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Thumbtack’s marketplace for local services had impressive traction, but the monetization strategy was unclear. When Marco and Jonathan decided to go all-in on a new model—and shut down millions in recurring revenue—the bet paid off.

Marco, Jonathan and Bryan go back to those early days.

Marco Zappacosta
Co-Founder & CEO, Thumbtack

We knew we were going to raise a round at some point, and we started connecting with people. Bryan expressed interest right away.

Jonathan Swanson
Co-Founder, Thumbtack

When you’re pitching, you’re also interviewing the investors. Bryan got to the root of our challenge faster than anyone. We thought, “Wow, we could learn a lot from him.”

Bryan Schreier
Sequoia

I was at Google for six years before Sequoia, and spent some of that time working on local advertising. I always had a strong interest in local. Local is an enormous market, but at the same time notoriously difficult to crack. Going after local is almost always a kamikaze mission. Marco and Jonathan weren’t intimidated by that.

Marco Zappacosta

When you pitch VCs, most people are afraid to say “no.” We appreciated that Bryan and Sequoia were very straightforward. They said, “We like you, we like this idea, we love this market, we just don’t know how you’re going to make money.” And in retrospect, that was an accurate assessment.

Bryan Schreier

They didn’t have the business model nailed when we first met. However, I had a feeling we would eventually work with them. They are such a relentless and high-caliber team. I checked in with them regularly, and eventually Marco sent me an email that said, “I think we figured it out.”

Jonathan Swanson

Bryan took a bet very early. To his credit, he watched us and waited until the exact moment we were ready to scale up.

Bryan Schreier

I used the product—a lot. I called their customers to ask “What do you think about this Thumbtack thing?” I probably called fifteen professionals to really understand if it was working.

Jonathan Swanson

Our first meeting with Sequoia was mid-April. They made their intentions clear, we all went to dinner and talked things over, and we closed in early May. The speed and professionalism of the whole thing was very attractive.

Bryan Schreier

When I join a board, I set up weekly check-ins with the founders. My goal is to build the relationship and make it clear that we are available to help with anything at any time.

Marco Zappacosta

We were not excited about the one-on-ones. We didn’t do that with any other investors. At first you’re worried you’re going to have to do homework, or the investor is going to mettle. Now it’s something we look forward to.

Jonathan Swanson

It shows how much time Bryan and Sequoia are willing to invest in the business. One of the biggest challenges they helped us tackle was attracting and vetting executives. This is a place investors can be very helpful. They have lots of data points on things we only do once—like hiring a CFO or VP of Engineering.

Marco Zappacosta

The introduction is cheap and easy. The closing is hard. As an exec, you don’t have that many swings of the bat. Executives rightfully fear going into an environment where they can’t be successful because of the founders. Having somebody like Bryan say, “These are good humans. I’ve seen them work hard, and get smart, and change their minds.” That’s huge.

Thumbtack generates over a $1B a year in business for its 200,000-plus active, paying professionals.

Related Article Focus On Your Value Proposition
Thumbtack
A marketplace that allows people to find, vet, and book local services.
Milestones
  • Founded 2009
  • Partnered 2013
Team
  • Marco Zappacosta
  • Jonathan Swanson
Partner