Chris Sacca

“I would say it would be lowercase Chris Saka's fund. I put, you know, a little check in there and got four million out like, 25,000 turned into four million, so it was a legendary fund. I think it was like ten million and returned like 1.5000000000 or somethin…”

“That's how he did his Uber investment. He did the same thing with the founder of Instagram. That's how he did his Instagram investment too, was he invited Kevin Systrom to come stay at his place in Truckee.”

“I saw Silicon Valley as the place that was most based on merit and least on seniority. Being in DC, you get exposed to politics, and politics is so much about have you earned your keep? Have you put in the time? Have you served? Have you risen up through the r…”

“When things are going up, it's easy to convince yourself you're a genius. And when things go down, it's easy to tell yourself that it was bad luck. And so much of what we do for a living is inverting that. And when things are going up, giving yourself, hey, yo…”

“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…”

“This is a company that had turned down a nine hundred and fifty million dollar acquisition offer because it wasn't a billion dollars. And eight months later, I was raising at a thirty million pre for that company.”

“At Google, I personally did the photo bucket investment using credit card checks.”

“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…”

“Crystal, my wife and I, and we're business partners and we have an informal fund of funds. We're LPs and more than a hundred things.”

“If they couldn't empathize with the host, how can I be helpful? Then it just shows somebody who is not equipped to build a startup because a startup is constantly about empathizing with your customer and your user, and then showing how can I make it easier for…”

“When you spoke with them, even as the company was in its earliest days, they spoke with the voice of the inevitability of the growth and success of the company. And they weren't selling you. It wasn't that their heart rate rose, and they were trying to convinc…”

“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.”

“When I retired lowercase, it was probably the most bankable I was. We walked away. Crystal and I retired it in 2016 to just say, This doesn't feel as compelling anymore for us personally. We don't love the impact we're having.”

“This is not concessionary capital. Crystal and I are the biggest investors in our fund. We are in this to make a lot of money.”

“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.”

“So anytime we remove carbon from a process, it just gets cheaper. Carbon has an inherent value. It's necessary for a lot of the stuff we do, And it has a monetary value. And so any way we could take it out of building a product or running a service, we just ha…”

“I told the Dropbox guys that Google was going to crush them because we already had G Drive internally. I told the Airbnb guys that somebody was going to get raped or murdered and the blood was going to be on their hands when they were renting out a room in som…”

“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 …”

“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.”

“I don't manage for IRR. I manage for multiples. So we don't run a line of credit, for instance. That would be a much better way to eke out another point of IRR, but that's not how I want to run the business.”

“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.”

“I don't know why I'd hire a financial analyst again. It's a job I value, but at the same time, this thing in moments spit back compound annual growth rate analysis.”

“Reputation is the number one currency as an investor that you have control over. The other one obviously is your track record, but you and I both know that To a certain extent that's out of the investor's control. You know, we can hopefully select great founde…”

“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…”

“So when it became clear, we are going to make some money. We just sat down with a bunch of people who had been through that process. And by the way, not just the successful people. We intentionally sat down with people whose marriages had completely dissolved,…”

“And our organization will only hire people who have had shitty jobs, who've had service jobs, who've worked extremely hard for some point in their life, and who appreciate the worst day of being a VC doesn't begin to compare to the worst day.”

“In the end, what pushed Travis out was when his team held him accountable. It was when the, you know, his 13 senior managers all wrote a letter and said, dude, you gotta stay out of the company. You know, that's really the only force that Silicon Valley leader…”

“That is the number one hardest resource in all of tech is if you can't recruit and retain good talent, you're powerless. But when your employees won't stick around, that's the only thing that keeps you honest.”

“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.”

“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.”

“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,…”

“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…”

“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…”

“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.”

“We're probably some of the most progressive people in technology, and certainly we help elect candidates who are going to raise our taxes.”

“What happens is we have this monoculture of these kids who, in computer science programs now, they've never had a job. Like, the toughest job they've ever had was being a teaching assistant for a class, and so they've never mowed lawns, waited tables, worked i…”

“We in our organization will only hire people Who have had shitty jobs, who've had service jobs, who've worked extremely hard for some point in their life, and who appreciate that the worst day of being a VC doesn't begin to compare to the worst day of working …”

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

“So by the way, I mean, our comp plan probably runs six to 10 times what the industry standard is because I want everyone to materially, I want this to be a life-changing event.”

“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.”

“Absolutely. I'll get way richer from this. I mean, we have, I have multiple companies in the portfolio right now that have the very like they have a trajectory to being multi-trillion dollar market cap.”

“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.”

“Crystal and I are LPs in dozens and dozens of funds, Because that was one of the ways we paid it forward, you know, and to help kind of promote diversity in the industry, we backed literally dozens of first-time general partners who are women, people of color,…”

“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…”

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

“Yeah, I think Facebook is a cancer, and they know it.”

“And I've been in the room with Zuckerberg. I've watched him fucking lie to the president of the United States about what they know internally versus, like, the claims he spouts out loud.”

“But I think SoftBank is just value destructive, and it drives me fucking crazy.”

“The multiples are already there. I think IRR is 95% right now, and so so we're already getting fucking rich doing it”

“And if we don't do it, You know, North Korea is going to do it on their own. Like, some rogue state is going to launch a projectile that explodes a bunch of dust in the atmosphere, and we won't know which dust, which altitude, and the best ways to do it, and w…”

“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. You know, Flickr had sold for like 25 to thirty five million doll…”

“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.”

“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…”

“We had two other investments, Triller and DubSmash, that were kind of the same thing, right? And there's no real reason that they didn't succeed. They just didn't.”

“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.”

“When Evan Williams saw that he was going to make some money, he went out and started interviewing rich people and asking them for tips.”