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What Does It Mean to Be Entrepreneurial?


When Rana DiOrio graduated from Vanderbilt Law School in 1991, she joined the corporate securities team at a large San Francisco firm. A former pre-med major, she “fell into” transactional law while working as a summer associate. “I liked building something versus litigation, which I saw as throwing spears,” she recalls.

Later, she “rode the dot com tsunami” while handling software transactions at Silicon Valley’s storied Wilson Sonsini, where she billed 3,000 hours a year. “I was working so hard that twice I accidentally showed up in a suit on Saturday.”

In that job, she worked closely with an Alex Brown & Sons investment banking team that eventually recruited her away from law. She later joined Merrill Lynch and then Banc of America Securities.

Right around the time DiOrio started a family, the economy’s “bubble blew up” and she spent a few years investing in real estate. In 2005, she needed to return to the workforce for a more steady income and joined a mergers and acquisitions boutique.

But all that time, she’d also been writing children’s books for fun. When she showed her manuscripts to friends, DiOrio earned rave reviews. With titles like What Does It Mean to Be Present?, What Does It Mean to Be Global?, and What Does It Mean to Be Safe?, she also heard feedback that there was “nothing in the marketplace” like her books.

Knowing that no traditional publisher would agree to her insistence on soy ink, recycled paper, and eliminating wasteful dust jackets, DiOrio chose instead to launch her own publishing company. “I’d worked with entrepreneurs my entire career; it ignited my own entrepreneurial flame.”

In 2009, Little Pickle Press was born. “I wanted to be true to my values and bring publishing into the twenty-first century,” which included having environmentally friendly and socially responsible practices. Today, she runs a virtual office and hires primarily independent contractors.

DiOrio says she uses her legal training every day at Little Pickle Press, particularly in pitching ideas and negotiating. “Lawyers are trained to critically analyze and to listen so they can extract detail and nuance, and both are extraordinarily valuable in problem solving,” she says. “Lawyers are also good writers—crisp, clear, and compelling. That serves you well in any profession, but especially in business.”

DiOrio is so passionate about the versatility of a law degree that she funds a scholarship at her alma mater for a third-year student who plans to use a JD for something other than billing hours at a traditional firm.


Leslie A. Gordon is a secret lawyer who has been working as a freelance legal affairs journalist for more than 10 years.

Vol. 41 No. 4

Leslie A. Gordon Freelance legal affairs journalist and corporate writer/editor for law firms and other professional service firms. Former staff writer at The Daily Journal, a legal affairs newspaper in San Francisco. A "recovering" lawyer, also spent five years as an adjunct professor teaching writing at UC Hastings College of the Law. Author of the novels HEADS OR TAILS and CHEER.

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