The Pomp Podcast - #274: Alexis Ohanian on Building and Investing in the Modern Digital World

Episode Date: April 20, 2020

Alexis Ohanian is the Co-founder of Initialized Capital, a half-billion dollar early stage venture capital firm. He is also the Co-founder and Executive Chairman of Reddit, one of the most popular web...sites in the world. In this conversation, Anthony and Alexis discuss the founding story of Reddit, what Alexis learned as a Partner at YCombinator, whether he has ever beat Serena at anything athletic, what industries should benefit from behavior shifts due to the virus, and what org structure and internal tools allow Initialized to operate at such a high level.  =============================== BlockFi allows you to keep your crypto, put it up as collateral, and receive a USD loan funded directly to your bank account. They do loans ranging from $2,000 to $10,000,000, and they're perfect for helping you reach your financial goals of all sizes. Visit BlockFi.com/Pomp to learn more about putting your crypto to work without having to sell it. ===============================  Blockset by BRD is your hosted blockchain infrastructure. Blockset enables enterprises and developers around the globe to deliver high-quality blockchain-based applications in a fraction of the time, at a fraction of the cost. Using the services provided by Blockset, businesses can build professional custody solutions, accurate and near real-time portfolio management solutions, auditing platforms, commercial block explorers, and much more: blockset.com ===============================

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Starting point is 00:00:00 What's up, everyone? This is Anthony Pompliano. Most of you know me as Pomp. You're listening to the Pomp Podcast, simply the best podcast out there. Let's kick this thing off. Alexis Ohanian is the co-founder of Initialized Capital, a half billion dollar early stage venture capital firm. He is also the co-founder and executive chairman of Reddit, one of the most popular websites in the world. In this conversation, we discuss the founding story of Reddit, what Alexis learned as a partner at Y Combinator, whether he has ever beat his wife Serena at anything athletic, what industries should benefit from behavior shifts due to the virus, and what organizational structure and internal tools allow Initialize to operate at such a high
Starting point is 00:00:43 level. I really enjoyed this conversation with Alexis and I hope you do as well. Before we get into the episode though, I want to talk about our two sponsors. The first is BlockFi. You guys know that I love them. They've been longtime supporters. I'm an investor and a user. They currently have three products. The first is giving US dollar loans against your crypto as collateral. The second is an interest bearing account for your crypto deposits. And the third is allowing you to buy or trade cryptocurrencies. They also will be coming out with a Bitcoin rewards credit card later this year. The Bitcoin rewards credit card is just a normal credit card, but it pays you in Bitcoin rather than cashback or loyalty points. It's going to be dope. So head on over to
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Starting point is 00:02:11 or Bread, the first wallet in the App Store from 2014 and one of the largest in the space today. They've taken the architecture and knowledge they've gained over the past six years to create Blockset, a robust, reliable, and strategic B2B offering for developers and enterprises. Thanks to Blockset, we can all build with crypto assets at light speed using their unified API that has data from all the major chains. See just how simple it is by visiting Blockset.com and sign up for a free account today. Go build. All right, let's get into this episode with Alexis.
Starting point is 00:02:39 I hope you guys enjoy this one. Anthony Pompliano is a partner at Morgan Creek Digital. All opinions expressed by Pomp or his guests on this podcast are solely their opinions and do not reflect the opinions of Morgan Creek Digital or Morgan Creek Capital Management. You should not treat any opinion expressed by Pomp as a specific inducement to make a particular investment or follow a particular strategy, but only as an expression of his opinion. This podcast is for informational purposes only. All right, guys. Bang, bang. I've got Alexis here, basically the president of the internet i think uh based on what some folks were never elected i was never
Starting point is 00:03:18 elected they're teasing me because of a forbes article from way back where they said mayor of the internet mayor it's better to be the president not president just just a humble mayor of the internet i love it i love it let's um let's just jump in uh to the background obviously uh i think people in tech know the story of reddit and all that but uh lots of people listening don't know that story. So maybe let's start with kind of where you grew up and how'd you get to Reddit? Sure. I mean, I was a history major at the University of Virginia back in 2005. And I was getting ready. I was taking the LSAT actually. And I walked out 30 minutes into it because I was hungry for waffles. And I went to the Waffle House on Route 29 in Charlottesville, Virginia,
Starting point is 00:04:06 was sitting there eating my waffles instead of taking the LSAT. And I realized I should probably not be a lawyer. And with that, realized I needed to do something and started kicking around some ideas I'd had for starting a company and convinced my roommate to quit his job in order to come work with me for some indefinite period of time working on some ill-defined thing without any sources of real revenue guaranteed. We were going to like consult on the side. I managed to convince him. His mom was pissed, but I convinced him to turn down the job offer. And then we were lucky enough to be in Boston on our senior year spring break. While everyone else was going down to Mexico, we went to go hear Paul Graham give a talk called How to Start a Startup.
Starting point is 00:04:52 And Paul Graham would go on to start Y Combinator and invited us. Basically, I approached him after that talk and said, Hey, I want to pitch you on this idea. We came all the way up from Virginia and he said, sure. And he met us for coffee, pitched him on this idea. It was a way to order food from your phone. It was 2005. Uh, but the whole idea is you can skip the line, but you don't have a smartphone in 2005. You just had text messaging and it was, it was a lot of ugly hacks, but, um, he saw enough potential to then launch Y Combinator encouraged us to apply. Uh, we got rejected, uh, which sucked cause he, we just had a great conversation with him. And then the next morning he called back and and I was like hello and he's like look we still don't like your idea
Starting point is 00:05:33 and I'm like dude why did you call me back to say that like that's not that's not helpful at all and he said but we'd like you to and if you're willing to change your idea we'll fund you and I was like I need to think about that because you got to play it cool in that situation I was like okay I'll call you back and and we were convinced we were like somewhere in Connecticut we got off the train we got rid of the old idea which was called my mobile menu or and and called them back. And I was like, we will accept your offer. And back then it was $12,000 was how much YC gave you to start a company in 2005, which was amazing for us. And we got to work. And that is what became Reddit. In that first meeting, when we took the check, Paul said, don't build anything
Starting point is 00:06:18 that involves a phone right now. And he was right about that. It was too early. But he said, build something in a browser that solves your problem every day and he said what do you do every day and and for me it was i'd open firefox which was a big deal open a bunch of tabs and and just read a ton of different content and and that wasn't very efficient and and he actually asked this he asked us if we'd ever use delicious and this was a social bookmarking site basically pinterest without pictures if if yahoo acquired them pretty early it was all text-based very programmer focused but it was people bookmarking interesting links and so back then it was like tips for ruby on rails and and those would get bookmarked and the most popular bookmarks would surface on a
Starting point is 00:07:04 page called delicious slash popular and that was we had never used it before and he said take a look at this and he was like what do you think about this and we were like oh that's kind of interesting like maybe there's a there's a there there we know opening starting your day with a bunch of tabs wasn't the right move um and there could not be a front page for the internet in the way that there was a front page of say the new york times and that was something i give credit to paul for phrasing he was like that's it he crystallized on it build the front page of the internet um he screwed a lot of other things up like he tried to talk me out of the name and the mascot uh and commenting uh but thankfully we didn't listen to those those tidbits uh but but
Starting point is 00:07:47 he nailed it with front page of the internet that's what we sought out to build in 2005 we sold it in 2006 to con and asked which at the time felt like i was winning the lottery like we were working for 16 months and it was a 10 million dollar exit which was life-changing it was more money than my parents have made their entire lives and i worked for 16 months on this thing like in my underwear, like that's, that's broken. But, but in 2006, we just didn't know. We didn't have the advisors. This was the impetus. I mean, really the impetus for Gary and I to do initialized was to be the early stage investors that we wished we had had when we were in the trenches, um, so that we could avoid a lot of those or founders, future founders could avoid the
Starting point is 00:08:27 mistakes we made. And, you know, I went on, I wrote a book, I helped launch hip monk. I was partner Y Combinator and then started initialized with Gary to do this kind of early stage investing and, and then got the chance to come back to Reddit in 2014, uh, when it was in pretty dire straits, um, as executive chairman and helped lead the turnaround for the next like three years, four years. And, um, you know, Reddit's gone on to raise funding, hundreds of employees doing really well now. And I moved back into the board role, uh, board only role. So I could go back to initialized full-time which is what i'm doing today so that's my life in uh 10 minutes i love it uh most people don't know this i don't even think you know this uh we are actually uh small
Starting point is 00:09:11 investors but investors through an spv in uh in reddit um when you guys did the uh the turnaround uh round oh great the first outside great oh good on you man big uh big fan um but in terms of when you uh the condé nast and when you guys sold the company the first time yeah i think this is like a classic situation where founders are like, holy shit, I built this thing and somebody's going to buy it from me. Like how dumb are they? It was stupid. Yeah, it was just, it was stupid. And we didn't, I mean, I cannot stress this enough and I've never really told this stuff publicly. It was, you know, every startup is dysfunctional in its own way. There's always a million fires and you're always just sort of triaging and prioritizing best you can. And we were not far into Reddit's
Starting point is 00:09:58 life and we launched it in june and then less than a year later i remember in april because my birthday is in april um i was i was in touch with the head of bd business development for conan ass this guy karosh karam khani who had reached out because we had a mutual friend who said hey you should check out this reddit thing and uh and he was making overtures about potentially working together an acquisition and and at the time we just weren't we weren't making any progress uh shipping new features the site was just still growing kind of miraculously and and and overall like the advice we were getting from our investors was oh my god that could be an acquisition offer like go pursue it and and i was basically told like your best bet alexis is
Starting point is 00:10:47 to get this company sold and i mean we we had not raised much money at all after yc demo day we raised uh 70 grand i think 60 grand so we we we thought that was a ton we actually turned down an offer to raise uh i guess it would be a seed round of a million dollars back in 05 after demo day we turned it down because we said we don't need that much money because we weren't even thinking about like hiring people it was so dumb and and so we didn't have much money but it was fine our burn rate was super low and and we were not doing any of the right things to actually grow business and here was this offer our investor explicitly was like alexis go try to get get anything you can um i was actually able to reach out to and eventually we worked our way up at wpni
Starting point is 00:11:35 so washington post newsweek interactive and we actually got really close to an acquisition offer by them um but they would not match condé Nast's exorbitant price and and so we ended up going with condé and and yeah it seems bonkers to me for 16 months worth of work for a company that really wasn't shipping any code for the last few months um would would be able to get acquired but they saw potential credit to like stevie newhouse karosh um the ones who ultimately did the deal kind of asked like they saw the potential even when we the founders who were closest to it didn't and uh you know kudos i mean i'm i'm grateful that i got a second chance um and a lot of founders who sell early don't get that so i know i can i'm very very grateful for that but this is exactly
Starting point is 00:12:22 the kind of thing we we we want to help founders with during these early days uh that we just didn't get when gary and i were starting yeah at some point did you have almost like seller's remorse like like when did it hit you you're like shit we might not we maybe we shouldn't have done that uh so no yes and no like my rational brain probably uh by 2010 or 11 once so I stepped away in 2010 um February of 2010 and I went to go went to go to Armenia went to go to the motherland to go volunteer for Kiva for a few months and and around that point I just thought you know what like all things considered uh this this site keeps growing and it's probably worth more today uh than it was back then and then it really clicked by like 2012 where i was like oh my god
Starting point is 00:13:23 this thing is still growing and like nothing has changed like there's no business especially in tech that should be able to get away with not evolving and yet it did right reddit didn't have a mobile app until 2015 we launched the mobile app and it was a big like it was steering the titanic over to make mobile a priority whether it was mobile web or android and ios um but we did it and and it was like credit to all the folks who got it done but once i realized that like wow this thing just kept growing because the community because we got just enough right in the product just enough right and then the community really did everything to sustain and grow it that's when I was like oh geez wow that we really messed this up but my my my rational that rational brain
Starting point is 00:14:11 usually gets drowned out by the I guess it's the more rational or the more stoic part of my brain which is like look everything you have had from this point of selling it happened because you sold it then and so look at all the amazing doors that open to you look at all the amazing things that happen to you and yeah it'd be a different timeline but uh like i'm pretty pretty happy with with how things are uh quite happy with how things are and so i've just tried to look forward from it and obviously learn from it and know that it was a mistake but not dwell not dwell on it i just i've i've tried to always live my life looking forward that way to the best of my ability and so i think part of it's just being delusional but uh just trying to have that 24-hour memory and and keep
Starting point is 00:14:56 keep keep going forward that's what makes it fun uh when'd you meet gary uh i met gary when he applied to y combinator in 2008 or 9 um he was applying with his company posterous uh which was so back then it was a marvel because you didn't really have smart you didn't have smartphones i don't think that order you were just starting to and so you had phones with these really good cameras on them but it was a pain in the butt to get uh the photos off and or there was no app store that's what it was yes so there's no app store really developed yet no ecosystem for that and it was just coming on and so you could easily take a bunch of photos and then email them to an address an email address and magically a photo blog would appear and it was really clever
Starting point is 00:15:40 software um i i gave him a thumbs up so he continued into yc and uh and then he became a founder while I was a kind of advisor there. And, uh, and then within a couple of years, he had sold the Twitter and was back at YC as a partner. Uh, and then I was sort of back in the orbit as like a part-time partner that eventually a partner at YC. And, uh, you know, I ultimately, I could have been a partner sooner at YC and Paul and Jessica very graciously offered. Um, but I think you'll appreciate this. I said, I didn't want to leave New York and like i just didn't want to be in the bay area for for that extended period of time now here i am in florida so i you know i still i got i got pulled out of the city but but my heart is still
Starting point is 00:16:26 very much east coast at least and i i spent time working alongside gary and a bunch of the other partners working with you know accepting and then supporting yc companies for a number of batches was just like was just was floored by how decent and thoughtful gary was as well as bright and hard-working and all those other things but like incredibly decent and thoughtful and how much great founders gravitated to that uh especially in the bay area where there's just so much bullshit and and i actually think it is it's such a superpower not just because it is rare which already makes it valuable but also because it attracts the right kind of founders and and it's provided us this amazing orbit of just high quality just great individuals that we get to help
Starting point is 00:17:18 build companies with yeah when you guys decided that you were going to go and start initialize and kind of invest together outside of YC what was that conversation like did one of you kind of propose to the other one or like asking out on a first date or what was that like you know it was it was not very deliberate um we were we were both so all the yc partners at the time and i think still this day were angel investing so like you know they write a small check to the company as the end of the batch they liked and we were doing this we were doing it pretty well and um someone approached i think it was gary or actually might have been harge and said hey would you take like my money uh to invest in addition to your own and and we were
Starting point is 00:18:06 like huh and it was like yeah like you can write pretty small checks no offense because you know you sold so early uh but like if you if you take other people's money uh you can write bigger checks and and start to have even more of an impact helping these companies and and maybe even build something greater than just you all angel investing and uh and then i don't know we must have been having drinks one night or something and it came up and and i i said yeah that sounds great what a good deal and and really the first two funds have initialized were um basically just an extension of our angel investing and it wasn't until fund three which we launched in it was 14 or 15 that it was like formalized like okay we're gonna take real institutional money we're gonna
Starting point is 00:18:54 we have this team, we're going to build software to actually run the firm and really do it like deliberately, sort of modern initialized as I call it. I didn't start until then. Yeah. I always love that switch or that decision to go from, hey, I took like my friend's money to the institutions, a whole different ball game. And I think that there's a lot of fund managers that don't build the software, they don't build the systems. And then they're like, wait a minute, you want to report like every quarter and you want like to know how much money you have with us? It gets real. Yeah. And I feel like we have such an inherent advantage just because as founders, we are product people. And so we're, I mean, even to this day, only a
Starting point is 00:19:36 few years in, we'll look at anything that comes up that we have to do that is repetitive, that is sort of tedious. And that becomes top of mind on the product roadmap for things that we can either automate or build software to do so that we can better spend our time and our team's time doing the things that humans are really good at so that we let the software do the the other stuff and it's not like it's a black box where it's like tell us to invest it's like remember all these things it's like manage the deal flow generate the reports like this is tedious work that humans suck at that humans shouldn't be doing and if a partner wastes a minute of her day doing like that's a minute that's not helping the firm actually make money and that's that's what we
Starting point is 00:20:23 want software doing yeah makes a ton of sense what um what makes kind of the partnership work i think a lot of people realize like you gary some of the other partners like you guys are very supportive of each other both publicly and obviously seem to have a very strong relationship outside of romance you're referring to the the bromance yeah it's like what makes that work uh huh what makes the bromance work well you know hard conversations uh being able to and this is the thing this is why we're so long on coaching generally executive coaching i mean everything coaching therapy like all things exercise of the mind and relationships uh something we we try to prioritize and really speak and live those truths ourselves i mean as well as physically
Starting point is 00:21:10 too um that maintenance mentally and physically is so important and a big part of that isn't just personal it's also interpersonal and it takes work just like any relationship takes work whether it's romantic or professional like that it's it's an investment we have uh two on two sessions gary and i do with our coaches um regularly at least quarterly um just to review all the other mini sort of one-on-ones that gary and i try to regularly have and as well as one-on-ones with our respective coaches um and so one it's acknowledging that it's all a work in progress and i think the the big takeaway that we look for in founders now and really push them on early early early is so you have to have the complimentary skill set and that's the tried and true like of
Starting point is 00:21:59 course yeah this founder does this this one does that we're complimentary but the the next level of that in questioning is, is actually looking for where or how much the Venn diagram overlaps when it comes to things like values and worldview. And, and that is a thing where I've, I've had founder relationships. I've, I've been very close to a lot of founder relationships and portfolio companies where you see that breakdown on the long-term values. And, and that, that starts to, I think that is the core problem that that only services later during the harder times. And, you know, during the early times, the good times, growth solves all problems. You don't really, it doesn't really come up,
Starting point is 00:22:44 but the hard times when they come up, when they, and they always will is what services when there's those value worldview differences. And it's not to say one is better or worse, but if you don't have alignment on those things that matter, I think that is where a lot of the tension, like that's where things start to tear. And so I'm fortunate because Gary and I both see the world as plus some. We don't think that someone else's success means less success for us. We don't have that zero sum mentality. We try to espouse that within the partnership. I think the people we've been able to attract who want to be here have that. And we've tried to orient the org toward not a bunch of lone wolves, which is the standard VC idea, but actually a wolf pack because that's how wolves are supposed to be anyway.
Starting point is 00:23:30 But really using software to be a means to have that collaboration happen so you aren't getting information hoarding, you're getting information sharing. So whether a company is doing well or poorly, and again, all companies have problems all of the time. What's important is that they're good at triaging the most important ones as fast as possible. And so we need a culture of information sharing because there's someone on the team who can actually help that company with that problem or someone they know who can help. And we need as much of that to flow as possible. It needs to start from us. And I think that begins with a plus-sum mindset of, like, we're all economically linked within the firm, but more broadly, like, we need to be looking at every opportunity as something where we can grow and learn from and have, in addition to that, this kind of growth mindset. and then also know that we are more effective as a team than than any one of us even gary or i
Starting point is 00:24:31 could be alone and and software frankly helps dictate a lot of that culture just because it is so transparent all of our updates are seen by everyone you can see my meeting notes i just got off the phone with a reporter my notes from the meeting are in there they're tagged it's all structured data um you can see the companies that i talked about you can see the trends that she's interested in um like that lives there for anyone to see and and like i don't want to hoard that i've been i've seen environments where i'm just like why are we hoarding this information like this is not like some reporter's email address is not uh sacred like no like why are you hoarding this as if it's like you're precious like no no like we're better off the more this
Starting point is 00:25:15 get shared. Yeah. And I think a lot of this is, uh, philosophy, right. In terms of like, literally, uh, you go into organizations and I've seen it, especially the older organizations and the people just, their philosophy is I have my fiefdom and you're not in it. And therefore, if I let you in, then I would lose and you're going to win or you're going to take my business or, or whatever. Um, and so how do you guys kind of one fight back against that? And then also two, how do you structure the team itself in order to, uh, kind of encourage the collaboration, the openness and that communication that's needed to to prevent it i mean we are still figuring a lot of this stuff out we we want to show i i think we very much want to lead by example
Starting point is 00:26:03 and so a lot of this i mean we actually have an internal leaderboard which tracks um very competitive uh which tracks uh folio notes across the different items and and I make it it's my personal goal to always be number one there and and Gary and I are always fighting it out but but I want to demonstrate to the org that like we like we expect to be using this thing as much or more than everyone here like we we this isn't a scenario where we as founders of the firm are above like leaving meeting notes like on the contrary this is actually really important because i have my own intuition we all have our own intuition that we want to be manifested in those notes and those hunches and and and so we want to do the work we want to show that we're
Starting point is 00:26:54 doing the work as well um but we are look i mean we're still only a few years really into the experiment and you know things are tracking well for sure but it is about bringing on um people who also fit into that culture and and we've really i mean i i always go back to um uh this is going to be very controversial but i always go back to to sports metaphors for this stuff and and i do appreciate the system mindset of belichick's patriots now we'll see how they do in a post brady era but but i do appreciate the mindset of finding people regardless of of sort of talents or egos or skills that just need to be able to fit in a system. And if they don't, you know, bye-bye. But I think,
Starting point is 00:27:45 I think there's a way venture has been done historically. And I think folks who have come up with that mindset have not, well, we just, we haven't even had them be a part of the team and be a part of the org because we just knew it's not a fit for us. We would rather find people who are expert. So like Brett, right, has founding experience, has massive technical experience, just personally fascinated with and pretty deep on all things crypto. Did not have a background of early stage investing, maybe a couple angel investments when he joined us a few years ago. but like that's the part that we can train up like that's the part where you just got to get your reps in you you sit you be in enough deals meetings you see enough of this stuff you start to see the trends that's just hours and gary and i put in a ton of hours doing angel investing and
Starting point is 00:28:37 yc investing and so what we need are the raw materials of do you have the expertise do you have the like can you sit with a founder for 30 minutes and that founder is like oh holy shit that was really valuable if you check those boxes we can build up the reps on the early stage side and i mean you know a company like um bison trails uh which is doing very well right that was a deal that brett sourced in part because of the reputation he's built over the last few years in crypto but then also the fact that he could sit with those founders who want to talk to him and say yeah this is real and and and and source that and identify that and find that um and and i just like having i i we're still early in it but having this system mentality and being able to get all
Starting point is 00:29:27 the benefits of software which is the structured data that i mean we have you can find notes from the first time you met a founder three years ago know exactly what you were thinking as well as like how you rated that interaction one to five uh and see which of your assumptions were wrong and which ones were right and every vote not just the score but also how you qualify it so that we can always be learning and letting software do the hard part of like basically remembering things and helping us identify trends so i i'm i'm cautiously optimistic it's funny how software does a better job of remembering things in the human brain right yeah no i look and and more importantly it's transferable knowledge like i if um so i don't want to ever have to remember
Starting point is 00:30:14 that i just had actually i don't want to ever have to remember that we had this interview like I do I don't I don't want to purge it from my brain but I I shouldn't need to remember it it will live in structured data in software that will forever be searchable so that some intern in two years will have a record of it that they can search for they don't need to slack me and be like hey Alexis you know pop you ever you ever done that podcast they don't they shouldn't that's a waste of my time it's a waste of their time they should be able to run that query in folio which is our internal software and see the entire history of that relationship and those notes and all those things because it's just not worth it's not worth remembering and it's also inefficient
Starting point is 00:30:59 because it's still locked in my brain i don't want it locked in my brain i want it locked in to a broader network that anyone can search into yeah well not anyone but anyone in our in our trust group uh in our in our company can search well so you guys are capitalists uh why not license it to either other firms or uh go build a whole business out of it uh we've been asked that um we have been asked that mostly by lps uh i don't i don't know how i mean competitive firms probably wouldn't um i wish they could come and come ask it's okay but uh well one i don't want to be in the business of like i i don't want to be the business of having cost customers for software anymore it's really nice to only build software for like a couple dozen people as opposed to
Starting point is 00:31:44 hundreds of millions of people it's so much better and and i know ultimately i also think that it won't work as well for other orgs unless they really build their culture for it from day one like i i and you've heard enough horror stories of larger orgs trying to implement some great software solution and there's no participation there's no one willing to do it because they've just had so much inertia that it would take a massive cultural change to actually get the orgs to use it but for up-and-coming orgs yeah maybe there's a business and a viability there but i don't want to be in that business yeah what uh what's the biggest mistake that you think you've made uh in building initialized or like the biggest lesson you learned uh from when you
Starting point is 00:32:26 started till now? Biggest lesson learned the, Oh, Oh, that's okay. Yeah. So the, the, at the end of the day, um, because we're doing such early stage investing, the ownership sizes were something that, you know, even at the start of modern initialized, um, we weren't ambitious enough with what we were targeting and we're, we're, I mean, we're leading seed rounds now. And I, I knew in my heart, I knew at the start of initialized that we could do that, but we weren't, we, we, we didn't execute on that. Um, and, and I think, I think part of it was just not wanting to miss, right? Higher concentration just inevitably means you're going to have to be right more, uh, cause you're going to get fewer chances. but um but have i wish i had that confidence at the start of it uh or at least started yeah at least more confidence in that regard because we would have targeted more ownership earlier um but the good news is we've we've increased that with every fund and um we're in a better
Starting point is 00:33:33 place now but that was the big like math lesson especially because we knew we were doing the work like we knew we were providing value because our investors were our founders were telling us like oh wow you're doing like you all are way more helpful than our lead investors and we heard that enough times that we were just like, why are we just doing this? Why are we doing this work to help someone else? And so that was the number one, definitely the biggest lesson. Yeah. And I guess did you, that really get hit home because you saw the math play out? Like after a couple of years, you actually said, Hey, wait a second, we own way less of that through all the dilution than we wanted to, or was it the conversations with the founders? It was both. We had an inkling
Starting point is 00:34:10 over time as founders would report back like, Hey, you know, this is more helpful than our lead investors. And then a few years out, we're like, well, wait, okay. The founders are telling us that we're doing the work and providing, you know, providing value. Uh, but we're actually doing the work and, uh, and we're not getting rewarded for it, but we could be. And why not solve that problem? So we, we solved that problem, but that was, um, that's definitely the, the, the first biggest mistake. Yeah. One of my favorite questions to ask, especially early stage investors that come from uh the the operator side is uh do you have one hilarious story early on when you met with the more institutional lps where you guys just walked out of a meeting you're
Starting point is 00:34:51 like well that either didn't go well or you guys just kind of laugh about now and say like remember when x happened don't say who it is yeah no i won't say who it is uh we had i almost feel a little bad and and so i'm gonna the story is actually not that great but the macro story is one where i actually feel a little sympathetic which is these professionals like i mean just default assume they're smart competent hard-working people they have to look at and evaluate so many different asset classes and tech venture is still such a small part like i mean globally in terms of dollars like we're nothing right but it's obviously the most exciting and the best um but it's it's it's got this black box
Starting point is 00:35:40 where i can just i can see them getting hoodwinked by people who like i have no respect for whatsoever just because they don't know it's a small percentage of the portfolio so there's not that much downside and you know especially on the early stage you don't have a lot of signal right you don't have years worth of data this is just a weird very weird asset class and um and so i just i think the times when i when we walked out of those meetings just shaking our heads it was usually because those investors just didn't know what real was and and maybe they just didn't appreciate co-founding and you know turning around reddit uh maybe they just didn't appreciate our track record of early stage investing. Maybe they just didn't get why, I mean, we were fair,
Starting point is 00:36:33 I think we're still, I don't look as young now, but fairly young looking folks were trying to start a VC firm because they were used to seeing sort of stately or older folks coming in the door. I don't know, but I do, I mean, I remember being asked, like hammered on valuations as if this was like value investing 101 and i'm like at the end of the day dude like it doesn't really matter like we need percentage ownership like this is super early stage investing we're making up valuations most of the time anyway because there isn't revenue so like i mean come on but but they were i think they were new to the asset class one of the things somewhere along the way there we learned was to ask early even before the intro like what what's your experience with venture investing what
Starting point is 00:37:23 your experience with early stage venture investing in particular um because you can run into some folks not i mean these days less so um but certainly in was it 11 or 12 when we were first um talking to folks about initialized like there were there were plenty of folks who just had family office types especially just had no idea what the asset class was about yeah you know everything looks like a nail when you got your hammer and we'll get to crypto there's a lot of parallels there i think yes oh that's that's a very good point very very good point we uh before we get to crypto uh serena um there's lots of people who have uh that's all people wanted that's all people wanted to talk about they're like reddit whatever talk about serena i always laugh
Starting point is 00:38:04 because uh um every time that uh polina does anything on the internet and i'm around everyone they say shit about her and i'm like wait a minute like she's the star right and i feel like so when i saw the uh questions on twitter one of them was uh people were basically asking you got to tell the story about wearing the dare shirt to the tennis match because that's probably that's an all-time move i i think it's really important to acknowledge all of the harm that the dare program as well as the war against drugs did on a generation and and i just chose that day to wear that shirt to to remind everyone of that that's a uh speaking of speaking of this stately venture capitalist you're you're getting conditioned right i mean i listen you just happen to wear
Starting point is 00:38:57 the shirt no problem or total coincidence uh another question this is a polina question is what was it like going to the royal wedding and uh and talk about the socks i wow y'all are going in today all right uh i mean i was a history major right so i just loved i especially loved the fact that i felt like i was like it i was a part of history in this very historical setting um you know i i was grateful to be there had a great time wore u.s flag socks that i made sure the camera saw as we were doing our little walk um i don't know hopefully that was that was just the right amount of civil disobedience right i i i really appreciate a number of these things that people brought up because i feel like it is reddit in real life right like just just enough
Starting point is 00:39:50 of uh seriousness but just enough of kind of the trolling and like we just want you to know we can be disobedient if we wanted to be yeah i guess i'll forever be the the sort of uh the i guess on some level always be the reddit co-founder in my heart i love it and last the last serena question is uh you are married to uh probably one of if not the greatest athlete of all time you can prove that probably nonsense have you ever beat her at anything athletic like racing to the car jumping jacks tennis anything no never tennis come on be realistic i've never i've literally never played tennis in my life so it's actually very very fortuitous I didn't even think it was a real sport until we started dating and then I was like okay it's a real sport now I actually I
Starting point is 00:40:38 love it it is such an intense sport I grew up playing team sports my whole life and so I never appreciated solo sports and in my household like football and basketball were the only two sports so I was ignorant and the amount of mental and physical strength it takes to play professional tennis i mean it's it's that i would say i'd put it up against like ufc boxing those two others it's like the only other in terms of mental and physical extreme because you're alone you are alone out there and the physical exertion and then more importantly the mental exertion on top of that that that separates the greats from everyone else is just next level um but i've never played it never gonna play it uh i'm actually if olympia if i i promised olympia if she's into it then i
Starting point is 00:41:25 can be a really good like baby instructor until she gets like actually capable and then serena will take over and you know and then i'll play a couple matches with olympia until she's like five and then she'll wash me when i was a kid uh my mom for whatever reason took me and a couple of my brothers and said you're gonna go to this tennis camp and we played baseball football basketball right kind of similar style and i remember we made it through one day of the camp and they asked us not to come back because halfway through the day well we just realized like look we're not good at this this like takes actual skill so instead when they hit the ball to us let's just see who could hit it the farthest out of the yes yes and i feel like that's kind of like
Starting point is 00:42:08 if you don't grow up with the skill of you know learning tennis that's pretty much what everyone else does just hit it as hard as you can and just hope it goes somewhere near where it's supposed to yeah no that's that's the realness and so definitely i would never try to play tennis against her um physically there's she i have some advantages based on uh one my height and my size uh as well as like those childhood sports so like i remember the first time i saw serena uh shoot a basket or try to and no no it was no seriously that is that is god clearly being like that's what you get for talking about your wife playing basketball uh i gotta talk to gary about why this happens because this it's good we can we'll we'll be edited all right all
Starting point is 00:43:02 right i mean but seriously what anyway um but yeah she's she's not not good at all at basketball so like there are things if we were playing a game of horse yeah i'd wash her or one-on-one but like this is not it's not fair because you would not take i don't know you would not put a formula the best formula one race car on a demolition derby track and expect it to do well and like so yeah so there are some things where i and it's actually it's especially nice because i get to feel like i beat an olympian which i'm deluding myself entirely right it's it's nonsense but in that moment it feels nice and it's also quite humanizing for her too um i i think i mean she's obviously amazing uh the the the reality is her moments of normalcy only make her moments of
Starting point is 00:44:00 greatness even more impressive like she's still a klutz she's still her baking's actually gotten really good recently if you've seen the cinnamon roll updates like she's still terrible at shooting a free throw and those things actually make all the other stuff even more exceptional um and it's also a good reminder that like all of us are are with our flaws uh and um but nonetheless i mean yeah she's the goat so i don't hear any of this i don't hear this this one of i will uh i will defend that one of my day i love it i love it um you've uh you guys have obviously made a ton of investments um across a whole spectrum of uh of trends and and industries what specifically are you guys looking at right now as uh whether it's kind of coming out of the covid crisis stuff or
Starting point is 00:44:46 just before we went into this this is the thing that uh you guys are interested in uh i it's gonna look prophetic but it's not we we ended up i mean companies like row and true pill in telehealth are are doing very well and poised to continue to do so, um, in, in the wake of this. And excuse me, it's not a, um, I think it is, that is one industry that I think is, is going to be very good for business as well as for society, because what people are realizing is that at a minimum they can get great, uh, they can get a great form of healthcare on demand for you know nothing uh thanks to this technology thanks to smartphones and at a minimum that helps reduce yeah and i'd be remiss if we didn't talk about crypto during all this man
Starting point is 00:45:40 i obviously you know we were early investors in coinbase that that has done well tell me about that deal well you found it through y combinator yeah and and actually this is i mean this is like initialized lore so um you know then we were basing this gary to his credit was was early and dabbling in bitcoin um i would just see it talked about all the time on reddit and i was like all right well if enough people on reddit are engaged and interested in talking about it there's at least this early adopter signal which is powerful especially for something as technological as cryptocurrency and um we we we basically and i remember there's an email exchange where we were like oh this valuation is a little steep um but thankfully we were just like it doesn't matter
Starting point is 00:46:28 it's just if this if this is right this will create such a new economy and they will be like the premier bank for the west of of crypto like that's it's valuable um but the part that's initialized lore was and i forget i think bitcoin had jumped to maybe like four or five dollars and they were running out of working capital coinbase was every morning by like 9 a.m just because they had so many people on the platform and and brian and gary were having one of their sort of regular like coaching sessions slash lunch sessions like every month and brian was like yeah this is my problem. And Gary was like, that is a good problem to have. We can help. And so we gave them a round of funding to help sort of bridge them to the Series A, which I think USV ended up
Starting point is 00:47:16 doing. And, you know, that investment alone was incredibly valuable for the firm, even more so than the initial check, because we basically doubled down when we saw that there was real, real demand here and um you know it's done well for us and so we've been thoughtful um about it we didn't get caught up into the ico craze nonsense uh which was good um really just treated every crypto investment as like a delaware c corp and um and really we're looking for the same product things that we look for in any company and and a lot of it was around infrastructure um whether it was like coin tracker uh for helping with crypto taxes um bison trails which obviously was the most recent investment uh about running secure infrastructure on multiple
Starting point is 00:48:02 blockchains um well i guess technically atomic loans is the most recent uh which we did together um which like is an economy of lending that just couldn't even have been conceived of uh some five years ago and and what's exciting now is that there are enough sort of incumbents in the space uh especially on the mining side with bitcoin that like there's clear economic need here and let's use software to fill it and so we're still i i i don't know when it's time to call crypto spring because i keep talking about it and i just like i i think the winter was so important to get rid of the charlatans and not all of them but be able to get rid of a lot of them and get people refocused on solving real problems and, and actually help
Starting point is 00:48:49 bringing this into the mainstream. The part that still confounds me is that even during these times of volatility where the market still makes sense and the printing machine goes, uh, I, how does one actually say that? Cause I just know the meme and I just read the text, but I don't actually. So you're ready. I, uh, I don't know if this is correct, but I literally walk around now, whenever i see a headline and i just go oh that makes more sense than my burr like it's cold listen i don't know if it's right but i just for whatever reason decided that's what i'm gonna say no that well i because i don't know what a money i realize i don't know what a money money printing machine actually sounds like but it probably sounds like that one
Starting point is 00:49:28 the dexterity of that one but like that it still it confounds me because uh i still i mean i'm still along i still hold uh bitcoin some ethereum and some other uh god damn it you know why the video just went out because they don't want to hear about anything bitcoin the fed is angry at me i i actually think this might have overheated okay hold on i'm i got a new plan i got a new plan uh let me get my i'm gonna crank up the ac in here all right uh oh poor baby you're running hot all right i've got some serious feedback though for uh gary tan when we talk about the setup i don't know how he keeps it he probably he probably has a nice temperature in his home got that 90 degree south
Starting point is 00:50:25 florida weather and i was trying to keep okay how bad is this background noise now that the ac is gone oh well you see i should have done this from the start okay um but i keep i keep waiting for um bitcoin to to surge again because it feels like this can't i mean i think it's important I do think it's really important we're making these cash infusions and I wish they got they got to Americans and the small businesses that needed it not like say airlines but uh but I just can't help but feel like this will just further expedite the growth and acceptance of cryptocurrency broadly but but especially bitcoin and the trick is like is it now too much of a just kind of investment uh or has the infrastructure not been built yet to make it
Starting point is 00:51:20 really seamless to spend spend spend it as easily as like usd but i'm still like the we're still making investments on the infrastructure side we just announced brett was the lead partner on the series a for a horizon uh which is uh it's ethereum backed but they're building the game technology for digital assets like a playing card in a video game you actually own right this is this was so pilly to me as someone who grew up playing magic as well as spellfire the dnd knockoff of magic and then eventually hearthstone and then looking at the fact that like i spend all this money on digital goods that i don't actually own like this just makes sense for a generation of gamers who are spending real money now if if we were in world of warcraft going on ebay to buy or sell
Starting point is 00:52:10 characters or or actually buy gold from gold farmers overseas remember that and then having them meet us in the digital world to arrange the drop-off if that was happening a decade ago then there's clear right if there's if there's that level of contraband and sort of illegal black market happening then then surely if you bring it into a frictionless like great market environment it's going to thrive and that's the bet there with skyweaver at least as their proof of concept for horizon but i i really believe this infrastructure is getting built now and has been built for the last few years by highly technical product-minded founders who are thinking about user experience we're thinking about building things people actually want
Starting point is 00:52:55 and now it'll be another five really it'll be another five years as we watch the fruits of that get built um and scale which will be exciting uh really really good i mean i you know i really trusted you sony i trusted you to make a product that would not die uh okay so so on the crypto side uh obviously you guys uh reddit has announced or or rumored uh the erc20 token what are these rumors eh well here's what i'll say is uh i probably more than most understand there's certain things you can say you can't say etc maybe just talk about kind of crypto within the reddit system why something other than bitcoin was bitcoin ever considered you know just kind of whatever you're comfortable saying there so i i have to unfortunately keep very mum about this
Starting point is 00:53:49 um what i can say is the thing you know we we had had reddit the company had had some forays into crypto and some of your twitter people had remarked on this when i came back in 14 as executive chair there were some forays into it but it was mostly still research um we had much more pressing things to handle at that point um much more pressing things and like for instance we didn't have a mobile team or plan or anything like it was more important in 2014 that reddit have a mobile app and a mobile website and that we were building towards that for instance um but uh i have always believed the long-term value of reddit is not going to come from traditional from advertising it will come from the fact that we've already done the hardest
Starting point is 00:54:40 part we have managed to build a platform that handles tens of thousands of communities and hundreds of millions of users who truly have a sense of community and belonging with one another and we know and a lot of this was inadvertent frankly like we didn't have a grand vision in 05 to do this but we we watched it happen and i had a front row seat as we were like i was the first community manager for our first 10 communities i would just post links under different usernames and and moderate uh submissions so everyone stayed on sort of task and subject and we've watched whether it's digital goods and gaming right i want to buy a skin so i look nice for myself and for my friends and for strangers right there's no i mean there's a small tribe
Starting point is 00:55:28 there of like people you know and then people you'll randomly sort of shoot and walk away from in the video game um but on reddit people are people will buy pizzas for strangers people have such a much stronger tribal spirit and community spirit that if you could take the best lessons learned from digital goods and gaming uh things like tipping on twitch or patreon and provide uh a very seamless digital transaction for that it will happen it will happen a lot and like even awards the first version of reddit awards i modeled after uh the awards at the end of golden eye where you'd have some that made sense and then you'd have these others like random like rcp90 award i forget there was some random and like we didn't really have i don't even know if we ever
Starting point is 00:56:17 looked it up we would have used hotbot i don't know we wouldn't have googled it back then but like we we liked i mean as gamers we really like this idea of oh you get this award if you do certain good things over the course of a day and i was just v1 and i was like 2006 so before any of this award stuff gamification any of that stuff was a thing we did it just because we were copying goldeneye and what i wish we had done was double down on it back then because what we're already seeing now even with small modest improvements to awards that users love giving them to one another they love subreddits communities love creating them it reinforces this tribalism and the more that we can do to help communities and users
Starting point is 00:57:01 strengthen their relationships to one another and make money in a way that they're happy with like the more we win and and it just seems like a logical transition then if we know i just gave you the horizon experience with skyweaver right if we know this stuff works where you don't have any ownership whatsoever and it's a massive industry and growing it reasons it reasons to be that if you allow for a kind of ownership and and a kind of decentralization to it that people would do it even more because they could feel all the feels we get when we you know take a cup and say hey do you want this cup here you go um so and then it may not not have this cup anymore of course and so i i wish i could tell you more about it i love the fact that there
Starting point is 00:57:52 is this much energy here and and i do think long term a big part of my job on the board especially right now while you know reddit's traffic like every ugc site is booming we can reasonably all expect marketing dollars to soften and and so now is the time for companies like reddit to double down on revenue streams that are like this that are accretive that are things that build on community dynamics that actually add value to everyone involved and and and as to the sort of traditional models of marketing, um, or at least, you know, remove our reliance on them, uh, as a business. Yeah. I love it. Um, there's a lot of questions about, uh, you know, you kind of have this great journey to where you sit today. Uh, but early on, you know, it was like, Hey, look,
Starting point is 00:58:45 we want to start a company. Uh, we kind of have an idea. Oh, that idea sucks. Okay. Like here's another one, right? Um, what's your advice right now to college kids or kind of kids coming out of high school, especially given the macro economy, the virus and around, you know, what skills should they be developing and kind of how should they be thinking about their careers, you know, over the next two, three years? Sure. I, I mean, I realized a lot of people watching this are like this guy, this guy's married to Serena Williams. This guy co-founded Reddit and initialized really, really first investor in Coinbase. What? And, and I get that. And I appreciate that. And I want, I want you to take away from that, that there is very little
Starting point is 00:59:29 that one can plan for in life. And so my guiding principle would be, I actually was supposed to do a graduation speech that I think is moving digitally now. So this is, this is a good kind of beta test for it. Focus on the things you can control and, and, and work as hard as you can to improve on those things, get better at those things, and then spend as little time as you can dwelling on the things you can't. And that's sort of a general kind of COVID economic macro situation there. But in particular, if there are things that you love doing that don't feel like work, but are viable things in a new economy, do more of them. Really, really focus on those things um because that is the best path to a a great career one that gives you fulfillment whether
Starting point is 01:00:20 or not that ends up being you know fabulous riches is not as important as like having the fulfillment of a job that is not going to get automated away and that will give you satisfaction and and provide for you know hopefully a family or even just for yourself um that's the stuff i would focus on and i think there will be a generation of high school students that will now think twice or their parents will also think twice about taking on the student loan debt of going to a lot of universities. I don't, I don't think the top tier schools will have as much to worry about because there's still so much credentialism and network and brand and whatnot, but there's a lot of schools, um, that don't, this is going to sound terrible, but don't have a really unique value proposition that don't
Starting point is 01:01:05 have a clearly articulated value for the very, very expensive tuition and the crushing inescapable student loan debt it would give, that I hope we can learn from what I think were well-intentioned mistakes, encouraging everyone to go to college as a path up, and instead say, all right, let's have a critical, serious look at what you enjoy doing, what you want to do, and consider an option that just makes the most sense. And so I've tweeted about this, and one of your folks asked about it i would love to see a reimagining of trade schools a kind of i think part of it's rebranding it just simply like having a kind of um you know we we were early investors in general assembly which was one of the early kind not quite coding boot camp but type of sort of like a
Starting point is 01:01:55 community college 2.0 with very modern skills being taught by actual practitioners some version and beautifully branded and just felt very premium. What is the general assembly of skilled labor? What is the version of that for welders? Of these professions that we know are in tremendous demand where the average age of the people doing it is I think in the 50s, maybe like upper 40s. But this is a generation that's getting ready to retire
Starting point is 01:02:23 with no real replacement, but for jobs that are still desperately needed. And even in a time of increased automation, there are so many tasks that just won't be automated automated away easily because of all the physical and mental complexity and creativity required to solve them and and that's the fact that like building a robot that can come in to this office and go figure out what's wrong with my toilet is really really hard it's really hard and and for for the foreseeable future at least as i believe it plumbers will not get replaced the welders will not get replaced
Starting point is 01:03:01 there will be software and systems to make their jobs less repetitive right they're just like we do in initialized we're going to automate away the things that require memory like extreme memory or planning or scheduling like the things that humans just suck at and don't get fulfillment from anyway and let them focus on the parts that are creative that are physical and sort of very specific um that are valuable and and so i think i think we need to tell a generation of kids look if you're gonna end up just being a history major at the university of blah because you want to spend four years you know going to college because that's the thing to do reconsider it and and if you like working with your hands or if you have um if you have interests and passions outside of
Starting point is 01:03:51 like the sort of general like oh yeah i want to go to college to have fun and party um there should be way more affordable paths to getting a really valuable education even in the new economy and then the like the cheat code which is the thing i mean i went to 82 universities when my book came out in 2013 82 universities across the u.s and canada telling people if you're at all interested because you're already in college now like if you're at all interested in learning to code do it please like like just take the class even if you don't like it great you are exposed to it that is the cheat code for the new economy if you want the like it is not i guess unlike a cheat code it is not easy to accomplish it takes work uh it is not a trivial skill to learn let alone
Starting point is 01:04:41 to master but like please like that is a path into a kind of job security that is if you enjoy it incredibly fulfilling both spiritually as well as financially um and and now that has expanded beyond engineering to product design um we're seeing even amidst all the layoffs right now in for instance the bay area um so much of this talent is getting scooped up by the folks who are sitting at the table with a bunch of chips who who have the cash and now have an opportunity to hire even more great talent and so you know i it's unfortunately it is not as simple as saying like do what you love like that's that's just irrational i don't think great advice um but putting more of a point on it if there are things you really enjoy doing where you can lose hours
Starting point is 01:05:33 working on them and they don't feel like work um and they fit those criteria that we just talked about where it's the kind of work that's not going to get automated away like that is probably a really good path for you to keep going down and uh and i think remote learning all this stuff is going to see a huge bump coming out of this uh overall i've got a friend actually he uh he started buying up uh and kind of rolling up uh electric electricians simply because he said not only are electricians not going to get automated away he goes the schools are so bad that we're actually churning out less of them and therefore become more valuable you know over the next 5 10 15 years so if i if i manage to fund trade school 2.0 then i'm actually hurting your buddy he'll be
Starting point is 01:06:13 fine trust me he will be just fine but we need we we we so need this and and i think one of the good byproducts of the the isolationism that i think we'll see in the next 5 to 10 years is it will recreate or it'll resurrect a self-reliance culture which i do think is a good thing and i think with that will come more scrutiny on oh yeah look at all this infrastructure we've let go to waste here in the greatest country on earth right and that will that will reshift the mindset around a lot of these trades that will that will change some of the broader culture around it and help do the help do part of the work but we still need that reinvention of the actual education programs to your point um but i do think that's a silver lining i i it it does
Starting point is 01:07:05 hurt my heart that we will see such a big shift inward in the next five to ten years because i really do i'm the child of an immigrant uh my mom was technically undocumented for three years because she overstayed her visa which is how most undocumented immigrants get into the country btdub um you know she overstayed her visa for a few years and thankfully ice didn't toss her out um and she married my dad and while i'm here but like it it does hurt my heart because i really do appreciate so much that we gain from this open flow of information and ideas and humans i really like our food in america would be pretty whack as if england is any indication uh right england benefited the uk benefited tremendously from a flow of immigrants who really leveled up the
Starting point is 01:07:59 cuisine there um like if nothing else my fellow americans you should appreciate immigration for the fact that it has made our food so great here in america and um and so yeah there's there's a part of me that definitely it's going to sting to see this closeness that i think we're undeniably going to be heading toward the next five ten years um i hope we can make up enough of that with things digitally i mean right i think this will also ironically then give rise to more and more of these decentralized type networks that can thanks to you know in in most countries uh that can transcend uh sort of national blocks um but uh look i just want i want to see the best ideas win and i know that the best ideas don't all come from the united states and i know that
Starting point is 01:08:45 opportunity is not universally distributed even in our own country and i just want better things And so that's the, that's the sting of it. But I do think one of the silver linings of that self-reliance will, will actually make us stronger as a country. I love it. Uh, three questions to, uh, to wrap up with, and you could ask me one, uh, to end it. Uh, ask me anything. You, you are a new dad. What is the, uh, the one thing that, uh, you either enjoy or have learned that you did not expect, uh, before you became a dad? Well, you've got to listen to my podcast business dad season one is out now no uh the biggest thing that I've learned it put into perspective how how I don't see how horribly I lived my life before I found out I was going to be a dad
Starting point is 01:09:34 but like at 34 35 I found out I was going to be a dad and and I just it it was perspective building man i really i wanted to get better i wanted to be better about the things that i ate the things that i drank things that i smoked the amount of exercise i did the just taking care of myself by even seeing a doctor like i i felt a new appreciation for my own mortality and a semi disgust at how little i cared and how much i lived for myself up until that point um and and so i i know in so many ways it has made me a better person because i now evaluate everything through that and and through that legacy and through that role model that i'm providing to her and i'm still still messing up all the time but as a north star it has been so much more fulfilling than i mean i
Starting point is 01:10:29 felt i felt really great about starting reddit i felt really great about all the work we've done with initialize like there's so many ways that we keep score in business that are all kind of made up, but they're good. We're competitive people. We need that stimulation. Right. But it put all of it into such a perspective where I was like, this is this little person. She, she matters more than any of this other stuff. This family unit matters so much. And, and I think it has helped me. It's definitely made me a better man. And I wish I could say just meeting and, uh, marrying my wife did that. And that helped. It absolutely did, but not even, it's just a very different level and I'm sure she would say the same thing like yeah meeting you Alexis marrying you Alexis
Starting point is 01:11:11 was great but the thing that really changes everything was was was was having Olympia so I um I'm not encouraging everyone to go out and make babies right now though there there will definitely be some quarantine kids by December uh that's for sure but but I do I I'm I'm so grateful for the opportunity to be her dad uh it's awesome that's awesome and I think people can you know see it right and just uh kind of the way that you act and things you saying stuff so i think it's really cool i mean i still do dumb stuff let's be clear like and that's the other thing too i i also get really self-conscious about the fact that i am not a perfect dad like and i don't i we we all have myself included we all have stories that we
Starting point is 01:11:52 present to the world and i should just post more photos of olympia being sad she's not as cute of course because she's she makes a face though that's kind of cute because she's like her face gets really flat and it's her sad crying face and it's it's it's adorable but um right i hope i hope the takeaway can be and i should do a better job of this with the pod too i hope the takeaway is like look this is a work in progress and i i just even from talking all these different other business dads the best the the common thread between all of them is is they're all very accepting of the fact that they're just trying to figure it out too and and they're picking and choosing and learning and adapting and and you know we're we're screwing up all the time just
Starting point is 01:12:35 like in our startups we're just hoping the trajectory is up and to the right uh with our children too i love that i love that what uh what's your favorite book ever other than the one you wrote my favorite book ever okay the controversial one that i i really i enjoyed a lot more than i thought i would was um uh winner winners take all which is not my favorite book of all time at all but um i really of the books that i've read in the last like year i really appreciated that one for giving me a dose and a perspective that i think i rarely get and i want i i and i don't know how this is going to turn out because i know i'm sort of responsible for this with reddit but social media has done an amazing job letting us find our tribes as well
Starting point is 01:13:25 is discover new tribes we don't even know we had and i think overall that is amazing right we get to learn about crypto together with people from all over the world who humble us and teach us and all that's awesome um it also means it's easier than ever and this is like version two of like the filter bubble that they were talking about years ago it makes it easier than ever for us to then isolate ourselves and not want to be subjected to ideas that make us angry or at least uh challenge our worldviews and then there's a fine line there because i think there are some ideas where it's perfectly reasonable to be like that's a terrible idea like that's a bad thing um but but there's always this nuance that i worry will get lost as we get better and better
Starting point is 01:14:06 at finding our tribes and so i try to make an effort to find and read things that challenge it i don't do a great job of it but i do from time to time find that and you know when i think of when i think of like a universal thing like book that i actually would recommend to anyone um you know one of my favorites uh my one of my favorites might be this book drive about human motivation and incentive um just because it's guided a lot of the ways that i think about product as well as community which are the things that everyone seems to ask me about when it's about investing or startup advice and um human incentive is still something that we don't fully understand and maybe we never will um but i am just i'm awed by it because on the one hand
Starting point is 01:14:59 sometimes it's very rational other times it is incredibly irrational um but there is actually some reason to the irrational stuff and i think all the times that i have had success as an investor, especially at early stage, really just comes from paying attention to these trends and being a better observer than like prognosticator. Like, I don't think we're particularly good at predicting the future. And I don't, I certainly know we can't do it in a bubble. But if you can get really good at identifying trends and looking for signal amidst a lot of noise and, you know, reading reddit every day for a decade and a half has helped um you can find it and i mean that's the the magic right now is covid has exposed the strength of the fifth estate where um so thomas
Starting point is 01:15:54 carl i was history major right right he talks about the fourth estate as media being a check against the three estates the three branches of government both government and the media showed a failure to really prepare us for COVID-19 and and those are the two institutions that historically like bounce each other out and have all sort of the the trust of the nation in one one pocket or another but but it was the fifth estate social media that actually really was ahead of this I mean that's that's the reason I like I I felt like Cassandra talking to investors or portfolio founders in january some of whom right didn't really believe the advice because they were trusting one of those other estates just like no no it's not a big deal and and that's only because
Starting point is 01:16:41 i followed the right people on twitter it's only because i followed the right people and i had a couple partners at the firm who are also tuned in but what does this new world look like as the fifth estate gets stronger and stronger and as individuals you all are each one of you are developing your own media brands and and and i don't know what the accounting of that is going to be but there's real value in being able to show being right early in a way that like you know 100 years ago it was subscriber counts of a newspaper what does that look like now i don't think it's necessarily youtube followers um perhaps there is a great blockchain based way to to to show this i don't know but um i'm excited for it i'm also clueless as to how it's going to
Starting point is 01:17:29 turn out because as humans we just i mean this is a little sapiens so i know i'm doing the vc thing but like we just really don't have a context biologically for this much data like our tribes were really so they were the people we could walk around or walk to for a long time and and we only got mass communication what last 100 years travel uh 50 years like we're still figuring this stuff out and now we can go online and i can see what someone had for breakfast in seoul i can i can see real-time images for how uh you know they're handling covid in mumbai i can see opinions from literally all over the world in real time and i think paul was prescient when he said there's there needs to be a front page of the internet.
Starting point is 01:18:19 I think Reddit has now built multiple front pages for the multiple internets, the sort of multiple tribes. But I wouldn't say that that is the accounting of the internet. What is that going to be? Because the answer for that is going to, I think be really valuable in years to come. Because especially if you're in the business of trying to make money or trying to understand where the future is headed,
Starting point is 01:18:44 like it is going to be really valuable to know where that signal is. and uh i don't know how that's going to play out but speaking of uh humans third question are you believer in aliens i think they're real uh i think it is possible like are you asking me do i think that they've visited not visited just yeah oh i think if the if the universe is infinite it then which i believe uh then i think that it is plausible that there is alien life uh it might not be impressive again i mean you're asking a tech guy this question but like i i don't think it could be i think it could be like a you know a single-celled organism but it's still an alien um do i think it's like a xenomorph from alien uh hopefully not but maybe um but i so i so i
Starting point is 01:19:42 guess the real answer is i don't know but i could imagine so yes yeah the thing that's terrifying though right is if they can we've now explored enough of our galaxy that if they can get here then their shit is going to be magic relative to what we can comprehend and so at this point i'd rather not find out unless we're the ones visiting them i think that's the best way to look at it is at least here on earth the people who usually invade some other place or usually end up being the victor right now let me check this out right i wish and there might still be a chance but i really wish covet 19 would be our like independence day moment as a world because this virus doesn't care about any of us it does not care about how much money you make or your race or your gender
Starting point is 01:20:35 doesn't care about anything just wants to make you sick and make other people sick um i really hoped it could be the independence day moment i'm looking for the jeff goldblum and will smith to uh save us uh or some way help us put aside our differences and unify and we're seeing it in pockets uh but maybe you know the special effects budget of covet 19 is just not great so it's not very compelling you don't get to see giant spaceships hovering over massive cities but i wish we could think that way i really do because i hate covet 19 it uh it sucks it sucks is a great way to put it what uh one question you have for me to uh to finish this up what what made you want to invest in atomic loans
Starting point is 01:21:21 um i'm just a big believer and i've gotten over this a couple of times so like the whole idea of you've got sound money in bitcoin or at least the properties of sound money uh but all of the infrastructure for the most part uh is centralized around it um so whether it's the coin bases the gemini's the block fives etc some of it we're invested in some of it we're not uh if you look in the like ether uh ethereum world you get uh what they're trying to make money like eth is money meme and they're trying to do it but the infrastructure is decentralized so like you almost get like decentralized sound money that has centralized infrastructure but then you get decentralized infrastructure with something that looks kind of like a fiat currency to something
Starting point is 01:22:04 with eth and so you got to bring those two decentralized components together the money and the infrastructure, the big question is, do you bring Bitcoin to the ETH world or do you bring DeFi to the Bitcoin ecosystem? And I tend to think you're going to bring the infrastructure to Bitcoin rather than bring Bitcoin to ETH. Highly controversial. I've had a million people come on and, you know, bitch and complain and basically say that, you know, I'm an idiot and all stuff, but that's just kind of my general thought process. And then ended up, you know, you guys were investing um and uh made sense right on well excellent i'm glad glad to be cooking with you in the kitchen on that absolutely where uh where do you want people to go to find out more
Starting point is 01:22:46 about you or initialize you can follow me on the twitter at alexis o'hannion um or instagram if you're into that i assume twitter is going to be the move for for your crowd and then they should go to initialize.com obviously if they want to learn more about the firm um that's it i don't have a sound cloud not yet awesome man listen i appreciate you doing this is a ton of fun i know a lot of people wanted to uh to kind of hear what you guys are up to and uh i'm a big fan uh obviously anybody who's starting a company should uh should go check you guys out and uh and convince you to give them some money like uh like atomic loans and many others right on uh thank you very much for having me sorry we couldn't do this in person but you know so it goes covid sucks yeah covid
Starting point is 01:23:31 sucks hashtag covet sucks all right thanks man likewise all right hey everyone pop here if you like this episode of off the chain and want to help us take crypto to the top of the apple spotify and other podcast charts please do us a favor and rate review and subscribe to review simply go to the off the chain homepage scroll down until you see the five blank stars taking 15 seconds to fill those stars in and leave a quick review goes a long way in helping us take the entire crypto ecosystem to the top of the charts. I appreciate you listening and see you next time on off the chain.

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