Alexandra Esparza Is Choosing Her Own Adventure

For Alexandra Esparza, a technology investment banker, life has always been like one of those paperback books that lets the reader make a series of choices that determine everything and everyone the main character will encounter. Her journey took her into investment banking, where she helped emerging companies find investors and grow iconic brands. But now, Esparza is writing a new chapter as she prepares to leave the lucrative world of Wall Street to explore passion projects.

The Chicago native navigated the Windy City’s public school system with adventure in her DNA. “I always knew I wanted to do a bit of exploring and see new things,” she says. That wanderlust took her across the country to Stanford University. Although Esparza once intended to study medicine or English, she pivoted to humanities and discovered a new passion for philosophy and literature. That drove her to study abroad in Oxford, expand her horizons, and realize that there are “so many ways to effect change and improve the world.” 

That became something of a personal mission statement for the young student, and one that remains intact today. Before her graduation, Esparza found a growing interest in banking, technology, and healthcare. She interned at a private equity firm and took a job in sales and trading at Oppenheimer & Co, where she focused on hedge fund and mutual fund clients with connections to hospitals, biotech, and medical tech.

After leaving Oppenheimer to complete an MBA at Yale University, Esparza went to a global small cap hedge fund before returning to Oppenheimer in 2017 to bridge the gap between healthcare startups, Silicon Valley tech leaders, and private investors.

In recent years, Esparza has had the unique opportunity to work with innovative companies and steer funding to traditionally stigmatized areas. It all started in early 2021, when she noticed record-breaking investments going to “femtech” companies that develop software, solutions, and products to address fertility, menstruation, sexual wellness, pregnancy, and other women’s health issues.

“I wanted to help unite female leaders in healthcare, biotech, and technology to serve women-focused companies,” she explains. In response, Esparza assembled an all-women investment banking team and rolled out a series of networking events to highlight opportunities in femtech.

It’s just one of many ways Esparza is using her voice to help others find theirs. She’s also part of the newly formed AWSM. Pronounced “awesome,” AWSM stands for A World Serving Many and is a nonprofit organization created to help underrepresented founders level up, close their skills gaps, and prepare to attract, receive, and implement funding. AWSM’s bootcamps, seminars, courses, and events help founders engage like-minded owners, find accountability, interact with coaches, and unlock funding.

Esparza spent the last few years advising similar groups and tackling these endeavors as she built and led the digital health and wellness investment banking practice at Oppenheimer. After twelve years, she was ready to walk away from investment banking to pursue dreams that had been on the back burner for some time. She’s working toward the launch of a tech-enabled degendered clothing line dedicated to body positivity, radical inclusion, and comfort.

Why will this new venture succeed? Esparza says it fills a gap in the marketplace and fits the current cultural moment. Plus, she can leverage everything she’s learned throughout her career. “The years I’ve spent advising start-ups and helping friends and colleagues showed me how good companies are built, how they get funded, and why they take off,” she explains.

Still, it can be tough. Esparza admits she’s at least a little bit scared to leave the well-trodden path of investment banking for the uncertainty of life as an entrepreneur. “The need for thrill outweighs the need for safety, and I don’t want to look back and realize I missed my chance,” she says. For Alexandra Esparza, the real adventure is about to begin.