. You know, like you split the carry with them in one click on AngelList.

It's freaking amazing. And I don't think enough people are thinking about that as just like, honestly, like a little side hobby. If you're just, if you have networks, if you're, you know, getting out of school or you're a builder, you're like in internet communities, wherever, and you have these networks of people that are building cool shit and you have a good eye for it and you have those ins, you can go, I mean, if you sent me a blurb, you sent 10 other people a blurb on these companies, someone would probably take you up on the intros, on opportunities. And all of a sudden,

you're like building Kerry in a bunch of interesting future companies, that's kind of a, massive hack or unlock from a wealth creation standpoint when you don't have to raise any money to do it. And a name for yourself. You can say, like, I brought, you know, notion to Sahel or I brought this deal. I think that helps add a lot of credibility. I think my biggest, you know, advice here would be to, you know, if you do want to get more into investing, is to become the XYZ person. So, you know, for example, like some people called me the community person or Ryan, you know, the product person and stuff like that. And I think if you develop that niche, then people just start coming to you.

And you become the center of gravity for your vertical. So I think... Is this like Naval? Naval has that like, what is it? Like type 4 luck or something like that, Greg. Have you seen this? No. You or Ryan, like Naval has this whole concept of like four kinds of luck.

And I think it was like type four. That was this exact thing, Greg, where it's... You're just like the person in a given space. And so people come to you. Like, if you are... the world's best, I think he used the example of like scuba diver, like buried treasure diver. Then when there's some like weird buried treasure that gets found in some place, like you're the person they have to call because you're known as that guy. And so now you're getting lucky because you're

getting a cut of certain things by just being the guy in that space. Yeah, I think, you know, and I think with like Twitter and stuff like that, you know, building the audience on those platforms, but also like owning these email addresses. So what I would be doing if I was put on an island is like picking, picking a vertical, being really different and weird, and just putting out content that is unique in that space. And then doing like maybe weekly Luma video session. So for those you don't know, Luma basically it allows you to RSVP to different events. So maybe you do a weekly like, you know, if it's me, I'm doing like weekly community social,

web three stuff or whatever. and then I get people's email addresses. And then, you know, after I get 5,000, I'm like, okay, everyone, like, big announcement. Like, I'm launching a fund. And, you know, that's what I did basically with, you know, the late checkout rolling fund. Like, we raise seven figures yearly of a fund in a matter of days. And I never even took one meeting and I've never raised a fund in my life. And it was all through the magic of, of, of, of, of, of, of,

being weird and, you know, standing on the shoulders of giants of platforms like Angelus and Twitter. Yeah. I'll have one note on that actually, or one comment. So that's the similar advice in terms of like if you're starting to invest, you should probably just be like an expert in one thing and just like own it. Ironically, that's not what we do. But like my dad says, like do as do as do as I do. But I think that's the ideal advice. However, the only top you had like asterix output on that is I think it's super important to figure out what what it is what you choose because let's take an example let's say you're like the chat bot guy from like 2016 you don't want to be the chat bot investor because once you brand yourself as that

and then you know people realize oh this isn't a hot space it actually isn't as big of an opportunity as we thought you're now actually you know you're starting from behind the starting line basically you have to like rebrand yourself so I think I would choose something that you have extremely high conviction and that's authentic to you, that's sustainable. And that can be hard to figure out, like, what is sustainable. Yeah. People also do pivot. To be fair, like, how many, this is one that I just crack up about still. Like, every single VC in the world was a creator economy VC in 2020. And every single one of them is a Web 3 investor in 2021. And it's like, there was this hilarious meme. I think it was Josh Baby and Greg are, our,

friend from Metafi posted that was like the Woody from Toy Story being thrown on the ground and it was like creator economy was Woody and it was like I don't want to play with you no more. Throwing the creator economy on the ground. But like I don't know. I mean, I do think you can, on the margins you can shift. Obviously to your example on chatbot, it then becomes very difficult to not be branded as like, oh, that's the chatbot guy. But yeah, anyway, just like one caveat to it. Yeah. There's also one small thing. I'm trying to understand this better. So this is like a me kind of shower thoughting. Some of the people that have in the investing world that have made a strongest name in this respect in terms of being known for this particular thing and

an expert in this thing, they actually create language around this thing, usually their emerging trends. I would say like Injuries and Horowitz as a firm is probably maybe one of the most exceptional at this. Like Chris Dixon, especially with regards to Web 3 related things. Like there's there's certain words he has like skemorphism as being one like skeuomorphism is is sort of reflecting back to like the steve job days and that this product is too much it's too much of derivative of like a web two thing like web three social isn't maybe just like twitter on the blockchain for example and so the ability to create language that then everybody adopts is actually really powerful signal because now you become sort of indirectly known as the person who's like

pushing the language forward, which pushes thought forward and an industry forward. So I think it's like a really fascinating thing to think about like what language can you introduce that isn't like cheesy or isn't forced. That's the hard part. It has to feel, it has to be something that people can like grasp onto and understand and is valuable, not, you know, something that's like selfish in a way. It's also interesting to think about whether you can brand yourself around your lever of value creation. So we've been talking about it from like one end of it where you're branding yourself around, you know, the industry or the focus area, like your area of expertise from an investing standpoint.

But you kind of, you could flip it. You can invert it and say, like I'm going to brand myself as, you know, like Julian Shapiro, you know, like, oh, I'm like the product led growth or growth guy. And so like I know I can help you on growth. And so when people need to think about that for whatever reason, because it's a key part of their story of their company, and in that case, growth is in general in everyone's company, you think of that person. And when they're, you know, asking like, oh, who should I talk to for smaller checks? Here are some of the core competencies we need on our cap table. You get brought

up a lot because that's your core lever of value creation. I think about it for myself around like distribution and, and, you know, kind of getting access to, you know, large numbers of customers, et cetera. And so it's just interesting to think about whether you can flip it on its head and do it that way. Yeah, that's a really good point. That might be, that's a safer way of going about it too and arguably more valuable to founders that you back. Yeah, especially with small checks too. I mean, I think like it's a different game if, you know, it's like you Ryan and you're trying to more like lead seed or pre-seed deals and you're writing a bigger check and you need to really be able to offer something comprehensive in terms of an understanding, you know, helping them navigate the IDMAs,

etc. But if you're going to be a small check at the kind of tail end of a cap table, it's much more about like what is the one, you know, one vector that I'm going to help you with, you know, one tiny thing. You don't need to offer the whole, you know, buffet menu. It's just like, what is that one thing? I mean, I think about investing as a founder, kind of like a product. So you're selling equity and, you know, different investors cost different amounts of equity essentially. And they help in different ways. And Harry Hurst from Pipe has this concept called the check size to healthfulness ratio. Yeah, I saw that. That was good. Yeah, it's a good. Yeah, it's a good. It's a good way to articulate, I think, different tradeoffs, I suppose, when you're fundraising.

And essentially what he's saying is, you know, some of the people who write the largest checks may not be the most helpful. Some of the people who write the tiniest, like, 10K angel checks might be way more helpful than your lead investor who wrote a, you know, $5 million check in some cases. And so if you actually compare it, like Harry in this case, he would have sold a lot more of his company's equity to the $5 million investor versus the 10K check angel investor. And I think that's important for founders to acknowledge and think about. out. And it's one of the reasons why I'm such a big fan and supporter of like small funds and angels. And how do you enable founders to bring on a lot of really helpful people who can

really roll those sleeves and get involved without taking the entire round? Yeah, there's a lot to think about there. Well, before we run out of time, Greg, I know you or Ryan had one or two ideas that I wanted to, wanted to jam through. One of you guys want to throw something out that we can riff on? I'll start because I've been thinking of about this the last few days. It's one of those, me and my co-founder have this text thread. It's called Bad idea of the day.

And it's basically, I think I know what you're going. Yeah, it's kind of, you know, 97% of the ideas are bad, but like sometimes they're so bad, it's like maybe good. So just that's the context. Okay. So I was watching, or I have a friend or friend of a friend who was in a boxing match with other influencers. So I'm sure you're all familiar with Jake Paul and the Paul brothers becoming, you know, transitioning from almost influencer to boxers and taking it professionally. there was this event that happened a few weeks ago that was not, you know, Paul level of fame,

you know, not tens of millions of subscribers, but from the 100,000 subscribers to, you know, a couple million subscribers. And it was a boxing match that they rented out a university in Tampa and sold out. had this league where, you know, I knew some people who were boxing in it and some friends of friends who were boxing in it. And it was like the most fun I had had in a Saturday night in a really long time. So it got me thinking, like, is there an opportunity to create, you know, boxing is cool and everything, but like an NBA league but for influencers or a hockey league but for influencers.

So curious, your thoughts here. And there's a lot of directions where you can go. It could be maybe Web 3. It could be plain just like, hey, like, I think there was a show called Joe's versus pros or something like that. Like, you know, maybe you do like NBA type people versus influencer people. So just, yeah, I wanted to get your perspective there. I went to, I don't know,

maybe six months ago, went to the TikTok versus YouTube boxing thing, which sounds similar to maybe what you're describing. It was like basically TikTok famous people, YouTube famous people going head to head. And it was, I think I was, me and Susie are probably the oldest people there. I felt like it was a lot of people I didn't even recognize. But it was really fun. And the energy was like insane. I think there's, what you're touching on is sort of reminds me of like reality TV in a sense.

It's like reality TV made, well, it created an opportunity for regular people at the Fent Air quotes to be famous and it made it more accessible. It made it for the viewers, for the audience, be like, oh, I'm kind of like that person. I could be like that person. It made it more relatable. You're also touching on like, you know, people who are already famous doing something abnormal that they don't normally do. So I think there's something there.

I guess the only thing is would it be a one-off thing or would it be like you said league, which kind of implies like an ongoing like recruiting thing. Like would it get old, I guess? Would it get stale is sort of my biggest question. I mean, you have to create storylines around it for sure. Like to the reality TV point, you'd have to create, you know,

good storylines that kind of like ran through it if you were going to make it a series. But the, I mean, like, I just, like, if it's sports, I think it has to be a sport that's individual enough that you kind of have, you know, real faces and personalities coming out. Like you couldn't do a football, you know, a team or something where it's like they're passing it to. I don't know. It just it wouldn't it wouldn't

put the focus enough on these like individual personalities that have the you know, name, cash and brand. You could do probably like three on three basketball or like one on one basketball golf could be a really fun one actually of like they kind of did that with like Tom Brady, Aaron Rogers with Phil Mickelson and Tiger, I think it was, which was like really fun entertaining to watch because you can even the playing field from pros versus Joe's with with handicaps. But I don't know. I mean, I think there's probably something to it because you do have like owned audience. These people are entertaining to watch.

Hopefully like kind of funny or have some personality around like sucking at the thing that they're doing. It could be kind of interesting. Yeah. And I think what was also interesting is like you can do it. You can also do it like direct to consumer. Like there's like software out there that you can basically do a pay per view sort of experience. Like I think we paid $30 or $40 to watch this thing for a few hours. hours, you know, if you sell, I mean, you do the math, you know, if you can sell 50,000,

100,000 at $50 or $30, like it adds up. And I think, I'm not sure if it's a, you know, venture scalable business, but it might be something where, you know, someone who's listening might be able to like reach out to a few influencers and, and sort of bring this together. and do something small in their local area and then start proving out the model. I think it could be pretty cool. I really enjoyed it. I don't know if you know the YouTube creator Graham Stephan. He's personal finance.

He has like two or three million YouTube subscribers. And watching him get like punched in the face, and I don't even like UFC or boxing but it was so interesting to watch and I think a lot of these influencers are so they're entertainers so they understand how to get the crowd going how to like wear really fun costumes

it was you know it was more interesting than a professional boxing match and they had the audience to build up the high and the story kind of leading into it and everything. I mean, it is something that you could like theoretically apply to multiple communities. Like I'm even thinking like, can we do this in the tech community? Can we get like the most famous investors and founders to like punch each other in the face just for a night? And obviously like different communities.

It's like a broadly appealing like concept that could apply to different people in different communities around the world. I think. I mean, we've talked about that Sahel, I think. Right. we often say like you know there's a lot there's always uh there's always drama in tech twitter um and and people fighting back at each other so it would be kind of fun to put like you know an Aaron Levy versus Chris Dixon in in the ring and you could raise a lot of money for charity yeah it'd be pretty fun maybe that's how they fight for their allocations you know

in these hot deals it's like Forget the pitches. It's just whoever makes it out of the ring gets to write the time. You actually have to fight. It's a legitimate fight for the allocation and the deals. Yeah. Yeah. I would watch it.

I don't hate it. I don't hate it. All right. One more. We've got time for one more here. Ryan? One more. So I didn't come from having it with anything, but I'll share one idea that I'm,

this is actually to be me asking for feedback. All right. So I thought about this for years with zero. action. So I'm, anyway, not a good trait to talk about something for so many years and not doing anything about it. But the reason why I haven't is because it's commitment and I'm scared of commitments. So I don't, I don't really vibe with any of the co-working spaces I've been to anywhere. So I've had this idea when I lived in San Francisco. I had this V-1 when I was in LA. I'm now in Miami. And especially Miami seems like a good place for this. And essentially what I'm, what I'm

imagining is how do we create a small, intimate co-working space with good music? it's not too cold, you know, AC's not too high, and just good people, like first degree, second degree kind of connections. And I've worked out of WeWorks. There's a lot of value in weworks, but it's not my vibe. It feels very cold. It's not where I want to hang out and like be productive. And so I thought a lot about, okay, what would, you know, I'm calling a weekend cafe kind of naming after like weekend fun in my head. What would weekend cafe look like? And obviously there's some like basics, you know, maybe an open space with a bunch of phone booth, so you can take calls, especially as more people are working remotely.

But now more recently I've been thinking, well, how can you actually innovate on the business model? And of course, my mind goes to NFTs and Web3 as kind of one kind of thread to pull on. And what we're seeing more and more of is people releasing utility NFTs or subscription kind of membership-based NFTs. And, you know, the most obvious and basic kind of like application of that is now you actually have better price discovery theoretically for these NFTs. So an example could be Weekend Cafe has 100 seats, 100 membership slots available. It's really small, it's intimate. And the people that own the NFT, one of the 100 NFTs, get access to this space. But you can resell it and you can, of course, have like on the secondary market,

the actual business itself, in this case, like, let's say me, gets like secondary transactions, like 10% of those cuts. That actually is interesting because you might find that actually Weekend Cafe is very valuable. And actually it initially was sold for $100 per membership. Now it's $10,000 for some reason. It's just interesting to kind of think through, okay, what would that look like? So I'm curious if you have any thoughts on this or other innovations in that model. So I like, I've seen and talked to a few people that are kind of doing variations of something like this,

like social club or, you know, like the Soho House of Web 3 type vibe. Or like Gary Vee has this hunt and fish club, I think it's called. and similar stuff. My concern with it fundamentally is always like, how do you prevent this from just being, you know, the wealthiest people buy into the coolest things? And you like prevent it like it actually goes to being less cool because suddenly it's like not the curated environment and group.

It becomes more like business and capital and money in the same way that like Soho House was super cool when it started and they were very careful about who was in and it was more artists and designers. And then it became really finance. fancy and like all of a sudden every banker in the world was a member at Soho House and it probably got less cool because they got more corporate trying to make money to go be a public company. So my question is always like my pushback on this is always how do you avoid it just becoming that like rich people kind of buy these NFTs and are able to go to it when they become

you know, one, two, three, four, five, Eth to go to go purchase. Two thoughts. So first thought on that piece, Sahel, I think what you can do is just make. make it the initial batch free to mint and you could have something like some level of like you know

maybe you want to keep the the first batch diverse in some in some way so there is some you know asking some questions up front but ultimately you know people think that you know getting an NFT is always you know they in their minds they think of board apes

and stuff like that but it doesn't always need to be that case for example the number one project right now on OpenC is a Freedom End project, Goblins Town. So I think having a Freedom in component is very interesting in this. So it, and by the way, Ryan, it could also be hybrid. Like maybe you sell, if you do 100, maybe you do 50 freedom mint and you sell 50. The second piece of feedback I would have is, so first of all, I'd love this concept. I think Miami needs it more than any place that I've been.

to. And I think what would be really cool is if you can reward long-term holders and good actors of the NFT. So one of my favorite projects in the NFT space is a project by Dom called Corruptions. Corruptions is basically this NFT that the longer you hold it, the more it changes. And it basically evolves. And in the smart contract, there's basically this like, it's basically built into it. So I wonder if you can do something similar where if I become a good actor, if I, you know, I hold it, the NFT changes. I get certain privileges because of that. And the other sort of analog that I also would love to implement it to something like this is the last week I've been really into bowling. Don't ask why. But and the bowling alley I've been

going to has this leaderboard of people who've bowled perfect games 300. I wonder if there's stuff like that you can do where it's like imagine you bought a coffee for someone every day and for 30 days maybe you're on some sort of leaderboard. So I also wonder if there's like fun gamification type things that you can do. Yeah. Actually one note on the the corruptions concept. So the moonbirds projects have been in the proof uh, collective project have been following from the beginning moonbirds has this nesting concept so i have a couple of moonbirds i got them because i have a proof collective pass from the beginning and when you nest them every 30 days it like levels up into i think it goes from like bronze to maybe silver to gold

to diamond or something like that and what's kind of interesting is um as you sort of level it up the the actual nfti itself carries as the tributes going forward so once you unnested it stops that that that leveling kind of progression, but you still maintain the status of that particular NFT. And so as you sort of hold on to the NFT longer, it gains in more value and has more abilities or prestige in the community over time that you can then sell. So it's kind of like in a video game when you level up like a World War craft character, you know, to level whatever 100. It's a level 100 when you want to like give it to somebody else still. And I find that concept compelling because it really rewards people for holding, but it also rewards people financially,

theoretically, in the future if they want to sell or liquidate in some way to the buyer. So, yeah, I think there's a lot to play with there. And I think video games can be a great source and inspiration for all those ideas, too. Basically, how do you take what we do in video games and apply it to these types of dynamics? So if you want to start a weekend cafe together, let me know. I know. I was kind of like, maybe there's actually something to it. There was one that this guy started called Maxwell Social.

I think in in New York that I saw recently. That looked like it was going to be pretty cool. We'll see if the build out happens. And then I saw another one that's sort of around like an athlete, former athlete community network that's a former NFL player that I know that's starting. But some cool stuff going to happen in the space for sure. I just want to see it actually play out and not become like a highly, you know,

like, I don't know, exclusive community that just like wedges people out. Any final thoughts, guys, before we wrap? I know we've taken up our hour of time here. This was awesome. I feel like we hit on a bunch of really interesting things and threads within a single conversation. Yeah, anything on your mind, Greg? Anything?

I don't know. I didn't come really prepared with anything formal. So I just wanted to jam and chat. That's the best way. Yeah. I mean, the last thing, my last question for you while I have you is, are you happy are you happy you made the Miami move? Because you were, you know, almost the poster child for San Francisco at one point.

And we, and, you know, I moved from San Francisco also to Miami. And I'm just wondering, are you happy? Are you happy you made the move? I am. So I grew up in Oregon, then lived in San Francisco for 10 years, L.A. for two, and then Miami, it's been a year now. I am. The thing is, I mean, I've always worked remotely. ProductNet was distributed. So for me, even though I live in Miami, I'll be in New York later this week. I'll be in L.A. in July. I'll be in Tulum for a wedding the next month. And so for me, it's Miami just, it's just one of many places I live in, I suppose. I'm here most of the time. But it's good. I mean, there's certainly some downsides. You know, summer hurricanes are a little rough. We had a lot of rain a few days ago. It was insane. But, you know, waking up in the morning, without. out like the pressure of, you know, West Coast like rush is nice. Some of the nightlife here

is amazing. I love warm weather. So I'm a fan. What is interesting, though, is I, to be honest, I think more investors are here than founders. There's a lot of talk about like people from tech coming here and I don't have any hard evidence or data on this, but there aren't a lot of founders here, which is fine because I don't meet founders in person. I just go over video, but I don't know if you've noticed that, Greg, but it doesn't feel like there's a substantial number of founders, you know, in the tech circles over here. I agree. I'd love to do more, like, we should do some sort of like event or something.

And when I say event, I don't mean like a thousand person event, but like 10, 15, 20 builders in a room, jamming on ideas. That'd be fun. Yeah. I just feel like. This is why we need like a cafe, a space, because there's no shelling point right now. I think that I'm aware of. Maybe I'm just not invited to one that exists.

but we don't have like a space to just meet up and jam and co-work and that kind of thing so yeah you wonder whether it'll be like and if you build it they will come type thing with the founders like now that more of the investors are there you know and as things go back to in real life which hopefully they do because I think it's a good thing in a lot of cases you know you wonder whether more founders will choose to build there because it's just the proximity and your access to capital will be very real yeah so it's good spot it's good time is it's great I I will, I will, absolutely. I know I'll be back down there come, I'm going to wait until it gets a little less muggy probably, but I will be back down there, you know, maybe in September. I'll look forward

to it. Well, thank you so much, Ryan. This was awesome. Really enjoyed the chat and we will talk to you soon. Yeah, thanks for having me. See you guys. Later. Thanks so much for listening to today's episode. If you have any questions that you want featured in a future episode, email us at high at t-R-W-I-H.com. Leave us a review at Apple or Spotify to help us grow the reach of this podcast. Until next time, we will see you soon.