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Making Effective Connections in 2025

A woman with short black hair, glasses, and a light purple blouse sitting on a white sofa, reading an open book, with decorative pillows, a vase of white flowers, and a cup on a glass table in a bright, airy room.

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.

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.

RECENT

SPEAKING

Events

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SPECIAL EVENTS & TALKS

  • Fri May 24, 2024

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  • Hong Kong Happy Hour: Fri Mar 28, 2025

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  • LA Cocktail Mixer Thurs Apr 11, 2025

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  • NYC Matchmaker Mixer Thurs May 8, 2025

    RSVP
Four people sitting in chairs outdoors on a stage, with trees and desert plants in the background. One woman is speaking into a microphone, while the others listen.

Speaking Topics:

  • Networking with Purpose: Building High-Value Professional Relationships

  • 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

  • Executive and former banker

  • Facilitated with candor, professionalism and warmth

  • Tailored to your organization’s culture and needs

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Group of smiling people at a social gathering, including women and a man, engaged in conversation.
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A group of people gathered in a dimly lit bar or club, with some sitting and others standing, while a woman in a pink dress sits on a bar counter, talking or performing for the crowd.
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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!

Latest Coverage

In The Press

A woman smiling at an airport, wearing glasses, a purple coat, and a pink scarf with a red heart attached, standing near airline check-in counters.

I quit my $376,000 dream job at Goldman Sachs …

BUSINESS INSIDER ARTICLE

Wisdom Hub - Blog

  • Hiring a Matchmaker: Your Path to Lasting Love

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  • Goldman Sachs to Matchmaking? Yes, THAT Kind of Matchmaking!

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  • 9 Things to Never Do in the First Month of Dating: A Guide

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  • Top 9 Signs of Chemistry on a First Date

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  • Checklist of Love: What to Look for in a Partner

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  • 5 Great Date Ideas in Palo Alto, CA

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