Building Enduring Value and Hitting Incremental Gains with Benchmark’s Sarah Tavel | E1983

**Sarah Tavel** (0:00)
It's hard, like when you're a CEO, there's a learned ruthlessness that ends up happening, which is that you have these relationships with the people on your leadership team. And by the way, your leadership team has the people on their leadership team that you develop relationships with, that you want to be nice.
Five Temptations of a CEO is like an incredible book. Every CEO should read it. The thing about wanting to be liked is like an Achilles heel that we all as humans have. It's a very difficult thing to have a lot of these hard conversations. And so you have these executives and they are not pulling the company up with them. They're being pushed up. When you have too many of those, it's one of those things that even one executive for too long who's being pushed up with whom are not having a hard conversation really has these ripple effects that you always look back and wish that you had made a decision sooner and faster.

**SPEAKER_2** (0:56)
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**Jason Calacanis** (1:38)
All right, everybody, welcome back to this week in startups, really excited to have Sarah Tavel back on the program. She's a partner over at Benchmark. I think she got there on 2017 Before that, she was at Bessemer. Before that, she was at Pinterest for a little bit. And I think you found out about Pinterest when you were at Greylock, because you did the investment and then you joined the company, right, Sarah?

**Sarah Tavel** (1:56)
Almost Bessemer is when I found Pinterest. And then from Bessemer went to Pinterest.

**Jason Calacanis** (2:02)
That's your big win, right?

**Sarah Tavel** (2:03)
Details, details, yes.

**Jason Calacanis** (2:04)
That's your big win.

**Sarah Tavel** (2:06)
It was a fun one.

**Jason Calacanis** (2:07)
Yeah, I mean, incredible. I actually had dinner with the founder recently. It was really sweet.

**Sarah Tavel** (2:11)
It's great.

**Jason Calacanis** (2:12)
Anyway, just to give a little brief intro here, I think looking at Benchmark, looking at your career, it's really been interesting to watch how the venture capital game has changed. You and I have been in it actually about the same amount of time, about a decade or so. And all these firms are raising larger and larger funds and Benchmark is just so disciplined. I read in the papers and the trades that you're just closing a fund. I'm not sure if you can talk about it or not. I know there's a bunch of rules around that, but I think the latest fund is 425, yeah?

**Sarah Tavel** (2:40)
Yes.

**Jason Calacanis** (2:41)
In my notes here, it says back in 2004, fund five for Benchmark was 400 million.
So a lot of discipline on having a specific size fund and a specific type of fund. And so welcome back to the program, Sarah Tavel. How are you?

**Sarah Tavel** (2:56)
Good to see you.

**Jason Calacanis** (2:57)
Good to see you. I love having you on every six months because you're dynamic, you're doing a lot. Let's start with the fundraise. Were you involved in it? Or is it just Benchmark is such an institution now that everybody just send them an email and they're like, yeah, we're in. And they just give you the ticket size. How does it work at a legendary fund?

**Sarah Tavel** (3:14)
We're very lucky to have a great group of partners that have been with us for a long period of time. And so when you are not expanding the fund, the core fund, it makes that process a lot more efficient. And so it was just a nice, nice, efficient process. And we're excited for the group that we have moving forward.

**Jason Calacanis** (3:34)
Do you get involved in it as a GP or is it just like so set up that you don't need to like do that part of the gig?

**Sarah Tavel** (3:41)
We're all involved in some way. You can think of it as like divide and conquer. We just had our annual meeting. So it was all timed in a way that made it particularly easy.