Startup stories are rarely simple. But Talia Goldstein, founder of matchmaking service Three Day Rule, had to overcome a particularly large hurdle: She actually closed her business, only to restart it months later.
“Everyone kept telling us to shut the company down, because the dating industry was so saturated,” she said. “[W]hen we had all these advisors and mentors telling us that, we believed them, and we shut Three Day Rule down.”
Goldstein’s attempted second venture — a more platonically focused social interaction business called “Let’s Do” — was also popular, but fiscally unsustainable. She decided to go back to her true passion by reviving Three Day Rule within six months of closing it.
And it’s a good thing she did — she ultimately built the venture into a $1 million business that employs 29 people and caters to hundreds of singles, 60 percent of whom are women. Three Day Rule has offices in New York, Los Angeles, San Francisco, Boston, Washington D.C. and Chicago, and has been featured in Newsweek, Cosmopolitan, PBS and other publications. It has even garnered Series A funding from Match.com and become its exclusive matchmaking provider. How’s that for market saturation?
Goldstein’s professional career didn’t always include entrepreneurial aspirations though, or even in love connections. Rather, the Irvine, Calif. native’s post-Tulane University life began in advertising. Then she entered the music world.
But while Goldstein became established there, spending eight years on TV programs such as VH1’s “Behind the Music” and the E! Network’s “True Hollywood Story,” she discovered that her true passion lay in connecting with people — and connecting them to one another.
She began playing unofficial matchmaker for work colleagues and friends. Then she started hosting singles events in the Los Angeles area. At first, only 28 people showed up. But as word spread, attendance quickly jumped into the hundreds.
At one event in 2010, Goldstein looked around and felt inspired to take a chance on entrepreneurship. “I saw hundreds of successful, fun, attractive singles. And I … decided to quit my job, so I could match them all.”
She began with a partner, a lawyer who was adept at handling the business side of the venture. The team’s involvement in a tech incubator also helped develop the operation, while an appearance on ABC’s “Shark Tank” boosted brand awareness. But it wasn’t all smooth sailing. In addition to the discouraging advice that led her to temporarily shutter Three Day Rule, Goldstein also faced the tech world’s sexism.
“As soon as we decided to raise money, I found out I was pregnant. And it’s not exactly a winning combination when you’re fundraising in the tech industry,” she says, noting that she’d read an article by one advisor vowing never to invest in a pregnant CEO. “Many [other advisors] said … they think it’s a huge red flag. So I decided to hide my pregnancy. We went out, and I wore huge shirts.”
Goldstein’s success since then — despite the departure of her business partner not long after the birth of her son — has assured her, and proven to others, that she’s on the right path. Now, she’s focused on “rapidly scaling a business that is high-touch, while maintaining quality,” she told us in her Power List application.
She advises other female entrepreneurs to start businesses they’re passionate about, to be determined and to be fiscally smart. Most of all, though, she recommends they listen to their intuition — the way you would when falling in love.
“What I learned is that … opinions are really just data points,” she says. “You can listen to what everyone has to say. But ultimately, you’re the one that figured that something was missing in the market, so, you’re the expert.”
Why do you deserve to be on our Power List?
“I am proof that determination, passion and grit can get you far. When I started my company, many of my advisors told me that the dating industry was too saturated. I believed so much in what I was doing that I decided to stick with matchmaking. Four years later, Match.com took notice and invested in us.”