Overcoming Obstacles and Lessons Learned on My Way to Building a Dating Empire

Growing up in the late ’70s and ’80s, the word entrepreneur was not in my vocabulary (or most people’s!). And don’t faint, but there were no books about how to write a business plan or forms online on how to build a business or strategize — Google hadn’t been born yet.

But I had an idea. I thought it was a super fantastic idea and the world (or at least Chicago where I was living) would come running for my services. My idea was born in my mid-20s when my fiancé called off our wedding 5 weeks before the big day. After the initial tears, and friends trying to set me up on dates in the following months, I had an aha moment: There had to be a better way to date. Remember: This is 1991, Match hadn’t been invented yet and online dating didn’t exist.

Andrea McGinty
Andrea McGinty

My idea was It’s Just Lunch, a matchmaking service that would work much like an executive recruiter — except you shared what you were looking for personally versus professionally. Hmmm, if I would use this type of service, I thought, so would every single in Chicagoland.

I sat down and in two hours wrote my version of a business plan with five revenue scenarios, plunked my butt down at the Chicago Public Library to look through phone books—yes, seriously, huge phone books (I couldn’t afford Lexis/Nexis to do my search) to make sure the name of my business hadn’t already been taken or trademarked. The older me, today, laughs. Like who would have picked the name It’s Just Lunch, except maybe a restaurant concept, right?

What did I learn?

  1. Share your idea with a few smart people you trust and get feedback. You’ll need thick skin.

I first shared my business plan with two people: my closest brother, a financial guy, and my best friend, who was in her third year of law school and whom I wanted to be my partner. Here was the feedback: My brother, focusing on my five revenue scenarios, simply said, “You are crazy. You won’t hit any of these numbers and no one will join a service like this.” OK, I thought as I listened, he’s married so, of course, he does not get it. My best friend took one look, shook her head and told me all the legal implications and trouble I could have. Stalking. Dishonest people. Safety. She saw lawsuits left and right. And while I did listen to them, nothing they said deterred me. This was a service I personally would embrace. So would others. I remained staunch in my beliefs.

  1. PR and the power of positive thoughts/action/words.

Four weeks into my endeavor, with slightly more than 100 clients whom I had persuaded to join, I was standing in line at the grocery store. I was broke and worrying about how I was going to pay rent next week. There was a tap on my shoulder and a woman (Cheryl, I will never forget you) I had met at a party the previous Saturday said she’d heard I had started a dating service. Oh, yes, I glowed, I just had my first couple fall in love, Roberta and Jack, I told her, and I think they’ll get married. (They did, six months later!) I chatted a few minutes about how much fun I was having but more importantly about my clients and how much fun they were having going on lunch dates. I never mentioned my financial woes or fears. Who wants to hear that stuff? So, imagine two days later, when I get a call from her. She told me she’s a producer from CNN and they wanted to do a three-minute spot with me the next day and follow a couple out on a date. OMG. CNN! This was a turning point. After the CNN story, the Wall Street Journal did a fun quirky piece on IJL and me, followed by People magazine. The PR ball was rolling.


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  1. Hire people way smarter than you.

There is no doubt in my mind here. I needed a website and I asked a young programmer, Rick, to help. I told him what I wanted/thought I needed. I asked for ABC and Rick suggested XYZ. Rick always thought five steps ahead of me and I relied heavily on his expertise to drive revenue to my site. The company was growing fast. From Chicago we leapt into NYC, Dallas, DC, Atlanta and LA. A smart CFO was willing to take a leap of faith (and a smaller salary in exchange for a bit of equity) and he took me from perpetually on the brink of bankruptcy due to rapid expansion to solvency. My mistake? I was undercapitalized. He fixed that. Not my wheelhouse, right? My PR person was 22, fresh out of college and knew no fear. She pitched me to everyone and their brother — and the results were fantastic: the New York Times, Forbes, the “Today” show and more. All three of these people are still in my life 30 years later and — not surprisingly — all three have gone on to great success in their respective fields.

  1. People genuinely want to help you.

Fast-forward a few years. My best friend is now working for one of the largest law firms in the country and offers me a meeting with the managing partner of her law firm to discuss franchising. Complimentary. Free. I spent 90 minutes with this savvy man who talked me though the pros and cons of franchising. Yes, my company was spinning a bit out of control with growth—not money issues, just pure growth. My mistake? Trying to handle it all and burning the candles at both ends. He offered a couple of ideas of how to grow in a more sustainable manner. He genuinely wanted to help a 32-year-old. I believe that. Of course, it helped that his firm drafted all our franchise documents and became our legal counsel later on. And, it was the right move — I kept some units company owned and franchised others.


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  1. Exit strategy — part gut, part looking into the future.

I loved the startup phases of It’s Just Lunch. But got bored in board meetings, which became mandatory at some point due to having outside investors, a management team, etc. I liked the client side, not meetings. And, I also saw the writing on the wall — traditional matchmaking was great, but by the mid-2000s, Internet dating was gathering momentum and, luckily, the stigma of using dating services was being eradicated. Internet dating, not matchmaking, would be the superpower of the future. Within a two-week period, I was offered the opportunity to sell by two buyers — one private equity, the other Match, the big player online. I sold to private equity.

  1. Do what you love (again!).

After a break, many vacations, a young daughter, a few investments in up-and-coming businesses, and becoming a horrible golfer and a decent pickleball player, I found myself back in the thralls of online dating. My brother (yep, the same one, just now divorced) showed me his online dating profile and I saw exactly where he needed help. Singles now in their 40s to 60s had no idea how to date online, how to write their dating profile, how to navigate online dating. They’d all married after college or grad school and were lost in cyber dating. Hence, 33000Dates.com was born. I help singles as a dating coach efficiently navigate all aspects of online dating from writing their dating profiles, choosing the right site and selecting photos to weekly coaching on how to effectively message and get the right first dates and more. I’m their objective weekly accountability partner and their cheerleader. And I’m having a blast!

  1. Give it back.

I love what I do. I also work with “kids” in their teens and 20s on startups. They are so fresh, fearless and full of ideas. Now, I’ve become the older person who people go to for advice and I’m so fortunate. And constantly learning.


Verizon Small Business Digital Ready: A free resource for learning basic business skills, the latest digital technology and more.

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