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  • Writer's pictureKarla Ray

Money Manager Ditches Hong Kong and Wall Street For Matchmaking

Expectation vs. Reality.

We see it all the time on funny memes and viral social media posts, because it’s so relatable. The expectations we build up in our minds, the high standards we set for ourselves—sometimes we need to be humbled and brought back to reality.

As a new(ish) mom, nothing is more humbling than the realities of all those highlights we see on social media; think fall family photoshoots where you just know the toddler was screaming two seconds before getting that ONE shot that you need for a holiday card, or the trip to see Santa that ends with mom sweaty off to the side from wrangling a wriggly kid in an hour-long mall line.

(See my son's first meeting with the Big Guy himself... I'm off to the side trying to calm him to no avail).

Beyond our own expectations, there are the expectations that are placed on us by others. Those societal expectations weigh even heavier in certain cultures, and going against the grain can mean more than just a side-eye from a stranger.

For Cassindy Chao, being a second-generation Asian American whose parents moved to the states from Taiwan came with a lot of unspoken expectations.

“I was born in Queens, and my parents were very much about education; go to good schools, study hard, you know, be in the sciences or whatever,” Chao said. “And it didn't gel with me. I flunked out of my calculus class. I flunked out of chemistry. Clearly, that wasn't the path.”

Despite the failing grade in calculus, Chao found herself studying numbers; double majoring in Chinese studies and economics. The combination led to huge success in the banking industry- working on Wall Street and then Hong Kong at big-name institutions like JP Morgan and Goldman Sachs.

“Everyone thought I was really good at numbers. The reality was, I'm really not very good at numbers,” Chao joked. “I'm okay, not great. I always just didn't feel like I shined there. I'd be in meetings and it's very hardcore… I’d sit there in meetings, having worked all night, but just being so bored. So bored.”

She worked in finance for ten years, but said she never loved it.

“It didn’t resonate with me,” Chao said. “I was having much more fun just thinking about who and who would be great dates, and who would match better.”

Whether intentional or not, Chao was paying homage to her roots by taking an interest in making a match; Though not exclusive to China, matchmakers have been part of Chinese culture dating back to ancient times, when engagements and marriages were more of a group effort focused on family reputations and social status. To this day, older generations still work to set up their children with a life partner. Despite this cultural acceptance, it did not make the switch from finance more palatable to Chao’s parents… at least at first.

“Every parent, whether you’re Asian or not, is worried about their kids and they want them to be financially independent, financially sound,” Chao said. “They didn’t come from Taiwan to the United States for me to be a matchmaker… I clearly wasn’t going to be a doctor, but certainly not a matchmaker.”

The expectation did not match Chao’s reality. After that decade in the banking industry, during a stint working in tech, Chao started to study again; at this time, for more of a hobby to escape the high-pressure workplace she was in… not numbers, but something similarly calculated.

“I love people. I really like to find what's special about them. And I love matching people… It’s just not what people are going to see when they first meet me,” Chao said.

Though she had a whole career in between, Chao’s first foray into matchmaking started at Wellesley College in the 1980s, where she launched the Asian Association’s Blind Date semiformal out of her dorm. Well before those finance jobs would take her around the world into some of the busiest boardrooms, she would find her peers matches by asking questions that included what their favorite cereal was.

Those early days at Wellesley came with a lot less pressure.

“It was so much fun,” Chao said. “I didn’t know until years later that it could be a career.”

Think about it- most everyone is looking for love or to be loved. It’s already a billion-dollar industry when you consider online dating services alone, nevermind the amount many spend trying to conform to what they believe will make them more desirable to a potential life partner. It makes sense that matchmakers help keep this love economy going, but it begs the question- what sets someone apart as a professional rather than simply a friend who wants to set you up?

“There’s a phrase called profitless prosperity, and that’s something to avoid,” Chao said. “Everybody has an inner-Cupid, we all want to help people match, but sometimes we do it pro-bono, for free; that’s profitless prosperity. What’s important is to make it into a business, because it does take time, and to really value your own time as well.”

Monetizing something as speculative as the potential to find a partner might’ve been trickier if Chao hadn’t come from the world of Wall Street—a profession full of men who wouldn’t think twice about what to charge for their time and expertise.

“I structured the packages, and it helped me learn to raise my rates. It’s a business. So my rule of thumb was, every three clients, it was time for me to raise my raes,” Chao said. “I also align my packages with the interests of the clients; I have a relationship bonus, or engagement bonus, so the clients feel comfortable that I’m aligned with them. I want their success.”

She’s found success through the help of a rigorous screening process, noting that the first person a client matches with is, in fact, their matchmaker.

“I think every matchmaker is different. For me, the process I do is very, very deliberate and very focused on the client… I have a very extensive intake,” Chao said. “I have to understand them, and they also have to trust me.”

That intake includes taking inventory of a person’s inner circle, and being a buffer for the sometimes very blunt feedback a friend may not feel comfortable saying to a person’s face.

“The smartest people have blind spots. So who are the people that love you? Maybe your family, your friends, and I’ll ask 3 to 5 of their trusted friends and family to kind of hear about what their blind spots are,” Chao said. “Who would you think is a really good match for them, or is there something that you're kind of afraid to tell your friend as to why they're still single?”

Though she wasn’t into the sciences when it came to studying, she certainly has a knack for spotting chemistry. After the intake and screening process, Chao’s clients get real-life, low pressure practice with some mock dates, which really just screams reality show waiting to happen.

“It’s a very safe practice date to see how this person is presenting,” Chao said. “Then I put together a program, and a dating plan, and sometimes it could be a dating buffet to try different people, to meet different people outside, and then do feedback. THEN I start doing the matches.”

Chao’s business, Ancient Wisdom/Modern Love (which is also the title of her book- available here) has three levels of service: Relationship Networking, in which anyone can join the ‘pool’ of singles looking for a match (for free), Relationship Coaching, which goes a little deeper and includes an hourly rate with a 10-hour minimum for more success in dating, and Matchmaking. Chao says not every prospective client gets to that third level.

“There are some clients who, even though they could pay, they're just they're just not suitable for matchmaking,” Chao said. “They’re very rigid, they have a checklist or sometimes they want a clone of somebody that they broke up with or who broke up with them… it’s a replica, and we can’t replicate that. We’re matchmakers, we’re not magicians.”

Preconceived notions- or expectations- not matching with reality.

“I get really involved, I’ll think about my clients all the time, so if they’re not kind of open minded, it’s really hard for me to work with them, and it will really bring me down if they’re angry or sometimes not emotionally available,” Chao said, clearly an empath. “That can happen when they might be healing from a divorce or a bad prior relationship, so they’ll be suspicious of everybody coming over the transom.”

Chao’s process is prestigious and private, and though she pulls from that Ancient Wisdom of her ancestors, her matchmaking looks much different than what you might see on the literal streets of China, where the tradition has become a source of controversy. Modern-day Chinese matchmaking involves a sorting of social status and hierarchy, with the ‘hukou’ system identifying a citizen’s permanent residence and, therefore, all but guaranteeing that the affluent stay surrounded by others of their same upbringing. For better or worse, being a native resident of Beijing or Shanghai comes with certain privileges.

Lucky for Chao and her clients, those factors are not an issue. In fact, her focus is the


“A good matchmaker, we really delight in that unexpected match,” Chao said. “When you can kind of tickle their fancy with somebody they normally wouldn't have met, and then they really hit it off, that's where the magic happens.”

Chao credits the magic she’s able to create to the training she received from a fellow Wellesley graduate, who she reached out to during a slump at her finance gig.

“It was serendipitous. I was really bored at my job, and frustrated, and I saw this article in a magazine about a wonderful matchmaker… She had said, that you train for the best. So I contacted her and I found out who she trained with,” Chao said. “It's one thing to want to do it, but it's another thing to be really good at it and to make it into a business. That's not easy. It took a lot of tweaking to find where my strengths were and to know my own niche.”

Chao’s website describes her business as the Premier Asian Matchmaker and Dating Concierge- but it’s not exclusive to Asian Americans.

“Half of my clients are actually non-Asian,” Chao said. “It’s really empowering for professional women, for smart people, for people who are free spirits.”

But even free spirits want a quick fix. Chao is careful not to overpromise a match, and warns her clients that this is a process.

“They often think I just serve up the people, they go on three dates, and they choose. I think that’s what everyone wants,” Chao said. “So what I tell them, is this is an important decision. The cost of mistakes is very, very high, that you do want to spend a little time here.”

Even in a paid service, people often think they know best. Chao says, in those cases, it’s better to show, not tell.

“People will be people. Sometimes, what I’ll do, is set them up on matches that might be what they THINK they really want, but in our heart, we know it’s problematic,” Chao said. “We let them come to that conclusion, too.”

It’s a little bit of reverse psychology, and though she’s not a licensed mental health therapist, Chao says the coaching she provides is often a gateway for her clients to unlock certain mental blocks; something she has a bit of experience in, too, after changing career paths.

“It’s very hard, navigating a new career path,” Chao said. “There’s a lot of self doubt to walk away from a career that pays quite well, even though it makes one unhappy, was very difficult. I think it’s important to have a deliberate plan in place as to how long you’re going to be doing this for, and to make sure that you make money on it.”

You might be surprised to hear that this matchmaker says the process to launch her business of connecting new couples, was quite lonely. She found community in the Matchmakers Alliance, a group of around 80 matchmakers that shares advice… and shares clientele for potential matches.

“We have to collaborate in matchmaking, because nobody has the world’s biggest database, right?” Chao said. “Sometimes people have certain requirements. For example, a client who is seeking only a Christian gentleman… I only have a certain percentage of my database, so it’s important because we want the best for our clients and we want to give them the broadest scope of people they can meet.”

That community over competition mindset is something I’ve witnessed Chao practice and not just preach. Even though we only just met for this interview, she immediately made me feel like I had a friend and confidante for life, offering to help network me for emceeing opportunities as if we go back for decades. One of her first questions to me was how SHE could help ME, which is indicative of the type of dating coach and matchmaker she is for her clients.

That’s what she hopes will continue to set her apart from the sea of apps and AI systems that promise to find you a match online with just a few swipes.

“Online dating has its place. There's nothing wrong with online dating. The good news of online dating is that there are so many people on it,” Chao said. “What's difficult with online dating, though, is that I highly doubt anybody will say it's a very positive experience. It's difficult. There's a lot of strangers out there. There's a lot of safety issues, a low level of confidentiality. And for some of my clients, they're very private. They can't afford to have their names out there, or their pictures out there.”

I think of all the friends I’ve had in newsrooms over the years, risking it all on Tinder only to be immediately recognized for their on-air work… not what people in my industry tend to lead with when they’re looking for a date, leading to potential safety or stalker issues. Chao says her goal is to prevent those problems and to protect her client’s hearts, too.

“If you’re online dating and somebody gaslights you or says something rude or just swipes, it’s very hurtful,” Chao said. “I want my clients to be as happy and positive as possible. So if they’re doing online dating and they’ve just been treated poorly, they’re not really presenting their best and it takes a lot longer.”

Her hope is to eliminate that back and forth, reduce the time it takes to find a match, and to create a positive outlook during the process.

“My goal is much more focused, and much more about preserving the client’s happiness, so that way they can navigate this relatively smoothly and with as little negativity as possible,” Chao said. “It’s not perfect, but that’s what we try to do.”

So how does she weed through a database of strangers to find a perfect match? Aside from cross-referencing with other matchmakers, Chao does email campaigns, LinkedIn campaigns, and uses specific requirements to narrow down a potential partner, all keeping confidentiality of clients in mind.

“I try to meet all the matches in person, because a good matchmaker is protective of their clients,” Chao said.

Successful matches and a strong client base are signs of success, but with those ever-present societal expectations and value placed on ‘traditional’ careers, Chao admits she’s still working to feel comfortable and proud of explaining her profession to others.

“I think it’s part of my upbringing,” Chao said. “I would say maybe two years ago I started feeling better about it, and I think it’s part of coinciding with my own age and midlife crisis or whatever it is, but also just being authentic and owning it.”

There is magic that happens when you own your authenticity. The happiest people I know are unapologetic about who they are.

It wasn’t an overnight process for Chao.

“I would say about two years ago, I started feeling like I could be much more open about what I do,” Chao said. “I changed my LinkedIn profile to allow for that, because I was kind of hiding behind a finance consultant role. I finally realized that it’s so much more comfortable and resonates so much better to be authentic. Instead of pretending to be a finance executive, when the reality is, I’m a great matchmaker and I love what I do. How fortunate is that?”

The LinkedIn update was met with mixed reviews; though most people Chao was already close to were very positive about the change, more formal finance folks went silent.

“I get it,” Chao said. “It’s sensitive now. Maybe they feel a little uncomfortable, and maybe they feel like they need to assure me they’re very happy with their marriages, and that’s fine… I love it, because people who are married make the best introductions for us because they get what’s wonderful about marriage.”

The shift toward living her most authentic life means Chao isn’t as focused on other people’s opinions.

“It’s a learning process. I think it’s hard for a professional woman, because there’s a lot of value put upon youth and friendliness, but sometimes you might not feel that friendly,” Chao said. “We just want to be ourselves.”

“I think the authenticity and vulnerability is a very interesting concept, because it also means that we’re accepting ourselves, and we’re viewing ourselves as a source of strength versus weakness. It’s very stressful to hold up a façade.”

For example- if clients aren’t truthful about their age or upbringing, those lies will start to expose themselves because you can’t lie about the music you grew up listening to or the traditions you held for the holidays.

“In Chinese, we have a phrase which means you’re pretending to be a horse, but the donkey’s foot comes out,” Chao laughed. “It’s really hard. It’s important to be authentic. It’s strengthening and empowering, and I think it just makes us happier. When we’re happier, we date better, we present better… we’re much more interesting, we’re not as rigid.”

Because she gets so invested in each of her clients, Chao chooses only to work with a dozen or fewer at a time… and because she gets so invested in each of her clients, she ends up fronting a lot of emotional weight on their behalf.

“It really is hard being a matchmaker, because you do take every client very seriously,” Chao said. “I’m in this position, I’m in this career, because I want to be helpful and effective, and it's very disappointing sometimes when that's not happening.”

She also has come to terms with the fact that this process won’t be streamlined, or even successful, for everybody. Sometimes people won’t be ready, or they may have blocked their own blessings by having certain expectations they’re unwilling to negotiate on.

“I could only marry a man who’s 5’11 or taller,” Chao said as an example. “When we start kind of letting go of that, that's when the magic happens. And sometimes you end up with exactly what we wanted to. But that's a process, right? And it doesn't come easily, because people have had that with them for years. I have I tell myself that it just takes time, and I work with them to kind of unlock it to where they can be much more open minded.”

When that works, Chao finds her calm; but when it doesn’t, she feels stressed and sad. Did I mention she’s an empath?

Aside from her own emotions, Chao fields plenty of unwelcome emotions from clients, too.

“It’s par for the course for being a matchmaker to get a lot of anger tossed at you, too,” Chao said. “Sometimes it's rightly so, but most times not. And I think that it's always important to remember that when you're single, sometimes you can be a little bit more emotionally fragile just because, you know, you may not have the emotional support that you are seeking.”

In any job, there’s a need for boundaries; but being so close to her clients, it’s easy for those lines to get blurred. How does one leave the office when your business is in your brain? Is Cassindy trying to match up every stranger she sees in public, every new acquaintance or friend?

“It’s always front of mind,” Chao said. “You’re always thinking, that person could be a good match. Do they have any nice friends? Every time I meet somebody, I’m always thinking about that. It’s because it’s something that is so important to me that I love doing, it permeates everything.”

Her love for helping others find love has paid off in dozens of relationships and engagements, including a recent success story of a client who was over the age she typically serves; At 80 years old, the man’s son hired Chao to help him find love after loss.

“I thought to myself, can I do this? And I did. The father trusted me. He was focused. We went from interviews and dates to him finding the ring in months,” Chao said. “I’ve never had somebody go that quickly.”

The urgency at 80 is truly a lesson for all of us not to wait to go after anything we want in life.

“He was like, look, I don’t have time to waste. An the woman he found was actually a few months older than him,” Chao said. “I love that they both found love late in life and they’re like high school sweethearts right now. They’re so cute together. I’m really happy about this one.”

Just like you probably wouldn’t take parenting tips from a person without kids, it makes sense that Cassindy’s most successful match to date is the one she has with her husband, Fred. Like many of her clients, she says he’s not the person she expected to marry.

“I met him at a birthday party of a mutual friend,” Chao said. “He was in sandals, in a T-shirt and shorts. I went to go flirt with this Australian-Chinese gentleman with a great accent. But meanwhile, Fred was always kind of back in mind as being just a very nice person. I was thinking, this will just be a fling. You know, not my type. But we just fell in love. He makes me a better person.”

Those darn expectations vs. realities, again.

“He’s the right person for me. The person that I need. I joke that I could walk around with a paper bag over my face and he would still think I was the hottest thing since sliced bread,” Chao laughed. “He’s a Midwesterner, and I remember thinking that since I was in finance that I had to marry some person who is sophisticated and went to an Ivy League school, all this kind of stuff… no no no. We would hate each other.”

Fred and Cassindy matched before she became a matchmaker, and like she had to break the news of a big career change to her parents, she had to break it to her hubby, too. How would your partner feel if you wanted to devote your time to pairing up suitable singles?

“He was totally supportive,” Chao said. “Fred is supportive, he’s smart, he’s funny, he’s just a great guy. He’s a great father and an amazing husband.”

The connection Cassindy has with her match is the type she tells her clients is only possible when they first love and fully accept themselves.

“I think quite often when people are seeking partners, they’re looking to complete themselves, and that’s a very dangerous way to approach relationships,” Chao said. “It’s really important to love oneself, to accept oneself, because otherwise you’re always looking for somebody else to complete you or to make up for certain shortcomings that you think are so critical.”

When was the last time you spoke love into yourself? Truly? When was the last time your inner dialogue was a positive one, and not beating yourself up over what you would’ve/could’ve/should’ve done? (S/O to my girl, Taylor for that line!).

“Just kind of revel in your own secret superpowers, what makes you, you,” Chao said. “One thing I ask clients to do is to write down five things that are really wonderful about themselves, what your friends or I would say. Why do your friends like to hang out with you? When you write those down and you visualize it, and think about it and internalize and own it, it will make you a better dater.”

This is the part of our interview where Cassindy told me about a Chinese phrase that means something along the lines of ‘taking gold pieces all over your face.’

Stay with me.

“What it really means is you’re letting your inner shine out,” Chao said. “You really should be able to shine, and be radiant because think about how much more attractive that is to anybody, whether it’s for romance or for friendship. You just have to be radiant. It’s ok to put the gold pieces on your face.”

Of course, we’re not all going to feel shiny all the time. Chao, like every other person I’ve interviewed for this blog thus far, has experienced the dullness of imposter syndrome throughout her life.

“It’s so insidious, because it takes great, strong women, and makes them feel helpless and incapacitated,” Chao said. “I have had imposter syndrome throughout my finance career. Even though I was promoted from analyst, associate and then executive director in Hong Kong, it plagued me. We are our own worst jailors.”

Even now, after many successful matches, it still creeps in from time to time.

“There are some very successful matchmakers, and they’re like the Queen Bees. They’re powerful, they’re amazing, they’re sharp. I just feel like, how could I even call myself a matchmaker next to them? I still have that sometimes… You just have to have that faith that if we work at it, things will move forward.”

And in those times you don’t feel you can move forward alone, think back to the survey Cassindy does of her prospective clients’ family and friends- what would they say about you? How do they see you?

“What I have found really helpful is the power of your friend network; a board sounds silly, but it is helpful to have a board of trusted friends. Three to five people you can share your goals with, and you help each other and support each other, and it’s a safe place. With imposter syndrome and all these things, we need a little bit of positive reinforcement,” Chao said. “And look at the trade off, right? Because being unhappy… that has a cost. So often we think, we can’t [make a change] because of the cost, but we don’t realize that the cost of being unhappy is also quite expensive.”

Seeing your life as a corporation, and your friends as a group of investors there to guide you. It’s genius, and no surprise, coming from a finance guru. Truly, it’s why so many people are seeking a match… to weather those tough decisions and lonely times of life.

In life or in love, you have to do the inner work first to see the outer world change.

“You have to be intentional… whether it's for love, or for a job, or for friendship; if you let your goals be known, it's really important. I think it's a step out of one's comfort zone,” Chao said. “A lot of times they don't like asking for help. We don't like letting people know our vulnerabilities. But I think it is important because we're human beings. We're not that different. We all want to be helpful to each other.”

It’s a strange paradox that giving to others makes us feel more full; still, Chao can tell when someone isn’t truly ready to match their actions to their words.

“I have had some clients that the timing is just off. I feel bad because I do want everybody to find their love, but sometimes they're just not ready for it,” Chao said. “I had a wonderful, wonderful woman who's so talented, so smart, but she was just stuck. She was stuck on somebody who really resembled a person that she had been with before, and this person was not good for her, because it made her very unhappy. We tried so many ways to get her to see… and I'm not a therapist. The client has to want to make a proactive change, and if they can’t do it, I also have to let go.”

Sometimes, just the practice of putting yourself out there is enough of a starting point. There’s a Chinese phrase for that, too… something along the lines of riding the mule to catch the horse.

“Go out dating, because if you're not dating, you're certainly not going to be in the running to go find your partner, the horse,” Chao laughed. “If you're not out there sending your resume out or reaching out to people, then you're certainly not going to get that great job. Ride the mule to catch the horse.”

She pulls out these phrases for her clients when she wants to soften the blow of certain feedback but still get her point across.

“How would it sound if I said to you, you overshared, you went overboard with your date? It’s much better to say something like, you don’t want to play the flute for the cow,” Chao said. “Giving feedback to matchmaking clients is very, very sensitive, and it has to be handled very delicately, because we want their emotional equanimity to be strong so that they date better.”

And it may shock you to learn that a woman who has dedicated this second act of her life to finding others their match, doesn’t believe in ‘the one’ in its truest meaning.

“I don’t necessarily think that there’s only one in the whole world,” Chao said. “I think that there are many ones for people. A lot of it's about how receptive they are at the time… I don't think there's only one the one.”

“I think that when people are attracted to each other, there’s two factors; chemistry and respect. So if you can hit that, that’s really important, there’s going to be a relationship there,” Chao said. “I think it's a very large world.”

Cassindy points out that oftentimes, we are the ones who narrow down our own playing fields. We are the ones setting boundaries on ourselves- using others’ expectations to carve out our realities.

“If we’re a little more open-minded about what factors really matter, quite often, we have love that’s not that far from us.”

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