This Principle Guided Me to SUCCESS in Life! | Chris Sacca | Top 10 Rules

There are all these business books that say like, hey, be humble, be humble, be humble. But humility is not a natural state for a kick-ass human being.

I was writing terms and conditions for websites, some of which turned out to be adult websites, but they paid cash.

And Travis Kalanick, while being CEO of Uber, was ranked number 2 in the world at Wii Tennis. Who here wants to compete with a guy like that? Some of you aren't founders and you should fucking admit that to yourselves.

He's a former lawyer, venture capital investor, company advisor, and entrepreneur. He's the proprietor of Lowercase Capital, a venture capital fund in the United States. He invested in seed and early-stage companies like Twitter, Uber, Instagram, and Kickstarter. He's Chris Sacca, and here's my take on his top 10 rules of success. Rule number 5 is my personal favorite. I make sure to stick around all the way to the end for some special bonus clips. And as always, as Chris is talking, if he says something that really resonates with you, please leave in the comments below and put quotes around it so other people can be inspired as well. Enjoy.

Too many investors invest in the things that they just like and are comfortable with and are within their own little bubble. And yet I think the distinction we like to make is invest in things that we know we can personally impact the outcome of.

So I—

everyone could be talking about the hot biotech deal and it might be on the verge of of curing cancer, but I cannot do anything to advance the mission of a biotech company, quite literally. And so we pass. As cool as it may seem, if I'm gonna mooch, I may as well mooch in the public markets, right? And just throw darts and ride the greens and reds. So if I believe that I can take something that's already a good company and just make it a little more likely to be a success, then that's a rigged game for me. It almost feels unfair, right? And I can just be that much more confident that The investors who give me their money, I'm gonna give them their money back and a lot more after that. I'm a big believer in the liberal arts education. I think it's overrated— or it's underrated, I mean, in that the computer science stuff is overrated. It's great, technical skills are amazing, but what has happened, as I referred to earlier, is we've just— all the storytellers are kind of gone, and the actual understanding of our users is gone. We've lost all that sensitivity, and yet I feel like that sensitivity comes first from really knowing yourself. So I encourage people to take classes classes, not just in art and music, but in death and dying and philosophy and theology, these things that you'll never make money on directly, but I think one of the most important things you can do is be interesting. Like, I only really want to work with people who've not only had those crappy jobs I talked about, but are also interesting. They have stories, there's some meat to them, there's some flesh, there's something really compelling. That's who you want to be with if you're going to spend night and day building something together. That's who you want to travel with, these people with these perspectives and these stories, and so, And interestingness is not something that I think you're born with. I think it's achieved by vulnerability, by adventure, by all these things. And so I really emphasize interestingness. I think you can get it from studying, from reading, from putting yourself in uncomfortable positions. Maybe more Americans should just hang out naked in saunas. That could make them more interesting. But traveling abroad, going to Ethiopia and helping dig wells, that kind of stuff I think builds a much more impressive character. So Stuart Butterfield, who runs Slack, obviously one of the most successful investments in our portfolio, an amazing company. Stewart is a liberal arts major. That dude is fucking fascinating. Like, hanging out with that guy and talking about anything beyond Slack is amazing. He's Canadian, and he's got great insights into US politics. But you just follow his snaps on Snapchat. The guy is— he eats well, he's checking out art, he knows music really well. He's a really interesting guy. So he becomes a magnet for talent. You want to be around Stewart.

He enriches your soul.

And if you look at the team of people he's recruited, superstars like April Underwood, for instance, like, he's really recruited an incredibly deep bench of people because they want to have authentic and multi-dimensional relationships with him. And I think it comes through in the product too.

It's time for step 3. Step 3 is to go on offense. Now, what do I mean by going on offense? Well, you guys all know sports. This is the Big Ten. You can't avoid sports here. You know what it means to be on offense? Offense is calling plays. Managing the clock, keeping the other team on defense, reacting to you. Now take that term and apply it to the rest of your life.

Let's take, for example, email.

Is your email inbox offense? Is that playing offense? No, no, no. Inbox stuff is just defense the whole way. Imagine if you took your to-do list and you posted it on the door of your dorm room with a little pencil there and invited the entire world to come and add anything they wanted to your to-do list. Well, that's what your inbox is. It's a publicly posted to-do list where it's up to everybody else to impose their whim on you. And even worse, what happens is we get up and it's the very first thing we check. And so we get in there and we start doing stuff for all these other people, and yet along the way we've forgotten what we wanted to accomplish for ourselves. We haven't done the things that we know are important for us and for our goals. And so that stops now. It's time to close your email, and write out your to-do list. I don't just mean your to-do list for work, I mean the big to-do list for your life. What do you want to get done? It's an awesome time in history to be authoring our own futures in real time.

I mean, the internet makes it possible to be just one degree away from anyone in the world.

Any one of you right now can send me a reply on Twitter, if you had your phones out, and I'm that accessible. Any one of you right now could use the internet to become an expert in any subject at all. In 2007, back when I was at Google, I went from not knowing anything whatsoever about the wireless industry to leading a group that led a $4.7 billion project that turned Verizon, AT&T on their heads, sent the FCC spinning, and changed the landscape of wireless forever, paving the way for the apps we all have on our phones today. Never in history have there been fewer barriers in the way. No matter where we come from, what our parents did for a living, how much money we have, we all can be unqualified successes. So who do you want to talk to? Where do you want to spend your time? What do you want to learn? You just spent 4 years, maybe 5 or 6, but we'll just forget that. 4 years for the most part taking the classes you were required to take. So now it's your turn to go on offense. What are you curious about? Where do you want to travel? What adventures do you want to go on? Which fears of yours do you want to tackle? You know, offense also means owning your personal brand. Your voice should be the first 2 or 3 responses when I search for your name on Twitter. I'm sorry, on Google. But how do I— how do you get there? You tweet, you post, you blog, you comment, you engage in discussions. You own your own identity. The tools are there to have a public identity and to go on the record proudly so and stand for who you really are. I mean, think of it.

I hire a lot of people for a lot of jobs.

Imagine, why would I ever hire somebody just on the basis of a resume when instead I can search for them online and get years and years worth of insight into who they really are and how they think and how their ideas evolve and how they react to the changing world we're in. Those tools exist for you to create your own authentic brand completely within your control, and do it. I mean, sitting back and watching television, that's playing defense. But going outside and being with your friends, that's offense.

Provoke, inspire.

Don't just get involved, but inspire others to be involved. That's playing offense.

In the spring of 2000, I was way overleveraged into these two stocks. In a matter of a few days, I found myself going from $12 million to the good to $4 million to the bad. So I was 25 years old, I owed $4 million, I didn't have anything to show for it. I didn't have a house or a boat or a plane or anything I could sell to pay it off. I just owed it. I came from a middle-class background. Neither of my parents had ever made more than $100,000 in a year, and I was just stuck. And I had to make some choices then about whether I was gonna quit and, you know, or try to declare bankruptcy, or whether I'd try and fight it out. And it happened just as I was graduating law school, actually. And so I said, well, I'm gonna try and fight this out, and I'll take a sellout job as a as a corporate lawyer out at Fenwick West, and I'll try and grind this out. And so during the day I would do corporate law stuff at a tech firm, and at night I would do pretty much anything that somebody would pay me to do short of giving blood or massages.

So—

Did you use like Craigslist for this?

I did go on Craigslist. I was writing contracts and business plans and renaming companies. There's a thing called Elance out there. There's now like oDesk and RentACoder and stuff, but E-Lance was the first of those markets, and I was the first lawyer on E-Lance. And so I was writing terms and conditions for websites, some of which turned out to be adult websites, but they paid cash. And so I even did a voiceover for a book once.

Yeah, who knew?

But I actually screamed for a few hours to make my voice super raspy. That was what they were looking for in the character. But I just did anything I could to try and pay off this debt, and it took me from then till, till basically the Google IPO to selling another company in the Google IPO before I got back to zero net worth. And I'll tell you, no matter how early you are in your career, the richest you will ever feel is when you owe $0 to anybody. That's the very first time in your life when you've got choices. You can, you could go join the Peace Corps, you go travel the world, you could do anything. I actually celebrated by throwing a BYOB party at my house.

Like, I'm not going in the red to treat all you guys.

But that, that was a real pivotal moment in my life. I'll tell you, I just, I never really considered any other option. I never considered moving back with my parents to Buffalo, New York. I never considered declaring bankruptcy. I just kind of always knew I would fight my way out of it.

And I think that's something that for those of you who are founders, I'd encourage—

not everybody's a founder. It's easy to kind of sign the paperwork, but some of you just aren't founders. And there's a time when you have to admit that to yourself, that it's cool to have a startup, but you may not be a founder. You may not be the kind of unstable, mentally askew person with the slightly manic depressive side who is, who knows in the face of insurmountable odds that you're gonna win. And I don't mean as convinced that you can sell people and convince people of that. I mean, you know in your bones that you're gonna make it out. And I think that's something that was a little different about me. It was like in that hole as advisors were saying, look, just go BK and 7 years from now you can walk away from it. I just knew I would fight my way out of it. And I didn't have to convince myself or anybody else.

I mean, you are unforgivingly who you are. Have you always been like that? No. What happened?

Like when I was in college—

What were you like? Like were you ever insecure?

I still am insecure. Like, I mean, there's probably people snickering backstage right now at that question. Like, um, I— when I was in college, I didn't want to come out as a progressive because I would eliminate like half of my future employers.

In Washington, D.C.

I was like, look, I gotta look neutral here so I can get a fucking job someday. I found progressively, you know, and some of these lessons were foisted upon me. I mean, I mentioned earlier, so not to repeat a story, but it's at Google, I am working on this team on this wireless stuff. It was an incredible amount of responsibility. Larry had given me, Larry Page had given me billions of dollars to go take on the wireless carriers. And I was in over my head. I didn't have a background on this stuff, and I was learning fast, and I was pretty good at it, but one day a decision came up, and I didn't know what to do, and my work partner wrote in the notes, "Chris doesn't know what to do about this." And at Google, the notes are published to the whole company. So I see the notes get published, and I'm like, "What'd you do? You just ruined my career. Everyone's going to know, like, I'm smoking mirrors." And I thought it was over for me. And then the next meeting, some new engineers who didn't report to me and Larry Page himself showed up with ideas on what to do to solve this problem. And I was like, oh my God, I just became more powerful. I now have influence. I have more bodies working for me who don't even report to me. And it was— I mean, I wish I could say I was like, it was an enlightened choice I'd made. It was totally foisted upon me and I was angry about it, but it worked. And so along the way, I realized that the candor, the authenticity, the vulnerability is what actually attracts the other people to you. It's, it's the insecurity roots you in this place of showing you're impervious, that you've got all the answers.

But what that does is it renders everyone around you helpless.

They're just like, fuck, I'm not valued here, right? And so when you start to admit like, I don't know what I'm doing, I need some help, then people start attracting you and working with you. I mean, I, I have a principle that I guide my life by and I try and teach this to our entrepreneurs called bold humility. There are all these business books that say, like, hey, be humble, be humble, be humble. But humility is not a natural state for a kick-ass human being, right? Like, if you're here, you probably kick a lot of ass at something. You are probably the best at something. You have ambition, you're a risk taker, you have learned to hack, you are a good talker, you have, through the gift of gab, wound your way into an amazing situation.

You hustle, hustle, hustle.

And I feel like it's unnatural to apologize for that. But where we get into trouble is when we feel like we have to extend that to the shit we don't know. And we have to feel like we've got it all covered. And so I think I have had such a great, like, I don't know if I would have learned this authenticity if I didn't have Twitter. And the replies being like, that means a lot to me, go for it, you know?

And that's why I kind of live a lot of my life in public.

As I feel I draw a lot of strength and reassurance from the public being like, "Look, that moment of fucking failure meant a lot to me and I identify with it." You haven't gotten every investment right.

Tell me about the worst misses that you've had or sort of the biggest setbacks there.

Every investment you get into, you're getting in there because you think you have an airtight thesis for why this thing is gonna work out.

You're convicted, you're passionate, you're putting not just your money in, but put all your time and effort and your, your own brand and your reputation is on the line. And more often than not, we're wrong. But even more painful are some of these ones where I didn't invest at all and they've gone on to be the mega unicorns. I think about Airbnb. When they told me the pitch about renting out a room in somebody else's house while the owner was still there, I literally looked those guys in the eye and I said, You guys, this is so dangerous, man. Somebody's gonna get raped or murdered and the blood is gonna be on your hands. I think this is just a really bad idea. I think they're currently raising at a $20 billion valuation now, so it means my fund probably missed out on hundreds of millions of dollars as a result, right?

Well, I only have two speeds, like asleep or going all out.

All out.

Life is way too short to do anything else, but I seek out argument. You know, Travis Kalanick is just one of the most opinionated, opinionated people in the world, and the nature of our friendship is beating the shit out of each other. You know, I mean, that was—

So, I've heard that there's a Wii, uh, tennis, Wii racing anecdote you want to extrapolate on that?

Well, I, I, yeah, maybe some of you guys know this story, but it was New Year's Day, like 2010 maybe. Travis was staying up at our house in the mountains, and my dad loves playing Nintendo Wii tennis. He's pretty good at it, actually. And so he says, Travis, Travis, come on, let's play tennis. Let's play, you know, and Travis is bleary-eyed because we've been up all night for New Year's, and he says, okay, Mr. Sucker. Saka, and they start playing, and my dad is like up swinging and going for it, and Travis is just sitting on the couch, like eyes barely open, kind of doing this, and he's beating my dad, who's getting visibly frustrated. He's sweating, he's swinging hard, and he's like, what the hell? And then Travis does that like Princess Bride thing where he's like, I'm sorry, Mr. Saka, but I'm not left-handed, you know, whoosh, and then starts playing right-handed, and he's making movements this big, just that, and he's acing my dad. My dad is like, what the hell is happening here? And Travis said, "Okay, Mr. Sack, I'm sorry." And he uses the remote to page over to the global leaderboard, and Travis Kalanick, while being CEO of Uber, was ranked number 2 in the world at Wii Tennis. Who here wants to compete with a guy like that? He was also globally ranked, he was like a top 10 Angry Birds player.

Wow.

The guy's a fucking maniac, right? So anyway, I seek out people who are not normal. I seek out weird people. Like, I won't invest in anyone who's not really weird. I think you need to have some kind of imbalance to do this well. And that's what's exciting. I mean, I get most excited, you know, so I'm on the show back in the United States, Shark Tank. I know everyone has their different version of it. And people ask why I agreed to do it, 'cause the deals there probably aren't gonna make me any money or anything, but the biggest draw is if you watch that show back home, you're like, Mark Cuban, you're full of shit, right? And so I get to now go on the show, and on behalf of all of America who wants to bust his balls, I get to do it from a few chairs away. And he's wrong, wrong most of the time. And so that's like a sport for me.

But you make a good point, it's old tech. But there's a ton of old tech in real estate because it's so sleepy valley.

I've already seen the new tech out there. It's there.

I used it last week.

No, no, that's not true. And that's—

you're living— what do you mean?

No, that's denigrating to him, Chris, because the key isn't the software. The software is the easiest part.

No, no, no, like, Mark, you're not making any sense at all, man.

I'm making total sense.

No, no, you're not. Where?

No, no, where? How is he aware of that place?

I know this is going over your head.

No, it's not.

Do you think people drive down the street and look for houses?

They see their dream home, they see a for sale sign, they'd love to get in. You don't understand.

And then what do they do?

Mark, what do they do?

The device exists today. It lets you in by Bluetooth on your phone.

Not in that circumstance. Not in that circumstance.

With one new line of code, it can let in anyone.

So in your example, I drive by and I want in now, right now.

Yep.

Right now, who do I call?

So you ping in the—

no, look, look, look. With the existing—

Exactly.

Hold on, hold on.

Exactly.

Shut up and listen. Don't be mad at me that I understand this better than you do. I mean, look, you're saying he's got some special way of getting access to media.

No, no, no, no.

And they're already ahead of him. They have exactly that.

You have to go through the agent to get— in order to get— the agent has got to send it to your sharks. We can disagree.

Look how any agent gets into a house with the other technology.

They walk up, boom, they're in the house.

So what you're saying is what the agents do, you can enable for the consumer to do.

Absolutely.

Right.

I get that.

Hey, thanks for catching up. I appreciate it.

Except if you're not using the agent, you don't want to call the agent, and you want to make it available so that the keys are right there and somebody who's comfortable with keys can use it. But he can't do that.

He doesn't have a natural advantage.

Hey, why don't we agree to just—

So why are a million lockboxes, the traditional lockboxes, why are a million of them sold a year?

And why does the other company have millions of dollars worth of sales already doing exactly this? All they have to do is flip one bit and expand their audience, and they make—

How do you connect those boxes?

How do you connect those boxes?

Good luck, guys.

I wish you luck getting your money back.

Have a seat, Chris. We all agree we disagree.

No, you got it wrong, Chris.

I sometimes wonder how you made all that money, Mark.

What's success anyway? Is success about making the most money?

No, not— no.

Money, for the most part, turns people into jerks. If you do become rich, the University Fundraising and Development Office will certainly want to stay in touch with you.

And if you give enough money, you'll get your name on a plaque above the dirty laundry bin here in the men's locker room.

But that still doesn't make you a great person, and it definitely doesn't mean anyone will like you. I mean, don't get me wrong, as I mentioned before, you're never going to feel richer than when you've paid off those credit cards and student loans. But after that, money tends to be pretty unfulfilling. Almost all the people I know who've made a lot of money, they turn into that guy, alright, well you know the guy who pops his collar, and if it were up to him and he were wearing two shirts, he could pop both collars? That's the guy. So how will we know when we've done it right? What's the ultimate measure of success then?

What's the key to success?

Well, in my experience, quite simply, success is happiness. It all comes down to happiness. And I definitely don't mean that happiness that you feel when the Gophers take over on downs in their own red zone, as great as that feels. I mean that happiness that quite literally fills your lungs. The kind of happiness that makes a noise.

It announces its arrival with a deep inhale and a deep exhale.

Ah.

That happiness.

You know that happiness, right? That happiness is success because it turns out happy people get jobs. Happy people create. Happy people win. Happy people fall in love and raise families. They lead and change the world. Happy people get what they want. Because often happy people are the ones who realize they don't actually need much more than they already have, and they appreciate what they've got. Happy people are contagious.

Some of you aren't founders, and you should fucking admit that to yourselves. So it's become very fashionable to start something. It's amazing, you know, when Justin Timberlake plays somebody in a movie about, you know, about a startup, that's awesome. There are lots of people making a ton of money and on magazine covers, But this is a very special, different journey that is not actually suited to everybody. You have to be a little fucked up. You have to be a little weird, a little crazy, a little obsessive. You probably have some personal issues that make you different, like you have some demons a little bit. You may have trouble relating to other human beings from time to time. Like, you don't accept failure very well. Maybe you go off a little bit. Maybe you struggle a little bit with with manic depression, et cetera. Like, if none of those things sound familiar to you, you should probably quit right now. So, sorry if that's a little bit of a downer, but I just, some of you should be employees, some of you should be partners, some of you should be employee number, you know, number one at a startup, and I think right now, oh, that's amazing, they actually showed us a hurry up please sign.

Yeah, I know, but that's good, but finish the thought, because I think that's powerful. And people should hear that.

No, I— there are founders and then there are team members. And in an era where it's been so easy to get capital, I just think the posers should step aside. I guess I just think our industry is blind to the impact, to the—

to how—

I think we have written human beings, our emotion, our purpose, our community our collective humanity, our empathy have all been written out of the algorithm. And I think that's going to cost us in the long run. It will not only help the rise of despotic leaders, but I think it's what's actually severing our connections between each other. You know, I think technology has evolved a lot faster than our primal brains have. I think We've lost track of how important presence is, constant notifications and buzzing and what the impact that's actually having on our health and our lives. And so I think if we don't wake up very soon to the absolute dearth of humanity within what we're building and have that baked right into our mission, our values, our purpose, our hiring, who we brought into these companies, then we're gonna lose. We're gonna lose not just on the investor side, not just on the product side, but the monoculture will eat itself and our, our entire planet will suffer as a result.

Thank you guys so much for watching. I made this video because Rajeev Lopa asked me to. So if there's a famous entrepreneur that you want me to profile next, please leave it down in the comments below and I'll see what I can do. I'd also love to know what did you learn from Chris that had the biggest biggest impact on you? What lesson are you going to apply most to your business or your life? Please leave in the comments below and I'm going to join in the discussion. Finally, I want to give a quick shout out to Edwin, who's one of the assistants at Toronto Dance Salsa. Edwin, thank you so much for picking up a copy of my book, Your One Word. It really, really, really means a lot to me. And taking that picture and posting on Facebook, I'm really feeling the love, man. So thank you guys again for watching. I believe in you. I hope you continue to believe in yourself and whatever your one word is. Much love, I'll see you soon.

What advice would you give for someone in their early 20s living in this era, in this time of—

Yeah, number one, spend less money.

Mm-hmm.

I think the freest you'll ever feel is when you don't owe anybody any money, when you have all these choices in the world. You know, you guys have the benefit of like No, I've never went bankrupt. I've lost tons and tons of money. Well, first of all, in the United States, we have to pay a lot of money for school, so that's one of your competitive advantages. I left college and then into law school, so it was 7 years of school, and I owed like $200,000, and that was 20 years ago. So that's bad. I think it's already a competitive advantage you guys have, and you like to go to hospitals and shit. Yeah, it's amazing. All this stuff we're about to break. Did I just start talking about Donald Trump again? Yeah, sorry. But so, so I just, I think one of the most important things a young person can do is just buy less shit, have less stuff. Stuff just, you're a prisoner to your things, right? And so you can pick up and travel more easily, you can have a smaller house, you can quit your job and go work in an NGO, volunteer work, you can pursue your art career if you have less shit and owe less money to fewer people. So I think that's like number one.

See, now you're not even focused.

Oh!

Now you're just trying too hard.

I'm beginning to think that maybe you and Matt, the CEO of Automatic, have been playing on that table a little bit, and I got suckered.

I told you earlier, I like to play rigged games.

I don't invest in companies where I don't think we have a competitive advantage to make it more likely to win. And I wouldn't have challenged you to play badminton because I suck.