Sep 2, 2016 ยท 6 minutes

The last four (plus) years of building Pando into a sustainable, profitable content company centered around long-form, adversarial journalism has not been easy.

We have had one pretty big advantage though: We cobbled together $4 million that we needed to pay fair salaries and try a bunch of things to get us to this point. But limiting the amount we raised to that level meant I still controlled the board and the majority of the stock.

But not owing anyone a board seat can be a blessing and a curse for a founder, I’ve discovered. We’ve had four board members over the course of the company’s history, other than me and a few observers. I’ve asked two board members to leave, one of those very publicly. The two other board members were so qualified and so successful in their careers, that they’ve had to leave us.

Lockhart Steele was incredibly valuable as someone who also raised a modest amount of capital and then slugged it out to build three successful content brands in Racked, Eater and Curbed. There was nothing I faced, he didn’t have a great perspective on.

Unfortunately (for me) he did so well, that his company was acquired by Vox. That wasn’t quite enough to convince Jim Bankoff he had to leave us, but when he was promoted to VP, in charge of all editorial from the Verge to ReCode, it clearly became too much of a conflict. And -- by the way-- both brands have gotten better under him.

Happy for him, happy for Bankoff, bummed for me.

Far sadder is news last week that Facebook is making Andrew Anker step down from our board.

Andrew was one of the first people I (and then-baby Eli) met with when I was thinking about building Pando. We talked about him being the CEO for a brief moment, before settling on him being our executive chairman.

Andrew was almost spookily suited to be Pando’s chairman. He’s definitely a connected Valley insider, but he relishes our fights. At our first ever team dinner he said he thought good media companies should piss off 20% of their audience everyday, the key was just rotating that 20% around. (This may be the only metric we’ve consistently over performed on.)

He has encouraged us never to cave to a legal threat, no matter how much high legal bills wrecked our budget. Every time there’s been a scandal around Pando and other investors have done this:


Andrew has taken this approach:


At every board meeting, he’s only encouraged us to be more adversarial and more combative. If you aren’t a journalist, you can’t understand how rare this is even in an editor much less a board member who has no visibility into the actual newsroom.

And Andrew’s previous startup was Tugboat Yards, a startup based around monetizing content through subscriptions. Obviously, that expertise came in handy when we shifted our business model a year ago.

Then there’s the fact that he was a banker and a venture capitalist. He loves making deals, he gets every intricacy of every term sheet. When I didn’t know the answer to a question, I never had to front that I did, I just asked him to explain it to me, or in some cases, just handle it. He helped secure for us for a price even we could afford.

But honestly, all of that hasn’t even been his real value add. As I’ve written many times (and am detailing at length in my upcoming book): Andrew was a perfect chairman for a first time CEO because he always had my back publicly but relentlessly kicked my ass in the boardroom. I’m not going to lie: I have been furious with Andrew at certain points during the building of this company. I have a four day panic attack before board meetings.

But that’s because he’s right: He has a sixth sense for finding my weak spot and zeroing in on it. I shouldn’t be surprised. One of our investors, Jim Currier, had Andrew on the board of a company he built once upon a time, and he put it to me thus: “Andrew is a great board member, because he’s fully in touch with his dark side.”

He was as good at advising me when we had millions in capital to play with, as he was advising me when we went into profitability/bootstrap mode. I can’t think of many people in Silicon Valley who have this skill set. Naming Andrew to our board was one of the top four decisions I made that have absolutely kept us in business.

Andrew wound up joining Facebook last year and is increasingly playing a top role with Facebook News. This was obviously a major conflict waiting to happen, and Facebook unfortunately made the call last week.

The point of this post is less about how amazing Andrew was -- although I don’t think great board members get enough credit in the Valley or founders even articulate what a great board member looks like. I don’t think it’s someone who just nods and agrees with me, but nor is it someone who tries to turn us into a company we are not.

The point is a frustrating underbelly of how connected and flexible the flow of talent is in the startup world. I had a .500 batting average hiring board members, although all four of them tangibly added something valuable to the company. Given the peculiar fit between a business, how it evolves, its personalities and a board member’s demeanor and skill, that seems pretty decent.

I’d say the majority of founders I know would tell you honestly and off the record that they are saddled with board members who vary between not-helpful or harmful. There’s a saying people like to say out here: “If I don’t listen to my board, I might get fired, but if I listen to my board, I definitely will.” There is a reason entrepreneurs have aggressively pushed towards board control being the norm.

But twice now, I’ve picked too well. The two board members who have worked out, did so because of their media chops that we valued so much. But because of those chops, they have subsequently have taken on larger roles in multi-billion companies and been forced to step down.

So what is the answer? Do I find someone who is successful, but not ambitious enough that they may change jobs? Do I shoot for another Andrew or Lockhart and just enjoy the year or years I may get out of them, the same way startups churn through management as a company evolves? Do I avoid my quarterly panic attack and just name pals or existing insiders to the board? Or do I try to find someone who will be as aggressive as Andrew?

The freedom of controlling my board is becoming a curse.