The Fear of Failure (Life in the Legal Tech Startup Trenches)
You’re in bed in a cold sweat. You’ve been tossing and turning for hours. It’s 4:15am and you reason that if you fall asleep right now, at least you’ll get a few hours of quality shut-eye. But you know it’s in vain. It hasn’t happened for months; why is tonight any different?
You’ve slogged for years with your team, navigating the waters of incorporation, team building, engineering and business development. You’re trying to build a company based-off an idea in the legal space.
You’ve spent years studying in law school and several more learning the profession as a lawyer. You had money in your account and a steady paycheck. You had respect from your peers, your family and other professionals. You had a beautiful office in a gorgeous tower overlooking the city. You had certainty and predictability. You had access to the good life.
You had what so many have sought after and you said “No thank you.”
And now here you are, looking up at the ceiling, questioning your choices, wondering if your decisions were ill-fated because they were based on hubris. Your bank account is near empty, you live on a shoestring budget. You’ve cashed out your savings and every day is one step closer to admitting defeat.
And every now and again you get a friendly “don’t worry” from your colleagues, reminding you that “you can always go back to being a lawyer.”
You are genuinely afraid of failure.
I am often asked what it’s like being an entrepreneur in the legal space. What is it like building a technology service company that offers services to law firms all over the world?
My response is the same. It’s lonely. Or at least it was, for a long time.
A few years ago, I was asked to speak at a panel at the Law Faculty of Queens University, presenting to the students of the Venture Capital and Private Equity law club. Seated next to me were two lawyers both practising in the startup and emerging company departments of their large (and very successful) national firms.
The lawyers eloquently described their roles in the legal side of fundraising, how they were instrumental in providing advice in helping secure VC investment for their startup clients, thereby helping those companies grow.
The role of my lawyer colleagues was instrumental in helping their clients succeed.
I wanted to impart a somewhat different perspective on the students. I wanted them to understand what investment money means to a startup, especially in the legal space. Investment means my team gets to eat, pay their mortgage and pay for their childrens’ dentist appointments. It means Christmas gifts under the tree and a few restaurant dinners a month. It doesn’t just mean business survival, but actual human survival.
Most of the legal tech startup life is unglamorous. You are in a sector that has resisted change for generations. Everything is working against you, from the billable hour model to the partnership structure of law firms to the lack of funding opportunities available to those in your industry.
You are trying to find your professional place in the world and you don’t always know where you fit. It’s daunting. It’s draining. Reaching the legal technology apex often seems insurmountable. The sides of the mountain are just too slippery.
Years later, you’re still in bed, still sweating and wide awake when you should have been long asleep. The sheets, half on, half off provide no comfort, as the birds chirp outside your window welcoming the coming dawn. You start counting on your fingers and toes and quickly realize you’ve spent more time building legal technology than actually practicing law. Even if you wanted to return as a lawyer, would you remember how to practice? Would anybody even want you?
And then, out of nowhere, you crack a wry smile. You look back on everything you have done up to this point. You’ve built amazing technology. You have clients who pay for your service. You have gained experience in tech, business and life. And you even begrudgingly admit to yourself that if someone would have told you that after several years you’d be in such a position, you would have gladly accepted the opportunity with open arms.
Fully awake, looking up at the beige plastered ceiling, you accept that you’re exactly where you belong.
You then get up and start your work day.