1. What have you found most challenging as a leader of a small or medium enterprise?

Knowing what the "right" answer is when it comes to acting in the best interest of my number one constituency: my employees. There are often decisions and actions that can seem right in the near term, but that are far more negative effects down the line. In a similar vein, there can be decisions and actions that seem painful in the present, but that actually are to the benefit of the team and the team members longer term. Balancing this is incredibly difficult.

2. How did you become a leader of an SME? Can you please briefly tell the story?

On a family vacation in 2012 I heard two family friends complaining about how the vacation rental industry worked. After asking a bunch of questions I asked: "why don't people just do it this other way?" The family friends looked at me like I was an idiot and said: "Sure. If there was a way to do that, EVERYONE would do that." I was hooked. I spent the next 10 months researching and building out my idea for the business that would solve the need, eventually quitting my job and spending the next ~10 years working to fill the gap I identified in that initial conversation.

3. How do you structure your work days from waking up to going to sleep?

This changes a little by quarter as I reassess my priorities and where I want to "budget" my time in the coming quarter. At a high level the morning is spent on self-reflection, health, and creative work (like writing). Late morning to early afternoon is spent in direct interaction with my team members (1:1s and other meetings) and our clients. Late afternoon and into the evening is spent on focused work where I do my best to not be interrupted. This last part is split into two, as I take a break to have dinner with my family, and read to my daughter before bed. Then I go back for the second portion of this last part of the work day. Finally, I read in bed for about 30 minutes before turning off the light and going to sleep.

4. What's the most recent significant leadership lesson you've learned?

"Other people aren't the problem." Meaning, if there is a consistent issue, it is likely I am the root cause. I am the one who needs to adapt and change. It is far easier to change one person, especially when that one person is me, than to change multiple others.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

Meditations by Marcus Aurelius. This book really helped me shift my perspective from being "right" in interactions with my team, my clients, and my family, to seeking to learn first in each interaction. Rather than going in trying to impart knowledge, I go in seeking to gain knowledge. It has helped me grow as a person and as a leader, and as a result has helped me take my company to new heights.

6. How do you build leadership capacity in an SME?

As with sports, it is cross training. There is a portion of "just doing," as in working day in and day out as a leader in the business. This, however, is not enough. Through feedback (structured weekly, quarterly, and annually), as well as engaging outside coaches and 360-reviewers, provides a way to collect "tape" on how that day to day work is going and how it can be improved. Additionally, active reading and learning from others helps me generate new ideas and ways of leading more effectively.

7. What is one meaningful story that comes to mind from your time as a leader of an SME so far?

I was recruiting a new employee, but the person was unsure if he should take the job because he was contemplating starting his own company. I responded that every single person's time at Rented was limited, even my own. The commitment he would be making to Rented was not for life, but that for the life of the time he was there to give it his all. In turn, my commitment was to help him grow and learn as much as was humanly possible during his "life" at Rented. After 3 incredible years where he built and scaled a new part of the organization for us, I helped him transition to founding his own new venture where he recently raised several million in venture capital investment. The leadership, and the commitment to growth, is not limited to this single company. A company is an abstract thing. In reality it is a collection of real individuals. My objective is to lead those individuals with purpose, and the "company leadership" will follow from that. That particular employee's journey to me is a good illustration of me living my personal leadership values, which is why I like it so much.