How I Made It: Thumbtack’s president left the White House for Silicon Valley

Jonathan Swanson left politics because he believed he could have a greater impact on the world through tech.

The gig: Jonathan Swanson, 34, is the co-founder and president of Thumbtack — a services marketplace that is sort of like the Yellow Pages of the digital age. Instead of trawling through hundreds of listings for plumbers, electricians, masseuses and tutors on paper, customers tell Thumbtack what kind of professional they’d like to hire, and Thumbtack presents them with options that fit their criteria. The 8-year-old company has on its platform more than 250,000 professionals.

Dinner table politics: Swanson was interested in politics from a young age, aspiring while he was in high school to one day be an economic advisor to the president. “It was very specific and very dorky, but I saw politics as this big platform for making the world better, and economics appealed to me because it felt like there was some science behind it,” he said.

Swanson didn’t come from a particularly political family — his father worked in IT and his mother was a teacher. He was born in Oklahoma and grew up in Iowa and Minnesota. What perhaps primed his interest in politics was the family’s dinnertime conversations. “I didn’t learn that thing where they tell you to not talk about politics at the dinner table,” Swanson said. “We always talked about politics at the dinner table.”

Yale and the White House: Swanson’s interest in politics didn’t wane in college. He studied politics and economics at Yale University while interning at the White House. He became passionate about Social Security, forming a nonprofit organization after his internship was over that galvanized students to advocate for Social Security reform. He was able to recruit more than 10,000 students across 300 college campuses to get involved, catching the attention of his former boss in the White House.


In 2006, fresh out of college, he was hired to serve as an economic policy analyst to the George W. Bush administration.

Conquering fears: Swanson didn’t know it at the time, but his experience in the White House was priming him to become an entrepreneur. In addition to thinking and learning fast, he was thrown into intimidating situations, not too dissimilar from venture capital pitch meetings.

“My boss would ask me to go brief the chief of staff or a Cabinet member on a new Federal Reserve policy, and if I knew nothing about it, I’d have to go figure it out,” he said. “I grew up shy and was the kind of kid where I’d think of what I was going to say in school a couple of times before I raised my hand, and half the time the topic had moved on. I couldn’t imagine standing in front of other people, giving them briefings. It was scary, but once I broke through, it was this amazing experience.”

Choosing Silicon Valley: For all that the White House taught him, Swanson knew after three years that it wasn’t where he wanted to be. “Politics is a circus, and I just wanted to have a big impact on the world,” he said. He also didn’t like that politics was a zero-sum game — that someone either agreed with you, or they were perceived as the enemy.

In tech, meanwhile, he saw potential to have an enormous impact on the world, while also being collaborative. “What really attracted me to tech and ultimately to Thumbtack is it’s not zero-sum,” he said. “You come out to San Francisco and it’s so collaborative. Even competitors get dinner with each other.”

Thumbtack: Swanson co-founded Thumbtack in 2008 with Marco Zappacosta with the view of solving a problem that affects lots of people: finding and promoting services. “Around 100 million people around the world earn their living providing local services, but no one had reimagined how you could hire professionals,” Swanson said. “The Yellow Pages has been around for 100 years and hasn’t really changed. You still see people taping fliers to poles.”

Their solution? A two-sided marketplace in which customers could tell Thumbtack what kind of service they need, and professionals could pay to send those customers messages and quotes. “Eventually we want to help with scheduling and invoicing too,” Swanson said. “We should be able to take that off your plate. As we do that, it’ll make small business much more accessible to everyone.”

42 rejections: Thumbtack’s early days were not without challenges. Swanson recalls pitching 42 investors shortly after he moved to San Francisco, and receiving 42 rejections. He chalks up Thumbtack’s success to the founders’ and employees’ persistence and, to some extent, ignorance. “If you knew how hard it would be, if you knew it’d be a 100-mile walk through the desert, you’d never do it,” he said. “But if you think it’s going to be five miles and you start, once you’re five miles in, there’s no turning back.”

The company eventually secured funding from big-name firms such as Sequoia Capital, raising a total of $273 million. The company is today valued at $1.3 billion.

Advice: “Find something you really care about, that has a real impact in the world,” Swanson said. “And then commit to it. We’re eight years in now, and we’re only getting to the interesting part. Having impact takes time. It’s not a two-year thing. It’s a decade plus.”

Personal: Swanson lives in San Francisco with his wife, Katherine. He likes trail running and biking.

Twitter: @traceylien