Thrillable Hours: Scott Jordan, Co-founder Scottevest Travel Clothing

Thrillable Hours - Careers for Lawyers Q&AWelcome back to Thrillable Hours,  my interview series about alternative careers for lawyers

For newer Legal Nomads readers: a little background. I decided to start the Thrillable Hours series as a way to spotlight lawyers and former lawyers who were doing interesting things. On my travels, so many people have asked if I regretted my law degree or years working long hours in New York. I found myself explaining again and again that my legal education served me well, that my time in New York gave me skills I am grateful for. While I feel much more fulfilled and excited about my line of work now, at no point did I regret my prior career. This got me thinking: how did other lawyers feel? Be it those who left the practice of law altogether, or those who opted for something a little less conventional,  I wanted to learn about their stories and how their legal education influenced the way they saw the world.

This new instalment is with Scott Jordan, who co-founded the popular travel technology clothing line Scottevest with his wife Laura. It was my friend Gary (from Everything Everywhere) who put us in touch; Gary works with Scottevest and thought Scott would make a great Thrillable Hours candidate. This word-of-mouth referral has become a great source of new interview subjects, so if anyone has a lawyer in mind for the series, please send them my way!

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What made you decide to follow a less conventional path than typical law school graduates? Was there a particular moment that catalyzed the decision for you?

I did practice law for a while when I graduated from law school. I never fully intended to, but I did really well in law school, and I was offered a great deal of money at large firm. I like to call this the “golden handcuffs” stage. I was always looking for a way to escapt the law, basically. I realized I was miserable…I tried to move away from the strictly legal work by accepting a partnership position at an internet company (thinking I would be more involved in the business side), but I was always considered the “lawyer.” It was a long and winding path, but I finally realized that the best way – maybe the only way – for me to go on as a businessman was to start my own company.

Scott E. Jordan, co-founder of Scottevest
Scott wearing one of his signature pieces.

What do you find most fulfilling about your current job?

I control my own destiny. My income is not limited by the hours that I bill, I am not dealing with clients, so my work is exactly what I want it to be. My dealings with lawyers are as limited as possible. I love the environment at my company – the fast pace, the ideas, the energy, the people – it makes for a totally different experience than I had in law.

Do you have any advice for professionals who are interested in leaving conventional private practice but concerned about what is out there?

If you’re miserable, you owe it to yourself to make the change. When you take the risk, the worst thing that will happen is that you go bankrupt, which in this country isn’t that big of a deal. Being unhappy is always a big deal.

How did your legal education inform the way you see the world today? Do you still identify yourself as a lawyer?

I identify myself very deliberately as an EX-lawyer. My legal education does enable me to understand the legal issues that businesses face. It allows me to filter them and to recognize those that are important. I am not afraid of the legal issues, in short, and a brief history of my company will prove that. Overall, I was good at law but very unhappy – in one sense, this dissatisfaction pushed me to do something totally different, and something that I love. For that I’m grateful.

Scott and his wife Laura, co-founders of Scottevest, Inc.
Scott and his wife Laura who co-founded Scottevest together.

What do you have to say to those who tell me lawyers can’t have fun?

They’re right! From my perspective, I’d agree. The nature of the field – the pressures and the restrictions – does not, in my experience, propagate “fun.”

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Scott E. Jordan is the co-founder and CEO of Scottevest, Inc., a clothing company whose trademark is multi-pocketed clothing especially geared toward the tech crowd.  He practiced real estate and corporate law with Katten Muchin Rosenman LLP and DLA Piper, both based in Chicago, IL. He then left corporate law and served as counsel for a new dot-com, He was commuting between Chicago and New Jersey and had the idea for a vest to serve the modern professional – to hold all the gadgets and gear conveniently.  Shortly thereafter, Jordan founded Scottevest and TEC-Technology Enabled Clothing, and applied for a patent for their Personal Area Network system of wire management. You can find Scottevest’s Facebook page here.


10 thoughts on “Thrillable Hours: Scott Jordan, Co-founder Scottevest Travel Clothing”

  1. I love these series – and they apply to non-lawyers too. I also like Scott’s phrase “golden handcuffs” – well said. Thanks Jodi!

  2. Loyal reader asks, I grew up and live in NY. I’m curious to know what are the grateful skill you acquired living in NY?

    1. Hi John, I meant the skills I acquired whilst working there as a lawyer, not specifically those from NYC. Though I will say that working in NY when I did (as in, right out of law school) gave me a backbone and assertiveness I didn’t have prior….and perfected my already heightened jay-walking skills :)

  3. Great interview! I first heard about Scottevest a couple of years ago so interesting to read his story. I had no idea he used to be one of those evil lawyers! :)

  4. If you haven’t seen it, I highly recommend you watch Scott on The Shark Tank:

    He was awesome! Loved the fact that he turned the tables on all of them!

    Thanks for this, enjoyed the added information on him.


  5. I find that Scott perpetuates a cliche about lawyers that shows that although he was one, he has no real appreciation for what lawyers who ARE hapy with their practices do. The reality is that if you are good at what you do, there can be variety in working with different clients. There can be great satisfaction in helping them solve their problems. There can also be great freedom in crafting your practice, forging your direction and controlling your destiny. Too many dissatisfied lawyers look to others to give them work and show them the way rather than take the bull by the horns and develop their business. Scott likes to distance himself from lawyers because it plays well and is the mantra of the business types and investment bankers. The reality is that Scott wouldn’t have a business if the protections of the law didn’t exist – in that he has a patent, and has used the law to protect his “space” in the market. He has no probelem bringing in the lawyers to protect him when he needs them. He would do well to show a little more respect and gratitude to the good lawyers who have helped him with his business.

  6. A good interview, but his views on bankruptcy are reckless. While Americans are more forgiving about this than European elites (where bien connu business failure makes you a social pariah), declaring bankruptcy is still not not a big deal. Especially if you have children or other dependents, which would probably apply to much of his target audience of 30-ish year olds.

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