“Being A Founder & Mom Are Not Mutually Exclusive” Words of Wisdom with Talia Goldstein, CEO of Three Day Rule

Yitzi Weiner
Mar 20, 2018 · 7 min read
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I had the pleasure of interviewing Talia Goldstein, the CEO and founder of Three Day Rule (www.threedayrule.com). Three Day Rule is the nation’s leading, personalized matchmaking company and is backed by Match.com. With a team of 50 across the country, TDR’s matchmakers work with busy, accomplished professionals to help them find love. Over the past year, TDR has grown from seven to nine cities, doubled its revenue, and launched into the LGBTQ+ market. In 2016, TDR was one of only two US-based dating companies to raise venture capital funds.

I began my career as a TV producer at E! True Hollywood Story in Los Angeles. I quickly became the office’s dating expert, successfully setting up many of my colleagues. Recognizing my hidden talent for connecting people, I began hosting popular singles events around town and started offering personalized matchmaking. The business started to take off so I took a leap of faith and quit my job to start Three Day Rule. In 2014, Three Day Rule secured an investment from Match/IAC and since then, has formed strategic partnerships with other large dating sites including OkCupid, JDate, and Christian Mingle.

When I was working as a producer at E!, I made it my mission to match the grumpiest guy in the office. After I successfully matched him and saw how he changed for the better after he was no longer single, I had an epiphany. I thought, “If I can match this guy, I can match anyone,” and shortly afterwards, Three Day Rule was born.

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At Three Day Rule, we help busy singles outsource their dating lives to us so they can spend more time on quality dates. We first meet with you in person to understand your preferences, dating history, and what you are looking for a match. Then we go out and personally vet potential matches for you and only introduce the best ones to you. After each date, we get feedback from both parties so there are no more guessing games about how the date went or whether or not your match was interested in you.

The first time that I had to fundraise, I ended up hiding my pregnancy from potential investors because I was afraid of the stigma associated with being a pregnant CEO. I was unsettled by that experience so when I found myself pregnant again during my next round of funding, I decided to take a different approach and share my story publicly. I wrote an op-ed in Fortune that recounted my experiences fundraising while pregnant and received an outpouring of emails from other women who went through a similar struggle. For the second raise, I proudly showed my baby bump during funding meetings and found that investors were interested, but wanted to wait until “after I had my baby.” I ultimately raised my round after giving birth to my daughter.

I truly believe that women should be able to be pregnant and raise money, especially when their company is thriving. I think we have a long way to go to get rid of the unconscious bias against female founders, and I am making it my mission to support and empower other female entrepreneurs because I never want a young woman to have to decide between starting a family or becoming an entrepreneur. I hope that by sharing my story, other women will feel comfortable doing what I did. We can absolutely do both.

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1) Trust your instincts.

When I first started Three Day Rule, lots of people told me to get out of the dating space. They said it was too saturated and that we wouldn’t succeed. Because these people were successful investors, accomplished business people, and trusted advisors, I thought they were the experts. So, despite my gut feeling that something was missing in the market, I listened to them. For a short period of time, my former business partner and I actually shut down our dating company and started another company which was more “on trend” at the time. 6 months in and our life savings later, we recognized that we weren’t passionate about the new company and decided to shut it down even though it was doing well. Instead, we re-launched our dating company, Three Day Rule, and went full steam ahead, only to prove everyone wrong.

2) Being a founder & mom are not mutually exclusive.

When I got pregnant with my first child, I was so thrilled to start a family, but felt ashamed at my timing because I happened to get pregnant right when I just started fundraising for Three Day Rule. Just around this time, I read a blog post that went viral which featured an angel investor who was openly hesitant about funding a pregnant CEO. After reading that post, I decided to hide my pregnancy during fundraising. I was able to successfully close a round but looking back, I wish that I had role models and other business leaders telling me that it was perfectly okay to be a mother and an entrepreneur. Now I know that you can absolutely be a founder and a good mother at the same time, I want to help other women feel confident they can do it too.

3) Find advisors who will give you tough love.

When I first started TDR, I would look for advisors who would get behind my idea, but also give me constructive criticism that I could handle. This felt productive and safe. One time, my former business partner and I met an entrepreneur at a conference who seemed intelligent and kind, so we asked if we could pitch him. He agreed but when we did our pitch, he ripped us into shreds about our approach, our margins, and so much more. We left teary-eyed, but after some thought, realized that he was right. And, we changed the way we did business after that meeting. Now, I tell everyone to find advisors whom you trust, but also who you know won’t sugar coat and won’t be afraid to give you some tough love. You don’t have to listen to them (they may be wrong) but I think it’s important to pitch to people who will push back on your ideas and challenge you to really think through the tough questions. You’ll thank them later for it.

4) The roller coaster never stops.

Start-up life is a never-ending roller coaster. I thought that the beginning would be tough but that after funding, running a company would be smooth sailing. Boy, was I wrong. After funding, you have to push even harder than before because there is always the next milestone you want to achieve and the next goal you have to reach. The work changes as you get bigger and scale, but it’s still a crazy, beautiful, emotional ride that is definitely worth it in the end.

5) Celebrate the small successes.

There are big milestones like funding that, of course, you should celebrate, but it’s very important for morale that you celebrate even the small wins. For us, that means getting a client on a third date or into an exclusive relationship. It’s a big deal to the employee who made this happen, so it’s important to celebrate that with the entire team. Each Monday, during our all-hands call with 50 employees across the country, we start it off by reviewing the successes of the previous week to remind all of us why we decided to work in matchmaking and to remind everyone of the difference we are making in people’s lives.

I’d love to have breakfast with Johnny Galecki because he seems like such a great catch and it would be fun to match him. I recently read that he’s back on the market. Johnny — if you’re reading this, let’s get in touch! I’d love to match you.

Authority Magazine

Leadership Lessons from Authorities in Business, Film…

Yitzi Weiner

Written by

A “Positive” Influencer, Founder & Editor of Authority Magazine, CEO of Thought Leader Incubator

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

Yitzi Weiner

Written by

A “Positive” Influencer, Founder & Editor of Authority Magazine, CEO of Thought Leader Incubator

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

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