Totaling My Car Taught Me the Importance of Showing Up No Matter What
Free Book Preview: Unstoppable
One of my few worldly possessions back in 2009 was an ‘05 Mazda 3. As a 28-year-old trying to get my startup off the ground, I was on the road constantly, driving from one pitch meeting to the next. And like most young founders with little more than a dream, I had to knock on the door of every investor who would listen to me -- sometimes literally. This was also a time when investments in edtech were few and far between, so I had to make every opportunity count.
I was en route to probably the most important meeting of my career -- the kind of do-or-die investor pitch that determines the fate of a nascent company -- when everything changed. I was switching lanes on the highway when, in a sudden moment, I was T-boned by a truck.
My Mazda was wrecked, but, miraculously, I was physically unharmed. Almost immediately, my thoughts returned to the pitch meeting. I knew I didn’t have much time to spare, so I hopped into a cab and was only 15 minutes late. The presentation went about as well as it could have gone, and not long after, I learned that I had won the round. At the time, it felt like just another hectic day, but this moment would come to shape my core understanding of what makes a successful founder or CEO -- the ability to persevere through anything.
The question of "what makes a good CEO" is hard to pin down, and hundreds of articles are written on the topic each year. The answers vary, depending on whom you ask. For some, the key characteristics are curiosity, organization and optimism. For others, it’s the ability to collaborate, while also driving results. And just last year, Harvard Business Review published an entire issue dedicated to executive leadership, citing decisiveness, communication style, proactivity and ability to deliver results as the four most important traits.
The more I think about what makes a good founder or CEO, the less I’m sure about what the actual answer is. Here’s one thing I do know: Most businesses don’t survive very long. As the leader of a company, you need to be able to persist through situations that would cause most people to give up. You need to frequently go beyond what most people would consider reasonable in order to make things happen.
It goes without saying that every day, executives are faced with difficult situations that test their mental fortitude. And, unlike my example, they are usually much less extreme situations. Maybe you’re preparing for an important board meeting, or maybe you’re trying to make a complicated staffing decision. Regardless of the scenario, you need to have grit and resilience to see your vision through.
Years after my accident, I had a conversation with that same group of investors, who told me they were very close to not moving forward with the deal. They told me they weren’t sure about the edtech space, and that they were concerned about my lack of experience as a founder. What ultimately sold them on my startup was me. They figured that if getting into a car accident wouldn’t deter me from making the meeting, then I was the right person to steer a company through a tough market.
I know it might sound a little cliche, but one of my favorite quotes is from a 60 Minutes interview with Elon Musk back in 2012. When Musk was asked about why he entered into the rocket business despite not having an aerospace background, he said, “When something is important enough, you do it even if the odds are not in your favor.”
On that day in 2009, the odds were certainly not in my favor. My business was struggling, and my greatest hope of raising a critical round of funding was in jeopardy. To be perfectly frank, my balance sheet did not look much better than the Mazda. But I knew I had a solid pitch and could not move forward without showing up.
I've found that grit and determination is often forged in misfortune. As a CEO, you need to be many things, and chief among them is the ability to remain resilient. My personal tendency to welcome a challenge and be honest about my circumstances overshadowed any hint of doubt at the time. I'm not sure how I would react if the accident happened today, but I can tell you that I'm a stronger CEO because of everything that happened a decade ago.