The Starting Line

Today is a very important day for me. First day of Kindergarten type important. The type of important where your mom calls you after to see how it went. The type of…well, you get the point; it’s a big day. Today is the day I launch my first company, Holly Hall Supply Co., a premium line of shaving products, on Kickstarter (shameless plug link here).
Companies start (and fail) every day so I’m well aware of the statistical irrelevance of this day but I’m writing this for me as much as I am for you (how benevolent of me, right?!). Experience, whether through success or failure, tends to erase the memories of how you felt in the beginning. So let’s talk about my journey thus far and some lessons I’ve learned along the way that I hope will be helpful for anyone who considers taking a similar path.
Let’s start at the beginning.
Approximately nine months before my birth, my parents…wait, not that far back. I’m a proud born and raised Houstonian and was lucky enough to attend Strake Jesuit College Prep (what flies dies!), Georgetown University (It’s been so long since last we met…) and the University of Texas School of Law (Hook Em!).
After law school, I joined a big law firm in the corporate section and I felt like I made it. It wasn’t just the money (I can hear the collective calls of “bullshit” raining down from associate offices all over downtown). I found pride in putting on cuff links the morning of each closing even though most closings were virtual and I knew no one would see them. I found confidence in pulling an all nighter and seeing the course through.
Tired moments find me a delightful treat, hours of sorrow, a shrine of understanding.
Oh, and the money was great. But none of that was enough.
I couldn’t shake the fear that if I kept the course, some day I would look back on my life and regret that I never rolled the dice and started my own company.
“I hope you live a life you’re proud of. If you find that you’re not, I hope you have the courage to start all over again.” — F. Scott Fitzgerald
I’m starting over.
I’ve been focused on this day since January when I officially left my firm gig. Granted, I thought this day would be in April, but that brings me to some of the lessons I want to share.
Plan on things taking longer than you expect…but not always for the reasons you expect. I expected R&D delays. I never expected paralysis by analysis; situations where either the complexity or gravity of a situation left me unable to make a decision. Lesson learned is to make a decision and live with it (I usually ended up going with my first mind anyway).
Being a founder is a roller coaster of emotions. A Georgetown alum who is a successful entrepreneur advised me in the beginning to find a co-founder, not only for a complementary skill set, but also to have company in the fox hole. I didn’t understand then but I do now. Since January, I’ve generally had four types of days:
- Days where I wake up and wonder if I made the right decision;
- Days where I am so excited about a development that I can’t get any work done (good problem; problem nonetheless);
- Days where I wake up and feel like the world is mine and today will be the day I prove it; and
- Days where I feel like there’s so much work to be done that I don’t know where to start and don’t want to get out of bed.
I wish I could say that I always answered the call of the bell on #4 days but I didn’t. Lesson learned is that becoming an entrepreneur didn’t make me teflon. I’ll have emotionally draining days. I’ll have great days. I’ll have more that are somewhere in between but, overall, I have to leave room for myself to be human.
There’s endless advice out there; at some point, stop asking for it. I’ve reached out for and received a ton of advice throughout this process. Some of it’s been great and some of it has not (if you gave me advice and you’re reading this, yours was great), but the reality is that the only opinion that matters is the market’s and you have to put yourself out there to get it.
Today is a big day. Today is the day I step into the arena. Talk to you when I get off tonight mom.