The Ledger, every show

“We don't really invest in carbon accounting software or anything anymore. And we realized, A, we're not that great at it. There are a lot of other people out there in the world who are better at SaaS than we are. And B, a lot of VCs came out of being locked up…”

“It is so absolutely delicious. It beats everything but Blue Bottle now in taste tests. Stumptown, Pete's, it knocks them all out. All the hipster coffee. Blue Bottle's the only one at Cancer Mount, but it's made using no coffee.”

“I think female entrepreneurs right now have a higher bar because of cultural norms and discrimination against women.”

“Bless the activists and everybody else who cares about it. But I actually think the market is the most powerful solution to the stuff we're doing. And I think for the very first time in my life, I can have a massive impact on the planet while also making a ton…”

“I don't hang out with other VCs. I feel like they cloud my thinking.”

“So the one mistake that I think has cost me billions of dollars is focusing on the negative case for an investment and not the positive likelihood.”

“But that check I wrote was literally a credit card check for me. I didn't have any cash on hand. I was at Google, and I was vesting, but I hadn't sold any stock yet, and so I literally I went into that one with 50,000 dollars of credit card checks.”

“So I very famously took my student loan checks for law school, told the school they hadn't shown up, cash them, and use them to day trade in the market. And so this is one of the reasons why I get so nervous about what I see in the Robin Hood phenomenon. You k…”

“It was a lack of optimism that cost me some money in the beginning when I met the Airbnb guys and I pulled them aside and was like, look, somebody's going to get raped or murdered and the blood is going to be on your hands.”

“I've watched Bill Gurley knuckle up in board meetings and call bullshit, because that's the place it needs to get done, and if you don't build that rigor and discipline early on, you're not setting yourself up to be a world-class company”

“At the height of lowercase, we were managing six billion dollars, and we were three people.”

“Look, the people who succeed in this business, and this is not an endorsement, this is an observation, are not normal. Like they don't have incredible balance. And so they may like make good time for family and good time for health and working out and may put …”

“Guilt and shame aren't going to change behavior at scale. The only thing that's really going to get us there is offering people something that's better, cheaper, faster, cooler, sexier, easier to use, easier to maintain.”

“We in climate, we specifically make sure every deal has more than a gigaton carbon removal potential.”

“The discipline is around not just doing every deal that comes your way, but then doing the deals where you personally can de-risk something. Maybe it's moving it from 49 to 51% likelihood, but, you know, maybe you can't add 20% likelihood to the success, but i…”

“It turns out right now that our LP portfolio of diverse managers is running about a two and a half X.”

“For HBCUs, we would do no fee, no carry.”

“When things are going up, you tend to think it's correlated with your genius and talent, and when things are going down, you tend to think it's unlucky. You learn over time to invert that curve. When things are going up, it's lucky, and when things are going d…”

“It was a lack of optimism that cost me some money in the beginning when I met the Airbnb guys in And I pulled them aside and was like, look, somebody's going to get raped or murdered, and the blood is going to be on your hands.”

“I think we're six people now managing, you know, between the outside money and inside money over a billion dollars. At the height of lowercase, we were managing six billion dollars and we were three people.”

“That's one of the reasons I quit for a while. Was I worried that, you know, the stage of life I was in, I wasn't going to be able to fucking bring it. I wasn't going to be able to as obsessive as you need to be to succeed in this business and this industry and…”

“The people who succeed in this business, and this is not an endorsement, this is an observation, are not normal. They don't have incredible balance. And so they may like make good time for family and good time for health and working out and may put vacations o…”

“Shark Tank's real. Like, just so you know that none of that is scripted. It's the most authentic show on television. They don't tell us what to say or, and we invest our own money. We don't know anything about those companies before they walk in the door.”

“Fast forward a couple years, and not on the billions of dollars of investment it normally takes to develop an aircraft, but on the single digit millions of dollars in this case, and I think we just did a round in the tens of millions, and up until that round, …”

“These are the biggest total addressable markets in the history of the fucking world, because it turns out, like, the total addressable market is everyone who eats, and everyone who wants to move their bodies somewhere around the planet, and everyone who wants …”

“In climate, we specifically make sure every deal has more than a gigaton carbon removal potential.”

“Instagram came to me. Kevin Systrom literally said, I want three angels, you, Adam D'Angelo, and Jack Dorsey.”

“And so it turns out right now, our LP portfolio of diverse managers is running about a two and a half X.”

“And I took my student loans and I turned them into twelve million dollars. But that twelve million dollars I didn't send. I just kept rolling it back in and held material positions in these two stocks. And then within a 10 day period, I say it's black swan, bu…”

“I wrote a check into Twitter while I was still at Google for 25 K. And that was one of the things I needed that money back. So I would show up at the company and work my ass off to try and make it more valuable because that wasn't break off 25 to be polite sit…”

“The first few deals I did with my own individual money once I got out as an investor were garbage because they would come pitch me and I'm like, oh, I know how I can make this better because that's what I was used to doing at Google was just making things bett…”

“Every time a founder is considering taking money from a venture capitalist, there is the same process they should use when they're considering hiring an employee to whom they're going to give stock options. Every single time you're making the calculus is the a…”

“There is no doubt sharing space with people and breaking bread reveals a lot about who they are. What drives them? And you can't really back somebody until you know their ambition and what's on their personal scorecard.”

“We have a company that In the year, maybe three of the company was doing a hundred and twenty million dollar run rate selling a commodity, but because they make it with enzymes instead of oil and gas, they have 60% margins.”

“The one all hands meeting we have is everyone in the company is invited to our investment committee. The lead on the deal or the co-leads on the deal present the deal, but everyone in the company has access to everything we've done. All the diligence, the deal…”

“I also have this rule. If you get invited on a podcast, accept it, go on the pod. And as long as you say something that is true and authentic to yourself and accurately represents the values of our company, then you will not get in trouble for saying what you …”

“In the beginning, I made a bunch of money and I bought houses for Family and multiple houses for ourselves, and then my wife and I turn around and we're like, fuck, we're property managers. Our inbox is like, hey, this broke, and this is happening, and what do…”

“The very first one I did on my own was a company called Photobucket, which we ultimately sold for three hundred thirty million dollars, which sounded like all the money in the world at the time.”

“My second investment was Twitter, and that one was funny because Evan Williams was, I'd already been working with the company and helping him out, but Evan went and circled up investors for the round, and he's like, hey, I've got you down for 25 K, 25 K, good,…”

“When things are, without that kind of quote unquote training that came by way of tragedy, when things are going up, you tend to think it's correlated with your genius and talent. And when things are going down, you tend to think it's unlucky. And you learn ove…”

“Shark Tank's real. Like, just so you know that none of that is scripted. It's the most authentic show on television. They don't tell us what to say or, and we invest our own money. We don't know anything about those companies before they walk in the door.”

“We were in an early Uber board meeting once, and we needed a CFO. And I kind of, I, They said, okay, we need a CFO. And I stopped and I think, okay, like who could be a CFO? And I'm thinking of like old Google people who were like director of finance and maybe…”

“Instagram came to me, but like Kevin Systrom literally said, I want three angels, you, Adam D'Angelo and Jack Dorsey. And so he pitched me. I literally was not seeking photos. I, it sounds fucking hilarious, but I thought it was spent. I thought it was done. A…”

“So far, we have four other firms who are going to follow us along and start giving more access, whether it's donated interests or it's or no fee, no carry.”

“That check I wrote was literally a credit card check for me. I didn't have any cash on hand. I was at Google, and I was vesting, but I hadn't sold any stock yet. I went into that one with 50,000 dollars of credit card checks.”

“Google taught me that when they would share confidential information, they would share the board deck with the entire company on Fridays. Literally, they'd gather the entire company and show them the same slides they had shown the board on Wednesday. And that …”

“We've got basically a billion dollars at work In the field right now”

“And so far we have four other firms who are going to follow us along and start giving more access, whether it's donated interests or it's, or no fee, no carry exposure to HBCUs to start participating in this ecosystem more meaningfully.”