Kristen Anderson began 2019 in limbo.
It seemed like her Cambridge startup was on the brink of running out of cash. A client owed her $450,000, but there was no sign of a check being cut. She and her cofounder, Andrew Ambrosino, had spent most of the previous six months trying to raise money from venture capital firms in Boston — unsuccessfully.
“Andrew and I were nobodies,” Anderson wrote on Twitter recently. “No Ivy League. No previous exit, or failures of note. Great VC firms dragged us along.”
The duo were hoping to raise $5 million for the startup, Catch.
“We were turned down or ghosted by at least 50 VC firms,” including local investors such as Matrix Partners and General Catalyst Partners.
She and Ambrosino had flown to San Francisco for an interview with Y Combinator, a startup “finishing school” that is tougher to get into than Harvard or Stanford. (It was founded in Cambridge and helped launch companies like Dropbox and Airbnb, but now operates in the Bay Area.)
“I filled out the application late at night after crying all evening,” Anderson wrote on Twitter, “because I thought we were going to have to shut the company down. I stopped. Sucked it up. And wrote the best damn application I’ve ever written.”
The startup’s focus: helping freelancers and gig-economy workers who don’t have benefits deal with the headaches of taxes, health insurance, and saving for retirement.
Anderson and Ambrosino spent the first day of 2019 prepping for a 10-minute admissions interview with Y Combinator on Jan. 2. “We’d already done the contingency planning of shutting down the company,” Anderson told me. They didn’t want to leave Catch’s 10 employees in the lurch, without a final paycheck and some severance. If an applicant doesn’t get into Y Combinator, they receive an e-mail that night; if they are accepted, they get a phone call. Anderson and Ambrosino were at a wine bar in San Francisco. The phone rang. They were in, and the program started the following day.
Every company accepted into Y Combinator gets an investment of $150,000, in exchange for a 7 percent stake in the firm. But getting in is also a seal of approval; it helped persuade a group of individual investors to write Catch checks for an additional $850,000, Anderson says.
She and Ambrosino rented a house in Mountain View for the duration of the 12-week program and attended a weekly dinner with the other founders, usually with a seasoned Silicon Valley veteran as the speaker. (Past dinner speakers have included Twitter CEO Jack Dorsey, Facebook CEO Mark Zuckerberg, and presidential candidate Michael Bloomberg.)
Unlike some of the other startups in the program, which were still building products, Catch already had 5,000 customers and was more focused on enhancing its product and figuring out the right marketing formula.
While Anderson and Ambrosino were in California, they heard from a Boston venture capital firm with an offer of $3 million. But the cofounders felt the company needed $5 million to keep improving the product, marketing it, and hiring employees. They made a bet that other investors would see things their way — that it wouldn’t make sense to run the company on a shoestring and be forced to raise more money in a year or so. They decided to turn down the Boston firm.
By March 2019, Catch had sealed a deal for $5 million from a group of California and New York venture capital firms. Just after that, TechCrunch, the blog of record for the startup scene, wrote a piece calling Catch “one of the hottest Y Combinator startups.” At a dinner at the Four Seasons in San Francisco, Anderson was introduced to a VC who called Catch “the belle of the ball.”
Not many Boston startups that head west for the Y Combinator program wind up returning. But often, those startups enter the program with just two or three people, and Catch already had a team of 10 working here. Anderson and Ambrosino flew back in early April, “feeling like we were rock stars,” Anderson says.
“But our team doesn’t give a sh--. And nobody else gives a sh--. There isn’t the rock-star status for founders in Boston that there is in San Francisco. It was very humbling. But it’s also one of the reasons I love being here. It reminds you that you’re not as good as you think you are. You’re here to do the work.”
The latter half of 2019 involved “a lot of really unsexy, laborious work” on agreements with insurance companies and the Centers for Medicare and Medicaid Services so that Catch could offer freelancers and sole proprietors health insurance in 38 states.
“That finished the triad of things we wanted to build: investment capabilities, savings, and insurance,” she says. “If you’re not doing those three things, you don’t have a financial safety net.”
Jake Gibson, an early investor in Catch, says the biggest challenge is that “customer acquisition is still going to be very hard,” meaning attracting new customers at a reasonable marketing cost. Despite that, “the upside is huge, and the opportunity is huge for Catch.” Gibson was a cofounder of the financial planning site NerdWallet.
Comparing San Francisco with cities like Boston and New York, Gibson says, “There’s just a mentality here, for better and for worse, where people focus more on the upside than the downside. You’re focused on the vision, and what the company could be, and less focused on, ‘How much money could I lose in this deal?’ ”
Anderson is planning to spend February in Austin, Texas, one of the top cities for freelancers — doing on-the-ground marketing with real estate agents, hair stylists, wedding photographers, and strippers. (“They take taxes super-seriously,” she explains. “They are disproportionately likely to be audited by the IRS.”) One key goal is finding out what kinds of incentives work best to get a Catch customer to tell friends and acquaintances about the service.
The company has grown to 18 employees in an office overlooking Boston Common and the State House. Sitting at a boardroom table, Anderson reflects back on a year split between Silicon Valley and Boston, between almost shutting down the company and having $5 million in the bank.
“Everyone in Boston, including VCs, starts with the premise of ‘Here’s why this won’t work. I’ve got 14 reservations about it,’ ” she says. “I’m hoping that Boston can suspend a little of its disbelief more, and let some portion of its founders succeed.”