The Ledger, every show

“A lot of the people who were very iconic in the nineties and the 2000 happened to be white male artists who are currently out of favor in the art world. And there's not a lot of demand for their work, but it's a really good buying opportunity for those artists…”

“What became obvious to me was that seed funds that claimed they had proprietary deal flow were mostly kidding themselves, they're a little delusional, and it's hard to believe that a seed firm that has two or three people have more coverage at early stage than…”

“The VCs who I believe are the most successful VCs and have had the most, you know, storied careers tend to be the people that take every single introduction I send them, and then the VCs who are still building their careers and I send them deals are like, oh, …”

“Early liquidity was the bug and not the feature of crypto. People got rich too quickly and they stopped building things.”

“If you look at all the data in the art world, it tends to work like this cycle continuously where things that were iconic 20 years ago tend to be undervalued 20 years later, then get very highly valued 30 to 40 years later.”

“We'll do a better commission split with you. You know, like, it's not fifty-fifty with us. We'll, we'll go sixty-forty. We'll go seventy-thirty. You want a signing bonus? Here's a million dollars cash up front. Like, go with us. Don't go with them. It's very c…”

“And what I'd realized over time was that if you eliminate Uber and Roblox from the equation whose seed rounds were led by first round capital, it's close to impossible to identify power law companies in which the seed round was led by a seed stage venture capi…”

“What I focused on was ownership as a relative metric as opposed to an absolute metric. And what I mean by that was, I knew I could get five percent ownership in these deals very consistently, and I knew the firms that I was co-investing alongside can get 15% o…”

“By the time we fully deployed fund one it became pretty obvious that in 94% of the companies we'd invested in, There was not a venture fund you could have invested in anywhere in the world that would have gotten you more look through ownership in that company …”

“Pretty much every multistage tier one VC firm will do a seed deal at 10% if they have to. If you push them down to six or seven, it's just not worth it. They'd rather wait for the Series A.”

“I found I've had a lot of success with dilution sensitive founders... They tend to just be a little bit more high conviction on what they're building. And they tend to believe that every percent of equity they give away is one percent of equity they'll never g…”

“It's hard for me to believe if I meet somebody That if I can't get a sense that this person is special, or has been special, or has done impressive things in their life, that the first impressive thing they're ever going to do is this company that they're aski…”

“Typically when one of those three firms extends an offer to a company, they tend to win, unless they're competing with one of the two other ones, and then they tend to only lose to one of the other two.”

“When those firms are competing for a hyper-competitive financing, it tends to be the same one, two, or three partners who tends to do most of the selling and closing for those deals to bring those deals home, and very few venture capital firms have more than o…”

“I don't think the end result is ultimately these companies are all just gonna go public.”

“If at any given time there is, you know, 50 important practicing artists in the world or even the estates of the most iconic dead artists, They tend to be represented by the big four galleries, Hauser, Gagosian, Zwirner, Pace, and once they're represented by t…”

“Michael, you know, I think he's got three Picassos, but I think he's got the three best Picassos ever. And he's got probably the best Mark Rothko I've ever seen. He's got the best Franz Klein I'd seen. Even on contemporary artists, he has the single best Laura…”

“And then it became very apparent to me that when a multi-stage fund and a seed fund tried to compete with one another, that it was very hard for a seed stage venture capital firm to compete with a multi-stage venture capital firm. Oftentimes, multi-stage ventu…”

“If you look between, like, it was either, I think, like, 2008 and 2011, there were about 1000 seed deals funded in that time frame, or at least publicly announced seed deals in that time frame, so there's some survivorship bias there, but what you need to ulti…”

“That I ended up for a brief period of time, I think for a six month window, I was one third of all the volume on, on AngelList.”

“I think the local pivot is what kills companies”

“The density of high quality board members that have storied reputations of being great board members at those three particular firms, I think, outweighs the number of high quality board members that exist at pretty much any other venture capital firm.”

“Venture is the only asset class where historical results is somewhat indicative of future performance, and you can actually somewhat forecast how a venture capital firm will do over time based on how they've done historically”

“The part of the ecosystem that seems unhealthy to me and is very reminiscent of 2021 is The timeline from graduation from seed to A to B, B to C.”

“I think the, Feedback lips and hedge funds are too tight. I think you can convince yourself you're a good investor or convince yourself you're a bad investor too quickly in, in, in hedge funds, and I think there's, which is why, I mean, if you look at hedge fu…”

“Everybody suggested that I should start a company, and I think that's terrible advice to give anybody. You should never advise anybody to start a company. I should start it on their own, or not start one at all.”

“Arguably, their future track record won't be as good as their historical track record because the deals they were able to access to those platform funds might not be deals that they have the ability to access or win in the future.”

“The companies in venture that are the largest are still outpacing the growth of any of their public company comps.”

“Once I spent enough time familiarizing myself with the market, I realized, like anything, if you're going to invest time and resources into something, you're better off doing the majority of the work yourself. Obviously it's good to have people like advisors w…”

“You have the four, five, six top venture capital firms in the world that tend to have exposure to every power law company, any generational company, any given vintage, and then more often than not, you'll see the same firms that finance those companies earlier…”

“Finding these artists early in their career that had a high, you know, So to speak, graduation rate to getting picked up by the blue chip mega galleries, and then as soon as that happened, their price is basically quadruple.”

“There's a thousand artists in any generation, and only, you know, 10 of them end up mattering 20 or 30 years later”

“George Kondo and Rashi Johnson are probably the two artists that fit the most squarely in that bucket today.”

“And that's why museum affiliation is also a really great way to access great art because galleries are more inclined to give great paintings to people who are on the boards of the MoMA and the Met and the Whitney and the Guggenheim, because they know that more…”

“If they realize you're only gonna buy what you want to buy, they'll ultimately give you what you want if you play along and play ball, but if you know, you're the guy they can give second tier and third tier work to, you will always be the guy they give second…”

“The big galleries that have great clients and are able to control their markets tend to not only manage all the primary sales, but they tend to also manage the majority of the secondary sales.”

“I think Sotheby's about, like, a three billion dollar market cap, and it's well over a hundred year old company, so I think good businesses, not phenomenal businesses because I think their margins are a lot more volatile than one would think looking into it ex…”

“I got an angel check into Rippling. I got a first dollar check into Solana, four cents a token. I got a seed check into Clay. I got a seed check into Cherry, a seed check into Newfront, a bunch of crypto companies. I got into the management company round of a …”

“I think our SPVs have returned close to a hundred million dollars on, on AngelList at this point.”

“Within the first 47 companies that I'd funded two of them, you know, Ripple and Solana, have coin market caps of north of a hundred billion dollars today. Rippling is, is approaching a twenty billion dollar market cap, and everything else I mentioned is, you k…”

“I literally had filed bankruptcy at 24 years old when my previous startup company had failed. So I was literally out of bankruptcy starting a venture capital firm”

“At one point Lightspeed invited me to be a scout for them, and, you know, I put half my scout fund into the seed round at Rippling, so that worked out well.”

“There is this weird phenomenon in Silicon Valley that every time a tier one fund or maybe two tier one funds finance a company in a category and the next three months I'll get pitched 15 companies doing the exact same thing.”

“If there's multi-stage funds around the table, the deal will get done no lower than 25, and it'll probably get done no higher than 50. If it gets done higher than 50, it means one multi-stage got really excited and just turned it straight into a series A, at w…”

“You know, it used to be I want to maintain an average entry valuation of sub twenty million. That's become impossible. I used to be able to do that, but I know I can no longer maintain an average entry valuation of sub twenty million.”

“You probably have about a dozen, maybe 15 places you can write checks that large in venture capital today.”

“Historically these galleries would represent 10, 15 artists. Now the bigger galleries are representing 75 to 80 artists. Smaller ones are representing 25 to 30 artists.”

“He you know, he was in the three million dollar post-money valuation round of Airbnb. He was the first dollar into Pinterest. He was early in Uber. He was early in PayPal.”