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Ancient Wisdom

Publications

Matchmaking

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Ancient Wisdom

Services
Publications

Publications

Matchmaking

Services

Events

Love Quiz

Get Date

Ancient Wisdom

SPEAKINGS

Make the connections that shape a meaningful life.

Cassindy Chao brings practical relationship wisdom, leadership insight, and a matchmaker’s perspective to rooms that want more honest connection.

Cassindy Chao Featured In


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.

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.

Cassindy Chao speaking at an event
Cassindy Chao speaking at an event

THE SPEAKER

Relationship strategy, delivered with candor and warmth.

A former Goldman Sachs and J.P. Morgan banker, Cassindy is the founder of Ancient Wisdom, Modern Love and author of Ancient Wisdom, Modern Love: A Practical Guide to Modern Dating. Her keynotes translate the psychology of trust and belonging into practical strategies for business and life.

A former Goldman Sachs and J.P. Morgan banker, Cassindy is the founder of Ancient Wisdom, Modern Love and author of Ancient Wisdom, Modern Love: A Practical Guide to Modern Dating. Her keynotes translate the psychology of trust and belonging into practical strategies for business and life.

Executive experience

Custom programs

SIGNATURE TOPICS

Conversations that move people forward.

01

Make a first impression that lasts

A grounded, actionable session on confidence, authenticity, and creating trust before you say a word.

01

Make a first impression that lasts

A grounded, actionable session on confidence, authenticity, and creating trust before you say a word.

02

The psychology of trust and connection

Matchmaker lessons for stronger relationships in teams, networks, partnerships, and the rooms that matter most.

02

The psychology of trust and connection

Matchmaker lessons for stronger relationships in teams, networks, partnerships, and the rooms that matter most.

03

Leadership presence and influence

How to cultivate a lasting presence, expand your network, and lead with a clear point of view.

03

Leadership presence and influence

How to cultivate a lasting presence, expand your network, and lead with a clear point of view.

04

Modern dating, lasting partnership

A sharp, generous look at dating decisions, relationship readiness, and the modern path to finding your person.

04

Modern dating, lasting partnership

A sharp, generous look at dating decisions, relationship readiness, and the modern path to finding your person.

Cassindy Chao speaking at the Harvard Club of New York
Cassindy Chao speaking at the Harvard Club of New York

WORKING WITH CASSINDY

Focused & Engaging Presentations

Past Topics Include:

  • Navigating Work Relationships for Career Success

  • Belonging: Creating a Culture Bringing People Together to Achieve Goals and Objectives

  • Modern Dating 101 - An Evening with Matchmaker Cassindy

  • Dating as an Asian-American: Finding our Voices

  • How a Professional Woman Finds Their Partner in Life

How It Works

Step 1. Schedule a call to discuss your organizations goals and needs

Step 2. We work with you to develop a customized program

Step 3. Increased morale and energy for your audience to thrive and grow!

WORKING WITH CASSINDY

Speaking Topics

Make a First Impression That Leaves People in Awe (Even If You Don’t Totally Believe in Yourself Yet

  • Why So Many People End Up Single in Their 40s—and How to Make Sure You Don’t Regret It

  • Lessons from a Matchmaker: The Psychology of Trust and Connection in Business & Relationships

  • The Art of Influence: How to Cultivate Leadership Presence & Expand Your Network

Working With Cassindy

01 — Discover the audience, needs, and outcomes

02 — Develop a customized program

03 — Leave the room with real momentum

Cassindy Chao speaking at the Harvard Club of New York
Cassindy Chao speaking at the Harvard Club of New York

Gatherings

Matchmaker Cassindy Mahjong and Dumpling

Dumpling and Mahjong

Piedmont, CA

Come join us for a fun afternoon of dumpling making and mingling while playing Mahjong! Email us at hello@awmlove.com to be added to our waitlist

Dating Mixer by Cassindy Chao x Coffee Meets Bagel

Sorry Not Sorry LA

This events have already taken place. Thanks to everyone who joined us in 2025!

Summer Dating Social

Sakura Bistro SF

This events have already taken place. Thanks to everyone who joined us in 2025!

Faqs

The Strategy of Love

Ancient Wisdom, Modern Love

The Asian-American Dating Experience

Building Power Couples

Ready for a real introduction?

If your result makes you curious about what a personal introduction feels like, let’s talk. The first call is free — and it might be the most important conversation you have this year.

You must be at least eighteen (18) years of age to access or use AWM Love ("Service"). By using the Service, you represent and warrant that you are at least 18 years old and have the legal capacity to enter into this agreement.

You must be at least eighteen (18) years of age to access or use AWM Love ("Service"). By using the Service, you represent and warrant that you are at least 18 years old and have the legal capacity to enter into this agreement.

You must be at least eighteen (18) years of age to access or use AWM Love (“Service”). By using the Service, you represent and warrant that you are at least 18 years old and have the legal capacity to enter into this agreement.

You must be at least eighteen (18) years of age to access or use AWM Love (“Service”). By using the Service, you represent and warrant that you are at least 18 years old and have the legal capacity to enter into this agreement.