Cassindy Chao

CEO and Matchmaker @ Ancient Wisdom || Modern Love

About

As a lively public speaker, community leader, and former executive with 25+ years of experience in finance and technology, I excel at building meaningful connections and fostering growth. I bring a professional and strategic approach to relationship-building, whether it's empowering executives, guiding professionals, or strengthening communities in San Francisco, Los Angeles, and New York. I am so very passionate about creating purposeful relationships that thrive on shared values, mutual respect, and collective success. Deeply connected to the Bay Area's philanthropic landscape, I also proudly contribute as an Amazon bestselling author of Ancient Wisdom Modern Love and as an alumna of the prestigious Marshall Memorial Fellowship. Let’s connect to discuss public speaking engagements, community initiatives, or other opportunities where impactful relationships make a difference.

Country

United States

City

San Francisco Bay Area

Industry

Media Production

Skill

Investment Management, Organizational Development, Restructuring, Business Restructures, Investments, Working with Investors, Executive Coaching, Networking, Financial Modeling, Writing, Organizational Leadership, Change Management, Fundraising, Life Coaching, Business Strategy, Program Management, Strategic Planning, Business Development, Management Consulting, Strategy

Experience

CEO and Matchmaker

Ancient Wisdom || Modern Love

2013-1 - Present · 13 yrs 9 mos

San Francisco Bay Area

* Bespoke matchmaking for executives and professionals with deep connections and database. * Experience and expertise with top finance and tech executives, scientists, creatives, & more. * Practice Focus Niche: Asian-Americans, High net worth, professionals.

Co-Founder

Boutique Matchmaking

2023-1 - Present · 3 yrs 9 mos

United States

* Selected Matchmakers by venerable Family Office Exchange for thought guidance with ultra high net worth families and individuals navigating relationships.

Associate Board

New York Asian Film Festival / New York Asian Film Foundation

2024-6 - Present · 2 yrs 4 mos

New York, New York, United States

Joined Associate Board supporting the reknowned NY Asian Film Festival showcasing cinematic talent to audiences globally.

Co-President & Board Member

W3A: Wellesley Asian Alumnae Alliance

2023-7 - Present · 3 yrs 3 mos

Leading Asian alumnae of Wellesley College - Global outreach, activities, advocacy.

Business Advisor

The Lounge Booth

2023-4 - Present · 3 yrs 6 mos

Orange County, California, United States

* Support business development and closed fundraising round for media startup with blue-chip clientele including Lionsgate, Netflix, Spotify, and gaming and product promotions and high profile events.

Business Development/Consultant

Kelleher International

2022-9 - 2024-6 · 1 yr 10 mos

California, United States

Chief Executive Officer

Proxifile Inc.

2020 - 2022-5 · 2 yrs

* Creator of ClaaS: Claims as a Service: Helping creditors navigate the bankruptcy claims process * Platform offers ease of use for creditors to resolves complicated and confusing bankruptcy claims issues

Founder and Partner

C2Pragma

2012 - 2019 · 7 yrs

San Francisco Bay Area

Strategic advisors to companies in transition, with representative engagements including: * ABC Liquidation of venture-funded businesses * Global property investment portfolio review for Hong Kong based family office fund * Stake investment in listed biotech entity for family office fund

Chief Operating Officer

Say Say K, Inc.

2017-8 - 2018-10 · 1 yr 3 mos

San Francisco Bay Area

•Say Say K Launched E-learning iOS app (Lyngo - 朗果) in China and US market * Manage Engineering & Content teams in San Francisco, Menlo Park, Beijing, and Shenzhen, China *Interim COO for American Zhong Hai Tai Rui (Dandelion Ventures) *Interim COO for Prado SV 2-10/2018 (20+ seed investments)

Lead Operations

BaseBit Technologies

2016-1 - 2017-2 · 1 yr 2 mos

Newark, CA

*Led finance, legal, and administrative functions for rapidly growing bioinformatics company with operations in Silicon Valley, Shanghai and Beijing. Company moved overseas to Asia.

Education

Wellesley College

Economics, Chinese Studies

Massachusetts Institute of Technology

Completed 5 undergraduate courses: Mechanical Engineering 2.70, Macroeconomics, Microeconomics, Finance & Cost Accounting, and International Business (Sloan).