Cassindy Chao
| Other names | Cindy Chao |
|---|---|
| Born | Queens, New York, U.S. |
| Alma mater | Wellesley College (BA, 1990) |
| Occupations | Professional matchmaker, writer, speaker, angel investor |
| Known for | Ancient Wisdom, Modern Love (book and matchmaking agency) |
| Spouse | Fred |
| Children | 3 |
Cassindy Chao (also referred to as Cindy Chao; Chinese name: 趙珊珊, pinyin: Zhào Shānshān) is a United States-based professional matchmaker, author, angel investor, and public speaker. Previously holding investment banking roles at J.P. Morgan and Goldman Sachs, Chao established the boutique matchmaking firm Ancient Wisdom, Modern Love (frequently abbreviated to AWM Love or AWML). She also penned the 2024 publication Ancient Wisdom Modern Love: Chinese Wisdom for Dating Success.[1][2] Chao identifies herself as continuing a family legacy as a third-generation matchmaker.[3]
Childhood and education
Born in Washington, D.C. to Taiwanese immigrant parents, Chao relocated to the Los Angeles region at the age of five. She spent her formative years in Redondo Beach and, subsequently, Palos Verdes, California.[2] Her father, a former member of the Taiwanese Navy, relocated to the U.S. after receiving a fellowship from the National Science Foundation.[4]
For her higher education, Chao enrolled at Wellesley College, where she completed a dual Bachelor of Arts degree in economics and Chinese studies in 1990.[5] During her undergraduate years, she coordinated a massive campus social mixer, an event she later pinpointed as the catalyst for her passion for matchmaking.[2][4]
Professional background in finance
Following her graduation, Chao built a career in the financial sector, taking on roles in equity research and investment banking at major firms like J.P. Morgan and Goldman Sachs.[2][4] Throughout her tenure in banking, she was invited to speak at various investment summits, was profiled in The Wall Street Journal, and made appearances on CNN.[4] She later disclosed that a primary motivation for stepping away from the finance industry was to provide care for her aging parents.[6]
Matchmaking business and authorship
Chao is the founder of Ancient Wisdom, Modern Love (also known by the acronyms AWML and AWM Love). The firm provides dating coaching and exclusive matchmaking services tailored to high-net-worth individuals and career-driven singles, emphasizing introductions for Asian and Asian-American professionals.[1][2] Noting that both her grandmother and mother facilitated matches, Chao describes herself as a practitioner of the trade in her family's third generation.[4][3]
As an author, she published Ancient Wisdom, Modern Love: Chinese Wisdom for Dating Success (sometimes bearing the subtitle A Practical Guide to Modern Dating). The dating self-help guide utilizes traditional four-character Chinese idioms, known as chengyu, to dispense relationship advice. A revised second edition incorporates family recipes and personal anecdotes.[1][3][7]
Speaking engagements
In addition to matchmaking, Chao is an active public speaker whose presentations explore leadership, professional networking, and relationship building, frequently highlighting the similarities between corporate dynamics and dating.[4][8] Her speaking portfolio includes appearances at prominent organizations and venues such as Robert Half, Oracle, the National Association of Asian American Professionals, Ascend, the Museum of Chinese in America, the Penn Club, and the Harvard Club of New York.[4]
Additional ventures
Chao is involved in angel investing, with The Lounge Booth being among the enterprises in her investment portfolio.[4] Furthermore, she launched a professional networking initiative originally called the Entrepreneur Huddle, which was eventually rebranded as the "Crazy x Asians" event series.[4]
Within the nonprofit sector, Chao has contributed as a development committee member for Asian Health Services, held the position of Co-President for the Wellesley College Asian Alumnae Alliance, and sat on the associate board of the New York Asian Film Festival.[1][4] She is also an instructor of the game mahjong.[4]
Press and media appearances
Chao's transition to matchmaking has attracted coverage from numerous media entities. She has been highlighted by ABC News, NewsNation, NBC News, Business Insider, and Voyage LA. Additionally, she has been a guest on digital broadcasts including the Ken Fong Podcast and AsianBossGirl.[1][4] Chao is also referenced in the book More Than 85 Broads, authored by Janet Hanson.[1]
Personal life
Residing in the San Francisco Bay Area, Chao is married to software developer Fred.[9] The couple has shared over two and a half decades of marriage and raised three children.[4][3] Outside of her professional life, Chao enjoys cooking traditional Taiwanese cuisine and fostering rescue cats.[4]
See also
Bibliography
- Ancient Wisdom, Modern Love: Chinese Wisdom for Dating Success (Stone Monkey Publishing; 2nd edition, 2024)[7]
References
- ^ a b c d e f "Matchmaking & Speaking with Cassindy Chao", cassindy.com. Retrieved 22 June 2026. https://www.cassindy.com/home
- ^ a b c d e "Meet Cassindy Chao of Ancient Wisdom Modern Love", Voyage LA Magazine, 11 March 2024. Retrieved 22 June 2026. https://voyagela.com/interview/meet-cassindy-chao-of-ancient-wisdom-modern-love/
- ^ a b c d "Cassindy Chao – author page", Amazon. Retrieved 22 June 2026. https://us.amazon.com/stores/author/B0CKQD2D3C
- ^ a b c d e f g h i j k l m n "About Cassindy Chao", cassindy.com. Retrieved 22 June 2026. https://www.cassindy.com/about
- ^ "Cassindy Chao ('90)", Wellesley College, East Asian Languages and Cultures. Retrieved 22 June 2026. https://www1.wellesley.edu/ealc/alum-corner/chinese-alumnae-corner/cassindy-chao-90-
- ^ "I quit Goldman Sachs to take care of my mother", Business Insider, 2024. Retrieved 22 June 2026. https://www.businessinsider.com/quit-goldman-sachs-to-take-care-of-mother-no-regrets-2024-5
- ^ a b "Ancient Wisdom, Modern Love" (book listing), Amazon. Retrieved 22 June 2026. https://www.amazon.com/dp/B0CKQ8QTJB
- ^ "Speaking – Cassindy Chao", cassindy.com. Retrieved 22 June 2026. https://www.cassindy.com/speaking
- ^ "Cassindy Chao", LinkedIn. Retrieved 22 June 2026. https://www.linkedin.com/in/cassindy/
