Solo Practitioners’ Perspectives: Sidney Dawsey

Interviewed by: Kenny Matuszewski

Kenny: Where do you work?

Sidney: I work at Dawsey Law, LLC.

Kenny: What do you practice?

Sidney: I practice entertainment law, but also intellectual property, particularly trademarks and copyrights transactional matters. I’m also taking on litigation cases.

Kenny: Why did you decide to start your law firm?

Sidney: Back in law school, I know that wanted to start my own firm or work at a small firm to practice entertainment law, which tends to be handled at small firms. I’m also an entrepreneur, so it always made sense for me to transition from law school to owning my own business.

Kenny: Before you founded your own firm, you practiced bankruptcy law. What inspired you to shift your practice area to intellectual property and entertainment law?

Sidney: I fell into bankruptcy. After passing the bar, I did doc review for a year. Practicing entertainment law was something I wanted to do since college, since I have a background in the music industry, so I knew it was only a matter of time before I went into practicing entertainment and IP law.

Kenny: Did you find it difficult to change practice areas without having worked in that area before founding your firm?

Sidney: It wasn’t difficult for me to change practice area at all. In law school, I got both my JD and LLM in IP law at the same time from UIC John Marshall. While I worked in doc review and bankruptcy, I refreshed my understanding of IP and entertainment law in order to keep motivated and confident in my IP abilities.

Kenny: Did you use any particular resources when starting your own law firm?

Sidney: I read a lot of books! These included Entertainment Law in a Nutshell; The Business of Trademarks, a Practical Guide to Trademark Management for Attorneys and Paralegals, and the Associate’s Guide to the Practice of Copyright Law. I found that I already knew the law. I just needed to get up to speed with the business aspects.

Kenny: Should solos start as generalists, or should they specialize in a certain practice area?

Sidney: It depends on the particular attorney’s background. I knew I wanted to work in entertainment and IP, so I mapped a path to get there. Others didn’t have that same plan before going solo. Generally, if you know what specialty you want to go practice in law school, you should specialize and build that niche. However, for those who don’t know what they want to practice, they should start with practicing any area of law, and then focus on a specialty once they know where they excel.

Kenny: How do you balance your legal work with running a business?

Sidney: Books were a great starting point. Some books I’ve used include The Small Firm Roadmap: A Survival Guide to the Future of Your Law Practice from, and Fireproof: A Five-Step Model to Take Your Law Practice from Unpredictable to Wildly Profitable. In terms of marketing, I received referrals once I announced the opening of my firm. I also learned how to build a website, made sure I had a good firm logo and headshot photo, and learned the importance of SEO. In terms of outreach, I promote my firm on Instagram, the social media platform artists and musicians use most. In order to build my following on Instagram, I make stories and posts. All these efforts lead back to my social media bio, which has a link to my firm’s website.

Kenny: What do you do to generate business?

Sidney: To start, some of the legal work I did helped me get business right away. I have done a lot pro bono work for Lawyers for the Creative Arts (“LCA”) since I graduated law school. One day, a client was unable to qualify for LCA’s services, so LCA referred that client to me. LCA inspired me to finally take the plunge into opening my own firm, so I am very grateful to LCA.

Since then, I’ve built up a client base through referrals from my law school classmates. Many times, I am the only IP attorney they know, so when any of their clients have IP issues, I immediately receive their business.

Kenny: Before law school, you were involved in Chicago’s local music scene. What did you do in that space, and how have those experiences helped your practice now?  

Sidney: I started my music career by playing the trumpet in 5th grade band class. It was something I really enjoyed, so I decided to get more heavily involved in music. In high school and college, I met several different musicians. I was also a producer and DJ and got to know the music industry well. Many of my colleagues were mostly unrepresented and had neither a label nor an attorney. I wanted to help my colleagues in this situation, which is why I decided to go to law school.

It was a happy accident that I got involved in the music industry and found a niche that would allow me to practice an area of law that I law and help people from my previous career.  

While my music career slowed down a bit during law school and my first few years out of school, I started producing music and DJ’ing again during the pandemic. While this was put on pause when my business started up, it’s something I love, and want to keep in my life. It helps keep me sane and is a great stress reliever.

Kenny: What is one thing you wish you knew before you started your own law firm?

Sidney: A positive thing I wish I knew before I started was just how gratifying a solo practice would be, and how rewarding it would be to own my business. I have my own clients, and there is no greater feeling than having the freedom to make a difference and protect someone’s brand, art, or business. I wouldn’t trade the freedom I have now for the world. In fact, if I had known how gratifying it was, I would have started my firm right out of law school.

Kenny: Why should younger attorneys go solo?

Sidney: You should go solo if you are an entrepreneur and have a business owner’s mindset. It gives you the gratification and ability to focus on helping people. More than anything, it is so rewarding to read each and every single thank you note that a client sends you. While it takes some money to get started, you can work on obtaining and saving funds from your other jobs (which I did when I worked in doc review).

Your network is also important. If you build it now, then it’s much easier to go solo right out of school, since you’ll have clients lined up.

Kenny: If there’s one thing attorneys should take away from this article, what would it be?

Sidney: To follow your passion. If you can do what you love, then you should do it. You will be so much happier going down that road.

Sidney Dawsey is an attorney based in Chicago who specializes in entertainment, trademark, copyright, and business law. His focus on these areas of law serves his purpose of representing artists, musicians, athletes, as well as small business owners.

During the last decade, Mr. Dawsey have been heavily involved in the Chicago entertainment and music industries. He built Dawsey Law, LLC to serve creative and innovative clients in order to help them navigate these industries.

While in law school, he immersed himself in both Intellectual Property and Entertainment Law. He earned a Master of Laws in Intellectual Property Law. Additionally, he have gained experience representing clients and their Intellectual Property with respect to the entertainment industry and small businesses through internships and as a solo attorney.

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