From Lawyer to Fashion Entrepreneur

bridgette hyltonIn this installment of the 0.1 Billable Hour Interview, we talk with Bridgette L. Hylton.  Bridgette, an ’09 law school graduate, is a former corporate associate who left law to cofound fashion tech startup with her Harvard Law School classmate Joana Florez.  ShopRagHouse is the place where Project Runway meets Kickstarter. Everyday fashion enthusiasts and designers can submit their design ideas for a chance to have them produced and sold for a share of the profits.  Let’s get to the questions!

1. Why did you leave law?

The short answer is that I left law because I wasn’t passionate about it. It was a hard choice to make since I was learning so much at my firm, the pay was good, I loved being a part of the hustle and bustle in New York City, and I really admired the partner that I worked with. She was and is a powerhouse, but I could tell that we were different. While the creative structuring of deals was something that really drove her, it didn’t drive me. Doing my job, even doing well at my job, didn’t bring me joy. That should have been a big red flag.

Then there was a question of fit. I started to feel like I didn’t fit in pretty early on. I strolled into the office in sky high red stiletto Stuart Weitzman pumps only to have my secretary tell me that I should try to tone down my fashion choices. At some point you have to be honest with yourself about fit or you will never be happy. It wasn’t until a few months later that I realized my dream of becoming a Prada suit wearing M&A partner, wasn’t my dream any more.

After leaving practice, I almost immediately fell back into the things I had cared about in law school and still care about now, politics and startups.  I spent some time exploring what my next move would be and in the meantime became a mother. I knew after having my child that I wanted a career that would allow me the flexibility to be hands on with my son, but would also still challenge me. The idea for ShopRagHouse was born while I was doing some major soul searching about what I wanted to do next – a rough and tumble time where my career dreams swerved between politics, writing, and fashion (I even tried to launch my own dress line!). When my business partner called me with the idea for ShopRagHouse, something just clicked. It fit. I could use my legal education and still wear red stilettos?! Sign me up! We’ve been full steam ahead on trying to launch our startup since then.

2. What was the hardest part of your career change?

One big change is not having the internal structure that lets you know if you are doing a good job or the right thing. At a firm if you do well, you keep your job and if you do really well, you get praised for it; if you do poorly, ultimately, you probably don’t get to keep your job. It’s pretty straightforward. In the startup world, there is no easy validation and when you are your own boss, there isn’t always someone there to pat you on your shoulder and say, “good work, Hylton.” We rely a lot more on intuition now than we do on praise: Does it seem like our idea is building traction? Do people seem excited to talk about ShopRagHouse? The answers to those questions have to motivate us on a daily basis to keep plugging. Luckily we’ve had some great feedback so far and the buzz continues to grow so we are optimistic.

Adjusting to being more flexible about deadlines and timelines was another big change for both of us. We have to remind each other that we don’t have to freak out if we don’t get a pattern back on time every single time, but I’m grateful that we both know how to push things forward when we need to – chalk that up to our legal educations!

3. What advice do you have for other lawyers who are thinking of changing careers?

Be brave! Be confident! A lot of people look at me like I’m crazy when I tell them I left big law to start a startup – especially so because we’re still just getting off the ground. If I weren’t confident that this was the best decision for me and that this business can and will succeed, I might have run back to a law firm begging for forgiveness. I haven’t yet and I look forward to ShopRagHouse being a huge success soon so that I can prove that following your joy to the ends of the earth is 100% worth it.

Readers, have you thought about starting your own business?  Are you doing it now?  Why or why not?

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One response to “From Lawyer to Fashion Entrepreneur

  1. I got rid of law jobs. This is a nice idea and fantastic post. Neer knew this, regards for letting me know.