Navigating the delicate balance of love and legacy is a challenge for anyone, but for ultra-high-net-worth families, the stakes are even higher. Matchmakers like Cassindy Chao and Shannon Lundgren, founders of Boutique Matchmaking, who have worked with families of great wealth, understand the importance of finding the right partner — not just for love but for family stability, mental well-being and, ultimately, wealth preservation.
The road to matchmaking
Both Chao and Lundgren began their careers in corporate finance. Chao worked at Goldman Sachs and JPMorgan, while Lundgren honed her skills at Solomon Brothers and Wells Fargo.
“I caught the matchmaking bug in college at Wellesley [College],” Chao said. “As social chair, I matched over a hundred people from different colleges, and I loved it.”
Years later, while working in finance, she began to consider matchmaking as a professional path. After training with a renowned matchmaker, Chao transitioned into matchmaking full time, realizing she could blend her business acumen with her passion for connecting people.
Lundgren’s journey was similar. After working for Warren Buffett in Nebraska, she took stock of her personal life and realized she needed to focus on finding a meaningful relationship. She met her husband through a startup she was working for but continued dabbling in matchmaking on the side, eventually building a large database of potential clients.
The challenges for people of wealth
Ultra-high-net-worth individuals face unique challenges in the dating world, including privacy concerns, protecting family legacy and balancing their public and private lives. And while online dating is a popular way to meet people today, for UHNW individuals, it may not provide the privacy and security needed for them to feel comfortable.
“Online dating can be overwhelming and unsafe, especially for those who value their privacy,” Chao said. "We want to provide a safer, more personalized alternative.”
Though they recognize the role that dating apps can play in expanding social circles, Chao and Lundgren stress the importance of protecting their clients from the pitfalls of unsavory characters and digital fatigue. “There are so many tools and AI tech tools, and sometimes you don’t even know who you’re talking to,” Chao said.
The duo’s process is rigorous and highly personalized. Before Chao and Lundgren present potential matches, clients go through detailed assessments, relationship history reviews and professional photo shoots. The goal is to create a complete picture of who the client is and what they are looking for in a partner.
Once the groundwork is laid, they personally select three or four candidates for each client, presenting only the most compatible options.
“We want to make sure we’re talking about the essence of who the person is,” Lundgren said. The team even coordinates the logistics of the date itself — everything from venue reservations to post-date coaching.
Beyond wealth and legacy, matchmaking also has a significant impact on emotional well-being. Chao and Lundgren see their work as bringing joy and hope to individuals who may otherwise feel vulnerable in the dating world.
“Dating is about more than just finding a partner," Lundgren said. "It’s about helping people approach relationships from a place of joy rather than fear or anxiety.”