Sarah Tavel on Sourcing the Pinterest Series A Deal and The Danger of Being Founder Friendly

Sarah Tavel is a partner at Greylock Partners where she focuses on investing in consumer startups and companies that aim to consumerize IT. Before joining Greylock in 2015, Sarah was one of the first 35 employees at Pinterest. Prior to Pinterest, Sarah worked at Bessemer Venture Partners for 6 years and co-lead their Series A round in Pinterest.

Recently, Sarah chatted with Harry Stebbings on the 20 Minute VC and talked about how she sourced the Pinterest deal for Bessemer Venture Partners, how she provides value to the companies she works with, and what consumer products need to be successful. The 20 Minute VC is one of the best places to learn about venture capital. You can listen to the full episode with Sarah here.

Sarah Tavel

How Sarah Sourced the Pinterest Deal

I met the founders of Pinterest when they were working on the precursor to Pinterest, a company called Tote. I remember meeting Paul Sciarra (one of the co-founders) and thinking that he was a really smart, thoughtful guy. But, I wasn’t very excited about Tote.

Then, a few months after meeting Paul, one of my friends invited me to use Pinterest. I remember logging into the platform and thinking of it as an “ah ha” moment. It was so different than everything else I was seeing at the time. This was a time when Twitter was growing like crazy. So, there were tons of consumer Internet sites that were very text focused.

With Pinterest you had a product that was so visual. The list was normally a side feature for all the other social companies at the time. Yet, it was the central feature of Pinterest. When Pinterest came out I had been spending a lot of time in the ecommerce world. I was working with one of Bessemer’s investments, Diapers.com. Bessemer also had a lot of investments in the user generated content side of things. These were companies like Yelp and LinkedIn. So, I really believed there was an opportunity to bring those two worlds together — a social commerce.

I had been looking for a company that brought ecommerce and user generated content together. And Pinterest did it in a way that was so special and so much better than I ever imagined. I liked it as a company from the beginning. Then, it was one of these lucky things where I already knew the founding team. So, as the company grew I reached back out to them.

When we invested, it was a 5-person company with tens of thousands of users. It was super early and we got lucky.

Working with Founders: Why Sarah Joined Greylock Partners

Venture is an incredible privilege. I loved working at Pinterest. The work that you get to do as a product person in a company like Pinterest where you feel so passionate about the product is very unique. But, the number one thing I love about venture is I get to work with founders all day long. I think founders have such an unique DNA as people. In fact, I am married to one. So, I guess you could say I put my money where my mouth is. Founders are special people in that they see the future they want to create in the world and then make that happen from nothing. I get energy from working with those types of people. Plus, I also love helping to make a founder’s vision a reality. The fact that as a venture capitalist you get to do that all day long is an incredible thing.

Learning in an Operations Role Versus a Venture Role

As a product person at Pinterest I was executing all the time. When you’re executing that much, learning is a positive externality of your execution. On the other hand in venture, I feel like I am actively learning all the time. Meeting with new companies means learning about the spaces they’re in. It’s almost like a problem I need to solve or a puzzle to put together. I love that process. Ramping up on a company, figuring it out, and getting to know the team. To me, that is a lot of fun.

Why Being “Founder Friendly” Isn’t Necessarily a Good Thing

I actually don’t think of providing value to companies as being founder friendly. Often times a founder really needs someone outside the company to ask the hard questions, be a truth seeker, or push them in some way. Sometimes when I hear “founder friendly” I think of just saying “yes” to everything that the founder wants to do. But, that’s frankly not a great situation for the company or the founder. So, I see my job as being the person who will constantly reevaluate and reassess the core assumptions of the business. I also want to make sure we’re asking the right questions in the business and making the right decisions moving forward.

How Sarah Measures Her Success as a VC

My personal KPI is being the first person that the CEOs I work with call when they have to think through a problem or need advice.