Chris Sacca: Putting It All on the Line

Chris Sacca: “We're going to write a grant that was going to take 10 years and we were going to do some theoretical modeling.” We're like, “With a million dollars, could you just put this in a farmer's field starting tomorrow and gather some data and see how that turns out in a couple of years and if so, then we can just do it all over the world?” They're like, “Well, yeah.” We're like, “Okay. Well, that's the Google, Silicon Valley way. Let's just stop talking about it and get to work.”

Michael Redd: Hey, everybody. This is Michael Redd and welcome to the Betting On Yourself podcast where I interview successful entrepreneurs, athletes, and other top performers who rose to the top, took success into their own hands, and bet on themselves. Welcome to season two of Betting On Yourself. I couldn't think of a better way to kick off this season than with this amazing interview I did a couple of years ago with a venture investor and entrepreneur, Chris Sacca. Chris is the chairman of Lowercase Capital and together with his wife, Crystal, they've invested in over 70 early-stage companies that include heavy-hitters like Twitter, Uber, Instagram, Twilio, Stripe, and Kickstarter, making Lowercase Capital one of the most successful funds ever.

Michael Redd: You might have seen Chris for a couple of seasons on Shark Tank, making deals, but now he has other plans. In 2017, he stepped back from investing to focus on other efforts like wrestling democracy, healing the planet, molding diversity within venture capital and technology, reforming our criminal justice system, and other nonprofits. We had a chance to talk about his road to success and the times and his journey when he had to put it all on the line and better himself to eventually become one of the most successful venture investors ever. Here's my conversation with Chris. Chris, thank you for coming.

Chris Sacca: Right on. It's good to be here.

Michael Redd: We're just got to pick it up, man. We were talking about work ethic, study habits, transitioning from one space to another space, which has not been the easiest thing for me, but it's rewarding because I'm seeing people's lives change. Talk a little bit about that and then we'll go and backtrack to your childhood a little bit.

Chris Sacca: Look, I think we're all still novices at the investing world. I think the minute you start taking it for granted is the minute you fall on your face. The minute, I think you start believing your own BS a little bit is when it all falls apart. I think one of the reasons why we were so successful in this game, and I've since left the investing game, was that I tried to look at every single deal with a brand-new lens without having any preconceived notions. We never had an idea like, “Hey. People sharing their stuff in marketplaces with other people is going to be a big deal.”

Chris Sacca: That's how we found Uber. Instead, we were just working on disruptive ideas with our good buddies at the time. The idea for Uber came up and we were like, “Oh man. That could be transformational.” No one was looking for 140-character microblogs when Twitter happened. No one was looking for photo filters when Instagram came around. I could go down the whole damn list of those things. I think you have to be able to have the attitude that every single one of these is going to be a brand-new opportunity to learn and come at them with that lens of a novice. Now, as you do this more and-

Michael Redd: Sure.

Chris Sacca: More, you develop this experience. Sometimes that experience is how am I more helpful to this company? All right. I've seen a CEO in this type of transition before. I've seen an offer come in like this or I know that this kind of culture is moving in the wrong way. I got steer it in another way, but a lot of what you're learning is just how to handle your own psychology. It's just like, “I know I'm getting giddy about this, but it's getting in the way of my rational thought” or, “My rational thought is getting in the way of my gut feeling. My gut feeling was telling me this deal is going to be big.” I think, to that initial point, you've got to come at this as a beginner. If you don't, you're going to fall down. I think that's one of the challenges I started to feel later in my career, was that I'd also lost that excitement for each new deal.

Michael Redd: Wow.

Chris Sacca: You have to come in this with optimism and skepticism and balance. After you've seen literally thousands and thousands of thousands of pitches, the eyes start to glaze over. I started to lose sense of my optimism. I had seen so many things fail, so many pretenders as CEOs, so many bad ideas not pan out, so many teams break apart that I started to lose that optimism, that fresh mind you have to have with every single deal.

Michael Redd: Wow. Well, I'm going to backtrack a little bit to your childhood. As a caveat, I want to say this. I didn't know and you didn't know that Chris Sacca now is a sneakerhead. That's the one thing that we both have in common now, is that we both love sneakers.

Chris Sacca: These are the new Nikes. You haven't seen these.

Michael Redd: It's your swag. I love it.

Chris Sacca: A buddy of mine, Adam Bain, who's on the board of GOAT got me the app. They've made it too easy. You push a button. I was in Japan recently and saw some hot kicks. Now, I just came home. I was gone for three months. I just came back to my house and there was a stack of new joints.

Michael Redd: Feels good.

Chris Sacca: It is. It's fun.

Michael Redd: Welcome.

Chris Sacca: Thank you.

Michael Redd: As a child, what was Chris Sacca's biggest dream? Did it look like what it looks like now?

Chris Sacca: I was good at a bunch of things. Actually, the first thing I was as a writer. As a kid, I was winning national story writing contests, stuff like that. I loved that.

Michael Redd: Wow.

Chris Sacca: I was also a young scientist. I wanted to be an archeologist like Indiana Jones. I wore the hat to school. They wouldn't let me bring the whip to school. Then they found out I was really good at math, so I started going to the University of Buffalo for math at the end of sixth grade. After regular school, I would get in the car and I'd go to the university and do a math degree.

Michael Redd: Wow.

Chris Sacca: Around 11, I tapped out. I was burned out on that a little bit. It was one of these first experiences I had with, well, I'm really good at something, but is that really what I want to be doing? I had this exceptional talent. It's easy and my parents are very chill about it, but a lot of other people in my academic world were like, “You got to pursue this. You got to do this.” It was one of those first moments where I had to make a decision like, “Is this really what I want to be doing?” Back then, I did have a lot of hustle. I was the guy who … At five or six, I was picking up walnuts in my front yard.

Chris Sacca: I grew up near Buffalo, New York, similar to Ohio, same climate. Walnuts, when they come down, they have that green skin on them. I'd poke holes in them. They're really aromatic. I'd go door to door selling them as air fresheners. People in the neighborhood just chuck me a quarter out of sheer sympathy. I just always had a hostel. In high school, I was selling Blow Pops. I helped run a cardroom. I had a teacher who just passed away recently, so we can disclose this now, but we gave him a little piece of the rate. We'd run Blu-ray games and Spades.

Michael Redd: Boomerang.

Chris Sacca: There aren't many people that know that game. You know that game?

Michael Redd: Of course.

Chris Sacca: Progressive talking is where it's at. I ran a cardroom. I always had a side hustle of some kind. By the time I got to college, I was helping people with their ID situation. I always had that … I liked the entrepreneurial spirit. I liked being part of that game, but I also, when I chose the college to go to, went to the School of Foreign Service at Georgetown. I grew up without much money and upstate New York. I hadn't really had the chance to travel abroad.

Chris Sacca: It was so exciting. It was the one super-high school quality undergraduate program in the country that didn't have a math requirement because I just didn't want to go back to math anymore. That was really fun. I was pretty good at school. I loved studying and traveling abroad. I was in Ecuador, El Salvador, Spain, Ireland, studying, living, working a little bit. Then when I came out of there though, you asked what was my dream, at that point, I wanted to just make some money. Not coming from money and being-

Michael Redd: Sure.

Chris Sacca: Exposed to so much money at school that, that did become my focus. It sounds less poetic or something like that. I think people take various paths IN Silicon Valley. Mine was just like, “I want to make some money.” I think the best way to make some money is to be on that entrepreneurial path. Now, as a non-engineer on the East Coast, it wasn't the Stanford network world and stuff, I was trying to figure out a way to seat at the table. An MBA program wanted years of work experience, first. I didn't have that and I didn't have the time to do it. I was going to start paying back all these student loans. I went to law school. My dad was a small-town lawyer in partnership with my grandfather. I interned at the DA's office when I was 15.

Michael Redd: Wow.

Chris Sacca: I got some exposure. Then I'm like, “All right. I can do law school pretty easily. It just comes naturally to me.” I did that, but with an eye, not to become like a litigator and a trial lawyer, but with an eye to what's the fastest path to get a seat at the table in Silicon Valley? That worked out. I got hired at Fenwick & West. It was sweet. I was in the center of all the deals. Then four days before September 11th, they fired me. They laid off my whole class.

Michael Redd: Wow.

Chris Sacca: For four days, I thought I had job prospects. Then the Twin Towers come down and I'm like, “Oh, there's no chance I'm getting back.”

Michael Redd: How was that feeling?

Chris Sacca: Well, that was devastating. I'm lucky enough in that, my parents have always been middle-class, I had something to fall back on. I could have moved back to the small town outside of Buffalo, New York, but I think compared to my ambitions, that would have been ultimate failure. I know I was privileged in that a lot of people don't even have that to fall back on. To have to suffer that kind of setback was just daunting. I just considered that not to be an option. I said, “All right. I'm going to have to figure it out.” Now, along the way, I'd also borrowed a ton of money. I was day trading stocks all through law school. At one point, I was at 12 millionaire and a few days later, literally, I was at a negative four millionaire.

Michael Redd: Wow.

Chris Sacca: The market crashed. I had all this leverage. I was in real trouble. Fast forward, not only did I lose my job, but I also, by the time I negotiated it down, owed $2.125 million in my own name. I couldn't go bankrupt on it. I was just screwed. I didn't consider failure an option. I was like, “All right. This is a setback, but I got to do something about it.” It sounds insane now in retrospect because that's more than most people ever make in a lifetime. I just didn't give myself the option not to do it. I set about building adult versions of side hustles and stuff to try and do it. I had a business card. At first, it said Chris Sacca, attorney at law. I would go to these conferences in Silicon Valley and tell people my story. They'd be like, “You sound like a smart kid. Things will work out for you.”

Chris Sacca: I'm like. “They don't understand. I got to make rent this week.” I ended up creating a business card that said, “The Salinger group.” I just came up with a name. I put my name on it, Chris Sacca, principal of The Salinger Group.” Crystal, who's now my wife, was my best friend for a long time. She designed the logo for me. It looked badass. I would just go out to the same event. It was weird. I lived in probably a couple of dozen square-foot apartment. It was a hovel with the bed, the kitchen, and everything all in one little room, but I was just trying to scrap together, taking a little equity, trying to be helpful. That started the turnaround. By the way, along the way, I was doing gigs off of Craigslist, freelance. I was taking 50 bucks for … I even did a voiceover for an audiobook once.

Michael Redd: I don't mean to interrupt you, but I heard that you sent out 784 resumes.

Chris Sacca: That's exactly right. I heard no replies.

Michael Redd: Wow.

Chris Sacca: I was devastated. I took the time too to really tailor my cover letter and my resume to exactly the job description because a lot of people have software that looks at those things. I got zero. In fact, of that group of people that I sent those resumes to were all the members of this list called the Midas List. Forbes every year calculates the top a hundred investors in tech. It's called their Midas List.

Michael Redd: Wow.

Chris Sacca: Who's got the Midas touch? I got the issue and I wrote to all of them that I could get an address on and didn't hear back. Fast forward later, that is the only list that has ever mattered to me and is the only list I ever wanted to get on. I was never on a 30 Under 30 or 4o Under 40. I don't even think they do 50 Under 50s, but that list was the one that was important to me. When I finally, later in my career, started making on that list … You come into my office, that shit is on the wall. That was the one that mattered,

Michael Redd: The tenacity that you have, man, has been the hallmark of your life. I can relate to that, being a 20-year-old kid who leaves school early and everybody talks about and says, “You're making a bad decision.” I believed in myself. I get to the NBA and get drafted late, second round. I have no money, no guaranteed money. The struggle … It's funny how people perceive you now. “Oh, Chris Sacca is this great investor. He's a successful man,” but a lot of people don't know the struggle that pushed us to where we are now. I remember having holes in my shoes as a kid. A middle-class family, similar to yours. I think there's something to be said about that, the struggle that pushes you to where you are now.

Chris Sacca: Look, I'll never say that my upbringing was the kind of struggle that I know, that I've since had the exposure to, that I understand so many people in this country grapple with. I think that's getting worse for so many people. We don't have that safety net we used to. Jobs that used to be safe careers and retirements are now just hourly jobs without healthcare. I think for a lot of people, the obstacles they are overcoming are harder than ever. Think back two generations. We had this thing called the GI Bill. Basically, you fought. You gave up that sacrifice. Now you can get access to money for college and home loans.

Chris Sacca: As long as you get up in the morning, there's a job waiting for you. For too many people, that's not the reality. I want to just preface it by just saying I feel incredibly lucky for the way I was raised. I had two parents at home who cared about where I was headed and who made sure that when some of my friends were goofing off, I was at home being safe, doing work, that kind of thing. Let's just say that upfront. That said, there still is some social and economic mobility in this country, probably more than anywhere else, even though I think the situation is worsening. I think we have an education-

Michael Redd: I agree.

Chris Sacca: Divide, a healthcare divide, even a food divide.

Michael Redd: Yes.

Chris Sacca: We have food deserts in this country, places where you can't get healthy groceries.

Michael Redd: True.

Chris Sacca: That said, there still is some opportunity there and it is the root of what makes America America right now. It's the last thing we can cling to. We piss all of our environment. There's a host of problems here, but that's one of the last paths to opportunity. My personal motto along the way has been it may be lucky, but it's not an accident. I can look back at my path and see individual moments that feel very lucky. This person introduced me to this person. This person happened to show up at a moment when I was doing something incredible. Somebody at work came and said, “Will you work on this project with me?” That ended up elevating my career. It's easy to look back at each of those and be like, “Man, what if that person didn't introduce me to that other person who ended up being really crucial to me?”

Chris Sacca: We call them single points of failure. If that didn't happen, maybe it all falls apart. You have to believe. I think if you're really on your way to be something special, you have to believe that even if person A didn't introduce you to person B, at some other point, awesome person C was going to introduce you to awesome person D and something similar was going to happen. Even though your life might have gone in a different direction, it was also going to be great because you put yourself in that situation. You created that opportunity. You worked that hard. Going to school for math, going to night school at college for math while I was in high school, was not easy.

Michael Redd: Wow.

Chris Sacca: It meant passing up a lot of nights playing cards with my buddies and stuff. Luckily, I stayed in my regular grade in school and still had dates and still played sports and stuff like that, but it comes with some sacrifice. You didn't get to do what you're doing by having a normal life and not working your ass off all the time. What I try to do is not apologize for all that work I did. I recognize the privilege and the good fortune that got me there, but realized that as I look at all these people who you would consider to be overnight successes, 10 to 15 years is a pretty good overnight success at our industry, 10 to 15 years of obsessive work.

Michael Redd: You mentioned moments. I think we're at a segment in the podcast where I want to share about a point of no return. I'm all in. I'm a risk-taker in this very moment. Give me an example. What was your moment? There were many moments, but-

Chris Sacca: I have a few of those, but one that sticks out for me, it's 2007. I have risen through the ranks at Google, to where my name or my title is Head of Strategic Initiatives. I work for Eric Schmidt, Larry, and Sergey, David Drummond, solving just big, honking, awesome problems. They gave me $4.7 billion to take to the FCC spectrum auction and just clear stuff up and mess with wireless-

Michael Redd: Wow.

Chris Sacca: Companies. I was building billion-dollar data centers around the world, server firms that hold all our stuff. I was part of the Wi-Fi team. I co-head the Wi-Fi team at the time and got to work on all kinds of crazy stuff. One day, it just started to feel like a big company to me. I was showing up to meetings and people were like, “Wait.” They started defining themselves by their territory. You're the wireless guy? Why are you in this YouTube meeting? I'd be like, “Well, because Eric asked me to try and unscrew this whole situation, so I thought I'd be helpful.” They're like, “Yeah, but you're the wireless guy.” Instead of being on the same team, people started really just being like, “Well, this deal should be done by my team. Your deal should …” It just really felt like it was big company stuff now.

Chris Sacca: Nobody was looking out for Google as much as they were looking out for their own little territory. I just told Eric, Larry, and Sergey that I was leaving. “What do you mean you're leaving?” I was just like, “I'm out. I feel like I miss startups. I miss when we were all on the same team.” In the early days, I sat with the head of all operations, a guy who was employee number six there, named Urs Hölzle, one of the smartest people I've ever met. We shared an office. Nobody at Google had their own office. We all shared, no matter how fancy you were. They were all small. I saw a contract combined my email for the company ski trip to Truckee, California, where I ended up living, in Squaw Valley. It was going to be $800 a person for two days, one night. I decided under my breath, like, “That sounds like a lot of money.”

Chris Sacca: The guy who ran all of operations and half of engineering overheard me. He's like, “How much is it?” I'm like, “$800.” Now, this guy, literally, has a budget of billions of dollars buying servers, buying chips, and all this stuff. He's like, “Let me see that.” I showed it to him. He's like, “That's crap.” He's like, “What's their phone number?” We look in the contract for the phone number. He just calls up. He's like, “Hey. This is Urs from Google. That's way too much money. We're not going to come unless you do something about it.” They're like, “Okay. I guess we can make it 400 bucks.” He's like, “Thanks. Bye.” I was like, “That's amazing.” That guy just stopped his work to do something for the company and everyone gave him a pat on the back for it because we're all one team. As the company got bigger and people started keeping their own score, it was frustrating. I just told the guys I was leaving.

Michael Redd: Wow.

Chris Sacca: It didn't make any sense. I didn't have a plan. I wasn't rich. I was going to be an angel investor, but I had less than a million dollars. Normally, to get be an angel investor, if you're going to break off 25 and 50k-

Michael Redd: That's a lot of money right there.

Chris Sacca: You better have a lot of money to back that up, but for most guys, that's just money. I really needed that money and I didn't really have it, but I just left. I was feeling pretty good about it. They had a nice going away party for me and stuff like that. Then right around Christmas time, I was back home for the holidays. The New York Times wrote an article. Essentially, it said something like, “Why would this guy leave the greatest job in the world?” I was just like, “Oh my God. What have I done?” I started crying at my mom and dad's table, like, “I just left the greatest job in the world.”

Chris Sacca: I was like, “Those guys just gave me all these cool challenges and an unlimited budget. I was making money.” I left about 10, $15 million on the table when I left there. They just gave me a big new stock grant and stuff. I didn't get rich while I was there because I was hired as a junior person. I walked away from a lot of money, but it turned out to be the best thing that ever happened to me. I suddenly was in control of my own destiny. In fact, I had a mentor who since passed away, this guy, Coach Campbell. He was a mentor to Steve Jobs and Eric Schmidt.

Michael Redd: Wow.

Chris Sacca: A bunch of amazing people. I call him coach because I think he was the football coach at Columbia for a while. Not a winning coach, I think, but an incredible personal coach. I asked him. I had offers to join a couple of hedge funds or a private equity fund or another venture fund. He said, “No. Start your own thing. You suck at having a boss.” I was like, “That is a really good insight. I do suck at having a boss.” I started my own thing. Even then, I didn't really have a plan. Mentors along the way were like, “Look, you should just pull the trigger.” I'm like, “I don't know how to manage anybody else's money.”

Chris Sacca: My first investor was like, “Well, if you can raise six million, we'll give you two million, and then you can use our accountants to manage the back office.” They said, “The hardest part is the deal work. Don't let the finance stuff get in the way.” Within a couple of years, I was a venture capitalist and that was not … I wish I could tell you like, “Hey. I grew up in Palo Alto and saw [inaudible 00:22:34]. I knew I wanted to do that.” Or, “Working in the MIT Media Lab, I got exposed and I wanted to shape the future” or anything like that. I just bumped and bruised along the way. Fast forward from there, now I have the most successful venture fund of all time.

Michael Redd: Wow.

Chris Sacca: In the beginning, it was hard to convince anyone to invest their money with me. Now there's more than we could ever want.

Michael Redd: Sure.

Chris Sacca: I had to do this. I had to take inventory a couple of years ago and it took me back to that math thing again. I'm really, really good at venture investing, but is this really what I like to do? It turns out no. I think the biggest thing when you go back to that red zone moment, whether it was quitting, going to college for math, whether it was walking away from Google, when I was finally getting successful and powerful there or whether it was quitting the venture industry when I was at the very top of the game, I finally made it to, I think number two on that Midas List. I never made it to number one.

Michael Redd: Let me shake your hand for that.

Chris Sacca: I've got them all around the office. Finally, I was like, “They gave me the cover. I'll take it. I'm done,” but I think in each of those moments, it was realizing no one else in the world has your same scorecard in front of them. No one else in the world knows your priorities, not even your spouse, not even your closest friends, not your family. When you grow up, you've got family, hopefully, looking at for you. They're selflessly thinking about what's best for you. Some of that though is imposing their will on you. You hopefully have some teachers looking out for you like, “This is what's good for you.” Hopefully, you've got someone for the rest of your life, outside of school. Maybe you've got some friends there, some distant relatives, or maybe someone from your faith, all trying to look out and help you along the way.

Chris Sacca: You get to college. You're lucky enough to go to college. Hopefully, you've got some professors who realize there's a spark in you. They want to spend some time. Hopefully, you got some good classmates doing that. When you finally graduate and you're out in that corporate world or you're a professional athlete or you're in entertainment, you soon realize there's no dad. There's no mom there. There's no benevolent, selfless professor looking out for you there. You're a piece of an overall machine. You're a cog. They know their selfish interest and why you're there and how you're helpful to them. Even if they try … I think all of us try and pay it forward or mentor somebody, but I can't take my story and impose it on somebody else. I think that's a trap we all fall into if I say, “Hey. Look, it worked for me, so it'll work for you.” There is no cookie-cutter way to do this.

Michael Redd: I agree.

Chris Sacca: There's this moment where you have to come to grips with, okay, there might be some well-intentioned people around me, but nobody else actually knows my motivations, my passions, my interests, my fulfillment, my happiness, my peace better than I do. That's scary because in the age of Twitter and bloggers, and reporters everywhere, when you make some of these moves, everyone's like, “What the hell? That's stupid. That's dumb. Why would you do this?” Et cetera. It can create some self-doubt, but I think that's one of the most powerful things, is how to check like, “What matters to me right now?” Go ahead.

Michael Redd: That's powerful because in the midst of all of your success or ascension to being one of the great investors in America around the world, family, I know is important to you. What you're saying is that you're intentional about your energy and your time, especially as you get older and you value that. I can hear that. Tell us about your time with your family and the balance between being this great investor in these businesses and helping mitigate risk and all this, and also being a family man and how important that is.

Chris Sacca: Some of the people I respect most in this business are the people who can pull it off with family. I don't just mean on the investing side, also on the founding side or as executives in some of these companies. I worked with this woman named Susan Wojcicki a lot when we were at Google. Hers was the actual garage that Larry and Sergey … They got kicked off the Stanford campus, running their business. They were running their-

Michael Redd: Wow.

Chris Sacca: Original business in the dorms and the servers are making the dorm rooms too hot, so they got kicked off to a garage. It was her garage, so she's been involved since the early days. She's brilliant and ran a huge chunk of the ads business at Google, billions and billions of dollars. I loved the way she managed. I never worked for her, but being in her orbit was amazing. We'd go into meetings and they might be scheduled for an hour, but if the work was done in 37 minutes, she just called it. She kept it so that things were always low drama.

Chris Sacca: You could tell if you disappoint her. You could tell her if you pleased her, but she didn't let her heart rate get crazy with it. Her day ended at 5:00. You were not going to interact with her at 5:01. It was family time. Then she would come back online around 10:00 and do a little email before she went to sleep then. It was just this … I really admired her because her relationship with her family built efficiency into her work and prioritization. I love when … I've got a nephew who just joined one of the greatest architecture firms in the world.

Michael Redd: Wow.

Chris Sacca: My wife and I were telling him, “Look, you're in your 20s. This is the time when you can just spend all hours at work, have no balance. You don't need any …” Sure enough, we hit him the other night. It was midnight. He's like, “I just ate dinner. I'm still cranking here.” We were laughing because we've both been through that phase in our career. When you have all that time in your day, you have the luxury of not having to make any prioritization choices. I'm just saying I can stay up all night and do this stuff. You lose track of whether it's a Tuesday or a Saturday-

Michael Redd: Exactly.

Chris Sacca: In one of those environments, but then you start building a relationship and you have kids in the picture and you have to make really good choices. I think those can actually make you a better business person. I think having a partner and children starts to grow that sense of empathy that might have been there. It starts to help you … Look, hanging out with kids, hopefully, builds that other lens in the world, that new discovery that not everyone sees the world the same way. We have a monoculture that keeps building products for mostly white guys, Stanford and MIT graduates. Start hanging out with kids. Hopefully, your partners are developing that sense of empathy. You're hanging out with other parents. You're paying the mortgage. Once you have kids, you walk into any park, any city and you can go in for the dad handshake with any other dad. No matter what you do for living suddenly-

Michael Redd: Period.

Chris Sacca: You have a conversation.

Michael Redd: President or mayor.

Chris Sacca: You share this tribe. Then as you may make those decisions like, “All right. My kid is singing in concert. I want to make sure I make this meal. Somebody's sick today,” it starts building these priorities for you and you start building better to-do lists. I actually think that stuff can make you better. Then you can also screw stuff up if you don't take advantage. I know people who are incredible business people and don't know their kid's names. Their kids are a mess.

Michael Redd: Wow.

Chris Sacca: They don't parent, that kind of stuff. Their relationships fall apart. I think there is the opportunity to screw it all up, but I think balance can be achievable with good prioritization. We have some good friends who are a couple that are chefs. They together run a restaurant and they have two little kids. They've actually taught their kids. They've shifted their sleep schedule so that the kids sleep at the beginning, during restaurant hours, and then wake up at 10:30, 11:00, for a couple of hours when the parents are done cheffing so they actually get some family time. It sounds crazy, but it's the only way they would be able to be-

Michael Redd: Absolutely.

Chris Sacca: Present for those years of those kids' lives. They put them back to bed for a few hours until the morning starts. You want to be there, but you're cheffing all the time. They're living their dream as restaurateurs. Anyway, for me, I deeply believe in that priority. I'll also say too my kids have grown up with a lot of privilege, which means they have a higher likelihood than most of turning out to be jerks, of not understanding work, of not understanding the human condition, a higher likelihood of not appreciating how hard the struggle is for so many people in our country and beyond because it'd be much easier for them to just have stuff handed to them along the way. It's so crucial. Actually, my wife and I realized that's going to require extra work on our part-

Michael Redd: Yes.

Chris Sacca: To undo some of that privilege and to make sure they have a deeper appreciation for everyone who gets up in the morning and bust their ass.

Michael Redd: Yes.

Chris Sacca: In any part of this society, people from every walk of life and culture, whether they were born here or they came here, it's really important for us.

Michael Redd: How do you balance that? This is a good segue because my kids are now getting to a point where they know who daddy is and they recognize what they have. I asked my dad, I said, “Dad,” I said, “How do you do this parent thing?” Just off the cuff. He says, “Son, I don't know how to parent the way … I just don't know because I had to keep you and your sister off the streets, gangs.” We were in the hood and we were in bad environments. There was an element that he had to keep us away from. He said, “Your kids are privileged. They have everything at their exposure.” He said, “Just continue to teach them how to value people and respect and honor people and things.” How do you balance that?” Because I want my kids to have better than what I had, obviously, but not to the point to where it makes them, to you our point, jerks.

Chris Sacca: I think there's two components to that. One is, just two days ago, something really cool happened with my kids. Our girls are almost seven, five, and almost three. We got some time to spend with Scott Harrison who founded charity: water. It's a nonprofit that we've been longtime supporters of. It digs clean water wells in 26 countries and provides toilets and sanitation.

Michael Redd: Wow.

Chris Sacca: Clean water is at the base of everything. Once people start getting clean water, not only do they stop dying and being sick, but women in many of these cultures are the people who fetch water, so they can stop fetching water and instead go to school. It just really compounds. These communities start thriving. Scott was hanging out and he said, “It's time to tell your girls the story of charity: water.” I was like, “Really? Are they going to get it?” He's like, “Yeah. Watch this.” He put together a little slide presentation that he'd taken from the main story and adapted for them. What I realized was that while our kids don't really understand money yet and they don't understand, we try and do that concept of wages and expenses and stuff like that. It's hard still because they're little. What kids deeply understand is fairness and justice. They understand when something's not fair.

Michael Redd: Yes.

Chris Sacca: Scott started to tell the story about how kids in Ethiopia, their same age, look like them, don't have access to clean water and so they get sick and they throw up. Showing the water that they go and pull their family drinking water from, it's literally shared with cattle and goats, it clicked for our kids. That is not fair. Even though they don't understand all the economics behind it, they're like, “That's messed up.” Scott also broke something to them that we hadn't really explained to them before, which is when each of them was born, we asked everybody, “Please don't send any pink gifts. Our girls aren't princesses. Don't box them in. Do us a favor.”

Michael Redd: Wow.

Chris Sacca: “Donate to charity: water and let's build a clean water well in their names.” Each of these girls has clean water wells throughout Africa, with their names on them. It'd say, “This well is brought to you by, happy birthday, Circa Luna Tahoe Sacca or CC Eleven.” Scott actually pulled up the pictures of those wells. Our girls, I didn't think they would get it.

Michael Redd: Wow.

Chris Sacca: They lit up. They were like, “Wait. My birthday helped 300 people in Malawi drink clean water every day,” even more than 300 people. They focus so much on the kids. “My birthday helped create fairness for these other kids.” You split a cookie the wrong way, you don't get a 50/50 and there's going to be meltdowns with kids.

Michael Redd: Correct.

Chris Sacca: Kids get fairness, right?

Michael Redd: They do.

Chris Sacca: That's when you say it's not fair to these other kids. It was funny. That was just a couple of days ago. Two of them already had their birthdays. They all know are like, “I can't wait for my next birthday. Can I give it to charity: water? Can I help these kids?”

Michael Redd: Wonderful.

Chris Sacca: I think while their journey is never going to be the same as ours, where you got to get that minimum wage job and kick the money back to your parents to take the edge off the plate for your family, I think we can try to build that in through just deep and intimate exposure to people who live in very different conditions. I spend time with Bryan Stevenson this week. He's the founder of the Equal Justice Initiative. If you haven't seen Bryan Stevenson's TED Talk, it's one of those compelling ever. He fights on behalf of children who are on death row. This country still executes children.

Michael Redd: Wow.

Chris Sacca: We try children as adults and execute. Almost all his children, basically all of them are black. You're 22 times more likely to be executed for a crime if you're black and the victim is white than if you're white and the victim is black. It's just nuts. Bryan's a guy who has always personally inspired us. We were with a small group and we asked him, “What can people in this room do to be helpful to your cause?” He, of course, was like, “Hey. Here's some places you can give to.”

Chris Sacca: “Come visit the new monument they did, the memorial they did in Alabama, commemorating our history of lynching in this country.” The number one thing he said was, “Get to know the people on whose behalf you want to advocate. Get to know them and build relationships. If you want to change the criminal justice system, you need to get to know people who are on the other side of the criminal justice system. It's hard to effectively advocate from far away.” That was something that … My wife and I have been leading visits to maximum security prisons here in California-

Michael Redd: Wow.

Chris Sacca: Juvenile facilities and maximum-security facilities and making sure they're hugging-it-out visits, not just from behind the glass, getting to know people. One of my buddies just got noticed. He just got re-sentenced. He's been there 23 years and he's coming out in a couple of months. We're trying to do the same thing with our kids. Instead of making it virtual, make sure they know and have relationships with people who are growing up or who are, by virtue of condition, being born in the wrong place or the color of their skin.

Chris Sacca: Get to know their plight and their condition. Hopefully, they can develop that sense of empathy, that sense of service and duty, and obligation, not just from … I think those of us who all had crappy jobs … I tend not to hire anyone who hasn't had a crappy job because I feel like they don't understand how good we've got it. Our worst day in the investing world doesn't compare to a good day working in a restaurant. It does not compare it to a good day working-

Michael Redd: I agree.

Chris Sacca: Prep in the kitchen or on the line, let alone fast food or retail or construction. I had construction jobs. We were so grateful. My mom and dad made sure we had crappy jobs, starting at age 12. I think not only do I have a deeper appreciation for people who work those jobs, but also just for the human condition when they go home. That four or $6 an hour I was making bought me a little spending money for the summer and stuff like that. I could save it up and buy whatever bike I was going for, but thinking about people putting food on the table for families, trying to pay for hospital bills, and stuff like that, it informs that condition.

Chris Sacca: Our kids may not end up having those jobs. I'd love to, but we also like to move around and travel and stuff, so that might screw them up. In parallel, I can create those opportunities. When we travel, it's travel with service in mind. We're exploring, but we're also going there to be helpful. That may cultivate that same sense for them, I hope. Bryan Stevenson's words, they're fresh, but they're still echoing with me, like, “Really get to know the people who you want to advocate on behalf of and build personal relationships there.”

Michael Redd: In this podcast, I was thinking in my mind, I could quantify your life in three words. The first phase of your life, it sounds like it was survival mode. Then you transitioned to success mode. Now you're at a place in your life where it's about significance. Talk about that a little bit, about how now your life is now more about serving. It's always probably about serving, but serving really on a high level, helping others' philanthropic work that you're doing. That's powerful.

Chris Sacca: Significance is a good word. What we also think about is impact, how to go from success to impact, meaning fulfillment, giving back, paying it forward, whatever you want to ... I think there's a lot of adequate ways to express. A few things. One, resources would be helpful. With those resources comes some responsibility. I remember when I first saw Larry and Sergey at Google make billions of dollars, neither of them got happy. I was really close to them. I saw other people during the IPO were like, “Whoo” and started buying crazy cars and islands and stuff. Larry and Sergey just suddenly so burdened and I didn't get it because I was still paying back my student loans. I would kill to have that money and yet I started getting more and more as good fortune befell me. I was like, “With this comes some real responsibility to affect a change, to help those who don't have this to solve problems.”

Chris Sacca: That's one thing, is the resources. Two is I'm wrapping up that phase in my career where I was professionally solving problems. I was either helping to find problems that exist in the world and a startup would be built to try and address those or solve problems within that startup. How do we unscrew this situation and get the right team in here, get rid of that person, grow, attract the people? How do we tell the story? How do we get other investors or acquirers to come in? How do we communicate to customers what we're actually doing here? How do we help the users understand this product so well that they can explain it to other users because we don't have a marketing budget?

Chris Sacca: How do we do something that nobody else has done at scale? It's not just 10% cheaper, but it's 10 times cheaper. We can get these things to everybody. How do we figure out what the assumptions are in a model? You launch a car service like Uber and everyone's like, “How do you do this without owning any cars?” Well, it turns out it'd be really expensive to you if you own the cars. You lever it. How do we go after brand-new approaches to stuff? Here in LA, we have Shivani Siroya, the CEO of Tala, one of the greatest CEOs I've ever come across. She has an app. When you download it in Kenya, Tanzania, the Philippines, Mexico, India, it instantly determines how creditworthy you are and can make you a mobile money loan on the spot-

Michael Redd: Wow.

Chris Sacca: In those places that have mobile money. She's got people in Kenya, literally thousands and thousands and thousands of people, who are borrowing money. Some of them don't have a permanent address. Most of them have been frozen out of the traditional banking system. She figured out a way to pass all that. Her repayment rates are higher than a lot of FICO-based loans here in the United States.

Michael Redd: Wow.

Chris Sacca: We came from an environment of that, of these radical, bold solutions to problems. Now we've got the resources and we're backing off. We're starting to prioritize what we consider to be bigger problems. I say, “We” because my wife, Crystal, is my partner in all of this. Crystal and I, we got to the point where we just couldn't be excited about the newest app anymore. I just started saying no to stuff. I realized I wasn't even giving it a chance. The Snapchat guys came and pitched me right here in LA, really early on. They came up after a talk I gave and were like, “We love you. We love how you do business. We'd love you to get involved.” I was like, “With dick pics? Really? How does that …?” I just started saying no stuff. I wasn't even getting a fair stake. That literally probably costs me a billion dollars.

Michael Redd: I was going to ask you do you have any regrets at all?

Chris Sacca: Yeah, of course, I do. Look, I told the Airbnb guys … At the time, it was renting out a room in somebody's house while they were still staying there. I was like, “Guys, come here.” I didn't want to embarrass them in front of anybody else. I'm like, “What you're building right now is dangerous and somebody is going to get raped or murdered and the blood is going to be on your hands.” They were like, “Okay, buddy.” I missed that one. I got a bunch of these. I told Dropbox that Google Drive was going to-

Michael Redd: Wow.

Chris Sacca: Kill them. They would never succeed.

Michael Redd: Wow.

Chris Sacca: Look, I'm wrong a lot. When I'm right, I'm really, really right, but I'm wrong very often. In this business, if you're going to be doing this, you're probably … Who knows what ratio it is? We've probably lost money on half or 40% of our investments, but when you're right, you're really, really right. It only takes a couple to define that stuff for you. By the way, now that I'm out, I still feel FOMO when I see an acquisition got announced. I look through the investors and I'm like, “Shit. I didn't see that deal. Damn. That guy's getting rich.” I still feel like it's still competitive.

Michael Redd: Oh, absolutely.

Chris Sacca: I'm like, “Shit. Should I get back now?” Those things, the resources combined with this history. By the way at Google, one of the ways you get laughed out of the room there was to show up with too small an idea.” If you went to-

Michael Redd: I love that.

Chris Sacca: Larry Page with a mediocre, “Hey, we'll just do a trial,” he would just give you this. He has this look like, “Who farted?” You got to roll out because you just let Larry Page down. You got to just come with these big ideas. Google did not mess around. You've heard about net neutrality. We were trying to make sure that you could download all the apps you wanted on your phone. In the early days of mobile, you couldn't do that. You had to get the apps that T-Mobile approved you to get.

Michael Redd: Sure.

Chris Sacca: How do we do this? We're meeting with the different carriers like Verizon Wireless and AT&T, “Please, guys” and it wasn't happening. Somebody on my team came up with this idea, “Well, what if we just …?” I came up with the idea of what if we buy the spectrum? Larry and Sergey were a little freaked out about that. Eric was like, “I don't know.” Then Larry was like, “You know what? That could be a cool idea.” One of our buddies on our team came up with the idea, like, “What if we play this jiu-jitsu where we go into the auction.

Chris Sacca: They're going to auction off this huge piece of spectrum.” We say, "Look, put some openness rules on it. Whoever buys this has to allow net neutrality on their wireless spectrum." We're like, “That's genius.” We go write letters like, “Hey, this stuff should be open.” Verizon was like, “That's easy for you to say, but when we ended up buying it, it takes billions of dollars to operate it and stuff like that.” This guy on our team was like, “Well, let's guarantee them the minimum price then. Let's guarantee $4.7 billion.” We were like, “That's some crazy.” Larry and Sergey were like, “Yes. That's how we think here, from over the top.”

Michael Redd: Wow.

Chris Sacca: We played this huge game of poker that we intended to lose. We were sending all these signals in the market. We were meeting with all these people, about building our own network and the hopes that Verizon and AT& T would realize and they would hear back to the room like, “Oh my God. These guys were serious about building their own network. They're here to take us on.” They had to pay the $4.7 billion. Everyone got a net neutral spectrum. That's why you can download the apps that you want to download today.

Michael Redd: Wow.

Chris Sacca: It was a huge, huge dice roll and a huge bluff. I take those lessons and building stuff. That was just huge, even Gmail. In the early days of email, I remember you had room to keep like 50 messages and you had to start deleting stuff. There was no space. Gmail was like, “What if we gave everyone virtually unlimited space? Then what could happen as a result is it becomes where they start their whole day. It becomes their archive. If we build search over that, this anchors everything.” It worked. It was crazy. Everyone was like, “You're going to lose all your assets on that, but it worked.”

Michael Redd: Wow.

Chris Sacca: We took that same knowledge and we were like, “Okay. We've got the resources now, but we also have this different way of approaching problems.” When we look at causes that we really care about, right now, climate is probably one of the … Top of the list. Climate affects everything. It's not just like, “Oh, it's hot out today.” It creates famine. It creates war.

Michael Redd: That's right.

Chris Sacca: The poorest of the world are most affected by it. It helps spread disease. These fires aren't an accident right now. It obviously wipes out ecosystems. The fish people that we count on to eat go away. Industries are all … It's a real thing right now. I think it's the number one most-pressing issue on the planet. We're way past … The Paris treaty, even if Trump lived up to it, it doesn't even get us close to what we need to do right now. We could give some money to promote some ads and be like, “Hey.”

Chris Sacca: “Turn off your light switches and help save the planet.” That doesn't actually do anything. We're trying to fund research, not even just research, experiments right now in scalable ways that we can take some carbon out of the atmosphere. There's very cool experimental technologies doing that. Or help brighten and whiten clouds to reflect back some of the sun for the planet. It turns out you can just create clouds out in the ocean and then reflect back sun.

Michael Redd: Wow.

Chris Sacca: There's cool stuff. Or grow algae in the ocean. Algae carbon. If you feed them iron filings, they use that. They eat carbon. Then they sink to the bottom of the ocean.

Michael Redd: Wow.

Chris Sacca: They keep the carbon there for a long time. Growing trees and cutting them down, burning them, but when you burn them, capture the carbon and then grow trees in their place again. Take little pieces of limestone and basalt dust and sprinkle it over farmers' fields. Then that sucks up some of the carbon and sinks it into that. It's actually a good fertilizer too. There's these very cool technologies-

Michael Redd: Wow.

Chris Sacca: That are being explored right now that. We go to some of these guys and they're like, “Well, we're going to write a grant that was going to take 10 years and we're going to do some theoretical modeling.” We're like, “With a million dollars, could you just put this in a farmer's field, starting tomorrow and gather some data and see how that turns out in a couple of years and if so, then we can just do it all over the world?” They're like, “Well, yeah.” We're like, “Okay. Well, that's the Google, Silicon Valley way. Let's just stop talking about it and get to work.” These cloud-brightening people were just like, “What do you need?” You go to these really humid places. You throw some dust into the air from a ship. Clouds start forming. It cools the planet. You're like, “Why isn't that starting tomorrow?”

Michael Redd: Wow.

Chris Sacca: We're always looking for ways that we can take the resources we have and apply them in this crazy, bold, scalable way to really change a problem.

Michael Redd: Wow. You're still competitive. You're still motivated and competitive.

Chris Sacca: Well, I'm still also a perfectionist in that stuff. I still am very, very demanding. Clay is here. I'm hard to work for.

Michael Redd: I love it.

Chris Sacca: Even before we put a document out, how many revisions do we do?

Michael Redd: Wow.

Chris Sacca: 45 drafts. That's a good point. My wife and I are pretty serious about the stuff we take on.

Michael Redd: I love it.

Chris Sacca: We want to be proud of everything we do.

Michael Redd: It's a standard.

Chris Sacca: That's another thing we try and show our kids. My dad, when I was a kid, if I mowed the lawn and cut some corners and left some standing around, he would take the blade and lower it a half-inch and ask me to do it again.

Michael Redd: I can relate to that.

Chris Sacca: I don't think I was born with that work ethic. I do think a lot of it was taught to me, like, “Do a great job the first time.” We demand that of the partners we work with. We're doing a lot of stuff in the criminal justice world right now. One thing we're really excited about are these bail funds. Have you come across these bail funds?

Michael Redd: No.

Chris Sacca: 91% of people who are jailed but don't have access to bail money, cash bail, plead guilty just to get out. You're in jail. You just want to get out and get back to your family, but then you plead guilty. Now you've got a record. That's going to hurt your job.

Michael Redd: Correct.

Chris Sacca: That's going to hurt your prospects for benefits.

Michael Redd: It's more like a Jim Crow type of setup. I can go down that rabbit hole.

Chris Sacca: This thing is Jim Crow, for sure. Then you just get caught in this spiral and now you're frozen out of the employment economy.

Michael Redd: That's right.

Chris Sacca: What are you going to do? You're probably going to get back into the criminal … It's just bad and yet 91% of people without access to that cash plead guilty. 54% of people who have access to bail end up having all their charges dismissed. Literally-

Michael Redd: Wow.

Chris Sacca: They have the bail. They show up and their charges are tossed out because we know a lot of charges are bullshit anyway. Then we've also seen a lot of data that show that bail doesn't actually get people to show up to court. They're either going to show up to court or they're not. In fact, a lot of states have eliminated bail and show up to court with the same frequency that they do in the states that … It's just bullshit. It is a punishment on the poorest people-

Michael Redd: That's exactly right.

Chris Sacca: People on the fringe and people who really want to do everything we can to keep them in the employment system, to keep them productive, to keep their records clean, to keep them earning. This is a funny thing. This is one issue where we and the Koch brothers agree. I think the Koch brothers are some of the most evil people on the planet. They created a lot of these political problems for us, but strangely enough, I gave a blurb to a book on prison reform, and right near my blurb was Charles Koch who is also-

Michael Redd: Wow.

Chris Sacca: Endorsing this book because they just realize prisons are expensive.

Michael Redd: Yes.

Chris Sacca: People falling out of the employment system are expensive. They end up on more public benefits. Crime rates go up. You want people to stay employed. These bail funds have been this really fascinating idea, it turns out. You contribute a bunch of money to a fund. That fund is administered by a small group of people who make it available, not as for-profit bail, but as nonprofit bail. They just put it up for whoever gets arrested. That person shows up to court. You get the bail money back and then you just keep recycling that money through.

Michael Redd: Wow.

Chris Sacca: With a couple of million dollars, you can serve hundreds of people.

Michael Redd: Absolutely.

Chris Sacca: Make sure those people have their bullshit charges dismissed and aren't caught up in a system and have their lives ruined, all just because they have access to this recycling pool of cash.

Michael Redd: Tat's powerful.

Chris Sacca: I think that pool of cash keeps 94% of its money every year. 6% of it is lost if people don't show up, but 94% sticks around.

Michael Redd: That's powerful.

Chris Sacca: That, to us, is a bold-

Michael Redd: Wow.

Chris Sacca: Scalable, crazy way to change the system. Now, what I'd like to do in the meantime is just eliminate cash bail in a lot of places. Luckily, some states are doing that. There are judges who are ruling it through unusual or unfair violation of Equal Protection Clause, but in the meantime, it's amazing to think okay, you can put the money up on a recycled basis and start to impact that. This woman, Robin Steinberger, who runs our organization is amazing. She's actually here in LA. That's an initiative that we think is just bold and crazy.

Michael Redd: Man. This journey has been incredible for you. What would you tell young Chris right now?

Chris Sacca: Young Chris? Oh God. Well, I would probably tell myself not to day trade. That definitely set me back a little bit. It just seemed like easy money at the time. That was good. I think one of the temptations we all have … By the way, I think my business, for the most part, when I look at parallels in sports, so much of it is managing your own psychology. You've made literally hundreds of thousands, maybe millions of shots over your lifetime of practicing and playing, and yet there are those moments where you psych yourself out, where LeBron is looking in your eyes. I got to know Kobe.

Michael Redd: I got some stories I wish I could-

Chris Sacca: I once asked Kobe, I was like, “Tell me about your trash talk.” I was like, “I've heard, you're one of the best trash talkers in the league.” I'm like, “What do you say to a guy to get in his head?” Kobe once told me, he's like, “Oh, I never talk about his playing.” That can actually rile some guys up if some guys respond to that. He's like, “I just try and make them question who they are as a person.” He's like, “Maybe who they are as a father or as a son, who they've let down, who they disappointed.” He's like, “I really try and make them question that stuff.” He's like, “That's when the wheels come off and I can just go crazy.” That was amazing to me, that insight. We're all humans. We all struggle with psychology. I think one of the things that I wish I could go back and undo a little bit for me was that.

Chris Sacca: When things would go right, I would give my personal skill or genius too much credit. When things went wrong, I considered it unlucky, and yet when I really go back and look, I have to reverse that. I think this is important for a lot of people to do, is that when things go right, recognize how much of that was timing, good fortune being in the right place, somebody else helping you out. When things go wrong, do a post-mortem analysis and figure out how you screwed that up, what your blind spot was, what you did. Look, when I made that $12 million day trading, it was literally in two stocks. I started putting my buddies in those stocks. By chance, I had picked the highest performing stocks in the NASDAQ in 1999, this telecom company.

Michael Redd: Wow.

Chris Sacca: Now, I found all these reasons why it wasn't an accident. I was like, “Well, it's a Latin American telecom. I speak Spanish. I spent some time in El Salvador doing telecom work. That must be why,” blah, blah, blah. Then when you get into it at 40 cents and it's trading for 40 bucks, suddenly, you're convinced the man when you put your buddies into it. My buddies from high school were like, “Dude, I just bought a boat. I'm putting a down payment on my cabin.” Buddies who were bartenders or limo drivers were feeding you. You get that all around you and you start to believe like, “I'm a genius. I got the gift.” Then when it all collapses so fast and you've got so much borrowed money on it, you lose millions of dollars. You're like, “Man, I just caught a bad market.” Instead, you have to turn that around.

Michael Redd: I agree.

Chris Sacca: Be like, “Wow. I was pretty damn lucky finding that stock. I took a lot of chances to get there. The reason I ended up $4 million in debt wasn't because the market fell apart. It was because I borrowed millions of dollars that I didn't have and left myself open to that crazy exposure. I think that's one of the things we often screw up on, is that we don't reverse that. When things are going right, we got to realize so much of that is coincidence. Not all of it. We put ourselves in that position, but-

Michael Redd: Sure.

Chris Sacca: Many things have to come together, but when things go wrong, we have to be honest with ourselves about why. you have to do an honest, humble inventory and learn from that mistake. I think that's something-

Michael Redd: It breaks the risk-taker.

Chris Sacca: The earlier I could have done that in my career, the better. The other thing that I feel like I've learned more, that I wrestle with every day is to write the angry email and then archive it. Don't send it. I do this exercise where I just write these absolutely incendiary … Look, in my business I still get-

Michael Redd: That's smart.

Chris Sacca: Absolutely F'd over all the time. I see people who make horrible decisions come at me. One of the things, as successful as I've been, I don't have a massive team. We're not an empire, so if you take me on, you're just taking me on. Some people still feel like they should do that. I constantly wrestled with … I can let that person know how horrible they are and the lowest esteem with which I hold them and how much they just F'd up. Or I can write that email. Archive it and now I have the information advantage. I know what they don't know. I still feel like I need to write it. I send it to my wife. I sent it to Clay and people on my team. I'm like, “We all read this. Okay. Put it away.” I could do more of that, but I don't know. I think that's advice I would give myself earlier on in my career, is people F you over. That's your information. Now you know how that person operates.

Michael Redd: What is next for you there? What mountain is there for you to climb next for you?

Chris Sacca: Some of it is turning out three amazing girls, continuing to grow. My relationship with crystal keeps getting better. One of the things I've been spending a lot of time on … People for a long time asked us, “Why don't you have a more diverse employee base at Lowercase?” Well, I think Lowercase, at its biggest, had five people, total. We've never been big. We never even had an office. If I had an office, that would've meant more meetings. I don't like meetings. I was just like, “Well, let's not have an office then.” In fact, by the way, when I was on Shark Tank, in the opening of the show, they shoot all these scenes and make you look really rich and powerful.

Michael Redd: True.

Chris Sacca: When it was time for the opening, they were like, “Okay. We're going to send a crew by your office.” I was like, “We don't have one.” They're like, “What do you mean? You don't have a place that says, “Lowercase Capital?”' I'm like, “Nope. I just always worked out at my house.” They are like, “What are we going to do?” They're like, “Okay. We'll shoot all your sports cars like we did with Robert.” I'm like, “We have a Tesla, two Teslas now, but one is the one we drive the kids to school and it's all car seats across.

Michael Redd: Private plane?

Chris Sacca: Yeah. I was like, “No. I don't have a plane with [inaudible 01:02:35] name on it.” They're like, “What about your boat?” I'm like, “I don't have a boat.” “A huge house?” I'm like, “My house isn't that big and I also don't want people to know where I live.” They're like, “Well, how is anyone going to believe you're rich?” I'm like, “I don't know. That's not really my problem. I've never tried to project that.” If you watch the show, they show me getting out of an Uber on the phone, looking all important. They show me raising a wine glass with a bunch of friends. That was at this random place in San Francisco at 8:30 in the morning. We all pretended to drink red wine. Then they show what's supposed to look like the Lowercase office. They put my logo on a screen that's projected. It's all my buddies cheersing me and fake laughing like I just said the funniest thing, all that to try and make me look wealthy.

Chris Sacca: Going back, I think really, my goal is to really try and raise some amazing kids and that takes work. I think this is a culture that has really tried to box girls in. Kids used to have a chance to just be kids. Now, everyone wants to just use them in pink in the princess industrial complex. Giving my girls a chance to just be kids. They love camo pants. They call them hiding pants. They love wearing their hiding pants with pigtails, I think just letting themselves express themselves without boxing them in. Keeping them away from the media that paints the idea that they're supposed to be helpless princesses. They have themselves decided they like science and engineering and making stuff and not because I told them to because we've given them the room to do that. My oldest daughter just asked if she could quit soccer to do rock climbing and I'm like, “Yes, you can.”

Michael Redd: Absolutely.

Chris Sacca: That sounds amazing. In fact, it really saves me Saturdays and Sundays, standing in a field with a bunch of people. That's one thing. Building a closer relationship with my wife, I think requires work. You've got to actively work on that. You got to talk. You got to admit vulnerabilities. It is active work. The same way you would do in a partnership and your job, I think you got to invest in that and when you do, everything's better. It's happier to build more and more trust.

Michael Redd: Absolutely.

Chris Sacca: That's something that I didn't realize upfront. I hadn't been in a relationship like that, how much you keep investing. It just pays off. Then I started talking about how our firm wasn't diverse. It was just never that big. Then I said too, “If we start hiring diverse people for the jobs here, they're just going to be junior people.” The idea I came up with years ago now, I don't know, five years ago, was to start investing in the next generation of new VCs. When I went to start my fund, I just wrote emails to all the rich people I'd ever met, even if we weren't close, just begging them for money to come into my fund. I was like, “A lot of people who are starting out in this industry don't have those same relationships already.”

Chris Sacca: They don't have rich people to hit up for money and they don't have people to vouch for them. They didn't go to those fancy schools by virtue of the privilege they didn't have. They might have gotten into Stanford, but who's going to pay for it? Yet I do believe they have unique perspectives on this industry and they know how to be helpful to companies. What I said was, “I can be the first investor in some of these funds and I can vouch for them. I'll put my own money in, our money, mine and Crystal's money.” Then I'll say to other investors, “Go in this one with me.”

Chris Sacca: “This person's special. I know they're going to do well.” Instead of hiring junior employees, let's help create the next generation of diverse employees. Instead of just paying attention to how the big venture funds of the world don't have a lot of black and female decision-makers, F it, let's go the route I did and make them not just working for somebody else, but giving them a shot at making the real money and making the real decisions and leading these firms. It's amazing. I don't know the latest tally, but it's 20 or, or more now. They're incredible firms. By the way, it's not charity. I'm going to make a lot of money doing this.

Michael Redd: Correct.

Chris Sacca: It's just giving a chance to these people who are overlooked by the system and by bias, by the implicit bias we have. That woman, Shivani, I was talking about earlier, is Shivani five feet tall? Maybe shorter. She's five feet tall, 90 pounds, Indian woman. I was at dinner with a speaker. I bring this up to reveal my bias. Don't think I'm judging somebody by this.

Michael Redd: No.

Chris Sacca: I was at dinner with a speaker at the TED conference. I wanted to sit at this one famous guy's table. I got there and his table was already full and everyone's laughing. I had total FOMO. I'm like, “Shit. Where do I sit?” I see this literally five-foot-tall, small Indian woman sitting alone with his name I didn't recognize. I was like, “Oh, this is going to be a wasted night.” I roll-up. I'm like, “Well, I should sit here, I'd be a jerk if I didn't.” I'm like, “Hey. I'm Chris. What's your name?” “Shiv.” “Shiv, what do you do?” Two hours later, I forgot to eat my meal. I didn't acknowledge anyone else that sat at the table. I was so engrossed by what she was doing and the world she was changing. At one point, I was like, “Who wrote all this code?” She's like, “I did.” I was like, “But you're not a computer science.” She's like, “Chris, it's not that hard. I taught myself.”

Michael Redd: Wow.

Chris Sacca: I was just like, “Oh my God. You're amazing. Who are you?” I would absolutely judge her by the package, by the presentation. She doesn't look-

Michael Redd: Sure.

Chris Sacca: We've got this president who hires because they look-

Michael Redd: polished.

Chris Sacca: Bullshit. Literally, she's making us a ton of money and it's turning out to be one of the most effective … No drama. Just execute, meet your goals. Incredible leader. Incredible culture CEOs we've ever had. Physically, I would have just looked past her because of this bias I wasn't even aware I had in me. I thought I was woke and I would have just looked right past her. By those coincidences, I end up in this amazing investment that we're super excited about.

Michael Redd: Wow.

Chris Sacca: I think making sure that this industry is represented by all these people. The way I always phrase it is you can do this either because you're a bleeding-heart liberal who believes that we've got to make up for hundreds of years of discrimination that persisted today. Women make 73 cents on the dollar. The system is rigged against these people right now. We all have this bias, admit it or not. Or you just do it because you want to get rich because the data are clear. Boards of Directors that are diverse with people of color and women outperform boards that aren't. Companies headed up by women right now and people of color are going into markets that aren't saturated by investment because it turns out women and other underrepresented minorities have incredible spending power and have not been the target of innovation. I'm sure there's a dozen Uber for yachts. Let's keep in mind you can go find-

Michael Redd: True.

Chris Sacca: A yacht for a few hours, but there are these startups being targeted more towards these communities that have been incredibly overlooked and it turns out they're making money. I try and say it, “Either you do it because it's the right thing to do. Even if you're like Scrooge McDuck and you don't give a shit, you're doing it because you have no allergy to money and you like getting rich and that's why you invest.” That's been a big area of focus for us. Criminal justice reform, making sure that we really are pushing, not just things on prison condition, but the idea of re-sentencing. We've seen this brain research. That your brain hasn't really stopped forming until 25. People just do dumb shit when they're 16, 17, 18.

Chris Sacca: We all do. It's just black kids who have cops on their blocks end up getting arrested for it and white kids don't. White kids get driven home by the cops to their parents, often. There's been incredible legislation passed in California, it's starting to show up in other places, that make people who committed a crime when they were under 25 and sentenced to life without the possibility of parole eligible for re-sentencing, to see if that really was a fair sentence, how they conducted themselves since being inside. That's incredible. It's putting people back into the position to have some control over their own destiny and lead a productive life. It's also having this downstream effect where guys in prison now are like, “There's a shot for me. Maybe I should make this productive time. Maybe I should learn, study and front my own wrongdoings-

Michael Redd: Prepare.

Chris Sacca: To my victims and be ready. That's some just incredible work. Stuff that's happening on job training for people who are coming out of prison, that's often a problem. You come out of prison. Now, you're a felon. Who wants to hire you? This group we work with called the ARC, the Anti-Recidivism Coalition, does this amazing work where they train guys to be electricians so when they come out of prison, they have union jobs, not just jobs, literally union jobs, high-paying, stable. They can come back in and be contributing members of society.

Michael Redd: Absolutely.

Chris Sacca: Provide for their family and have strong roots there and know that it's up to them to show up and work. If they want to do that, then they have a stable place in society again. It's beautiful. In fact, the next program that ARC is doing right now is teaching guys in prison to code.

Michael Redd: I love it.

Chris Sacca: They can come out and be a web developer-

Michael Redd: Absolutely.

Chris Sacca: This ops guy. Again, they've got guys coming out and making 80 grand because they've got skills now and that has this effect throughout the prison, like, “Whoa. What just happened there? Maybe I should get involved with that” because unfortunately, so many guys who get to prison, who weren't bad people in the first place, to survive in prison, they end up falling into some bad stuff.

Michael Redd: I wanted to say some of the smartest people in the world are people under bridges, to your point. I agree. The work you're doing is incredible, man. It's been an honor today to have you, man.

Chris Sacca: Oh, thank you.

Michael Redd: Seriously inspirational to a young angel investor myself. Thank you so much.

Chris Sacca: One thing I would say about angel investing, if we're not going to run out of tape, is always be honest with yourself in every deal. We have some rules. First of all, would we be proud to say we invested in this thing? There's things we could make money on, that we have not invested in like these vapes. I'm sure we could have made a ton of money investing in these vapes, but you get kids in school using these things, nicotine addiction. It turns out, the science shows, they're not really that much better than cigarettes and stuff. We could have gotten vape rich, but I don't have to tell my wife and daughters and parents, “How do we get rich? Oh, shit. Selling vapes.” No offense to the vape people, but that's the decision we made.

Michael Redd: Sure.

Chris Sacca: Number two is we only work with people who we feel make us feel better in our day, so basically, no a-holes that we work with. Three, we only hire people who have had crappy jobs, who have worked, studied, traveled abroad extensively, or have been exposed to the human condition in some way. We think it makes them grateful for every day. It makes them realize and contextualize what we're doing. It also helps them bring another lens. You can't build a product for a couple of billion people unless you know what people outside of your little bubble work like. We have a rule. Give yourself a chance to get rich. Don't invest in somebody that's already so high priced. Everything has to be perfect for it to work out. Get involved in something early enough that you actually get a chance to get rich.

Chris Sacca: Then the last and most important one is only invest in things where you know you can personally be helpful enough to help change the probability of the outcome. Otherwise, just throw darts at a board in the public markets, but you got to find stuff where you dive in. You see that product. You see that problem. You know I can change it. I can offer advice. I can bring other people in. I can help them tell that story. I can make the product better. I can steer the strategy here. I can help them sell this company or raise more money. Whatever it is, don't get involved with anything unless you're confident you can personally impact the outcome because that helps you get up in the morning and be like, “All right. I can work on this.” Otherwise, you feel helpless, anxious. Stuff starts spinning out of control. You're like, “I don't know what to do.”

Michael Redd: I totally agree with you, man.

Chris Sacca: That's what I see when people make the crossover from athletics, from entertainment, from other industries. When I see them try to come over, that's the part they fail at. They're like, “Oh, this is cool. I see a bunch of other people around the table.” That's no way. Chasing it … Sheep don't make any money in this business. Anyway, that's my 30 seconds of how to be a good angel. Thank you for having me today.

Michael Redd: Absolute privilege. It's hard to believe that this interview was a couple of years ago because there's so much here that's applicable right now. If you want to have success at anything, you need to be ready for the right opportunities, know how to have balance in your life, and discover how you can create impact and influence. This is just the beginning, folks. I have so many great guests lined up for this season, so get ready. Until next time, I'm Michael Redd. Remember you are the secret to your success.