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Hanging up my spurs
- kevinmannix 9y agoChris Sacca is one of the few VCs that people outside of the SV bubble and even the tech world know and associate with the valley. He, along with Mark Cuban & potentially a few others will likely be part of the few of this era remembered many decades from now when history gets consolidated into a few figures, much like Gordon Moore of Intel & William Shockley of the Mountain View of the 1950's.
- hashkb 9y agoBecause of Shark Tank?
- charred_toast 9y agoJudging by his website, because of his extraordinary ability to vet tech opportunities. Check out the list on his Posse page - it's staggering.
- mozumder 9y agoI'd like to see a list of his investments that also includes the ones that failed, as well as the amount on each investment. Are there places that track this info among VCs?
- mbesto 9y agoPitchbook, it'll cost you a few grand a year though.
- rlucas 9y agoPitchbook doesn't even come close to figuring out the actual invested amounts and returns across an investor's portfolio. Don't get me wrong; Pitchbook is good and I pay $$$$ for it. But it serves a company-centric intel need, not an investment performance measurement need.
- sah2ed 9y ago> not an investment performance measurement need. Can you please expand on this? Genuinely curious as to what the metrics are in this case.
- rlucas 9y agoYes, you can buy this from Cambridge Associates, and a few other "consultants." But it costs more than you would be willing to pay out of mere curiosity. Generally speaking, the institutional limited partners (LPs; pension funds, endowments, family offices, etc.) that invest in venture and private equity incur pretty significant costs to get third-party information about actual performance by managers (i.e. VCs). From largest to smallest, LPs might generally: subscribe to Cambridge's data and use it in-house with full time staff, or hire a consultant (like Cambridge) to assess and help select their managers, or pay a fund-of-funds a fee (on the order of 1%) to do likewise. The point of all that is: figuring out who is actually making money in VC, and guessing who is likely to continue doing so, is very non-trivial. It can't be done with publicly available, Crunchbase / Angel.co type data, much less a VC's own statements or portfolio listing page.
- YPCrumble 9y agoPerhaps I'm missing something, but is this the list you're referring to? http://markcubancompanies.com/index.html http://markcubancompanies.com/index.html What is staggering about that list? It looks pretty much like any list of a VC that has survived. One or two big but not tremendous plays like Dropbox and a lot of companies I haven't heard of before.
- deleted 9y ago[deleted]
- mbesto 9y ago> vet tech opportunities Sorry to snark, but the ability to vet opportunities isn't necessarily a skill that allows individuals to gain such a staggering list of investments. It's worth noting he improperly "vetted" Snapchat[0]. On the other hand, getting proprietary deal flow is. It would be easy to rank him at the top on that. [0] - https://twitter.com/sacca/status/837400028352151552 https://twitter.com/sacca/status/837400028352151552
- kevinmannix 9y agoIt definitely has some part. I don't think the reason really matters. It's a variety of things including personality that somehow eek out of the niche field into the mainstream that causes a singular person to become associated with an entire movement.
- ameister14 9y agoI really don't think Mark Cuban will be on that list.
- ChicagoBoy11 9y ago...but he put radio on the internet!
- jacquesm 9y agoMark Cuban got rich of one deal that probably shouldn't have happened in the first place. He got very lucky.
- gist 9y agoAs you know there is luck (of various types) involved for anyone who has ever gotten anywhere (even if family connections as a separate benefit there is also luck). You have to give Mark credit for doing a good job of snowing and playing Yahoo that does take skill. Look if Steve Jobs had grown up in, say, Iowa USA, had strong family ties that prevented him from even thinking about moving to Silicon Valley, where would he be today? If Bill Gates's mother wasn't on the board of the Red Cross he'd never have the IBM connection that gave him the contract. (Forget as well that he was the right age at the right time as well). Notoriety and wealth is always outsized relative to actual capabilities. Was watching Bloomberg on 60 minutes. Sure Mike is a really smart guy. Worth 40 billion or whatever. But compared to a smart guy who is worth 3 million or in debt he isn't that much smarter (Edit: I mean as a percentage ..). It's always been like this. I am not ever jealous that people have luck and great success. But I am typically annoyed at how other people (press, pundits, media, bloggers) give them accolades that essentially reduce to 'wow this guy is really smart capable' w/o acknowledging any luck at all.
- disease 9y agoYou've got me thinking about the interplay of natural ability, hard work, luck and success. How unsuccessful could someone be if they were extremely talented and hard-working, but had little luck. How far can luck push someone with no ability or desire? I suspect luck plays a greater role in our lives then we are willing to admit, even though it can be mitigated to some effect.
- jacquesm 9y ago> How unsuccessful could someone be if they were extremely talented and hard-working, but had little luck. Homeless level bad. > How far can luck push someone with no ability or desire? Extremely far. I have seen examples of both, luck is a huge factor, and it comes in many guises (timing, circumstances, meeting the right person and so on).
- jpeg_hero 9y agoThis looks like a really easy marker that we've topped out on unicorn/big secondary market. When the smart big players start to take their chips off the table you can be sure this thing has peaked.
- zepto 9y agoOr it could have nothing to do with that, and be exactly what he says - he achieved what he set out to do and realizes that he now wants to do something else with his life, and has the time and resources to do so.
- nostrademons 9y agoMany times it's both: personal circumstances will make someone want to retire, but if things look good in the markets, they'll hold on for a year or two, and if things start looking tapped out that'll give them permission to step back. He's 2 years late, after all.
- BatFastard 9y agoAfter having founded a number of startup, I know how it is to be in an all consuming thing. I would imagine as a conscience VC you would have to feel all in on many projects.
- austenallred 9y agoNah. We were talking to lowercase three years ago and Mazzeo was already running the day to day for Sacca to spend more time with his family. This is a personal thing and has been a long time coming.
- FanaHOVA 9y agoPeople just have different interests. Why do you think only 1 person would leave if it was topped out as you say? All the other ones just want to waste money?
- ryanSrich 9y agoThese types of comments are always hilarious. Really? You think we've topped out on 1bn dollar companies in the year 2017? AI, Self Driving Cars, Improvements to Flying, SPACE!? You honestly think there's nothing left to invest in?
- staunch 9y agoHe's in the extremely privileged position to fund ten thousand people's potentially world-changing dreams. Instead, he's going to squander it podcasting in his pajamas. We need someone with the ambition Paul Graham had when he launched Y Combinator. Silicon Valley is still not a meritocracy. There are still tens of thousands of ambitious people not receiving funding. There's still no way for the early users of massive products to buy equity and lift themselves from the lower class. There is no greater lever in the world than technology, no better way to create technology than startups, and no more sure way to create great startups than by funding them.
- nolanbrown23 9y agoNo, he's not squandering anything. He's placing a higher value on time with his kids and wife than on time with an "ambitious" founder. No one deserves anything or is required to do anything.
- staunch 9y agoYes, of course it's his right to do whatever he wants. I'm just suggesting there's a moral imperative to do something when you can. "With great power comes great responsibility." "To whom much is given, much is required." That kind of thing. It's amazing how few people in Silicon Valley make a billion dollars and then go on to do anything useful with it at all. This criticism applies to the ten thousand people, like Sacca, that made a fortune off Silicon Valley and then "called in rich." What would you think of Bill Gates had he not put his fortune to good use?
- dmitri1981 9y agoChris Sacca's background story is little known and he talks about it at length with Jason Calacanis. The part about him losing millions while still at university is as shocking as his recovery from the setback is amazing. Check out https://www.youtube.com/watch?v=6VOQnK7O2To https://www.youtube.com/watch?v=6VOQnK7O2To
- rconti 9y agoGotta vote this one up so that everyone who reads the article knows it's Chris Sacca.. since his name is nowhere on the page and I'd venture most people don't know he's Lowercase Capital.
- aswanson 9y agoI think his story is funnier on this one, and he drops some foreshadowing hints here as to why Trump won, even before Obama's second electoral win: https://www.youtube.com/watch?v=iqUG2_cmZ6I https://www.youtube.com/watch?v=iqUG2_cmZ6I
- e40 9y agoI'm not going to watch a nearly 3 hour video to find that part. Please tell me the h/m index into the foreshadowing. Thanks.
- j_s 9y agohttps://youtu.be/iqUG2_cmZ6I?t=1h52m39s https://youtu.be/iqUG2_cmZ6I?t=1h52m39s feels close
- aswanson 9y agoThanks, but I was thinking more along: https://www.youtube.com/watch?v=iqUG2_cmZ6I&feature=youtu.be&t=2h32m24s https://www.youtube.com/watch?v=iqUG2_cmZ6I&feature=youtu.be...
- aswanson 9y agohttps://www.youtube.com/watch?v=iqUG2_cmZ6I&feature=youtu.be&t=2h32m24s https://www.youtube.com/watch?v=iqUG2_cmZ6I&feature=youtu.be...
- ghaff 9y ago>no better way to create technology than startups How did the Koolaid taste? You certainly must have drunk enough of it.
- staunch 9y agoYes, I believe in this whole technology "koolaid" thing. I'm sure you don't use anything created by startups in your daily life, like products from Google, Apple, Microsoft, Facebook, Twitter, Reddit, YouTube, Tesla, Ford, Amazon, etc.
- ghaff 9y agoApple and Google are startups now? Only in the sense that pretty much every company in existence was a startup (in the broadest sense of the word) once.
- staunch 9y agoYes, exactly. You don't get the output of a big Apple or Google without them existing initially as startups. Mark Markkula funded Apple. Andy Bechtolsheim funded Google. These didn't happen by accident. They weren't inevitable.
- ghaff 9y agoYes. And pretty much every product and service I use on a day to day basis was created by a company that was once small and may have received outside investment even if only friends and family. And just about every product and service has some technology component or innovation that differentiates itself. But now you're just arguing that companies build the products we use and companies start small which, while overwhelmingly true, is hardly a statement about the output of technology startups specifically.
- sillysaurus3 9y agopg answered your questions conclusively in http://www.paulgraham.com/growth.html http://www.paulgraham.com/growth.html
- canistr 9y agoHas anyone else noticed that a bunch of people leaving the investing scene/liquidizing in the past year are part of the same circle? Specifically Sacca, Tim Ferriss, and Richard Branson? I'm certain there might be more people.
- giarc 9y agoLeaving the investing scene and liquidating their positions aren't the same thing, and Chris didn't say anything about selling his stock.
- canistr 9y agoI'm not saying they're the same thing. But there is the appearance that they are effectively "getting out of the game". Not mentioning he is selling stock doesn't mean he hasn't sold some of it. Especially considering Sacca has a lot of Twitter stock and he's ridden the rise and fall from $90+ down to its current levels.
- paulcole 9y agoWhen was Twitter at $90+? I thought it peaked in the high 60s (USD)?
- adventured 9y ago$74.73 (Dec 2013) I believe was the public high
- econner 9y agoHe doesn't own any Twitter: http://dailycaller.com/2017/03/15/twitter-gets-its-worst-critique-yet-from-one-of-its-earliest-investors/ http://dailycaller.com/2017/03/15/twitter-gets-its-worst-cri...
- melbourne7 9y agoWell, perhaps. But Sacca is great at it. Ferriss pulled out because he's no good at it. (Easier to be a charlatan in books rather than investing).
- gfitz 9y agoName another VC that wears spurs
- rainbowmverse 9y agoI'd never heard of him before this since I don't pay much attention to VC. Introducing the person you're talking about is always a good idea when writing about them.
- Judgmentality 9y agoSometimes I think people in the Valley don't realize they live in a microcosm. I had never heard of Chris Sacca before Shark Tank, and I've raised venture capital in the Bay Area before.
- gfitz 9y agoJust making a joke about his distinct style. I should've put his name in the title but most of HN seems to be catching on.
- fao_ 9y agoI had never heard of Shark Tank, or any of the people mentioned so far in this thread until I stumbled upon a mispost somewhere on Hacker News. I don't get why people would watch that. The investors came off as idiots.
- Clownshoesms 9y agoHadn't heard of it either. Sounds like a very greedy guy that just has to blog about his trials and tribulations, and explain just how his greed is actually "drive" and "working hard". This VC kowtowing is sickening.
- derefr 9y agoThe title wouldn't instantly tip me off, because generally I would assume it was a metaphor. But yes, Chris Sacca actually wears spurs.
- 9y ago
- luhn 9y agoI just started listening to the Startup podcast, which features Chris in the first episode. He seems to be a very intelligent and talented guy while still remaining grounded. I wish him well with his future endeavors. Also, ten minutes after reading the article, I just realized the pun in the name "Lowercase Capital."
- giarc 9y agoIf you search his name in the iOS podcast app (and I imagine others) you'll get a list of podcasts where he is interviewed. I highly recommend it!
- arikr 9y agoWhat's the pun?
- fortenforge 9y ago"Capital" is a synonym of "Uppercase," so the name sort of means "Lowercase Uppercase"
- asciimo 9y agoI just made this connection when I was looking at their portfolio [https://lowercasecapital.com/posse/ https://lowercasecapital.com/posse/], and saw Gimlet Media. Lot of interesting stuff on that page.
- leftnode 9y agoI just started listening to StartUp as well (I like several other Gimlet shows) and he seems incredibly smart. StartUp is also a great podcast if anyone is looking for something to listen to (start from the first season).
- tdburn 9y agoThanks for pointing that out! I don't know how I missed it
- pdog 9y ago"As fate would have it, Jay's status appears to be at an all-time high, perfect time to say goodbye." https://genius.com/Jay-z-encore-lyrics https://genius.com/Jay-z-encore-lyrics
- thesmallestcat 9y agoThat retirement lasted all of what, a month?
- jtraffic 9y agoIt's interesting to think about this decision in the context of Nassim Taleb's writing. If you have a large sample of investors, some of them would be good just by chance. It's possible that Chris Sacca is not good just by chance, but we can't really know, and that is an excellent feature of walking away at this point. Most people will just tell themselves that Sacca "beat the game" and left. It could easily be that he got super lucky and realized it.
- oxryly1 9y agoTrue, and the only way to know more about the quality of his decision-making is to wait another 20 years and see where he's at.
- tyrust 9y agoIf he is as successful as he sounds he has probably liquidated enough to last for far more than 20 years.
- dwaltrip 9y agoOf course chance plays a huge role, but entropically speaking, the idea that all investors have equal skill seems a bit absurd. Now, whether "investing skill" is something that can be meaningfully distilled and taught to others is a whole different question. I think the answer is closer to "no" than "yes". The industry-wide distribution of the long term performance of fund managers seems to provide cursory evidence to support this.
- angersock 9y ago> As a rich white guy, being an activist/loudmouth in the #resistance often means taking up political positions that are against my own apparent self-interest. These oppressive zealots in the White House... > You mean beyond fighting a despotic regime... > I assure you, that’s not going to happen. Nevertheless, I am spending a great deal of time meeting with all of the beautifully spontaneous and decentralized organizations that have been popping up in the wake of our electoral calamity as well as dozens of candidates at all levels of government. I find so much hope in the new wave of leaders and builders who are standing up during these times and I want to be there to support them. I will have more to say about this in the days ahead, but, you know the drill. I'm sure that this is a common sentiment out in the Valley, but it's really kinda distressing to see people with access to so much capital writing with such melodrama. There's so much wrong at the local level--homelessness, education, people broke with medical problems--and yet these folks seem a lot more concerned with a strawman oppression.
- sulam 9y agoIt's not a strawman opposition when you see people you work with unable to re-enter the country, environmental leadership questioning the human role in global warming (or even the role of CO2 in warming!), members of organizations that openly identify with the Nazi movement as first tier advisors to the president, etc... This is not a strawman, this is real and it's worth fighting. So are the other things you mention, but everyone is free to pick their fight.
- angersock 9y agoEveryone is free to pick their fight, sure, but when people have accumulated great power there is great responsibility, no? And if these people come from a philosophical and cultural and political monoculture, I think it's reasonable to be suspicious about them. FWIW, I feel the same way about the energy execs and crooked politicians--except in the case of at least Trump, there is at least a mandate of government granted by the people that voted for him. Who, exactly, voted for these millionaires? Nobody.
- 9y ago
- brilliantcode 9y agoSo smart money is leaving startup/VC/SV...it'd be interesting to see who's been swimming naked all these years when the bubble bursts this Fall edit: oooh, definitely a touchy subject around here ;)
- mahyarm 9y agoI thought the bubble was going to 'burst' in 2012. I also thought the Vancouver RE market was going to burst 10 years ago too in 2007. And it still hasn't burst, it just flatlined and then kept on going. Bubble prediction is a difficult game to play.
- brilliantcode 9y agoFair enough. But this year is the perfect recipe. Trump, China, EU etc.... Read Antifragile book
- padobson 9y agotldr - compulsive gambler who won the Twitter lottery vows to quit playing the lottery and move on to making podcasts and buying political influence
- tommynicholas 9y agoChris won the Twitter lottery.... and the Uber lottery.... and the Instagram lottery..... and a bunch of other lotteries. Had arguably the best run of seed investing in history.
- socrates1998 9y agoIs there proof he got in early on all these and made money? I think it's been pretty established he got in super early on Twitter and made a ton of money, but I don't know about the Uber or Instagram. I sound like a hater, but just because you "invested in" those companies doesn't mean you made money or were a smart investor.
- mikeryan 9y agohttps://www.crunchbase.com/organization/lowercase-capital https://www.crunchbase.com/organization/lowercase-capital
- tommynicholas 9y ago1. He only invests early, so yes. 2. His fund for those investments went 213x http://fortune.com/2015/01/08/exclusive-is-this-the-best-performing-vc-fund-ever/ http://fortune.com/2015/01/08/exclusive-is-this-the-best-per... Possibly the best VC fund of all time.
- wand3r 9y agoI think it's public he owns Uber and owned it early. I think it's early to say if that was a "win"; I reckon he got in at a good val but Uber ain't public and w/ a braindrain, 2 lawsuits, likely death of their AI program, ceding China to Didi and public backlash idk if it's got legs. Chris made a lot of money and he did a lot of interesting things. He's interesting and a lot was luck and a lot was skill. That said, Twitter (if he exited a bit post IPO was the companies big win. You only need one though. Edit: Forgot about Instagram. He crushed it. Point is more Uber might not be as big, but his track record is amazing compared to other shops
- jakelarkin 9y agothe 2010-2015 era of generous outcomes for early-stage startups is over. No more easy follow-on rounds or acquisitions. Being VC becomes a lot harder so all these non-institutional personality guys - Sacca, Tim Ferris, Ashton Kutcher, and Russ Hanneman types are going to move on.
- sremani 9y agoA very nice write up ruined by very partisan ramblings in the end. There is nothing wrong in believing in liberal cause, but to consider the other side as devil incarnate is a bit disturbing.
- sandieman 9y agoI don't understand the logic that just cause someone is in a political party doesn't mean they can be evil and subsequently vilified.
- sremani 9y agoBefore answering the question, I would love to know what is evil in your words.
- JabavuAdams 9y agoIt's a personal post, why shouldn't he have an opinion? Also, how do you get to "devil incarnate"? The most negative thing he said was that the current administration are oppressive zealots. Note that he didn't specifically call out Republicans. The current administration has flouted norms, both Democratic and Republican.
- Domenic_S 9y ago"I think the institutions, principles, norms, and traditions that make the United States of America genuinely exceptional are at serious risk. It has been hard to think about anything else." "These oppressive zealots in the White House" "fighting a despotic regime" Of course he can have an opinion, and it seems like everyone's got one. It's less clear why the reader should care. And statements like this: "My career would not have progressed without the leadership and contributions of immigrants of virtually every race, ethnicity, and faith. Period." I mean, there are a lot of races, ethnicities, and faiths in the world, and not all of them care to immigrate. The hyperbole just smacks of virtue signaling, which some people enjoy and others don't. Depends on how you react to the signal, I suppose.
- brianzelip 9y agoAlways loved this website design whenever links to it get shared here.
- downandout 9y agoThe problem I have seen play out with friends that have tons of relatively easy money fall into their laps is that it saps ambition. Waking up every morning knowing that you have enough money for a hundred lifetimes can be freeing, but also means that you aren't required to do anything at all. Many people in that situation choose exactly that. My understanding is that Chris isn't the nicest guy in the world, so perhaps he's doing entrepreneurs a favor by backing other VC's. Some of his capital will still be out backing startups, but their founders won't have to put up with him personally.
- winter_blue 9y ago> I am spending a great deal of time meeting with all of the beautifully spontaneous and decentralized organizations that have been popping up in the wake of our electoral calamity as well as dozens of candidates at all levels of government. Does anyone know where (or how) to find these organizations? I'd love to get involved in some of these organizations that are trying to build a better future for our country, and try to contribute/help in any way that I can.
- jmcgough 9y agohttps://www.indivisibleguide.com/act-locally/ https://www.indivisibleguide.com/act-locally/
- gkop 9y agoCome work at Binti! We're a start up in SF, not working on politics or democracy per se, but are improving foster care in the US. Lowercase invested. https://binti.com https://binti.com
- lacampbell 9y agoI didn't know venture capitalists had to wear spurs.
- forgottenacc57 9y agoYes to ride their entrepreneurs.
- lacampbell 9y agoSomething about describing your retirement as "hanging up my spurs" bothers me on an unreasonable level. Unless you actually were a cowboy. I mean when I retire from IT work I hope I'm not going to tell people I'm "stowing away my space helmet and locking my plasma rifles in the cabinet".
- deleted 9y ago[deleted]
- gtallen1187 9y agoBeautifully written, thank you Chris!
- forgottenacc57 9y agoWish I was hanging up my spurs.
- ryandrake 9y agoWow, 42 years old, huh? Hard not to be a little jealous. Being pretty close to his age, it's maddening to think that with a different roll of the dice I might have been that person. Or I might have been unemployed and a heroin addict in Appalachia. Life seems so random and non-deterministic. Good on him. I sometimes wonder why more people who are insanely rich don't just retire and spend the rest of their lives doing something else...or doing nothing. I think of the C-level execs in my own company--they each have so much that they and their families for generations could literally do nothing for the rest of their lives and still continue to get richer via interest. Why go on working?
- sopooneo 9y agoOr rather, why not go on reading? There is enough great work in even a humble public library to fill a lifetime.
- given 9y ago> Why go on working? Because in the workplace they can abuse and mistreat people, play their power games etc.
- vacri 9y ago> Why go on working? Money isn't everything.
- badpenny 9y agoAnd, conversely, to some people money is everything and they can never have enough of it.
- deleted 9y ago[deleted]
- cmahler7 9y agoor he's a smart guy who put himself in a good position for success by getting into great schools and then making connections with the right people while at Google. You don't make the consistent home-run investments he has through complete luck.
- theprop 9y agoFantastic!! I feel that one feels most alive when you're involved in some struggle. And if you've really achieved a high level of excellence in your field...may be the right time to trying something new! Michael Jordan tried baseball! That said, I feel getting involved in political issues is mostly a losing situation because your power (even the power of the president as we've seen perhaps thankfully in the past 90 days is highly limited) to get something accomplished is so limited. Also, the solution to most problems is not new laws or new politics. I remember a professor at my college spent years getting the exam dates shifted three days earlier from a Tuesday to a Friday...that's the speed & work of politics, frustrating.
- joaomacp 9y ago>getting the exam dates shifted three days earlier from a Tuesday to a Friday. That's three days later. Or four days earlier.
- animex 9y agoI think he's hinting at something political but not running for office. I'm guessing some sort of involvement in the 2020 Presidential Campaign for some Dem or Alt candidate.
- joaomacp 9y ago>So we’ve been quietly backing the next generation of investors, but specifically women and people of color who have been starting venture funds. This sounds incredibly racist and sexist. Giving people advantages based on the color of their skin or their sex is unfair, and it's basically the definition of racism and sexism