Cassindy Chao - Keynote Speaker & Asian Matchmaker
Cassindy Chao speaks on relationships as strategic assets — how trust, compatibility and connection drive team performance, retention and leadership. A third-generation Chinese matchmaker and former Goldman Sachs and J.P. Morgan banker, she has spoken at the Harvard Club of New York, the Penn Club, Ascend, NAAAP and the Marshall Seminar. She works with corporate ERGs, university clubs, professional associations and conferences.
She is the founder of Ancient Wisdom, Modern Love, an elite matchmaking practice for high-net-worth professionals. She is also the author of the best-seller Ancient Wisdom, Modern Love: A Practical Guide to Modern Dating.
With her background in investment banking at J.P. Morgan and Goldman Sachs, Cassindy understands high-stakes relationship management and personal branding. She is also an angel investor, and serves in multiple leadership roles for non-profit organizations. She is a recent graduate of the Goldman Sachs 10,000 Small Businesses program - National Cohort 25.
Featured in Business Insider, CHIEF, and Janet Hanson’s book More Than 85 Broads, and speaker at notable university clubs. Cassindy shares actionable relationship strategies with executives and professionals so they can cultivate connections that drive success in both business and life.
Leadership and Corporate
Relationships Are Not Soft Skills
Trust, compatibility, and connection get filed as personality traits when they are actually operating skills. The cost shows up in retention, in team performance, and in capable leaders who cannot get their good ideas adopted. A former Goldman Sachs and JP Morgan executive turned executive matchmaker makes the business case, then gives teams the practical version.
The Presence Problem: Why Capable People Get Overlooked
Being the most prepared person in the room is not the same as being the person the room listens to. This session is about the gap between competence and presence, what actually creates it, and what closes it. Specific and practical, not a lecture on confidence.
Founders and Business Development
Be Chosen: How Founders Win the Room
Founders raise, recruit, and sell on the same mechanics that decide whether anyone is chosen in any other context. The investor meeting. The first customer call. The candidate weighing three offers. Cassindy spent two decades in global finance and technology at Goldman Sachs and JP Morgan before building an executive matchmaking practice, and she now works full time on how trust forms and why one person is unforgettable while the next is not.
What High Achievers Get Wrong About Relationships
The pattern is remarkably consistent across accomplished professionals: the exact strategies that built the career work against the relationship. This session names the pattern, explains why it persists among people who are excellent at everything else, and offers a different approach. Candid, occasionally uncomfortable, and the one audiences quote back afterward.
Affinity, Alumni, and Cultural Sharing
Formats
Keynote, 20 to 45 minutes
Interactive workshop, 60 to 90 minutes, best at round tables of six
Fireside chat or moderated conversation
Modern Love and the Asian American Experience
Family expectation, cultural fluency, and the particular pressures on accomplished Asian American professionals in dating and partnership. Built for employee resource groups, alumni associations, and cultural organizations. Warm, specific, and grounded in what a matchmaker actually sees rather than what gets written about.
Ancient Wisdom, Modern Love: Chinese Chengyu for Dating Success
Four character Chinese idioms as a practical framework for connection, drawn from Cassindy's book of the same name. A third generation Chinese matchmaker on what the old wisdom gets right, and where it needs updating. Works as a keynote or as an interactive session.
Selected Events
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![date night]()
Date Night - LA
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![Hong Kong Mixer]()
Hong Kong Ivy League Happy Hour
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![Crazy X Asians]()
LA Cocktail Mixer
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![NYC Matchmaker Mixer]()
NYC Matchmaker Mixer
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![Best asian matchmaker]()
GMF
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![best asian matchmaker]()
Robert half 5th anniversary
Speaking Topics
Modern Love & The Asian-American Experience
What does it mean to date, love, and build partnerships as an Asian-American professional today? Cassindy explores how cultural identity, family expectations, and modern dating realities collide — and how to navigate them with wisdom and humor.
What High Achievers Get Wrong About Relationships
Built for corporate audiences and professional communities. Cassindy draws on 35 years of matchmaking experience and her Goldman Sachs background to examine why accomplished professionals often struggle most with love — and what they can do about it.
Ancient Wisdom, Modern Love — Chinese Chengyu for Dating Success
A talk inspired by her bestselling book. Cassindy shares the Chinese idioms (chengyu) her parents taught her as lifelong lessons about love, relationships, and what it takes to truly connect. Insightful, culturally rich, and immediately actionable.
The Art of the Introduction — How Professional Matchmaking Works
A behind-the-scenes look at premium matchmaking for accomplished professionals. What does an Asian matchmaker actually do? What separates a great match from a good one? Perfect for community events, cultural organizations, and professional associations.
Mid-Career Transitions & Personal Reinvention
For professional audiences navigating change. Cassindy shares her own story of leaving Wall Street to pursue matchmaking — and what she learned about identity, purpose, and reinvention along the way.
Latest Coverage
In The Press
NBC NEWS INTERVIEW
NewsNation interview
Wisdom Hub - Blog
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![Two young women wearing white t-shirts and denim overalls are standing outside, leaning against a tree, smiling and laughing while eating yellow snacks.]()
9 Things to Never Do in the First Month of Dating: A Guide
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![A young man is smiling and holding a sandwich, talking to an older woman who is sitting and laughing, outdoors in front of a building with glass windows.]()
Top 9 Signs of Chemistry on a First Date
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![Two elderly people, a man and a woman, smiling and standing close together outdoors with their arms around each other, in front of green trees and bushes.]()
Checklist of Love: What to Look for in a Partner
Speaking Topics
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How high-achieving professionals can apply the same strategic discipline that built their careers to finding a life partner — drawing on Goldman Sachs analytical rigor and three generations of Chinese matchmaking wisdom. Perfect for corporate and ERG audiences.
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A keynote based on Cassindy's book — exploring how 3,000 years of Chinese matchmaking philosophy, distilled through chengyu sayings, offers surprisingly practical tools for navigating modern dating, relationships, and marriage.
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A nuanced talk on the unique cultural pressures, family expectations, and relationship dynamics facing Asian-American professionals — and how to navigate them with confidence, clarity, and cultural pride.
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For corporate and ERG audiences: how high-performing couples succeed together, balancing individual ambition with shared partnership — and why the most successful relationships are by design, not by accident.
Book Cassindy for Your Next Event
Cassindy speaks to corporate teams, ERGs, professional associations, and universities. Her talks are tailored, personal, and always grounded in both ancient wisdom and modern experience. Based in San Francisco. Available in SF, LA, NYC, and virtually.