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Chris Sacca
Founder of Lowercase Capital, Lowercase Capital

#79: Chris Sacca on Being Different and Making Billions

📅 Jul 06, 2026 BlackNova Productions 91 MIN 1 VIEWS 163 SEGMENTS · 3 SPEAKERS
"Fuck it... I'm just not going to play this traditionally anymore." - Chris Sacca Chris Sacca was recently the cover story of the "Midas Issue" of Forbes Magazine. The reason: He is a newly-minted billionaire and the proprietor of what will likely be the most successful venture capital fund in history: LOWERCASE I of LOWERCASE Capital. He's an early-stage investor in companies like Twitter, Uber, Instagram, Kickstarter, and many more. In this interview, we discuss unfair advantages, how Chris chooses founders and investments, stories of missed opportunities, the styles that differentiate Wall...

What Chris Sacca said

Written from the verified transcript and checked against it. Every figure links to the moment it was said.

Chris Sacca, founder of Lowercase Capital, discussed his career as an angel investor and venture capitalist, noting his first fund may be the most successful in venture capital history, with a 250x multiple. He outlined his investing principles: only invest where he can impact outcomes, start with something great, give himself a chance to get rich, and be proud of every deal. He emphasized investing only in live products and avoiding founders who lack 'inevitability of success.' He admitted passing on Dropbox, Airbnb, GoPro, and Snapchat, attributing these misses to letting the negative case dominate. He contrasted VC culture with hedge funds and private equity, highlighting long-term collaboration. He recommended books like 'Not Fade Away' and 'How to Get Filthy Rich in Rising Asia' for empathy, and shared personal stories, including a notebook from age 20 predicting his career, and his strategy of moving to Truckee to play offense and buying Twitter stock to accumulate 18% before IPO.

Key takeaways

  1. First fund is at a 250x multiple, potentially the most successful in venture capital history.
  2. Passed on Dropbox, Airbnb, GoPro, and Snapchat, costing hundreds of millions.
  3. Accumulated about 18% of Twitter before its IPO by buying early investors' stock.
  4. Moved to Truckee to play offense, building relationships by inviting people to stay.

Numbers and commitments

FigureWhat it refers toTypeAt
250x Multiple on first fund metric 5:57
18% Ownership of Twitter before IPO metric 1:20:34
$600,000 Price of Truckee house price 1:17:10
$12 million Lost in a week in a leveraged bet metric 1:26:16
$4 million Additional loss after the $12 million metric 1:26:16
40 Age at which he planned to be done with his job timeline 1:09:10
3 to 4 hours Walk each way for water in Ethiopian villages metric 47:23
50 million users Instagram user milestone Kevin Systrom referenced metric 15:19
3x Return on a $50,000 investment sold to Amazon metric 11:52
$50,000 Investment that returned 3x price 11:52

Chapters

  1. 0:00Introduction and background
  2. 10:23Investing principles and rules
  3. 14:10Founder red flags and inevitability
  4. 22:05Missed deals and lessons
  5. 33:17VC vs hedge fund vs PE
  6. 39:01Empathy and book recommendations
  7. 47:23Personal journey and notebook prophecy
  8. 1:17:10Playing offense and Twitter stock
  9. 1:25:43Advice for entrepreneurs

Questions asked in this interview

12
  1. 3:27And for people who don't have much context on you, number one, is it Saka or Sacca?
  2. 4:48Could you tell people a little bit about how that has gone for you?
  3. 13:20Categorically, what would some of those be?
  4. 18:58... who I would let watch my kids or whatever it might be.' But what are the commonalities—or are there commonalities when you look across these founders for whom success and massive scale just seems predestined? What are the commonalities?
  5. 27:15... with those companies in terms of the analysis of the process that you followed, or did you make the right decision based on your rules you've set up for yourself and you just missed out on a few opportunities but also hit some home runs?
  6. 39:01What books or resources outside of personal relationships and these mentors that you've had, compliments and so on, are there any particular books or resources that have helped you become a better investor?
  7. 51:41What did your parents do that you are also trying to do with your kids?
  8. 1:04:22Was there a movie, did you watch like The Toy or what was there, Trading Places? Was there a trigger?
  9. 1:06:56What was the method to the math?
  10. 1:13:33Do you have any thoughts, kind of general suggestions that you would make to someone in that position?
  11. 1:22:14Wait, so can I just ask a luggage space question?
  12. 1:24:12Two last questions and then maybe we can revisit a bunch of this another time, but is there any purchase that you have made, could be years ago or recently, less than $100, that had a significant positive impact on your life?
Narrator 0:00 ↗
Optimal. At this altitude, I can run flat out for a half mile before my hands start shaking. Can I ask you a personal question? What is my first time? What if I'm a cybernetic organism living over metal endoskeleton?
Tim Ferriss 0:22 ↗
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Why hello thrillers, killers, and $100 billers. This is Tim Ferriss and welcome to another episode of the Tim Ferriss show. I've had a lot of whey protein. I've had a lot of supplementation, BCAAs, few other goodies like synthetic ketones, and I'm raring and roaring to go with this episode. So, I don't want to give you too long of a prelude, but if you haven't joined me before on the Tim Ferriss show, this entire program is about deconstructing excellence. It is about interviewing world-class performers, the best at what they do, to identify the rituals, routines, influences, books, tips, and tools and so on that you can use. So, borrowing best practices from the best in the world. In this episode, we have a very fun guest. He is widely requested and now he's here. Chris Saka or Chris Sacca, depending on how you say his name. He was recently on the cover of Forbes magazine, their Midas issue, and the title says, 'Venture cowboy, the 39-year-old behind Uber, Twitter, and Instagram might be the best angel ever. So, why all the bad blood and burned bridges?' And then the article, if you look inside, is titled, 'How super angel Chris Sacca made billions, burned bridges, and crafted the best seed portfolio ever.' I have known Chris for quite some time and I've mentioned before that in the game of early stage investing I've learned a ton from a lot of people, but three people stand out immediately. Mike Maples Jr. and then Chris Sacca and Naval Ravikant. Those are three who have been very, very generous with their time. And this episode is wide ranging. It's not just about investing. It is about life design. It is about career decisions and much, much more. So, please enjoy my conversation with Chris Sacca.
Chris, my fans have demanded it. People have asked far and wide for you to be on the show. So, thanks for cutting out some time in this spectacular trip.
Chris Sacca 3:22 ↗
Oh, I'm psyched you're here. We're on Necker Island in the British Virgin Islands.
Tim Ferriss 3:27 ↗
My first time to the BVI. It is paradise, not too surprisingly. And for people who don't have much context on you, number one, is it Saka or Sacca?
Chris Sacca 3:41 ↗
That's totally regional. I'm from near Buffalo, New York. So it's Siaka. It's very nasal. You got to get it right. And then Siaka. I'm Chris Siaka. Hey you guys. You guys.
Tim Ferriss 3:52 ↗
So do you introduce yourself as Saka?
Chris Sacca 3:54 ↗
I don't—let's see. What's your name? Chris, you know, I'm more focused on spelling it because everyone's like, 'What the hell?' So I'm like S-A-C-C-A, but I guess it's Saka. Chris Sacka. That comes off my tongue.
Tim Ferriss 4:05 ↗
Sacka. All right, cool. And you grew up, like you said, on the East Coast. But let's do a quick—not entire retrospective, but to give people the present tense, what are you best known for aside from that?
Chris Sacca 4:21 ↗
Professionally or personally?
Tim Ferriss 4:22 ↗
Both.
Chris Sacca 4:24 ↗
Aside from that amazing, my wife.
Tim Ferriss 4:25 ↗
All three.
Chris Sacca 4:25 ↗
So, professionally I'm known for being a venture capitalist, an angel investor turned venture capitalist, and I was one of the first investors in Twitter, one of the first investors in Uber, Instagram, Kickstarter, Docker, Optimizely, Lookout, Twilio—just going down my unicorns.
Tim Ferriss 4:48 ↗
You have this sort of unicorn radar, and you of course had the angel investing experience and then you had your fund experience. Could you tell people a little bit about how that has gone for you?
Chris Sacca 5:06 ↗
In terms of managing my funds?
Tim Ferriss 5:08 ↗
Your first—just your first fund. I would assume that is one of the reasons why you were just recently on the cover of Forbes magazine in a horrifyingly—
Chris Sacca 5:17 ↗
Gaudy shirt. We can talk about the shirt. No. So, our first fund is turning out to—it looks like it might be the most successful fund in the history of venture capital. We had Twitter in there, we had Uber in there, Instagram's in there, Docker still in there, Optimizely still in there. We had some very cool stuff like Zencoder was in there. So, we've had some good deals that have gotten bought along the way, but it's just taken off. There's no—no fund is ever done, and right now I don't think Uber's done growing and so—
Tim Ferriss 5:56 ↗
Certainly hope not.
Chris Sacca 5:57 ↗
Yeah. So we're at somewhere around 250x multiple on the fund.
Tim Ferriss 6:05 ↗
That's amazing. And I want to—I'll start off. Some people have followed our friendship over the years, the heckling, the endless heckling on Twitter. And I mean, no, it's—I'm very sincere and authentic when I ask when you and Kevin Rose are going to release the podcast episode where you guys make out.
Chris Sacca 6:24 ↗
And Kevin told me that was behind the paywall.
Tim Ferriss 6:27 ↗
It's the bonus wrestling—
Chris Sacca 6:29 ↗
Behind the paywall, and I think we have to wait until there's a slump in our careers and then keep that in your back pocket.
Tim Ferriss 6:33 ↗
We'll pull a Kardashian, reinvent ourselves. But the gratitude I want to express first before we get into things is multifold. So some people who've read The 4-Hour Body might recall that I mentioned you in that book for introducing me to Total Immersion, which was I think the first time we ever met, you brought it up. This was at the barbecue that Kra actually threw outside his apartment, and you said something along the lines of—when I described how bad I was at swimming and pretty much incapable of swimming, and you said, 'I have the answer to your prayers,' which I thought was a great response, which ended up being accurate in this case, and it was Total Immersion swimming. So I learned to swim for the first time properly in my 30s using that method. So thank you for that. And also since the early days, you've been a very open book when it came to talking to you about investing and advising. And of course the legal notepad has been now transcribed into Evernote. So, I have many Sacca files that are all very favorable. But how did you—what were some of your formative experiences growing up?
Chris Sacca 7:42 ↗
Um, well, let me just talk to what you were just saying in terms of being generous. I mean, first of all, the Total Immersion thing is like a religion. When you get it, you get it, right? And I went from dragging my ass around the pool just kicking too hard and paddling too hard to when Total Immersion hit me I could suddenly swim a couple miles and get bored. And so I was just there as an apostle, man, when you were like, 'I'm struggling with swimming.' That was—I was just geeking out. And the same way you can get going on lifting techniques and stuff like that, I'm like, you're in my world now. I'm going to talk about swimming. But the same with the investing stuff. I mean, I was really lucky when it came time for me to get started as an investor. I had many, many guys there paying it forward and teaching me about the game. Guys like Josh Koppelman at First Round, Tony Conrad at True Ventures, really being generous of their time and helping me figure out what was going on. The guys at Industry Ventures were indispensable for me, Hans and his team. And so for me when you came along and started asking questions about that, not only I feel like I was paying it forward again, but in the same way—you and I never invest in a simple idea, the execution is everything. I don't feel like I'm really giving any secret away by telling you what the approach is. You still have to go execute on it, right? So I can give you my lens on how I think about this stuff, you know, things other people have taught me, things I think I might have improved upon, etc. But I can lay that playbook on you and if you're not good at this, you can't fake it, right? And so I don't have any fear in kind of disclosing my secrets to B-Teamers because they're not going to end up competing with me. In your case, you're good at it. And so it's become an incredible side business for you in addition to everything you do with media. But there's no fear in putting that stuff out there. And the other lesson they taught me is that if I get to you and teach you some of this stuff, you're going to naturally be an ally of mine in this industry. So, if I can get in there and kind of teach you how I think about the world, how I can be helpful to companies, and you start using that same method, then we're going to end up doing deals together. And you and I have, and we've made a fair amount of money doing that. So I didn't want to leave that unanswered.
Tim Ferriss 9:57 ↗
Well, it's really been fun to watch you sort of evolve and grow and experiment also in investing. And just coming back, we can rewind the clock back to your upbringing a little bit later on, but just since we're on the topic, what were some of the pieces of advice that you were given by say the guys that you mentioned or other people early on that helped you to approach early stage investing in a more intelligent way?
Chris Sacca 10:23 ↗
Yeah, I mean a couple of guys have said things that I've now taken and made my own and have codified. So I have rules for investing now that were definitely influenced by a lot of these guys giving me advice and things that I've now put to work. So one is only get involved in deals where I know I can personally impact the outcome. Now, there's no guarantee that I can take it from X to sold or X to IPO, but I need to know that I can have a material impact to make something more likely to succeed. So, the second rule I've developed, and this is again influenced by guys along the way who've given me advice, is start with something that's already great that you can make more awesome, but don't start with something shitty that you think you can make good. And that's hard—like when you work in a company, and a lot of your listeners I know work in big companies, you have to work on the shit that somebody hands you, right? So you're just dealt the 27 and you're like, 'Well, okay, that's what the boss gave me, I got to play this hand out.' When you get into investing, your default stance should be no, because most deals suck, most deals won't make money, most companies will fail. And the temptation always is you see your first deal and you're like, 'Okay, I know I can be helpful to these guys, I know I can make this shitty thing better.' And so your first few deals are always the worst.
Tim Ferriss 11:44 ↗
That's how I lost—yeah, 50 grand on my first deal. And I was just like, 'Oh, it's like 25% of what I had hypothetically allocated after 2 years.' I was just like, 'Oh my god.'
Chris Sacca 11:52 ↗
No, it's because you get in that room and you're like, 'Okay, I know how I can make this thing better, right?' And you forget that you need to start from something that's already independently pretty damn good and then make it better. So, our third principle is give yourself a chance to get rich. And that was something that was influenced more by a lot of these fund investors who are like, 'Hey, it's all well and good to throw 25K around into some of these deals.' But most of them won't be home runs. Most of them won't turn into unicorns. Most of them are going to require a ton of work. A bunch of those will fail, but a bunch of them will be successful to the tune of doubling that money, but over years and years of work. And so I've sold companies—I sold a company into Amazon where I saw 3x on a $50,000 investment in a fund. By the time my fund got paid back and I got my part back and I had been busting my ass in that company for a couple years, I barely had money left to buy the guy's dinner to celebrate the deal. And so that's another thing—is leaving ourselves enough room to benefit from scale, going in at prices that are low enough that if the company is as successful as we think it's going to be, we've given ourselves a chance to get rich. And then the fourth thing that I think we evolved internally or that I evolved was just be proud of every deal. There's stuff that I've passed on that I just don't regret it at all. It seemed like maybe a good way to make money, but I don't have to explain to my kids that's how I made money. And so those are kind of the guiding principles that I think have been shaped.
Tim Ferriss 13:20 ↗
Categorically, what would some of those be?
Chris Sacca 13:22 ↗
I'll, you know, mistype domains, right? So that's a great way to make money. People are stupid and they mistype stuff all the time. And you can put ads on sites that don't really look like ads. Subscription businesses that make it impossible for you to cancel your subscription ever. You can sign up online, but you need to send them a postcard to cancel—like that kind of stuff. I see that stuff. You know, people making unsubstantiated claims about the effectiveness of their stuff. This anonymous content stuff that just was going in bad places. So I just want to be really proud of our deals. And so those I think are some principles that have been shaped by a lot of these guys giving me advice along the way.
Tim Ferriss 14:10 ↗
What are—when you meet with founders for the first time, is there anything that disqualifies them quickly? Are there certain red flags that you look for?
Chris Sacca 14:22 ↗
Yeah. So, this has evolved over time. You know, I've now been doing this for a while and have done, you know, over a hundred deals and have seen a bunch of those work out and I've seen a bunch of them not work out. And I read all the posts that my peers in the industry write, other VCs. Everyone's constantly stabbing at, 'Hey, what is the rule? Like, how do you get into one of these meetings?' So let me first have a couple parameters. One is I almost only invest in things that are already live in production. Just no hypotheticals, no ideas. I think there might be one exception to that and it was a particularly gifted entrepreneur that I already worked with before, but other than that, we look for stuff that is already actually being—that has users, that can demonstrate that the team is capable of building and launching stuff together and getting it out there in the market.
But that said, the one thing that will turn me off right now is if I see that in the pitch the founder is trying to convince themselves. If I can pick up on any hint that they don't in their marrow believe in this story, then it's no dice. As I look at all the most successful founders I've backed, the thing they have is inevitability of success. There are no conditional statements coming out of their mouths. There's no like, 'Well, if it works, it would be rad.' Instead, it's just always—you talk to Kevin Systrom at Instagram when he was working on it himself. He was literally a sole guy working on the product and he's like, 'So, when we get to 50 million users, we'll roll out this other stuff.' And you're just like, 'Wait, what?' He's just peering into the future, kind of looking through you into something in the future, and you're just like, 'I gotta get along for the ride with this guy.' The same thing when you talk to Evan Williams, when it comes to talking about the likelihood of success of his products, he just knows. He just knew Twitter would be a big thing. He knows Medium will be a big thing. He doesn't need to convince you of that right now. He just knows. You talk to Patrick and John Collison at Stripe and of course they're building for this thing to be a big dominant company and it just will be. You spent time with Travis. You're an investor in Uber. Was there any doubt at any time that Uber would dominate the planet? There's no doubt. There's no doubt.
Tim Ferriss 16:54 ↗
Can you just share—there's an anecdote I think we probably talked about over drinks at some point, but the—
Chris Sacca 17:01 ↗
Wii Tennis, Wii Tennis, Wii Tennis.
Tim Ferriss 17:05 ↗
Yeah. Can you tell the story?
Chris Sacca 17:07 ↗
So, it's a few years ago. We're up at my house and we live up in the mountains in Truckee, and it was over the holidays, so my parents were there. I think it was actually New Year's Day, so Travis and I had been—we have a tradition up there on New Year's Eve. We go snowshoeing at midnight and drink champagne out in the meadow and stuff. So, I think it was a pretty rough morning. But Travis is sitting on the couch and my dad senses some weakness and he challenges him to a game of Wii Tennis. So on the Nintendo Wii, my dad's not a bad player. He's pretty good. So Travis is like, 'Okay, Mr. Sacca.' And he picks up the controller and they play the first couple of games and they're tight games, but Travis wins them. And my dad is there taking full swings with the paddle, breaking a little sweat, and Travis is still blurry from the night before, barely breaking his wrist, and he's beating my dad. In my head I was like, 'What the hell is this?' And then there was that Inigo Montoya moment, Princess Bride style, where Travis turns to my dad and says, 'I'm sorry, but I'm not left-handed'—or I forget if it's left or right—but he switches hands with the controller. And the next three games, my dad never touches the ball. There were no points scored on any of Travis's serves. And I was like, 'What the hell is going on? What is this?' And after the torture got to be too much, Travis just says, 'Well, let me take you to the global leaderboard. I'm sorry, I didn't mean to be holding out.' And he goes to the global leaderboard and Travis Kalanick was ranked number two in the world at Wii Tennis in his spare time. Now Uber was already a thing then—literally he was already building a startup—but he's just so obsessive, so competitive. And that's the thing—as we look across the portfolio at all the most kick-ass companies, that's something they just have right up front—is that they're not hoping and praying for success. They know it's going to happen.
Tim Ferriss 18:58 ↗
Now, on that note though, so to pull out two names, for instance, you have an Evan Williams—blogger, Twitter, Medium, etc. Then you have Travis. Personality-wise, at least from the outside looking in, very different personality types. And I bump into some investors who say, 'Well, I only invest in merciless, sort of highly offensive—offensive meaning not defensive—CEOs.' Because then other people are like, 'No, I only invest in people who I would let watch my kids or whatever it might be.' But what are the commonalities—or are there commonalities when you look across these founders for whom success and massive scale just seems predestined? What are the commonalities?
Chris Sacca 19:42 ↗
Well, I think something—so we'll take Ev and Travis as examples, but across our most successful founders—let's use Matt Mullenweg, WordPress. That's a billion dollar company now. Billion plus. These guys are all incredible, incredible listeners. So when they do open their mouths, it can be bombastic and offensive and aggressive and in your face, but they're all incredible listeners. And I don't just mean in casual conversation. I mean, these guys go out of their way to interview other people. They really—if you catch Ev, he's got a notebook always. And if you ask him to see the last few pages of the notebook, he's just meeting with other people—billionaires and leaders whose jobs might not overlap with his at all, but from whom he's learning. Voracious reader. Part of why Medium started was he was really back deep into long form content when he took a break from Twitter. And so that guy is just constantly learning, studying, studying. And so when he speaks, it matters. But he's listening more than he speaks.
Tim Ferriss 20:58 ↗
He's terrific. And he also—it's—I mean he listens to anyone that he's sitting down with. It doesn't matter if it's the waitress or a primary school teacher. We've done a lot of traveling together. He was on the podcast also. Very good listener.
Chris Sacca 21:13 ↗
Yeah. And so, and again, you just look across the board, these guys are learning, they're modeling, they're constantly researching, they're gathering data. You know, Travis would think it a competitive disadvantage for you to know exactly what's going on in his head sometimes. So, he'll listen. And it's an amazing talent. And I think that is a commonality across those people.
Tim Ferriss 21:34 ↗
With the investing game that you've obviously been a participant in for quite a while now, you have to say no a lot. And I took a close look at poker in the last year with the TV show and there were a couple of quotes that came up quite a bit along the lines of, 'I made my money sitting, not playing hands.' But that having been said, what are some of the deals—the whales that got away?
Chris Sacca 22:05 ↗
Yeah. So, first of all, I mean, this is a rigged game, right? And I'm just looking to make it even more rigged. So, for those who don't know, venture capital—I mean, it's totally unfair. People give me their money, I draw a management fee off it. So, they pay me to take their money and invest it for them. If I make money, then I pay them back the management fee. And then after that, we split the profits and I get a really big chunk of the profits. And if I lose money, that's fine. It doesn't come out of my pocket. I keep my fee and my investors lose money. That's how this industry works. That's bananas, right? And at some point it's going to break because—
Tim Ferriss 22:46 ↗
You've also incepted me with the term bananas, which I've started using compulsively. Mazio also has done the same thing, who works with Chris.
Chris Sacca 22:53 ↗
Yeah. It's just an unforgivably unfair rigged game that's in favor of the venture capitalist. And so the reality is the risk of an investor doesn't begin to compare to the risk of a founder. And so that's one thing that kind of drives me crazy sometimes about some investors. And I love the entrepreneurial spirit that goes into building a firm. I mean, I built my firm from scratch and there's certainly founder-type lessons in there, but your cash flow positive from day one when you start a venture fund. And your downside is incredibly limited by the structure of the fund. So, that said, what it allows me to do is place some bets on some stuff that I'd like to think success is inevitable, those things, but I can look at the risk analysis and say, 'Okay, this is a binary outcome, a one or a zero.' And some of those things just don't get there. You know, one of my constant recurring nightmares is about the stuff I passed on.
Tim Ferriss 23:57 ↗
No, that's—Yeah, exactly. That's what I was trying to ask.
Chris Sacca 24:00 ↗
You know, I've done some deals where I thought it was going to be a lot bigger and it ends up going away. But, so the Dropbox guys, I met those guys very early on while they're still in Y Combinator. I got an early look, had an opportunity to do the deal and I pulled those guys aside and I was like, 'Hey, look at Google, we were using a version of this called Platypus, which became G Drive, and they're going to crush you guys, man. So, you should probably find some other product to pivot to.' That probably cost me hundreds of millions of dollars.
Tim Ferriss 24:34 ↗
Did they give you a pat on the head and walk away?
Chris Sacca 24:34 ↗
Yeah. No, I mean, when I see Drew, the CEO of Dropbox, I bring it up before he can. That's—this is myself. Yeah, I just get it out there right away. The Airbnb guys at Y Com, same thing.
Tim Ferriss 24:48 ↗
Incredible business.
Chris Sacca 24:49 ↗
An amazing business and one to be proud of, too. I mean, I'm really jealous. I'm not in that business, not just for the money, but I love what they do. I really admire them a lot and their culture, but at the time they were allowing you to rent out a room in somebody's house while the owner was still there. And that just seemed really scary to me. And I pulled the guys aside and I was just like, 'Guys, you know, somebody's going to get raped or murdered in one of these houses and the blood is going to be on your hands.' I literally said that out loud to them.
Tim Ferriss 25:19 ↗
What's that worth? Like 15 or 20 billion now?
Chris Sacca 25:21 ↗
Now, in fairness, you're probably not wrong, right? I mean, at a certain scale—
Tim Ferriss 25:24 ↗
At scale, it has to happen. Something's gonna happen.
Chris Sacca 25:26 ↗
Yeah. I mean, I like to say sometimes—like when you think about scale, like someone who works at Walmart murdered someone last night, right? There's just no doubt about it at that scale with a few million employees, one of them murdered somebody last night.
Tim Ferriss 25:39 ↗
You have to look at it like Edward Norton in Fight Club, like an actuarial analysis for insurance. Which is terrifying, but that's the reality of big numbers. But—
Chris Sacca 25:50 ↗
But there's—I'll tell you, so there's one other famous one. There's a bunch of these, but actually, I'll give you two. Nick—because I wasn't reminded of this until recently. Nick Woodman from GoPro came to Google. Now, I wasn't an investor at the time, but I did a lot of Google's investments and partnerships. And so, Eric Schmidt, CEO of Google, said, 'Hey, will you come in here and sit with this pitch? He's a friend of a friend. We got to meet this guy.' So, Woodman comes in with GoPro. And Eric's like, 'I don't know.' And I was like, 'We'd be foolish to do this deal. How's this guy from Santa Cruz going to compete with all these Asians building hardware? You can't hold a candle to the Taiwanese and the Koreans.' I was like, 'No dice, man. Let this guy go.' And I think I introduced him to somebody over at YouTube just as a consolation. I saw that dude this winter skiing. He's worth like three or four billion dollars now. And he didn't forget that meeting. So, and then the Snapchat guys, I gave a talk in LA and they came up to me. I never met them before. They came up after the talk and said, 'We're big fans. We'd really like to work with you.' And I was like, 'Yeah, sure. I mean, I know you guys are up to something cool. I admire it.' I took like eight weeks to set up the meeting and by then the Benchmark guys had done that deal.
Tim Ferriss 27:02 ↗
That's again—oh my god, I can't imagine how much money we've left on the table as a result of that.
Chris Sacca 27:09 ↗
So, you know, I like to say when I'm wrong, I'm wrong. And when I'm right, I'm really, really right.
Tim Ferriss 27:15 ↗
And the question on being wrong, though, I'm very curious about this. And just coming back to kind of the poker analysis or analogy rather—and I actually heard about this in depth when I first became friends with some hedge fund managers and they really try to focus on good process and not conflating bad outcomes with bad process. In other words, did I make the right decision at the time? Even if I missed out on a huge opportunity, because you can also pick a company for the wrong reasons and have a fantastic outcome, but over time if you develop bad habits, it can really screw you. So, do you think that you made the wrong decision with those companies in terms of the analysis of the process that you followed, or did you make the right decision based on your rules you've set up for yourself and you just missed out on a few opportunities but also hit some home runs?
Chris Sacca 28:09 ↗
The one thing that all those failures to invest have in common is that I let the negative case dominate my analysis of whether I should invest or not. So, in the beginning—as a seed stage investor, you don't really get a lot of data, right? We don't have any financials to look at, the team usually consists of three to five people, there's some users but not enough at scale, they're usually just the early adopters, so you don't know whether it's going to be a big thing yet, so you don't have a massive diligence process. And so a lot of what you're going on is your gut about this product and about this team. And I think the easiest way to screw this up is to let the negative case dominate your perspective. So, Dropbox, I'm thinking about the competitive landscape and I'm thinking, 'Okay, Google's going to crush them.' Well, first of all, we've seen that didn't actually happen. And rarely does the incumbent crush anybody. It's just not that common. A startup is going to move much faster than a division of a company where it's not their bread and butter. I mean, G Drive spent three years in beta, internal beta, etc. It was never really a priority for them. So, of course, Dropbox is going to win that. I look at Airbnb. Yes, there's going to be bad things that happen. Like, people get their apartments trashed from time to time, but somehow I let that distract me from the potential for this worldwide marketplace for space that was just going to displace hotels. With Snapchat, I'm thinking about dick pics and how it's being used—
Tim Ferriss 29:44 ↗
That was on the pro side.
Chris Sacca 29:45 ↗
Yeah, exactly. I'm like, hey. But no, I'm thinking about like it's lame content. It's being used poorly by junior high girls and stuff like that who are exposing themselves and it just—there were bad examples of how Snapchat wasn't necessarily a helpful thing. And again, I like to be proud of my deals. On the other hand, you see today it is just—it's a network with hundreds of millions of users who are building incredibly valuable content, with the launch of Stories and Discover and stuff like that. But I got distracted. I let the downside and negative case outweigh the risk. And yet, you look at Uber. Uber could have—it was easy enough to say no to Uber because, oh, the taxis or the regulation or the lobby or these drivers are going to hurt people at some point. And somehow I was able to look past all that when nobody else in the Valley wanted to and get that deal done.
Yeah, what I think is really interesting about Uber in particular is, and for those people that don't know, I was early adviser to Uber, so I'm biased obviously in a lot of ways when I talk about it, but I think you actually got there before me.
Tim Ferriss 30:53 ↗
Yeah, I was pre-money adviser because I'd been an adviser at StumbleUpon. I had worked with Garrett and I'm now working again collaborating with him on Expa, which is super fun. But in the beginning, the way that Uber got dismissed, and I think this is a really common mistake it seems that a lot of investors make, is people said, 'Oh my god, really like black cars for 1-percenters in San Francisco? What's the market for that?' And they viewed a very niche activity as by definition constrained to say 1-percenters in San Francisco, New York. And if you look at let's say even recycling it started out that way, and they kind of confused the first target with the total market, and they also looked at just the available market which they misdefined very early on. And in the case of like an Airbnb or an Uber, they can grow the market beyond any comparable that's available. So in any case, but a lot of these start off so incredibly niche that people misread the market potential, I think. But let me ask you a question about focusing on the positive scenarios and the potential high multiple outcomes, because for those people who aren't familiar with venture capital, it's a term that comes up a lot in magazines and media coverage. It's very hot right now. So you explained it in brief, but it's fair to say that two and 20 is a pretty fair way to think about it in terms of, I mean not everybody, but that's like how people talk about venture capital and hedge funds and so on. You have this management fee and then you have the carry which is kind of your split. But what I wonder is, do you think VCs should not think about the downside as much as the upside because they're only rewarded on the upside and not on the downside. Whereas say hedge fund investors can have long short bets and think more about when I hang out with like hedge fund guys versus say venture capitalists or VCs, the hedge fund guys are many of them much more kind of apocalyptic in their thinking. And it would seem like that is tied to their ability to make money from a lot of those catastrophes.
Chris Sacca 33:06 ↗
Yeah, those guys can be short. In fact, even if the apocalypse isn't really approaching, they'll still get people to write articles about the impending apocalypse for those companies to make sure that it's a self-fulfilling prophecy.
Tim Ferriss 33:17 ↗
Yeah. What are the biggest differences in your mind between the top venture capitalists, hedge fund guys, and private equity guys, or how do they differ if they do, or what do they have in common?
Chris Sacca 33:31 ↗
Well, as we were talking about at lunch, first of all, everyone I know on Wall Street is just jacked on stimulants all day long. So, they're taking Provigil, they're doing rails, those guys are just in such an incredibly competitive environment that they're using every chemical edge they can find. That's definitely not happening in the VC set. The VC life demands kind of a much more steady, reflective state. There's certainly obviously moments of negotiation and standoffs, but it's much more of a thought and emotional intelligence exercise. You know, that said, because Silicon Valley is so kind of built on positive energy and loveydovey, what ends up happening is as the stakes have gotten higher, the funds have gotten bigger, the industry's more flush with capital, it's more competitive than ever. And a friend of mine who I've done some work with who's on the East Coast in the private equity world says the main difference between New York and San Francisco is out here in New York we stab each other in the eye face to face, and out there you guys just cut the other guy's Achilles and let him bleed out while looking at them. You know, it's incredible how I think in the San Francisco world, we really try and maintain these long-term friendships. We try and build these reputations that will scale over time because as a venture capitalist, you're raising money every 3 years basically, and it's a 10-year fund. And you're hoping to have a long tenure in the industry with great relationships that you can draw on to recruit people in your portfolio companies that you can use to help your portfolio companies raise more money, go public, or get sold. And because of the fact that we're big equity holders who only get paid back upon an ultimate exit maybe 8 to 10 years from now, we tend to act more with that in mind, that long-term perspective.
And so that's the biggest thing. You know, there are other businesses like this, like the media business is a cash quarterly business. You go to a media company, you go to a record label or movie studio and say, 'Let's do an equity deal.' And they laugh in your face and they're like, 'How much revenue are you going to guarantee in year one?' Because that's how they get paid, right? All those executives are on annual contracts and they've got payments they still owe on their houses in the Hamptons and they're just like, 'I'm not going to walk away from that guaranteed cash right now.'
Tim Ferriss 36:26 ↗
Sorry, I'm breaking because you're laughing right there. I know it's taking you.
Chris Sacca 36:30 ↗
No, no, no. This is good. I wonder if that could also be related to the fact that in Silicon Valley, it's such a small world and you work very hard to get to a point where you have deal flow, meaning opportunities that come to you that are of a sort of pre-filtered high quality, right? Whereas in a lot of these other spaces they're going out and using analysts to sort of hunt for opportunities that other people have not exploited. So, it's humans responding to incentives in a way. Well, in a hedge fund environment you're working with public stocks usually at arms length. You might try and go activist and go on the board. You might try to, like I alluded to, change the press cycle. But for the most part you're doing analysis at arms length of these companies. In the private equity world, there's a business already, right? There are products or multiple products, there's financials, there's supply chain, and so you're going in and saying I can do a better job of this than you can, and so there's an arms length and there's some tension obviously with management, usually sometimes you're co-opting members of that management team to go get it done. But the venture world is different in that it's much earlier and it's much more where the venture capitalist is a collaborator in determining the product and the strategy and the vector the business is going to take. And so there has to be a much more collaborative approach over the long term to go ahead and actually build this company. So, you know, I think there are certainly venture capitalists who maybe come out of the world of finance or have a different perspective that their job is just to sit on the outside and tell somebody how to run a business. That's the private equity model. But as a real early stage venture capitalist, your job is to sit in the room and actually work at the beck and call of the CEO to get stuff done to help build this company, lend advice about product strategy, about go-to-market, about the design of the front page, how to staff up and bring in the next couple of members of the team, how to go about raising money, how to deal with your first PR cycles. And so that I think brings a much different person in the successful niche, not necessarily the biggest self-promoter, not necessarily the most widely known person, etc., but somebody who actually can hustle to go ahead and, as we know, go back to what we talked earlier, to tip the balance from something that's good to being totally awesome.
Tim Ferriss 39:01 ↗
be great. What books or resources outside of personal relationships and these mentors that you've had, compliments and so on, are there any particular books or resources that have helped you become a better investor?
Chris Sacca 39:16 ↗
Yeah, I think most of those though are not business books per se. That's right. Because so I didn't get a business degree. I didn't do an MBA. I took a couple classes. It was enough to show me it was a total farce. I did get a law degree, which is an even bigger farce, but that's for another episode. So, I never had formal business training and so I don't really, and I tried to look at a few of those like instant MBA books and stuff like that. I even bought some books on venture capital and they're just so goofy. And by the way, part of that is because now we have so many great venture capitalist bloggers who are just an open book about the industry who teach it. So Brad Feld comes to mind first. A longtime friend and mentor, Brad at Feld Thoughts, has done series over the years where he breaks down each aspect of a term sheet, how to understand it and the deal documents, and this is what we think is important and these are things we think could go away. Josh Kopelman and his team have done a lot of work on that. We've now seen Y Combinator and the guys at Fenwick and West building templated documents that are really really watered down and pro-entrepreneur and just kind of have taken out a lot of the legacy stuff that didn't need to be in those documents. And so there's a lot of this learning that can happen now without having to buy books and without having to go to school. And so that's been fantastic. But where I worry about the valley and about investors as well as our entrepreneurs is in the development of everything off the ball a little bit. So, you know, you and I, I just turned 40 this week. That's why you're here.
Tim Ferriss 40:54 ↗
Happy birthday again.
Chris Sacca 40:55 ↗
But, as a 40-year-old, the people my age who were computer science majors in college, that was a major just like any other major. They still had to go get a summer job. They mowed lawns, waited tables. They had time in their curriculum to go study abroad, to volunteer. They had these really well-rounded lives. And so working with people my age and older at Google who are computer scientists was great because they had not just these amazing math and science skills, but a diversity of experience that informed great product decisions as well as just collegiality. What ended up happening was computer science degrees got so popular and so valuable that those kids didn't have to pay for school much anymore, and their only work experience was like TAing a class, not actually getting their ass kicked digging ditches or anything. And the curriculum was rigorous enough that these guys didn't get to go study abroad. And there was no opportunity to go do volunteer work and live in the developing world at all. And so as a result, I actually found we were starting to have a generation of not just entitled, you know, people talk about the entitlement of the millennials when it comes to workout things and stuff, but they weren't just entitled, but they just had such narrow band perspectives on the world. They were missing empathy. So they weren't able to put themselves in the shoes of the folks they might be building a product for, what the problems of a world might be. And so I am constantly looking for opportunities for myself and for the founders we work with to broaden the scope that they have on the world such that they can build something on a more informed basis, an emotionally informed basis. So, I really think empathy isn't, it's a word that's been kind of reduced to signal like oh somebody hurt their foot and I feel bad for them. Instead, I think much more poignantly empathy is about can I see the world through that person's lens. Can I figure out what matters to them? What are they afraid of? What's bothering them? What do they think is limiting them right now? What's their hope? And if I can do that, then it's a lot easier for me to build something for them and to sell it to them and to help them and to build a longer-term partnership with that person.
Tim Ferriss 43:14 ↗
If you were giving an assignment to folks for books or experiences, just kind of a short list for people who want to develop that type of empathy, what would you put on the list?
Chris Sacca 43:28 ↗
One of my favorite books that we give to most founders is Not Fade Away. I think it's like belly flop pic on the cover. Yeah, belly flop pic. A short life well-lived story of Peter Barton. So first of all, just on a personal note, that guy's trajectory kind of followed mine. He was a ski bum who suddenly made it big in tech. He was on the board of Yahoo. He worked at Liberty Media. And then he hits his 40s and says, 'Okay, I've accomplished what I want to accomplish. I'm dialing it back. I just want to spend time with my family.' And at that point, and this isn't a spoiler, it's literally how the book starts, he finds out he has incurable stomach cancer. And so the book walks you through his biography as well as the remaining time in his life. You will cry reading this book. It is inevitable. If you don't, I'm very worried about you, but you'll definitely cry. It'll be cathartic. But it's the kind of thing where it's an exercise in, okay, what's on the mind of the person who's dying, and how is he thinking about the impact of his death on his family, on his friends, on his business partners, on his legacy, on the continuing responsibilities as a dad even in the absence of, you know, even though he's passed on in the next life. And it's an entire exercise in perspectives. And I think that book will, you know, not only leave you feeling incredibly lucky for what we've got here and where we are, but at the same time will sharpen that sense of how do I put myself in somebody else's shoes. A similar book that I love, it's I'm going to get the title wrong. I think it's How to Get Filthy Rich in Rising Asia.
Tim Ferriss 45:15 ↗
I remember you told me about this.
Chris Sacca 45:16 ↗
This book is amazing. So, it's written in the second person, which I don't know of another book like that, but it's just you, you, you, like you wake up in this room almost like an old role player or something like that online, like Dungeons and Dragons reading. You are in a room. There's a sarcophagus, open sarcophagus. No, but it says, you know, you wake up and you basically start the book in a slum in Pakistan and it's just writing you about how you go through your day and the things that matter to you, and it turns out you're kind of entrepreneurial and you're willing to take some risks, and so you start working into other stations in life. And I don't want to give anything else about the book away, but you close that book and you feel like you've walked through 15 to 20 different lives in another world. And I just think more of that would be better for all of us. I think it'd be better for our industry, for the depth and the impact of the products we build. I think it'd just be a lot better for getting along with each other. So, you and I have traveled to Ethiopia together doing work with
Charity Water. It's hard to complain about a day's work back here in the United States when you have been in a village where they walk three to four hours each way to get water, where the kids are dying because they drink the same water that the cow poops into, where the women don't get an opportunity to go to school because they're carrying the water and on the way they might get eaten by a lion or raped. And it's really hard to find yourself complaining about our privileged US life. And that's something you could just tell working at a big company like Google, there were the people who would complain and like really really this is a hard day. Microsoft launch a competitive product and that's our horrible day. And I just think we'd all be much better off if we were able to find opportunities for our CS students to go study abroad, for our MBAs to actually spend some time around poor people, and to start building these more diverse perspectives.

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Sacca, C. (2026, July 6). #79: Chris Sacca on Being Different and Making Billions [Interview transcript]. BlackNova Productions. CEOInterviews.AI. https://ceointerviews.ai/interview/1228009/

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Chris Sacca. "#79: Chris Sacca on Being Different and Making Billions." BlackNova Productions, 6 Jul. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/1228009/.

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@misc{sacca2026_1228009,
  author       = {Chris Sacca},
  title        = {#79: Chris Sacca on Being Different and Making Billions},
  howpublished = {Interview transcript, BlackNova Productions. CEOInterviews.AI},
  year         = {2026},
  month        = {jul},
  url          = {https://ceointerviews.ai/interview/1228009/},
  note         = {Speaker-attributed transcript with timestamps}
}