Monday, September 19, 2011

Changing Hats: Lawyers Turned Entrepreneurs

           At a meeting in Silicon Valley one day seven years ago, when securities lawyer Ali Wing heard herself criticizing her client’s revenue model, she knew the time had come to change hats.   The daughter of a Montana land investor in a family of nine children, including five adopted siblings, Ali says “we were all raised to conquer the world.” After attending Lewis and Clark College in Portland, she went to work at nearby Nike for eight years, picking up valuable  marketing  skills. Then she left to get an MBA because “I wanted more finance.”  She also thought a professional law degree could help because “I was from a working class family background and wanted every advantage in my pocket.”  At Northwestern she picked up a combined business law degree and in 1997 joined  Silcon Valley  law firm Gunderson Dettmer,  whose clients fund fledgling businesses. When founding partner, now mentor,  Bob Gunderson, first  recruited her, he had told her “I would be happy to have you as a lawyer or a client.”   
Founder CEO Ali Wing
          When Ali first left law for business,  she  became  marketing head  at Gazoontite, a retailer of allergy products, But soon she became  attracted by  the opportunities presented by the growing demographic of older parents. So in 2003 she launched her company, Giggle, in San Francisco, to provide information, organic clothing, equipment, and smarter products for babies,  along with customized services to make it easier when you become new parents.  Now with products and services available both online and in 15 retail outlets around the country, Giggle offers customers personal shoppers, a baby registry, and various gear guides along with, as one recent customer commented, “a very  cool aesthetic which appeals to professional women.”
     Now based in New York, with a corporate staff of 40 and some 120 employees in the field, Ali Wing says “we’re currently in expansion mode building out an executive team.” Results make her point: last year overall sales were up 35%, with catalog and web sales skyrocketing by 70%.   Ali  sees herself as brand CEO  and considers herself “atypically operational.  I’m not a serial entrepreneur, but I do have global domination plans for Giggle. It may take a long time to build big plays, but I have the work ethic and tenacity to prevail,  though I am also quick to delegate when I have the right team.”
     But Ali Wing is just one of a host of former lawyers turned entrepreneurs who value their legal training but were lured by opportunities they couldn’t resist. Jessica Eaves Mathews, based in Albuquerque, found her calling on a golf course. In her 16 years as a successful commercial litigator and business lawyer, she frequently was invited to golf outings with male colleagues. But she was always frustrated with the dress options for women golfers: “I saw that men could wear on the golf course  what they wore to work, maybe a pair of khakis and a nice sports shirt; they  look very put together. But for women the choices were limited to shapeless golf shirts and skorts (short skirts with shorts), inappropriate for business.  I also hated missing out on conversations and dealmaking when I had to change from work dress into those terrible old- fashioned outfits, then change again before I could join the guys for a drink in the club house.” So her company  Grace and Game  was born--  twice! “I first launched the line 13 years ago,” Jessica admits,” but I didn’t know what I was doing because most lawyers are not business people.” Along the way she got some experience running a small  construction company and loved the challenge of building a business.
     In 2008, while she   was playing golf in Hawaii in what she calls another “mini man’s outfit,”  Jessica  decided to relaunch  Grace and Game , to provide chic, luxurious clothing, made of  sustainable fabrics  for women golfers  that they can also wear to work or to dinner as well as on the golf course.  Her clothing, manufactured totally in the US, is available online and soon  in high end golf shops, spas and boutiques in the West.  Jessica believes women are the biggest untapped market in the golf industry,” because so many of them have been put off by the “boxey or  cutesy  look.” Her ultimate goal is to add the non golfing world as target customers by offering her line to major department stores, like Neiman  and Nordstrom.  Her career change wasn’t painful for Jessica because she still uses her legal, analytical skills but she loves being an entrepreneur more.   “Unlike most successful women lawyers, I no longer have to leave 80% of myself at the door to become  successful.”
    As a former  Manhattan assistant district attorney, Chloe Epstein’s conversion to entrepreneurship occurred  when she had children and couldn’t find frozen treats  for her kids  that didn’t contain  “mysterious ingredients.” So she concocted  a  dairy-lactose-, glucose- free product made only with  fruit, filtered water and a touch of cane sugar, instead of fructose or corn syrup. By self financing with two partners, Chloe leased a store on Manhattan’s Upper East Side and bought  soft serve machines  at $20,000 each. Now her company, The Soft Serve Fruit Company, has since opened a flagship store near Union Square  and a pop up store in the Hamptons.  Looking ahead, Chloe hopes to grow nationally, “now that we  know our snack is not just a  mommy-kid product. It appeals to younger guys, especially athletes, and to anyone looking for healthy frozen desserts.”
     Liz Lambert was fighting street crime in Manhattan for a few years before she decided to move home to Texas. While working for the state attorney general, she fell in love with an old wreck of a hotel, the San Jose, in a “changing neighborhood” in  Austin. Once she bought it in 1995, she thought she could “ keep practicing law and renovate the hotel,  but it didn’t work out that way.”  So she left law and became a hotel developer. Today she serves as Chief Creative Officer for her company, Bunkhouse Management  which owns and operates four hotels, throughout Texas, including the now successful Hotel  San Jose, each with its own aesthetic. Though her legal training has been a big help,Liz loves working for herself, and especially exploring  “my creative side.”   One current project.  El Cosmico on 18-acres in Marfa, Texas consists of vintage trailers, safari tents, teepees  and yurts; besides offbeat accommodations, it  also serves as a venue for artistic events.  Does she ever miss New York? “ Sure, I wish I could magically takeownership of the renowned Chelsea Hotel, but maybe instead I’ll settle for doing a well- designed low priced chain someplace in the West.”

If you are a lawyer turned entrepreneur, please tell us your story by clicking on comment!



  1. The quote “Unlike most successful women lawyers, I no longer have to leave 80% of myself at the door to become successful.” really resonated for me. As an experienced in-house lawyer creating a start up in law & strategy, I'm now able to embrace & use my strengths and be myself. Thanks for the great article!

  2. Finally you have made use of all the degrees you have pursued, it seems that you have really worked hard to reach this stage and still you are continuing with that.

  3. This is so inspiring. I am a lawyer myself and I can't believe she managed her work and her business like that. I gotta try this myself.

  4. This is really a nice information that you have shared for us .It's really great work of yours.I truly appreciate it.

  5. What a great article. I know first-hand the Jessica Eaves Mathews provides sound legal advice and I’m so excited about the Grace & Game Golf line — this will revolutionize golf wear for women and it’s long overdue. To get more info please visit