Nicole Middleton is a CERTIFIED FINANCIAL PLANNER™ with her firm, Strategy Squad, which she co-manages with her father, a Certified Public Accountant. The firm focuses on financial planning and investment management, especially for women and people of color. As fiduciary advisors, Strategy Squad is committed to working on behalf of their clients’ best interests, even when that’s less profitable for their business. They offer hourly planning, flat fee planning, investment portfolios, and insurance products that are within this fiduciary standard.

Co-managing a business wasn’t always the trajectory that Nicole had envisioned for herself. She had already found success as a producer and writer in the entertainment industry, but felt unfulfilled. She took some time off to travel abroad to reflect, and when it came down to it, she had a realization: “I care about empowering women. When I look at my own family and in our community, the women are holding it down, always getting stuff done. But we don’t take the time to educate ourselves about money. Women would be much more powerful if we knew how money and finance work.” Nicole headed back to school to get her graduate degree in financial planning at Golden Gate University. 

Fueled by her passion, Nicole passed the extremely rigorous Certified Financial Planner (CFP) exam–a six-hour exam with only one break–and even managed to do it while she was pregnant. She spent a year at Merrill Lynch, working on a team that managed money for accredited investors. This experience exposed her to the world of private equity and alternative investments, allowing her to gain insight into sophisticated investment styles and strategies.

Through that experience Nicole also saw inequities in the way that wealth management was being marketed as opposed to how it was actually delivered. Women and people of color seemed to be completely left out of the picture. “It was frustrating to not be able to work with anyone I knew–the clientele they wanted fit in a specific box: people in their sixties who had amassed incredible amounts of wealth. It was totally out of touch,” remembers Nicole. She knew it could be done in a different way.

Inspired by her parents, who are both independent accountants, she jumped at the chance to work with her father by bringing her complementary skills as a CFP® to a shared practice. Although the move was rewarding, her departure from the big firms was a bit earlier than she had initially planned. She was inspired by the women leaders of the Oakland African American Chamber of Commerce, who recommended her for the Entrepreneurs-in-Residence program at Main Street Launch. “The stage we were at, it was make-it-or-break-it time. They scooped us up right when we needed it and connected us with the right knowledge and resources. Having that enthusiasm that ‘you can do this and we can show you how’ have been instrumental,” says Nicole.

As a woman of color, Nicole sometimes feels lonely as an entrepreneur striking out on her own. But the EIR program has helped create a sense of family and community that supports her to build the confidence to forge ahead. “I think the program is well constructed with the cultural sensitivity, which is so rare in this entrepreneurial world. People of color are not thought of when people think of startup businesses, they think of a white guy in Silicon Valley wearing a sweatshirt and jeans or something,” says Nicole. Beyond the support of Main Street Launch and her fellow EIRs, Nicole also credits the program’s network of partners as a key to long-term success: “it helps you build connections in the community that you need to survive.”

To schedule a free consultation with Strategy Squad, contact Nicole at or call 888-657-7823. You can learn more about the comprehensive financial advising services Strategy Squad offers by visiting their website at