Where Matchmaking Meets Business

Matchmaker | Speaker | Author

Meet Cassindy

Cassindy Chao is an ex-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 and is a devoted Wellesley alumnae.

Featured in Business Insider, AsianBossGirl, 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.

Discover how Cassindy can help you and your organization build great relationships

With candor, humor, and heart, Cassindy helps corporate teams and professionals strengthen connection—whether it’s networking with purpose, building influence, or creating cultures where people thrive.

Her talks are insightful, practical, and always leave people feeling more confident, connected, and seen.

Having decades of experience guiding high-achieving clients, Cassindy shares a thoughtful and very personalized approach to finding your partner who’s truly compatible—not just on paper, but in everyday life.

Finding your partner is one of the most important decisions in life - work with professionals who care.

Our Relationships Matter

Relationships matter beyond family and love.  Whether you're building a high-performing team or nurturing a strong leadership bench, relationships are the real engine behind lasting success. They drive trust, collaboration, innovation—and yes, retention. We don’t rise in our careers alone. We rise with the people who advocate for us, the colleagues who challenge and support us, the mentors who help us navigate inflection points.

Relationships are not “soft skills”—they are critical strategic assets.

As a speaker and longtime matchmaker (yes, professionally!), I bring a unique lens to the corporate world: I’ve spent years helping people navigate vulnerability, build trust quickly, and develop the kind of emotional intelligence that leads to powerful, lasting connections. My job is literally to study compatibility and communication—and that insight translates into complex workplace dynamics. In my talks, I blend business savvy (from my years at Goldman Sachs and JP Morgan) with cultural wisdom and a dose of humor to help people connect in ways that drive performance, belonging and thriving.

Because when we know how to build real relationships, we do our jobs better but also we’re creating workplaces where everyone feels seen, invested, and empowered.

Testimonials

  • Thank you again for your outstanding presentation at the Harvard Club yesterday. It was a pleasure to meet you and get some deep insights on how to navigate the contemporary dating scene. Your event was easily the most fun/ engaging event I've been to at the Club in a year!

    V.G. 4/6/2025

  • Cassindy’s earthy, practical, and calming advice is much needed in today’s anxiety-ridden dating world. She outlines healthy, balanced approaches and behaviors in a warm, funny and direct way.

    C.M. 10/23/2023

  • Cassindy helped us to run a terrific program for bringing local business leaders together in Los Angeles Little Tokyo and had the audience building new and meaningful connections. She cares about community building.

    Kevin C. 3/1/2025

  • Hi Cassindy, thank you for leading the inspiring breakout session with Ascend today! I appreciate the tips you shared on making powerful impact statements.

    Lina L 3/26/2025

  • Cassindy has been a matchmaker since her college days at Wellesley. She helped me identify my now husband. He is my one true love. He understands, accepts, and celebrates me. Without her sage advice, I would not be married today.

    S.C. & M.D.

  • Our backgrounds were very similar, and we had lot in common, yet we would not have met without her nudge. We fell in love the day we first met and we’ve been married ever since. Cassindy is our trusted friend for life!

    K.S. & B.N.

Featured Events

Ancient Wisdom Modern Love:

Chinese Wisdom for Dating Success

Matchmaker Cassindy Bestselling Book

SECOND EDITION: SHARED EXPERIENCES, STORIES, AND BONUS FAMILY RECIPES.

LESSONS FROM “CHENGYU” WILL CHANGE YOUR LOVE LIFE FOR THE BETTER WITH WARMTH AND HUMOR.

For centuries, Chinese people have been distilling everything from philosophical ideas to folk wisdom to advice on relationships into short, memorable, and often humorous sayings called “chengyu” (成語).

These ancient phrases and their relatable wisdom that I myself heard growing up are a core part of my matchmaking practice as I advise my clients on successfully navigating dating and building relationships.

Contact Us

Phone
(650) 395-8535