My Entrepreneurial Journey: The Origin of Diplomatic Enterprises
Clinton W Mitchell, Esq.
September 24, 2024
The unexpected road that took me from law school graduate to Founder and CEO
A portrait of Clinton Mitchell, Founder and CEO of Diplomatic Enterprises

Recently, we launched a refresh of the Diplomatic Enterprises (DE) website with the extremely talented Anna Mulamba at the helm. She’s a program friend who led our digital transformation in 2020 and manages the monthly “tech stuff” for Team Diplomat. While discussing what changes we would make this go-round, we began discussing how DE came to be, which, unbeknownst to me, we hadn’t discussed in depth before.

After sharing the story with her, she encouraged me to share it on the site for everyone to see. I politely yet quickly declined with a nervous chuckle. She insisted and gave me all the business reasons why it would make sense, but there was one very practical reason that landed me: it’s my company, and we need to make the connection between DE and CM. (me, Clinton Mitchell). She was right. So, gather around, ladies and gentlemen (or however you self-identify). It’s story time.

DE was officially launched with the Maryland Secretary of State on April 9, 2013. But the story of how this company came to be began during the summer of 2009. I had just turned twenty-five, graduated from law school, and was preparing to study for the Illinois bar ahead of my new job at the Cook County State’s Attorney’s Office. If that wasn’t enough, in and around this time, I called off the engagement to my longtime girlfriend, which obviously was not great in terms of timing. I spent the first couple of weeks alone in an apartment we shared, contemplating the meaning of life and reenacting every ’90s R&B video. If it weren’t for the help of some really great friends (Piper, Danielle, and Marcus), I’m not sure I’d be where I am today.

Piper and I met during law school and were a year apart in classes. We took a couple of courses together and even interned together at the DC Sports & Entertainment Commission (currently known as Events DC). I checked on her regularly during her bar prep summer, and when it was my turn in the barrel, she returned the favor. During one of these routine checkups, I told her what had happened and how I had resigned myself to failing the bar that summer because I had a late start and didn’t think I could recover. She said, in so many words, “Absolutely the f&*$ not.” That conversation created a spark that led to a flame fueled by my friend Danielle.

While Danielle wasn’t an actual graduate of Howard University School of Law, you wouldn’t know by the amount of time she spent on our campus. To clarify, she attended law school; she just wasn’t enrolled at mine. We met through a mutual friend, and we’ve been cool ever since. When she learned that I was down bad, she thought some fresh air and change of scenery would do me some good. Studying for the bar herself, she pushed us to study together regularly in places across DC and Maryland. Being forced to get up, get out, and interact with the world was extremely helpful. When it came time to pack all of my things and make the 12-hour drive over the river and through the woods to Chicago, I was at a loss. It was a trip I had originally planned to take with my former fiancée. *insert R&B tears*

Enter one of my childhood best friends, Marcus. He flew to DC to help me pack, load, and drive a minivan stuffed to the brim. Theoretically, I could have made the drive by myself. But, in actuality, I couldn’t have done it without him. I couldn’t have done any of that summer without those three. My survival was intricately tied to what happened next.

In August 2009, I moved to Chicago to start my legal career. As a new hire, I was assigned to 1 of 3 tier one assignments: Child Support Enforcement. If you want to see America, there are three places you can go: a football game, Popeyes, and family court. The greatest cross-section of America lies in those places. But I digress. On my first day in the office, I was handed my onboarding materials, shown my office, and then escorted across the street to the courthouse to start “trying cases.” It would be weeks before I knew whether I had passed the bar, and months before I’d be sworn in. And let me tell you — they had me doing the work of the people before I even knew where the restroom was.

I grew to love the office, from the court assistants who helped me learn to lawyer to the sheriff’s deputies who kept us safe; the administrative staff who helped me navigate life, the city, and office politics; and my fellow Assistant State’s Attorneys (ASA) who did their best to help me forget about everything that ailed me outside those doors. My stint was short, but the love I have for that place and those people is long.

In the spring of 2010, my mother informed me that my grandmother (“granny”) wasn’t doing well and that she had what the doctors believed to be a brief time to live. My immediate response was that I would move home and help out. I’ll be completely honest; I have no idea why I said that. To this day, I think about that conversation and decision and ask myself, “What the hell were you thinking?” To be clear, I have zero regrets. The eight months I got to spend with my granny before she passed were extremely difficult. But had I stayed in Chicago, a thousand miles away and on a modest salary (my teacher’s salary and ASA salary were nearly identical), who knows how much time I would have been able to spend with her before she passed.

During the two years I spent back home in Miami, I served as the Director of the Center for Legal and Public Affairs magnet program at my alma mater, Miami Carol City Senior High. There, I taught classes in law and public affairs and led the program in a place that had my own former teachers still roaming the halls. Navigating that was an even greater challenge than being a prosecutor. As a prosecutor, there are statutes and case law to guide you.

When I started at Miami Carol City, there was a classroom, books, and some loose guidelines on how to operate within the lines. But, as a first-year educator, there was nothing that could have fully prepared me for being inside a classroom. So, over the course of a few weeks, before the start of classes, I built lesson plans, cleaned, organized the classroom, and created a strategy to lead the program. And when the students arrived, a great deal of that changed. There were fights (between the students, not with me), lockdowns, pregnancy scares, and deaths in the community (including Trayvon Martin, who was a former student at the school). To make matters more difficult, I also taught English at night school because they were short-staffed and I knew the night school principal from my time as a student. So, when he made the ask, I said yes. Add to that the fact that I moonlighted as counsel for a sports marketing firm. And when I wasn’t doing all of that, I was helping my mom take care of my granny.

At the end of those two years, I bid adieu to Miami and moved back to DC. My search for career opportunities that would allow me to pursue my varied interests proved unfruitful. It was the lowest I had ever been in my life, including the summer of 2009. Apparently, my time in Miami was seen as a departure from my legal career rather than an extension of it. My resume didn’t offer enough space or opportunity to explain why my stint in Chicago was so short or why I left the second largest prosecutor’s office in the country to *checks notes* teach at a high school. In between job applications and interviews, I did document review work to make ends meet. It wasn’t much, but it paid the bills. After applying to over a hundred jobs and growing tired of being told that I was either “overqualified,” “underqualified,” or a flat-out “no,” I launched Diplomatic Enterprises LLC.

The short origin story that I usually give in place of this one is that I got tired of being told no and wanted to create a place where I could bring my diverse talents, skills, and expertise to bear in the market. I’ve worked on Capitol Hill and at the Pentagon, Burger King, and the local hardware store. I’ve worked on political campaigns and branding projects and built corporate giving offices from the ground up. I’ve collaborated with athletes, entertainers, creatives, entrepreneurs, and anyone with a dollar and a dream. Over the course of eleven years, I’ve grown and developed the company I wanted, doing projects I want to do. It hasn’t all been glamorous, and my success has been anything but linear. Nevertheless, I persisted. Over time, with the help of a team of skilled experts, we’ve negotiated “Shark Tank” deals, brokered television production agreements, and protected brands’ intellectual property among many other things.

You will not find a person or a team who will work as hard as DE to deliver for you and your business. That’s because we understand what it’s like to build something from the ground up in the face of adversity. Our job is to cultivate relationships, devise strategies, and help athletes, creatives, entrepreneurs, and small businesses become the best version of themselves.

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