Q: What inspired your transition from investment banking to matchmaking, and how has your background in finance influenced your approach to matchmaking?
CC: I always enjoyed meeting new people and learning about them. Finance was a practical skill to have but it was not a career that I truly enjoyed. In college, I had organized a dating event, and I always remembered it being so much more fun. 

Q: Your book, "Ancient Wisdom, Modern Love," blends traditional Chinese proverbs with modern dating advice. Can you share a bit about the inspiration behind this unique concept?
CC: It’s really a love letter to my parents. While matchmaking, it is important for me to provide some guidance and coaching to my clients so that they can avoid inadvertently repeating mistakes. Using these phrases is a light-hearted and memorable way to share advice - and it’s so much nicer to use them than to say directly that one is not doing well on a date. What is also so lovely is that this transcends just my Asian American heritage as these proverbs are evocative and light-hearted. 

Q: Boutique Matchmaker caters to high-net-worth individuals and families. What sets your matchmaking practice apart, and what unique challenges do you face in this niche market?
CC: My background and experience at renowned financial institutions, Goldman Sachs and JP Morgan and my Wellesley education make me a very good fit for understanding and working with this clientele. As a married mother of three young adults, I’m particularly sensitive to working with quality individuals and helping them find great partners with the goal of long-term relationships that last a lifetime.

Q: Representation and diversity are important aspects of your work. How do you ensure inclusivity and cultural sensitivity in your matchmaking practice, especially for the AAPI community?
CC: In 2024, relationships between two people often span cultures and it is important to have that sensitivity and understanding. 

Q: Can you share a success story from your matchmaking career that particularly resonates with you, and what made it memorable?
CC: One of my pandemic marriages was between two mature adults who would not have met without a matchmaker. Online dating was not working well for them. Each spent a lot of time with their family and being so giving to others yet did not prioritize themselves. It was very special to introduce them both later in their lives and then to be so delighted when they bonded over a shared interest in classic films and later were married and so caring for each other. 

Q: In your opinion, what are the key factors that contribute to a successful and lasting relationship, and how do you help your clients cultivate these qualities?
CC: Ultimately, most relationships are about chemistry but also respect. When we want our partners to thrive and not only think about ourselves, but that’s also where the magic can happen. 

Q: What are some common misconceptions people have about dating, and how do you address them in your matchmaking practice?
CC: People often will have a checklist of characteristics they want in a partner, but often they do not understand how they are important - or not. Sometimes it’s helpful to look inwardly at our own insecurities and evaluate why we think certain characteristics such as a full head of hair in a man is more important than moral character and trustworthiness. 

Q: With the evolution of technology, what insights can you offer about finding genuine connections in a digital age?
CC: A/I has made things very interesting. While there are tools that can help us with conversations and bantering, now we don’t know who we are really talking with. The ultimate goal of any app is to meet in person. Genuine connections and conversations come from meeting in real life. 

Q: How do you navigate cultural differences and diverse backgrounds when matching clients, and what role does cultural compatibility play in successful relationships?
CC: It really depends. Some clients are interested in intercultural relationships, yet many are not. There is no rule or expectation. But irrespective of these differences, what ultimately matters are similar values, approaches, and mindset. 

Q: What do you believe is the number one misconception people have about finding love, and how can individuals overcome this misconception to enhance their dating experiences?
CC: There are many misconceptions - One very dangerous one is that somehow our life partner will complete us. That cedes all responsibility and expectations onto this partner vs any accountability for our own actions. 

Q: What advice would you give to someone who feels disillusioned or discouraged by the modern dating process?
CC: Everyone I know who has made it a priority, will find their special partner. It takes time, but it’s worth it. 

Q: What is one word of advice you can offer to young women who want to reach your level of success?
CC: Go Bold or Go Home. 

Q: Can you tell our audience one of your most memorable moments of your career?
CC: Many actually. From speaking at a Goldman Sachs conference to an audience of 2000 to being on TV on CNN. 

Q: At the start of your career, what do you wish you had known? 
CC: To draw boundaries better and know I could do that. 

Q: Which woman inspires you and why? 
CC: Ruth Bader Ginsberg- tireless, noble, and inspirational.

Q: What advice would you give to young women who want to succeed in the workplace?
CC: Go bold. Being quiet will not be rewarded. 

Q: After high school, where did you feel your career path would take you? 
CC: Back then my parents either wanted me to be an ‘administrator' or go into the sciences, obviously I didn't do either. 

Q: Can you tell us how you manage your work life balance?
CC: It’s hard! There is no perfect balance, but over time it works out. Sometimes, I am very focused on family, then other times on work - it’s a cycle. There are seasons in how we live our lives and raise our families, care for our elders, and balance our own career growth. 

Q: What is your advice for women in male-dominated fields?
CC: Always keep a private board of directors of your own of people you trust to go to for advice on career moves. 

Eight Things About Cassindy Chao

1. What is your favorite thing to do in your free time? 
I am the world’s best afternoon napper. At every single job - even right after college - I would find ways to take mini naps, the nurses lounge, under my desk

2. Among your friends, what are you best known for? 
My friends call me a rhino - in a loving way - for getting things done

3. What TV shows did you watch when you were a kid? 
I dream of Jeannie, Gilligan’s Island, Love Boat

4. What is your favorite quote or saying? 
Go bold or go home

5. Are you a morning person or a night owl? 
I am a total morning person

6. What’s your big passion? 
I love to cook - I can also cook in almost any kitchen; I’ll figure it out

7. What is your favorite game or sport to watch and play? 
I’ve learned to really enjoy watching football. I think Mahomes' voice is really funny

8. What were you like in high school? 
Still finding myself. It’s good that I flubbed a few courses to know what I was really bad at. (calculus and economics