The Darden Network Jumpstarts a Startup

By Dave Hendrick

Benjamin Pitts (MBA ’09) was working at a job he enjoyed at one of the world’s premier financial institutions when he decided to scrap it all and start over.  Six years later, in a story that serves as a testament to the network at the University of Virginia Darden School of Business, Pitts is now the CEO of a startup formed with four Darden graduates he met along the way.

A former private wealth advisor at Goldman Sachs, Pitts said he enjoyed counseling high net worth individuals on their investment portfolios. What he enjoyed more than the advising, however, was hearing the stories of the entrepreneurs he encountered and studying their habits.

“I enjoyed wealth management,” Pitts said. “While at Darden, I knew that wealth management would give me broad exposure to a lot of different people and sectors. It’s a great career for people who want to learn what other people are doing to be successful.”

However, as Pitts recounted in a LinkedIn post that drew more than 100 comments and was shared hundreds of times, a funny thing happened as he spent more time with entrepreneurs: He began to see himself, or at least a potential version of himself, in them.

It wasn’t the potential wealth that interested him. It was the passion and drive and charting one’s own course to solve real problems that struck a chord with Pitts.

In 2012, with a newborn at home, Pitts gave notice to leave his job, and with the help of the Darden network, began to set his own course according to his own principles.

Pitts first co-founded his own financial management firm, Cypress Financial Planning, with a former Goldman colleague. Two years later, along with fellow Darden graduates Jason Hull (MBA ’03), Mark Berry (MBA ’81), Evan Powers (MBA ’09) and Joel Light (MBA ’09), he embarked on a more ambitious project to bring financial guidance and planning tools and services to the masses via the software product myFinancialAnswers, a service first founded on the notion of being “TurboTax for financial planning.”

“We work with employers and benefits partners to provide access to high-quality financial planning for consumers who typically don’t have access to it,” Pitts said, noting the perceived gap in services between the high-end services aimed at wealthy individuals and the product-based services typically offered to the mass market.

The company’s proprietary software gathers an individual’s personal and financial information and makes a series of recommendations based on the user’s long-term goals.

Pitts knew two of the four co-founders from his time at Darden. He met Berry, who serves as the company’s CFO, while making cold calls at Goldman Sachs. Pitts reached out to Hull, who served as the company’s founding chief technical officer, after reading an article Hull wrote.

Hull had previously built a software company in Charlottesville and the two quickly realized that they could execute a shared vision. Light, a Darden classmate, offered initial seed capital and Powers, also a classmate and colleague of Pitts at Cypress Financial Planning, writes much of the content for the company.

“Our company would not exist if it were not for the power of the Darden network,” Pitts said.  “We shared the work ethic, values and a natural trust in one another that allowed us to get to work without having all of the answers. Everyone was willing to invest time and energy when it was just an idea.”

Pitts, Light and Hull are all also graduates of the U.S. Military Academy at West Point, an institution Pitts describes as similar to Darden in its “alumni who are fiercely committed to other alumni.”

Like the early days of many startups, Pitts says the company’s marketing strategy has evolved. The company first targeted only large employers, landing an onsite event at Facebook’s headquarters and conducting a pilot with Tesla Motors at that company’s headquarters.

More recently, myFinancialAnswers has focused on small- and mid-sized employers, in part due to what Pitts described as the slow sales cycle of the largest employers.

“We’ve learned a ton and are now primarily focused on partnering with employer groups between 250 and 2,500 employees,” Pitts said. “We are also partnering with the employee benefits vendors that service those groups to reach our target customer.”

The company is currently working on its first partnership with a 401k plan advisor partner in Texas, where they expect to connect with about 25 companies and gain access to about 2,000 employees. In addition, they’ve partnered with Wavelength Financial, a financial content provider to create a “full stack” financial wellness solution for small employers.

Meanwhile, Pitts continues to learn what it means to create and lead a company.

“My biggest challenge as a CEO in the early days was being a little bit unfocused,” Pitts said, noting the evolving nature of the market opportunity. “We’ve been careful not to narrow our focus too soon, but we believe we’ve found our market niche in corporate financial wellness.”

About the University of Virginia Darden School of Business

The University of Virginia Darden School of Business prepares responsible global leaders through unparalleled transformational learning experiences. Darden’s graduate degree programs (MBA, MSBA and Ph.D.) and Executive Education & Lifelong Learning programs offered by the Darden School Foundation set the stage for a lifetime of career advancement and impact. Darden’s top-ranked faculty, renowned for teaching excellence, inspires and shapes modern business leadership worldwide through research, thought leadership and business publishing. Darden has Grounds in Charlottesville, Virginia, and the Washington, D.C., area and a global community that includes 18,000 alumni in 90 countries. Darden was established in 1955 at the University of Virginia, a top public university founded by Thomas Jefferson in 1819 in Charlottesville, Virginia.


Press Contact

David Hendrick
Associate Director, Editorial & Media Relations
Darden School of Business
University of Virginia