Am I a Law Student or an Entrepreneur? I’m Both.

Thoughts after a summer making sense of seemingly incompatible routes.

“Want a slice? Got to roll the dice.” — Nipsey Hussle

Did you ever play the game Battleship as a kid? I did. There was no rhyme or reason when I tried to guess where my friend’s ships were on the other side of the board. But once I guessed right, if D5 was a hit, I’d call out every space around and hope that the 5-space aircraft carrier was going down — not a baby, 2-space destroyer.

This year has been one big game of Battleship. Instead of a friend on the other side, it’s life. More specifically, it’s the challenge of turning an idea into a business.

When something clearly marks a step in the right direction, it seems like a direct hit. That’s great, but that move could’ve maxed out the opportunity. The next move could be completely wrong. To some degree, every life decision involves this type of uncertainty, but by nature entrepreneurship ratchets up uneasiness even in small day-to-day choices. The stakes are higher. You’re constantly betting on yourself.

Something I Didn’t Consider Before

Entrepreneurship first fascinated me three years ago. I was twenty-two, had withdrawn from Columbia Law School with no job or business idea to replace it, and was somehow sitting on a university’s board of trustees. From a 50,000-foot view, for both myself and an institution, I was learning tough lessons about self-awareness and identity. From a practical standpoint, I showed up to my first board meeting as an unemployed and inexperienced kid.

Nevertheless, I was in the room and at the table, a table where entrepreneurs were unmistakably overrepresented. I had no idea why that was the case, but it caught my attention. Now, a little more than three years later, my digital marketing company just had its first profitable month.

I’ll pause this entrepreneurial tale here: my goal will never be to glorify entrepreneurship — or demean those who don’t pursue it. First, the vast majority of what you do as an entrepreneur isn’t glamorous. Second, arguably none of the people who shaped me prior to twenty-two were entrepreneurs, but their guidance nurtured the tools and work ethic I’ll need to be successful in whatever I decide to pursue.

Though I didn’t go to Columbia — and almost gave my mom a heart attack — two years later I enrolled in law school at Georgetown, a ten-minute bike ride from the home my mom (and I) grew up in on Capitol Hill. In my mind, becoming a law student didn’t mean that I couldn’t also become an entrepreneur.

Because I’m in law school, I’m reasonably asked what kind of law I want to practice all the time. I’ve always played along, answering the question, knowing that practicing in a traditional sense isn’t my ideal outcome. On rare occasion, people have asked the right questions that force me to dive deeper and I share my true aspiration of building a business. Until this post, I’ve kept how serious I am about that ambition mostly under wraps.

A Pseudo-maverick?

As I write this, the summer after my first year at Georgetown is winding down. In the first year I didn’t assume any student leadership positions, apply to write on any journals, or participate in the heavily-pushed (and I mean the “we’ve extended the deadline for you to sign up” heavily-pushed) on campus interview process for major law firm internships. All tempting options for different reasons, but all huge distractions from a business that’s showing real promise.

Bucking the system is not what gets you into a place like Georgetown and certainly not what makes you the most employable. Despite being confident in my choices, I’m still somewhat uncomfortable in this new “rebellious” territory. Something that became clear to me three years ago is that playing it safe in your 20’s is probably the worst thing that you can do.

No matter your circumstances, chances are that the older you get, the more responsibility you’ll have — the obstacles to taking chances will only increase. I refuse to wait until I’m wrinkly to take real chances (no offense, seasoned readers). Perhaps this risk-taker sentiment isn’t what you’d expect from a law student; however, this is logical and calculated risk taking in my opinion.

Back in January, I silently decided that Summer 2019 would be dedicated to my entrepreneurial itch. I stopped looking for summer internships then; I never really started. You’ve probably heard law school horror stories. Surviving the first year while also getting a business off the ground is doing the most.

After only one semester, I was mentally exhausted and not making enough progress in business to justify what I was putting myself through. In a way, not looking for a job during the winter and spring took a great deal of stress off of my mental. I told myself that after the summer, I’d have given myself the time and space to figure out if what I was becoming a maverick for was actually worth it.

(Not So) Hot Boy Summer

It pained me to miss my fraternity’s national convention back in July (in Vegas of all places). I’ve had to skip a pool party, dinner meet-ups, and nights out when I definitely wanted to act up with friends. Don’t get me wrong: I’ve still had fun. Instead of being a hot boy, I’ve been pretty tamed and lukewarm this summer.

I didn’t take a job! My coins are almost non-existent! And whatever stress I saved myself earlier in the year not looking for a job has come back full-force knowing that if I don’t keep myself on track entrepreneurship-wise, I’ll be back to square one looking for employment with my increasingly weird resume.

I’ve made it roughly 1,000 words in a post about entrepreneurship without mentioning what in the world I’m actually doing. The details are largely irrelevant to this post — but I promise it’s not a Ponzi scheme. My phone number has been the same since my ringtone was Shoulder Lean, and with the Internet, there are ways to contact me or figure out details if you’re curious.

I will share that with Summer 2019 now almost completely in the rearview, I’m convinced that stepping out on faith has been well worth it. I put in more hours than I would’ve at an internship, but I was able to do so anywhere with an Internet connection, wearing whatever I wanted, and at any time of day. I hired two friends — budding entrepreneurs in their own right — part-time to help me build. And to make it even sweeter yet probably more challenging, my co-founder/girlfriend (boy, could I write another 1,000+ words about that dynamic) and I have decided not to pursue outside funding.

Instead, we’ve chosen to focus on building a business that can sustain itself. When you take other people’s money to start or scale your business (not talking grants or loans), you’re automatically put on a treadmill to sell more equity, buy it back, or take your company public. We have no interest in those options right now.

Not Really a Full-time Entrepreneur (Yet)

So why am I still in law school? Great question. The short answer: it’s complicated. I can’t guarantee that the longer answer will eliminate confusion, either.

First, I would have regrets about not finishing what I started in a way that I don’t about law school round one.

Second, I enjoy learning for learning’s sake. The first book I read this summer was about the fast food industry. Among other things, it mentioned the ramifications of unjust employment contracts for poorly paid workers, the process necessary to create government agencies that regulate business, and how class action lawsuits arise (sounds nerdy and boring, I know). In the first year of law school I learned about these areas in more depth than I would’ve liked to or ever would’ve imagined, not knowing exactly how they’d be relevant outside of class and then boom, there they were popping up in a real-world example when I was trying to learn a little bit more about entrepreneurship and food. The law affects everything.

Third, and related to number two, I’m convinced that the more you’re exposed to, the better decision-maker you become. The hardest decisions don’t force you to choose between a clearly right answer and a clearly wrong one. Often your final options are all reasonable. Law school work is all about comparing and contrasting, which is extremely helpful in difficult situations.

Lastly, I’ll be honest, law school is a hedge (but not the “I have nothing else to do” type). As long as I graduate, someone would probably hire me.

Not finishing at the bottom of any of my classes in year one was a slightly elevated hedge, and staying out of the bottom is a greater motivator to me than breaking my neck to finish at the top (mom, forget you read that).

Finally, a Conclusion

Business is lightyears ahead of where it was pre-summer. Despite having more moving parts — and a team — I’m excited to throw classes back into the mix next week. Transitioning from full-time back to part-time entrepreneurship means leaving money on the table, but I’m playing a long game that’s never been primarily motivated by money anyway.

At my own pace, I’ll keep learning about the warped legal system that steers this country. Given our current climate, you don’t have to go to law school to see how jacked up our system is.

James Baldwin said “to be [black] in this country and to be relatively conscious is to be in a rage almost all the time.” If your eyes are open, even the good always has more than its fair share of bad.

The vast majority of the entrepreneurs on that university board—the initial impetus for this journey—were straight, cis, able-bodied white men. None of the entrepreneurs were people of color. That demographic-makeup isn’t an indictment on specific persons but rather a microcosm of the past and present-day American social and economic imbalance. You could say it became a part of my now not-so-silent rage.

However, being upset is never enough. Action is required. Having entrepreneurship be my avenue for action would be dope! This summer was a taste of that and I loved it. I’m fighting like hell for this summer’s gains not to be fleeting.

But please believe, if my current venture doesn’t pan out and I do need a job, this post might become a little harder to find.

Thanks for reading.