Chris Sacca Interview (Full Episode) | The Tim Ferriss Show (Podcast)

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killers and hundred dollar bills this is Tim Ferriss and welcome to another episode of the Tim Ferriss show I've had a lot of whey protein I've had a lot of supplementation BCAAs few other goodies like synthetic ketones and I'm raring and roaring to go with this episode so I don't want to give you too long of a preload but if you haven't joined me before on the Tim Ferriss show this entire program is about deconstructing excellence it is about interviewing world-class performers the best at what they do to identify the rituals routines influences books tips and tools and so on that you can use so borrowing best practices from the best in the world in this episode we have a very fun guest he is widely requested and now he's here Chris Sacca or Chris Sacca depending on how you say his name he was recently on the cover of Forbes magazine their Midas issue and the title says venture cowboy the 39 year old behind uber Twitter and Instagram might be the best angel ever so why all the bad blood and burn two bridges and then the article if you look inside is titled how super angel Chris Sacca made billions burned bridges and crafted the best seed portfolio ever I have known Chris for quite some time and I've mentioned before that in the game of early stage investing I've learned a ton from a lot of people but three people stand out immediately Mike maples jr. and then Chris Sacca and Navarro account those are three who have been very very generous at their time and this episode is wide-ranging it's not just about investing it is about life design it is about career decisions and much much more so please enjoy my conversation with Chris Sacca Chris my fans have demanded it people have asked far and wide for you to be on the show so thanks for cutting out some time in this spectacular trip mom's like you're here we're uh we're on Necker Island in the British Virgin Islands my first time to the BVI it is paradise not too surprisingly and for people who don't have much context on you number one is its akka or Sokka that's totally regional I'm from I'm from near Buffalo New York so it's c-anca it's very nasally you got to get it right then to see it I'm Chris Sacca hey you guys you guys so do you introduce yourself a second I don't know let's see what's your name Chris you know I'm more of focused on spelling it sounds like what the hell something I guess ACCA but I guess it's SACA Chris Sacca sac out comes off my sac all right cool and you grew up like you said on the East Coast uh but let's let's do a quick not entire retrospective but to give people the present tense what are you best known for aside from professionally or personally uh both aside from that were amazing my wife all three so professionally I'm known for being a venture capitalist an angel investor turned venture capitalist and I was one of the first investors in Twitter one of the first investors in uber Instagram Kickstarter docker Optimizely lookout Twilio just going at my unicorns so you have you have this this sort of unicorn radar and the uu of course had the angel investing experience and then you had your fund experience can you tell people a little bit about how that has gone for you in terms of in terms of managing my funds you're first you're just here for your first fund I would say that is one of the reasons why you were just recently on the cover of Forbes magazine you know horrifyingly Godin t-shirt we can talk about the shirt no so our first fund is turning out - it looks like it might be the most successful fund in the history of venture capital we had Twitter in there we had Hoover in their instagrams and their docker still in their Optimizely still in there we had some very cool stuff like Zen coder was in there so we've had some good deals that have gotten bought along the way but it's it's it's it's just taken off like there's no like no fund has ever done in and you know right now it's I don't think Ober has done growing and so it certainly hopes that yeah so we're at where it's somewhere around 250 X multiple on the funds that's amazing and I want to I'll start off some people have followed our friendship over the years the heckling on the endless heckling on Twitter and like I I mean no it's I'm very sincere and authentic when I asked when you and and Kevin Rose are gonna release the podcast episode where you guys make out and Kevin told me that was behind the paywall it's the bonus resting behind the paywall and i think we have to wait until there's a slump in our careers and I give that in your back pocket Poehler Kardashian reinvent ourselves but the the gratitude I want to express first before we get into things is multifold so some people have read the 4-hour body might recall that I mentioned you in that book for introducing me to do Total Immersion which was I think the first time we ever met you brought it up this is that the was that the the barbecue that that caterer has actually threw outside the department and you said something along the lines of when I described how how bad I was at swimming and pretty much incapable of swimming he said I have the answer to your prayers that's a great response which ended up being accurate in this case and his total immersion swimming so I learned to swim for the first time properly in my 30s using that method so thank you for that and also since the early days have been a very open book when it came to talking to you about investing and advising and of course the the legal notepad has been now transcribed into Evernote so I have many Saka files that are all very favorable but how did you what were some of your formative experiences growing up well let me let me just talk to what you were just saying in terms of being generous with the I mean first of all the Total Immersion thing is like a religion when you get it you get it right and I went from dragging my ass around the pool just kicking too hard and paddling too hard to when total immersion at me I could suddenly swim a couple miles and get bored and so I was just there as an apostle man when you were like I'm struggling with swimming that was I was just geeking out in the same way you can get going on lifting techniques and stuff like that I'm like you're in my world now and I'm going to talk about swimming but the same with the investing stuff I mean I was really lucky when it came time for me to get started as an investor I had many many guys they're paying it forward and teaching me about the game guys like Josh compliment at first round Tony Conrad at true ventures really being generous to their time and helping me figure out what was going on the guys at industry ventures were indispensable for me Hans wilden's and his team and so and so for me when you came along and started asking questions about that not only I feel like I was paying it forward again but in the same way you and I never invest in a simple idea the execution is everything I don't feel like I'm really giving any secret away by telling you what the approach is you still have to go execute on it right so I can give you my lens on how I think about this stuff things other people have taught me things I think I might have improved upon etc but I can I can lay that playbook on you and if you're not good at this you can't fake it right and so I don't have any fear in kind of disclosing my secrets to B teamers because they're not going to end up competing with me in your case you're good at it and so it's become an incredible side business for you in addition to everything you do you know with media but I but there's no fear and in putting that stuff out there and the other lesson they taught me is that if I get to you and teach you some of this stuff you're going to naturally be an ally of mine in this industry so if I can get in there and kind of teach you how do I think about the world how can I be helpful to companies and you start using that same method then we're going to end up doing deals together and you and I have and we've made a fair amount of money doing that and so so I didn't I don't want to leave that unanswered well it's it's really been fun to watch you sort of evolve and grow an experiment also in investing and just coming back you know we can we can rewind the clock back to your upbringing a little bit later on but just since we're on the topic what were what were some of the pieces of advice that you were given by say the guys that you mentioned or other people early on that helped you to approach early stage investing in a more intelligent way yeah I mean a couple of guys have said things that I've now taken an amalgam and have codified so I have rules for investing now that we're definitely influenced by a lot of these guys give me advice and things that I've now put to work so one is only get involved in deals Ryan oh I can personally impact the outcome now there's no guarantee that I can take it from you know X to sold or X to IPO but I need to know that I can have a material impact to make something that's to make something more likely to succeed so the second role I've developed and this again influenced by guys along the way we've given me advice is start with something that's already great that you can make up more awesome you know but don't start with something shitty that you think you can make good and that's hard like when you work in a company and a lot of your listeners I know work in big company you have to work on the [ __ ] that somebody hands you right so you're just dealt or really your Delta 2:7 and like well okay that's what the boss gave me I got to play this handout when you get into investing your default stance should be no because most deals suck most deals won't make money most companies will fail and the temptation always is you see your first deal and you're like okay I can know I can be helpful with these guys I know I can make this shitty thing better and so your first few deals are always the worst it's how I lost yeah fifty grand my first deal and I was just like oh it's like four twenty five percent of what I had hypothetically allocated right through two years it's like oh my god no that's because you get in that room and you're like okay I know how I can make this thing better right and you forget that you need to start from something that's already independently pretty damn good and then make it better so our third principle is is give yourself a chance to get rich and that was something that was influenced more by lottie's fund investors for like hey it's all well and good to throw 25k around into some of these deals but most of them won't be home runs most of them won't turn into unicorns most of them are gonna require a ton of work a bunch of those will fail but a bunch of them will be successful the tune of of doubling that money but over years and years of work and so I've sold companies I sold a company to Amazon where I saw 3x on a $50,000 investment in a fund by the time my fund got paid back and I got my part back and I was had been busting my ass in that company for a couple years like I barely had money left to buy the guy's dinner and to celebrate the deal and so so that's another thing is leaving ourselves enough room to benefit from scale going in at prices that are low enough that if the company is successful as we think it's going to be we've given ourselves a chance to get rich and then the fourth thing that I think we evolved internally or that I involved was just be proud of every deal there's stuff that I've passed on that I just don't regret it at all it seemed like maybe a good way to make money but I don't have to explain to my kids that's how I made money and so so those are kind of the guiding principle I shake categorically what would some of those be I'll you know mistyped domains right so that's a great way to make money people are stupid and they miss type stuff all the time and you can put ads on sites that don't really look like ads subscription businesses that make it impossible for you to get your to cancel your subscription I never forced ya you can sign out and yeah you can sign up online but you need to send them a postcard you know to cancel like that kind of stuff I see that stuff right you know people making up Stan sheets unsubstantiated claims about the effectiveness of their stuff you know this this this anonymous content stuff that just it was just going in bad places so I just want to be really proud of our deals and so those I think are some principles that have been shaped by a lot of these guys give me advice along the way what are when you've meet with founders for the first time what are is there anything that disqualifies them quickly are there certain sort of red flags that you look for yeah so this this has evolved over time you know I've now been doing this for awhile and I've done in over 100 deals and have seen a bunch of those work out and I've seen a bunch of not work out and I read all the posts that my peers in the industry write other VCS I you know everyone's constantly stabbing at hey what is the rule like how DS how do you get into one of these meetings so let me first have a couple parameters one is I almost only invest in things that are already live in production just no hypotheticals no ideas I think there might be one exception to that and it was a particularly gifted entrepreneur that I already worked with before but other than that we look for stuff that is that is already actually being you know has users that has that that can demonstrate that the team is capable of building and launching stuff together and getting it out there in the market but that said then the one thing that will turn me off right now is if I see that in the pitch the founder is trying to convince themself if I can pick up on any hint that that they don't in their like in their marrow believe in this story then it's no dice as I look at all the most successful founders I've backed the thing they have is inevitability of success there are no conditional statements coming out of their mouths there's no like well if it works it would be rad instead it's just always you talked to Kevin system and Instagram when he was working on it himself he was literally a soul guy working on the product and he's like so when we get to 50 million users will roll out this other stuff and you're just like wait what he's just peering into the future kind of looking through you into something in the future and you're just like I got to get along for the ride with this guy the same thing you talked to Evan Williams when it comes to talking about the likelihood of success of his products he just knows like he just knew Twitter would be a big thing he knows medium will be a big thing he doesn't need to convince you of that right now he just knows you talked to Patrick and John Collison it's stripe and of course they're building for this thing to be a big dominant company and it just will be you've spent time with Travis you're an investor in uber was there any doubt at any time that uber would dominate the planet there's no there's no doubt can you can you just share it there's an anecdote I think we probably talked about over drinks at some point but the Wii tennis Wii tennis could you have a Scooby Tennis yeah could you tell the snow it's a few years ago we're up in my house and you know we live up in the mountains in Truckee and it was over the holidays so my parents were there I think it was actually New Year's Day so Travis and I had been we have a tradition up there on New Year's Eve we go snowshoeing at midnight and drink champagne out in the meadow and stuff so I think we were pretty it's pretty rough morning but Travis sitting on a couch and my dad sent us some weakness and he challenges into a game of Wii tennis so on the Nintendo Wii my dad's not a bad player he's pretty good so they tryouts like okay mr. sacker sure and he picks up the controller and they play the first couple of games and they're tight games with Travis wins them and my dad is there taking like full swings with the paddle you know it's like breaking a little sweat Travis is still blurry from the night before barely breaking his wrist and he's beating my dad way I was like what the hell is this and then there was that inigo montoya moment Princess Bride salaries the Travis turns my dad and says I'm sorry but I'm not left-handed or you know I forget if it's left or right but he switched his hands of the controller the next three games my dad never touches the ball there were no points scored on any of Travis's Serbs I was like what the hell is going on like what is this and after the torture got to be too much Travis just says let me take you to the global leaderboard I'm sorry I got you know I'm stuck I don't mean to be holding out and he goes to the global leader port and Travis kalanick was ranked number two in the world at Wii tennis in his spare time now over was already a thing and like that literally he was already building a startup but he's just so obsessive so competitive and that's the thing as we look across the portfolio at all the most kick-ass companies that's something they just have right up front is is that they're not hoping and praying for success they know what's going to happen now on that note though it's so - pull pull out - two names for instance you have an Evan Williams blogger Twitter BDM etc then you have Travis personality-wise at least from the outside looking and very different personality types and I bump into some investors to say well I only invest in merciless sort of off highly offensive offensive meaning not defensive CEOs than other people are like no I I only invest in people who like I would watch my kids or whatever it might be but what are the commonalities or are there commonalities when you look across these founders for whom success and massive scale just seems predestined what are the commonalities well I think it's something so we'll we'll take Evan Travis examples but but across our most successful founders you know let's use a map Matt Mullenweg for us that's a that's a billion-dollar company an out billion plus these guys are all incredible incredible listeners so when they do open their mouths it can be bombastic and offensive and aggressive and in-your-face but they're all incredible listeners and I don't just mean in casual conversation I mean these guys go out of their way to interview other people they really if you catch a v' he's got a notebook always and if you ask him to see if you're you know last few pages of the notebook he's just meeting with other people who's you know billionaires and and kind of leaders whose jobs might not overlap with his at all but from whom he's learning voracious reader part of why mediums started was he was really back deep in the long-form content when he took a break from Twitter and so that guy is just constantly learning studying studying and so when he speaks it matters but he's listening more than he speaks you know that about Mullenweg one of the most thoughtful people I've never seen anyone read as many books as that guy does and retain all the knowledge Olympic and he also it's a bean he listens to anyone that he's sitting down with mm-hmm doesn't matter if it's you know the the waitress or a primary school teacher we've done a lot of traveling together he was on the podcast also very good listener yeah and so and again you just look across the board these guys are learning they're modeling they're constantly researching they're gathering data you know Travis would think it a competitive disadvantage for you to know exactly what's going on in his head sometimes so he'll listen and and it's an amazing town I think Drew is is a commonality across those people with the the investing game that you've obviously been a participant in for quite a while now you have to say no a lot and I was you know took a close look at at poker in the last year with the TV show and there are a couple of quotes that came up quite a bit along the lines of you know I made my money sitting not playing hands and but but that having been said what are some of the deals the the whales that got away yeah so first of all I mean this is a rigged game right man and I'm just looking to make it even more rigged so for those who don't know venture capital I mean it's totally unfair people give me their money I draw a management fee off it so they pay me to take their money and invest it for them if I make money then I pay them back the management fee and then after that we split the profits and I get a really big chunk of the profits and if I lose money that's fine it doesn't come out of my pocket I keep my fee and my investors lose money that's how this industry works that's bananas right and at some point it's gonna break because it's you've also incepted me with the term bananas which I've started using compulsively in a CEO also has done the same thing it works with yeah it's it's just an unforgivably unfair rigged game that's in favor of the venture capitalist and so so that the reality is the risk of an investor doesn't begin to compare to the risk of a founder and so you know that's one thing it kind of drives me crazy sometimes about some investors and I love the entrepreneurial spirit that goes into building a firm I mean I built my firm from scratch and there's certainly founder type lessons in there but but your cashflow positive from day one when you start a venture fund and your your downside is incredibly limited by the structure the fund so so that said what it allows me to do is place some bets on some stuff that I I'd like to think success is inevitable those things but I can take I can look at the risk analysis and say okay it's a binary outcome a one or a zero and some of those things just don't get there you know one of my one of my kind of constant recurring nightmares about the stuff I passed on no that's exactly that's what I was that's what I was trying to ask you know I've done some deals where I thought it was gonna be a lot bigger and you know it ends up going away but so the Dropbox guys I met those guys very early on while they're still in my Combinator I got an early look you know I had an opportunity to the deal and I pulled those guys that said I was like hey look at Google we were using a version of this called platypus which became g-drive and they're gonna crush you guys man so you should probably find some other product to pivot to probably cause hundreds of millions of dollars the they give you a pat on the head and oh yeah no I mean it's when I see drew the CEO Dropbox I bring it up before he can that's this yeah I just get I get it out there right away the Airbnb guys I why commenter same thing right business an amazing business and wanted to be proud of - I mean that's I'm really jealous I'm not in that business not just for the money but I love what they do I'm really admire them a lot and their culture but at the time they were they were allowing you to rent out a room in somebody's house while the owner was still there and that just seemed really scary to me and I pulled the guys aside I was just like guys you know somebody's gonna get raped or murdered in one of these houses and the blood is gonna be on your hands I've literally saw that out loud to them hey what's that worth like fifteen or twenty billion now now in fairness you you're probably not wrong right I'm in at a certain scale at scale it has to happen it's gonna yeah yeah I mean I like to say sometimes like when you think about scale like someone who works at Walmart murdered someone last night right there's just no doubt about it at that scale with a few million employees one of them murdered somebody last night you have to look at it like Edward Norton in Fight Club like an actuarial analysis yeah for insurance which is terrifying but that's the reality of big numbers um but maybe but there's no outside so there's one other famous one there's a bunch of these but actually I'll give you two Nick because I wasn't remind us until recently Nick Woodman from GoPro came to Google now I wasn't an investor at the time but I did a lot of Google's investments and partnerships and so Eric Schmidt CEO Google said hey will you come in here and sit with this pitch you know he's a friend of a friend said we got to meet this guy so Woodman comes in with GoPro and Eric's like I don't know and I was like we'd be we'd be foolish to do this deal how's this guy from Santa Cruz gonna compete with all these Asians and building hardware you know you can't you can't hold a candle like the Taiwanese and the Koreans was like no dice man let this guy go and I think I introduced into somebody over YouTube just as a consolation I saw that dude this winter skiing he's worth like three or four billion dollars now and he didn't forget that meeting so and then the snapchat guys I gave a talk in LA and they came up to me I never met them before they came up after the talk and said we're big fans we'd really like to work with you and I was like yeah sure I mean I know you guys were up to something cool I admire it I took like eight weeks to set up the meeting and by then the benchmark guys had done that deal yeah that's okay oh my god I can't imagine how much money we've left on the table as a result of that so you know I'm I like to say when I'm wrong I'm wrong when I'm right I'm really really right and the question on being wrong though I'm very curious about this and just coming back to kind of the poker analysis or analogy rather the and I actually heard about this at in depth in at first when I became friends with some hedge fund managers and they really try to focus on good process and not conflating say bad outcomes with that process in other words you know did I make the right decision at the time even if I missed out on a huge opportunity because you can also say pick a company for the wrong reasons and have a fantastic outcome but over time if you develop bad habits it can really screw you right so do you do you think that you made the wrong decision with those companies in terms of the analysis of the process that you followed or did you make the right decision based on your rules you've set up for yourself and you just missed out on a few opportunities but also hit some homeruns the one thing that all those failures to invest that they all have in common is that I let the negative case dominate my analysis of whether I should invest or not so in the beginning in the in as a seed stage investor you don't really get a lot of data right right we don't have any financials to look at the team usually consists of three to five people there's some users but not enough at scale they're usually just the early adopter so you don't know whether it's gonna be a big thing yet so you don't have a massive diligence process and so a lot of what you're going on is your gut about this product and about this team and I think the easiest way to screw this up is to let the negative case dominate your perspective so Dropbox I'm thinking about the competitive landscape and I'm thinking okay Google's gonna crush them well first of all we've seen that didn't actually happen and rarely does the incumbent crush anybody it's just not that common a start-up is going to move much faster than a division of a company where it's not their bread and butter I mean g-drive spent three years in beta you know internal beta etc it was never really a priority for them so course Dropbox is gonna win that you know I look at Airbnb yes there's gonna be bad things that happen like people get their apartments trashed you know from time to time but somehow I let that distract me from the potential for this worldwide marketplace for space that was just going to displace hotels with snapchat I'm thinking about dick pics and you know how it's being used by that was on the pro side yeah exactly like hey but no I'm thinking about like it's lame content it's being used poorly by like junior high girls and stuff like that or exposing themselves and it's just they're bad they're bad examples of how snapshot wasn't necessarily a healthful thing and again I like to be proud of my deals on the other hand you see today it is just to network with hundreds of millions of users who are building incredibly valuable content you know with the launch of stories and discover and stuff like that but I got distracted I let the I let the downside a negative case outweigh the risk and yet you know you like you look at uber uber could have it was easy enough to say no to Ober because like oh the taxis or the regulation of the lobby or these drivers are gonna hurt people at some point and somehow I was able to look past all that when nobody else in the valley wanted to and get that deal done what's what I think is is really interesting about it uber in particular is and for those people who don't know it's early advisor to uber so I'm biased obviously in a lot of ways we're going to talk about it but I think you actually got there before me yeah I was pre pre seed money advisor because I've been an advisor at stumble ah work with Garrett and I'm now working again collaborating with him on Expo which is super fun but in the beginning the the way that uber got dismissed and I think this is a really common common mistake it seems that a lot of investors make is people said oh my god really like black cars for one percenters in San Francisco what's the market for that and they they viewed a very niche activity as by definition constrained to say one presenters in San Francisco New York and the if you look at let's say even recycling it started out that way and they kind of confused the first target with the total market and they also looked at just the available market which they missed defined very early on and didn't you know in the case of like an air B&B or an uber they can grow the market beyond any comparable that's available Senate a kiss but the I mean a lot of these start off so incredibly niche that people miss read the market potential I think but let me ask you a question about the getting focusing on the the positive scenarios and the potential high multiple outcomes because for those people who aren't familiar with venture capital its it's a term that comes up a lot in magazines and media cover it's very hot right now so the you explained it in in brief but the it's fair to say that two-and-twenty is pretty fair way to think about it in terms of the I mean not everybody but that's like how people talk about venture capital and hedge funds and so on you have this management fee and then you have the the Cary which is kind of your split but what what I wonder is do you think VCS should not think about the downside as much as the upside because they're only they're rewarded on the upside and not on the downside whereas a hedge fund investors can have long short bets and think more about when I hang out with like hedge fund guys versus say a venture capitalist or VCS the hedge fund guys are many of them much more kind of apocalyptic and they're thinking and it would seem like that is tied to their ability to make money from a lot of this catastrophe yeah I mean those those guys can be short and if you act even if the apocalypse isn't approaching they'll still get people to write articles about the impending apocalypse for those companies to make sure that it's a self-fulfilling prophecy yeah what so what are what are the biggest differences in your mind between the top say venture capitalists hedge fund guys in private equity guys or yeah how do they differ if they do or what do they have income as we were talking about at lunch first of all everyone item on Wall Street is just jacked on stimulants all day long so they're taking provigil they're doing rails they those guys are just in such an incredibly competitive environment that they're using every chemical edge they can find that's definitely not happening in the VC set the VC life demands kind of a much more steady reflective state there's certainly obviously moments of negotiation and and standoffs but it's it's much more of a thought and emotional intelligence exercise you know that said because the valley Silicon Valley is so kind of built on positive energy and lovey-dovey what ends up happening is as the stakes have gotten higher their funds have gotten bigger the industry's more flushed with capital it's more competitive than ever and a friend of mine who I've done some work with who's on the East Coast in the private equity world says the main difference between you know New York and San Francisco is out here in New York we stab each other in the eye face to face and and out there you guys just cut the other guy's Achilles and let them bleed out well while looking at you know it's just it's incredible how I think in in the San Francisco world we we really try and maintain these long-term friendships and try and build these reputations that will scale over time because it's a venture Tablas you're raising money on a every three years basically and it's a ten-year fund and you're hoping to have a long tenure and in the industry with great relationships that you can draw on to recruit people in your portfolio companies that you can use to have your portfolio companies raise more money go public or get sold and because of the fact that we're big equity holders we'll only get paid back upon an ultimate exit maybe eight ten years from now we tend to act more with that in mind that long-term perspective the guys I work with on the East Coast have much shorter timeframes right they're much more used to quarter by quarter analysis of a public company hey do you have any news today you know they um it's it's very very near-term and they don't have the stomach for the ups and downs of building this stuff over time and so it's it's great they're you know they're living on by a different report card than we are yeah so that's the biggest thing you know we you there are other businesses like this like the media business is a cash quarterly business if you go to a media company you go to a record label or movie studio and say let's do an accurate deal and they laugh in your face like how much revenue you're gonna guarantee in year one because that's how they get paid right all those executives are on and you'll contracts and they've got payments they still owe on their houses and the Hamptons and they're just like I'm not gonna walk away from that guaranteed cash right now sorry I'm a break that you're laughing right there I know it's taken your no no this is good I know I wonder it if that could also be related to the fact that say in Silicon Valley it's such a small world and you work very hard to get to a point where you have deal flow meaning opportunities that come to you that are of a sort of pre-filtered high quality right whereas in a lot of these other spaces they're going out and using analysts to sort of hunt for opportunities that other people have not exploited so I mean it's humans responding to incentives right in a way well in a hedge fund environment you're working with public stocks usually at arm's length you might try and go activist and get on the board you might try to like I alluded to change the press cycle but you know for the most part you're doing analysis at arm's length of these companies and the private equity world there's a business already there right there's a there are products or multiple products there's financials there supply chain and so you're going in and saying I can do a better job of this you can and so there's an arm's-length and there's some tension obviously with management usually sometimes your co-opting members of that management team to go get it done but the venture world is different in that it's much earlier and it's much more where the venture capitalist is a collaborator in determining the product and the strategy and the vector the business is going to take and so there has to be a much more collaborative approach over the long term to go ahead and actually build this company so there's nothing you know and I think there certainly venture capitalists who maybe come out of the world of finance or have a different perspective that the their job is just to sit on the outside and tell somebody how to run a business that's that's the private equity model but as a real early-stage venture capitalist your job is to sit in the room and actually work at the beck and call of the CEO to get stuff done to help build this company lend advice about product strategy about go to market about the design of the front page how to staff up and bring in the next couple of members of the team how to go about raising money how to deal with your first PR cycles and so that I think brings a much different person and the successful niche not necessarily the biggest you know self promoter not necessarily the most widely known person etc but somebody who actually can hustle to go ahead and as we go back to what we talked to earlier to tip the balance from something that's good to being totally awesome being great what what books are or resources outside of personal relationships and these mentors that you've had the compliments and so on are there any particular books or resources that have helped you become a better investor yeah I think most of those though are not business books per se perfect that's great guys so I didn't get a business regarding and do an MBA I took a couple classes soon enough to show me as a total farce I did get a law degree which isn't even bigger farce but that's for another episode so so I never had formal business training and so I don't really and I and I tried to look at a few of those like instant MBA books and stuff like that I even bought some books on venture capital and they're just such a so goofy and and by the way part of that is because now we have so many great venture capitalists bloggers who are just an open book about the industry who teach it so Brad Feld comes to mind first a longtime friend and mentor Brad at felt thoughts and has done series over the years where he breaks down each aspect of a term sheet how to understand it in the deal documents and this is what we think is important these are things we think could go away Josh Kaufman and his team have done a lot of work on that we've now seen Y Combinator and the guys at Fenwick and West and Cooley building templated documents that are really really watered down and pro entrepreneur and just kind of have taken out a lot of the legacy [ __ ] that didn't need to be in those documents and so there's a lot of this learning that can happen now without having to buy books and while I happened to go to school and so that's been fantastic but where I worry about the valley and about investors as well as our entrepreneurs is in the development of everything off the ball a little bit so you know you and I I just turned 40 this week that's why you're here happy birthday again all right but as a 40 year old the people my age who work computer science majors in college they that was a major just like any other major they still had to go get a summer job they mowed lawns waited tables they had time in their curriculum to go study abroad to volunteer they had these really well rounded lives and so working with people my age and older at Google who are computer scientists was great because they had not just these amazing amazing math and science skills but a diversity of experience that informed great product decisions as well as just collegiality what ended up happening is computer science degrees got so popular and so valuable that those kids didn't have to pay for school much anymore you know and their only work experience was like TA in a class not actually getting their ass kicked digging ditches or anything and the curriculum was regular rigorous enough that these guys didn't get to go study abroad and there was no opportunity to go do volunteer work and live in the developing world at all and so as a result I actually found we were starting to have a generation of not just entitled you know people talk about the entitlement that Millennials when it comes to work out things stuff but they weren't just entitled but they just had such narrowband perspectives on the world they were missing empathy so they weren't able to put themselves in the shoes of the folks they might be building a product for what the problems of a world might be and so I am constantly looking for opportunities for myself and for the founders you work with to to broaden the scope that they have on the world such that they can build something on a more informed basis an emotionally informed basis so I mean I really think empathy is and it's a word that's been kind of reduced to signal like Oh somebody's you know somebody hurt their foot and I feel bad for them instead I think much more poignant ly empathy is about can I see the world through that person's lens can I figure out what matters to them what are they afraid of what's bothering them what do they think is limiting them right now what's their hope and if I can do that then it's a lot easier for me to build something for them and to sell it to them and to help them and to build a longer-term partnership with that person if you were giving a assignment to folks for books or experiences just just kind of a short list for people who want to develop that type of empathy what would you put on the list one of my favorite books that we give to most founders is not fade away I think it's like a leash flop pick on the cover yeah a belly flop pick a short life well-lived story of Peter Barton that so first of all just on a personal note that guy's trajectory kind of followed mine he was a ski bum who suddenly made it big and tacky was on the board of Yahoo he worked at Liberty media and then he hits his forties and says okay I've accomplished what I want to accomplish I'm dialing it back I just want to spend time with my family and at that point and this isn't a spoiler it's literally how the book starts he finds out his incurable stomach cancer and so the book walks walks you through his biography as well as the remaining time in his life you will cry reading this book it is inevitable if you don't I'm very worried about you but you'll definitely cry it'll be cathartic but it's the kind of thing where you it's it's an exercise and okay what's on the mind of the person who's dying and how is he thinking about the impact of his death on his family on his friends on his business partners on his legacy on the continuing responsibilities as a dad even in the absence of you know even though he's passed on in the next life and it's an entire exercise in perspectives and I think that book will not only leave you feeling incredibly lucky for what we've got here and where we are but at the same time will will sharpen that that that sense of how do I put myself in somebody else's shoes a similar book that I love it's I I'm gonna get the title wrong I think it's how to get filthy rich and rising Asia I think it's what you told me about this it's focusing yeah so it's written in the second person which I don't know of another book like that but it's just you you you like you wake up in this room almost like an old you know look like an old roll player or something like that online it dungeons a dragon yeah well it is reading - you are in a room there's a sarcophagus open sarcophagus no it's uh but it says you know you wake up and you basically start the book in a slum in Pakistan and it's just writing you about how you go through your day the things that matter to you and it turns out you're kind of entrepreneurial and you're willing to take some risks and so you start working into other stations in life and I don't want to give anything else about the book away but you close that book and you feel like you've you've walked through 15 to 20 different lives in another world and I just think more of that would be better for all of us I think it'd be better for our industry for the depth and the impact of the products he built I think it'd just be a lot better for getting along with each other so I mean you and I have traveled to Ethiopia together doing work with charity water it's hard to complain about a day's work back here in the United States when you have been in a village where they walk three or four hours each way to get water where the kids are dying because they drink the same water that the cow poops into where the women don't get an opportunity to go to school because they're carrying the water and on the way they might get eaten by a lion or raped and it's it's really hard to find yourself complaining about our privileged us life and and that's something you could just tell working a big company like Google there were the people who would [ __ ] and complain and like really really this is a hard day Microsoft launched a competitive product and that's our that's our horrible day and I just think we'd all be much better off if we were able to find opportunities for our CS students to go study abroad for for our MBAs to actually spend some time around poor people and and to start building these more diverse perspectives when you look back on since its its the big four oh when you were thirty who came to mind most when you thought of the word successful and now at forty who is the person who most comes to mind when you think of the word successful so 30 that's a really I got let me think of where I was so I guess I was at Google at the time who was most successful just when you were like I want to be successful and the person in your mind who embodied that most yeah I always wanted to be at the center of the deal and so at that point in my life I still really admired for instance so like a John doar or Michael Moritz they were both on the board at Google brilliant guys who used their station in life to gather even smarter people to teach them about things and then they would use their unique talents for storytelling in and making composite kind of ideas come true to build companies they became billionaires as a result they had great families they were just well respected by folks I think I still that was kind of my definition success at that point at 40 and what I think my journey from 30 to 40 was about was to stop trying to define or build some kind of model or have some kind of role model out there and start to stop trying to define myself externally because that's a distraction so there are times when you're doing a deal with John doar you're across the table or someone you're like hey wait that was [ __ ] up you know like I don't wait you're supposed to be my my here on my idle and I don't like that movie dismayed or something like that right and I think you know anyone I've ever put on a pedestal I've just been disappointed by doing so I'm sorry about that by the way yeah oh you have novara no idea how far you've fallen Tim but but so I think for me the exercise has been how much am I gonna define that for myself not by looking at somebody else I recently got to have dinner with next to Bill Gates Bill and Melinda Gates and I had been raised to hate him you know growing up at Google you know he's a pretty evil person and I was sitting next in there and I got a chance to basically interview him about how they have structured the foundation how they think about which causes to take on which challenges to tackle and I mean I walked out of there just deeply admiring their work but I think I want to limit it to that and not get into like is he a great family man is he you know he's still son of a [ __ ] when it comes to competing with him and software his default browser knows antitrust behavior but but I really some I'm trying to look at people and find kind of one aspect of them that I like but for the most part I've had to decide okay what's really important to me that's my wife and my kids and you know I I'm I'm just not that social anymore I just don't hang out with people that much I don't go to conferences I'm just not available for dinner I would infinitely rather spend that time with them and so that was a priority choice I had to make it internally not because I saw anybody else killing it that way you know I think I reflected back my own parents who who opted out of much more accelerated career paths so they could spend way more time with my brother and and so that's a choice I had to me but I will say do you know about the journal I found in my mic I got you and you should you should mention that have a quick well observation is if I could spend more time with crystal instead of me I would do the same thing we actually met before you and I met at fairtex kickboxing way back in the day well well yeah I was so I was having a some I was having a bunch of people down for cocktails we came down from Truckee into the city Kristen I did I was like let's get a bunch of people together for cocktails I invite Tim and Tim walks in and he looks at my girlfriend he's like I think I know him like yeah sure you do man everyone uses that to try and pick up my then girlfriend now wife he's like no and then she says yeah I think I know you two I'm like oh [ __ ] here she goes like I'm gonna where's this going he's such a hunk what do I have to offer it but uh yeah you guys used to you guys used to train in kickboxing yeah yeah she was hardcore there's always but I want to pause for a second the the I do want to hear about the notebook for sure cause I think it's amazingly nostradamus like but the you and your brother so you know brother have had a very different careers have done very well respectively what did your parents do that you are also trying to do with your kids yes and my brother Brian sacca he's on the first youtube sketch stars he parlayed that into he sold him the first web series ever made [ __ ] ton of money building web series in fine and commercial partners for them and stuff just movies like yeah wolf of Wall Street was Scorsese recently and then just yesterday or allowed to talk about this now he his his series on TBS got picked up so he's gonna be a co-star of a comedy series on TBS pretty amazing um so what did our parents do well first of all they were just always involved so my parents took vacations with us we always went to national parks together we never went to resort type places we were just always together and you know not only they read with us like most parents but my mom would pull us out of school to take us to go see an author read you know at at a bookstore an hour and a half away she would literally just pull us out of school to go to a science museum and so she was a college professor and so she had a little flexibility in her schedule she Anka said she would take us to a park called art park I've been luest in New York art to park art park it's a state park in New York State and loosed in New York where the whole thing is dedicated to different art media and so you can paint there you can blow glass you can watch a performing arts troupe the kind of vaudevillian theater and stuff and in my parents eyes that was just as or even maybe more important than going to the public school and so I think that kind of enrichment and and I'm just being shown that people and all these walks of life were important and fascinating you know I grew up where by the time I got to college I had never heard of an investment banker I I didn't know that was a job you know I'd been exposed to to writers to artists to chefs to musicians to engineers to lots of teachers to lawyers to doctors but it was never you know what it wasn't necessarily driven in any in any particular way to kind of get us to a particular career at all I will say there was something else my parents did that's pretty unique and it was called my brother and I refer to as a sweet-and-sour summer so my parents would send us for the sounds like a Chinese restaurant they would yeah they'd send us for the first half of this summer to an internship with a relative or friend of the family who had an interesting job so at 12 I went interned with a my God brother who was a lobbyist in DC so I would go along with him to pitch congressmen I had one tie and you know for for work I would I was a pretty good writer shot right up one-page summaries of the bills we were pitching and I would literally sit there with these congressmen with these filthy miles you know the Alabama senator and stuff like that and and watch the pitch happened it was awesome I learned so much I think I built so much confidence and really honed my storytelling skills but then from there would come home and work in a construction outfit with just a nasty nasty job I mean whether it was hosing off the equipment that had been used to fix septic systems gasps and [ __ ] up dragon [ __ ] around the yard filling propane tanks just being junior gonna put him told him quite literally getting my ass kicked by over whichever parolee was angry at me that day for minimum wage I think was part of their master plan which is there's a world of cool opportunities out there for you but let's build within you a sense of not just work ethic but also a little kick in the ass by why you don't want to end up in one of these real jobs and so let's see if you can find in yourself the drive to go and do whatever it is to and did they choose for instance you had the introduction to say the god brother I think you said little lobbying did they also help organize the the sour part to teach summer yeah so that the guy around that construction company and equipment rental companies my dad's best friend he's under strict orders to make sure we had the roughest day there are special treatment yeah it was yeah we were treated specially shittily so we were we were hammered there and by the way as a result I know a lot about construction equipment this is this is a superpower of mine I can literally from air compressors to ditch which is to anything you need in Milwaukee sawzall hey I literally have incredible amounts of knowledge in that space it also just reminded me of something you mentioned long ago and I'm not sure if it's still true but you said one of the things that you look for and it's maybe not a disqualifier button founders is a track record of having had at least one shitty job yeah yeah well I missed particularly for that in hiring so I want people who've lived studied travelled extensively abroad I want people who've been exposed to poor people and by the way the lip study travel works essentially abroad is because you can get away with a very comfortable life in the United States as an English speaker particularly as a white person you never really have to ask for anybody's help you're not being prepped her ass by the police it's pretty easy pickins you find yourself overseas particularly in a place with a non Romance language where you can't make out the signs yourself and you to stop and ask for help from complete strangers you literally have to be entirely vulnerable to people you've never met and just expose yourself and they could send you into a dark alley and beat the high you and take your money or like most people on the planet they'll be really nice and hit and try to help you even if you don't share a word of you know of English in common and I think there's something incredibly form of about that experience of having the humility that comes from having asked for help you know the best managers in the world are people who are great at asking for help and realizing that makes them a more powerful CEO than a less powerful CEO or more powerful manager than less powerful manager and so I look for people for whom athletics is a big part of their life I don't think it needs to be team sports necessarily I think you can you can be a great individual athlete you know maybe you train with other folks etcetera but I think it just shows not only some self discipline but also just a value on the introspection that comes with athletics you actually care about yourself I think there's a little bit more balance in that life I can also teaches you to contend with losing and sort of viewing that as feedback and not some type of failure death sentence sure and then seeing I think the temporary and how temporary pain is you know in that's temporary glorious forever yeah oh it's true so I mean I remember when I did an Ironman and when I was when I was doing that in the and I had a fever that day huh 103 to do fever but my parents had traveled out to watch the race and so I didn't want to not do it and that advil worked for like the swim in the first part of the bike and then I was just I was a mess but I remember thinking no matter what happens I will be in my bed tonight and you know this is a very very temporary moment in 2009 I rode my bike across the country and I remember you know it's 35 days of riding basically a hundred miles a day I remember multiple days out there I'm like I'll be in my bed tonight and then to the other ear is this voice and then I have to [ __ ] do it again tomorrow today I'm gonna pull out a couple of random ones but what historical figure do you most identify with buckminster fuller why and maybe you could give some kind for people who don't know rain who don't recognize buggy so Bucky is I mean there I have a feeling if we went to his Wikipedia page there'd be a paragraph of of nouns describing this guy he's a mathematician he was a philosopher he was an engineer he was a poet he's a lecturer a teacher he's an inventor a futurist he he's one of the few people you will find that is willing to write the optimistic case for technology that that all this stuff isn't leading us to dystopia that we actually are busting Malthus and the Malthusian kind of quandary wide open that we now have the resources to feed everyone clothe everyone power everything without having to dig holes I mean the guys he passed away 30 years ago now but but there is an optimism to everything he writes there that these machines aren't here to take over that humans are good at heart and there's something really inspiring about that is we wrestle with some of these big scary issues about the power of the Internet to you know we periscope gets launched and in the first week I am getting questions from reporters about well can't Isis use this to rally people and you're like seriously that's the part you're gonna focus on a periscope like all the amazing uses for a periscope which i think is absolutely groundbreaking technology and really really cool and people are so focused on that negative case and you at the same time I think periscope can be used to inspire educate he'll bring people together across so many different planes that it's easy to get distracted by that negative case but I think Bucky more than anyone I know found optimism and the stuff that could otherwise be pretty daunting hey also didn't he also create it's not geodesic that's not the word I'm looking for in the domes yeah the spheres geodesic domes yeah yeah they're yes it dome so yeah that you see people constructing at Burning Man yeah fascinating guy in the buckyball and the buckyball really interesting dude also the concept maxxium there were more there's some type of tensegrities integrity which good good man so this this concept of tensegrities I'm not gonna do it justice but it there are some really interesting parallels between his discussion of this concept of tensegrities and the role of fashio within the body yeah because if you didn't have fash I mean your organs are basically just drop down to the bottom of your like torso cavity and just sit there in a pool of nasty meat but you have this fashion that holds you together super super interesting guy completely agreed did you collect anything when you were when you were kid and then we need to talk about your notebook yeah I mean I collected money so if did money I mean I was just all I always wanted to make money and just I do the backstroke like like Uncle Scrooge in the pool of points yeah excuse me I scratch my monocle swimming through my room full of gold coins no I I was a hustler from day one I grew up middle class so we never had want of anything but I always thought there would be a certain independence that came with money a certain excitement that came with making money and so from the earliest days I would you ever seen the like those pungent walnuts that come out of a tree they've got that green pungent skin on them and if you if you pierce it with a fork it smells like ammonia so I would grab those things out of our front yard putting my wagon pierce holes in all of them that I build a sign that says air fresheners 25 cents in it like I'd put it on my brother like a sandwich board my younger brother and I toe it up and down the street and sell these things door-to-door and all the people would call my parents and just pick do you know what your son is like here but they'd still buy him so I'd clear like three four bucks come home richest you know richest six-year-old in the neighborhood and I just love that hustle I was always going after you know is that something you were just pre-programmed to do or did your parents facilitate that it's not it's not either my parents game at all like they were notes I mean my mom is a really accomplished professor and an author in the field of education my dad is an incredible small-town lawyer who frankly could have made a lot more money but was constantly doing pro bono work for people in our town he's incredibly revered person with so much goodwill and so neither of them were were hustlers like that but I was always looking for the angles there a movie did you watch like the toy or what was their true trading faces was their trip where the Train plays a good movie no I mean I will say you know I traded baseball cards despite not liking baseball at all I never watched any games but like that 8687 Don rustier the 85 tops you know with Canseco rookies the Roger Clemens rookies the Mark McGwire Olympic card from 84 like I was really into those things because I was good at it and I could make money doing it later I realized I was really good at playing cards too so I played a lot of cards I ran a card room in my high school one of my teachers what type of card games were done we were playing a lot of booray which is a game that's only played in New Orleans and blackboard in New York it's a really high stakes geometrically growing pot game and so you can really you can just gutter fool there yeah and so especially if you're teaching them the rules a lot of that a lot of Hearts a lot of big pitch a lot acey-deucey and just really street games really that and we had a teacher who took a rake I had him I had him on the take so we could he could write passes so people get to the card room but I always kind of just had a hustle when I got how old was that held me I did that I started that in junior high one of our friends what does this teacher teach what was their subject know one of our friends his mom was a teacher and so she had an office so we got to use the office as the card room that was more acey-deucey back then it wasn't a really cerebral game but again it had the progressive pot type stuff in high school it was my is my cross-country coach and an American history teacher mr. main he was a gem and that was that guy he just knew that I wasn't cut out for public high school and so he you really help me you've also have you've always had this hustle I wanted I have to ask and if you want to parry this one feel free but so I've heard these rumors that you got through law school without going to any classes yeah well I if I if you go to class then they've got your name on the seating chart yeah the first day you have to sign the seating chart goes around and then you sit in the same seat every day in law school but if you don't go to class and your name's not on a seating chart and so they can't call on you and realize you're not going to class and so instead you go to the exams and the exams are just printed off the registrar's role right seat and the the teacher of the class isn't there so you just sit down for the exam and if you're a good test taker you can kill it and I was amazing I had some of the best grades in my law school how did you headed to York Street then what was the method to the mat well the funny thing is unlike any other college class or MBA class what's taught in the classroom in law school it has nothing to do with being a lawyer and B has very little to even do with the exam it's it's such a joke man the Socratic method and stuff like that I think there are some people who need to be taught to think linearly you know Pro Comp Pro Comp pro con but I think about that point I and my roommate Kevin Cody who you've met you know we're already there Owen brainer - brainer Capital was the year ahead of us at Georgetown Law School and he helped us realize this method he was like the Tim Ferriss of Jewish law school he helped us understand what was important what wasn't and it you know in my heart of hearts I wasn't really there to be a lawyer I think if I'd wanted to be a litigator if I really wanted to go try things before the Supreme Court then going to law school and actually attending a class and interacting would have been a great exercise I went there because I thought it was my fastest path to a seat at the table in Silicon Valley I wanted to be in the middle of a deal and and have people listen to me even though they probably shouldn't because I had very limited experience but I wanted to be in the Maelstrom and I knew that if I went and got a kick-ass law degree with great grades I could end up at a kick-ass law firm in Silicon Valley and be a guy who at you know 25 26 they were gonna listen to where else does that happen so so that was the path but yeah I kicked ass in school without going any I will say this you might have heard the legend but so the the thing you do need are some notes from some of the classes to understand like which cases the the professor brought up and what they think is important and so I threw a keg party every semester where the only thing you had to bring to get into the party where your notes so classmates would bring their notes to the party throw them in a bin and then I would go Xerox them all and and build kind of a composite and use that to study for the exams it's a genius and the the notebook that you found not too long ago this all tracks together but we're approaching it in kind of a memento type fashion yeah that the notebook tell people about this notebook yeah it was funny I was just just two years ago I found this in my garage and it's really it's been weighing on me and particularly this week turning 40 so I was 19 I was twenty years old actually I was twenty I was living in Ireland going to school there I spent two out of my four years abroad while at the school Foreign Service at Georgetown and so I'm living in Ireland and there was an expat girl in one of my classes and we were basically flirting with each other by taking a notebook and writing in ten questions for the other person to answer and then you get you get it back and you answer ten questions and write ten new question we pass back and forth while we were supposed to be studying like 20th century Irish film or something like that and at one point one of the questions was what do you want to be when you grow up some twenty I'm living in Cork Ireland we basically would start drinking stout around 11:30 a.m. every day it was like second and third meal was stout and by that point I'd still never heard of an investment banker I definitely never heard of a venture capitalist and so I just write in there I said I don't know what the what the job is called but I know it's gonna involve a lot of talking on the phone a lot of negotiating a lot of yelling at people high-risk high-reward unbelievably high stakes I'm gonna do a part time from the mountains a part time from the beach and whatever it is I'm gonna be done with it before I'm 40 so two years ago my wife and I are standing in our garage in the mountain house cleaning it out because we're moving some stuff down to our beach house and I find this old notebook and I'm like hey look at this and we're flipping through it and I find that answer I just really choked up it was incredibly weird self prophecy that I kind of laid out exactly what my job was but I also felt a certain amount of pressure like so what do I do now I'm 42 I keep doing this job or not or do I need to do I need to listen to the scrolls like shatter some type of cosmic continuum if you if you don't follow the prophecy the so you do spend a lot of time on the phone or you have historically clearly a very good storyteller what are the what are the words or phrases that you overuse the most the words or phrases that I overuse the most amazing bananas cocoanuts is cocoanuts a close cousin to bananas yeah that is cocoa nuts I use the phrase that said a lot as a transition you know transition words are really important for me because having I know you've studied how to learn other languages one of the things I always focused on when studying and I speak Spanish was was transition words like seeing them about eagle-like nevertheless you know like I needed I needed to have those transition words down because that's how I could tell a good story that's how I would layout we're in a new paragraph even if you haven't been following me I got a new concept coming and and I really think studying it that way and bringing it back I used to live in Spain in Ecuador El Salvador I bring that back to my English and I realized I'm really clear about my transition where it's now so hard returned that said yeah but I am you can ask Matt Mazzio's my partner you know we write updates to our investors that no other fun does like we write deep colorful narrative about all of our investments the state of our companies the state of the industry our own personal States what we're thinking about and by the time you see one of those as an investor I've probably edited that thing like Mazzio's you know draft fifteen to twenty times I'm obsessive about writing it needs to be crisp original no repetition of words and phrases I need to bring it and that was something I got directly from my parents who are both exceptional writers but I think in in colloquial terms when we're talking with people I try and emulate whatever the language pattern is the person I'm talking to it makes them feel better I don't you think I do it consciously like you come to an island like this it's staffed all by Brits and you can't help but suddenly find your arse getting a little bit funny and you're like okay okay hold off yeah but but I think that's something I really try and focus on is speaking in the same speed as the person I'm talking to you seem to have had a very clear picture as reflected in the notebook and obviously the early hustle you have this Drive that seemed to point a very particular direction I know that when I was about to graduate from college I had no idea of what my next move was and law school hadn't even entered the realm of consideration what would your advice be to college students are just about to graduate who have no idea kind of what they should focus on which what they should do do you have any any thoughts kind of general suggestions that you would make to someone in that position well I did give a graduation speech I think it was two years ago now at the University of Minnesota school I didn't really have any ties to and they reached out to an agent who hired me for and that was daunting right because I give speeches all the time and it's usually do a roomful of like Conoco executives in Kissimmee Florida and I'm just there for the check but a graduation speech is intense that's hopefully memorable hopefully formative hopefully you're talking to people who have incredibly open minds and it's such a meaningful transition point their lives so everyone should go watch it but what I focus on was be interesting I think you know here you're here for a week where I've gathered my favorite friends and one of the reasons why the week is so fun for everybody is that everyone else here is totally interesting right not necess really a Titan of business but just interesting compassionate adventuresome people who just go for it who are up for it and I think as I look around who I've hired who I like to work with who I back they're interesting they're people you want to be around you want to spend time with you want to hear their answers you want them to influence your thinking you want them to push you a little bit to try things that you haven't tried you want them to teach you and if I could give advice to someone who feels like they're looking at a maze of opportunities and none of them is particularly presented or they're not sure how they want to get ahead or distinguish themselves I think pursuing a course of life that embraces interestingness and by the way I don't think people are born interesting I think it's actually something you can accrue living abroad volunteering for a group like charity water and going into the field taking an actual service job going in and talking to the people around you and having meaningful conversations including the homeless people including your neighbors and people who are actually working for wage getting involved in politics briefly you know I think I campaigned for Obama a couple times and I was everything from one of his top fundraisers to I actually spent time in the field in Elko Nevada which put me into the mobile home living rooms of some of the poorest people in the country who's who somehow were supporting you know the Republican Party in that election and it was it was surreal but it gave me a life perspective that I don't think I would have had otherwise so I think those kinds of things make for much more compelling people and will start to present career opportunities so one question that I'd love to ask is when you were sort of in your most recent sweet spot of wealth accumulation whether it was related to what you did with Twitter or otherwise were there any particular shifts or routines habits that helped you go to maintain that peak output or achieve what you did yeah so I mean you know my personal story so I certainly been fortunate to make a bunch of money last few years but in bubble one I made a bunch of money i levered up lost it all and a lot more leaving me millions of dollars in the hole was able to work it back out to zero by 2005 and since then you know a lot of work a few ups and downs but it's worked out pretty well and it's looking good for the road ahead too so that said I don't think it was any particular like I don't think I have a calendaring function or an email function or anything like that that's like a hack as much as I would point to two things that I think shifted the nature of my business one was that before I had really made any money at all and before I had any business doing this my then-girlfriend is now my wife Krystal and I moved out of Silicon Valley up to Truckee I mean literally took ourselves out of the game as a you know an angel and venture investor like how do you how do you manage a venture practice from up in Lake Tahoe and yet what I realized was that being in the city I was just playing defense the whole time I was taking these coffee meetings listen to these poor pitches you know being being friendly and kind of obliging people with their ideas but I'd spend all day and these meetings I get home and I'd be like [ __ ] I haven't actually accomplished anything I would go to the cocktail and dinner parties I was invited to but they weren't actually the people I wanted to spend the time with and so I was just I was just reacting to everything rather than actually going out and playing offense and so Krystal and I moved up to Tahoe and we've quite literally built a list of people we wanted to know better and we just started inviting them to come up and stay with us in Tahoe you were definitely one of those people right and you came up and spent a lot of time with us there we I also started writing lists of the companies that I wanted to get to know better and I just went in deep with them and asked them to come up to Tahoe and so I was playing offense now and I had it perfectly seized for why I couldn't get coffee with all the randoms and like hey I'm sorry I'm just not in San Francisco I'm three hours away there were a couple of sessoms who drew who drove all the way up there but for the most part I was able to pick and choose the interactions that I thought were gonna be most valuable to me to my wife into my business and that was a huge shift and it was risky as hell because I mean I couldn't even really afford the house we bought up there when we first bought it $600,000 three-bedroom house and and I certainly didn't have a strong enough brand that I could afford to just walk away from the game but I made a conscious decision to play offense from up there and that worked out I mean I got to know guys like you really well Travis spent a lot of time in her house having limbs and Jason Goldman from the Twitter team we had teams like I mean the locu guys was a great deal we sold to GoDaddy we just had many many teams as well as many friends Ted Ryan Gauld who found our doctrine cats are now CEO at one of our hottest companies in venture was a guy we got to know very well from stay in our house David you Levitch CEO and founder of Open DNS guy we got to know really well stay in our place in Truckee and so these are people we just go deep with Garrett camp spent some time there just just a really really cool crew that I think we got to know way better and build much more meaningful relationships breaking bread making dinner hiking skiing that kind of stuff the second thing that I think was different was that after a couple years of trying to explain to people why Twitter was gonna be a real business and why you know people would look at me like how are they ever gonna make any money man if you don't see that and so I finally just said [ __ ] it I'm not here to convince you anymore I'm just gonna buy all your stock and there was just us there was a bit that flipped for me as a seed investor you have to be very collaborative you're constantly trying to get you know basically bring people into your worldview and say okay do you see the future this company this is why you want to invest in this company and the series I our Series B this is why you want to buy this why you want to work there and I got so fed up with doing that on Twitter I was just like [ __ ] it if you if you can't see it anymore then you don't deserve to make any money on this company which is like just unhand the [ __ ] chairs I'll take them and so I just started buying that stock up from early investors who wanted to bail etc and by the time of the IPO my affiliated funds that we're doing this owned more of it than anybody else we had about 18% of the company so that worked and so there's just there's a few times where you know it wasn't necessarily the polite or most political way to go about this thing it certainly was daunting the amount of money I had to raise to buy that much of the company but the bit just flipped for me I was like [ __ ] I'm just not gonna play this traditionally anymore no idea just to touch on one aspect of that I know we have to get ready for dinner and run in a few minutes we'll wrap up and maybe do around two sometimes people like this otherwise it's 70s disco night tonight are you ready oh you know idea I sacrificed luggage space for all of my other stuff so I could get my disco gear here wait so can I just ask the luggage space question yes is is that why you insist on wearing the speedo when you swim here is that please tell me there's some reason other than at lunch we we came to the conclusion that you might actually be aspiring to be a seven-year-old German man at some point like that's the that's the path your life is on I actually every Jenner is on a transition to womanhood and you're on a path to transition to being seven year old German man I was thinking more like a Greek man I saw this photo but actually what no it wasn't a photo there was this guy walking down the beach passing me and a friend I was in these like really baggy board shorts like cool if I can Brazilian surfer style horrible to swim in by the way it's like swimming with a parachute behind you but walking down and this this Greek guy wanted wanders by it's got like these blue skivvies on that are just like his guts hanging out like basically covering up 70% of them covered with obviously like silverback hair massive gold chains glasses could not look [ __ ] happier and he just gave zero [ __ ] about our opinion whatsoever so I was like you know I need to like put on the training bra if I'm gonna get to that point so I do wear the speedos no but your Power Move today was you came to the lunch table on the beach with regular trunks on and everyone commented like oh thank god ten more regular trunks and then as you walk towards the beach you dropped your regular trunks they were almost where they tear away sand and reveal the speedo and then proceeded to swim well the excuse that I'll use is part of the reason I think I failed to learn to swim properly for a long time was partially a wardrobe malfunction because I'd wear these baggy shorts oh it would hold me back so this is uh this is my effort to be more dolphin-like and less drowning monkey-like but what does it does work in the water it's just on land on land it's a bit it can be offensive to to the more sensitive Americans among us but yes so that also takes up less space it's it's you can fold it up but it was a hockey figure I really wanted to believe that you weren't wearing those because you liked them as much as it was a large one of the instructors here one of the guys doing kite surfing or something was like it is he wearing those seriously or like ironically he did so on a completely unrelated note where the [ __ ] was I gonna go with that who knows I tell you what I know we're tight for time so I will two last questions and then maybe we can revisit a bunch of this another time but is there any purchase that you have made could be years ago or recently less than $100 that had a significant positive impact on your life okay I mean just draft top to have the first thing in my head was there's a buckminster fuller book called I seem to be a verb incredibly incredibly limited production you have to buy add vintage if you're gonna find it I regret even saying it out loud now because there are so few copies out there they'll be Hoover it up by your audience they're gone but that book and it's special it's actually it's beautiful inside it's not like his other books which are just long long texts it's graphic lettering and photographs and you read it through on the top half first and then you flip the book upside down and you read it through on the bottom half in the other direction it's super companion or some great thoughts in there it'll cost you I mean I don't know what your what your viewers are gonna do to the market but it's under 100 bucks but it's incredibly special very very treasured awesome yeah those those will disappear pretty quickly so get them while they're hot I guess any last pieces of advice or recommendations to leave with the would-be entrepreneurs who are listening to this people who are thinking about starting a company of some type think that that's their path maybe just a shitty employee like I was and are out there hoping to have a head start in somewhere an advantage what would advice or recommendations when you make my first recommendation is be honest with yourself most people aren't that person and I think we are an environment right now where there's so much venture capital in the industry you know the tech industry has been shown to be so cool great perks and a great fast path to path the wealth that it's very attractive right now to posers and I think most people aren't cut out to be founders most people aren't the entrepreneurs will have that ultimate success and it's polluted our industry you know we have way too many shitty companies that are pulling all the great talent away from inevitably great companies we have way too many people wasting time on competitive ventures that have no hope whatsoever and so I think you have to be really really honest are you a founder or are you an employee and one of those things that we touched on earlier is that inevitability of success if you were it people ask me what went through my head when I lost 12 million dollars in in a matter of a week and that was another $40 on top of that just a really highly levered public market by which one upside down in a crash and then four million dollars more from there leaving me deep deep in the hole and people asked like were you sad were you and I just my brain works in a way where I wasn't sad I was pissed it was a bummer but I just knew I would always make that money back and get back into a good spot again I was just gonna take longer I just knew that I would never be the guy who just lived out you know and declared bankruptcy and living the holdup the whole time I just knew I would make back the millions of dollars and then go from there when I went out and branched off and started my own firm you know I spent money to do the documents that a big big firm would do right off the bat and even though my lawyers like we don't really need to do this it's small firm and I well this is going to be a huge thing so I want to do that now when I set out to raise you know a billion dollars in the fall of of 2010 that was absurd I didn't even have office space I had one other employee at the time who managed our our back office from a winery in Healdsburg and so I had no business raising that money I work how boy shirts the whole time and rarely left Truckee California to do it asked everyone to fly their fancy jets into Truckee and get it done at the greasy spoon and so there's just I just knew there was an inevitability that this thing was gonna work out and that I wouldn't fail at it if you're not the kind of person to think that way if you really don't have that gene where you know it is going to work out no you don't hope you know then you shouldn't be a founder so I hope that doesn't depress anybody but hopefully I'm saving a bunch of pain I think there are also many paths to amassing incredible fortunes and being a founder is actually a pretty thin slice of that pie and very high risk sort of binary way to approach things what is the what is the movie that you can quote from most readily available I mean you start with the opening scene with Sam and I can recite the whole thing I go to Lebowski Fest every year I might my division that had a Google was secret we're working on secret stuff that now you're starting to see kind of all the spectrum and wireless system stuff they did we actually launched the first weather balloons you know Cassidy went on to build loon and stuff like that we dug the fiber etc but that whole division was called Project Lebowski and if you anytime we launched something or achieved a milestone and everyone got achiever shirts it's a you know little glossy urban achievers inner-city children of promise without the necessary means forth necessary means for a higher education so Philip Seymour Hoffman recipes so yeah that was a that's a pretty important movie for me awesome where can people find you on the Internet's I'll give one more book recommendations since the the Buckey book is probably in vanish the magic of thinking big I think is is one that I found very help other people might as well but on the on the net we given book recommendations right now sure you know one of my favorite favorite books what's uh is the essential scratch-and-sniff Guide to becoming a wine expert there's a fentanyl authored by my my fabulous wife it literally you know the master sommelier Richard Betts there's incredible knowledge in that book so my wife and Wendy MacNaughton the illustrator combined to make a a children's book for adults it'll teach you how to drink wine that's indispensable for any aspiring entrepreneur it's super fun I might have to have bets on at some point to talk about hacking the master psalm test he exactly what he does he teaches people I think get a long lunch and talked about it he's a fascinating dude so the the web the ever-expanding web of Sakha so where am i I'm at Sokka on Twitter I just don't use the instagrams very much anymore I'm also at sac on periscope and that I've been using a lot I think periscope changes everything cool man speak about changing everything and get to disco night so we gotta get running that's right that's right all right thanks brother always fun thanks to him this episode is brought to you by 99designs your one-stop shop for all things graphic design related I've used 99designs for everything from banner ads to book covers including sketches and mock-ups that led to the 4-hour body which later became number one New York Times number one Wall Street Journal and the brainstorming a lot of it took place with designers from around the world and here's how it works whether you need a 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Channel: Tim Ferriss

Views: 24,741

Keywords: tim ferriss, 4 hour workweek, 4 hour body, 4 hour chef, forbes, timothy ferriss, entrepreneur, author, writer, best-seller, public speaker, angel investor, ferriss, twitter, Facebook, stumbleUpon, evernote, uber, tim ferriss blog, timothy ferriss speaker, Chris Sacca, Chris Sacca Interview

Id: iqaXz2BPsfY

Length: 96min 56sec (5816 seconds)

Published: Thu Oct 29 2015