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

The most difficult challenge that I have faced has been understanding the timing of everything. When you start a company with a small amount of capital, there's a unique timeline that you have to operate on. Sales need to be closed by a certain time, development projects need to be started by another, and new investors need to be on board by specific dates. There's a lot to juggle, and it starts by gaining a full understanding of what needs to get done and when it needs to be completed.

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

We have been in business for over a year now, but we recently started falling into our roles officially in late July, around the time we brought our CTO on board.

Our CTO, James Ramsey, has been a tremendous help, and we would not be where we are today without him. He along with our Senior Dev Ops manager, Adam Miller, has built our web app and image processing pipelines which have given us the ability to expand and develop in a much more streamlined and effective manner.

These developments have given us the ability to acquire top talent on the sales and operations sides of things that would not have been possible otherwise. They have also allowed us to expand quicker and take on high volume high profile clients that we would not have been able to service without the software that we now have in place.

This expansion has given me the ability to step into the position that I am in today, where I am now working to resolve big picture issues.

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

In the mornings, I will get up and check my email, texts, and slack for any important messages that need to be resolved quickly. Once I have answered my most time-sensitive messages, I will get ready for the day.

Typically I will have a meeting with either my sales, operations, or dev team early in the morning to go over important updates, figure out schedules, etc. From there I will typically have sales meetings to attend until the afternoon. After those meetings are over I'll grab a bite to eat, and head back to the office. In the afternoon, I will finish answering emails, calls, etc. In the late afternoon/early evening, I'll save some time to meet with either potential investors or my advisors.

Once standard business hours are over, I'll move on to administrative work. This includes reviewing company financials, creating presentations, and being a part of interviews like this one! On an average day, I'll probably finish my work at 9 pm, eat dinner, and then head to bed for the night.

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

The most important lesson that I have learned is that it is important to be humble when your employees and partners are sharing their input/ suggestions. Something that many executives fall victim to believes that they alone can guide their company to success, which couldn't be further from the truth.

The fact of the matter is that I bring on experts in their fields because they know and understand things that I don't. My development team understands how to build our software better than I do. Our operations team understands how to resolve complex logistical problems better than I do. My sales team understands how to sell better than I do.

My goal as a CEO isn't to micromanage my team, but to hear their input and their suggestions and turn it into proper management decisions that drive the company forward.

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?

I can't honestly say that there is a book that has greatly affected my leadership personally. However, what I can say is that going out and having in-depth conversations with people all across the spectrum has changed the way I think dramatically.

Whether it be a top-level executive or an unpaid intern, every conversation that I have teaches me something. It can be something as important as words of wisdom or something as simple as understanding what makes someone feel important. Every exchange yields wisdom, and that knowledge has been influential in my life.

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

I have developed my leadership capacity in two significant ways. The first is failing, and the second is reevaluating why I've failed with a mentor or by myself. There are many unknowns that I have faced and continue to face, and I've begun to understand that it will be this way until I retire.

The reality of entrepreneurship is that there's only so much that you can do to prepare for difficult situations. Sometimes the best thing you can do is mess up and learn from your mistakes. Recovering from demoralizing failures, broken expectations, and humiliating experiences has turned me into a stronger and wiser leader.

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

Probably the most meaningful story I have is from my first sale. It was with a smaller farmer in southern Arizona, and to be completely honest I butchered it. I said all of the wrong things, I stumbled through my pitch, but I was persistent. I kept going back to this grower over and over and got through about a dozen awkward presentations and phone calls, but eventually, I was able to get through to the client and close my first sale.

The part of the story that I'm proud about isn't that I closed the sale. To be quite honest, it was insignificant in the grand scheme of things. The part of the story that I am proud of is that I kept going back to that grower time and time and again, even though it was hard, even though I didn't know what I was doing, even though it was humiliating botching my pitch over and over. I was willing to do it because I cared deeply (and still do) about what we are building at Farm Flight.