Apr 5, 2016 ยท 7 minutes

Last week, I filled out the first round of CB Insights ultimate “fantasy Series A investor” bracket. I mostly agreed with the crowd, with a few notable exceptions like picking Kleiner Perkins over Lowercase Capital.

Here are my picks from round two. This should be when the fur starts to fly.

Sequoia v. BV: I said it was rude to put Slow Ventures up against the most dominant VC in the history of Silicon Valley last week, and it’s just as mean to match up BV with them. Recent scandals and prickly rep aside, no way Sequoia doesn’t win this.

My Pick: Sequoia

Matrix v. Founders Fund: I voted for Matrix in round one as I’ve never had negative dealings with them, but I know Founders Fund far better. Founders Fund invested in us and have always been one of the more responsive, professional and supportive firms we’ve worked with. I also like that Founders Fund likes to back companies most VCs would shy away from.

My Pick: Founders Fund

Intel Capital V. General Catalyst: I voted out Intel Capital last round because they are supposedly liquidating their portfolio. General Catalyst, duh.

My Pick: General Catalyst

Floodgate V. GV: I also voted against GV in round one, because of the way they’ve treated entrepreneurs in the past, such as taking the moral high ground in some cases, while abandoning it if far grosser ones. Worse: Classlessly trashing entrepreneurs once they’d already fallen from grace. Floodgate on the other hand is one of the most consistent and principled firms in the business, in my view, and has one of the better track records for funding and hiring women. This one is easy.

My Pick: Floodgate

Andreessen Horowitz v. Bain: Andreessen Horowitz isn’t a Pando investor, but Marc Andreessen is and he’s always been the single most responsive investor whenever we needed paperwork returned or questions answered. Not only that: We have ruthlessly criticized companies he’s been involved with or people he is professionally close to and he’s never once asked us to pull a punch. He knew what he was doing investing in Pando, and has always respected the role of an independent press.

My Pick: A16Z

NEA v. Menlo: I don’t have super strong feelings about this one, but I’d go with NEA simply because of their reach and deep pockets. But I’d pick partners carefully: There’s a lot of inconsistency in any mega fund.

My Pick: NEA

Social Capital v. Lowercase Capital: I voted Lowercase Capital out in round one for a simple reason: Even entrepreneurs and CEOs that have made Lowercase Capital insanely wealthy no longer speak to or hold Chris Sacca in high regard. I’ve never seen that in my near 20 years covering this industry. As an entrepreneur you don’t simply exist to make someone rich, you are trying to build your vision. If someone betrays you or makes your life miserable that miserable on the way to “success,” it’s not worth it. If you put a donkey next to Lowercase Capital, I’d pick the donkey. It helps, in this match up, that I also respect Social Capital a great deal.

My Pick: Social Capital

Index V. Greylock: This is hard because these are two of the firms and partnerships I respect most. So much of this comes down to the hypothetical company that’s taking this Series A. If you need a firm with a global mindset, it’s hard to do better than Index. If you are doing enterprise software, Greylock has one of the best track records. Likewise, if you are doing consumer Internet, it’s hard to get much better advice than Reid Hoffman or David Sze. It’d come down to partner, and fit. But ultimately, I’m going to give the nod to Greylock, because I think they care slightly more about backing good people, even if bad people would make them richer. Index, after all, funded Secret, a company with no redeeming value in the universe.

My Pick: Greylock

USV v. Thrive: Hard to vote against USV, the firm that pioneered so much of the New York Tech community. Also, I like that prickly Fred Wilson calls it like he sees it, no matter how uncomfortable it might make everyone, or how much at times we disagree. You always know where you stand with Fred, which is rare in this business.

My Pick: USV

Greycroft v. Highland: Don’t have strong feelings here. I’ve heard good things about working with Greycroft, and don’t hear a lot about Highland these days. That said, I voted for LHV over Greycroft in round one. So in my world, they would have already been out. So I should stick with Highland, right?

My Pick: Flip a coin

Upfront V. Foundry: This is hard…. former Pando alum Michael Carney works at Upfront and he’s one of the hardest working, most loyal people who’s come through our company. I have a hard time voting against any place that he’d join. But I believe the rainmaker/lead partner sets the tone at a firm, and I’ve had my ups and downs with Mark Suster. (For instance, he amplified this post on social media, which most people felt was pretty gross and was clearly dishonest. Hard for me to get past victim shaming or woman shaming of any kind, whether it’s me, another female founder or any woman. At a minimum it shows a callous disregard for how women are routinely treated in this industry.) Brad Feld on the other hand is intensely loyal and committed to entrepreneurs, and cares deeply about the emotional toll of being a founder. He’s a dream Series A investor, especially for a first time founder.

My Pick: Foundry

IDG Ventures v. Firstmark: Not strong feelings about either. IDG is more international; Firstmark is more New York centric. Depends on your priority and gut feeling of partner.

My Pick: Flip a coin

Benchmark v. Spark Capital: One thing that makes writing these posts such a thankless task is how personal all of this is. It largely comes down to chemistry, past experiences and what I’d consider best for the kind of relationship I like to have with my investors. Benchmark is unquestionably one of the top two or three firms in the Valley right now. But when I look at the way their CEOs— whether Travis Kalanick, Sean Rad, or Evan Spiegel— have spoken about or treated women with little to no repercussion, I feel physically sick.

Now unlike some other firms on this list, Benchmark has been very careful never to publicly applaud these actions or excuse them. But at some point new companies are getting the recycled capital of the previous hits. I’m not comfortable taking money built off misogyny and threats to female journalists, even if I wasn’t one of the journalists in question. So for me, and my ethics, I’d pick Spark, which is also an excellent firm. Although I get why most founders would slit someone’s throat to get to work with Benchmark.

My Pick: Benchmark

Bessemer v. Lightspeed: This is an interesting match up because I respect Jeremy Levine of Bessemer and Jeremy Liew of Lightspeed. Both are thoughtful investors, who think about where industries are going, not merely react to incoming deals. I’d give a slight nod to Liew and Lightspeed, because they called the rise of LA before any other Valley investor.

My Pick: Lightspeed

Khosla v. First Round: First Round. Khosla is too prickly for my tastes. First Round is pretty much the opposite of prickly.

My Pick: First Round

True v. Accel: I have a lot of respect for several of the True Partners, but Accel has a track record not only of backing great companies, but backing great bootstrapped companies who aren’t based in the Valley. They are probably the least lemming of the major Valley firms. And they are another example of a Pando investor that has stood by us, even when we’ve gotten into scraps with their much larger investments and it wasn’t easy for them.

My Pick: Accel