I believe it’s very important to take time for yourself and do something that completely takes your mind out of work. I’m a surfer, so for me personally I go on a surf trip by myself for two weeks every year. It completely takes me away from my “normal” world and allows my brain to completely check out on the stress of running a company. I also do lots of small things to keep my mind optimized. I have found that exercise and keeping my body fit helps my mind more than anything. I also love to cook! Surprisingly this is an amazing check out for my mind and the result is good food, which is a bonus. Also, sleep is super important for obvious reasons, so I try to get to bed early when I can. When I am in the office, I try to get all my meetings done in the morning when I’m fresh. Lastly, I try to make as few decisions as possible and only focus on the big challenges.
As a part of our series about “Optimal Performance Before High Pressure Moments”, I had the pleasure of interviewing Jason Middleton.
Jason Middleton is the CEO of Silver Air, a private jet management and charter company with operations in Los Angeles, the Bay Area, Seattle, Dallas, Houston, New York and Florida. Jason built Silver Air based on his vision for an owner-centric and customer service-oriented management/charter company. A true team leader, he hires the best professionals in the industry and invests in their success, inspiring his team to continually find new ways to create an even better experience for jet owners and charter guests.
Jason developed his natural leadership abilities in endurance athletics, completing his first Ironman at 15, and has more than 300 endurance races and seven Eco Challenges under his belt. After transitioning to aviation during his athletic career, he quickly became a sought-after aviator before starting Silver Air. Jason lives in Santa Barbara with his three children.
Thank you so much for joining us in this interview series! Before we dive into the main focus of our interview, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?
I grew up in Bakersfield CA. My father was a police officer and my mom had a wallpaper business. I was a chubby kid and the worst athlete in school — I was always the last kid picked for sports. I was motivated to change so I started swimming, which led to running and then I found triathlons at the age of 11. It was the first time I can remember being motivated to do anything other than watch TV and play Legos. By the time I was 15 I was on the US national team racing nearly full time. Luckily, I found athletics because I was a terrible student. I was such a bad student in fact, that I barely graduated high school. After high school I turned professional in triathlons, marking my first real exposure to the world outside of Bakersfield. In my early 20’s I had the opportunity to compete in an ultra-endurance team race called Eco-Challenge (which became World’s Toughest Race and is now airing its latest season on Amazon Prime). I found I had a lot of talent for long, physically challenging races and went full time into it from there.
What or who inspired you to pursue your career as an entrepreneur or business leader? We’d love to hear the story.
During my early adventure racing days, I competed on a number of teams with varying success. Because it is a team sport, you need the right members to really be competitive. My girlfriend at the time encouraged me to start my own team. I didn’t realize it at the time, but this was my first entrepreneurial venture. I had to go out and find sponsors, manage budgets, recruit the right team members, work on media for the team, and manage logistics and travel schedules. I ultimately created Team Earthlink and we became one of the best adventure racing teams in the world. This time in my life was by far the most educational and developmental to my future as an entrepreneur. I wouldn’t be where I’m today without the lessons I learned during my adventure racing days.
None of us can achieve success without some help along the way. Was there a particular person who you feel gave you the most help or encouragement to be who you are today? Can you share a story about that?
Yes, my parents for sure, especially my dad. He would always say you can be anything you want to be and accomplish anything you want to accomplish in life. I didn’t understand at the time, but he was right, and I hear his voice when things get hard. I wish he was here today to see what we have accomplished with Silver Air.
Can you share the funniest or most interesting mistake that occurred to you in the course of your career? What lesson or take away did you learn from that?
I’ve made a lot of mistakes along the way! The first big mistake I made happened during my first year of running Team Earthlink. Our main sponsor (Earthlink Internet) paid us nearly $1mm to cover our team budget for the year. Since I didn’t know what I was doing as a businessperson, I had them pay me personally to cover our entire budget for the year. I also didn’t realize I needed to pay taxes on the 1099 I received from our sponsor. After spending the entire budget on our race season, I received a very large tax bill from the IRS. Being totally clueless and not realizing I should probably talk to a tax accountant, I just called the IRS directly. They were surprisingly helpful and easy to work with. Maybe they felt sympathy for me because I was a clueless kid in my early 20’s, but I was able to work through the tax issue directly with the IRS and took care of the whole thing without ever talking to an accountant.
The road to success is hard and requires tremendous dedication. This question is obviously a big one, but what advice would you give to a young person who aspires to follow in your footsteps and emulate your success?
Believe in yourself and your vision but be humble. Seek out and listen to other people’s experiences. Keep things simple, focus on what you are good at and become great at it. The more laser focused you are on one thing, the better you will be at that one thing. If you focus on five things, you will never be great at anything. And lastly, be prepared for things to be 10x harder and take 10x more time than you think they should.
Is there a particular book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?
Ironically, when I was 17 years old, a friend gave me a copy of Personal Power by Tony Robbins on cassette tape. Now, 30 years later, I am lucky enough to work with Tony! The two key things I learned back then from listening to Tony were: don’t let fear drive your decisions and don’t be afraid to make mistakes.
Can you share your favorite “Life Lesson Quote”? Why does that resonate with you so much?
“If you don’t regret doing it at some point along the way, it’s not worth doing” — Jason Middleton
Meaning, everything in life that is meaningful and fulfilling comes with challenges and roadblocks. At some point along the way you will question why you are doing the hard thing, but it’s worth it.
What are some of the most interesting or exciting projects you are working on now? How do you think that might help people?
I get really excited about improving the quality of our business for our customers and our team of amazing employees. We looked at the COVID pandemic as an opportunity to show our people that we truly care and decided at the outset that we would not make any layoffs. In fact, we hired 28 people since the start of the lockdown. We have also been working on internal education and communication. Externally, we have been spending a lot of time on our marketing and branding with a focus on education for our clients.
OK, thank you for all of that. Let’s now shift to the core focus of our interview. As a business leader, you likely often face high stakes situations that involve a lot of pressure. Most of us tend to wither in the face of such pressure and stress. Can you share with our readers 3 or 4 strategies that you use to cope with the burden of stress?
For me personally, I hate stress and I’m not good at dealing with it. When things get exceptionally challenging, I get super focused. I immerse myself in solving one problem at a time. I over communicate with my team and try to get them on the same page, working together to solve the one problem. This tends to lower stress levels and allows us to make clear, efficient decisions. Some techniques I use are:
· Take a pause — Don’t react first, think first
· Break the problem down — Figure out what the real problem is
· Identify the most critical issue — Find the most important thing to focus on and forget the rest for now
· Outcome first — Define the ideal outcome
· Drive — Drive your most critical problem to the ideal outcome
This seems simple, but the hardest part is getting past the fear of your current situation and working towards a solution. I learned very early in my adventure racings days that there is ALWAYS a path to success, you just have to figure it out.
Aside from being able to deal with the burden of stress, can you share with our readers 3 or 4 strategies that you use to optimize your mind for peak performance before high pressure, high stress situations?
Yes, I believe it’s very important to take time for yourself and do something that completely takes your mind out of work. I’m a surfer, so for me personally I go on a surf trip by myself for two weeks every year. It completely takes me away from my “normal” world and allows my brain to completely check out on the stress of running a company. I also do lots of small things to keep my mind optimized. I have found that exercise and keeping my body fit helps my mind more than anything. I also love to cook! Surprisingly this is an amazing check out for my mind and the result is good food, which is a bonus. Also, sleep is super important for obvious reasons, so I try to get to bed early when I can. When I am in the office, I try to get all my meetings done in the morning when I’m fresh. Lastly, I try to make as few decisions as possible and only focus on the big challenges.
Do you use any special or particular breathing techniques, meditations or visualizations to help optimize yourself? If you do, we’d love to hear about it.
I use visualization a lot, which comes from my days as an athlete. I constantly visualize the goal or outcome I am looking for and the path it will take to accomplish the goal. I believe meditation is also a very valuable tool. Meditation can come in many forms. For me, it’s surfing. I find it very meditative to paddle out to the line and be singularly focused on the ocean, the waves, the sounds and the feeling of riding waves.
We all know the importance of good habits. How have habits played a role in your success? Can you share some success habits that have helped you in your journey?
I do something for myself every day. It doesn’t need to be anything specific, but I try to fit something in every day that is just for me. It could be working out or surfing or simply cooking dinner. I have found it to be super healthy for me to activate my mind and body on something that is not work related every day.
What is the best way to develop great habits for optimal performance? How can one stop bad habits?
Try different things and see what works for you, then do more of that thing.
As a business leader, you likely experience times when you are in a state of Flow. Flow has been described as a pleasurable mental state that occurs when you do something that you are skilled at, that is challenging, and that is meaningful. Can you share some ideas from your experience about how we can achieve a state of Flow more often in our lives?
Yes, find one thing you are passionate about, make it your mission to be great at it and become obsessed with always improving your skill, knowledge and understanding of that thing. No matter how good you become at something you can always be better. Always be curious about your craft and seek out new innovations and different perspectives. Become a mentor and share your knowledge with others. It’s amazing how much you can grow and learn by teaching others.
Ok, we are nearly done. You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
I wish the world had more empathy. I talk about empathy a lot in my personal and business life. It’s the foundation for understanding others. It’s nearly impossible to give people what they need unless you have a true understanding of the perspective they are coming from. Our world has become so polarized with politics, race and cultural differences and we have a tendency to react, rather than listen. If people exercised more empathy and really tried to understand their fellow humans in a meaningful way, we could solve a lot of the world’s problems.
Is there a person in the world, or in the US, whom you would love to have a private breakfast or lunch with, and why?
For me, it changes depending on what is going on in my life. I would say right now, there are two people I would want to sit down with for very different reasons. First is author Ryan Holiday. His work on stoic philosophy is fascinating to me. His book, Ego is the Enemy, should be mandatory reading for anyone in a leadership position. The second is surfer Kai Lenny. His love for his craft and positive approach to life is infectious to both surfers and non-surfers alike.