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Orlando Sheppard: “5 Things I Wish Someone Told Me When I First Became an Attorney”

Be patient — In the legal field, it is easy to get caught up in comparing yourself to the next person. It may be your friend from law school who got the big law job with a big salary or the partner of a firm with a fancy car. However, your time will come. I […]

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Be patient — In the legal field, it is easy to get caught up in comparing yourself to the next person. It may be your friend from law school who got the big law job with a big salary or the partner of a firm with a fancy car. However, your time will come. I have friends who have started out with unpaid positions and gone on to become general counsel of organizations. Sometimes a sacrifice is necessary to get to the position you want to be.


I had the pleasure of interviewing Orlando Sheppard. With a knack for success and a tenacity for garnering results, he aims to level the playing field for the “little guy.” As a co-founder of Purely Legal, a law firm founded to provide competent legal services to Florida, Maryland and Washington, Orlando strives to stand with his clients and provide competent representation in all of their legal matters. Born and raised in Panama City, Florida, he relocated to the city of Orlando in 2008. He graduated from the University of Central Florida in 2012 with a Bachelor of Science in Psychology. Upon completing his undergraduate degree, Orlando enrolled at Florida A&M University College of Law and graduated with cum laude honors. He was later admitted to practice law in Florida in September 2015 and in Maryland in 2018.

It was in law school that Orlando found his passion. While working at a prominent personal injury firm in Central Florida, he saw firsthand the negative impact an accident could have on a person’s life. More importantly, he saw how a person’s life can be changed for the better when they have compassionate yet diligent representation in their corner. Since that experience, Orlando has vowed to deliver the same type of representation to his clients. He continues his focus in personal injury, representing his clients including automobile accidents, slip and trip and falls, dog bites, and wrongful death.

In addition to his professional endeavors, Orlando is active in the community. He is a board member with Life Beyond Adversity, a nonprofit with a mission to help urban youth facing socio-economic hardships further their education at institutions of higher learning and equip them with the ability to make better life decisions. Additionally, Orlando is an active member of Alpha Phi Alpha Fraternity, Inc. and currently serves in the Paul C. Perkins Bar Association in two roles as General Counsel and the Chair of the Law Student Mentorship Committee.


Thank you for joining us Orlando. Our readers would love to get to know you a bit more. What is the “backstory” that brought you to this particular career path in Law?

Ispent the majority of my life in Panama City, Florida before relocating to Orlando to attend the University of Central Florida.

I wish I could say I’ve always had dreams of becoming a lawyer. There’s no lawyer in my family that I looked up to. I don’t even think I knew a lawyer before attending law school. I applied to law school as a backup plan. I was a psychology major in undergrad because I enjoyed understanding people’s behaviors. But when it was time to graduate, I had no idea what I wanted to do with my life. A Juris doctorate provided me with more opportunities and time to figure things out. I still didn’t even want to practice law. However, in law school, a couple of experiences changed my direction. During an externship for a judge in Orlando, I saw firsthand how many people are taken advantage of because they can’t afford an attorney — taking bad settlements or in court alone, while a bank or major company sends a different attorney to each hearing. Second, I noticed the legal profession lacked people that look like me. According to the American Bar Association, African American attorneys made up 5% of the attorney population in 2017. That number hasn’t changed since 2009. I’ve been on a mission ever since to even the odds for both the unrepresented client and the underrepresented Black attorney.

I found my passion for personal injury through trial and error. I tried many areas of law, including landlord-tenant law and family law, before hitting my stride in personal injury.

Can you share the funniest or most interesting story that occurred to you in the course of your law career?

Early in my career, I had a hearing in a neighboring county and was running a little late. However, if everything went perfect, I would have made it just in time. Of course, things didn’t go perfect. I was pulled over when I was about 20 minutes away from the courthouse. Being a young attorney, I was panicking. I called the judicial assistant and explained what happened. Once I arrived and walked into the judge’s hearing room, the judge made a joke about it and everyone laughed. I definitely learned a lesson about being timely that day. The plus side is that I won the hearing.

What are some of the most interesting or exciting projects you are working on now?

Most recently, I have committed to doing giveaways on social media to make the path to becoming a lawyer just a little bit easier. 2020 has been a unique year and it’s tough for a lot of people. So, I am attempting to make things easier. In May, I covered the LSAT test fees for two aspiring lawyers. In June, I will be providing one $200 gift card each to two winners and may do some small giveaways throughout the month. I will also be doing giveaways in July and August (the prizes have yet to be decided). I did the giveaways through my personal Instagram page (@OrlandoTheEsquire) to be more approachable and accessible to the aspiring lawyers. Instagram is a lot less formal and will hopefully make the students more likely to reach out.

What are some of the most interesting cases you have been involved in? Without sharing anything confidential can you share any stories?

Wow, where do I start? Confidentiality makes it tough to discuss, but there’s rarely a dull day with my personal injury cases. Honestly, when reading cases in law school, you may say to yourself, “there’s no way this stuff really happens” — and then you get that phone call from a client. A lot of people have heard about the infamous McDonald’s case involving the hot coffee. I have had a similar case. I also go toe-to-toe daily with lawyers representing Fortune 500 companies. It’s unfortunate and frustrating — people have genuine injuries, and on the other side, you have an insurance company basically telling your client that their injuries are worth pennies.

Which people in history inspire you the most? Why?

The rapper Nipsey Hussle is still a huge inspiration to me. Despite his untimely death, I have always loved an underdog’s story and juxtaposition. As a gang member from South Central Los Angeles, Nipsey Hussle wasn’t supposed to accomplish the things. But he took the things he learned and filled his music with lessons of encouragement, community investments, and ownership — earning him a Grammy award nomination and winning a Grammy posthumously along the way. He is a constant reminder that almost anything is possible.

What advice would you give to a young person considering a career in law?

The first thing I tell young people considering a career in law is to have an idea why you want to become a lawyer. It’s not like it seems on TV. The work can be mundane, and a lot of people become jaded because it’s not what they envisioned growing up. Try to see what a lawyer does firsthand. Shadowing and internships are a great way to see firsthand. Second, I would say find a mentor.

If you had the ability to make three reforms in our judicial/legal system, which three would you start with? Why?

1. The profession needs more diversity. Large firms often tout diversity as one of their focuses but are hesitant to expand their reach beyond the T14 law schools or put diverse individuals in positions where they could effectuate real change on firm makeup.

2. The ethics rules governing lawyers are outdated. While it’s understandable to hold lawyers to a high standard to protect the consumer, at the end of the day, a law firm is still a business. The current ethics rules create unnecessary barriers to law firms that don’t exist for a lot of businesses. For example, in many jurisdictions, a law firm is not allowed to use a trade name forcing lawyers to use the last names of partners as the name of their firms.

3. Law schools need reform. The critical thinking that one hopes is developed in law school and required courses can be taught in the first two years. The third year should be dedicated to practical learning and/or apprenticeships to ensure lawyers are ready to represent people effectively.

How have you used your success to bring goodness to the world?

Aside from the representation I offer to my clients, I say my major contribution to the world is providing opportunities to the future lawyers coming behind me. As I stated, I didn’t know a lawyer before law school. So, I wasn’t always sure how to navigate the spaces I was in. There can be a lot of barriers in getting into the legal field, from obtaining that first internship to passing the bar. So, I wanted to be a bridge instead. As part owner of my firm, I am able to offer internships directly to law students in my area, who otherwise might not have had one. Hopefully, they’re able to get some good experience for their resume and continue on to their dream role. Additionally, I previously served as the law student mentorship committee chair for the Paul C. Perkins Bar Association, a local voluntary bar association in Florida. I helped revive a lawyer-law student mentorship program wherein law students were paired with an attorney counterpart for the year. The pairs were encouraged to meet, communicate, and attend events together so that the law students would have someone to lean on as they navigate law school.

I know this is not an easy job. What drives you?

Two things drive me. I’m motivated by creating opportunities for other people. I desire to build something with a lasting impact. I also have a desire to build a national or international firm that lasts for hundreds of years. Second, I like the gamesmanship of practice. Similar to what people saw of Michael Jordan in The Last Dance documentary, I love the competition. Strategizing and planning the next move to accomplish the best result for my client is exciting and I have fun doing it. When I stop having fun, then I’ll stop practicing and step full time into the “CEO” type role.

What are your “5 things I wish someone told me when I first started” and why. Please share a story or an example for each.

  1. Be patient — In the legal field, it is easy to get caught up in comparing yourself to the next person. It may be your friend from law school who got the big law job with a big salary or the partner of a firm with a fancy car. However, your time will come. I have friends who have started out with unpaid positions and gone on to become general counsel of organizations. Sometimes a sacrifice is necessary to get to the position you want to be.
  2. Ask for help — In my experience, experienced lawyers are often willing to share their battle stories and offer guidance to budding lawyers. I’ve called and emailed complete strangers when I couldn’t find an answer to a question through my own research.
  3. Owning your own firm is possible — Leaving a job working for someone else and jumping out as a partner to start a firm was one of the scariest things. I considered opening my own firm many times before I actually did. Many lawyers frown at the idea of opening a firm right out of law school. However, when you receive (often unsolicited) advice about hanging your own shingle, be sure to ask if the person has actually tried doing so.
  4. Learn one practice area well — To clarify, my advice is different than finding a niche. A niche can be a successful way to build a business by focusing on a particular area of law and honing those skills over your career. My advice is more so to develop a safety net with one practice area. Take the time to develop a knowledge base that you can use throughout your career. By all means, try some other areas of law and find out what you like. For example, although I now practice personal injury, prior to this I was well versed in landlord-tenant law. So, when I made the shift to personal injury, I always knew in the back of my mind if personal injury doesn’t work out, I can always shift back to personal injury law.
  5. Don’t be afraid to negotiate your salary/benefits — A law firm is a business like any other. Salary may not always be negotiable, but it doesn’t hurt to try. Smaller firms are not always in a position to offer more money in terms of salary, but perhaps they can offer other benefits. Some things you may be able to negotiate for include CLEs, bar dues, and bar association membership fees.

This was very inspiring. Thank you so much for joining us!

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