Cindy Fields: Finding Community and Courage on the Road from Wall Street to 'Fairy Godmother'
Cindy Fields entered her office one morning to find that her friend had left a wand and fairy dust on her desk, in honor of her ‘fairy godmother title.’ How did Fields become this character? Well, it began on Wall Street. “I didn’t intend to end up on Wall Street,” Cindy Fields said. After earning her master’s degree in social studies history, she pursued an unexpected opportunity in merchant banking, private equity, and venture capital—fields traditionally reserved for those with formal finance backgrounds. Initially lacking a degree in finance, Fields leaned on her research skills, distinguishing herself among her male peers.
Her identity as a woman proved its challenged and, surprisingly, its advantages. “I went to clubs where I was the first woman to walk through the door, since there were male-only clubs in those days,” she recalls. However, clients often found her more approachable and less threatening than her male peers, allowing for deeper, more honest conversations. Over time, Fields was able to solidify her credentials by earning an MBA in finance, further proving her capability in a competitive industry.
Fields later transitioned to merger arbitrage, engaging in high-stakes, ticker-tape trades. However, the industry faced upheaval during the infamous Boesky scandal of the 1980s. “Feds came into merger arbitrage offices and literally escorted people away in handcuffs,” she recounted. Fields was forced to pivot, and she decided to move from trading to the advisory side of Wall Street. She leveraged her experience and connections, as her former peers became her new clients.
Field’s reinvention marked the beginning of Loyalty Alliance, a firm she founded to provide advisory services to a growing number of clients. Slowly but steadily, Fields built a thriving business. Then, COVID offered another moment for reflection and reinvention. During the pandemic, Conversations with entrepreneurs sparked a realization: there wasn’t sufficient community support for business owners. This inspired Zakura, a space where entrepreneurs could connect, share ideas, and inspire one another.
“People need a place to belong,” Fields emphasized. Entrepreneurs in particular thrive when they’re part of a supportive community, especially one that celebrates individuality and innovation. “Everybody wants a fairy godmother,” she quipped. The nickname bestowed upon her by coworkers, since she helps her clients make their dreams (financial, personal, entrepreneurial) come true.
Fields’ immense experience with entrepreneurs leaves her with much advice for inspiring entrepreneurs. Be fearless. “Some people get stuck because they’re too afraid or because they haven’t done their homework,” she observes. Building genuine connections and showing authentic interest in others’ stories can open doors. “People love to talk about themselves,” she added.
Equally important is staying true to yourself. “Don’t be afraid of being different,” she says. She recalled how she embodied this ethos when she balanced her demanding career as a Wall Street banker with her passion for ballroom dancing. “I was a straight-laced banker by day and a ballroom dancer by night.”
“Anybody can be an entrepreneur,” she insisted. “Most people want the sameness of being part of a group, but entrepreneurs are willing to be different.” Yet, she cautioned, missteps can arise—whether it’s overthinking decisions, partnering with the wrong people, or failing to act on opportunities. Adaptability is also crucial. “Be prepared to pivot,” she advised. For Fields, success is deeply personal. “Get a sense of what success means to you,” she encouraged, reminding us all to pursue our dreams without excuses.
Fields’ entrepreneurial journey continues to evolve each day, but her emphasis on bringing on people and community remains constant. She emphasizes that her legacy is one of empowerment and inspiration. And yet, Fields never could have predicted that this is where her career would end up when she was just entering Wall Street. Indeed, she reflected, “Where I am is not where I started.”