Making a Living from Matchmaking – Sarah Kathryn Walmsley

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We all have that one friend who is always trying to set people up with each other. Some are better at it than others, but Sarah Kathryn Walmsley is one of the best – she’s made a successful career out of matchmaking, and has made her off-line matchmaking service a thriving business in the age of online dating and dating apps.

Sarah Kathryn has been matchmaking for 20 years now with her Atlanta-based company, 8 at 8 Dinner Club–which sets up 4 single men and 4 single women to go to dinner together at 8:00. She also runs 1 on 1 Matchmaking, a more “high end” matchmaking service where single professionals ready to find the right one are set up on 10 handpicked dates based on what they’re looking for.

This Valentine’s Day, Sarah Kathryn was kind enough to tell us her story, share some of her wisdom, and explain the difference between finding a career to love and a person to love:

 

MG: How did you think about doing something like this, and how did you get into it?

SKW: In high school I was a busybody; I was always setting people up from my hometown with people at my high school, because I went to school across the city.

My dad saw that, and [after college, when I didn’t like my job] he actually had a friend who had started 8 at 8 Dinner Club, but the gentleman had already given up on it. He was a trademark attorney, and he was just exhausted from how hard it is to run. It’s a lot of people and a lot of tedious emotions, and a lot of sales trying to get people to join. So he burned out of it pretty quickly. But he had a client database and a trademark, and so my dad suggested I just buy it. I did a straight asset purchase, for $2000, then I paid him 10% of whatever I earned for two years.

And I worked so hard, as a 22 year old entrepreneur. I worked out of my parents’ basement, and I got a lot of interns who were college students and willing to work for free. And I went on to make 8 at 8 a national brand – we took it to Dallas, Chicago, New York and DC. We were on Oprah, and in the New York Times, and the Wall St Journal, which was exhilarating.  And the smart thing was, I was an entrepreneur when I was still young enough to not really need a lot of money to live.

 

MG: You’ve been doing this since before dating apps and online dating were popular. How has the landscape changed and have you had to do anything different to fit in?

SKW: One thing that a lot of people are saying to us in the last year or two is “I’m here because I’ve been ghosted 3 times this year”– after dating for like 10 weeks! Just getting ghosted out of the blue.

[By hiring us,] it’s a little like hiring a friend. We will deliver to you some rough advice. We’ll tell you things like “3 of the last 4 ladies have said…”   We literally told a guy the other day he had halitosis. If you are getting rejected and don’t know why, we’ll get you feedback to help you figure out why and hone your skills. And we’re constantly referring clients to stylists, or helping them find new clothes.

At this point in the world, dating apps are definitely our competition—our online competition—but they also drive unhappy customers to us all day long. Because people are frustrated [by online dating], and they don’t know enough about the match, and the caliber [of potential matches] is just the general public. And many people aren’t actually going on real dates with the apps, or they get stood up. If you’re a busy professional, it’s not worth your time.

With us, you’re guaranteed to not waste your time. They’re definitely going to show up. The reservations are made for you, at hip, trendy restaurants. You get the best tables. And then we get your feedback and give you feedback.

. . . .

Whereas a dating service will only set you up with people in their pool – “you paid, you paid, maybe you should be together.” – we’ll set you up with anybody. We pull from our [several hundred] 8 at 8 clients. We also pull from our 1 on 1 people. And we will pull from any client that is a previous member, or someone’s brother or a sister or a cousin. We care about the match more than just if that person has paid.

It’s difficult to catch people in the moment of being single and miserable Click To Tweet
MG: The 8 at 8 model – with a 4 + 4 plan — sounds like you would need similar numbers of men and women in your pool. Is that a logistical problem? Is it easier to attract one side vs. the other?

SKW: Huge problem. Huuuge problem.  If I was selling pizza, I could sell it to any individual as long as they aren’t lactose intolerant. But because I’m trying to market to singles – I guess they call it a parade audience—sometimes you’re single and sometimes you aren’t. It’s difficult to catch people in the moment of being single and miserable (laughs).

A really tough time for us was when we got on the Oprah Winfrey show. It was a big, big dream come true for an entrepreneur. But all it got us was female applications from all around the country!

[When it gets too imbalanced like that,] we end up turning away a lot of money [from interested women]. We’d have people getting mad and yelling at us, and I was like “I’d love to take your money, but we don’t have enough guys!”

The Wall St Journal had a column on small business dilemmas, and so I wrote to the lady, and less than two weeks later they wrote a piece about us and what to do when you have a business with an imbalance. But that’s but an ongoing struggle — women have always liked the concept a little bit better.

Is it easier to find a person to fall in love with or a job to find in love with? Click To Tweet
MG: Is it easier to find a person to fall in love with or a job to find in love with?

SKW: Oh my gosh, that is a great question. I think it’s easier to find a person to fall in love with. Finding a job is so much more of a black hole.

When I first got out of college, I could not find a job.  I’m a decent normal person  (laughs). I had a degree; I’d even had an internship, a good one. But my college was not plugged into that track of people that are lucky enough to get that first job easily.   Getting that first job was harder to get than almost anything I’ve ever done. It was a debilitating and depressing time of my life. I wish I had temped, or done a part time job. I just felt very lost.

In dating, you’re at least talking to the buyer. With a job, it just felt like you’re stuffing your resume in a black hole.

I think it’s easier to find a person to fall in love with. Finding a job is a black hole. Click To Tweet

 

What are most people doing wrong in dating?

Everybody wants to date out of their league. Everybody wants one or two notches better than they are. It’s like buying a house, they want the biggest house for the money, so they want to go for the hottest, or the most successful, or the most fun person they can find.    Really at the end, all of us have to settle a little bit, on something. You don’t really know how you’re going to settle. Because you end up falling in love with the person anyway.

Being a matchmaker for so long, nobody was setting me up. And when I was searching, I tried to narrow it down to men within a mile of my house, who were University of Georgia alumni like me. And that was stupid. . . In the end, the love of my life is a Florida grad who lived 30 miles away. I realized I hadn’t been taking my own advice. The New York Times ended up coming to our wedding and making a story out of it, because I had been ignoring my own advice, but ended up finding love in spite of that. We all settle for something, and those weren’t bad things to settle for.

Everybody wants to date out of their league...one or two notches better than they are Click To Tweet
MG: Now that you’re on the other side, as an employer of others, how do you identify talent, and how do you ‘replicate yourself’ when expanding a business you began?

SKW: I definitely enjoy getting people on a temp-to-hire basis – it gives you a chance to smell each other out.

I like talking to references, and spending time to just shut up and listen to whatever their references say, because you can read between the lines. But it took me 12 years before I actually found ‘my clone.’ Jennifer is uniquely passionate about the industry, well represented with the clients. We’re lucky in that we have different skills – I’m better at managing the business and making sure the bills get paid, and she is a sales monster.

No business works well without sales. None of us can be a matchmaker without more clients. And I can sell, it’s just not my favorite thing to do.

Sales is a great skill to learn, even if you think you don’t enjoy it, because everything needs it.

Sales is a great skill to learn, even if you think you don’t enjoy it, because everything needs it. Click To Tweet

 

MG: What are the top things you want to see in a candidate

SKW: I’m super busy; I don’t mind a little persistence. I’ve been known to actually hire someone because they were a bit persistent. If that person can adapt to how I need to be communicated with, then I think they might be a good representative for our clients.

If you really want that job, do what it takes to get that person’s attention–and I’m not talking balloons and cookies. I mean like a well written, concise, letter.

We should all maybe take a really hard look in the mirror at how polished we are. I love hiring young people, but what they sometimes lack is polish. It’s not their fault, they just don’t know. It’s very subtle.

. . .

Another thing about hiring — When you get out of college, sometimes you think, “I want to work at CocaCola! [or another giant, extremely visible company]” But that is a huuuuge place to try to infiltrate.

And there are so many small to medium sized businesses that simply don’t have the time or manpower to be recruiting and searching. But let’s say you want to work in, say, search engine optimization. If you approach a couple smaller companies, send them your resume, and leave them an intelligent sounding voicemail, who knows what can happen! Those people are desperate for young, squeaky clean talent.

And then the thing to always remember is, are you creating value? Our last intern, we ended up hiring her full time, because she started to sell memberships! She made herself very valuable.

 

MG: If someone else fancies themself a young matchmaker like you did, what advice would you have on making a career out of that, or other avenues they could pursue with that interest and talent?

SKW: I think if somebody has a real entrepreneurial bent, they can start their own. There’s plenty of room for more matchmakers. There are alliances of us and groups that operate like thinktanks for ways to improve; to optimize our contracts and websites and ads…

Actually getting it off the ground is the hardest part, though, so it might be best to find someone wanting to retire, or find somewhere to intern.

 

Any final advice for turning something you’re passionate about into a career?

SKW: Be willing to work your ass off, and sacrifice a lot of things and sleep and energy along the way, but if you’re that passionate about it you can do anything you set your mind to.

Be willing to work your ass off, and sacrifice a lot of things and sleep and energy along the way Click To Tweet

 

Check out other “Careers in Love”:

Careers in Love

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Matt Gwin
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