Mar 31, 2016 ยท 6 minutes

Yesterday I decided to totally unnecessarily piss off a lot of VCs by publicly weighing in on CB Insights VC bracket. It was so long I only did the left side. Here’s the right. 

The first round of voting is already over, and CB Insights audience mostly got their picks right. (Read: They agree with me.) 

Tomorrow I’ll do round two... when it gets really interesting. 


USV v. Mosaic Ventures: USV. Some of their hits included companies that have seen better days like Zynga, Foursquare, and Twitter. Still, Fred Wilson is the godfather of NYC VC. More than that, he’s a straight shooter in an industry of people who don’t want to take stands or ruffle feathers. 

My Pick: USV

Crowd Pick: USV

RRE Ventures v. Thrive Capital: I don’t know RRE Ventures… at all. And I don’t necessarily have anything negative to say about Thrive. So I’d go with Thrive. But if I were actually raising money I’d express concerns about Josh Kushner’s ability to add value as an investor at the same time he’s building an ambitious startup in Oscar. I know a lot of VCs believe they can do both. But historically the best ones do not, or they greatly curtail one of the roles or another. 

My Pick: Thrive Capital

Masses Pick: Thrive Capital


Greycroft v. LHV: Easy one for me to pick LHV. For one thing, I’m a "content" CEO and this is possibly the only firm that really believes in, bets on and builds value in content. Secondly, I raised money from LHV and would again. I’ve had a good experience. Third, Ken Lerer is the only major VC that I saw publicly rebuke Uber after they threatened my family. As you may have learned from yesterday’s bracket, having the balls to tell the truth and take a stand goes a long way with me. It should with most entrepreneurs: Supporting you won’t always be popular or consensus.

My Pick: LHV

Crowd Pick: Greycroft


Highland Capital Partners v. Atomico: I don’t have strong feelings about Atomico. The only strong feelings I have around Highland are around Dan Nova. When I was working on my book about emerging markets, he was kind enough to take me to Rwanda with him. His passion and interest in places that aren’t the US aren’t exactly seen everyday in the Valley. He’s a guy I’d want fighting for my company. 

My Pick: Highland

Crowd Pick: Highland


Upfront Ventures v. Accomplice: I don’t always agree with Mark Suster. And a lot of people don’t care for him. But again, that’s a sign he’s being outspoken and taking a stand which I like. And former Pando west coast editor Michael Carney works there now, so major points for his judgement in parters. 

My Pick: Upfront

Crowd Pick: Upfront


Foundry Group v. Founder Collective: This is a hard call, but since Chris Dixon went to A16Z it’s easier to pick Foundry Group. Brad Feld in particular cares a great deal about the parts of entrepreneurship that many people don’t want to talk about. Depression, the toll on a marriage, the impact it takes on you. A good guy to talk to when the shit hits the fan. 

My Pick: Foundry

Crowd Pick: Foundry


Balderton Capital v. IDG Ventures: You probably wouldn’t be weighing these two if you were a US company. If  you were in Europe, Balderton is one of the best firms you could pick. So, uhhhh, Balderton I guess? This is a weird bracket. 

My Pick: Balderton

Crowd Pick: IDG Ventures


Firstmark v. TOTALLY UNREADABLE LOGO: Honestly, VCs need some logo work. I have no clue what the other company is in this bracket. Uh….

My Pick: Abstain

Crowd pick: Firstmark


Benchmark v. Lux Capital: This is the meanest thing CB Insights has done since it paired Sequoia against Slow Ventures. I don’t always agree with Benchmark LINK TO MATT COHLER THING. But I respect that they still do venture capital “classic.” And it’s unquestionably one of the best firms in Silicon Valley. 

My Pick: Benchmark

Crowd Pick: Benchmark


SV Angel v. Spark Capital: This is easy only because SV Angel is more of a seed stage firm than a series A firm. Spark adds a ton of value and has carved out an impressive portfolio out of Boston— a city that most people believe New York has eclipsed as the East Coast venture hub.

My Pick: Spark

Crowd Pick: Spark


Lightspeed Venture Capital v. Innovation Endeavors: I’m a huge fan of Jeremy Liew. He is the thinking man’s VC, articulating an investment thesis that isn’t just UNICORN! GROWTH! YC DEMO DAY! He was the first to go long on LA. Shoe Dazzle may have blown up in his face, but Honest and Snapchat certainly haven’t. 

My Pick: Lightspeed

Crowd pick: Lightspeed


Khosla Ventures v. 500 Startups: Keith Rabbis and Vinod Khosla aren’t everyone’s favorite dinner party invitees. And I respect that Dave McClure has worked to invest in international markets and black and female founders. Still, I prefer VC classic, not so much the broad spray and pray approach. So if it were my company, I’d probably pick Khosla. But we’d never get out of a board meeting as Rabois and Paul Carr’s Twitter fights would turn into a live show [And as usual, I'd win -- PBC]

My Pick: Khosla

Crowd Pick: Khosla


First Round v. Data Collective: Hard one as Josh Kopelman and Data Collective are both Pando investors and both have been very supportive of us. I’d have to reluctantly pick First Round. I think their value added services— like their Quora like site for founders— indeed add a lot of value. Also, the Holiday video. And even though their biggest hit is Uber, they’re remarkably nice guys. 

My Pick: First Round

Crowd Pick: First Round


True Ventures v. Foundation Capital: As I said before, I’m not a huge believer in the building a company and being a VC double dipping, which is core to a lot of True’s model. But I am a big fan of Jon Callahan and many other True Partners. And Foundation is one of those firms that’s better days are likely behind it. 

My Pick: True

Crowd Pick: True


Accel v. Sherpa Capital: Also both investors in Pando. And yet, unlike First Round and Data Collective, a super easy decision. Accel has never openly supported a company that has threatened my family. They’ve not only supported Pando as a portfolio company, but have sponsored our events before to because they believe in what we do, even if it isn’t always easy for them. Even if Accel wasn’t a top firm, I’d pick Accel from my personal experience alone. 

My Pick: Accel

Crowd Pick: Accel


Next round tomorrow!