The Twenty Minute VCNick Tomaino: The Future of NFTs, What Will Happen with FTX & Who Should be Held to Account | E1076
EVERY SPOKEN WORD
140 min read · 28,041 words- 0:00 – 0:25
Intro
- NTNick Tomaino
The people that got sucked into this perception game that FDX was playing, the, you know, the politicians, the regulators, the investors, they all now are trying to just sweep it under the rug and say, "Oh, I didn't know about this financial fraud." It wasn't just a financial fraud, right? It was a fraud of perception which they all played a role in, and I think ultimately, like, people will realize that.
- HSHarry Stebbings
Nick, I am so excited
- 0:25 – 10:21
Coinbase & Early Crypto Adventures
- HSHarry Stebbings
for this. I saw your Tweet, and I replied like, "Man, this would be such a good show."
- NTNick Tomaino
Yeah. (laughs)
- HSHarry Stebbings
I'm so thrilled that you agreed to do it with me, so thank you so much for joining me.
- NTNick Tomaino
Thanks for having me, Harry.
- HSHarry Stebbings
Not at all. But I want to start with a little bit of, kind of two origin stories really. One is obviously how you found crypto for the first time, and then obviously is on the fund. Just take me back on the crypto side. How did you first find crypto and come to join Coinbase?
- NTNick Tomaino
So I've always been an internet person. Like, in middle school, I was really interested in sneakers. I was, you know, buying and selling and collecting, uh, Jordans and Nikes, and, uh, I played a lot of basketball, so I was super into sneakers. I was spending a ton of time on Nike Talk, which was kind of the early sneaker head forum. I've just always kind of been in- gravitated towards the internet. Um, and even more so than, like, the, the, the physical world around me in some ways. I think I'm kind of unique in that sense, where, you know, when I first heard about Bitcoin, it was this, uh, Wired article talking about this magic internet money that was being used to buy guns and drugs on Silk Road, right? That was kind of the early media narrative. And if I asked the people in the physical world around me, you know, what they thought, um, like everyone else at that time, they would have thought it was stupid, and they would have told me not to spend any time on it, right? But I, uh, wanted to see who was on the internet talking about this, um, and I stumbled across, uh, Bitcoin Talk, which was the first, uh, online forum, uh, for Bitcoin that was created by Satoshi Nakamoto, the, the founder of Bitcoin. I saw on Bitcoin Talk that, um, you know, the media narrative is one thing, right? Talking about this, you know, magic internet money that was being used for illegal stuff, and, um, but, but the reality was very different. I saw kind of this community of people from around the world. They weren't aligned by physical location, but they were aligned by shared belief system and economic incentives. After spending some time, uh, on Bitcoin Talk, that's kind of what led me down the rabbit hole and, uh, ultimately decided I wanted to make a career out of, uh, out of the space.
- HSHarry Stebbings
And you did make a career out of the space. You joined Coinbase, and then you take the decision that actually, "I'm gonna switch sides of the table from operating to, to venture and investing, and I'm gonna found One Confirmation." Can you just take me to that moment of transition and why you decided to do One Confirmation and why then?
- NTNick Tomaino
Well, frankly, I mean, I got pushed out of Coinbase. Like, I, I wasn't a great, um, employee, I think is the truth. I think I did a lot for Coinbase in the early days, um, but I wasn't... Coinbase got to a certain point where I wasn't great at kind of office politics and following rules and directions and stuff like that. Um, and, you know, at the time, uh, you know, I, I technically, um, you know, left, and it, that was how it was framed just to the company and things like that. But I, I effectively got pushed out, and at the time, that was very painful. Um, right? That was probably one of the lowest points, um, in my career, I would say, because I believed so much in both the space, uh, and the company, um, and I put a lot into the company as well. Um, I think it was, uh, a great thing ultimately, because it just, it wasn't the right fit. But at the time, I was like, "Shit, what am I gonna do now? I love this space. I know Coinbase is gonna be a billion-dollar company. Um, did I just fumble the bag? Um, you know, what, what the, what the hell am I gonna do next," right? You know, it was at that point that, um, you know, I decided that, uh, that venture would be, uh, you know, what I could be world-class at. At Coinbase, I was really good when it was just, uh, you know, a few people figuring shit out. I had, you know, really good ideas, um, and I could just do stuff. And then once you get within a big company and it's like, there's all this bureaucracy and stuff, that's not what I'm good at. And I thought, "I know the space really well, um, and I, uh, you know, I think I see what's going on, and I understand products better than anyone. Why not start a fund to invest and help the founders that I'm, uh, investing in?" And that's kind of what happened with One Conform- that's how One Confirmation came to be, I guess. There was obviously a lot of other stuff, but at a high level.
- HSHarry Stebbings
I've, I've just been thinking about how to phrase this politely, uh, in my head.
- NTNick Tomaino
Oh, you don't, you don't have to be polite. You don't have to be polite.
- HSHarry Stebbings
Okay, well, then respectfully, you were gonna... I, I'm really sorry, by the way, for you being pushed out of Coinbase. But respectively, it also made you who you are today, which is very, very successful, so congratulations on that. I often think sometimes the hardest elements can shape you. But no offense, kind of pushed out of Coinbase and then raising a $26 million fund? Like, that's quite a big jump, Nick. (laughs)
- NTNick Tomaino
Mm-hmm.
- HSHarry Stebbings
How, how does that happen? You either have a lot of rich friends or... I mean, a lot of rich friends, or how, how did that happen?
- NTNick Tomaino
(laughs) No, I don't, I don't have any, uh, really, you know, I didn't have any really rich friends, um, I don't think. But, you know, I ha- had built a strong personal brand while I was at Coinbase, and I think that helped a lot, right? I wasn't just working at a company. I think a lot of peop- to me, like, working at Coinbase, it was more than working at a company. I was, like, working for an industry, 'cause um, you know, crypto was very, you know, early obviously when, when, when Coinbase started. And, and Coinbase was kind of leading, um, you know, the industry in a lot of ways. Um, and I didn't... I, I wasn't like a Silicon Valley person that just wanted to work for, like, a brand name company or something like that. Like, I genuinely believe...... uh, and still believe that, you know, crypto is the most important social technology of our lifetime. And, you know, I, I was going to do anything that I could to, to help it grow. That was kind of my mindset. It wasn't like, you know, "I'm working for this, you know, brand name Silicon Valley company," or anything like that.
- HSHarry Stebbings
Was it easy to raise that first $26 million?
- NTNick Tomaino
(clicks tongue) Well, what, what, what helped in between was, after Coinbase, I ended up joining, uh, Runa Capital, which is a venture fund. Um, it's not a super well-known venture fund, but, um, really good Russian entrepreneurs that had founded a, a few multi-billion dollar companies that, you know, were investing, um, in mostly, um, like, SaaS, enterprise SaaS companies. But they were also curious about crypto. So, I joined Runa. That was kind of my bridge, while also doing a lot of stuff personally, right? So I wa- I, I was, you know, I got into venture th- through Runa, but I was also, you know, like, I started a newsletter, um, called The Control at the time, where I was, um, you know, I was writing about the space a lot. Um, I also, uh, founded, um, an event called the Token Summit, which, um, i- if there's early kind of crypto people, they'll, they'll know. Uh, Token Summit is kind of a legendary event within crypto. Uh, it happened right, um, before kind of tokens kind of took off in, um, in 2017. And it was kind of all of the best founders from around the world, um, in the space coming together to talk about, uh, to talk about tokens and crypto. Um, and, you know, it was really cool. We, uh, uh, it was a 400-person event. Um, and there was so much demand that tickets were selling, um, on Craigslist for, uh, like four times the price that we were selling them for. So, this was a really, um, you know, big event at the time, and I think it was a lot of what I've learned in, in my career is like, you know, you need to be at the right place at the right time. It's like timing, uh, uh, for, for both entrepreneurs, for venture, for whatever it is, like, timing is really important. And I think you can ... It's not luck. You, you can, um, kind of use your, your knowledge and learnings to assess, you know, what, what a good time is, right? But timing is important, and I think there were a lot of things that kind of came together for me. What, it was Runa, it was Token Summit, it was me continuing to believe in crypto and kind of build a brand. All that came together to help me, you know, raise, as you asked, how did I raise a $26 million fund? That was kind of how I was able to do it.
- HSHarry Stebbings
Dude, 2015, I started th- you know, 20VC way before podcasting and venture were cool. Just as kind of two years in, venture became cool. Three years in, podcasting became cool. It was total luck on adoption cycles of both-
- NTNick Tomaino
Yeah.
- HSHarry Stebbings
... really in terms of mainstream media. So, I totally agree with you there. Um, that's fascinating.
- NTNick Tomaino
Well, but I don't think it was- I, but, but I think saying it's luck is, um, may- may- maybe selling yourself short. I mean, you were curious about, um, you know, what was going on in terms of content creation on the internet, and you were, I'm guessing, an early consumer of podcasts and that helped and so-
- HSHarry Stebbings
Oh, yeah. Like, years before. Like, 2009.
- NTNick Tomaino
Yeah. I v-
- HSHarry Stebbings
Yeah, no, 100%. Okay. So, if we, uh, play this game. If you were to put luck and skill, which would you say, if you were to put numbers against it, your success is?
- NTNick Tomaino
I think it was about n- 90% skill, 10% luck. I think it, it's, it's, um, politically correct to say, "Oh, it's, it's, there's a lot of luck." I think a lot of really successful people say that. I feel like I made my own luck in, in a lot of ways. I feel like I had a lot of bad luck that I, uh, persisted through. It was my, uh, determination and kind of grit, um, more than anything, and that, that is a, that is a big skill. I think having that ... It's not skill in the sense that I'm, you know, smarter than everyone else or, or anything like that, but I think, uh, determination a- and grit, and belief. Um, you know, at the end of the day, I, I think belief, uh, having self-belief, um, is
- 10:21 – 22:36
Financials & Raising Capital
- NTNick Tomaino
a skill. Again, it's not saying I'm smarter or, or, or things like that, but it's, uh, it's like ha- having these unique traits that I think anyone can have, but, but you need to have belief first and foremost, so ...
- HSHarry Stebbings
I think, it's like being an entrepreneur. It's persistence. It's going through the shittest-
- NTNick Tomaino
Mm-hmm.
- HSHarry Stebbings
... of shit days and coming back tomorrow and saying, "Today could be different." Uh, can I ask you, I'm just too interested. What was the worst luck that you went through that you persisted through?
- NTNick Tomaino
Yeah, I'm talking about some things I haven't talked about, uh, really, really publicly. But I was working, um, at Coinbase, um, but still in business school. I had all my money in, uh, Bitcoin, uh, on Coinbase, right? And that, that's how much I believed. Uh, like I, I ba- I basically, uh, you know, emptied my bank account, um, put it all in, in Bitcoin. This was before Coinbase had, uh, two-factor authentication, right? Um, everyone knows now that, you know, if you have a Coinbase account, you have a password that secures your account. But also, you know, you, you're using Google Authenticator or Authy or, or two-factor. Literally, like two weeks before, um, Coinbase added two-factor authentication, there was a fairly sophisticated, um, phishing attack that, on, uh, a number of Coinbase employees, um, and, um, other people associated kind of with, with Coinbase, and I was one of them. So, I, I remember, uh, you know, the morning it happened. I was like, um, you know, groggy. I was in, this was when I was in business school at the time. You know, I was groggy from a night out or something and woke up, um, got an email from what, what, um, you know, appeared to be a Coinbase, um-... email, but it, but it w- wasn't. You know, I, I wasn't careful. And at the end of the day, it was my own fault. But I basically got phished. Um, I got an email saying that Coinbase updated the terms of service. Um, I clicked the link to try to update the terms of service, log into Coinbase to do so. Logged into Coinbase with my password. Boom, uh, the hacker got into my account and drained, uh, all my Bitcoin. So, it wasn't a ton of, uh, you know, in USD at the time, you know, call it, uh, $50,000. But it was th- the only money that I had, and, um, lost it all from that phishing attack.
- HSHarry Stebbings
What did you do then? I, 'cause that- that, this next step is the difference between, sorry, this sounds awful, but winners and losers. Losers cry and go to their friends and say, "I was unfairly cheated." What did you do?
- NTNick Tomaino
I think I came close to, to crying, honestly. It's like, it was, it was very painful. You know, my, my wife remembers, um, I'm sure. Yeah, it, it took about 24 hours, um, and it's like, you, you, you feel like shit. Um, you know, you blame other people or, or things like that. You know, I certainly thought about like, leaving the industry. Um, but at the end of the day, it's like, my belief, um, in, in, in crypto more than anything else, it's like, you know, led me to the, the, the thinking like, "You need to use this to level up." At the end of the day, it was my, um, you know, mistake, uh, you know, they, they caught me slipping, right? So, it's like, you need to use it to, to level up and to motivate you to, to go bigger. That was kind of the lesson. And it still, I mean, this is still an issue in crypto, um, you know, obviously hacking, and we all know someone that's gotten, um, you know, phished or clicked a MetaMask link or something like that, and I still t- you know, I have friends that come to me all the time. It- it's kind of a big unknown secret, um, you know, un- unspoken secret, I should say, in, in crypto, like, how many people, uh, actually get hacked and no one really talks about it. But, um, but yeah, you basically just have to use it to, to motivate you and to level up to go bigger. So, that's, that's what I try to do.
- HSHarry Stebbings
I, I, I know that you're a sports man and you're competitive, so we can talk about that later. Um, but that is a shit day, isn't it? You know, fuck. (laughs) I don't drink any more.
- NTNick Tomaino
Yeah.
- HSHarry Stebbings
But that's a day when I would need a mojito at 9:00 AM. Um, ah. (laughs)
- NTNick Tomaino
(laughs)
- HSHarry Stebbings
Okay, I want to get to one confirmation. I mean, man, the, the scaling and the evolution is incredible. Um, I want to start on, how big is the f- And I'm gonna ask some pretty base questions, but I live in standard venture world.
- NTNick Tomaino
Yeah.
- HSHarry Stebbings
And so it's different. How big is the fund and how do you think through the right size of fund to raise?
- NTNick Tomaino
So, our first fund, uh, which was launched in 2017 is 26 million. You know, 26 million at that time, in cr- in venture for like a first time, uh, you know, fund manager, is, is big. But in crypto, is actually pretty small. And I actually could've raised much more. Um, and a lot of people in crypto is like, "Oh, why is your fund so small?" It's like, like, kind of looking down on me that, uh, you know, I had such a small fund. You know, th- that just is the time in crypto. Um, it was, it was a bull market and, um, you know, in bull markets, there's, there's a lot of FOMO. You can really capitalize on that. I thought it was important to start small and, uh, and be disciplined. Particularly because like, our focus is, um, you know, very early stage, kind of pre-seed, seed, uh, end products that we deeply understand from a user perspective. So, um, you know, the thinking was, um, $26 million fund, make, um, between 20 and 30 investments of between 500K and, uh, a million or so, in terms of, uh, initial investment. Um, so that was kind of the, the first fund and, and the thinking.
- HSHarry Stebbings
Okay, so that's the first fund. Love that. Well done for the discipline mindset. Not common in this industry. What do the second and third look like? How do we get to a billion in AUM?
- NTNick Tomaino
Well, a billion in AUM includes, um, is kind of the, the, the mark to, to market, right? It's, it's the value of the total portfolio. We've stayed, uh, fairly small in, um, our fund sizes. So, uh, fund two is 50 million. Fund three, and that was 2019 vintage, uh, fund three is 130 million, um, and that was, uh, 2021 vintage. The NFT fund, um, which is a separate kind of thing that we do, um, is, uh, about 80 million.
- HSHarry Stebbings
We're gonna talk about NFTs later. Um, I have to ask, in terms of actually, you mentioned there are 30 companies per fund, right level of diversification with that. How do loss rates in crypto investing differ to normal? Or are they very similar? How do you think about that? And downside protection as well, I guess.
- NTNick Tomaino
We've seen, in our funds, loss rates have been, um, lower so far. And again, we're, we're still 2017 vintage, we're about six years in, so you know, there's still a long way to go. But like, in our fund one, um, we have, um, I believe it's 22 investments in that fund, right. So I said about 20, between 20 and 30 in, in each fund, and that's how, that's how every fund, even fund three, which is 130 million, we're still doing early stage, uh, bleeding edge crypto. We're still doing kind of first money in. Like, we haven't changed our strategy. We do slightly bigger checks now, but it's, it's really the same strategy and that's something I think that has gone wrong in, in crypto, is like, you know, when, when you have a lot of money being thrown at you and a lot of, uh, hype and things like that, you can go in different directions and raise massive funds, start doing growth stage. You know, I get why people do it for, uh, you know, to, to make more, um, management fees and to feel more important and things like that. But we've stayed very disciplined and focused on like, what I just enjoy doing, which is like, bleeding edge crypto. So that, that's what we do.... um, I think I got a- a little off w- the question (laughs) that you asked, but...
- HSHarry Stebbings
No, no. So okay, so we see less loss rates. When you think about-
- NTNick Tomaino
Yes, the, uh, loss rates. In the first fund, 22 Investments, we've only, um, we haven't had any zeros. We've had, uh, two projects that basically, um, you know, dissolved, but they actually gave back in one case, uh, about 50% and in- in another case, about, uh, 70%. So we actually haven't had any zeros, um, in- in the portfolio, uh, at all. So that's- um, that was fund one, but then fund two, uh, fund three. I think that's pretty unique, um, and probably within crypto especially people would, uh, there's- there's all these blowups and stuff. I mean, we- we've been, I think, very disciplined and- and we do our homework. We're not investing in- in narratives, we're investing in, like, founders that we actually, uh, spend time with and want to back. And the- the vibe check's important, right? It's like, you can't just be investing in- in the narrative.
- HSHarry Stebbings
With hype cycles in crypto, did you see the transition from hardcore lovers of crypto founding companies to tourists who did crypto because it was hot? Did you feel that transition?
- NTNick Tomaino
Yeah, 100%. Every bull market you get that, right? Um, you get, there- there's people that are in it for different reasons, right? I think a- and everyone to some extent is in it for the incentives and the money, right? It's not to say that's not a big part of it, but I think there's- there's a spectrum by which you can be focused on- on money. And I think there's a healthy spectrum, um, for, you know, founders that, um, you know, want to be billionaires and make a lot of money, um, but also in doing so provide, you know, real value to the world. And then there's al- also founders that- that want to do that, um, while just extracting value to the world, right? Um, and there's a wide spectrum on that.
- HSHarry Stebbings
And so these rounds that we're investing in, are these tokens, are these equity rounds? How do they look in terms of actual structure?
- NTNick Tomaino
Both, both. That was something, you know, LPs e- early on, uh, asked a lot. And this is when I- when we raised the first fund it was in the middle of kind of the ICO boom, um, and so some people thought, "Oh, are you investing in ICOs?" We didn't invest in one ICO. Um, and some people were like, "Oh, you're not investing in ICOs? This is like the thing that's happening in crypto, how are you not investing in ICOs?" And, um, we weren't necessarily opposed to ICOs, but what we saw was the founders that were doing ICOs felt very, um, you know, short-term focused as opposed to long-term focused, right? They were doing the ICO because it was a way to raise a lot of money, but they weren't really thinking strategically about how to build a product for the long term that made sense. And the founders that we were talking to at the time that were- were thinking strategically about, uh, you know, building a product that was useful for the world that could provide real value, um, you know, they were- they were just, you know, launching, um, typical, uh, equity based businesses. We're not religious about, um, anything really. We're very practical in kind of seeing what- what is happening in the market, not on the surface level but- but in talking to- to founders and to making decisions based on that. In terms of, like, the private stuff that we- we did for fund one, it was very much equity, but we also very much believe in tokens as well. So our token deals were- were more buying, uh, you know, like we bought a significant amount of Bitcoin and ETH, uh, as well, um, i- in- in that fund.
- HSHarry Stebbings
Can I ask, when- when we look at you putting... obviously you posted on Twitter the 5.13, uh, X, uh, distributions back, which is amazing. When you look at those distributions, was that equity that converted and, you know, it was an acquisition or it was an IP or whatever that was, or it... was that largely tokens? I'm just intrigued how much of the liquidity came from equity versus tokens.
- NTNick Tomaino
Yeah, it- it was mostly, uh, equity actually. So this is another thing too, especially I... you don't spend a lot of time on crypto Twitter, Harry, but- but I do. Um, and, you know, there's a lot of hate, I would say, for crypto VCs. Um, and I understand that because a big part of the crypto VC game is doing these private, um, token deals, and then you kind of build some prestige, media narrative, uh, hype, um, and then sell
- 22:36 – 40:08
Crypto VC Strategies & Public Perception
- NTNick Tomaino
the token, um, to retail, and then retail gets sucked in and- and the VCs kind of dump tokens on retail. That's like a big game being played within crypto VC.
- HSHarry Stebbings
Is that even allowed? Like, I- I've- I've heard discussions around kind of SEC investigations before, but is that even allowed, and should that be allowed?
- NTNick Tomaino
Is it- is it legal, do you mean?
- HSHarry Stebbings
Yeah.
- NTNick Tomaino
It can be. I mean, there- there- there is nuance. Like, there- there's certain holding periods that you're- um, that you're subject to and stuff like that. So, it might not be a- as, uh, simple as that and it's not happening in every case. In some cases it's, you have to wait a year before you do that, so it's not as blatant as, like, you know, immediately listing and... but I mean, this is, by the way, this is what FTX... n- a lot of people weren't paying attention and- and Silicon Valley invested hundreds of millions of dollars into FTX. FTX was doing exactly this. No one was paying attention to it, um, apparently, and- and- and retail was getting sucked in. So FTX... so, you know, Alameda was their investment arm that was basically investing in these token projects. Then FTX, the exchange, was listing these tokens, hyping up, um, the tokens to their users, and again, I don't know if... I don't know how quickly they were dumping. This is... that's a piece of it. But again, it's like, you have private investors that are getting better deals and then these tokens are being listed on exchanges. The dumping part of it is what-... um, there's, where there's gray area on holding periods and stuff, and may or not- may not be allowed. But if you're doing this, holding for the- the appropriate time, and then dumping, that is technically legal.
- HSHarry Stebbings
I, I don't like name calling, and I think journalists often, uh, are done for it, and, uh, I just think it can be petty. But is that... And so I'm not gonna name anyone here, but is that, like, across industry or are some players worse than others?
- NTNick Tomaino
No, I think some players are worse than others, right? It's certainly not cross-industry, right? Like, there's a lot of good players in this space that aren't doing that at all. Yeah, I'm not saying it's cross-industry.
- HSHarry Stebbings
Are- a- are these materially impacted in terms of their deal flow? 'Cause what I- wh- I've heard this before, and I'm like, "Well, surely no entrepreneurs wanna take their money if they're, like, highly criticized in, you know, crypto communities. People hate them. Surely, no one wants to work with them."
- NTNick Tomaino
There are certain founders that, um, that go for the prestige, um, you know, maybe they get, uh, some hate from anons on Twitter or something. But they're still... They get, um, you know, press and they have, uh, have prestige.
- HSHarry Stebbings
Are crypto rounds collaborative? I remember talking to Avichal, uh, at Electric, and he was like, "The lovely thing about crypto is, like, there are a lot more collaborative rounds than traditional venture." Are they really? Because to me, if it's been actually raised, there's still, um, a lot at allocation and you have to compete.
- NTNick Tomaino
Um, I think it depends. I, I think it's- it feels similar to venture. I mean, there's some firms that, uh, wanna take the whole round and, um, and not collaborate. There's other firms that, um, that like to collaborate a lot. I think, um... I don't know. Uh, at the end of the day, it depends on the founder. I think some, uh, a lot of founders... Like, it- it also depends on si- on fund size. Like, one of the reasons we like to keep it at, uh, a relatively small fund size is, like, we don't need to take the whole round. And there are a lot of great angels to have on- o- on board. Um, so I think... I don't know. I wouldn't- I don't feel strongly that it's much different than a traditional venture. I think that's kind of a narrative that some people believe, but I don't know.
- HSHarry Stebbings
We mentioned that the, uh, great returns so far, six years in, 5.13X. How do you think about when's the right time to sell? It's a very difficult thing to do. How do you think about liquidity, planning, and management?
- NTNick Tomaino
I think it's prudent if you have, um, a, a big winner at the early stage, um, call it series, um, C or beyond, uh, to take money off the table if you can. You know, you can d- debate about how much, but we, we basically, uh, you know, had some big winners that we, you know, sold somewhere between, uh, 10 and 30% of the position. We invest in things that we b- believe in over a 10-year period. You know, we're not, like, selling, um, the majority of our- of our st- stake in any position after, uh, five years. But if you have a big winner, I do think it's- it's prudent to, uh, to take cash and return it to your LPs. So, that's- that's the approach that we've taken.
- HSHarry Stebbings
It's funny, you tweeted before when it comes to, kind of, performance of crypto investors, that you should actually be asked a question and benchmarked against, do you outperform Bitcoin and Ethereum? Can you just explain w- how you thought about this in the context here?
- NTNick Tomaino
Well, it's pretty simple, right? I mean, as a venture, uh, manager, you get paid, uh, two and 20. Maybe more, maybe a little more, maybe a little less. But tho- those are, um, meaningful fees. The reason that you get those fees is because, um, you can outperform, um, you know, an index. And, um, you know, every private equity firm, um, you know, uses a public market, uh, equivalent. So, if you're investing in healthcare, um, you know, you're measured against a basket of public, uh, healthcare companies, right? Or whatever the industry is. So, you know, the same needs to be true in crypto where, um, you know, an investor can just have a basket of 50% Bitcoin and 50% Eth, and hold it for, um, you know, 10 years and only pay, um, you know, a 1% or less fee of, you know, to- to buy it. Every LP should be thinking, um, you know, "If I'm giving this fund manager money, um, are they going to be, um, you know, significantly outperforming, um, that basket, you know, to justify the- the two and 20, uh, fees that- that- that I'm giving them?"
- HSHarry Stebbings
Do you think venture investors should publish their returns annually, biannually?
- NTNick Tomaino
Yeah, 100%. Um, I, I mean, I- it, to me, it's one of, like, the fakest parts of- o- of venture capital. It's like e- everyone... It feels like everyone's competing for prestige. Everyone talks about fund size or, you know, is trying to get press. These kind of vanity, um, you know, metrics that, um, that aren't really related at all to what the job really of a venture investor is, which is to deliver, you know, good returns for their LPs. You know, the reason that, uh, fund size is the metric is because, you know, the incumbents want it to be that way. The incumbents who... And they- they've got great relationships with these institutional LPs that allow them to raise these big funds. If, you know, everyone viewed p- fund performance as th- you know, the- the- the metric of success, these- the big, you know, incumbents wouldn't have the- the prestige that they have. You know, there's also the- the- the regulatory issue, which I think is, um... You know, there's ways that you can be transparent with- w- and- and also make sure that you're, um, you know, you're- you're not violating any, uh, you know, r- regulation issues. But that- there's also historically, you know, regulation has caused venture to be very, kind of, private and secretive, and not as transparent as I think...... it would be ben- beneficial.
- HSHarry Stebbings
Do you think the incumbents in venture, traditional venture, will be the incumbents in crypto venture? Obviously, we've seen your Andreessens and your Sequoias raise very large funds for crypto dedicated. But I-
- NTNick Tomaino
Mm-hmm.
- HSHarry Stebbings
... again, I've had ͠Avichal ͠on the show and many others on the show who say, "No, it's a new generation. It's an entirely new setup in terms of the talent that you need. It's a different generation of winners in crypto." Which camp do you sit in?
- NTNick Tomaino
It's a combination. I guess I don't feel super strongly. Like, I think, uh, uh, you know, A16Z is a great fund in crypto, um, and I have a lot of respect for them. I do think they probably got too big, um, but, um, they still, eh, you know, have made good investments and, um, you know, like Chris Dixon, I have- I have a ton of respect for. So, you know, they're- they're obviously-
- HSHarry Stebbings
Can I be blunt? Can I be- can I be blunt, Nick?
- NTNick Tomaino
Yeah.
- HSHarry Stebbings
They're the ones- they're the ones who are always labeled as the pump and dumpers.
- NTNick Tomaino
I h- hear you on that, um, and again, I think some of that may be more recently, um, due to fund size, they just have to invest in these token projects. I'm talking more historically. I think, uh, you know, if you look at who's a winner, um, in crypto, like Chris Dixon is undoubtedly a- a huge winner in crypto. Um, but yeah, I think more recently, fund size, um, has probably caused them to do some of the stuff that people, um, you know, accuse them for. Which- which, again, I- I don't- I don't think they're dumping. Um, they- they have to- they have to be very careful about that. But I do think they are investing in some of these token projects that, um, are getting hyped up, um, to be dumped later. The truth is always nuanced, right? Um, like there- there's... And so some of these narratives that you hear are over exaggerated in- in- in different ways. Tha- tha- that's what I'd say.
- HSHarry Stebbings
Nick, you sound like me to my other half, okay? "It's not-"
- NTNick Tomaino
Mm-hmm.
- HSHarry Stebbings
"... always black and white."
- NTNick Tomaino
Yeah.
- HSHarry Stebbings
"I didn't mean what I said about your mother." Um... (laughs)
- 40:08 – 45:52
Misconceptions & Misrepresentations
- NTNick Tomaino
it... People will realize, um, the, the, the... You know, the character of, of these people that are involved.
- HSHarry Stebbings
Before we move on to NFTs, which I'm excited to talk about 'cause I, I want to be educated by you, but is there anything that you think there's a big misconception of the public in terms of SBF they don't understand, they don't get, you constantly hear misquoted, misattributed? Is there anything that you think people should know that they don't?
- NTNick Tomaino
The strong narrative now is that, like, S- SBF is this evil, um, you know, mastermind behind this. And again, I think the, the, the truth is, is often, um, you know, far from the strong narrative. So while it is true that, that SBF is, um, you know, a, a big part of this, I think maybe what people don't realize is the, the broader fraud of perception that we've talked about, right? That's a misconception.
- HSHarry Stebbings
I, I, I totally get that, um, and, and I, I wanna be educated. You mentioned kind of fraud of perception, made me think of NFTs, um, which you can tell me I'm wrong about. By the way, I bought Chain Runners. I think I probably spent 25K on them, so, you know, that's probably worth like $25 now, which, you know, something.
- NTNick Tomaino
(laughs)
- HSHarry Stebbings
Um, my question to you is, like, why am I wrong to be negative still and why are you still positive? Like, what am I missing?
- NTNick Tomaino
Well, at the end of the day, I think NFTs are, uh, an incredible business model for creators on the internet. That's really e- what, what excites me about NFTs.
- HSHarry Stebbings
What does that look like in terms of tangible use case? A- amazing for creators on the internet, what does that look like and why is that better than the traditional mechanism?
- NTNick Tomaino
It aligns incentives between creators and their supporters, right? So, incentive alignment is kind of a, um... is a underrated aspect of what crypto can do both within cryptocurrencies but also NFTs. And so, you know, as a creator, you can, um, you know, sell NFTs to your supporters and they can have, you know, an ownership, uh, you know, interest in, in your success. The combination of those two, it's not just the business model for creators, it's the new asset, investable asset class for anyone in the world to participate in. To me, that combination is really powerful. You're looking skeptical, um-
- HSHarry Stebbings
No, I'm, I'm... I, you know what?
- NTNick Tomaino
(laughs) No, I get, I understand the skepticism, right? Because at the end of the day, like-
- HSHarry Stebbings
I'm a creator, why would that work? I can do premium features, I can do paywalls. I... For the- for those that are successful, I don't need to sell you a part of my business and a part of, like, my future earnings. You, you get access to my content and I'm thrilled to have your support, but I don't need to sell you a part of-
- NTNick Tomaino
Mm-hmm.
- HSHarry Stebbings
... my future. And then for those that do need it, most often you probably won't have a huge amount of people that want it. It's that classic problem, so I don't understand how it works.
- NTNick Tomaino
It may not solve a problem for you right now, a- and that's okay, um, but it does solve a problem for a- a lot of creators that, um, that are creating content, um, of any kind, uh, and-
- HSHarry Stebbings
But okay-
- NTNick Tomaino
... they-
- HSHarry Stebbings
... if you're Tay- if you're Taylor Swift, not batting the existing businesses, I don't think. Maybe tell me if I'm wrong. And if you're a specific writer on, I- I don't know, um, uh, knitting in England in the 18th century, I don't think it sells a specific benefit over a pay wall and a higher price for a smaller audience. So I'm just trying to understand where it's better.
- NTNick Tomaino
New technology often isn't ideal for the incumbents, right? So if you're a massive creator that is, that y- is already being served well by existing business models, then, um, NFTs might not be for you. Um, they're certainly not f- for you now. They may never be for you. But, I mean, what- what NFTs are really useful for is for these kind of new internet native creators that don't have an existing business model but maybe have some true fans. So while Taylor Swift is never gonna create music NFTs, the next Taylor Swift, who may be 13 right now, um, a- and may be having a hard time getting distribution on existing distribution channels, may sell music NFTs to 100 true fans who then may help, um, her, you know, spread the, um, you know, the- the- the awareness of the music, right? So that's, um, you know, a use case that I think i- i- i- is quite interesting that really hasn't blown up yet, right, is music NFTs and the idea of, like, giving a incentive for, um, you know, the music to grow at a very early stage. Like, 'cause music itself is very memetic, right? It's like, why does, why do most people love Taylor Swift? Because everyone else loves Taylor Swift, and she's kind of cracked this, the- the- the memetic code. Is her music good? Um, you know, some- some people-
- HSHarry Stebbings
Yes.
- NTNick Tomaino
... yes, some people, some people no.
- HSHarry Stebbings
(laughs)
- NTNick Tomaino
I like, I like, um, you know, Taylor Swift. My four and a half year old daughter certainly does. You know, a lot of why people think she's good is because other people think she's good, um, and I think that can, that- that applies to cryptocurrency too. Why does everyone think Bitcoin is valuable? Because other people think it's valuable.
- HSHarry Stebbings
Sorry, I'm going for it. It's- it's the end of the day. It's dark outside, if you could see the time. Um, but I'm like, I don't think they like it because other people like it. I think they find it because other people find it, because other people have found it, so it's distributed because it's popular. So discovery is solved because it's popular, but they don't like it because other people like it. I think
- 45:52 – 59:28
Philosophies & Personal Perspectives
- HSHarry Stebbings
they just like it, and musical taste and preference has evolved in a way where actually it's largely aligned. Humans do tend to like the same thing. It's why people love pizza, or ramen, or whatever that food source is. Do you see what I mean? They discover it because a lot like it, but the liking is different.
- NTNick Tomaino
You haven't read any Rene Girard, have you?
- HSHarry Stebbings
No.
- NTNick Tomaino
Have you heard of Rene Girard?
- HSHarry Stebbings
I have. (laughs)
- NTNick Tomaino
Okay. Um-
- HSHarry Stebbings
And I was warned that he would come up. (laughs)
- NTNick Tomaino
(laughs) Well this, I mean, this is exactly what, um, Rene Girard has, has written a lot about, um, this idea of memetic desire. A- a- and this is, I- I believe, what is unique about humans, right, is that, uh, desire is actually not based internally. It's based externally, u- on the desire of others. And so I think there's core human needs that everyone has, but outside of that, I think what we like, what we desire, what we want is fundamentally based on the desire of others. In- in- in the terms of music there, um, I think this- this explains why someone like Taylor Swift gets so po- popular. You know, some people may, um, you know, like Taylor Swift early, and then once, but- but then once she gets popular it kind of, it becomes this memetic switch that other people like her because other people like her. Um, that- that's human nature. Uh, humans are fundamentally memetic.
- HSHarry Stebbings
Okay, so if we take children and put them in a room and give them a carrot and a chocolate and they have no idea which one is more popular or which one people like more...
- NTNick Tomaino
Mm-hmm.
- HSHarry Stebbings
... they will like the carrot as much as the chocolate? No, there is a chemical composition to the chocolate which triggers chemicals in your brain that you need and want more of it. Same thing actually with music and tones and notes. There's a huge amount of research that sad music actually can make you feel comforted when you're heartbroken, which is why Lewis Capaldi has such a-
- NTNick Tomaino
Mm-hmm.
- HSHarry Stebbings
... strong career. So it's chemical. It's not-
- NTNick Tomaino
Yeah. No, I, I'm not... There- there is a ch- chemical component as well. Again, i- i- it's like the- the truth is nuanced, right? So it's not to say that there aren't, um, fundamental things, uh, that humans, um, like more than others. But most people are way more influenced by others than they would fundamentally acknowledge, I guess, I- I guess would be my point. So there are some people that fundamentally gravitate to certain things for chemical reasons, but I think there's way more re- people that gravitate towards those things because, just because other people, um, gravitate to them is what I'd say.
- HSHarry Stebbings
I mean, we- we both operate in the venture world, so I mean, I can't disagree with m- the memetic nature of human following when it comes to deals. (laughs)
- NTNick Tomaino
Mm-hmm.
- HSHarry Stebbings
... so I- I totally get you there. Can I ask, in terms of like people following what other people do, you obviously see that when you look at volumes in terms of purchases on, uh, trading platforms. Y- you're a very early investor in OpenSea. How do you think about how to be bullish on OpenSea or not, given volumes being where they are?
- NTNick Tomaino
I mean, I- I haven't talked much about what we fundamentally do, uh, uh, as a firm, which is invest in kind of authentic, first of its kind, uh, products that, you know, we- we think are pushing the space forward. Um, and authenticity is- is- is the thing that really matters, you know. Authenticity matters maybe not as much in the- um, in the short term, um, but it matters a lot in the long term because it's kind of a- a sign of, um, a- a true believer, uh, someone that's, you know, in it for more than just the- the short-term money and attention. Um, so we really love kind of these authentic projects. And, uh, you know, OpenSea was the authentic, um, you know, NFT marketplace. That's not to say that, um, you know, their success is- uh, is a given moving forward, but, you know, for- for o- for OpenSea, um, I think if NFTs, um, become the massive, uh, asset class that I think they- they will, the OpenSea as the kind of on-ramp, you know, into NFTs is- is a- is a massive business. So that's my kind of long-term, very high level thesis on OpenSea, uh, that- that really hasn't changed since we- we started. And again, we're- we're early stage investors. We're not as much making judgments about, you know, was OpenSea a great, uh, investment at 13 billion, um, like, um, you know, the last round was. You know, I- I don't know about that. But, um, do I think it's going to be a- an important product in the world, uh, in, uh, five years, much more important than it is today? Yes, because I think NFTs are important and because I think an- an on-ramp to NFTs is- um, is very valuable for people.
- HSHarry Stebbings
Did you sell OpenSea at 13? I mean, it's a high price.
- NTNick Tomaino
Yeah. Again, not- not- we- we still own the m- majority of our- our position. But- um, but yeah, we- we took some chips off the table.
- HSHarry Stebbings
Yeah. No, I- I totally agree and- and get you there. I get that. Can I ask timeline? Like it's so e- it's such a bad question, and I always listen to interviewers and I'm like, "God, these questions, what..." And then I kind of end up asking because I'm just interested. When you think about kind of that resurgence of NFTs, reinflation of trading activities on OpenSea, is that one year, three years, 10 years? I know it's a cheap question, but I'm just intrigued what broad landscape of time you think it comes back in.
- NTNick Tomaino
I would say three to five years. You know, it's likely before that, but, um, you know, with a high degree of- of conviction, I would say three to five years. I mean, NFTs aren't going away, right? Like, the- even- even the simplest form of- of- of an NFT, which is just visual artwork. Um, traditional artwork is massive and, um, there is a new wave of crypto, uh, rich people that view, uh, crypto art just like traditional rich people view traditional art. That's already happening, um, in a big way. Um, and even if that is the only thing that happens in NFTs, which I don't think it is, I think NFTs are still gonna be very big. But then you have, you know, dynamic NFTs that can change on chain based on certain variables. You have NFTs within games, you have music NFTs, you have all these other, uh, directions that NFTs could go that they haven't yet. I think that that's the lens which I- I view, um, you know, a bull case for NFTs.
- HSHarry Stebbings
Nick, I spoke to Mark Cuban before the show, always a fun conversation to have. Uh, and he waxed lyrical about you in many different ways. He- he gave me pros and cons (laughs) , uh, which was fun. But one of the pros he said was your incredible independence of thought, which kind of goes back to the memetic-ness or memetic nature of humankind and how you avoid that. Bluntly, that is a contrarian approach to NFTs today. How do you stay independent-minded when world narratives are so strong today?
- NTNick Tomaino
I don't know. I've kind of always been, uh, a contrarian, um, in some sense. Like, I think about even like in high school, I didn't really care what other people were doing or thought. Like, I did- I- a good example of this, uh, is- is drinking, right? Like, I didn't, uh, I never drank, um, in high school or- or- or college really. I think of drinking as something that's also like super memetic. And I mean, maybe for some people it makes them feel good, and this goes back to the biological versus what's- what's biological and what's- what's memetic. It's like maybe for some people drinking makes them feel good. I think for a lot of people, drinking actually makes them feel bad, but they do it anyway 'cause other people do it. This is another tangent we don't have to go in, but to- to answer your question, I've just always, um, I think thought about things a little differently and wasn't really influenced by- uh, by what people thought. I think my parents, um, just raised me very well. I never... I've- I've always felt, um, mentally strong and never felt really insecure about anything. I think insecurity can- can, uh, cause people to like fill a hole, to- to be searching for more money or more attention or things like that, and I've just kind of always stayed grounded. So, I don't know, maybe those are some reasons. But-
- HSHarry Stebbings
It's amazing to hear, and I- I, listen, adore my mother and, you know, love-... parenting and children, uh, so I- I loved it. But not to feel insecure is a very difficult thing. I think everyone is insecure in some way. Do you disagree? I'm- I'm fascinated. A- like, if you are the person who doesn't feel insecurity, that's amazing. Like, well done, Nick. (laughs)
- NTNick Tomaino
No, I'm not-
- HSHarry Stebbings
Like, we should study. (laughs)
- NTNick Tomaino
... uh, there are certainly things I feel insecure about, right? So I'm not saying I'm secure about everything in my life absolutely or something like that. But I don't know, I do think a competitive advantage that I have, especially in the crypto space, is like a mental strength or something that, um, I'm not constantly trying to get approval from anyone really. I'm just kind of living my life. And again, I- if I think about it, it's like maybe my parents, um, are a big reason for that. I don't know. I- I should... I've never really thanked them for that. By the way, if- if they're watching, uh, thank you Mom and Dad.
- HSHarry Stebbings
I mean, A, an episode that touches on the heartstrings, Nick, you are just killing this show.
- NTNick Tomaino
(laughs) There's stuff I feel insecure about for sure, um, and there's, you know, we all- all do. I don't know. I do think that's maybe an explanation for, again, my ability to not chase things, I guess.
- 59:28 – 1:16:44
Personal Insights & Quick-Fire Round
- NTNick Tomaino
where maybe I'm- I'm too, um, dogmatic, too purist, and, um, I'm constantly, you know, trying to reassess my frame and make sure that I'm- I'm not missing things because of that.
- HSHarry Stebbings
Okay, final two, but they're kind of tied together, which is like you learn a lot from wins and losses. What's your biggest win, and how did that impact your mindset? And what's your biggest loss, and how did that impact your mindset?
- NTNick Tomaino
Biggest win, I mean, we've talked about it, I think it would have to be OpenSea. That was a product that I just believed in from a user perspective more than anything. It's like I was buying and selling CryptoKitties, um, back in, um, I believe it was late 2016. Initially, on the CryptoKitties website, um, was the only place that you could trade CryptoKitties, and they charged 5%. And then OpenSea was just a product that allowed you to trade CryptoKitties for 2% rather than 5%. If this is truly an NFT, users can do what they want with it, right? And so just a marketplace to allow people to- to buy and sell these kind of off the main creator's website just made a lot of sense for me, and that was why we invested in it. And at the time, this... You know, they came out of Y Combinator, but they- it wasn't a hot deal at all. Um, like actually, you know, we- we led the round, um, and we were, uh, kind of trying to convince our LPs to invest. Um, it wasn't like... And some of them did, and- and did incredibly well, but it's like there were crypto funds at that time, um, everyone kind of looked at NFTs as kind of this stupid thing that didn't make sense, um, for the most part. That was the, that was the Silicon Valley kind of perspective and narrative. And we let kind of our user perspective kind of guide us, and that- that is I think what allowed to...... for that big win. The loss, I would say we're, I, I don't know if it was, how you framed it, loss or mistake.
- HSHarry Stebbings
Where do you mark OpenSea today? If we talk about LPs and how they think about book value. And you can say, Harry, fuck off, but like-
- NTNick Tomaino
Yeah. It's down, it's, I would say, down significantly.
- HSHarry Stebbings
Is that like one billion? Is that like five billion?
- NTNick Tomaino
You're in the right ballpark, I'd say.
- HSHarry Stebbings
Good. Okay. No, no. Won't push. Uh, I, I, I'm a Brit, so I can kind of sense when you're entering-
- NTNick Tomaino
Yeah.
- HSHarry Stebbings
... a sensitive enough zone. Okay. Biggest loss-
- NTNick Tomaino
Yeah. No. I, I, I just don't ... W- I mean, I don't wanna be sensitive. I, I, I'm, I can tell you off, um, but, um, I just wanna be careful with, uh, for, for the company and stuff like that.
- HSHarry Stebbings
I to- totally get it. In terms of the, the, the biggest loss or miss, they kinda can be either/or. What was the biggest loss or miss, and how did that impact your mindset?
- NTNick Tomaino
Interestingly, I would say it's also OpenSea, right? Because, um, when we invested, um, we only invested 500K initially. And that was, again, like at that time we had a $26 million fund. You know, our, our, our mandate was, you know, checks between 500K and a million. So it was, um, you know, w- within our mandate. But yeah. We invested, um, 500K and then we, um, brought a bunch of our LPs in to invest between 500K and a million, call it. So, um, that was one where, you know, I learned if, you know, if you, if you have kind of conviction, um, you gotta be more aggressive. Um, and-
- HSHarry Stebbings
Did you have the, did you ha- did you have the conviction then?
- NTNick Tomaino
It's harder to have conviction when you're just starting off. So, um, it takes lessons like this. Um, so yeah. I think we did have c- some conviction, but, um, part of the reason we were doing that at the time is 'cause, um, you know, we di- we didn't really fully believe, uh, as, as much as we should, in kind of, you know, our investment thesis. And we thought it would be a good thing to, you know, for relationships and stuff like that, to bring, uh, you know, deals to our LPs. Right? And so that was th- that was the thinking. You know, in some ways that, that I think a lot of first-time fund managers do that, and, um, that could be a good decision, by the way. It's like, it's good to, um, build strong relationships and, um, and to help o- o- other people get into deals and stuff like that. But at the end of the day, when it comes to, like, generating returns for LPs, um, which again, is what we're trying to do in, in, in venture, it's like, that was not the, the optimal decision, um, for that.
- HSHarry Stebbings
Did you sell across rounds on the way up? 'Cause I think this is another one that just a lot of managers don't know is like, should I sell in one chunk or cross rounds? Did you sell kinda continuously on the way up?
- NTNick Tomaino
No.
- HSHarry Stebbings
Or no.
- NTNick Tomaino
No. Yeah. I, I mean, on the way up happened quickly, and it, I mean, it was more just a feel thing than anything else. It's like we actually invested o- on the way up a little bit, um, and then, and then sold on the, the big way up.
- HSHarry Stebbings
Hoof. I, I'm sure also those LPs reinvested with you (laughs) after bringing them into the seed round of OpenSea, I'm sure they kinda said, "Yeah. Yeah. Fun too. Yeah. We'll do that. Sure."
- NTNick Tomaino
Yeah.
- HSHarry Stebbings
Totally.
- NTNick Tomaino
Yeah.
- HSHarry Stebbings
Um, listen. I wanna do a quick-fire with you. So I say a short statement, you give me your immediate thoughts. Does that sound okay?
- NTNick Tomaino
Yeah. That sounds great. Let's do it.
- HSHarry Stebbings
You can be an LP in a seed firm, a series A firm and a growth firm. Which ones?
- NTNick Tomaino
I'm just gonna use the funds that I am LPs in, um, because the only L- the funds I wanna be in is kind of like newish ones that aren't super well-known. Um, because I think-
- HSHarry Stebbings
Right.
- NTNick Tomaino
... the, the well-known where there's strong narratives. And basically, the newest ones, I'm at a point where I, I kind of can be, um, and I'm, I, I do that. The seed fund I'd say is a, a fund called, uh, Pronomos. Patri, um, is a, uh, very interesting guy that, um, was, uh, the, one of the, uh, the founders of the Seasteading Institute. He's a, uh, very, uh, I would call him a principled in some ways, a libertarian, um, who, um, his grandfather was Milton Friedman, a famous economist. And he's, uh, been, uh, very deep in kind of, uh, seasteading a- as an idea for, um, many years. Um, and seasta- uh, uh, are you familiar with seasteading?
- HSHarry Stebbings
I, I'm, I'm now looking at seasteading, but this is the first time I've seen it, so.
Episode duration: 1:16:44
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