Cassindy Chao - Keynote Speaker & Asian Matchmaker
Cassindy Chao is a former Goldman Sachs investment banker turned-expert matchmaker, author, and speaker specializing in relationship-building and leadership development. 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 a 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.
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.