‘Silicon Valley’ Boss on Season 3, Mark Zuckerberg and Ex-Twitter CEO Dick Costolo

Poor Richard. When Silicon Valley returns Sunday night, the fictional Pied Piper CEO, played by Thomas Middleditch, will have his work cut out for him.

The HBO comedy, co-created by Mike Judge, picks up right where it left off at the end of season two, with the programmer having just been ousted from his own company. Now in season three, he has to fight to regain his rightful place as Pied Piper’s CEO. But securing his former position might not be so easy when a new and more seasoned CEO (Stephen Tobolowsky) takes over.

“There’s no shortage of these stories. There’s a running joke among these seas that it’s never too early to fire a founder,” says co-showrunner Alec Berg of the inspiration for the storyline. “We hear over and over again that people literally create things that are too valuable for them to be a part of anymore.”

Ahead of the season’s debut, The Hollywood Reporter caught up with Berg to discuss what it was like to have ex-Twitter CEO Dick Costolo in the writers room, which Silicon Valley icon has been spotted in a Pied Piper T-shirt and other tech players we might see pop up in the show this season.

Will this season pick off where season two left off, with Richard ousted from Pied Piper?

Yes, Richard is battling for his life and also for the soul of the company. At the end of season two, they thought they had it made and then the rug got pulled out from under them. We have to kind of play that hand. So Richard’s no longer in control, and that’s where we’ll pick up. Essentially the arc of the season is that Richard is on the outs. Does he fight his way back into his company? Does he leave and start a competing venture? Does he make peace with whomever is brought in? Does he battle that person? Those were all the questions we were asking [when we started writing] the season.

What inspired the Richard-on-the-outs storyline?

Well, it happens to people all the time. It’s funny, we do this annual trip where we meet with a bunch of startups and founders and engineers and VCs and lawyers and all kinds of people. We’ve toured Twitter before, we’ve gone to Google, Facebook, Quora, Dropbop, etc. But when we went up to San Francisco to do research for season three, what was really funny was when we were asking engineers if the company would go on without him, they were all like, “Well, no. There’s no company without Richard! They would never do that.” And then when we met with venture capitalists and asked them, “So would you encourage the company to go on without Richard?” They were like, ‘Oh yeah, we do that all the time.”

It’s one of those things that is funny about this show. There are people who screen capture things and go on Reddit and scream about, “Oh, they got that colon wrong,” or, “Oh, they would never have done that.” But there are just as many people that argue stridently the other way — and they’re all experts! So even the experts don’t agree. That was the most freeing thing. When we’re like, “Gosh, what would really happen?” And then you ask two different people who actually work in that business and they had two diametrically opposed answers. So we just feel free to do whatever we want because we can always justify it with at least some of our expert viewers.

So Richard’s firing wasn’t modeled after what happened to Dick Costolo?

No, I think they were completely independent. There’s no shortage of these stories. There’s a running joke among these seas that it’s never too early to fire a founder. We talked to a few different people who had started a company that had exploded in size, and then the board of the company decided that it had exceed the size at which they were comfortable leaving that person in charge of it. And we hear over and over again that people literally create things that are too valuable for them to be a part of anymore.

We had a really interesting conversation with Andrew Mason, who founded Groupon, who very famously was fired. He was very forthcoming about what happened. Groupon at one point was the fastest growing company in the history of the universe. It just exploded into this thing that was so massive that the board didn’t feel comfortable leaving him in charge. A lot of times it happens where somebody who is product-based is not as well-versed in running a big company or managing teams. In general, engineers are good at things, not people.

How did Costolo end up consulting on the show?

He found himself oddly out of a job and was looking for something to do. He digs the show and he started off as an improv performer. He’s a funny guy who appreciates comedy, and I think he had a fondness for our story, so he just offered. He would come down and sit in our writers room on Mondays and Tuesdays and was super helpful. We have consultants but the process is very slow sometimes. You’re sitting in the room and you’re like, “Well, what about this idea? Alright, let’s call the consultant. Let’s see if he could get in touch with somebody who could tell us whether that could actually happen or not.” Whereas when you have a guy like that in the room as you’re talking about it, you’d go, “Could this happen?” So the lag time is almost zero and it makes it a lot easier to get stuff done.

What topics was he particularly helpful with?

As a guy who has actually run a big company, he has a lot of perspective. He had an enormous amount of insight into, “This is how they would treat this.” He knew what engineers did but he also understood shareholders and the forces at work in a board meeting. The scope of his knowledge [is impressive] but he’s also just a funny guy. He has a healthy skepticism about himself and he’s very self-deprecating. If you sat in that room for a half an hour and you didn’t know anybody, I don’t think you’d go, “Who’s that arrogant prick sitting at the end there?” He’s just another nerdy comedy writer just like the rest of us.

Wait, Mark Zuckerberg has been seen in a Pied Piper shirt?

Somebody told us that, yes, occasionally Mark Zuckerberg comes to the office wearing a Pied Piper shirt.

Has he ever reached out to you guys about the show?

No. I guess he has other things to do than try to get on our jerky little TV show. Apparently he has a multi-billion dollar company that he runs with most of his wakening hours.

You’ve approached a number of tech players for cameos, but have any of them reached out to you?

Yeah. I’m not going to say who but we’ve had a couple of people reach out and sort of go, “Hey, I would be willing to grace you with my presence.” And we’ve actually had a couple people pitch us ideas of how they wanted to appear on the show — and they almost, without exception, are jaw-droppingly not at all what we do, and their sense of who and what they are and what their value to the show is massively off kilter.

Which, I’m sure, only makes you feel better about all the ways you skewer Silicon Valley in the show, yes?

Suffice it to say, it’s affirming. I feel like when we’re doing a show about people who are not self-aware, it gives me faith that we’re on the right track.

What other cameos can we expect to see this season?

Dick Costolo is in one playing himself. There’s a few others: [Zynga founder] Mark Pincus and [Yelp’s] Jeremy Stoppelman, too.

Still no Elon Musk?

I’d love to have him on the show, but I don’t think that Elon Musk spends an enormous portion of his day thinking about our show [laughs.] He’s trying to go to Mars.