Matchmaker Talia Goldstein on Business and Love


MATCHMAKER, MATCHMAKER make me a match… as long as people have been trying to fall in love and find “the one,” there have been matchmakers around to help people accomplish that just. While a friend or relative usually does most matchmaking, professional matchmaker Talia Goldstein and her company Three Day Rule are here to lend a hand to those swamped single people that not even well-meaning loved ones can help. After successfully matching a slew of friends, Goldstein decided to transform her hobby into a business. So all you single ladies — listen up! Goldstein spoke to Lady Clever about her career in love and how its unpredictability makes it different from other businesses. She also gave us tips on how to behave on a date and how you know if he is or isn’t the one.

So how did you become a matchmaker?

I’ve been matchmaking my entire life. At my own wedding, I had about 10 couples that I had matched. I’m obsessed. It’s so fun!

What inspired you to start Three Day Rule?

I was working as a producer at E! Entertainment on E! True Hollywood Story. In between interviewing celebrities, I would spend my days giving relationship advice from my cubicle. I noticed that so many of my amazing co-workers were single, mainly because they were working 14-hour days. I started matchmaking for fun in my department and managed to successfully match a bunch of couples. From there, I started hosting singles events around town. The first event had about 20 people and within months, the events were packed between 300-600 singles. There seemed to be something missing in the market because so many people who were great catches in LA were single, so I quit my TV job and started a matchmaking company.

Is Three Day Rule your first entrepreneurial endeavor?

Three Day Rule is my first entrepreneurial endeavor. However, while working on TDR, my former business partner and I started another company, which ultimately failed. I learned many lessons along the way.

What were the lessons you learned from your failed company?

An angel investor called me and said “there is a company out there hosting dinner parties for strangers. They just raised $5 million. I think you can do it better, but if you are going to take this on, you have to move fast because they are already ahead.” My business partner and I decided to jump in and start a company called “LetsDo,” which brought people together over meals. We put a lot of our own money into the company and worked tirelessly to build a beautiful website. We launched the website and every meal was selling out. On the outside, we appeared to be very successful but internally, we quickly realized that it would be difficult to build a profitable, sustainable business because the margins were so small.  We had to make the tough decision to close the business after just 6 months.

Some lessons that I learned were:

  • Don’t start a business as a reactionary measure. Take the time beforehand to map everything out and have a concrete business plan.
  • Make sure you have enough money saved up because building a business is at least 2x more expensive than you think it will be.
  • It’s cheaper to hire a developer full-time than to outsource a big project.

I learned so many valuable lessons during that time.  It has made me a smarter, stronger entrepreneur.

What has been your biggest challenge starting and running Three Date Rule?

Our current challenge is meeting demand. We have so many people who are interested in working with us, but we can only take on a limited number of clients at any time.

Our Regional Manager is traveling across the country in search of the best matchmakers to join our team so that we can take on more clients.

What are the biggest challenges you face when your business is based on something unpredictable like love?

We can only get you so far. We can give our clients the confidence to be amazing daters, and we can match them with incredible people. However, we can’t be on the dates with them. At end of the day, it’s about the chemistry between two people, and that can be unpredictable.

When we set a client up on the date, we are on pins and needles until we hear back from them the next day. We can’t wait to get the scoop!

Is it difficult to balance your creative duties with the business side of your company? Does one side tend to overtake the other?

I definitely favor some parts of my job over others. I love working with the matchmakers, doing business development, marketing & overall business strategy.

The parts of my job that I do because I have to are legal, accounting, and HR. Fortunately, I brought on a fantastic COO who is managing some of those business duties now.

What has been your company’s biggest success to date?

Aside from the many success stories, our biggest success has been partnering with As part of a strategic partnership, Three Day Rule is now Match’s exclusive personalized matchmaking company. We operate as a separate company, but can leverage their plethora of resources to help our company grow quickly.

What are your goals for your Three Date Rule?

Our goal is to hire enough matchmakers in order to meet demand, while maintaining impeccable client service, and successfully matching thousands of couples along the way.

What is the best piece of advice you received as a woman starting her own business?

Opinions are data points. Listen to what others have to say, take in their feedback, but ultimately do what you want. You know more about your business than anyone else so trust your gut.

What is one piece of advice you wish you had been given as a woman starting her own business?

I wish someone would have told me to be fearless and to not care what others think. When I got pregnant, I asked my advisors if I could fundraise while I was pregnant and most of them said it was a bad idea. I listened to them and hid my pregnancy.

In retrospect, I wish I had been more confident. I wasted a lot of time feeling embarrassed for being pregnant while trying to raise money.

I wish I had owned it. I would have been a better role model for women in the industry and I am sure we would have raised the same amount of money.

What is one piece of advice you would give to women starting their own business?

I have so much advice! Here are a few thoughts:

–       Get mentors, especially female mentors to help guide you. Don’t be afraid to ask them questions.

–       Have a support system outside of work. Being an entrepreneur is a rollercoaster ride so it’s important to have supportive and encouraging friends.

–       Only hire people who you desperately want to work with. You have to like them so much you would tattoo their name on your arm. If you hire people you feel lukewarm about, you will end up firing them.

–       On that note, hire slow and fire fast. If someone isn’t working out, get rid of them ASAP.

–       Hire people with positive energy. One person with negative energy can bring the entire team down.

–       Have fun! The exhaustion of running a company is only worth it if you laugh daily. If you are no longer having fun, do something else. Life is too short.

Have there been any gender-specific challenges you’ve faced being a woman with her own business?

As a female CEO running a personalized matchmaking and dating service, I sometimes run into other entrepreneurs or business professionals who have preconceived notions about the nature of my business.  Some fall into the trap of thinking my business is “cute” or more of a “hobby,” and may not initially take Three Day Rule seriously as a business.  I love proving these people wrong and changing their mindset once they start digging into the fundamentals of the business and realize the market opportunity, immense amount of value we provide our clients through our high-touch, personalized service, and the high margins we are able to maintain.

Have you found it difficult to balance your personal and professional life?

Yes, it’s difficult. When you love your job, you want to work all the time, but that’s unhealthy and unfair to your family and friends. To be honest, this is a work-in-progress for me. I’m trying to spend less time working and more quality time with my incredible husband and my adorable son.

Can we have some professional perspective on the dating fame? What is your biggest dating tip for women?

Be proactive. Approach a guy at a party or initiate online. Get a first date. Once you get the date, you can go back to being traditional. It worked for me.

What is the biggest mistake people make on dates, in your opinion?

They judge too quickly, especially women. Real life is not like a romantic comedy. It’s not often that you meet the love of your life and sparks fly immediately. For most successful couples, it takes a couple of dates before they feel a strong connection. I think there are a lot of missed opportunities in dating because people judge too quickly.

How many dates do you advise a woman give the guy before realizing he’s not the one?

I think at least 2. If a guy is interesting, nice and you are remotely attracted to him, give him at least one more shot.

Can you give us some insight into your process on how you match people?

If you are my client, you come to me and tell me what you are looking for in a guy. We spend about an hour together. I then go back to my database and find about 100 guys that fit your criteria. I narrow them down and choose the top 20-30. Then I go and interview them, just like I interviewed you. I find the ones that are truly compatible with you and then I set you up. You go out on a date, and give me feedback, and we go from there. Some clients marry the first guy they are matched with, and for others it takes longer.

80% of our clients refer another client to us. Regardless of the outcome, you learn so much about yourself and have a lot of fun in the process that it’s definitely worth the investment.

Who needs a Yenta? Goldstein will help you get a ring on it.

To get more tips and maybe even sign up for Goldstein’s services yourself, follow Three Day Rule on Facebook, Instagram, and Twitter.

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