About

Cassindy

Cassindy Chao is a renowned speaker, matchmaker, investor and author. 

Hi, I’m Cassindy! I started out my career over at Goldman Sachs and while working (way too much) there, I was exposed to being on CNN, being featured in the Wall Street Journal and on stage speaking to over 2,000 attendees at investment conferences. As overwhelming as that was, with all the anxiety it caused to the point where I would hyperventilate and worry I would forget what I was talking about or even fall down, my banking career opened the world of a Chinese-American kid in LA and my world to traveling all over Asia, Europe and even to Kazakhstan to see a satellite launch. 

However, banking, the numbers part, just wasn’t right for me and I wanted to make a pivot. But before I did, I met this man named Fred through a friend. Initially, I was flirting with this Australian dude, Fred won out. He was a software developer and quite mellow at that. He wasn’t anything like the Ivy-league finance bros and the crowd I was used to, so I just wasn’t quite sure what he could do to fit into my high-flying life. I thought he was not particularly sophisticated and was a little hesitant to talk to him or see him, but then I remembered how our conversations were just so easy and comfortable, making me think of the ancient Chinese proverb, Matching Doors, Matching Windows (men dang hu dui). The proverb implies that sharing values around marriage, family and children is what matters more than any other superficial value that people go after, like wealth or fame. 

So I stuck to my roots and gave him a chance. I’m so glad I did, because the way he wooed me with his sense of humor, intellect, values, heart-of-gold, and my interests like homemade chocolate desserts, just absolutely won me over.

Even better, my parents loved him. My mother had cancer and during those years, Fred was patient, responsible and a solid support. Always. That is more priceless than any degree or credential. 

We’ve had a prosperous marriage for over 25 years with three amazing children. In that time, we’ve fostered 20 cats and counting, but have two permanent residents that live in our home. One of them is cross-eyed and is a load of fun! But he also does eat everything in sight…

I also take my 91-year-old father, who we take care of, to his weekly mahjong games where I teach over 50 students how to play, which he loves as well. Can you believe Julia Roberts said Mahjong is her absolute favorite game to play? The old always does become the new hot thing again. Thank you Julia! 

A little more about my father. He was a proud member of the Taiwan Navy, won national exams and came to America on a National Science Foundation Fellowship – His PhD thesis work was also used in Neil Armstrong’s moon trip! One of my fondest memories of childhood was when my dad rappelled with me off of a cliff during one of my army R.O.T.C. outings! Who knew that one day in the future, I would have been riding in an open doorless helicopter barely strapped in, and learning how to operate an M60 and fieldstripping my M16 with ease. 

Transitioning from Banking at Goldman and JP Morgan to Matchmaking

For a period of time, I decided to take a step out of the career role in banking as mentioned earlier (which Business Insider covered) to take care of my aging parents. While doing this, I suppose you can say my roots emerged. My mother and my grandmother were both matchmakers. I suppose that held some of the natural progression for the next step of my career as a matchmaker, being handed down the ranks into the third-generation of matchmaking. 

I’ve been helping my clients, who range from CEOs to doctors and artists (even a ballerina), navigate modern dating with a mix of ancient wisdom and contemporary strategy.

Who knew how prosperous this would be, as it’s already turned into over 50 happily ever afters and many more to come. Learn more about my matchmaking, coaching and dating course here. 

Maybe it could be because I take a wholesome, heartfelt approach to ensure each match that I introduce my clients to are both at the same place for what their hearts truly want, as opposed to the superficial matters that many of us have become accustomed to. However, I do want to make it clear that I do have a keen eye for red flags as well, because no one deserves to be with someone who has ulterior motives and isn’t truly in love with them. 

Evolving into a Speaker Who Speaks at Corporations, Conferences and Events

Most people can’t see it. However, there are stark similarities between the workplace and dating. They can range from:

  • Building a trusted network for yourself within a much larger organization

  • Understanding the psychology behind what your boss is looking for (that will propel your career forward)

  • How to be memorable when you are ending a conversation 

  • What CEOs can learn from leading with empathy and warmth in the modern era

  • The unusual lessons that dating teaches us about networking

  • Standing out and sharing your actual impact through personal branding 

  • Forget about working hard – what really matters is about making an impact

  • Uncovering your true value – even if you don’t know what it is

  • The hurtful truth about why we are our own worst enemies and lead ourselves down a path of self sabotage

  • How to give feedback without hurting the other person’s feelings (and make them like you even more after)

  • How listening and a little love can motivate a dysfunctional organization and bring it back to life

  • Its not about how hard you work but all about how loudly you shout

  • And so many more

These similarities, along with the insights I discovered, both through my career in banking and matchmaking, along with my nonprofit work in the field of autism, have really opened up my eyes to how people and businesses can thrive in any environment, from corporate America to the dating realm.

I regularly do speeches and hold events at places like MOCA, Chief, the Harvard Club, Penn Club, Hana House and even spoke at Oracle once. In addition to appearing on CNN and the Wall Street Journal, I’ve also been fortunate enough to appear on ABC News, Voyage LA, podcasts like Family Office Exchange, Asian Boss Girl, The Ken Fong Podcast and more.

If you would like to learn more about my speaking and would like to give me the honor of sharing the wisdom I have acquired over the years at your company or event, feel free to peruse through my speaking page! https://www.awmlove.com/speaking

I find it quite interesting that I am even able to do speeches, or host in-person events as well. Just a few years ago, I was in my bashful era. I was so shy and couldn’t even picture myself speaking in front of an audience. Yet, here we are and I’ve spoken to thousands upon thousands of people through various events around the country and overseas - even in Hong Kong. 

I know that I owe most of this success to my alma mater. Back when I was at Wellesley College, I once threw a 100-person mixer and in the process got my first D+ grade in a class as I was having way too much fun. So I suppose college does have a knack for shaping who you become in the future. I just love being at events, speaking, matchmaking both love interests and business owners together, and conjoining relationships and business together so others could make an impact across their lives.

Work in the Community, the Events I Hold and Other Interesting Tidbits

I am passionate. I love growing communities. I love being with good people working together to help our community and also ourselves too! Super fortunate to grow in my communities as well, as my time in the field has led to me becoming Co-President of the Wellesley College Asian Alumnae Alliance running events nationwide and in Asia, a Development Committee member for Asian Health Services, and an Associate Board Member for the New York Asian Film Festival.

In addition, I’ve written an Amazon bestselling book named: Ancient Wisdom, Modern Love: Chinese Wisdom for Dating Success, which you can learn more about here as well. (link to book)

Recently, I also founded the Entrepreneur Huddle, where we gathered entrepreneurs across various cities to gather together. However, to expand the reach of the impact of these events beyond just entrepreneurs in the Asian community, I partnered with a few others to rebrand these events as Crazy x Asian events. If you’re looking to attend an event to get to know some solid people, you can learn more about upcoming events here.

Beyond speaking at corporate events and matchmaking, I absolutely love weddings. I believe in seeing the good in people and illuminating their strengths. I find that a lot of my work isn’t just about helping others find love; it’s about helping them recognize their own worth. 

I love hosting intimate matchmaking dinners, whipping up delicious meals, and ensuring my home remains a warm, lively place filled with laughter and good food for my family, our guests and the lovely felines we get to foster and take care of. Ask me for any of my recipes! I even have a kiln oven shipped over from Asia specifically to make naan like chinese stuffed breads. And I’m the fastest dumpling wrapper – the secret? I use a small ice cream scoop. 

Oh, I’ve also been dabbling in investments, and one of the most successful ones is The Lounge Booth. Go check them out!

If you ever want to get a hold of me, please do not hesitate to reach out to me! I’m readily available for speeches, helping you meet the love of your life and tossing events with like-minded people who want to grow and become more than they already have become!

Ciao for now!