Episode 12
July 28, 2020

Matchmaking and Business Creating

With Talia Goldstein, CEO and Founder of Three Day Rule

About this episode

Three Day Rule is a matchmaking service that helps singles take charge of their dating, customizing their matches to fit members’ lifestyles and introducing them to only the best dates. In this episode, Talia shares with us her entrepreneurial journey from playing varsity sports and running for class president to quitting her job in TV at E! Entertainment to start her own business. She talks with us about her experience in raising capital for her company while pregnant and how she inherited the CEO seat from her former co-founder. She also describes her obsession with matchmaking and gives us dating advice for finding true love as well as business lessons she’s learned along the way.

This episode is sponsored by

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In This Episode You’ll Hear About:

  • How growing up in California, playing varsity sports and running for offices like class president showed her that her personality was full of drive and fight
  • Why college in New Orleans with a study abroad in Spain became an eye-opening and important experience 
  • How her internship at Ford Models and Susan Blonde Inc music company in NYC during college summers was both fun and informative
  • How her initial dream of becoming a publicist in LA was abandoned but eventually led to a job at E! True Hollywood Story
  • How her time at E! revealed her hidden talents of matchmaking and led to her toward being known as the “Resident Dating Expert”
  • Where she got the name for her company and how she first started as a blog
  • How her time in the incubator program at the Founders Institute led to a lesson on trusting yourself as the expert of your own idea 
  • Why Three Day Rule’s time on Shark Tank was worth the risks and difficulties they endured to get on the show
  • Why Talia believes having a strong and healthy company culture is critical to success and how she and her team intentionally cultivate this
  • How fundraising as a woman with a growing family became a challenge for Talia during both of her two pregnancies and how, with grit and determination, she overcame that
  • Why her unplanned role of CEO helped her gain clarity 
  • Her advice for other entrepreneurs and how she balances the stress of life, work, and family

To Find Out More:



“I'm such a strong believer that the best ideas don't have to come from the business team. You know, a lot of times they come from our matchmakers that are on the ground.”

“I went out two days after giving birth and closed nine investors.”

“I always say a determined woman is unstoppable. People just have to recognize that and move forward.”

“I should have followed what I was actually passionate about, but instead I was listening to the trends, and what I recognized, in the end, was that I was the expert.”

“I always look at everything like a pie where my husband gets a slice, and my work gets a slice, and my kids get a slice. And if I can get a little sliver for me, then my day is so much better.”

“I never thought in a million years that I would be a CEO.”

“I would say find something that you care very deeply about. And once you have that, do whatever it takes to make sure that it's successful. You're gonna hit a lot of bumpy roads, but be a fighter and you will get through it.”

“So I would say half my job is bridging the gap between people who actually like each other and don't know, and the other half is really helping people become their best dating selves.”

Read the transcript

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