"I'm kind of a risk averse person — if I have something safe, I felt like I might just sort of keep doing it," she says.
"[But] we just kept getting more and more excited about the possibilities of it, and I just started spending more time on this than anything else and kind of obsessing about it," Mayer says. "It felt like if I didn't give it my all, it wasn't ever going to happen. So I took the leap."
Mayer had a solid safety net of savings that had taken some time to build up, and she had enough work experience that, if Havenly failed, she was confident she'd be able to find another gig. Still, going from the comfort of having a stable income to the unpredictable world of entrepreneurship was a monumental moment.
"I felt confident that I could find a job if I needed to find a job," Mayer explains. "I had plenty of experience under my belt and the financial resources to spend time on this without a salary, so it's funny that I think about it as so risky. Because looking back, I don't know if it was. But it was a pretty scary moment when you're like, 'Alright I'm going to start this.'"
Motayed, Mayer's sister, also left her full-time marketing job to work on Havenly. (She has since moved back to New York City to work for another start-up.)
Mayer used her own money and $150,000 from her family to start the business. Since she understood the basics of coding, she built the first, most-basic version of the site herself and enlisted a single interior designer. She says she worried that if Havenly didn't work out, people would look at her as the, "girl that failed a company."
"I think more broadly it was just fear of failure…" Mayer says. "How would I explain this to my mom, that I took a year off to start a company and it went nowhere? And looking back, I kind of laugh at that a little, because that's just silly," she explains.
"But I think we so often — all of us — put so much pressure on, not just intrinsic pressure on us, but we think way too hard about what's happening, and what other people are thinking about of our successes and failures."
The biggest obstacle she had to overcome when building her business, Mayer says, boils down to just figuring out what to do next. The feeling of having so much to do, she admits, can be overwhelming.
"It can be really frustrating because it's just like you never feel like you're getting there fast enough and you're a little on your own," Mayer says. "It's just you and your co-founder and no one else kind of gets what you're doing."
It wasn't until the first and second quarter of 2015 that Mayer really felt the business start to ramp up, and even now, admits she's still not sure they've had that major breakthrough moment yet.
"To be perfectly candid, [when people ask], 'Oh did you make it?' I'm always still like, 'Yeah, we made it — no, we didn't make it.' So there's always that little bit of tension," Mayer says.