Adam Segal is the co-founder and CEO of cove, a D.C.-based startup building a network of neighborhood workspaces. Founded in 2013, cove currently has five locations in the D.C. metro area and one location in Boston. This is the third installment of Segal and cove’s monthly column about startup life in the D.C. metro area.
We all face it — that moment before sleep when your mind races. To-do lists, grocery lists, tasks remembered, tasks forgotten, lofty goals, front door locked?
Just you vs. your thoughts.
These moments provide great insight into our daily lives. Those challenges — that have been lurking in the background — tend to awaken just at that moment when we are looking to sleep.
To better understand these important moments for ourselves, I asked some very busy people in the D.C. tech world a simple, yet telling, question: “What keeps you up at night (metaphorically or literally)?”
Below are unique perspectives from three very different people that run three very different companies. Sure, you may have heard of their companies — including UrbanStems, Storyblocks and Cortex — but chances are, you don’t know what makes these chief executives lose precious REM cycles.
The CEOs I chatted with are collectively responsible for hundreds of employees, investments totaling more than $40 million and countless customers. All this to say there are a lot of potential topics racing through their minds.
For purposes here, we are exploring the individuals and not the companies they run. Interestingly enough, there are some clear themes that emerge around responsibility and accountability, in particular regarding “team.” Like most people, CEOs are constantly weighing priorities, objectives, goals, and pressures; these are accentuated when you include an employee, investor, and customer base that they oversee.
As I read and re-read their responses, I was reminded of how integral the people we surround ourselves with are to everything we aspire to do, both at home and at work — however, all those other worries can get in line behind these people.
TJ Leonard. CEO, Storyblocks
“I would say a couple of related issues are typically the cause of any late night restlessness — time and people. I once heard a definition of optimism that stuck with me: Optimism is not naively believing everything will work out. Being optimistic is believing that with enough time, and the right team, that all problems are fundamentally solvable.
So, when I lie awake and think about the challenges we face, I find myself going back to two basic questions: How do I ensure we have the right team, and one that feels aligned around our shared mission and goals? How do I ensure our time is being spent efficiently on the most impactful problems? If you’re able to answer those two questions, the team will be well positioned for success.
Despite the importance of these questions, I do my best not to lie awake thinking about them. I’ve found that reading before bed helps me separate a bit from the challenges of the day. While I love leadership and business reads, I leave those for Audible during my commute and focus on something that interests me personally at night. Creating that clean separation between church and state has helped me minimize the late night restlessness.”
Bryan Bennett. Cortex, CEO and founder
“I wish I could say that there’s nothing that keeps me up at night, but that would be… misleading. Ultimately, this ties back to a growing level of responsibility that I feel for a team, investor base, and customer base, which are all growing — because ultimately, it’s my responsibility to make sure we deliver for these different groups. What specifically keeps me up at night (metaphorically or literally) changes, but it always ties back to that — doing my best to make sure we’re creating a great environment for the team, creating great returns for our investors, and delivering significant value for our customers.”
Ajay Kori. UrbanStems, CEO and cofounder
“What keeps me up at night is whether we’re doing right by our fantastic team. At a certain point, a CEO’s job is to set a direction, hire people who are better than you at doing almost every function you once did yourself, and make sure they have everything they need to succeed.
[Under Armour founder and UrbanStems investor] Kevin Plank calls these ‘all-stars engines,’ and we’re lucky to have a lot at UrbanStems. What I’m constantly thinking about is whether we’ve sent these engines in the right direction, and we’re giving them the tools to not only succeed but be happy. Happy engines will overcome any obstacle to get to the goal. You just better make sure you’ve set the right goals and destinations.”
Thank you to TJ, Bryan, and Ajay for sharing a window into your lives. Questions or comments? Drop me an email. Also, I would love to hear from others about what keeps you up at night. The more diverse the perspectives the better.