From Finance to Creative Entrepreneur

Chris Latham

Finance may not seem like the logical starting point for creative entrepreneurs. But success stories like Josie Natori and Michael Lewis prove otherwise. Key to success are confidence and the willingness to challenge conventional thinking within a new arena.

A person holding a lightbulb that is illuminated.

Ask most people what kind of career a financial job will lead to, and they probably would not start discussing artistic pursuits. Yet quite a few entrepreneurs who began their careers at banks and brokerages later found great success by venturing into unexpected territory.

“This Is Capitalism” has showcased the captivating style of Josie Natori, a former Merrill Lynch investment banker who launched The Natori Company and gave the world an elegant line of women’s clothing that pays homage to the Asian aesthetic. Citigroup also can count a handful of former bankers who left to launch online clothing companies.

Outside of high fashion, the media industry has also proven highly rewarding. Here are three such mavericks who managed to combine their financial know-how with their creative interests. They serve as excellent examples of how to be an entrepreneur.


After five years at UBS, Geoff Bartakovics departed his business strategist role at the global bank as the market downturn spiraled into the onset of the financial crisis. In July of 2008, he began managing TDT Media Inc., doing business as Tasting Table, a digital brand for influential foodies. Writing about recipes and hosting catered events is as far as one could get from analyzing fixed income and mortgages, so how did it happen?

Bartakovics was able to make the most of his personal network, and pitch venture capital company the Pilot Group on something that on the surface seems unrelated to either finance or food: a software platform to handle emails for websites and newsletters. The venture capital firm asked Bartakovics to implement that tech for a new culinary project that he could oversee. Soon, was born and Bartakovics was at the helm. publishes articles and videos on recipes, restaurants, travel locations known for specific types of cuisine, tips for hosting events, and spotlights of celebrity chefs. It also hosts contests like the “Lobster Rumble.” Tasting Table has been reported as having 2 million newsletter subscribers and producing revenues of $12 million.


After gaining his Bachelor of Science in Finance from Rutgers University, Gregg Spiridellis joined Goldman Sachs as an analyst. He stayed there for two years before moving on to Bear Stearns for another two years. He then went to Wharton business school for his MBA.

That trajectory might appear to point toward another few decades on Wall Street. Instead, while at Wharton, he got the idea to use multimedia software for low-cost digital filmmaking. Spiridellis and his brother Evan, who was already an artist and independent filmmaker, launched JibJab Bros. Studios in 1999 with an initial investment of $10,000.

Due to the technology on hand at the time, the online company began by transmitting humorous animated videos through telephone lines. The brothers had early success producing animation for Sony and Disney, and branched into physical toys and children’s books. Other payment streams included charging customers to download videos, selling DVDs, and a Netflix show called “Ask The Storybots.”

Los Angeles-based JibJab grew to employ 70 staffers, contract with hundreds of artists, and generate annual revenues in excess of $20 million. By pursuing his passion of funny films, it’s no stretch to say that Gregg Spiridellis has been laughing all the way from the bank.


No account of someone who’s successfully gone from high finance to creative entrepreneurship would be complete without mentioning the one-man brand that is Michael Lewis. His educational background hinted at the switch. Lewis attained an undergraduate degree in art history from Princeton and worked for a prominent art dealer before earning a graduate degree from the London School of Economics.

That led him to become a bond salesman at the renowned investment bank Salomon Brothers (long before it became part of Citigroup). Lewis stayed at Salomon Brothers a few years, but ultimately resigned to write a book about his observations of the firm and Wall Street in general during the late 1980s. “Liar’s Poker” became a literary sensation. Since then, Lewis has written several best-selling non-fiction books on subjects ranging from finance to sports that, all told, have sold nearly 10 million copies.

Three of his books — “MoneyBall,” “The Blind Side,” and “The Big Short” — were adapted into major films with A-list actors that together grossed over $550 million at the box office. Sandra Bullock won a 2010 Academy Award for Best Actress starring in “The Blind Side” and “The Big Short” won a 2016 Academy Award for Best Adapted Screenplay.


Aside from early jobs in finance, what do these entrepreneurs have in common? Confidence that they could thrive in a new arena of their own choosing, and willingness to challenge conventional thinking within that space.

Josie Natori not only took inspiration from patterns flourishing in her native Philippines, but also cultivated a production team there by hiring locals to work at her global fashion company. Geoff Bartakovics went beyond the traditional format of pre-internet food magazines to target white collar professionals who spend their days focused on their email inboxes. Gregg Spiridellis saw that young people were a natural audience for expanding online entertainment into real-world merchandise. And Michael Lewis figured out that financial journalism could fuel Hollywood blockbusters.

While it was far from obvious at the onset how each of them would make the leap, their ingenious decisions make perfect sense when looking back at their paths.