From YC to GV: #Silicon16 [and their respective rap songs: #VentureRap]
Y-Combinator (YC) - The accelerator formerly known as YC, or rather the accelerator now known as a seed-fund, or rather ... whatever you want to call it, it’s the hands-down best at what it does. Paul Graham built a phenomenon, a phenomenal phenomenon whose model has now been mimicked hundreds if not thousands of times over. Find the talent, teach the talent, be initial investors in the talent. And by investment, there’s far more than working capital at stake. You get the best of the best as your mentors, and a favorable valuation upon graduation. Not a bad gig, and well worth its weight if you are new to it all. Notable stat: YC companies have raised ~$3B and are worth ~$30B. Notable investments: Dropbox, Airbnb, Zenefits Rap song: Phenomenon (by LL Cool J)
Naval - Angellist personifies the new era of AWS-infused, a-few-grand-to-get-started, i-came-i-saw-i-conquered startups that are born out of a founding developer’s painpoint, and strive to blossom into the mighty rainbow-bright unicorns that are so often depicted these days. Naval is knowledgeable above all else. If this whole Silicon Valley story was an epic adventure, Naval would be the timeless oracle-like figure (youngish but older too) that people advise the newly-arrived hero entrepreneur to seek out. He’s tied in and there’s no bullsh!t. (Although Naval, I don’t know about timeless, get some sleep from time to time man!) Notable stat: Andreessen thinks he’s the new bird among old dinosaurs. #evolved (Oh and in terms of numbers, last year AngelList helped 243 startups raise $100M+ from 2,673 investors.) Notable investments: Twitter, Uber, Yammer Rap song: The World is Yours (by Nas)
Ron Conway (SV Angel) - The Godfather himself. He and Jay-z should get together for a remix of Big Pimpin’. It pays to be in early and with all. As the check sizes have shrunk in this numbers driven game, where it’s 1 out of 10 or more likely 20, no one’s played the odds better. Forget trying to choose, invest in them all! He’s as close to a one-man, seed-stage index fund as you’ll find. More times than not it comes down to what deal is Conway NOT in? Enough said. Notable stat: He invested in Larry and Sergey when their company was called Backrub, and he’s invested in over 600 companies overall. Notable investments: Google, Facebook, Twitter Rap song: Big Pimpin’ (by Jay-Z)
Chris Sacca (lowercase Capital) - I’ll see your Twitter, and raise you Twitter. All the way to the bank. And then to Truckee. And then to SoCal. And for his next trick ... I have no idea what Sacca is going to do next. But if I were to guess, it would be a Bilbo Baggins magic-ring disappearing act at his 40th 41st birthday party. Maybe go check into his own island in the South Pacific somewhere. De-stress, breathe deep[er], clean up. And then come back and maybe even take a page out of Branson’s playbook and start inviting his friends to come hang out on the island. Tony Hawk could build a skate park, there’d be a solid break out from the beach house, and certainly some type of Kiva integration. I bet he’s out to make the world a much smaller place, starting in Asia. Notable stat: Lowercase’s first fund of $8.4 million is set to return $1.3B. Notable investments: [Twilio], Twitter, Uber, Instagram Rap song: Flava’ in ya Ear remix (by Craig Mack, Biggie, Busta Rhymes, LL) [ya’ mean?]
Mike Maples (Floodgate Ventures) - Corky, zany, and as sincere as they come. He’s got street cred and you can find him around town taking meetings before anyone else. I respect the guy mostly because his companies trust him and speak highly. ‘Thunder lizards’ trump unicorns most every time, so I hear. Mike’s a default idealist seeking change. And hey, let’s not forget that’s what this place called Silicon Valley is all about. Notable stat: Add a 2nd ‘g’ to ggrab his attention (Digg and Chegg). Notable investments: Twitter, Twitch, Lyft Rap song: Shimmy Shimmy Ya (by Ol’ DB)
Steve Anderson (Baseline Ventures) - If SF has a Batman, I’m pretty sure it’s Steve. That’s why he never leaves that Marina HQ, there’s a whole underground BatCave complex with launch tunnel into the Bay and the whole deal. He’s chipper, calculated beyond calculation, and I’m pretty sure if you did your homework you could somehow trace Starbucks’ success back to him. (Just a hunch and it would probably take some innovative math.) Notable stat: He made a cool $100M in one day from Instagram. #icecold Notable investments: Twitter, Instagram (first investor), Heroku Rap song: Hey Ya (by Outkast)
Peter Thiel (Founders Fund) - The Valley’s resident philosopher. Be it through the Founders Fund, his Fellows or Foundation, or the PayPal Mafia legacy, this guy is one that defines Silicon Valley. Three of my favorite Thiel quotes: “This is always a problem with élites, they’re always skewed in an optimistic direction”, “Technology is the one way for us to escape competition in a globalizing world”, and "Just don’t fuck it up [in the beginning]." I quote him here because even after reading his latest book, I don’t really have a sense of who he is. Better for him to speak for himself I suppose. Few have taken a $10M to $7B ride and then back down again, I bet such an experience comes with/from far more than a contrarian slant on education and mortality. If it’s anchored in an unobvious TRUTH, no matter how severe the implications, he IS crazy enough to do it. Notable stat: Technology is doing more (1) with less (0). Notable investments: Palantir, SpaceX, Facebook (first investor) Rap song: Get By (by Talib Qweli) [One measurement of success for this post, hypothetically, in theory, could be if Mr. Thiel retweeted this as his second venture into the realm of ‘140 characters’. Pausing to marvel at the simplicity of its significance, hypothetically, in theory.]
First Round Capital - First Round takes services seriously, and their [holiday] content marketing is second to none. They make venture fun, and provide an invaluable role in bridging seed-stage to Series-A. Navigating that gamut can make all the difference, and there’s no shop I would rather have reppin’ me in the search/mission to the big time. Plus, there’s a pretty good chance that Phin will be doing all this in classic Air Jordan’s and doing his best so you can “fit a 6.5 and get AJ’s” too. Notable stat: Josh Kopelman may be #4 on the Midas List, but he also takes the time to point out he was #2 in the Nantucket Watermelon Eating competition a few years ago. #classic Notable investments: Uber (first inst. investor), LinkedIn (Kopelman), Square, Flatiron Rap song: Award Tour (by A Tribe Called Quest) [but I also can’t help but bring back the 2012 holiday video (Call me maybe, Gangnam Style)]
Union Square Ventures - Fred Wilson represents New York well. He knows who he is, and I respect what he says. Plus, he’s come a long way since his more militant MIT days, I’d go as far, dare I say, to suggest he may be mellowing out a little. Just throwing it out there, and perhaps both his blood pressure and insights are the better for it. Polishing faded jewels requires finding them, and finding them means knowing where to look AND also being able to identify ‘diamonds in the rough’ even when they’re just carbon under pressure. If I were say ... the US government for example, and wanted help mobilizing the private sector to help solve significant challenges in short[er] periods of time with [dare I also say] Elon Musk like efficiency, I would recruit USV. Not to mention if a favorable byproduct might be bridging SF & DC by way of NYC. In its essence: solve problems, make things. You can choose in which order. If someone takes the time to convey something in as few words as possible, take it as a compliment not an insult. #EmpatheticBrevity Notable stat: “A small collegial partnership that manages $1B across 6 funds.” Notable investments: Twitter, Twilio, Tumblr, Zynga Rap song: C.R.E.A.M. (by the Wu-Tang Clan)
a16z - Andreessen Horowitz started cracking heads in 2009, and if you’ve seen Marc.A’s dome, you can see why they usually win. The grey matter inside appears to still be firing at record rates as well, he’s built and continues to expand upon nothing short of a dream team. He’s another that defines Silicon Valley. If Thiel manages it, Andreessen builds it. And the firm he started with Mr. Horowitz is one that all the others pay attention to whether they like to admit it or not. “In the next [6] years, I expect at least five billion people worldwide to own smartphones, giving every individual with such a phone instant access to the full power of the Internet, every moment of every day.” Well alright, alright, alright. Notable stat: a16z is out to find the 15 tech companies a year that reach $100M in annual revenue - they account for 98% of the market cap of those that IPO. #winning Notable investments: Skype, Facebook, Twitter, Airbnb, Pinterest Rap song: Stronger (by Kanye West)
Accel - Jim Breyer’s place is among the best, a Marvel really. Yea, he lead Facebook’s A which turned Accel’s Fund IX into one for the record books, but on the other side of the equation in some ways he also lead Wickr’s $30M [privacy] round. That’s keenly anticipatory, keenly telling. And assuming he’s not a cyborg, which would probably violate some by-law or provision deep in the fine print somewhere, you would be pretty fortunate to add [your.co] to the long list of Boards he’s been a part of and advised. Good luck, superhero-level delivery will help and even be expected. You get what you put in, and if Accel is investing, that’s likely to benefit your output. Breyer has been at Accel since the 80′s, and in that amount of time a firm created in his image through the sheer action of doing is ... well, it’s how the future is made. Venture is home in a Valley called Silicon in a State called California, and yea, there’s a lotta’ love. Notable stat: Facebook raised a $12.7M Series A from Accel in exchange for an 11% stake that proved to be worth $10B at the time of its IPO. Notable investments: Facebook (lead A), Flipkart, Dropbox, Spotify, Cloudera Rap song: California Love (by Tupac & Dre)
Benchmark - If you want your VC to also be ready to play a game of pick-up basketball, this is the firm I would roll with. Why, because that’s how I imagine they roll. And with Fenton at point guard, and Gurley cleaning up in the paint, I bet they can pretty much always give you a game. Basketball is a sport about the fundamentals and Benchmark is that for Venture. ‘Last year messed around and got a triple-double’ sounds about right for Fenton’s record with Zendesk, Hortonworks, and New Relic. Their Domo story sums up the process well: (1) meet at [Davos] (2) present to the partnership (3) ink the deal then and there (if it’s a go) (4) receive funds within 3 weeks. [#boom] Minimalist egalitarian is how some somehow explain it. I think it can be described in another way too: believe in rising stars. Notable stat: Benchmark’s 8 funds have paid out $22.6 billion to investors. Notable investments: Twitter, Uber, Snapchat, Dropbox, Docker Rap song: Today was a Good Day (by Ice Cube) [shake ‘em up, shake ‘em up, shake ‘em]
Greylock - Reid Hoffman knows it’s a ‘Beautiful’ thing to ‘Get Lucky’, and it seems to me he’s pretty ‘Happy’. There’s no ‘Frontin’, he stays away from ‘Blurred Lines’, and if you’re lucky enough to be in his portfolio he’ll most certainly ‘Drop [the wisdom] Like It’s Hot’. Do us all a favor and listen, just listen. In fact, I wonder if Pharrell could make that one of his next songs: ‘Listen’. I’d say the network effects of Greylock itself are pretty superb, and here’s a little oldie-but-goodie gem that personifies why that network is so true. LinkedIn is trading at a market cap of $27.6B as I write this, all from the founding premise: “Find and contact the people you need through the people you already trust.” Notable stat: U2 and meerkat is a 1st. Notable investments: Facebook, LinkedIn, AirBnb, Dropbox, Docker Rap song: [Take your pick] (by Pharrell)
Kleiner - Haters gonna hate, no matter what their gender, and don’t let anyone tell you this ship hasn’t set course for better waters, not that it really ever left them. Perhaps less turbulent, but they never even had to adjust anchor. This new public face may even be here to stay, as they demonstrate not only do they have nothing to hide, but also realize that allowing the world to see how they conduct business is an asset. They’re as professional as they come, and oh yea, also home to one of the most successful VCs of all time. John Doerr doesn’t hate, he dominates (with a smile) at this little game named Venture. Notable stat: “Mike [Abbott] led the team to rebuild and solidify Twitter's infrastructure to eliminate ’The Fail Whale', growing the engineering team from 80 to more than 350 engineers in less than a year and a half, and scaling Twitter's architecture to support hundreds of millions of daily tweets.” Notable investments: Google, Amazon, Facebook, Twitter, Uber Rap song: Still D.R.E. (by Dre & Snoop) [Still Kleiner]
Sequoia - Wuzzup, I mean WhatsApp, alongside FireEye, AirBnB, and Dropbox make the trusty redwood Silicon Valley’s reigning king right now [and even beyond if you factor in Alibaba in China]. Smart enough to profit the most from YC, smart enough to have invested in Apple then and WhatsApp now. THAT shows resilience, the ability to adapt, and above all an unsurpassed effort to remain relevant. Jim Goetz is 450, 32, 1, & 0, and Doug Leone is ... a tough mofo. :) Notable stat: The startups Sequoia has backed since its founding in 1972 command $1.4 trillion in stock market value, equal to 22% of the Nasdaq (as of 4.14.14). Notable investments: Apple, Google, LinkedIn, WhatsApp, AirBnb Rap song: Mo’ Money Mo’ Problems (by Biggie, Puff, & Mace) [Stay humble, stay low]
Google Ventures (GV) - No one even comes close in the world of corporate venturing. Someone mention a $400M fund? Bill Maris has that set on auto-renew each year without lifting so much as a fundraising finger. Now THAT’s a beautiful thing. You call yourself data driven? #fuhgettaboutit Notable stat: “[We] just hope to 1ive l0ng enough not to die.” Notable investments: Uber, Nest, Cloudera, Nextdoor, Flatiron Rap song: Nuthin’ but a G Thang (by Snoop & Dre)
Wrap-up: Twitter, Dre, and you. That’s right, if there’s one company that has brought more of these guys together than any other it’s Twitter. That’s rather fitting because I think that’s Twitter’s best trait: accessibility and a common link/thread. Dr. Dre is an embodiment of how all of this can come together as he now works at Apple, the pinnacle pointed to more than any other Silicon Valley company. It’s only fitting that Venture Rap includes a trifecta of his work. And you, well you are now one better informed than I bet you give yourself credit for. Play on playa, and don’t let anyone or any check size change who you are and what you want to do. If that happens, odds are the check $ize is only going to shrink anyway. Like Nissan has the readiness to point out recently: “Be yourself, everyone else is already taken.” - O.Wilde
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[We’re all downstream, act accordingly.]