Serial entrepreneur Cassindy Chao worked in finance for a decade before starting over completely. Now she’s an elite professional matchmaker with two thriving businesses: Ancient Wisdom Modern Love and Boutique Matchmaking.
“It really interests me to bring good people together,” Chao says. “I love it when people drop their initial blockers and open up to finding someone who supports them. I love watching them enjoy each other’s company, create a bond, and eventually come to weather life challenges together instead of alone.”
The making of a matchmaker
Chao started her career as an investment banker for J.P. Morgan and Goldman Sachs. After that, she founded two Bay Area technology startups and consulted on strategic turnarounds for other companies.
“I did fine, but I just didn’t love it,” she says when asked why she left. “It was the people I enjoyed meeting and learning from — not the work.”
Chao hasn’t completely left the startup world behind, however, continuing to serve as an angel investor for The Lounge Booth, which offers mobile video production for experiential marketing purposes and special events.
Her two successful matchmaking enterprises have brought her true joy, allowing her to focus on her long-standing passion for connecting people.
“Once, while I was in college at Wellesley, I ran a Blind Date semi-formal event,” she remembers. “It was a huge success, bringing in lots of funding for the Asian Association. I loved it so much and was so engrossed interviewing people and matching them that I had to drop two classes that semester.”
Chao’s initial inspiration came from a feature about a matchmaker by chance. “The article said she had trained with one of the top matchmakers, so I found that mastermind class and joined it two years later,” she says. “I dabbled with matchmaking part-time while still working in finance, but I finally jumped out, and now I do it full-time. I’ve never looked back. It’s so much better. It’s the job I’ve always wanted to have.”
Chao’s matchmaking magic
Chao brings a unique, personal touch to her work as a matchmaker. “There are many matchmakers offering all sorts of services,” she says. “I bring an old-school, common-sense approach to this. I rely on what my parents taught me.”
In addition to curating matches, Chao gives talks and hosts live events. “I do anything and everything to foster the human connection that’s so needed in today’s post-pandemic, stressed-out world,” she adds. “I want people to focus on what really matters.”
Chao also coaches clients on dating skills. “For instance, I teach clients not to play the flute for the cow — that’s a Chinese proverb,” she says. “In other words, when they are on a date, they need to know their audience and not just yammer on with some story of their prowess that’s actually yawn-inducing.”
Her two matchmaking businesses help people of different kinds. Ancient Wisdom Modern Love focuses on Asian American communities, while Boutique Matchmaking serves high-worth individuals of all backgrounds.
“My goal is to build solid relationships,” Chao explains. “A marriage is a very important decision. Getting it wrong is exceptionally expensive in time, money, and emotion, so doing this right matters. I’m not smarter than my clients, but I’ve seen more relationships than them, and I know how to position it right.”
Chao’s secrets to business success
If there’s one thing Chao wants you to take away from her story, it’s that you’re never too old to start doing what you want to do.
“We can all have second, third, or fourth careers in life!” she says. “Starting over later in life is not an issue. I’m 56 and having an absolute blast in my job, learning so many interesting things from my clients.”
If you decide to start your own business, however, Chao has some advice. “Know your own strengths and weaknesses,” she says. “This might sound trite, but all too often, we try to compensate for our weaknesses, and that is a huge time sink.”
Instead, she recommends finding experts who have the strengths you lack.
“Recruit your own personal Board of Directors,” Chao says. “We all need solid, candid feedback to build a good business. You won’t always like what they say, but it’s said with an understanding of who you are and where you want to go. Personally, I rely on my Wellesley siblings — my freshman roommate is the first person I go to with new ideas.”
It’s never too late for your match made in heaven
Chao warns that building a new business is “difficult” and “not glamorous at all.” “Yet the more I’ve honored my own strengths, the smoother it has become,” she says.
The same holds true for relationships. “It’s never too late,” Chaos says. “If you build it, it will happen.”
