Inside the Mind of a Mostly Self-aware, Highly Competitive Introverted Startup CEO
Perched on top of the Deer Valley resort sits the Montage Hotel. After you’ve wound your way up 8,300 feet above sea level, the hotel knocks you breathless. In this particular evening, big flakey chunks of snow were covering everything, except for the sprawling heated driveway of the hotel. Despite the breathtaking view I was full of anxiety. This was the sight of our first executive offsite after the acquisition of our startup Space Monkey, and would be the first time I introduced myself and the vision we had been pursuing for the past few years. The surprising thing is that I wasn’t anxious about how they would react to me or my vision — I was anxious about having to become the outgoing, joke-telling, jovial version of myself that always needed to turn up to these events.
I’m an introvert. You don’t hear that said much of startup CEO’s — it’s assumed that we are so passionate about our company and what we are making, that it would be impossible for us not to wax poetic to whoever will listen. But passion doesn’t always look like that. For me, passion was always easiest and most energizing when I was sitting behind my computer, or working through problems in a notebook. But as a CEO, you become the embodiment of your company or your product, and the crucial piece of getting others excited about what they are making or selling or investing in. As an introverted CEO, I want to share my experiences and how I’ve succeeded in an extroverts world, because I have a sneaking suspicion I’m not the only one.
I don’t remember much about my presentation that night at Deer Valley, and honestly I had practiced it enough that I probably didn’t have a problem with my delivery. But at some point in the meeting our sales leadership presented their aggressive plan for growth (are they ever not aggressive?) and the cornerstone of their plan was to increase the boots on the ground, recruiting several hundred additional sales reps in the next few months.
And that’s when I did exactly what I never wanted to do, something that would be a nightmare for any introvert: I raised my hand and committed my time to help recruit. What was I thinking? Meeting new people is exhausting for this introvert. I’m the worst at small talk. People will often ask me how I’m doing in passing and my response? “Good, Thanks.” And I’m moving on to whatever I’m supposed to do without reciprocating. I feel horrible afterwards because I’m self-aware enough to know I did it, but often the thought of initiating a longer conversation stops me in my tracks.
So there I was committing to talk to total strangers. I spent the next few months helping recruit hundreds of new sales people to our organization. I spoke to large audiences about the Space Monkey founding story, spoke on podcasts and took potential recruits through a tour of the innovation center giving them a glimpse into the future what we were building. Before each engagement I had to go through a priming ritual, a kin to what Tony Robbins does before going on stage, just to get myself out of my comfort zone. Afterwards I would sneak into a dark room and lock myself away for a few hours to recover. It felt like all my energy had been drained and solitude was the only way to refill my cup.
Even though it was difficult, and way outside of my comfort zone, I was glad I did it. Not because it endeared me to the sales leadership, but because it gave me a chance to capture the hearts and minds of the people who would be selling Space Monkey to our customers. It paid off, but it was exhausting.
I recently heard a story about how Ariel Kay, CEO of the modern linen company Parachute, received feedback from investors while trying to fund her startup that she came across as lacking passion; something common for introverts. Not because we aren’t passionate, but because so much of our passion is internal, and used to being on display for the outside world. Kay took the feedback and made some adjustments in her pitch that might not have occurred to many introverts: Sitting up straighter, making purposeful eye contact longer and using explicit verbal cues to exhibit the passion she feels inside for her business.
I related instantly to this story. As some of my younger friends would say, “the struggle is real.” Being an introverted startup CEO can be insanely taxing on your energy and ability to build a high performing company.
People who know me will read this in disbelief; there is no way he’s an introvert! But it’s true.
I have 302 unanswered text messages screaming at me from my iPhone. I’m dreading the idea that I run into someone who is waiting for a response. I prefer a book over a party. Staying home with the family over getting together with a group of friends. Time spent grinding out solutions in a notebook over meetings and brainstorming sessions. In front of my computer over attending a meetup or startup conference.
Being a startup CEO requires the opposite of introversion. You have to get out of the garage (that’s literal for me as I’m writing this in my garage). You have to get in front of investors over and over. It requires lots of small talk, building meaningful relationships quickly, displaying passion, communicating clearly and often and doing it over and over again with new groups of people until you get a “Yes!”.
And once you get a yes, it continues. But this time with new hires, new customers and users of your product over and over again until you find product market fit. All the while being self-aware that you want to be back in the garage, behind your monitor, hacking or whacking your way to success (depending on the metaphor you like).
Luckily I have an insanely competitive nature; it takes over and the pull is stronger than anything else in my life. Let’s put it this way: I hate losing more than I love winning. Just ask my employees when we play pickleball (sorry Bryant) or my wife about my antics at my kids sporting events.
It’s this competitive spirit that drives me to overcome many of my fears and shortcomings in my business life. The will to win can narrow your focus, and it also can make you acutely self-aware when things are not working out or not progressing. Anyone who has played competitive sports understands the importance of failure on the road to progress; you simply cannot succeed without failure and without learning from that failure. Despite my reticence to turn into the most outgoing version of myself over and over, every failure I’ve had along the way has refocused me towards the success of my endeavor, and that success always includes the ability to bring others into my vision. To somehow convince people of the overwhelming passion and confidence I feel inside.
As a competitive person and someone who has failed more times than I care to remember, I have learned there are only three things you can control — and your proclivity to social situations is not one of them. Here’s what I believe we do have the power to control:
- Your effort: How you approach the work and the challenges you face on a daily basis;
- Your output: At the end of the day you have to stop dreaming about success and you have to deliver (don’t be a wantrapreneur);
- Your team contribution: Success hardly happens in isolation, therefore what you contribute to your team will have a direct correlation to your success.
If you are an introvert and you want to start a company (or a new project, or you find yourself thrown into the circles of managing a team), don’t worry because there is hope for you. Plenty of companies and teams have been led by determined introverts. Effort, output, and team contribution are the most important pillars of any hardworking, high-performing individual — and the rest, like when to smile, sit up straight, and start a conversation, can all be learned. One of the most exhilarating experiences I’ve ever had is to take an idea from zero to one; it combines the gravitational pull of being an introvert and the competitive spirit to prove to myself (and others) I have what it takes to launch an idea into reality. You should try it.