CEOInterviews.AIChris Sacca, Lowercase Capital

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Interviewer0:08

I want to talk about your early career and how you got to this point first, because I think you kind of came out of nowhere for a lot of people. So first of all, let's start with just how you got to Silicon Valley.

C

Chris Sacca0:20

I drove. No, well, okay. So I grew up in a small town near Buffalo, New York. As a kid, I had a proclivity for math. Starting in sixth grade, I went to the University of Buffalo for math. So I was like a normal student during the day and a math nerd at night. I loved math, and it got to where it wasn't just arithmetic, it got theoretical and it was mind-blowing and fun, but it was also getting in the way of me being a normal kid. For my last couple years of high school, I still played sports and stuff, but while my friends were drinking beer in a farmer's field on a Wednesday night, I was doing math. I finally just had almost like a math breakdown. I was like, 'Enough. I'm out.' And I went back to being normal. When I applied to school, I found the one school in the country that doesn't have any math or science requirement: the School of Foreign Service at Georgetown.

I

Interviewer1:27

So you just took a break from math. You wanted a math strike.

C

Chris Sacca1:30

Yeah, that's a good way of putting it. I was out. I was just checking out. So I went to school, Foreign Service at Georgetown, was studying to be a spy or a diplomat.

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Interviewer1:41

You're not very covert.

C

Chris Sacca1:42

No. Also, the number one reason I didn't become a spy or diplomat is that you can't pay back your student loans on what spies and diplomats make.

I

Interviewer1:50

Do they make that little?

C

Chris Sacca1:51

So you'd have to sell some secrets to some Russians or something. Or default on your loans. It's one or the other. But I went to school there. I studied abroad a lot in South America and all over Europe. And it was while I was living in Spain that Netscape went public. I just remember this feeling of FOMO. I don't think that was a word back then, but I just felt like, 'Holy shit, there's this whole thing going on out there, and I could be there and I'm not there.' Yet at the same time, I was also intimidated because I didn't have computer science skills. The last and only language I ever programmed was BASIC on an Apple II Plus that I got in like 19... That is the last programming language I programmed. So I felt like I was missing out, but also that I could do something there.

I

Interviewer2:46

So when you say what caught your attention was them going public, a lot of people will say what caught their attention was seeing Mosaic for the first time, seeing the web. Was it the money?

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Chris Sacca2:57

No. I went to college from 1993 to 1997 on the East Coast. The only reason I got an email address is because I didn't have enough money to call my parents from Europe. I grew up in a traditional middle-class family, so I got an email address and they got a CompuServe account so I could wait in line at a university. I went to a university in Spain that has 160,000 students and there was one computer lab, so you'd wait two hours to use the computer to email by Pine. That was the only reason I got email. We didn't have cell phones in college. I'm 37, not 50. If you didn't know where the party was when you left the dorm that night, you weren't going to find it. No one was texting you, and you weren't checking Foursquare to see where everyone was. You were out of luck. So back to the library.

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Interviewer3:44

I'm 37 as well. You should be directing this to the 18-year-olds so they get it. Remember back then, if you left the dorm not knowing where the party was, you weren't going to find it. I remember going to the six bars and being like, 'Is anyone at this one?'

C

Chris Sacca4:10

Yeah. But I didn't grow up surrounded by an intense amount of technology, and frankly in Buffalo, nobody was writing software. There wasn't an entrepreneurial culture at all. Most entrepreneurs are surrounded by entrepreneurs at some point, and that's where the spark hits. There are guys like Evan Williams who grew up in the middle of Nebraska and knew they wanted to do something, but that something usually happens when they go somewhere else and start hanging around other people who've done it before. So I came back from Europe and I wanted to go into technology, but I didn't know how. Georgetown had interviewing to go be an investment banker. And all I figured out about investment bankers is that they were douchebags. I hadn't quite... I didn't know any growing up, but the ones I'd met were, so I was like, this is probably not what I want to do.

I

Interviewer5:19

You do now have money from Goldman Sachs.

C

Chris Sacca5:22

Oh, I have no money from Goldman Sachs.

I

Interviewer5:23

I thought you had money from Goldman Sachs.

C

Chris Sacca5:25

No, you should fact-check that. Maybe from other investment banks, but not Goldman Sachs.

I

Interviewer5:33

All right. But bankers who you just called douchebags. We'll get back to that.

C

Chris Sacca5:38

There's a lot of self-awareness among bankers, to be clear. They know they're douchebags.

I

Interviewer5:46

I'm not sure most bankers would be offended by that.

C

Chris Sacca5:50

Do you know bankers? They tend to have that thing of, 'Oh yeah, the other guys are douchebags,' and they all think that. Most lawyers too. Everyone knows one nice lawyer and the rest are not.

So I couldn't find a job to interview for, and I didn't have any money and didn't know any venture capitalists. So I applied to law school, which is the default for someone who did well in school and has no idea what they want to do. But what I did was I took the student loans — they just send you a check instead of wiring it directly — and I cashed the checks and used them to start a company. I told the school the checks had never shown up. I got away with that for a little while. I started a company. I was a horrible founder. I had a lot of hubris. I thought I didn't need help, and when I did, I didn't know where to look for it. I was in Washington DC, which wasn't a cool place to start a company back then. It was absurd, and I was lucky I didn't blow all the money.

I

Interviewer7:06

What was the company doing?

C

Chris Sacca7:07

I was trying to do two things. One was data mining — this is 1997-98 — so I was trying to data mine predictively who would buy something online. Given a data set, who would be the best leads to possibly buy something on Amazon. It never went anywhere. The other thing was called CashAction. It was like those class action lawsuits you get coupons about. I wanted to aggregate all that in one place so you could find out what you were entitled to: money off a Maytag washer, five bucks from Sprint, that kind of stuff. Because the back end of that model is that if you're a lawyer and you bring plaintiffs to those cases, you get paid. The most expensive search term on Google is mesothelioma. Mesothelioma is a kind of cancer you only get if you've been exposed to asbestos. If you have that, you're eligible for the asbestos settlement trust fund, which is billions of dollars. If a lawyer brings you to that settlement fund, they get like 35 grand. So there's this weird backscratching win on both sides. I was trying to aggregate all that. I was awful. It didn't work out very well. I had some money left, but it was less than I owed the school.

So I did the prudent thing and opened a bunch of day trading accounts and started placing really... This was like January 2000. No, this was '98. I started throwing money at stocks, hanging out on Yahoo message boards to find savvy investments. I made metric tons of money. I was invested in the highest performing stock in the NASDAQ from '99 to 2000, a company called FirstCom that was a Latin American steel company. I bought into it at pennies and we ultimately sold it to AT&T at $36 a share to become AT&T Latin America. Here's what happens when things go really well.

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Interviewer9:27

How much money did you make?

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Chris Sacca9:29

I turned what was left of my student loans into $12 million.

I

Interviewer9:36

Jesus.

C

Chris Sacca9:37

That's not spy money. I took some liberties along the way, though. There's a rule in trading called Reg T. It says if you've got $1,000 in your stock account, you can buy $2,000 worth of stock on margin, but you have to maintain a 50% margin requirement. Hedge funds aren't subject to this, just individual investors. The problem was that in the early days of online trading, the platforms hadn't built that in yet. So if you had $1,000 in your account, you could buy a million dollars worth of stock. Your phone would ring and it would be a customer service rep at E*Trade or DJ Direct saying, 'Our records indicate you owe us $999,000,' and they'd give you seven days to pay. So during those seven days, you owned a million worth of stock. If it went up 20%, at the end of the week you'd sell, pay them their $999,000, and keep the profit. Then go bigger tomorrow. This method works really well in a bull market, and that's how I got to that scale.

I

Interviewer11:02

Were you doing this all the time, the day trader sitting in his underwear eating Cheetos and Red Bull, buying and selling shares minute by minute?

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Chris Sacca11:12

Mostly accurate, yeah. In fact, here's what happens when shit goes right. This is a temptation across our entire life. When everything's going up to the right, you're convinced it's because you're smart and you made good decisions. That line only gets firmer when your buddies around you echo that back. Friends of mine who were bartenders and limo drivers, I was getting them into the stock too, and they're like, 'Dude, you're a genius. I just bought a boat.' And it's all going this way. The natural human temptation is that when it's going right, it's because you're a genius. When it goes wrong, it's because you're unlucky. It takes three or four times getting your ass kicked before you realize it's actually the inverse. Sure enough, a couple years into this I'm paper rich. Luckily I didn't spend the money on anything.

I

Interviewer12:17

Did you ever attend classes?

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Chris Sacca12:19

No. Law school — the unique feature is you only have to go to the exams. There were a couple exams where I got the highest grade in the class.

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Interviewer12:31

Is that because you were lucky?

C

Chris Sacca12:33

No, it's because they're disjointed. What goes on in the exam has nothing to do with the circle jerking in the class. It's just this intellectual contortion that has nothing to do with the exam. On a couple exams, I wrote the best exam and the professor called and said, 'I can't seem to find you on my seating chart.' I said, 'Oh, I was in the back near Mike.' It was a pleasure having you in class. You can actually correspond to law school and not have to be there. In fact, the key is if you're not going to be there, you can't go the first day and have them know who you are. You have to never go.

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Interviewer13:19

So if anyone's watching and they're taking from this, I can become a millionaire if I'm in law school and only take the tests. If they've already gone to a class, they've screwed up.

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Chris Sacca13:26

Yeah. Let's be clear: I'm a horrible lawyer. So I probably should have been going to those classes. Anyway, when we last left our protagonist, he was making a ton of money.

I

Interviewer13:38

Yes. Well, he's the protagonist for now. We'll see. He probably does evil things pretty soon. He's surrounded by all his childhood buddies telling him he's a genius. Everything's up to the right. He may or may not be wearing pants.

C

Chris Sacca13:50

Probably not. Cheeto dust everywhere.

I moved to Park City, Utah during this time, though I was ostensibly really...

I

Interviewer14:04

Did that just happen?

C

Chris Sacca14:05

Yes. He wasn't there yesterday. He might have won a prize. I moved to Park City, Utah. Some buddies started a record store that I got involved in. Law school was in Washington DC, but I was living in Utah. It seemed appropriate. I was ski bumming, helping run this record store, and trading. As a quick aside, record stores at that time, this is '98, Napster started. In the early days, Napster was just enough to sample an album, but downloading the whole thing was a pain. So it was amazing for us because you'd get exposed to all this new music and then come to us to buy it. Everyone says it was a shitty time to be in music, but it was the opposite. Napster was the greatest thing ever for our record store. But if you live in a ski town, there are three main currencies for getting shit done: US dollars, film canisters full of weed, and CDs. We ended up being like a bank and a financial clearinghouse for town. I'd go into a restaurant and a guy would say, 'Do you want to pay the bill?' I'd say, 'Come to the store tomorrow.' So a guy would come and ask, 'What was that meal worth?' I'd say, 'Probably four CDs.' And if you owed Paul four CDs, you could transfer that debt and Paul could move it around. It was transactional. We kept books on who owed who money in CDs and weed. It wasn't that far removed from what I do today. I'm just kidding.

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Interviewer16:00

Is there actually a currency? Were so many CDs worth so many dollars? It couldn't have been just the value of CDs to dollars, because then what's the advantage of paying in CDs? And how did weed figure in?

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Chris Sacca16:14

Have you ever been in a barter economy? Barter economies don't pay a lot of tax. Markups are very fungible. Ski towns operate on barter. I live in a ski town now; people trade. The culture of our record store was such that we would sell you Britney Spears, but you had to sign a public declaration posted at the cash register, like a sex offender registry, where you had to put your name and address and declare to the community that you actually bought that shitty album. There was a full range of prices around CDs. It was a market, true market economics. The point is, I'm living in a ski town, surrounded by trustafarians buying string cheese and albums and guitar strings from us. I realized my entire portfolio consisted of one stock and I was highly levered. One of my buddies said, 'Dude, you got to diversify.' I said, 'You're right.' So I bought another stock.

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Interviewer17:33

What was the stock?

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Chris Sacca17:34

That stock was FirstCom. So I bought another stock called Myriad Genetics. It was a Park City-based company doing what companies like 23andMe do now, but just for individual specific genes: BRCA1 and 2, the breast cancer genes, colon cancer, and prostate cancer genes. You could take a test to see if you had an indicator or likelihood of having these cancers. Totally something I could get behind. Totally something I believe in. Insurance companies were paying for it. Amazing model. Really psyched. So I've got these two stocks and I'm all in and then some. Within a short period in the spring of 2000, two things happened. AT&T took AT&T Latin America and bankrupted it, wrote it down to zero. In a matter of days, that stock went from $40 a share to pretty much zero. When that happens, those guys who you bought all that money from are like, 'Hey, fuck you. We're going to sell it all.' In a matter of hours, I went from $12 million to about $2 million of net worth. I was freaked out, but that money was kind of virtual. I never spent it, so it never meant anything. I didn't grow up with any money, so nobody had taught me how much that really was. I had $2 million left and I'm hanging out with these guys. I asked, 'What do I do?' They said, 'Take a couple days, go skiing, relax, get your head straight.'

I

Interviewer19:20

These do sound like good wealth advisors.

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Chris Sacca19:21

Yeah. I said, 'You're so right.' So I walked away from my terminal, went skiing, and actually went to Austria for a bit. While I was there, on the back end of a joint address by Bill Clinton and Tony Blair — two guys I like and respect — for some reason that I still haven't fully processed and talk to my therapist about intermittently, at the end of that talk they said, 'By the way, we've decided that any private company holding intellectual property rights over human genomic material is just wrong, and we're going to do everything in our legislative power to undermine those patents.' So if you're a big investor in a company whose entire lifeblood is patents over breast cancer, colon cancer, and prostate cancer gene tests, you're going to see the stock go from $250 a share to $40 a share in a matter of minutes in the middle of the trading day. When the smoke cleared, I owed $4 million in my own name. I was 25 years old. I didn't have a house to sell or anything. I was just poor. Really, really poor.

I

Interviewer20:35

So what was your reaction when you realized that?

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Chris Sacca20:39

I swear I think losing $20,000 might be harder than owing $4 million, because you have an expectation you'll pay that. There's something so absurd about owing that much money. Who here in this room thinks they're going to make $4 million in a lifetime? I was not among that group.

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Interviewer21:02

It's a room of entrepreneurs, so I'd hope many of them.

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Chris Sacca21:05

$4 million is crazy money. And yet you blew three times that.

I

Interviewer21:12

Thanks for pointing that out.

Did you ever think of profit taking? Did that ever occur to you?

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Chris Sacca21:23

No. If you're winning, why would you take profits? If everyone around you is telling you you're a genius, you think you're a stock picker. CNBC was saying that at the same time. I should have known that when every sports bar in town turned ESPN off and turned on CNBC, we were probably in a bubble. When things are going right, it's very easy to look back and do a little regression analysis and correlate: 'Oh, I'm in a Latin American steel company. By coincidence, I speak Spanish. Those must be related. Oh, it's a competitive local exchange carrier with fiber optics. I used to dig trenches to install fiber optic cable. That must be related.' You put these data points together and think, 'This is my fucking destiny. I'm brilliant.' Everyone around you is saying, 'Dude, you're the man. I'm going to Club Med because of you.' You think you have the golden touch. You convince your parents and everyone to cash out their IRAs and plow it into the stock.

I

Interviewer22:35

Did your families lose money because of your advice?

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Chris Sacca22:38

Yeah. Oh my God.

I

Interviewer22:41

That seems like it would be worse than owing $4 million yourself.

C

Chris Sacca22:44

100% worse. Owing $4 million compared to the tens of thousands that people around me lost. Some of my less educated buddies, who you wouldn't consider elites, were so much smarter than I was. They bought their boats, paid off their student loans, and walked away. I was the greedy fuck who didn't. So I'm 25, I owe $4 million. I was a legitimate bankruptcy risk, but I someday wanted to be an officer of a public company, so I declared that bankruptcy wasn't an option.

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Interviewer23:29

You declared you would not declare bankruptcy.

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Chris Sacca23:31

That's a good point. Double declaration squared. So I went back to the guys I owed the money to and said, 'Look, I'm up the creek. I don't have the resources to pay you. If I BK, you get nothing. Why don't we work something out?' So I worked it down to $2.125 million and went on a payment plan. Imagine a mortgage for the most expensive house you'll never own. Interest rates were like 7%. It was nasty. But I graduated, got my law degree, took the bar, and came out to Silicon Valley to sell my soul because I needed to pay back $2.125 million in a hurry. That's how I ended up in Silicon Valley.

I

Interviewer24:23

It's quite an answer. I've asked that question a lot over 15 years covering entrepreneurs. That's the first time I've gotten that answer.

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Chris Sacca24:31

Yeah. So to sum up, I took liberties with a few financial securities laws.

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Interviewer24:35

Did you pay all the money back?

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Chris Sacca24:39

Yeah, ultimately I paid it all back.

I

Interviewer24:43

How long did it take?

C

Chris Sacca24:44

Spring of 2000 I blew up, and it was 2005 when I finally paid off my last dollar of student loans. They were the last thing I paid back because you can defer them. I accidentally overpaid Sallie Mae by something like $28, and they sent me a refund check. I never cashed it because I like the fact that Sallie Mae owes me money. It's still on the fridge at our house. I just really like the comfort of knowing that I got back out. It took a long time. I got a job as a lawyer during the day, and at night I was moonlighting doing legal work off Craigslist, writing terms and conditions for porn sites and stuff.

I

Interviewer25:46

Did they pay you in porn?

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Chris Sacca25:48

No, they paid me in cold hard cash. It's a cash business. Not weed or CDs. The funny thing about adult sites is they all thought that having strong terms and conditions would get them out of trouble for everything else they did. I'm one of the only guys who's ever kept all his clothes on and yet made money in the adult industry. But no, they were among my clients. Do you remember Elance? I think I was the first lawyer on Elance. I would do any contracts people put there. It turned out the adult website community went there early. They were early adopters of everything. I did any work I could. I did voiceover work.

I

Interviewer26:33

You don't see it like it's not happening right now. Give us a sample. Do like a car ad.

C

Chris Sacca26:40

This is really fucked up to admit. There was an African-American gentleman who had written an autobiography and he needed a voiceover for it.

I

Interviewer26:54

Go on.

C

Chris Sacca26:56

My brother, who's an actor and a YouTube star, and I figured out how to modulate our voices to sound low and appropriate. I don't think they ever published this audiobook, but we got paid.

I

Interviewer27:18

You're not going to say who it was.

C

Chris Sacca27:20

No fucking way.

I

Interviewer27:20

It was not like Nelson Mandela, was it?

C

Chris Sacca27:22

No, it was a baseball player, an early baseball player who I hold in high regard. I needed the money. Basically, I did what I could for money. Last time somebody asked me this, I said I did anything I could for money, and that became fodder for the chat room. But I did what I could to try to pay off this debt and keep it together.

I

Interviewer27:45

Was this a secret? Did people know? Were you very open about this or was it something you were kind of...

C

Chris Sacca27:51

Why would you ever tell anyone? You feel like a total loser, right? It's failure. One thing you start to learn about Silicon Valley is it is a place where you can wear failure on your arm. But most people who say that say it after they've succeeded once. It's the luxury of winning. You can then go back and sit in front of a crowd and talk about what a douche you were back then. I broke these rules, took liberties, lied to people, lost my ass, but I've made it since. So let me tell you my story.

I

Interviewer28:31

Every Panda Monthly.

C

Chris Sacca28:32

Yeah, it's harrowing. To lose everything and more, and lose money for your friends and family, that's not something you brag about.

I

Interviewer28:41

What kept you going during that time?

C

Chris Sacca28:43

I didn't have a choice. I think that's kind of it. I was working as a lawyer at Fenwick and West. It was a great job, but I was really bad at it. I'm not a detail person, and that's all a lawyer's job is — look at every square inch of the document and identify all the ways you could get nut punched. What I do for a living is be like, 'Yeah, but wouldn't it be awesome if?' Every investor and entrepreneur is like, 'Yeah, but wouldn't it be cool if?' So I was a horrible lawyer. About 13 months into that job, I got laid off. It was a great business decision on their part, but it didn't feel good at the time. It was four days before September 11th. I recently found the termination letter in my garage. It was awesome rereading it. But it wasn't... I put those events together. It was a week and four days before September 11th. I realized it because they still paid me for that week. On Thursday, I went into the firm and said, 'Look, I never got to use the firm condo in Hawaii. I busted my ass here for 13 months. Never been to Hawaii. It sounds awesome. I have something I can offer you. Reporters are going to be calling asking about the massive layoffs. I will be the laid-off person who talks to the newspaper and says you guys totally took care of us. You're awesome people. It hurt you more than it hurt us. But I want the firm condo.' A couple days later, I was in Hawaii.

I

Interviewer30:50

I love that you're telling me a story about how you profited off manipulating the press. I'm now rethinking every word that's come out of your mouth.

C

Chris Sacca30:56

No, they did do right by us. Fenwick did take care of us. They did send me to Hawaii. I had a lot of loyalty to them. They were genuinely benevolent. They didn't have to lay us off, but they did. For that week, I had job prospects. People were interviewing me and saying good things. Then September 11th happened, and my entire world, the entire economy, all of Silicon Valley imploded. Everyone who was thinking about hiring me was like, 'Good luck, kid.' I didn't have any cash in the bank. I didn't have a network. I came from Buffalo. I didn't go to Stanford or Cal. I didn't have any homies in the area. I didn't have anything to fall back on. Moving back to Buffalo was a sad story, so I didn't consider it an option. I did a couple of things. I relentlessly applied for jobs. 784 resumes went out with no answer. I kept doing freelancing stuff on Elance and Craigslist. But also, I started going out to generate my own business. I would go to networking events — the Churchill Club, the Chinese Software Professionals Association, the Indus Entrepreneurs — all the guys from India, Pakistan, Bangladesh. They were an awesome group of people and they had no problem with a honky from Buffalo rolling in. They were the most meritocratic group of people I've ever rolled with. I would go to these meetings. Normally they cost $25. I didn't have $25, but I speak Spanish, so I'd go in through the kitchen.

I

Interviewer32:53

Is that really true?

C

Chris Sacca32:54

Entirely true. I had no petty cash to pay my way into these things. A $45 entry fee sounds immaterial to people with a salary, but there are people in this room who don't have a salary right now. $20 is real. I saw people coming in this door. I'm just kidding. Speaking Spanish, I probably would have offered a job to everyone coming in that door. But I would go to these things and hand people a business card. I was wearing a sport coat, tweed. I was bringing it. The card said 'Chris Sacca, Attorney at Law.' People would look at me and say, 'Oh, you're a smart kid. Things will work out for you.' They had no idea. If I didn't make like $2,000 that week, I'd have to move out of my shitty apartment in Foster City back to Buffalo. Not an option. I struggled at this for a while, and then it occurred to me that I had to do some marketing. I decided that my main problem was that I was just me, alone, a young, inexperienced individual. So I created a business. I sat down — it was funny this weekend going through papers, I found the list of names I brainstormed. Most of them were horrible, like characters from a Buck Bonsai comic book. Ultimately, I settled on the Salinger Group. It sounds mnemonic. Everyone says the word 'Salinger' at some point in their life. 'Group' sounds like there's some shit going on there, more than one person. My wife, who was a close friend back then, designed a super hip logo for me. I found a guy on Elance who built a website that said a whole lot of nothing. You can find it on the Wayback Machine. Look for 'salingergroup.com'. It had no physical address because all I had was a shitty apartment in Foster City. No phone number because all I had was a cell phone. It had the most amorphous terms so that anything you were working on, I was of value to you. I had a whole venture division, a media division, and a consulting division in case it didn't fall into those first two buckets. I went out with this awesome business card and started saying 'we' instead of 'I'. I didn't lie about what I was capable of, because that's setting yourself up for disaster. But I just said 'we'. People would see that card and be like, 'Oh yeah, the Salinger Group, I've heard of you guys.' Then they'd hire me to do stuff for them. Before I knew it, I was a very active lawyer, business consultant, and media guy. I helped people name their companies, doing this for equity and cash. It was a business all of a sudden, and it had no excuse being a business. A couple of my clients grew into bigger clients, and ultimately I became an executive at Spedera, the company I worked at before Google. It literally bridged me into that.

I

Interviewer36:27

To be clear, was anyone here unemployed between 2000 and 2003 or '04?

A

Audience Member36:33

My husband was. He was a graphic designer. We moved to Silicon Valley.

C

Chris Sacca36:42

Let's just be really clear, because less that be excerpted out of context: doing legal work for the porn industry. We moved to Silicon Valley in like '99. He got there about the time the market crashed. Graphic design, worst industry to be in in the valley at that time. He beat out hundreds of people for a job designing hooker ads in the back of SF Magazine for $12 an hour.

I

Interviewer37:06

Legit.

C

Chris Sacca37:08

That's serious money back then. No, it was a disaster. For those who weren't around, you couldn't get a U-Haul out of San Francisco because they had all gone one way out of town and nobody was bringing them back. True story. It was just screwed. There was nowhere to go. I would send resumes out and never hear back. A mentor taught me that if someone makes eye contact, they want to talk to you. Go in for the kill. That was incredibly fruitless for two years. Nobody. The disconnect was amazing. One reason I feel kinship with folks who've lost their jobs and houses now is that it wasn't that long ago for me. I remember how friends who had jobs were sympathetic briefly, then went bowling. I saw the world through this lens of 'Holy shit, I have no dollars.' In fact, I had significantly fewer than no dollars. I would do anything for $150 from this company or $200 from those guys. When I heard about people making $65,000 a year, it sounded like a gold mine. I'm sure that's what's going on for a lot of people now.

I

Interviewer38:39

I was at a dinner with Jim Collins the other night. He said that one thing that defines people who are the most powerful in business or politics is that everyone goes through periods where they get completely decked. A smaller percentage will get up, get hit down, and get up again. It winnows down to certain personality traits — arrogance, resilience, whatever. I'm curious in all of these times, what made you keep getting up? Was it ego? Pride? You didn't have the story of someone who moved to the valley and wanted to change the world.

C

Chris Sacca39:31

I guess there are two things I want to say to that. One is that there's a certain narcissism in thinking that cycle only happens to people who have had a lot of success and been great. I think they're the only people whose stories we bother to ask about. Most people... My favorite class in college was ethnography.

I

Interviewer40:00

But to make a point, you just said there were more U-Hauls outgoing. So a lot of people didn't stay and try again.

C

Chris Sacca40:08

No, but I wonder how many of those people gave up. I was probably a week away from having to leave my shit and go home at some point. I think there are a lot of people who are on the edge. I think the stories of bouncing back aren't uniquely for titans of business. People who bounce back from cancer or personal things — there's an entire generation of people who went and fought in wars. They're younger than us now. At any rate, whether you buy the premise or not, what was it that made going home so bad? Why did you have to repay this debt? What kept driving you?

I'm just a little bit irrational about some things. When I was a kid, six years old, my mom and dad took me to hike Longs Peak, the tallest mountain in Colorado you can hike without ropes. We departed the campsite at 3:00 AM to summit it. A storm hit and we couldn't get to the top, about two miles short. I was devastated. I wanted to stay and do it, but it was unsafe — lightning. We had to get below the tree line. When we got back to the campsite, I refused to stop walking. I kept walking until I'd logged the two miles I missed at the top, because otherwise, even at that age, I would have felt like I gave up or lost. I certainly didn't have parents who kicked my ass to think like that. It was just something I genetically had. Evan Williams — when he founds companies, he doesn't weigh success versus failure. Failure isn't part of the equation. Even when something fails, up until the point it fails, failure wasn't a consideration. For me, I just didn't admit that going home was one of my choices. I didn't admit that leaving and getting my ass kicked was possible. Declaring bankruptcy would have been a financially savvy move. Wipe that out, seven years, bust your ass a little, then get credit cards again. But there was something — it wasn't ego. Ego plays into a lot of what I do, but not that. It was just being irrational.

I

Interviewer43:11

So when you started working at Google, that's when people really started hearing about you. That was when I met you. I'm sure that's when a lot of reporters got you on their radar. You always had a reputation at Google for being one of those guys who kind of exaggerated what he was doing. I've seen in interviews and conversations you've sort of advised people to fake it until you make it. That seems to be a lot of what you've described with the Salinger Group. How would you feel if an entrepreneur came in and did that? Do you expect entrepreneurs kind of do that?

C

Chris Sacca43:50

I'm curious what I didn't do at Google that I said I've done. Like anything.

I

Interviewer43:54

I mean maybe it's the 'I' versus the 'we'. This is just something. Maybe it's all people who are haters, but people say this about you.

C

Chris Sacca44:01

There was one hater. There was one guy who used to write this. It was this guy Owen at Valleywag who wrote a series of articles saying I never did anything there. But every time I challenged him to write down what I didn't do.

I

Interviewer44:14

Or like I was busy. I mean I can list the things I did.

C

Chris Sacca44:20

And so...

I

Interviewer44:21

I think it's probably like the IWI thing. I don't think it was an issue of people saying that you said you did things you didn't. I think it was an issue of perhaps taking credit for what a team did. I'm not saying you do this. I'm saying you had a reputation for this.

C

Chris Sacca44:35

Again, I'm curious. Was it anyone other than that one guy? Really? Yes.

I

Interviewer44:39

Did you think that?

C

Chris Sacca44:40

I didn't work at Google. I'm not going to venture a guess. I didn't see what you did. I mean, Google was a free-for-all, right? It was amazing. You didn't really have bosses there and so you could just build stuff without any permission. Job titles were made up along the way because you didn't need permission to have a job title. You just filed for business cards and your business cards came back with whatever title you wanted on it.

I

Interviewer45:07

What was your title?

C

Chris Sacca45:08

I had six titles while I was there. I know this because I just went through... No, I was Corporate Counsel, Corporate Counsel on Business Development, Global Infrastructure Group because I was buying data centers and to look like a lawyer would be pretty douchey. I was Principal and I was Head of Special Initiatives. You know what? I asked somebody recently, there's over 100 Principals there now. I was the first. I made that up. And then there's I think over 100 Heads of. And both of those were... I was doing... I mean, when I did Spectrum, I had a $4.7 billion budget to go bid on wireless spectrum.

I

Interviewer45:51

Do you agree with that?

C

Chris Sacca45:53

Okay. From what I know, I mean you did just up until now talking about generally exaggerating. Skipped the part of my career where I actually became an executive of a company and took a company from the brink of death to being acquired by Okami for hundreds of millions of dollars.

I

Interviewer46:12

You asked the hard questions.

C

Chris Sacca46:13

I know. I'm just saying we conveniently skipped the chapter where I created lots of value. So, we will never get to Uber if we go through that in as much detail. But no, I had this job where I had... I mean at Google they would just give you the rope to hang yourself. You had so much responsibility. When I originally went there, my job was to buy, build, and license data center space, just these server farms, without letting Microsoft know that we were doing it because they didn't want Google to let Microsoft know how big search was. And so we built shell companies and we went and bought the stuff in the names of shell companies. Is that faking it to me? I'm not sure. I'm waiting for you to jump in.

I

Interviewer47:04

You're the one who's advised people of that.

C

Chris Sacca47:06

And so we would go buy these shells, you know, go through these shells and we spent hundreds of millions of dollars doing it. And it's funny, if you call people up and say, 'Hey, I want to buy your data center for $100 million and your title is Corporate Counsel,' people don't pick up the phone. But if you tell them that you're Principal at, you know, Global Infrastructure Group or Head of Special Initiatives, they return your call and so you get stuff done. And so that's how I evolved my title over time to get stuff done. But the responsibilities in that company were like, you know, you'd grab stuff. If you saw it and you wanted it, you grab it. And I think haters and critics, there were people who were trying to stay within the lines. And I could give a damn. I wanted to get stuff done. I loved getting stuff done. I was probably almost fired like three or four very concrete specific times I can remember. In fact, I remember being walked into the full executive management group once. My boss had his arm around me. He's like, 'You need to find a job.' I'm like, 'You mean like somewhere else in the company?' He's like, 'No, no, somewhere outside of the company.' And we walk in there and they were going to very publicly fire me as a sacrifice to the carriers so they didn't upset the mobile carriers because I had been offending them. And just as they were getting ready to fire me, Larry Page is like, 'You know what? You know what Zach has been saying is true. I don't know why we should be apologizing for it. You know, maybe we should give him some resources to go build some stuff that would explore.' And we come out of that meeting and my boss tussles my hair like, 'This is the big executive promotion we've been looking for for you, you know.' So it was the Wild West, you know. It was crazy there. But I got to work on a crazy amount of stuff. I got to buy companies. I got to start products. I got to, you know, we covered all of Mountain View with Wi-Fi so we could start free Wi-Fi that's still used by 13,000 people a day, so that we could start testing location-based ads and stuff like that. I mean, we screwed up the wireless industry and played the biggest hand of poker that's ever been played. And I learned a ton along the way.

I

Interviewer49:25

What do you think about where Google is today? And what do you think about the company under Larry Page versus the company under Eric Schmidt and the triumvirate?

C

Chris Sacca49:34

I think Larry is one of the smartest people ever. Not just alive, but ever. And I think he's been sent to us from the future. Like maybe he won a bet or used some weird fortune-telling machine and got teleported or something like that, but he knows what's going to happen ahead. And he was always the guy who was willing to take unreasonably large bets, just crazy stuff. And it was funny, I think the beautiful thing about Eric Schmidt at that company was that it wasn't that he was the adult supervision. I think that underestimates both him and Larry and Sergey. What he was, was the voice of reason that allowed Larry and Sergey to just go off the deep end with their ideas sometimes and just think about the things that would otherwise be unthinkable. Like, you know, we'd be talking about net neutrality and Larry and Sergey for the academic exercise of it could actually be like, 'Well, what if we just said screw net neutrality and we just ran fiber to everybody's home and that was it?' And now it wasn't neutral and you're like, 'Uh, uh, uh,' because you've just spent the whole last year of your life building arguments for why net neutrality makes sense, right? It's the kind of thing a CEO of a company could never actually say in a brainstorm like that. But because Larry and Sergey weren't ultimately responsible for the crazy stuff they said in those meetings because Eric was always going to bring us back to some rational point. They were free to think of the stuff that was just so off the charts, you know? And so they would just say like, 'Well, screw it. Let's just, how much would it actually cost to ship one of these devices to every American, you know?' And he'd be like, 'Well, $3 billion.' I'm like, 'Well, we have a lot more than $3 billion, so let's just do it.' Instead of advertising and trying to convince people to do it, let's just put one in the mail to everybody, you know? And it's like, my god, regular humans don't think like that. So, what I'm stoked about and worried about is that with Larry at the helm, there's the opportunity for that company to think more aggressively and just wild crazy stuff. Has anyone here been in a self-driving car yet or seen it? If you go to YouTube and look for self-driving car, I think my personal video is one of the top results and you'll see I freaked out in my pants riding that thing for the first time.

I

Interviewer52:13

I'm not going to that video now.

C

Chris Sacca52:15

It's amazing. You have to sign. It's mature content. No, I got in that thing thinking it was going 5 or 10 miles an hour around a course. It goes 45 miles an hour around an enclosed parking garage with walls up and it's a hybrid, but it's squealing the tires with nobody driving it. They've driven millions of miles with those things already. And I heard the other day the only accident was when a human being was driving it. I'm sure these things are way better than people. And so they're way better than me driving for sure. So that's the crazy kind of stuff we can expect from them. At the same time, I worry that without an Eric Schmidt there, I worry that maybe Larry and Sergey feel like now they need to play it safer sometimes, too, and channel what he used to do, right? And so I like the triumvirate. I thought it worked and I haven't been there since 2007, so you know I've only watched from the outside like you, but I really deeply respect those three guys and I think the balance of power worked really well and I just hope that Larry, because he's now the important guy in charge, doesn't back off his edge.

I

Interviewer53:21

Right. And what do you think about... You must know Marissa very well. What do you think about Marissa running Yahoo now?

C

Chris Sacca53:28

I think Marissa is the most capable person to run a company that might not get turned around. I think she's fascinatingly awesome. I think she's a no-nonsense kind of executive. She was one of the few people who could be just really hard and yet still command so much respect, right? I mean, I think there's a double standard for a woman, too. I think it's a lot more difficult for a woman to be just really in your face calling stuff as it is and not be labeled all kinds of names, but she pulled it off. And I think she's just unapologetic for her awesomeness. I just don't know if Yahoo can get its mojo back. I bought some of the stock actually. I bought some of the stock like so I own a little bit of it. But they just lost multiple generations of talent. Like who here would sell their company to Yahoo, you know? Anyone? That's zero hands, I think.

I

Interviewer54:27

Oh, there's one guy.

C

Chris Sacca54:28

Oh, yeah.

I

Interviewer54:29

He's like raised his hand every time we've said raise your hand, though. Just I want to point out.

C

Chris Sacca54:33

The one who's 17, too. Yeah.

I

Interviewer54:34

He's also 15.

C

Chris Sacca54:35

So, I mean, I think they lost it a little bit. I think they... And I actually like Marissa's approach, which is restore mojo. Let's get some free food back in here. Let's give people some non-crappy Blackberries, you know? Let's bring this thing back into the present, make it a cool place to work. And I think that's actually the number one ingredient. I don't think it's necessarily about their ad or content strategy right off the bat. It's just like why should someone work there?

I

Interviewer55:02

Is there anyone she should buy? Is there like a big bold?

C

Chris Sacca55:06

Yeah, it's lowercase.com/posi. Yeah. With all my portfolio companies...

I

Interviewer55:12

You just said who would sell to Yahoo? I want to remind you.

C

Chris Sacca55:16

So, here's the funny thing. When it comes to being acquired, when one of my portfolio companies gets inbound acquisition interest, my number one rule is like stop, don't respond, don't do anything because if you do, you're just playing defense, right? So much of life comes down to offense and defense. If somebody offers you money for your company and you immediately respond, you have just let them set the table completely. They have laid out everything and you're just working with what's given. So I tell my entrepreneurs like walk away. Let's spend a weekend as a team and individually thinking about what do we really want? What matters to us? Money is a nice thing, right? And it's usually on everybody's list. And so we'll put money on there, but is it how much money? Is it how much potential for more money later? Is it money now versus the potential to make money but it might be risky? You know, that kind of stuff. So, we put that there and we're like, what else do you want? To be able to continue to work on this product? Does that matter? Or what if they just shut it all down and you get to work on something else? Does who your boss is matter? Does where you work matter? Like where you have to move to? All this stuff. And we put it all on a list and we rank order it. And then with that list, I actually don't go back into the room as the negotiator. I send the founding team themselves back in because I think nothing is more convincing than an engineer who has already calculated the exact range of acceptable outcomes. You put that guy in front of a hand-wavy MBA business guy and it's totally disarming, right? Because this engineer just doesn't know how to lie. There's no bluffing, right? So they're just like, 'No, that's just not going to work. This is what's going to happen here and that's not going to work.' And they can do it better than you and I can. They're really good at that stuff. And so you just prep them. And what it does, it puts them back on offense. So I bring this up in relation to Yahoo because I had a company recently that established a conversion rate for company dollars. Like a Google dollar, let's say, was worth a dollar. And Microsoft would have to pay $1.5 to every Google dollar to get the deal to go over there because that was their individual team's perception of what it would be like to work there, right? And maybe Twitter dollars traded at a discount, you know, because it's a hip company and there's some upside left. And so, that's just one thing on the spreadsheet.

I

Interviewer57:48

What was the Yahoo dollar trading at?

C

Chris Sacca57:50

Yahoo wasn't a player then. Yeah. I mean, you can't... Yahoo's been absent for a long time. They just weren't a tech company and then they were kind of a media company but not really and they just got lost. They've totally lost their way.

I

Interviewer58:04

So the problem is it's just too late or is it the organization or is the product? I mean what is going to foil her?

C

Chris Sacca58:12

What's the biggest challenge? It is that the company is not owned by venture capitalists, it's owned by hedge funds. Venture capitalists are willing to sit on stuff for years while the ship slowly turns around. And hedges aren't. Like, you know, so when I see the stock tick up, I feel happy for her because I feel like it buys her a little bit more ramp to get the meaningful stuff done. But hedges don't have a long time frame. They need to return multiples quickly, right?

I

Interviewer58:44

I want to talk about Twitter because you played a really important role with the company early on and very good.

C

Chris Sacca58:49

Is this a setup for like am I supposed to take credit for this and then you get to write an article about how I take credit for stuff I do? I love how you have given me total crap for asking basically one hard question and then you just said about Marissa like people get really upset when women are in their face and ask hard questions as you've demonstrated.

I

Interviewer59:07

Really? You think that? You think... No, I'm just... Oh Jesus. You balked at one hard question. There's more coming.

C

Chris Sacca59:13

Well, I think it was a tough question. Yeah. I don't think it has anything to do with you being a woman. That would have been a tough question either way. Saying your reaction to it was funny given you said...

I

Interviewer59:24

I would have reacted differently if a man asked me that question. Is that what you're saying?

C

Chris Sacca59:29

Neither of those... You've now papier-mâché defensive on top of defensive. Let's scale this back. So Twitter...

I

Interviewer59:38

Twitter, I'm not setting you up for failure. I'm genuinely curious about your role early on with Twitter.

C

Chris Sacca59:46

You were friends with Evan.

Yeah. Yeah. So most of the really successful investments on my role of successes were not things I really picked out. They were things I got dragged into. And so this is called the opposite of taking credit by the way in case you were like keeping score. I'm giving some credit back right now. Okay. But I had seen Twitter. I used it. I signed up early in 2006 and Evan went to put a round together and he called me up and was like, 'Hey dude, I'm putting a round together. I put you down for 25. 25 cool. Okay, 25. Bye.' And I was like, 'Oh crap, I don't really have $25,000.' It took me back till 2005 to get back to zero, which is by the way the richest you will ever feel in your entire life. When you were worth zero dollars, you can finally make some choices again. You can join the Peace Corps and no one's going to track you down. No collections agency is up in your business trying to find you. So anyway, I left when I ultimately left Google I was worth like a million dollars which is a lot of money but not a lot of money to be an angel investor. At the time I invested in Twitter, I was still working at Google and technically I wasn't... I didn't meet the SEC's accredited investor test yet. But I checked the box anyway and wrote the check. My first angel investment, by the way, was Photobucket. And I got pulled into that one. And that was a credit card check I wrote while I was working at Google. I wrote a credit card check to Photobucket. That panned out. My second angel investment was Twitter. And Ev was like, 'I got you for 25. Cool.' And I was like, and so I wrote the check. And then I realized, crap, I need this money back someday. So, I better start showing up there and helping out. And so, I just started going to 164 in South Park where the original Twitter office was. No one invited me. I just started showing up and I know I annoyed the crap out of Jack. I'm sure when he does a Pando he'll say that like I was too businessy for his taste. But I just was trying to help out with anything I possibly could because I really needed that money back someday. And so I can't take credit for anything in particular, Sarah.

I

Interviewer1:02:15

You're going to say this from now on.

C

Chris Sacca1:02:17

Yeah, pretty much. No. I tried to help think about ways that Twitter would make money someday. I helped raise money over time. I mean, I spent a couple years just dropping in there. Those search deals, I negotiated those search deals until Dick got hired and then I went and rode my bike cross country and he took those deals over. There was one of the rounds that I raised and stuff like that. So, I just tried to do anything I could and put out fires when possible and just serve. I think good investors are in the service business. And it's funny that I mean one of the reasons why the taking credit thing rubs me the wrong way is because I put so much effort into not taking credit for the things that my portfolio companies do.

I

Interviewer1:03:10

To be fair, I have a big problem with VCs.

C

Chris Sacca1:03:12

I think that was something that was specifically said about you at Google. I don't think it's something that's been said about you since.

I

Interviewer1:03:18

Right on. Okay. I'm glad we dodged that. No. I think like...

C

Chris Sacca1:03:24

But it bothers you when other investors do take credit.

It bothers me a lot. Yeah. The art of self-promotion or taking credit for what a portfolio company has done has reached intolerable levels right now.

I

Interviewer1:03:38

You think it's that much worse now than it was a few years ago? Like wait in line for an industry standard article or something like that? Like nowadays you can just tweet and path out your narcissistic stuff all day long. And so when one of your companies does well to immediately insert your role and what that company did and take credit for the little bit... I mean there are some old school investors out there like I look up to Bill Gurley a lot and we don't have a political bone in common but that guy doesn't say three sentences in a board meeting but the three sentences he says are really high impact and when the company needs something he busts his ass on it all week long, gets it done, doesn't tweet about it, doesn't write a blog post about it, just empowers the entrepreneur who gets all the credit for it. That's the VC role. And I think we could all aspire to do more of that. And there's a generation of VCs who aren't doing that stuff right now. Who have become the stars, you know, who have become like... I mean, how many VCs do you know that have PR teams like literally have PR on retainer? There's something fundamentally broken about that, right? It's increasing. It's totally increasing, just trying to manage image and take credit for stuff. So, and I think that's broken.

So, Twitter is one of those companies I find fascinating because it is, you know, everything people say you should do as a company to be successful. Twitter's pretty much done the opposite a lot of those. And it's the most interesting sort of private consumer company, you know, left. One of Twitter's investors has referred to it as a weed because they've done basically everything to kill the company and it's continued to grow on the strength of its product. You were very close in the early days. I know that you were close during both of the CEO founder CEO ousters. So, I'm curious what your take is on why Twitter continued to succeed, why it survived, you know, three CEOs, the board being turned over, all of this turmoil.

C

Chris Sacca1:05:40

Yeah, a few things. I mean that company should have died like six or seven times for sure, right? But I think the reason it's easy to say that is because... Do you remember when Eric Schmidt said Twitter is the poor man's email? You remember that? It was awesome. Because most founders would get really upset about something like that, right? And I remember I went right over to Ev's house and I was like, 'Holy crap, I get it.' Finally, I get why Google never really respected the Blogger team and why they never really gave him lots of resources and stuff like that. We used to think, is it because those guys didn't go to fancy colleges or didn't go to college at all? Is it because they were SF hipsters and they didn't live in suburban Mountain View? Like why is it that nobody would invest in Blogger, invest Google resources in Blogger, despite it being independently the ninth largest website in the world? Never got the answer until Eric Schmidt said, 'Twitter is a poor man's email.' And then it dawned on me like Twitter is not a hard science problem. It's an art problem. What Google specializes in are science problems and they do it better than anyone on the planet. The stuff they solve with search... I know it always looks so simple from the outside, but the depth of analytical prowess that goes into building that stuff is just second to none. But one of the reasons why Google has always failed at social is they don't understand the art problems. If you think about Blogger, Blogger was a canvas. It was a canvas that you needed an expensive laptop and an expensive internet connection to paint on. And you also need to have a working knowledge of punctuation and paragraphs and stuff like that. But it was a full-on canvas. And Twitter was that just even more accessible with a broader range of addressable participants. And the beauty of Twitter is everything that's not there. And because there's not much there, it's easy to really underestimate it, right? And it's easy to be like, 'Well, they can't keep the site up, so there goes Twitter.' But everything I'm gonna say now for the next 30 seconds is going to sound like a hippie-ish Hallmark card, but the real value there was in the users. The real value is in the community and that movement that was created of expressing yourself there. You can try and dissect it down to this graph or that graph, but it created a venue for people to express and curate and it just didn't exist anywhere else. Everything else was too complicated, right? Facebook tried to tell you what to communicate and how to communicate it and there were too many rules. And to scientists that was more interesting, right? To Google that was a little more interesting because there's some complexity there. Twitter was just so sparse. And credit to Jack for being such a minimalist design weirdo in a way, because that was where the real value came from. And Ev also specialized in stripping stuff away and getting to the real core of it. I mean, if you think about it, Twitter is a metaphysical challenge. Sitting around like what's a tweet, right? That's why in the beginning the growth was linear and not geometric. It was because you're just like how do I explain to you what Twitter is? Because it's very different than what she would say it is, right? And yet Facebook you just get, right? And Square you get like, 'Oh, I see what you do with Square.' But Twitter, you're like, 'Wait, what is this thing?' And I think Jack was the right person to invent that company and get it going. He's definitely a starter. He had a lot of vision. It was amazing. Ev is the philosopher king of product building. Ev thinks more profoundly about community than anyone anywhere in technology. And he questions assumptions that seem so obvious to us that you don't even realize it's an assumption you're making.

I

Interviewer1:09:51

Can you give me an example?

C

Chris Sacca1:09:54

Yeah. Ev and I were considering starting a venture fund together back before Twitter really became a thing. And he's like teach me about this venture business. How does this work? And I was like well this is how it works. You raise a bunch of money and then you get to take a fee, you know, so this is an amount of money you get paid every quarter just for showing up and you get carried interest which is a percentage of the profits. And he's like so tell me why we get the fee. And I was like, 'Because in the documents it says you get this amount of money each quarter.' He's like, 'No, but tell me why do we get the fee?' I was like, 'Because they'll pay it to us.' That's why. And then suddenly Ev was off thinking about a new model for venture capital and he wasn't really up until that point. It was like his first day hearing about venture capital and he's already trying to reinvent it a little bit. I'm like, 'Dude, just let's get the fee in the kitty.' You know, but if you think about what makes Twitter great, it's the things that aren't there. It's all the ways they could have made money in the early days that would have screwed it all up. It's all the buttons that could have been there and would have clouded it up. It's all the files you could have attached to it and all the stuff that Clerk and everybody were doing. I forget what the... there were 32 competitors at one point that everybody else were doing and it was just the absence of all those things. But eventually these things get big enough. There's enough headcount. There's enough real challenges. And there's a business that needs to get built. And so I deeply believe Dick is the right guy for that. And what's unique about Dick is I think it's very easy in contrast to Ev to say Dick is the business guy and Ev is the product guy. But Ev is no spring chicken when it comes to making money, etc. He's done really well for himself. He knows how to get stuff done. He knows how to buy companies, sell companies. He's sharp. And Dick is just not a naive product guy. I mean, people forget Dick is a serial entrepreneur. Before he went to Google, he used to write this blog called Ask the Wizard. That was one of... it was like the Fred Wilson of its time. It was like the definitive blog for entrepreneurs to figure out how to build stuff. He is a product guy through and through. And it's very easy to put them in boxes and say like one's not X and... but Dick has this wide range of talents among which is great product stuff. I learn from Dick when I talk to him about product and I think he doesn't get enough credit for how strong he is there but he's also really good at making money too and building an organization and being a great leader and it shows in his team. All the political stuff went away. The board's cleaned up. The team is really solid and awesome. Business is killing it. The site works. It's just a great phase. So, I think we had three CEOs who were the right CEO for the right phase of the company.

I

Interviewer1:12:40

Do you think it was fair what happened to Jack and fair what happened to Evan?

C

Chris Sacca1:12:44

No, it never is. And, I mean, I keep saying I'm going to relaunch my blog and I have a post in draft and the working title is 'It's All Fun and Games Until You Raise a Series B.' I hate Series B, C, D, E. It's the most political, backstabbing, evil... the cognitive dissonance that happens in that stage of a company is just so painful, particularly when building a company with people you know and love, like in friendships. And I think there's no upside in admitting that in Silicon Valley, frankly. I think we all like to pretend it's a total love fest and everyone gets along and the greatest investors pile up to their entrepreneurs but the betrayal that you can feel in Silicon Valley cuts deeper than any betrayal you'll feel at the seventh grade dance when your date runs off. It's so deep. I have been stabbed by entrepreneurs that have been personal friends of mine. I have watched VCs hang up the phone on one guy, lovey-dovey, and then just cut his Achilles on another call. It's not all love. It's not all hugs all the time. It's real business. The stakes are really high. Forget even the egos. There's just a lot of money on the line, right? There's a lot of power on the line and stuff gets personal and then they all rush to tell their version to the paper. The New York Times article about Ev's role in pushing Jack out is crap. It was just whoever got to the Times faster to tell that story, right? And so no, I don't think the way Jack was fired was fair. I mean, I was there. I was an adviser to the company. I was consulted on it. And the original plan was to just send him on his way. And I was like, you can't. And Dick Costolo was there too, actually. And Dick was the strongest voice of reason. He was like, you can't just send the inventor of the product on his way in the worst business environment in a long time. The guy, you can have arguments that maybe he's not the right person for the company right now, but he invented this stuff and he still has a lot to say about product and he's still a very important voice and an important voice to the community. It was Dick Costolo's idea to make him chairman actually and it was my idea to make sure we paid him a lot of money and got him his own lawyer to make sure that he wasn't feeling screwed in the deal, you know. And I think sometimes VCs who haven't had jobs recently forget about that stuff. But I'm sure Jack still holds grudges etc. and he should. And the way things went down around Ev... I mean, ultimately Ev chose to leave. But the events leading up to that were shitty. And how awful is that to have your company, the company that you've backed from the beginning, to have strangers pushing around and the politics of that? It sucks. And yet it happens all the time. I know the world gets good at euphemizing... is that a word? Euphemizing? Like putting a lipstick on the pig of these HR events and the financings etc. I mean it's just horrible. And I think anyone who tells you otherwise either hasn't been in the game long enough or is just totally full of crap. I think you have to have the thickest skin in the world to play in the startup world. I think even calling it a game is underestimating it. It makes it sound more fun than it really is. It's grueling. You'll lose years off your life. You'll either undereat or overeat. You'll look over your shoulder. You'll get anxious. I mean it's just nuts. And then you'll see those same guys at a cocktail party and pretend to smile. It's not a nice little world. And I figured I would say that just to take it off everybody else's shoulders to say it because it's a tough message to deliver.

I

Interviewer1:17:19

I am amazed in the valley at how many times people really come to some serious blows and then can sort of still be nice to each other. I mean I kicked someone off my board and I'll never speak to that person again. And I talk to people in the valley and they're like, 'Oh yeah, but you guys are still friends, right?' And it's like, 'No, no, no, no, no. What part of this was not bad enough?' Why do you think is it a fakeness? Is it just that people compartmentalize?

C

Chris Sacca1:17:51

I had a lesson in this recently that I didn't talk about outside of Path actually. I will... So there's this guy Brett Bowlington. Are we friends on Path?

I

Interviewer1:18:06

We are. I saw your...

C

Chris Sacca1:18:07

Okay. I'm friends with Brett. So, in like 2005 or 6, Brett Bowlington betrayed a confidence of mine. He was an angel investor. I told him something confidentially. He leaked it. It screwed up a deal I was doing, an angel deal I was doing while I was still employed at Google. And I was very pissed off about that and I just held a grudge. And Brett wasn't a central figure in Silicon Valley. So it was actually an easy grudge to hold because I didn't run into him a whole lot, etc. And he would try and friend me on Facebook and I would just ignore it, you know, and he'd send me a pitch every now and then and I would pay no attention. And everybody knows Brett, says he's a great guy. But he just objectively betrayed me. I rode my bike cross country in 2009 and Brett followed my tweets and heard about that trip and got inspired to do it and so he left on that same trip this year and he wrote me a couple emails. He's getting ready to go on that trip and I ignored them. Because Brett was an asshole to me in 2005. A couple weeks ago in Missouri, Brett was riding his bike and had an accident. His GPS says he was going 27 miles an hour and he landed face first on the road. And has essentially been in a coma since then. And I just remember thinking, why did I hate this guy again? Because it cost me some shares in a crap company that doesn't even exist anymore. To make more money to buy stuff I don't really need. And so that's why I didn't like this guy who was about to undertake what I consider one of the most meaningful, cathartic journeys of my entire life. And here was this guy who was joining my tribe, right? And I ignored him. So, it's funny how deep those betrayals go and as personal as they feel, how meaningful can they really be, you know? And I think, having a kid, I have a one-year-old, you have a one-year-old. That changes a little bit of perspective. Reminds you of some things that matter like dealing with life and death, dealing with people who are sick, dealing with people who are extremely poor. Returns some of that context to you. And I still get really pissed off. I'm definitely part Italian and I still get enraged and want to stab people when they betray me. And I still hold grudges, but they just feel so shallow in that context, you know? And so I think that's why lately I've been looking past people who've been total dicks to me at some point. And also reaching out to people that I think I've been a dick to a little bit and just trying to bury hatchets. I got a yard full of hatchets all on the ground.

I

Interviewer1:21:36

Well, thank you for sharing. I read that on Path when you wrote it and that was actually when I found out about Brett because I'd been traveling a lot and I was in the airport with Paul Carr flying back from a New York Pando monthly and he had gone to get me coffee and he came back and I was crying and he thought it was some maternal thing and I was so choked up I couldn't even talk about it. But it does put a lot in perspective. It's hard for me. I mean when you're building a company that betrayal is acute. And that betrayal is more acute than I think two investors squabbling over a deal.

C

Chris Sacca1:22:08

Well, I think you underestimate that. I think this is another one of these things where put yourself in everybody's shoes and it's just hard to say that your pain is harder than their pain, right?

I

Interviewer1:22:23

A fair point.

C

Chris Sacca1:22:26

When 63 people die in a storm, all 63 of those people matter just as much as the others. Each of them have a story that maybe they didn't invent something, maybe they didn't go to the right college, but they're people. And I think an admin getting laid off feels an intensity of pain that maybe a more intense pain than a squabble. But it can also go the other way around. Like when I go out to raise money for my fund, it may seem easier than raising money for your company. When you raise money for your company and somebody says no, internally you can blame it on the company. You can be like, 'Oh, they didn't like the idea, my strategy.' When you go out to raise money for your fund and your fund consists of you and you say, 'Hey, give me some money.' And someone's like, 'I'm going to pass on this one,' it's because you suck. There's no other explanation for it, right? So talk about taking something personally. They have just rejected specifically you. And then there are like... I mean AngelGate... Ron Conway raised most of us in the industry. I wouldn't have been where I was in the industry without Ron. And he was not only my professional nexus but my social nexus too. And when AngelGate happened, my head spun as well as everybody else. I wasn't even there by the way, I was delivering a speech on the east coast, but the grenade shrapnel got me. And that stuff hurt for the longest time. I had an identity crisis like can I...

I

Interviewer1:24:11

What hurt? That it came out? Ron's response? What?

C

Chris Sacca1:24:15

No, not Ron's response. Just basically that he cut a bunch of us off. A guy who we'd done a lot of business with, who I felt like I had a mentor relationship with, who I used to share deal flow with and stuff like that. After enough of that it becomes beyond professional and I really look up to that guy. And when he kind of disowned some of us, that really hurt. I had an identity crisis. Like, can I be successful in Silicon Valley without Ron Conway? Was a question I quite literally asked myself and other people out loud. It hadn't occurred to me that I could do it without Ron before, you know, and I know I had that conversation with other super angels who are well-known and probably wouldn't get on the stage and admit that. And that felt really intense. To have a guy like that come after you is pretty intense, right? Has he come after you before? Oh, no. Actually, he has. Yeah.

I

Interviewer1:25:14

Yeah.

C

Chris Sacca1:25:14

But it was a long time ago.

I

Interviewer1:25:16

Okay.

C

Chris Sacca1:25:16

We... That hatchet is in the yard. Yes.

I

Interviewer1:25:18

Okay, cool.

C

Chris Sacca1:25:19

I bury most hatchets. It's one or two that I have a hard time.

I

Interviewer1:25:22

Can we get back to talking about fun stuff?

C

Chris Sacca1:25:24

Yes, we can.

I

Interviewer1:25:26

Is part of this stuff the reason you moved to LA? I want to talk a little bit about the move to LA because up until recently, a lot of people didn't even realize you were down here.

C

Chris Sacca1:25:33

I'm not always down here to be clear. But I'm down here a lot of the time. We were back and forth between here and Tahoe. Right. In 2007 though, I don't know if people realize this because all of you still write me emails asking to meet me in San Francisco, but in 2007 I moved to a town called Truckee near Lake Tahoe. So, I left San Francisco full-time. I did that for a very specific reason. And it goes back to offense and defense. So, I'd left Google. I was going to do this investing stuff, but I realized I was living out of my inbox. All these messages were coming in asking to get coffee, right? And I could have spent my entire day and then some getting coffees and never have accomplished anything at all. And my friend Jason Shell once expressed it, I'm paraphrasing, but basically he said, 'Your inbox is like publicly posting your to-do list for anyone else to add an action item to it.' Right? That gets attributed to me a lot, but I want to make sure I don't take credit for that. That was Jason Shell.

I

Interviewer1:26:36

This is going to go on for like 10 years.

C

Chris Sacca1:26:38

Sure. But it's true. Think about your inbox. Think about what's in there. None of that is related to what you actually want to get done. It's everybody else needing something from you, taking a piece of you, right? You've got a to-do list somewhere. Whether you're thinking it or you've written it down, that's all the stuff you want to do. You want to travel, you want to write a book, you want to finally ask that girl out, you want to do all this stuff, right? But that's all on this list. And yet your inbox has none of that. It's just a bunch of people who need TPS reports from you, right? And so I realized I was running out of excuses for not getting coffees. And so I was like, 'Well, screw it. If I don't live here, I can't get coffee.' And so I bought a little house and I moved up to Truckee. And now I had this really cogent response for why I couldn't meet people. And I was like, 'You know what? Instead, just send me your deck.'

I

Interviewer1:27:33

You used it on me several times.

C

Chris Sacca1:27:35

Yeah, it was genuine. I mean people who drove up there I met with actually.

I

Interviewer1:27:40

Well this is one thing that interested me in having you here at All Things D. You were talking about how living in LA and Truckee had actually increased your ability to close deals because you would spend more quality time with people.

C

Chris Sacca1:27:53

Yeah. So going on offense... Defense is your inbox, right? Going on offense is looking at your to-do list before you look at your email. Everyone here gets up and they check their email, right? I mean, there is science that says it... I get up and I check my email. But going on offense is looking at your to-do list before you look at your email.

Dopamine release. Even if it's just a bunch of like the new J Crew catalog and Fab and like you already missed the sale and shit like that. It's just like you still are like, "Hey, messages for me. They've got my name on them." And so there's like science behind that. And so it's hard to like not look at that and start your day from your to-do list. Like what am I actually going to do today? Maybe write it the night before. But if you take that and expand that concept, it was like I realized I was only going to dinner parties that other people were organizing. I was responding to social invitations but not hosting my own and not spending time with the people I really wanted to spend time with. I was only reacting to other people's invitations. And so I was like, "All right, if I move to Truckee, three and a half hours drive on a clear day, eight hours on a snowy day away from San Francisco."

Then what I can do is I can take the people who I really want to get to know better and invest in more and get them to come stay at my house. And you can learn so much more about somebody when they stay at your home. Like cooking, you know, like hanging out in the hot tub, jamming, going skiing, going for hikes, whatever. And really deeply getting to know each other and deeply going and thinking about the product is a way to go deeper with people than has ever been possible in the casual Silicon Valley setting.

And it's true. And when I think about the friends I've gotten to know much much better, the entrepreneurs who I've gotten infinitely closer with, almost all of them have come and stayed at our house. You know, my wife moved up with me there. I mean, she now my wife, but then my girlfriend in like 2008 and it got to the point where our house was full of like young coders a little too often. So, I don't have an office. So I basically took what a normal VC would budget for an office and I bought the house next door and I call it Camp Lowercase and it's a retreat for the entrepreneurs in our portfolio. Anyone can go use it at any time. And so I get all the upside of them staying with me, but I still kind of get my own bathroom and stuff like that. And it doesn't smell like young engineers.

I

Interviewer1:30:20

I always... You know that smell?

C

Chris Sacca1:30:21

Oh, I do. Well, but it's young reporters in my case, which is just as bad. Because we're a startup, whenever our reporters come in town for the Pando monthlies and stuff or when we do retreats, I make everyone stay in my house and we have to have a janitorial crew of about eight Salvadoran women who come in afterwards and just scrub it. I mean, it's one day Anie and I were going over financials before a board meeting, and it was like one of my first board meetings ever, and I'm completely stressed out, and one of our 19-year-old reporters just kind of ambles stretching through my dining room wearing boxers and a tank top and then grabs his pants off the dining room table. And I was like, what has happened to my house? So, I know that smell well.

I

Interviewer1:31:04

Nice. Yeah. So, he loves when I tell that story. What's the hashtag cool story, bro? Yeah.

C

Chris Sacca1:31:16

You asked. I need to know. You're just being a dick to get back for that question.

I

Interviewer1:31:21

All right. There's like three more things I want to ask you about for sure.

C

Chris Sacca1:31:24

Is there a time limit to these?

I

Interviewer1:31:25

I mean, we're like so past. No, there's... It's... Will people stay seated? And they're still seated. So, there's three more things I want to ask you about for sure. And then I want to...

C

Chris Sacca1:31:32

And then do they get to ask questions? Okay, good.

I

Interviewer1:31:33

Yeah, you're here for a while.

C

Chris Sacca1:31:35

No, that's good.

I

Interviewer1:31:35

Be glad you don't have a baby sitting on your bladder. So, the...

C

Chris Sacca1:31:39

Do you need to take a break? We...

I

Interviewer1:31:42

I'll be fine.

C

Chris Sacca1:31:42

Paul would definitely come up here and entertain. I have no doubt.

I

Interviewer1:31:46

Are you sick of me? Do you want Paul?

C

Chris Sacca1:31:48

No, he could be like your Ed McMahon, though. You know, like he could just be like your Andy Richter and just throw shit out from time to time. Ed McMahon.

I

Interviewer1:31:56

Okay. We haven't explicitly talked about Lowercase Capital. We've talked about you as an investor. You know, when you first launched it, my... this is an IW question again. Yeah.

C

Chris Sacca1:32:08

Is it?

Well, Lowercase Capital consists of two people, right? Me and my COO who runs the back office from day to day. Yeah. So, I guess we're a we.

I

Interviewer1:32:19

You're officially a we.

Is this the only two-person firm that manages a billion dollars?

C

Chris Sacca1:32:27

I don't know. That's a weird question. Do you have interns who can fact check shit like that? I don't know. It's probably unique for what we do and it's probably unique for this space.

I

Interviewer1:32:39

And how would you describe what you do?

C

Chris Sacca1:32:42

I get pulled into investments that I later get to take a lot of credit for. I work with young companies to do... I try and work with outfits to get them to a point where I'm no longer needed, like where I'm obsolete. Josh Kopelman, who's a mentor of mine, says he wants to be unnecessary by the Series B, you know, and I've tried to model myself after that. So, I meet young teams who don't have a business guy. Maybe they don't have a true user experience guy. Maybe they don't have a conversion guy or gal, by the way, I'm using it interchangeably, but they just don't have some of those members of the team. And I can do enough of each of those things to be dangerous and maybe get you to your Series A, you know. And so I come in and just do what needs to be done, whether it's helping raise money or sell the company or redesign the front page or do some multivariate testing or work on the growth, or get the message out by calling people like you and saying, "Hey, these guys are worth paying attention to." Or just generally talking them through when their boyfriends or girlfriends dump them, you know, that kind of stuff. And like, okay, get back to coding. But I do all of that stuff, you know. What I don't do is like when I brought up Bill Gurley, we were in a meeting recently where a company was looking for a CFO and Bill Gurley opened a folder and had resumes from five or six CFOs who were ready to go. And I was like, "Holy shit, I don't know five or six CFOs, let alone those who are vetted and ready to work at a company like this." It was amazing. There are guys who add value at a scale, like building out a serious management team, building out a board that's worthy of an IPO and stuff like that. That's not what I do. I get stuff going. I think sometimes VCs don't want to admit that there's a point where they become useless and so they hang on because it's really cool to still be on the board of that company. So, one of the things I do is I'm not actually on any boards. And I just say to the company, "Look, we're going to have a great relationship up until the point where you find me useless and then you'll just stop inviting me to the meeting." And that happens. It happened to me recently, I'm just not as useful to that company anymore. But in the beginning, we don't need a document that says I'm a board member to dictate our relationship. You're either going to call me to be helpful or not. You know, we're either going to be close or not. So that's what I do on the early side. On the late stage side, I do a hodgepodge of stuff. So, one is I write very big checks to late-stage companies that you probably haven't paid much attention to yet, but I know are experiencing geometric growth, and I want to fund them under the radar before anyone else is paying attention. I like to invest opportunistically. If everybody's here, I'm there. And so I have put a lot of money to work doing that and it's been very successful.

I

Interviewer1:35:47

What's a very large check for you?

C

Chris Sacca1:35:51

I've written a $400 million check. But traditionally like 50.

I

Interviewer1:35:58

And that's just you. There's no syndicate.

C

Chris Sacca1:36:01

No, that's me. And that's a fun... You can go look at SEC filings. You know, it's my name.

I

Interviewer1:36:06

You have to list who your partners are.

C

Chris Sacca1:36:08

It's me.

I

Interviewer1:36:12

It's we. No.

C

Chris Sacca1:36:14

You and the Salers. But no, it's... that was a weird part of my business that happened by accident. That was not part of my master plan. But I saw I started buying a lot of Twitter as people were leaving the company in the early days. They needed a little money for a house. So I wrote them a check out of my checking account. I became increasingly bullish. So I got pulled in the first round, but then I started to get it was like, "Okay, this is a thing." And I ran out of money. I quite literally didn't have any money left to buy Twitter shares. So I went out and raised a fund just to buy Twitter and that was 11 million bucks and I put it all to work and then I raised another one that was 40 million bucks. Then I raised another one that was 25 and then six and then a bigger one. And in the process of raising money for that, I kind of developed a thesis that Twitter wasn't the only company this would make sense at. So I went and raised against that thesis and talked some people into doing it. And I never put on a suit by the way during that whole process. I only dressed like this.

I

Interviewer1:37:13

Like an unemployed rodeo clown.

C

Chris Sacca1:37:18

Well, you look a fancy one tonight. You have the black cowboy shirt on.

Same brand though. This is always... I always wear the same brand. It's Skully. Available at vintagewesternware.com. As a matter of fact, I'm not an owner, but they take care of me. But yeah, it was an accident that that happened. I don't really do that anymore because so many other people are doing it. So I do other things opportunistically that other people aren't doing.

I

Interviewer1:37:42

Mh.

C

Chris Sacca1:37:43

And that's what I try and do is just go where other people aren't. So...

I

Interviewer1:37:48

How much of Twitter do you own?

C

Chris Sacca1:37:49

A lot.

I

Interviewer1:37:51

Greater than 5%?

C

Chris Sacca1:37:53

Yeah.

I

Interviewer1:37:55

Guess we'll find out when that...

C

Chris Sacca1:37:56

I guess we'll find out someday. Yeah.

I

Interviewer1:37:58

Do you think Twitter's going to go public anytime soon?

C

Chris Sacca1:38:01

This is one of those questions where I think if I answered it, I would be in trouble. Go to jail.

I

Interviewer1:38:05

Yeah.

C

Chris Sacca1:38:05

I think Twitter should be an independent company. I'm opposed to Twitter selling the company to anybody. The company has a lot of money on its hands and is in no rush to go anywhere anytime soon. The business works. They're recruiting the best talent. They don't lose recruits to anybody in the valley right now. And so why fuck that up right now, you know? Like why take on the headache of everything that's involved with an IPO? But at the same time, it feels like Google to me. It's an easy thing to underestimate and I know that's a weird thing to hear and it's easy to be like 140 characters what? But it feels like Google did when Google was just about to blow the fuck up and go big. And anyone who's not convinced of that can just give me their Twitter stock. So...

I

Interviewer1:39:00

You're still buying Twitter stock?

C

Chris Sacca1:39:02

I still buy Twitter stock.

I

Interviewer1:39:04

Can you tell me other sectors that you're writing these massive 50 million to 400 million checks to?

C

Chris Sacca1:39:09

I'm not writing those anymore other than just I still buy Twitter stock off people, but too many people got into that shit. Like I was never a Zynga shareholder. But you know, people were trading Zynga at 11 billion right before it went public and I think it's worth one and a half or $1.75 billion today. It got really popular, hedge funds thought they were VCs and investors became traders and shit got crazy. So when the money all goes somewhere, the prices go up and there's no money left to be made. And I think there was another phenomenon where an entire generation of VCs didn't have hot companies on their websites anymore. So they all came in and bought shares in hot companies really really late and really really expensively just because they needed to buy their way back in and rebrand a little bit. And so it's depressing. I hope you're not an investor in any of those.

I

Interviewer1:40:05

Yeah, me. I'm not an investor in anything.

C

Chris Sacca1:40:09

Too bad.

I

Interviewer1:40:10

Poor reporter. I don't have the money for that.

C

Chris Sacca1:40:13

But the other thing I pay attention to is the intersection of technology and media. So I actually have a fund that focuses on LA. And until you mentioned it, I don't think I'd really told people that I lived down here half time. I've just been kind of under the radar going to stuff but not really telling anybody. But I've done a few deals in town at the intersection of media and tech. I think enough, you know, I don't want this to be a self-fulfilling prophecy and ruin the opportunity, but I think there's this culture down here where VCs up north have all had their asses kicked by media at least once by media investment because media investments used to be about piracy, basically. And so they've all lost their asses before and so it's got this bad name down here. But we've got this entire generation of digitally native content. VCs up there have lost their asses because they've invested in online media where there were no viewers because it was so hard to have the right media player and the right codec, right? And like enough bandwidth behind it and Flash solved all that. HTML5 on top of that now. And so we have big audiences now. VCs up there all lost their asses because no advertisers wanted to advertise on any of this shit. But you look at companies like Rev3 now and guys like Big Frame and stuff and they're literally commanding TV level CPMs on a lot of their media. VCs up there didn't want to invest in this shit because there was no real revenue model to monetize premium content. You got companies like VHX who are building some of the easiest payment gateways to sell content ever. And Aziz Ansari is launching his comedy specials there. And you put all this together and it's like there's just so much inertia up there preventing people from coming down here and investing. And then you look down here and there's a few LA native firms that are doing it but a lot of the content companies and studios and agencies themselves have proven they're not very good venture capitalists per se and they make better partners etc. And there's just this kind of void where true technology companies in the media space have been just kind of ignored for a while. I mean, this is one of those companies here, Zefr. I mean, they have a bunch of engineers who have built systems to optimize claiming and monetizing content. And it's like companies like that don't get a lot of attention down here, you know, and yet they're a little bit ignored among the legacy investors up there, right? That company's broken out and done really well. But it's an opportunity that I've been exploiting.

I

Interviewer1:42:56

How big is your LA fund?

C

Chris Sacca1:42:58

I don't think we talk about it specifically, but it's big, you know.

I

Interviewer1:43:06

Was I supposed to say more? Oh, that would have been nice.

C

Chris Sacca1:43:09

Yeah.

I

Interviewer1:43:10

What else are you doing right now? Are you still doing traditional seed investing? Are you still backing valley companies? You're not doing the larger checks as much. Anything that you're doing that's sort of not where the crowd is?

C

Chris Sacca1:43:21

No, I'm doing traditional seed companies. That's most of my time right now. But that market got ugly for a while. There was just a real sense of entitlement in the seed industry. I got really tired of having people tell me that their company that was 12 weeks old is worth 11.5 million pre. And then I had to decide right there over that initial meeting or over that initial phone call whether I was in or not because the round was already soft circled for everybody. And maybe they could find 25 grand worth of room for me in that company. And it was just like the whole balance of power had gotten thrown off. I mean, I think Paul Graham has been one of the most positive forces in startups ever. And he shifted the balance of power away from the business speakers to the coders. In the first generation of the web 1.0, it cost millions of dollars to write your first line of code. So you had to raise money on the back of a business plan. That business plan had to be written by an MBA. That MBA took it to a venture capitalist. The venture capitalists back then were ex-bankers because they needed to be the ones with the bankers who would ultimately take you public and shit went public every week, you know, it was crazy. It was like this whole kind of Wall Street orgy. And when that all got shut down, all the fair weather banker guys left town and guys like Paul Graham stepped up and went to the coders and said, "You know what, I can actually teach you this stuff. It's not as complex as you think it is. I can demystify the legal papers and I can demystify the business terms and you could be a business guy even though that may not have ever been something that occurred to you even though you were kind of a math geek up till now." And so he created a whole new generation of empowered entrepreneurs that I think was amazing. And it helped shift who the successful VCs were now because a technical founder wanted to interact with an experienced product or technical VC, right? Whose job was not to take this thing public because nothing went public forever, but instead to convince a product or technical head at one of the kind of six or seven usual suspects who would acquire your company to buy it. And so it shifted the entire demographic who does this work. And that was a really healthy shift. But along the way there was nothing to keep, there was no check to balance out the ego and entitlement that happened with a really young generation of entrepreneurs. And we have I think the widest range of people who have been attracted to this space because it's cool and there's a lot of money to be made. So we've got the people who would have been here anyway. And then we've got the people who when they get a bad performance review, their mom calls up. One of the things I think happened that really fucked the valley up is that when I was... So I'm 37, right? The generation my age at Google that had computer science degrees still had summer jobs when they were growing up and worked during college and waited tables and mowed lawns and washed cars and shit like that. They'd actually worked before. There's a generation below me that when they went to computer science at the big schools, their programs were fully endowed and so they had all kinds of grants. They didn't really pay to go to school. The toughest job they ever had was TAing a class. And we saw this generational shift. These people would come to Google and treat our chefs like absolute shit. We had 600 full-time chefs, many of whom had post-graduate degrees themselves. And they would absolutely bark at these people with this entitled, "We're out of fucking pheasant. What?" And it just got bad. And I've seen that entitlement start to creep into the startup culture. There are the actual killers, guys like Kevin Systrom who just is a slayer who worked by himself alone at Pier 38 for a long long time on Bourbon without getting any credit for it and taking a big risk in doing it. And then there are the fairweather dudes. I haven't seen this new Bravo show with the trailer. I think we're in poser town. And I've just seen a generational shift that I think is poisonous. And so I've been very very selective about seed-stage stuff, putting more effort than before into getting to know the personalities of the people I'm backing. And making sure that they're real. But I've been doing deals, a lot of deals. I think there are some pretty fascinating powerful people in their early 20s who are just crushing it right now.

I

Interviewer1:48:20

Do you think that balance of power is shifting back at all? There's a lot of wishful thinking on the part of seed investors that the impact of the Facebook IPO would have trickled down and diminished some of that and I've heard it's not really happening.

C

Chris Sacca1:48:35

It kind of is. It moved from a maximization exercise to an optimization exercise, right? People are starting to realize... I think the role of the value added investor was kind of lost along the way where kids would go raise party rounds where there was no lead investor. And it was awesome, they would just stand at a YC or something and be like sign up here if you want 25 grand and before you know it you've taken 50 25 grand checks but there was no one actually there to work with you. And taking checks from angels at 25 is great and when you call upon them for help they'll help you, but there's no one there to keep you honest, to come back to you every month, be like, "What did you accomplish this month? Let's have a fake board meeting, but talk about what's going on next month, what problems do you need solved, etc." And so without that kind of counterpart, shit goes sideways for a while. And it can kind of get lonely. And I think there's a bunch of founders who realize it may have felt cool taking money from the widest number of people at the highest price possible, but they're missing something from the equation, right? And that's an actual partner in your business. And so I think we're seeing a shift back to it's not necessarily about taking the most amount of money, it's about hopefully getting the right people involved and then keeping them honest on the price. They're not taking advantage of you. Sahil Lavingia from Gumroad raised around at far less than he could have from the broader market but to make sure that he got a chance to work with a group of us that he considered helpful and valuable to him and then later went and did a big round with KP. And I'm seeing that happen more often now, that rationality's returned. But meantime, at the middle to late stage, it's so easy for a company to say, "Oh, we're at 300 million now. We're going to raise at 800 million in a couple months." And 800 million is a lot of money. And there are very few companies that exit for a multiple of 800 million. There's only a couple on this latest generation that have a chance of doing that. And I think it's just been very easy for VCs to forget that. And in the essence of trying to pad their own reputation, just throw more money at it. And hopefully, I mean, think of how VCs get paid, too. They get to place a lot of bets and if those bets don't pay off it doesn't matter because nobody realized those bets didn't pay off until they've already raised their next fund. So they get to spread their bets across a few funds and if any of those pay off they get paid on those and they don't have to offset their losses against it. It's a totally rigged awesome game. Oh and by the way they get to take like 20% of all of that just off the top for playing. And so it's a really awesome game. And so their incentives are place big big big bets on big big big outcomes. And if they pan out, they get rich. And if they don't, they don't have to cover their losses. And so it's really easy for a VC to walk in and be like, "Hey, I know you think your company's cruising along at 300 million now, but let's put in some more money, valued at a billion, and let's go big." And VCs who say that, it's just very easy because A, they have portfolio theory. They've got a bunch of different companies that may pay off. And B, VCs are already rich and so it's so easy for them to look you in the eye and be like hey man don't be a pussy let's do this, let's roll the dice and go for it and you can be a billion dollar company. And yet there's nothing to hedge, you know, whereas you might. And so I think that's driven this mania in the BCDE stages where there's just no coupling of the prices to the actual outcomes at all. All fun and games till you raise a Series B, you know.

I

Interviewer1:52:17

All right, I want to go to questions from the audience and I have one more thing I have to ask you about because...

C

Chris Sacca1:52:22

Oh, yeah. Paul Carr was just about to go on.

I

Interviewer1:52:24

Total... we I won't put an adjective on it, but we've been writing about Uber quite a bit on our site lately and you don't say you are a significant investor in Uber. I think this is interesting particularly with you because I've been having a lot of conversations with Uber and Uber's investors, not surprisingly, but you are very well known as a very proud Democrat who played a big role in Obama's election. You're very political online. A lot of Paul's thesis is that there's this Randian libertarian streak of libertarianism that's co-opted disruption in Silicon Valley and he puts up Uber as sort of the poster child for that. That seems philosophically at odds with a lot of the things you believe. I'm curious where you stand on all this.

C

Chris Sacca1:53:15

I mean, I've read all these pieces and a lot of them focus on Travis Kalanick, the co-founder and CEO of Uber. Travis has the Atlas Shrugged book cover as his avatar on Twitter.

I

Interviewer1:53:33

Fountainhead.

C

Chris Sacca1:53:34

Fountainhead. Yeah. Sorry. So it's not speculation that he's Randian or whatever. And I presume that Travis and I probably won't vote for the same person next week. But I mean there's a couple different ways... On a personal level, I can see multiple phases at my life where the commons have made it possible for me to thrive or continue. I mean, when I got laid off in 2001, I collected unemployment. It's not something you brag about when you're collecting it, right? You wait till you make a lot of money and then you tell that story about how the government took care of you. But there's so much stigma attached to it. But I would not have been able to stay in Silicon Valley had I not filed for public benefits. Period. End of story. I went to school on federally subsidized student loans. My parents and I wouldn't have been able to afford to pay for college had I not borrowed money from the US government, loans from private lenders guaranteed by the US government. It just wouldn't have been possible. And we'll forget roads and bridges that we didn't build. But I think sometimes arguing with libertarians can be really frustrating because I think it can be intellectually lazy and it can be convenient. In the same way that when everything's going right it's easy to attribute it to your own success and when things are going wrong it's because you got fucked or you're unlucky. I think sometimes the libertarian point of view can be rooted in a limited set of circumstances where you give yourself a little more credit than you're due probably. That said, to come back to Uber where that breaks down a little bit for me... I deeply believe in a regulated world. I like to say things as reckless as abolishing the EPA is just reprehensible. And I'm sure none of you will vote him in as president. But I've worked firsthand with Uber and these taxi commissions now and have been asked by the team to help when I can and have been in meetings where the nature of these rules are made clear. And they're almost all entirely corrupt. I mean, corrupt is not a word I use lightly. I think the carriers are a real pain in the ass, right? And the way they manipulate rules, etc. But it's kind of like a savviness. You have to respect their evil genius at how they do this shit. Like, oh foiled again. And so when I fought those guys, they were kind of like I could respect them as an adversary. But what goes on at the taxi commissions is disgusting. I don't know if any of you followed what happened in DC, but the commissioner made up a bunch of shit. Couldn't point to the rule that Uber was supposedly breaking. Seized a car from an Uber driver. Remember that car doesn't belong to Uber. It belongs to the poor guy from Virginia who is driving it. So they take his car from him and then can't point to the rule that was broken at all. And once they get so frustrated they can't point to the rule that's broken, they go and write some very specific rules that are called the Uber amendments, literally what they're labeled, that are written just to make sure Uber can't do business in that town. They have no actual basis in providing more universal service, regulating price. In fact, the DC rule said that Uber's price had to be x times higher than any other service offered in the town. Who the fuck does that? How can you possibly as a city representative mandate that a price has to be higher than a certain level? And so I think when you've been working in the face of that city after city, you probably walk into a city with the default assumption that the people working against you don't have the best interests of their citizenry at heart. And I think I have enough data points now in interacting with these cities that at least at the taxi commission level that's true. It's been controlled by these taxi lobbyists that have just written shit in play. Who is happy with their taxi service anywhere in America? Nowhere. They're not really happy. Ask them how many 311 calls they get on the report a taxi line. Ask them what the level of satisfaction is with that service. People choose it as a way to get around that city, but nobody at scale is going to tell you that they love the New York taxi system, right?

I

Interviewer1:58:59

I actually don't think that's true. I know a lot of New Yorkers who all you have to do is go outside of New York, come to San Francisco, you will love the New York taxi system. And I think this is the point. You're saying that's just like false logic. Saying like getting poked in the eye hurts a lot less than getting nailed in the shins.

C

Chris Sacca1:59:17

No, that's not what I said. That's not what I said. And you're trusting my words. There's just clear data that at scale the New York taxi system is not solving a problem. Can you catch a cab at 4:30? Have you been able to catch a cab at 4:30? The taxi system is not solving a problem.

I

Interviewer1:59:33

It's not solving a problem.

C

Chris Sacca1:59:34

It's the only city where I can walk outside and other than shift change immediately get a cab. The fact that there's regulations around it that it's a $50...

I

Interviewer1:59:42

When do people's work days wrap up traditionally?

C

Chris Sacca1:59:46

Isn't it weird that it's during shift change? Isn't it weird that that entire market...

I

Interviewer1:59:50

I think they're not solving any problems?

C

Chris Sacca1:59:54

No. It's pretty actually amazing how well the New York taxi system...

I

Interviewer1:59:57

But if it were really a market, don't you think maybe there'd be cabs available at the times when people are leaving work? Or is it weird that the cab drivers actually stop working at the same time that other people stop working and need transportation? That's surreal.

C

Chris Sacca2:00:10

Let me ask you this.

I

Interviewer2:00:13

Let me ask you this.

C

Chris Sacca2:00:14

They're everywhere at 3:00.

I

Interviewer2:00:18

First of all, I can't think of a time I've left work at 4:30 in my career. But let me ask you this directly because this is what we have heard from people very close to the company that when it came to DC everyone was behind Travis's behavior and how he took on the city because it was fucked. When it came to New York he went off the rails. And if you look, that's when sentiment changed around the company.

C

Chris Sacca2:00:44

Well, sentiment changed around the company is a very strong phrase because I've read your pieces. I think they're very interesting, but to say that there's been a sea change of sentiment around Uber is a really bold claim. It's taking a lot of credit.

I

Interviewer2:00:57

No, no, I don't think we are taking credit. In fact, I'm not at all. I know you're taking an opportunity to make a joke, but I don't think we are. I think we hit on a nerve that a lot of people were feeling because when I've written stuff or commented negatively about Uber pre-New York, man, do you get angry letters because people loved that company. When we published our first article on that, I thought we are going to be in such a shit storm and we weren't quite the opposite. And if you got the volume of emails we got... We're not alone, Chris.

C

Chris Sacca2:01:30

I completely understand.

I

Interviewer2:01:33

No, I don't think it's a sentiment at all. I'm not claiming credit.

C

Chris Sacca2:01:37

It's a company that grows by leaps and bounds. People use it religiously. Once you've ridden Uber for three times, you'll ride it for the rest of your life. And I don't think there's been a big shift in sentiment. I mean, it would have been the same shift that happened New Year's Eve when they didn't advertise surge pricing that well. That might have been a big shift in sentiment. I was really worried. I mean, surge pricing makes sense in terms of balancing supply and demand. It wasn't communicated very well.

I

Interviewer2:02:05

No issue with how they've handled the New York thing at all. You think it was the same thing as DC? He was fighting for the common man.

C

Chris Sacca2:02:12

No, no, no, no, no. So, but you're asking about... I'm talking about a shift in sentiment. If you want to talk about the New York thing, I just think to say that people are surrounding Uber with torches for whatever, you know.

I

Interviewer2:02:24

That's not what I said.

C

Chris Sacca2:02:26

But I think what... and by the way, I don't think we've probably impacted a dime of revenue from Uber. So, I'm not saying that either. I think it is still one of the most promising companies in Silicon Valley. But to say that there has not in that period of time been a shift in sentiment is bullshit and you know it.

I just don't...

I

Interviewer2:02:47

Let's talk about what matters. Let's talk about the New York part. Okay. So Travis can be very in your face combative. That's how he likes to take these on and it's been very effective. So New York City had a process and maybe Travis's style of, "Hey, let's just go do it and go renegade" doesn't necessarily work well with a process, right? And so maybe people could have been critical of Travis saying, "Hey, look, I'm going to go smashmouth these guys" and they're like, "No, no, no. We're going to do an RFP, etc." But anyone who said that, Travis just got vindicated the day they released their draft rules the other day. The draft rules coming out of New York are an absolute fuck you to anybody who's trying to innovate in the realm of transportation there whatsoever. There is no room for technological advancement. There is no room for our marketplace. There is no room for anyone to work outside of the lockdown TLC structure whatsoever. And so it doesn't send a clear message to everybody else that they should play within that system. Right. And I agree with Paul's sentiment that regulations exist for a reason and we can't have free-for-alls and we can't like the housing crisis is a perfect example of when the evisceration of regulation led to a catastrophe, right? And it's weird nobody's really gone to jail for that, etc. I absolutely believe that markets don't solve problems in a completely unregulated world, but when the regulators are not actually acting in the interest of the people, I have a real problem with that. And I know they weren't in DC. And any argument that they were in New York just became moot when they released their draft rules a couple days ago. So, I haven't talked to Travis, but he's probably got a big smile on his face, you know. That's my guess.

So, no issues, no conflict between everything you said about how the government helps and the way they run their business. I just want to make sure we're on the record and clear about this.

C

Chris Sacca2:05:00

I'm very much on the record. It turns out there's a few people here and I have a microphone.

I

Interviewer2:05:05

No, I just want to ask it explicitly.

C

Chris Sacca2:05:07

Don't tell anyone about this.

I

Interviewer2:05:10

No. Like, there's a lot of things.

C

Chris Sacca2:05:13

Fun me all you want.

I

Interviewer2:05:14

No, there's a lot of things here. Are we talking about the Randian subculture? By the way, I didn't even know that was a word, but it's awesome. The Randian... who by the way, I don't know if you know this, but she received Medicare benefits late in her life.

C

Chris Sacca2:05:31

I think that was in our story one.

I

Interviewer2:05:36

I mean, it just seems like a personal and professional conflict for you. That's why I'm asking.

C

Chris Sacca2:05:40

There's a Venn diagram and there's some overlap between that and Uber, but it's not two completely all-inclusive subjects. I think like, yeah, it's totally weird that there are some libertarian LPs in my fund and I look at their tweets sometimes and I'm like, are you fucking kidding me? It's really naive to think that if we stop charging taxes, charity will take care of it all. That we'll just redistribute the wealth charitably and we'll all look after each other. You only need to know three or four totally greedy, self-obsessed, narcissistic assholes to know that's never going to work, right? And when it comes to charity, you take off four or five zeros and people feel really magnanimous. They will not hesitate to buy a million dollar house, but when it comes to a charitable contribution, if they give you $1,000, they want a massage and a stroke and a plaque and their name all over the fucking thing. And that won't work out. We won't all just voluntarily contribute. It works one time for Radiohead's In Rainbows album and it works one time for Louis CK, right? And then it doesn't work again. I'm sorry if you're the next comedian trying to give your shit away and be like, "Oh, pay me what it's worth." You'll get zero. And so no, we can't just count on benevolence to work this shit out. It doesn't work at scale. It doesn't fucking work. And Travis is the kind of guy I love having those heated discussions with. Travis has come up to Tahoe multiple times and gotten gnarly over multiple beers and dug into these issues. I have fundamental differences with how libertarians see the world. By the way, I don't know how libertarian he really is sometimes. Travis came with me to the Obama inauguration. He was a donor. I say that only because it's public record somewhere. Sometimes I wonder if it's a character, you know, if it's a contrarian thing within the valley. We have this groupthink around being Democrats. I raised a couple million dollars for the president this time around from Democrats and it's like sitting ducks in Silicon Valley. So maybe sometimes it's just fun and challenging to think the other way. That said, I think you might actually believe some of that stuff, too. But that's not necessarily a one-for-one overlap with how Uber is run. It doesn't necessarily inform exactly how Uber works with every city that it interacts with. It doesn't dictate the brand of Uber. I think that's where that breaks down a little bit. It's just not like Travis isn't Uber all the time, just like none of FJ, Jack, or Dick are Twitter, right? They're all different flavors of it. They're all big influences on it. I don't know. I mean, if Paul thinks I'm full of shit, he should get in the crowd and ask during the Q&A. But I think if you really look at the timeline of what happened in New York the other day, I think once Travis became aware of what happened in New York, at least what I've been told, I wasn't there, but they cut off surge pricing, paid their drivers double, and stopped taking a fee. There are people including Paul who think that's disingenuous, that it was about getting those drivers to drive on the Uber network and not other places.

I

Interviewer2:09:29

Well, that's what one of their investors said tonight. I mean, let's be clear that didn't come from Paul. What Uber said... I'm just putting facts in the record because it's not really fair to throw him under the bus.

C

Chris Sacca2:09:37

No, I didn't throw Paul under the bus at all. I'm saying...

I

Interviewer2:09:39

Paul thinks they were getting drivers on the network. I just want to be totally clear for people who weren't following this because this was kind of playing out on Twitter before.

C

Chris Sacca2:09:47

I was actually trying to air the other side actually. So, what Uber said, the reason they had to pay drivers double is they would not come out and drive otherwise. What one of their investors said not a couple hours ago was we had to do this because they would drive for other networks and not for Uber. And I think I'm not nearly as extreme as Paul is on this, by the way. As most people know, I don't tell people like Paul what to write on our site. I do have a problem with the disingenuousness and the way that stories change and I have a problem with the sort of Robin Hood story of Uber. It's the disingenuousness that I think is where they lose some people and that's an example of it.

Yeah. I mean I don't know the answer to that question. I wasn't at Uber and I haven't spoken to those guys about that. I heard from one of the guys who worked there kind of what I thought the sequence of events was. But I think if you do actually just talk to your Uber driver, you realize there is something pretty beautiful about that company. Totally agree. Okay. And I think there's something about when you're starting a company, just like when you're starting a fund or when you're laid off and looking for work in Silicon Valley, throughout every other part of your life, you've had a parent, a teacher, a coach, a professor looking out for you. Somebody asking where you are when you don't show up, that kind of thing. Who's got your best interest at heart. And suddenly you go to start one of these things and there's no one actually looking out for you.

A

Audience Member2:11:30

Why did you keep struggling? Why did you keep trying and stuff like that?

C

Chris Sacca2:11:33

A parallel question is like, so what if you didn't like who's going to miss you? You know, it's like the but for like you're an entrepreneur is the proximate cause for the next achievement for their company. Without them. In that pattern of thinking and when you see kind of the lives that Uber has changed, it's probably really easy to start believing like, you know, that the company impacts the destiny of a lot of people who work for it as well as a lot of riders. And to work in that kind of environment and then walk in and have a regulator. I mean, when the San Francisco TLC started cracking down on Uber, same thing. Point to what rule Uber breaks. Couldn't fucking do it. Like they it's not electronic way building thing. They just think agreeing in those cases. And so if you grew up in that environment, like literally like agree your company up there. It's just really hard to take some of those regulations seriously, right? And like who here actually turns their fucking phone off on the airplane? Like seriously, right? It's just like when the door closes, you're still like, you know, because, you know, it doesn't fucking matter. It was a rule that was propagated by the phone companies because they didn't like all those phones attaching their towers and detaching from their towers and putting load on those towers. It has nothing to do with the communication systems of the airplane whatsoever. Right? So, you look at that and you're like, "Fuck you FCC. Fuck you FAA. This is bullshit." Like, this is not grounded in any kind of actual like protecting human life whatsoever. If it were, they would take all your fucking phones away, right? If it were really dangerous, they wouldn't trust any of us with our fucking phones, right? And so I think like with that in mind, you look at some of these regulations, you're like, it's farcical. It's fucking. They were put in place by moneyed interest to protect their business advantage. And so I understand where a guy like Travis comes from when he's working on a company like that. Like you can debate all day long tactically, should he come with love or should like should we have a peace time consiliary and a wartime consiliary etc. But the truth is Uber is trying to shake up something that has been very stayed for decades and decades and so far is doing a pretty good job of it.

I

Interviewer2:13:48

Mhm. All right, we should take some questions from the audience before we hit midnight. Um, Anie, are there microphones somewhere? Are we passing? Are they going somewhere? What are people? Jesus, it's late.

C

Chris Sacca2:14:02

I know. These people are all. They're all running for the microphone. No one's possibly leaving to beat traffic.

I

Interviewer2:14:07

Are there still more beers? Could they just distribute like another round?

C

Chris Sacca2:14:11

I know.

A

Audience Member2:14:15

Hello.

I

Interviewer2:14:16

All right. If some people have to leave, I totally understand. But please kind of keep the hub up down so we can hear questions.

A

Audience Member2:14:24

Oh, is there a microphone there?

I

Interviewer2:14:25

Yeah, there's one right there behind the camera. Hey Chris, my name's Rob SoCal. Rob on the Twitters.

C

Chris Sacca2:14:31

Oh, right on. I've seen you. Yeah.

A

Audience Member2:14:32

Yeah. We've had an exchange a couple weeks ago. You mentioned you were at the Shark Tank Studios.

C

Chris Sacca2:14:37

Yeah, I was at the Shark Tank Studio.

A

Audience Member2:14:38

And I had basically asked you, I said, you know, I should pitch something. What should I pitch? And I basically said, well, you should instead just, you know, try to join the panel because that'd bring a really interesting kind of slant to, you know, Friday night prime time. And I'm curious if they made a real...

C

Chris Sacca2:14:53

You have better things to do on Friday night than watch Shark Tank.

A

Audience Member2:14:56

Well, no. I watch the Twitter feed, so I, you know, I see it's popular. But I'm curious if they actually made an offer, would you actually look into something like that or is your schedule just too ridiculous?

C

Chris Sacca2:15:06

Uh, that's come up before. And, you know, when I went to Shark Tank, I hung out with Cuban, Mark Cuban, a little bit. And it was funny because like that day during that taping, actually, I don't think I'm supposed to talk about this fucking but maybe I will. Um, no one's still watching. No, no. Like I think I'm under NDA for like what got funded that day, but like they had a fucking guy doing like an exercise video, right? And people were offering him, you know, like 25 grand for 50% of the company. And it was just like it was so far removed from the kind of fucking we do because like the channel for a lot of this stuff to get distributed was QVC, you know, and I was just like, God, I don't really have anything to offer these guys, you know, and the investing felt opportunistic and a little bit like a game. Like you're forced to invest just instantaneously, you know, after just hearing a little bit about this company and not really getting a chance to meet these guys. And the idea was to kind of quick flip and blow this consumer product out by using, you know, your presence on the show and stuff like that. And like that's just not what I do for a living, right? I got offered a show recently that was like coach some teams that were going to conceive, build, and launch products in 72 hours, you know? And I was just like, this is a fucking family feud now. Like it's not really what we do for a living. And so I think like I've had a crisis, you know, like I think growing up I thought being on TV would be amazing. And now I just think like I would just be a clown there to amuse you and not really actually make anything better, right? So the shows that would probably improve the earth are not the shows that I'm ever going to get offered likely, nor would anyone fucking watch. So yeah.

A

Audience Member2:16:55

Yeah. Thanks.

I

Interviewer2:16:56

Okay, great.

A

Audience Member2:16:59

I think there's a line. Sorry, but we'd love for you to join the line.

So, you talked earlier about kind of your reckless success with the stock market and your success has obviously changed over the year and it's, you know, been, you know, become more matured. At what point were you able to start relying on your experience to make a good decision rather than just chalking it up to kind of luck? Like when did you know that your experience was mature?

C

Chris Sacca2:17:29

Oh, it's definitely not like I mean at no point is your experience mature. Like ask anybody, they despise themselves from, you know, their year ago self, right? They're just like, "Dude, what was I thinking?" I mean, I get off a phone call sometimes and like, "Oh, that was a poor move." Like, I'm going to walk away from here and I'm going to be like, "I can't believe I said some of that fucking out loud." And I'm sure I offended somebody and like, "Oh, I better go preemptively apologize or something like that." Like you never do. And if you start thinking that like now you've got it figured out and now you're mature, like you're both wrong and an asshole. And so you don't, and I still do things recklessly now I think and maybe the stakes have changed a little bit and I'm married and I have a child and, you know, I like one of my heroes is Elon Musk who has taken twice, he has bet every dollar he had and kept like no safety net whatsoever. Right? It's worked out really well for him in the end, but that's incredibly fucking reckless, right? And yet, you could also paint him as a mature, wise, amazing leader who's, you know, put people on the moon and built an awesome car. As well as a bunch of other fucking too. But no, it never is. It's never mature. It's just your best try that day, you know, and hopefully you can build in a mechanism for reflection, a mechanism you can hopefully surround yourself, unlike all the buddies that I had keep telling me that I was like a genius. You know, my wife will hear me on a call at home 'cause I work from home and then I'll get off and she'll be like, "Jesus, you fucked that up." I'll be like, "What?" And she'd be like, "Why would you have said that to that guy? Like he's going to..." I'm like, "Oh, come on." Yeah. No, but she's particularly good at this fucking too. And I just like don't surround yourself with yes men and people who are just going to constantly like you. There's a friend of mine who's an author named AJ Jacobs. He's amazing. He wrote like The Year of Living Biblically where he lived literally to the letter of the Bible for an entire calendar year. His beard was like out to here and he only wore natural fibers and shit like that. No shrimp and you know. But he did an experiment where he said yes to everything his wife asked him to do for 30 days and she thought it was cool for like six or seven days and then she was worried like their marriage was going to fall apart because there was no like push and pull yet, right? And so I think the most important thing is to like keep going for it but surround yourself with people who can call bullshit on you a little bit. I think the most dangerous aspects of my life, I had either not surrounded myself with people like that or chose to not listen to them at all. And I think that's when you can get really fucked up. Like I have this principle called bold humility, which is like be bold. Like don't apologize for being awesome. Like all these business advice books that say humility, humility, humility, like 100% humility is not a natural instinctive human trait. Like each of us in this room is totally awesome at something, right? And it may be something that the world generally values or it may just be something generally worthless, but we all have some awesomeness in us. And I don't think you should have to apologize for being awesome at something. Like when I hire a coder for one of my companies, I don't want them to have to pretend like, "Oh, I kind of suck." I want them to admit like, "No, I'm the fucking best at something." But where we get into trouble is when we forget the other half, the humility half. Like anyone here who's ever been a boss, think of the very first time you were a boss and a question came up you didn't know the answer to, but you're like, "Well, I'm the boss and so I can't let everyone else here know I don't know the answer to this question, so I have to pretend." Right? And you say something stupid, you make something up, you cover for the fact, you have no idea. And like the people around you can sense that and they move away from you. The first time like that you're a boss and you don't know the answer and you say, "Hey everyone, what should we do? Who has opinions on this?" Suddenly you're empowered. You've collected all that wisdom around you and everyone around you feels that much more awesome like they've contributed to you that much more. And you build this strong team even from people who might not even report to you or like you. That's like the dynamic of actual power is asking people to contribute and listening to their response. I mean I've been lucky enough to spend time with the president and that's how the president operates. Like he talks to the honchos and then he actually asks the people behind them who are carrying their bag and keeping their calendar, "What would you do?" And like in doing so, he's empowered everybody in that room. He's bought a real excitement and a loyalty and an eagerness to contribute from everybody there. And it's also just informed a much broader set of perspectives for him and helps him to make a better decision. And so I think like it's not at some tipping point suddenly you're a genius and you've got it all figured out. It's a process by like do your best, take chances, surround yourself with a feedback loop and don't hesitate to admit when you need help with that.

A

Audience Member2:22:34

Okay, thanks. I think you answered the question I was really trying to ask.

C

Chris Sacca2:22:38

All right, cool.

A

Audience Member2:22:42

Hi, Chris. My name is Ethan. Thanks for having this talk. You talked about the carriers and kind of respecting their craftiness, but I was actually just talking with some people in my office today and the fact that data plan like the price for bandwidth going up and $90 data plans to me it's just collusion and I was wondering like what you thought about that industry and the one company I kind of see trying to disrupt it is Freedom Pop lately, but I was wondering if you're working with or looking for any companies or doing anything in that space of really trying to fix the data plan issue in wireless.

C

Chris Sacca2:23:13

Yeah, I'm not working in data in wireless anymore. It's funny enough, I would say it's too regulated and like it just requires too much overhead for a VC to get into a space like that. Like I need to have lawyers and lobbyists and public interest groups and I just don't have a staff. It's me and one other person. And so, there is a reality we're running out of spectrum. Like we're just running out. Like every time you use your phone to watch YouTube, it sucks up a certain amount of wireless spectrum and with more phones running more YouTube etc. there's just not enough left. And unlike fiber, which uses light, which multiplexes at a rate that keeps constant with Moore's law, so it's geometric, extracting performance out of the wireless spectrum is linear. Like Shannon's law is a step function, and it's linear. And so we're using geometrically more, but we're only increasing the efficiency like this. And so it literally is an invisible finite resource unless we manage it differently. And right now it's warehoused by carriers who don't use it very much. Its equipment's run on it that doesn't work very well. Like my team at Google spearheaded a bunch of the 700 megahertz and white TV whites spaces initiatives to free up some of that stuff in between the TV channels. And after I left they were really successful at making that work and bringing more spectrum online for experimentation. But I think the pricing is decoupled from that reality right now. Like what you pay for SMS is just utter utter bullshit in terms of what it actually costs them to deliver that. But let's be clear, we're just running out of it. And so unless we figure something out quickly with cell splitting or a different way of open spectrum management, I think frankly we're going to have a problem where there's going to be a digital divide where rich people get access to spectrum and poor people don't.

A

Audience Member2:25:09

Thanks. Real quick, was Design LLC one of your shell companies?

C

Chris Sacca2:25:12

Yeah, Design LLC was definitely one of my shells. Yeah, Larry Page taught me how to start shell companies that were Google-proof. And so if you think about Design LLC, like the word design occurs before the word LLC or the abbreviation LLC so many times on Google that if you were looking for my thing called Design LLC, it would get lost among all the thousands and thousands of companies that are called something Design LLC. And so that's why I use it as a shell.

A

Audience Member2:25:39

Hi, my name is Janette. I was curious, obviously you're constantly speaking to young entrepreneurs and young companies and companies that are getting their initial boards and you spoke about Marissa Mayer earlier. Just in general, there's been a lot of discussion about whether or not having women executives at technology companies and things like that. And again, obviously with the current trend, there's been a lot of that discussion. Do you think there's actually a legitimate value about a different kind of way of looking at things that truly it takes a person of a different gender to see or do you think that it's maybe kind of dangerous because there's forced gender discrimination sort of almost?

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Chris Sacca2:26:27

Yeah, I mean it's hard for me to wrap my head around the arguments that women bring a certain something different than men do to a company because I just think that's boxing people in, right? And you're like, raising a daughter, like it's funny how when your daughter's born, everyone gives you pink shit, you know, and you're like, turns out she's capable wearing blue shit too. I checked. It works. So, but I mean, think of like all the men executives, you know, and the different styles of management they have, right? I mean, think of all the male entrepreneurs you know, all the male investors, you know, just think of the guys in your neighborhood. Like, they all have very, very different styles and traits and characteristics. And to box them in and say that like one of those is manly is a little broken. That said, like, you know, I think Marissa has individual character traits and business traits that are like just specific to her. And I don't know if they correlate to her being a woman or just her being awesome, but you know, like if you look at a company like Google and you look at Shona Brown and Cheryl Sandberg who's now at Facebook and Susan Wojcicki and Megan Smith and like, I'm going to leave somebody out and be in real trouble, I'm sure, but there's just like this powerful cadre of women who have very different ways of doing business. Some of those women I mentioned are straight. Some are gay. Some dress in hot couture and don't apologize for it. Some dress in like jeans with sleeves rolled up. Like some I would come cry to. Some would probably punch me in the nose and tell me to buck up if I were crying. Like I mean to group them all together, I don't know. So I think there's amazing female like Padmasree Warrior who is the CTO at Cisco, makes no apology for the fact that she's an amazing artist, dancer, cook, she knits, you know, and she's also just a badass executive of a Fortune 500 company. But I don't know if she has any natural advantage or disadvantage in terms of her skill set. I do think like women are dealt a really shitty hand in terms of getting into these companies and surviving those companies and I think that's the result of the stereotyping that happens and I think that's the result of preconceived notions and so I don't like to reinforce them with saying like hey a woman in this room would somehow make it work differently because that's precaging some outcome that puts you in a box and I think that's the opposite direction of where we should be going. Right. So I'm sorry, I got asked, yeah, I have like I got asked do I invest in companies that have women CEOs or whatever. Yeah. So one of my best investments in my portfolio is a company called StyleSeat. And it's run by Melody McCloskey who is an amazing entrepreneur who is very easy to underestimate 'cause she's young and beautiful and you're just like well you can't be an entrepreneur, your hair looks too nice. But it was funny. I invested in that company because I knew Melody and I knew she was capable of like shipping good product and I put in a little bit of money and I was just like I don't know anything about this market. So she built a booking engine and calendaring and payment engine for salon stylists, health prof like estheticians and stuff like that. And I came home and told my wife about it. I was like, "Look, I back Melody because I think she's just great, but I don't know anything about this business really." And my wife was like, "Do you know how much women pay to get their haircut?" I was like, "Do I look like I know? I go to Supercuts." Like, no, I don't know. And she's like, "Yeah, it's a couple hundred bucks. Like, you know, people in the big cities." And she's like, "No offense, by the way." She's like, "Do you also know there aren't that many people our age who are actually blonde?" And I was like, "No, really?" And she started naming all these people we know. She's like, "She's not blonde. She's not blonde. She's not blonde. That's like a $300 a quarter treatment." I was like, "Oh, no shit." Like really. And so like suddenly I started to realize this was like a huge market. And what was funny was Melody had been going up and down Sand Hill Road talking to a bunch of stiff white guys about this business and no one was taking her seriously because she's young, because she's a woman, because she hadn't started anything before, and because she's dealing with a problem they didn't know how to solve. The other aspect to it is like a big chunk of her business is the African-American hair market. So braids and weaves are expensive and it's a big part of the disposable income of a lot of those communities and like who on Sand Hill Road would possibly fucking know that, right? And so Melody's out there crushing it with this business that has close to a hundred million in annual bookings going through it right now and people will continue to underestimate her because they don't understand the market or because she's a woman though.

A

Audience Member2:31:22

No, I didn't have any trouble raising money. I know I'm not young and beautiful, but I am a woman.

C

Chris Sacca2:31:26

I think it's both. You had much more reputation. So, you'd already proven yourself like you were already a reporter and...

A

Audience Member2:31:32

Not as an entrepreneur.

C

Chris Sacca2:31:34

Yeah. You were a well-known brand and you went to raise money from people who you were a known entity with, right? So, Melody just wasn't, right? She was a producer at Current, you know, and like a digital product manager, etc. So, I think, look, for every story about how like there are women who make it, like I think there are more about women who don't get a shot or who don't give themselves a shot. And so like yeah, I have I mean I didn't invest in Melody because she's a woman, but I think she's going to make me more money than all but, you know, I think she might be the third or fourth most valuable company I've ever invested in.

A

Audience Member2:32:11

Wow.

I

Interviewer2:32:12

All right. As much as that was a great answer, please don't answer ask questions from the audience. It's really disrespectful to people standing in line. We barely have time to get through them.

A

Audience Member2:32:21

Hi Chris, I'm Joe Winky. So there's a lot of unemployed people out there and the numbers are higher than the stats and technology has disrupted a lot of that. But you talked about the Google car and there's like two million truck drivers and then all the cab drivers and the FedEx guys and the UPS guys and there's 3D printers coming online and there's just like a lot of stuff that is coming real fast and the entrepreneurs here are good but they just don't seem to be keeping pace with this. I don't think there's going to be enough jobs and you work with a lot of entrepreneurs. Have you thought about this and how society might like start preparing for like a lot of unemployed people?

C

Chris Sacca2:32:59

Yeah, I mean I would like to think that you know the president asked me and guys like Shervin Pishevar etc to gather technology leaders to meet with him and do like open Q&A behind closed doors. And you know, one of the things he kind of heard a lot was the same thing he heard from Steve Jobs. It's just like a lot of these jobs aren't ever coming back. But the parallel to that is a lot of these jobs we don't necessarily want to come back and like the harsh reality is we have to get our heads like we have to be ahead of that curve rather than behind it, right? So it's very easy like when you to kind of tie into the libertarian part, you know, it's really easy to see everything we do in Silicon Valley as an exercise in efficiency. Like I'm sure that most of the people in this room have an Amazon Prime membership, you know, and like it's just so easy to just one click and buy your shit right? And like skip your local merchant and buy that stuff. And like I use it so much I have like a cardboard problem, you know? And the result is like you know local merchants are going out of business like you can't buy shit locally. The stores aren't...

A

Audience Member2:34:22

Do same day delivery soon and that'll decimate retail.

C

Chris Sacca2:34:25

It wipes out a lot of people, right? And so it's very easy as an entrepreneur to see that as a benefit because I just saved you a bunch of money. Like I gave you a greater selection and saved you a bunch of money and like made it possible to access. I mean, my wife needed like fake blood for her Sharkbite victim costume last night, you know, and like I Amazon Primed the fuck out of that. I didn't walk into a costume store like, and I've got like it was an add-on product, so they made me buy like 20 of them to get a ship, but I've got like 20 vials of zombie blood if anyone needs it. Like, but that was money that came out of the mouth of a local merchant, but it was super easy for me to be in another town and order it. It just showed up at my house, right? So consumer benefit but with an externality that wipes out somebody's job and we get the luxury of not having to ever take that into account when we build stuff, right? So...

A

Audience Member2:35:14

Revolution, right?

I

Interviewer2:35:15

Let him answer the question.

C

Chris Sacca2:35:16

Well, no, I mean we're on the same page here. What I'm pointing out is again what I think is a short-sightedness of the libertarian let the market decide all this shit kind of point of view because the harsh reality is that when I rode my bike across the country in 2009 and I went right across the middle of the country like paralleling old Interstate 40 basically and old Route 66, a lot of those towns have gone away like they're not smaller or depressed, they're gone. Like there was a town in Oklahoma where the facade of one of the buildings had collapsed into the street and they just put up two cones as to say like don't drive over the bricks. Like it didn't even get shuffled into the gutter. Like you go to these towns and like the hardware store is closed. The place where you get your haircut is closed. Like the dress retailer downtown closed. Like all these places are closed, replaced by the big box store like a Walmart and a Family Dollar and a Dollar General. And you ask the kids like, "Where do you hang out?" And they're like, "Walmart?" And I'm like, "No, no, no. Like, where do you hang out to like get close to your friends and shit like that?" And they're like, "Walmart?" And you walk through the Walmart and you see that the people there who are working for hourly wage used to be the small business owners who have been decimated by that. And you start to ask yourself, okay, this has been an amazing exercise in efficiency. And like Walmart has everyday low, low prices, but like what is it if we don't have security in our jobs? Like what is it if there are no careers left anymore? You know, I grew up in a town that was the primary employer was General Motors and they made radiators and air conditioners for GM cars. Like almost everyone I knew whose parents were in the union. Almost everyone I knew grew up in a house that they didn't have to worry about making payments on because they had a nice union job and they didn't have a second home, but they had enough money to take their family on vacation and, you know, maybe they had a hunting cabin, you know, in a canoe or something like that. Like, and they could afford to send their kids to state school. Like, there was something awesome about growing up in that time where all my friends' parents were actually middle class but had some job security as long as they showed up and did their job. Like we don't fucking have that anymore in this country. Like that scares the fuck out of me. And so, you know, to not make it overtly political, like I worry like we've been letting a market try and take care of this and it's not working. Like we have a very concrete education divide. We have a very concrete housing divide. We have a very concrete nutrition divide. We have a very concrete digital divide. Like we've divided into these two countries where we have a bunch of people who have no stake in their future. They work on an hourly wage, no benefits. If anything befalls them are completely fucked. And then the rest of us who own everything and when you're building technology companies and you're living in Silicon Valley and you've got a startup and you just point at a problem and you make it better, it's easy to never have to think about any of those extra externalities at all. And so I worry about that. I don't know what the answer is. Like is Walmart a good thing or a bad thing? Like it's a good thing if you're living paycheck to paycheck. And if you ask the people who have been displaced by Walmart, they'll be the first people to tell you Walmart's great because it has everything I need and it's everyday low prices, right? And yet it's funny. It's this really weird like, you know, sapu.

A

Audience Member2:38:34

So, I mean, I guess this is the same thing I was trying to get at with Uber. You think about those things. Does it change your investing habits? Does it change your...

C

Chris Sacca2:38:43

I think Uber for now the people that Uber displaces are the fleet managers because I think Uber inspires a whole generation of individual business people who are like using Uber to finance a car to run their own business...

A

Audience Member2:38:57

In general this movement towards efficiency, I mean let's face it if Uber makes a better transportation model that's great for people who can afford Uber. I mean I think it fits into what you just said. I mean, in general, do you worry about displacement for people who could...

C

Chris Sacca2:39:12

I think if Uber succeeds, fewer cars get made? That's I don't think it displaces like I mean, it creates jobs for drivers and it destroys more jobs for car manufacturers. Like...

A

Audience Member2:39:20

But I name a company of mine that doesn't do that. Name a company that is predicated on efficiency.

C

Chris Sacca2:39:27

Yeah. No, that's my whole fucking point is that like...

A

Audience Member2:39:30

And my point is you just went on this beautiful soliloquy about the impact of it. My point is, does that impact how you make investing decisions? Does it impact how you make consumer decisions or do you just worry about it?

C

Chris Sacca2:39:44

I mean, consumer decisions, absolutely. Investing decisions, I mean, I didn't invest in E la Cart because I think it just makes people fat, right? And like I respect the team that builds that. They're having a lot of success, but I think like making it so easy to order extra shit at Applebees that all you have to do is pick up the device on your table and push more buttons and you get more fucking onion rings like is probably not something that's improving the health of the planet. And it's my bad. I would have made a lot of money and maybe I let down all my investors by not doing that. But, I do see a company like Uber making it safer for people to travel. Making, you know, improving the productivity of their time. Like, so it's a balancing act. Most of these companies.

A

Audience Member2:40:25

Yeah, of course. Balancing act.

C

Chris Sacca2:40:27

Like I don't invest in guns, tobacco, porn, you know, but with some of these companies like StyleSeat absolutely empowers a generation of mostly women stylists to manage their own destiny and not be beholden to a salon anymore. Like no doubt about it. I feel good about that investment. But you know, because it's building efficiency into the spectrum, probably there's going to be fewer stylists total. You know, like I don't know.

A

Audience Member2:40:53

Mhm. All right. Hey Chris. So, you mentioned a handful of industries that you have like a lot of experience with and invested in like you know wireless you know with Google and the taxi commission at Uber that are overregulated. I wondered if you could shed some light on some industries that you have a lot of experience with or invested in right now probably you know or other than finance that could use a lot more regulation from the government.

C

Chris Sacca2:41:18

More regulation from the government. This is funny. We're doing a renovation on our house right now and I've been waiting 4 months for the permitting. But I don't know. I do worry about finance. I worry. It's funny. So...

A

Audience Member2:41:34

Other than finance.

C

Chris Sacca2:41:35

Yeah. But I was going to say like I know you said other than, but I'm going to bring it back in. Here's the weird thing. Like if you actually want to key in on one part of this is that for me to start letting things like this or the externalities move into my investing decisions starts becoming eerily paternalistic, right? And like at the heart of regulation often is like in the consumer protection type stuff is saying there's a group of people who don't know better and I need to look out for them, right? And like I deeply believe that's true. I deeply believe that's true. But it's also a little bit fucked up to say like I need to step in and make decisions for these people who aren't capable of making decisions for themselves, right? Like that's weird, right? And so there is something kind of eerily unsettling about saying like I know better than you like because I borrowed a bunch of money to go to school and I got a big education and so let me make this decision for you, right? And so I don't, you know, I don't know, like most of it for me comes down to regulation around people who are making decisions with low information, right? Like just I mean, I've now had the opportunity to witness focus groups for the election. So there's this really funny thing that happens in focus groups, nonpartisan focus groups where you know it's Obama people go and ask the questions but they don't tell them they're Democrat or Republican. And they'll ask people like so you'll ask people about big government. People like oh boo big government you know and they're like you know what do you think about taxes? Oh boo you know like what do you think about Medicare? Medicare is cool man. Yeah. Like really Medicare? Yeah. You like Medicare? Yeah. Medicare works out. Like is Medicare a government program? No. Let me be clear. Medicare not a government program? No, no, no, no. How do you know it's not a government program? And they'll pull out their pay stub and they'll say, "You see here, this is my federal taxes that goes to the government. These are my state taxes that goes to the government. This is Medicare that just I pay that into this business called Medicare. And this is Social Security and I pay into that, too." Like, we have a shitload of Americans who believe that's the case, right? And so should those people be allowed to sign mortgage applications, you know, like do those people process the full implications of a compounding interest on an APR or anything like that? Like do they know what points are and stuff? Like I don't know. It's pretty delusional to say they don't. And yet the empirical data from the last round of the economy are they fucking don't, right? And so like I think you excluded the one sector where I think when it comes down to consumer decisions like I worry about consumers trading the short-term for the long term every time. Like paternalistically if anyone here did a startup that used lottery economics to incent behavior I'm all over that shit. Jay Walker, the guy who started Priceline, realized there was a problem that old people weren't taking their medicine when they were supposed to take their medicine, right? And they're like splitting pills and taking too long. So, I'm told he built a medicine bottle that if opened at the right time would enter you to win a lottery. So, guess what happens? Old people start taking their medicine at exactly the right time. Like you put a little bit of self-interest in there and you get the right outcome. Because it turns out humans are horrible at calculating the expected value of a lottery. Like entire city exists in the desert because of that, right? And so like it's really paternalistic, but I'm like, "Hey, let's just use lotteries to incentivize behavior. If you're not smart enough to gather all the information about what would be good, healthy eating decisions, then fuck it. I will incent you with prizes to eat better because I know in the long run I'm going to save money from the healthcare budget, right?" And so it's like anything involving consumer decisions is the area where I'm most concerned. And also like I feel so fucking elitist that I think like somehow I have a better answer than anybody else. You know...

A

Audience Member2:45:49

That I mean is that enough of an internal quandary for you?

I

Interviewer2:45:54

Exposed a lot of these. All right we got to move on. Sorry. It's like this is a marathon Panda Monthly at this point and I want to get these last three questions.

A

Audience Member2:46:02

Hey Chris. Thanks for coming down here. I really appreciate it. It's been awesome seeing you and talking and hearing from you. I guess the question I wanted to ask is with all the focus on the VC world and the entrepreneurs and as you said you know there's a big focus and people think they're really super cool and awesome and you know many of them are. I guess if there are folks out there who actually don't have enough money to be VCs or angels or whatever and can't actually be part of the startup ecosystem for whatever reason right let's say legal or whatever, what are some of the things you would kind of suggest that they could do to actually be part of it? Like do you think there's still room for the kind of stuff you were saying actually just like cold calling people and saying, "Hey, I want to help. What can I do?"

C

Chris Sacca2:46:42

I think there's more room for that than there was before, right? Because like a friend of mine just called up to ask about being an angel investor and I was just like, "Turns out better time than ever because stuff like AngelList exists. Like there's dozens and dozens of incubators and accelerators. There's people everywhere looking for help of any kind." Like one of my mottos is create value before you ask for value back. And I think there's never been an easier time for you to just walk in and be helpful. If you, you know, if you have enough money to kind of put food on the plate and not have to worry about making a paycheck immediately or you can do it in addition to your job, like I think it's never been easier to do that. And so, I heartily encourage that. I think just showing up and being helpful, it's never going to get you in any trouble. And frankly, you might end up with a big piece of the company and not have to have paid for it.

A

Audience Member2:47:36

Okay, great. Thank you.

Hey Chris, Ryan Arch Deacon Orware, what excites you about the future and where would you like to place your money? What markets that you haven't already gotten into yet?

C

Chris Sacca2:47:51

I mean, there's no, I put my money where my thoughts and vision are all the time. So, I don't think there's any market I haven't gotten into yet. Where I invest is places I can be helpful. So I don't do biotech for instance like 'cause I wouldn't know how to be helpful to somebody like. But so I try and invest in problems that I know I can have some modicum of impact on solving. And, you know, what excites me about the future is probably like I would encourage anyone to read Buckminster Fuller stuff because I think he was the one serious author who believed that technology would solve our museum problems rather than like accelerate them, you know, and accelerate us into a nanotech disaster, you know. I think like he was, I think he better represents my optimism than I could on stage. So, okay, great. Last question.

A

Audience Member2:48:50

Hi, Chris. My name is Josh. Hey, my question is what if you could boil it down to simple terms, what drives you? What wakes you up in the morning? And is it to create? Is it to win? And how have you seen this change with your level of success?

C

Chris Sacca2:49:12

Yeah. So, I didn't grow up with any money and in the beginning I was definitely driven by money. I used to gather up all the walnuts in my yard. If anyone's ever had a walnut tree that the walnuts come up, they're covered in a really pungent skin. Like they smell, right? But I used to poke holes in them, tie string on them, and then I took my little brother, I put a sandwich board on them, and I would go door to door with our wagon selling air fresheners. Until somebody in the neighborhood would call my mom and she'd be like, "Oh my god, where'd they go?" And so I have just always wanted to make money. Then you make some and it's really easy for you to sit up on a stage and say like, "Ah, money is not everything, right?" because so many of you are underwater paying back student loans trying to make ends meet right now and you're like fuck you. Like money would be really nice. But it's true. You make a little bit and you're just like you know I'm not going to say mo' money problems but life gets complicated and shit arises and so you have to find something deeper and more meaningful than that. Like I always thought once I made X dollars I'd be out. But I'm not. And I don't think it's about ego and I don't think it's about rep. And I've been laying low and not even talking publicly for a long time now until just the last month really. I think it's about just like I can't not help fix a problem if I see it. And if you talk to my mom and dad, they'll tell you that's been the most consistent trait since I was young. Like the money thing was probably like more conscious, but subconsciously like I can't avoid helping fix a problem. So every time I think I'm like, "Okay, enough of this startup shit. These people betray me. It's horrible. It takes time out of my day. I'd rather spend that time with my daughter who's amazing." Like instead I'm like, "Oh, that's a pretty cool idea that could solve a real problem. Like maybe I should, let me tell my wife, 'Let me just do this one call with these guys.'" You know, I'll come out of the room be like, "Oh yeah, I'm in. I'm in." It just you can't help it. And I think if you really get down to like what drives a lot of entrepreneurs, people who are starting their businesses, investors, product, they just are addicted to solving problems. They can't help it. They see something wrong, they want to debate it, complain about it, and fix it. And I think that's what drives me. And I think that's the thing that transcends money and stage in life is that there are people who just want to fix shit. And I'm sure a lot of you feel that way, too.

I

Interviewer2:51:45

All right. Great. Thank you. We are almost at the end.

C

Chris Sacca2:51:50

All right.

I

Interviewer2:51:54

There will be more time for applause. There are two questions we ask at the end of every Panda Monthly.

C

Chris Sacca2:52:00

I'm sweating. So excited.

I

Interviewer2:52:01

We're going for quick answers here. Before we get to those two, I have one for you. I can't believe no one asked in the Q&A. Yes or no? Are you as disappointed with Obama as most of the people who voted for him?

C

Chris Sacca2:52:13

You kidding me? So, what's wrong? Like, our stock market is more valuable than it was when he came into office. We've created 5 million jobs. We ended a war in Iraq. I'm curious what the disappointment is. Like frankly I admire the guy for getting as much done as he has in the face of people whose sole purpose in life is to defeat him at the expense of our country. Like I think the entire notion of patriotism has been shat upon by half of this country. When Governor Christie goes out and reaches across the aisle to try and get some shit done, like watch the tweets that people sent him last night calling him a traitor and a fat Muslim sympathizer. Like how fucked is that? Right? So guy goes out of his way to be helpful but we've got a president who just made it so that everyone in this room will be guaranteed access to medical coverage despite a pre-existing condition. I have a pre-existing condition. My wife has a pre-existing condition. Everybody in this fucking room I'm sure has one if you end up not fitting the actuarial tables of being an ideal client. And so it takes a lot of fucking balls to push something like that through when you don't necessarily have all the political capital you'd want and a party in your face trying to oppose everything you do. So that's why I've ruthlessly fought for him to get back into office, why I've raised a lot of money. That's why I've volunteered taking people to Chicago and I think we're going to win and I hope everyone in this room makes sure that everyone they know in Ohio shows up to vote.

I

Interviewer2:53:38

All right. Okay. What is the one thing you believe that no one else or very few people believe?

C

Chris Sacca2:53:46

Oh, I forgot I was supposed to say this. I forgot I was supposed to study for this exam. I know you asked this at the end. I don't know. I probably said it already. It's really late. You said a lot.

I

Interviewer2:53:54

Yeah, it's really late and I know people want to go. So, I think I'll just say ibid to whatever I said before.

C

Chris Sacca2:54:01

That's so lame. Okay, this one you are not punting on. I love when at the end of your montage it'll be Sacca saying, "Oh, I don't know." This one I'm not letting you punt on. If you could pick one mediocre superpower to have in the world, what would it be?

I

Interviewer2:54:16

Oh, I forgot about that question, too.

C

Chris Sacca2:54:18

You should remind your guests that they have to answer these questions.

I

Interviewer2:54:20

It's better when it's off the cuff.

C

Chris Sacca2:54:22

Mediocre superpower.

I

Interviewer2:54:23

Yeah. Do you want... What did Elon say?

C

Chris Sacca2:54:27

Elon said to not get stuck in traffic.

I

Interviewer2:54:30

That's plenty, right? I mean, that's lame.

C

Chris Sacca2:54:32

Well, no, it was to sort of magically be able to beam when he's late in traffic or something like that. I mean, it's a superpower that's...

I

Interviewer2:54:37

I want to function on full power with two to three hours of sleep. That's what I want.

C

Chris Sacca2:54:44

I say this as a father of a one-year-old who gets going at like 5:30, ready to fucking go. I'm right there with you.

I

Interviewer2:54:50

Yeah, that's my superpower.

C

Chris Sacca2:54:52

All right, does that count?

I

Interviewer2:54:53

That counts.

C

Chris Sacca2:54:53

Okay, thank you everybody. I really appreciate it. Good luck, everyone.

Chris Sacca, Lowercase Capital

About Chris Sacca