♪ emily: he has been dubbed the "venture cowboy," not just for his signature shirts, but for his rash way of doing things . along with with bets on uber and instagram. he also wrote a $25,000 check to buy twitter. he amassed so many outside shares, he was the biggest outside investor by the time of the ipo. he recently made news by outlining his vision for the future of twitter, addressing the possibility that twitter cells to a bigger company like google or facebook. i sat down with billionaire

lowercase capital's chris sacca just days before twitter's ceo dick costolo announced he was stepping down. thank you so much for being here. emily: it's cool -- chris sacca: it's cool to be here. emily: i hope you don't mind me calling you brash. chris sacca: that's probably accurate. emily: you just released a 8500 word missive about twitter. about what twitter can be. before we cut to a medicare sponsored scooter, what is twitter's future? chris sacca: 8500 words sounds like a term paper. i have been invested in twitter since the first time anyone could invest in twitter. i have been a user since 2006. i have been obsessed. it is part of my business. there have been more than one billion people who have tried it and not stuck around. twitter needs to be easier and more exciting and less intimidating for these people. emily: what has been the reaction from twitter? have you heard from dick? chris sacca: no, i haven't heard from dick since i posted that. to be clear, i don't talk to dick that frequently anyway. i mean, we are pals, so it is

not out of the ordinary for me to not hear from him. i talked to a bunch of other people at the company. it was a well received post that i think, done right, sets them up for success. it points wall street in the direction of, this is how you should be evaluating the company. you should not be headhunting the ceo, you should be focusing on these things. if they execute all of the stuff that i laid out, no one would be asking the question of if dick costolo should be ceo anymore. emily: what should twitter do? what is the problem? chris sacca: right now, it is scary to tweet. and when you do, it feels kind of lonely. they need to do a better job if -- of making it the kind of place where if you don't do a lot of work, you can follow tweets related to the game, the election, the protest. time for the heart. emily: you want a heart? instead of a star? chris sacca: you use paris goats. the endless stream of hearts is amazing. emily: the hearts do make you feel good. chris sacca: it makes you feel it knowledged, heard, valued.

but "favorite," it is like, is this really one of my favorite posts? for most people, they don't do it. emily: dick costolo was on the show and he said twitter is the very best way to connect to what is happening in your world. i'm very confident that that is what twitter is, and everyone at the company is confident that this is what twitter is. is that enough for you? chris sacca: mission statements and taglines usually leave most people feeling empty-handed and directionless. it is a complex product that has to appeal to myriad audiences. to use it for many different reasons. i don't think a single tagline is going to do it. emily: you have been waving the pom-pom for nine years. you have your house painted aqua? is that true? chris sacca: we have a twitter blue room in the house. twitter has been good to me over the years. emily: why now? chris sacca: why speak up about this stuff? because i think we have the right team. i think dick finally has his squad. emily: why do this publicly?

why didn't you pick up the phone and email them? chris sacca: i have. i wanted to take a shot at doing it externally. the audience important for me was those working at the company, not just senior management who have been working there a long time that are just, "yes, yes, yes." if the company starts delivering on it, i think everybody wins. emily: you are not an engineer, you're not a product guy. why should they listen to you? chris sacca: good question. i do not know. i have a track record that has worked out well. uber, kickstarter, gawker, i would like to think 1 or 2 of these things might be lucky, but it is probably not an accident, at scale. at the same time, i think you have to trust your own intuition as a person. i think one of the most interesting challenges in silicon valley is that the people who are not your users do not have any voice. that is one of the challenges all of these companies need to start incorporating. this is going to be a company that has the potential to be bigger and more meaningful than a facebook. if dick executes on this stuff,

then that is the ceo of this company. emily: have you talked to the founders? i know you're close to ev. chris sacca: i have not talked to jack recently. i did bump into evan in the studio. many of those things were things that were not my original ideas at all, but ev and i have discussed while he was working there and are things that i believe would be worth doing. the future ishares not five-year vision of twitter, it is where's they should be now. they have lost years and they are just playing catch-up. emily: google buying twitter. is that realistic? chris sacca: it is really realistic. emily: but speculation has been going on about this for years. chris sacca: if google were to buy twitter, it would instantly improve the stuff google has. this board, there is no one that wants to be independent forever. there is nobody owns 50% of the stock or could block a deal like that. emily: you think google would want to buy twitter?

chris sacca: i think google would love to buy twitter. i think they never got social personal identity, real time, or anything, they haven't nailed that. that said, zuck would not let twitter go to google without putting in a bid. there's just no way. zach looks at twitter and see so -- sees so much potential in it. people i know who are close to him -- i'm not close to him, but his perception that twitter is not doing everything they could has not changed. he would love the opportunity to own it and to improve some of the things. you have a user at microsoft who has watched it. back when we did the search monetization deals when twitter first started selling some of its search data to partners. when microsoft negotiated that deal, he was across from me and dick costolo. i think alibaba may be interested, too. emily: you think facebook,

microsoft, alibaba, all want to buy twitter? chris: all those companies would benefit strategically. all of those companies would explain to their shareholders why they would pay a lot of money for it. it would fit into their companies without blowing out or competing with something. emily: what about apple? chris sacca: i do not think apple cares. i do not think it is in their bones. i do not think they don't care enough. particularly with apple, i think they go in a different direction. they don't care as much about the human or social elements. i just want to be clear about this, though -- i don't think twitter should sell to them. there is literally unlimited potential in what twitter can continue to build to get to 100 million more people. if they do that, the stock will be trading in the 70's, 80's, and 90's. that is why i am not campaigning privately or publicly for it to be sold. if the board stops believing that at any point, i don't see anybody on the board that would block that sale. to someone who think they can do a better job of it. i think sometimes when the founder is still running the

company, people just defer to their judgment. i think you are allowed to be weirder and a bit more eccentric. people are just like oh, that guy, he is in the future. i think because dick doesn't have the benefit of being the founder people don't give him , that benefit of the doubt by default. emily: what if some of the things you suggest don't happen? chris sacca: if they do not happen, the company will just go sideways. the stock will go sideways, there will be more distraction, more people calling for management heads, it will be hard to land the talented people they want to work there. user growth is accelerating, -- if these things are not working, they should give the company to someone who can do better with. emily: do you have a preference among those? as an investor? chris sacca: no. if this company has to sell to others, that is a letdown to me. when facebook tried to acquire twitter, jack went down to a meeting with zuckerberg. when they came out of the meeting, they called dick and i for advice. we happened to be in hawaii. we are there on speakerphone listening to the facebook offer,

and to decide whether or not to take it. there was not any wavering about whether this was going to be an independent company. those guys always knew it was going to be huge. they have always been a couple steps ahead of us and how big it would be. emily: do you want something more here? do you want to be a board member? chris sacca: no, they get my help for free when they want it. emily: do you want to be ceo? chris sacca: jesus. i don't want a "job" job. [laughter] no, i like what i do for a living. we have over 100 investments now. lowercase capital consists of 3 people. we are one of the biggest funds in terms of money under management we are only three people. we don't have office space. my coo works out of the back of a winery that she runs. my partner is in la, working on planes moving from portfolio company to portfolio company. i don't really have an assistant. emily: how big do you think uber can be? chris sacca: that is truly limitless. ♪ emily: what is the myth of

chris sacca and what is the reality? chris sacca: i never followed the step-by-step path you're supposed to do to do this. i had no business being a venture investor. i had no business quitting my job at google. unlike, i'm going to strike out on my own, google is getting pretty big. it was becoming bureaucratic. i am not good at playing company politics. you know who was was sundar, i knew that this guy was going places. emily: he has obviously done quite well. chris sacca: yes. he will be the ceo of google someday. it was just obvious back in the day that he would do that. emily: what do you think of how he is leading google now? chris sacca: sundar is an incredible compliment to larry. i use that as a foil, because we sit in the same meetings. he is brilliant, we both have good ideas, but god he can , actually navigate a big company, and i can't. i have short elbows, i have strong opinions, i'm impatient in ways that i think are more similar to elon than sundar. emily: in what way? chris sacca: tough to work with. i demand everything to be exactly right.

i grew up with just my parents' excellence where it was expected. it was not even demanded. we would do everything right the first time. emily: at google, you were described as this guy who maybe would go to meetings and get stuff done and might have rubbed people wrong way. how do you feel about that portrayal? chris sacca: it was accurate. fors protected on high [beep] guy who got done. that said, he did not fit into the hierarchy. i totally know why it rubbed some people the wrong way, but i stand by the stuff i did to get stuff done. emily: what do you think about the moon shot? is that what they should be concentrating on right now? chris sacca: yeah, i do. self driving cars is a small idea and it will not pan out. that could be worth more than all of google is today. the stuff they are doing in health to change the world forever. the stuff they are doing in

robotics could change everything. where they have dropped the ball is the stuff that is incremental from where they are right now. it is a bummer that youtube is not more social. the comments there are a disaster. emily: what about facebook? chris sacca: i've no doubt about facebook's ability to maintain its ability to reinvent itself. they have used their market capital to buy the coolest stuff. zuckerberg knows what he's -- he knows how to execute on that stuff really quickly. he was on top of instagram and he knows how to close out that deal. emily: do you think kevin sold too early? chris sacca: kevin walked away from that deal. at the time it was signed was about $300 million to $400 million, which is probably worth around $600 million to $800 million now. if you would tell me you wouldn't treat everything you have right now for $800 million. emily: could he have more? chris sacca: i am sure he could have had more. but he could have zero too. i do not think it is any of our place to question a guy like that. he has the best of all worlds. he sold the company, made a ton of money, and now he has been

left alone to continue to execute on what he's wanted to do. kevin has had an amazing life. he is dj-ing in vegas. i've never seen anyone dress better than that guy. he's got his finger on the pulse. he drinks the best bourbon. he goes to fashion week in paris and everybody falls all over him for how he has changed the world of fashion. i don't feel bad for kevin one bit. emily: what about snapchat? here to stay, or just a fad? chris sacca: snapchat is very real. those guys came up to me after an event i did once and they said they were big fans, we would like to sit down. i first, i did not understand it. i was like, is this a dick pic thing? i passed on dropbox, i passed on airbnb. at google, i told eric not to invest in go pro. each of these times, i focused so much on the negative case that i missed all of the positive case. airbnb founders, i said guys, this is dangerous. i think somebody might get raped or murdered while they are

staying at someone's house and the blood will be on your hands, and i said this out loud to the guy. they now have a $20 billion company on their hands. emily: you didn't pass on uber. chris sacca: no, i didn't. emily: and you own 4% of the of the company. chris sacca: i was lucky to be one of the very first investors. i had deep convictions about what could be. emily: you don't think uber has used very dirty tactics? chris sacca: i don't. i think they have used aggressive tactics. emily: how big do you think uber can be? chris sacca: that is truly limitless. i do not think it is worth less than $200 billion by the time it goes public. they are nailing down the food business. that's a whole other business. emily: taking on fedex, is that some think they would do? chris sacca: they are delivering packages in hong kong right now. that is a cool company shift. i did not invest in it because i think it is likely that is something uber will likely do. i don't own instacart stock because i think it is something uber will do. i think travis's ambition is

boundless, but i think his ability to execute on that is unlimited. emily: you mentioned your hot tub in truckee. travis is the unofficial near there. you are very close but you do not talk anymore. why not? chris sacca: i think travis has a personality like mine. we have strong opinions. if i am involved in your business, i will share my opinions about how aspects are going. they will be very strong opinions, likely in your face. i think we rub each other -- we have a different way of doing it. i think i can rub people the wrong way. it can be pretty mutual. in particular, i wanted to own more uber stock. so at the time, i was trying to buy it from more people, and travis didn't like that. i think that scratches the surface of more tension that was between us already. emily: have you tried to mend the fence? chris sacca: working together professionally for now is kind of the best way for us to get along. what can i do for uber, that is a good way for us to collaborate for now. emily: what is the craziest thing that has happened in the

jam tub? chris sacca: the only thing crazy that happened is travis can stay eight to 10 hours in a hot time. normal people cannot do that. emily: you think lyft is gone? chris sacca: lift doesn't survive this. ♪

emily: what do you think is going on right now in silicon valley? we have seen unicorn valuations -- chris sacca: decca corn.

emily: decacorn. chris sacca: you know the culture secrecy we have here in silicon valley where you don't tell people your numbers or business model, you don't tell them about the future. emily: isn't that dangerous? chris sacca: it is really dangerous. the story of founders living lavish lives and investors doing really well is attracting more attention and more posers, and with that attention comes sloppy discipline and a ton of money. think about the early days at y combinator. 12 companies, demo day lasted all day. live code, we could ask questions, walk up and try it during demo day. if the deal didn't get done that day, we could work on it. demo day today, what is it, 80 companies a class? 450 investors. 3 minutes, no live code, and those deals, half of them are dying before they even present it demo day. i think it speaks to a desperation on behalf of investors to be a part of this game. some are taking money away from companies that should probably use that money. they are taking talent away from companies that could use that talent. they are taking investor and advisor attention away. i think there is a lot of waste happening in the valley right now. some of these valuations and the accessibility of capital is just bananas. it is an amazingly rigged game, the investing game.

where it all comes together is, i don't think the public market will hold up forever. i do not think the global economy will support the market being open. by the end of this year, the public market basically closes down for anything with quality lower than an uber, frankly. emily: what do you mean by that? chris sacca: you have a bunch of companies sitting around with no exit path. there will be down rounds. emily: you think by the end of the year, the tide will turn? chris: yes. the market is up, and so -- i think there will be some pain out here for the companies themselves. emily: what happens to all of these unicorns and decacorns? how many of these are horses masquerading? chris sacca: i think there are naive investors with no discipline throwing out term sheets with nine figures with no diligence. give you an example -- icon investing in lyft is publicly stated rationale. if uber is worth 40 or 50, then lyft must be worth two. if you really look at this thing, it will not be a tourist race. lyft will not survive and travis will never buy it. lyft goes away. emily: you think lyft is gone?

chris sacca: lyft doesn't survive this. uber is a better company with better math, better predicted supply, better brand, lower pickup times, higher quality of service. emily: you are an uber investor. chris sacca: i am a huge one and i would be a bigger investor on that service alone. -- that thesis alone. i would never buy lyft shares, because i don't think they are going to could -- going to be able to compete. emily: so icahn made a big mistake. chris sacca: he made a big mistake. this is a win or take all game. and travis will take all. emily: will there be a downturn? chris sacca: and silicon valley. emily: yes. chris sacca: yes. it is inevitable that the funders putting this money to work will not see it all back. emily: are we in a bubble? is the bubble going to pop? chris sacca: there are multiple ways to define that. emily: yes or no? chris sacca: yes, some companies are going to go away. 2000 and where you can't get a -- it is going to be like the year 2000, when you cannot get a u-haul because they have all

gone one way out of town -- no, because this is the epicenter of innovation, just out of whack right now. emily: what you think is the biggest problem in silicon valley that is not being talked about now? chris sacca: there is nobody normal left here now. all of the normal, regular people have been priced out. the artists cannot live here anymore. the musicians cannot live here . you don't even need nurses, or doctors, frankly, who can't afford this city. that is messed up. i think the biggest problem here is computer science programs are so lucrative now the kids do not need to pay money to go to them. they don't need to get jobs, so they have never waited tables or parked cars, now we have a generation of software engineers working at these companies who have very little compassion. we have an increasingly limited worldview that is really out of touch with how the rest of the world lives. i would like to see more people get the hell out of here and be around real people every now and then. we do not have anyone here who represents the voice of the normals and they are not even

our neighbors anymore. emily: chris sacca, thanks so much for joining us. it is been great to have you. chris sacca: right on. ♪ announcer: from our studios in

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