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“Look for opportunity everywhere.” With Charlie Katz & Jason Middleton

I would encourage everyone to look for opportunity everywhere. You can stress about where you’re at, but there’s a lot of opportunity. You have to be open to it. Our industry is one thing, but there are so many opportunities that are going to come out of this. So keep your eyes open and be […]

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I would encourage everyone to look for opportunity everywhere. You can stress about where you’re at, but there’s a lot of opportunity. You have to be open to it. Our industry is one thing, but there are so many opportunities that are going to come out of this. So keep your eyes open and be optimistic.


As part of my series about the “How Business Leaders Plan To Rebuild In The Post COVID Economy”, 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.

With health & safety being redefined by the novel corona virus pandemic, Jason and Silver Air recently developed a model program called COVID-19 CLEARED for zero-touch travel. A collaborative effort between Silver Air and expert medical advisors, CLEARED features complete cleaning and sterilization of ground transportation and aircraft, virtual health screenings of crew and passengers, and eliminates potential touch points to nearly zero. This new program is being shared and offered as a model for the private aviation industry.

Jason developed his natural leadership abilities in endurance athletics, completing his first Iron man 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 for joining us Jason. Can you please tell us about your ‘backstory’ and how you got started?

Istarted Silver Air when I was a pilot, working both for management companies and for the jet owners directly. I was able to see both sides of the table. I saw the parts of our industry that worked, and the parts that I thought could work better. And then I was laid off due to financial downturns, which I think a lot of people can relate to now. It was hard to take, and I decided I wanted to take my world into my own hands.

I got together with a few friends who had just sold a software company and another friend with a finance background and we decided to buy an airplane. That was the start of Silver Air, which happened to be in 2008 — right before the last financial collapse. Loans were impossible to get, so we bootstrapped it. We had to be smart and better than everyone else, and we pivoted quickly into aircraft management. I saw an opportunity in aircraft management to be advocates for owners, and so we developed an owner-centric philosophy as one of our founding principles. Our focus was, and still is, on the jet owner’s needs — not up selling services. We advocated for the jet owners, unlike the competition, and this philosophy allowed us to align ourselves with our clients’ goals and really focus on our core strengths, which are managing and operating aircraft.

More than 10 years later, we still focus on those core strengths and doing one thing really well. Over the years, we’ve slowly grown in a healthy, organic way to almost 30 aircraft in our fleet.

Is there a particular book that you read, or podcast you listened to, that really helped you in your career? Can you explain?

Right out of high school I was an athlete, then went straight into flying airplanes. I never went to college or business school, but I am a person who likes to gather information and data. I read a ton of books and try to educate myself.

One of my favorite books is Good to Great. It’s about what separates good companies from great companies and the common traits great companies share. Great companies are generally culture based, and I think we’re very focused on culture and people at Silver Air. We have a people-first, business-second mentality. It’s about giving the right people the right tools. Good to Great also talks about how really great companies are focused on one thing and do it really well. That’s our core belief at Silver Air. It’s very important for us to be very good at what we do.

Extensive research suggests that “purpose driven business” are more successful in many areas. When you started your company what was your vision, your purpose?

Our vision is to be the best at what we do, to empower our world-class team, and to advocate for our clients. Our clients are business leaders, industry leaders, and they depend on us to keep them connected with their businesses and families. When we succeed, then our clients can succeed, and that impacts hundreds or thousands of other people. Traditional aircraft management companies treat aircraft owners like profit centers, but our purpose is to sit on the same side of the table with them and advocate for their interests. There are a lot of things that go into that — what you do, how you do it, the people who run your business, the processes you put in place and the complexity you build into your business. Our vision and our purpose drive all of these things.

Do you have a “number one principle” that guides you through the ups and downs of running a business?

Absolutely. Always focus forward and never give up. There’s always a path to success, no matter what.

That idea comes directly from my adventure racing days. It doesn’t matter how dark or bleak things look there is always, always a path to success, you just have to be open to it. You need to open up your mind to a lot of options and try to see around corners. Keep a broad view of the world around you. Understand all the variables and what you can and can’t control.

The Covid-19 pandemic has affected nearly every aspect of our lives today. For the benefit of empowering our readers, can you share with our readers a few of the personal and family related challenges you faced during this crisis? Can you share what you’ve done to address those challenges?

Silver Air is considered an essential business, so we’ve been working, albeit mostly remotely for now. We believe that our industry will play a critical role in helping restart the economy as our clients start traveling again to connect with their own businesses and customers, so we’ve kept our workforce intact and ready. We’ve created new programs and industry-leading processes to maximize health and safety when traveling. And we’ve implemented company-wide video calls, and even video social meetings. In ways it’s been difficult, but in other ways it’s helped bring us together. Based on the nature of what we do, we’re spread out around the country and we don’t see each other regularly. The necessary adjustments have given us an opportunity to have more face time with a lot of team members who aren’t regularly in the office.

On a personal note, it’s been challenging because my three kids are home, and I’m not an educator. It’s been really difficult trying to home school while running a business. I’ve had to adjust expectations for my kids and be really empathetic to allow them to do what they need to do to get through it. We understand this is hard and we’re all distracted. They’ve all gone through the different stages of grief. They miss their friends and all three of them want to go back to school.

The cool part is, we’re spending a ton of time together. I’ve been cooking a lot and we’ve been doing family BBQs. We also got a puppy. It felt like the timing was ideal.

Can you share a few of the biggest work-related challenges you are facing during this pandemic? Can you share what you’ve done to address those challenges?

Our clients fly primarily for business reasons. Silver Air supports all industries — energy, tech, finance, entrepreneurs, etc. But for the entire month of April, everything was closed and there was nowhere to go. So we pretty much didn’t fly airplanes during the month of April.

We decided to use that time to prepare for when people start to fly again. We built out robust health and safety protocols, not only for the airplanes and cleaning procedures, but including details like PPE for pilots and reduced level of service on aircraft. We also thought about new processes for our customers like how they get to the aircraft, are they wearing PPE, and how close does the crew get to passengers. We had to completely retool our entire flight operations process. We changed every procedure we have all the way from account management to flight support. We had to rewrite the book on how we operate. Our leadership team was in overdrive for the month of April, but now when we do open back up, we know we’ve done everything possible to protect our customers and employees.

Many people have become anxious from the dramatic jolts of the news cycle. The fears related to the corona virus pandemic have understandably heightened a sense of uncertainty, fear, and loneliness. What are a few ideas that you have used to offer support to your family and loved ones who were feeling anxious? Can you explain?

I’ve talked a lot to my kids and my mom, who has been very affected and called crying a few times. I can’t fix all the problems, but I can certainly be empathetic and understanding. One of the best things I can do is be encouraging and listen. I’m a very optimistic person. I tend to always look at the positives in things. The people around me, they feel that and I think that helps.

This pandemic may seem daunting, but if you pare it down to the basics, humans need four things to survive: Food, water, air and shelter. These are the only things we need right now. It may take us awhile to recover, but we are going to be okay.

Obviously, we can’t know for certain what the Post-Covid economy will look like. But we can of course try our best to be prepared. We can reasonably assume that the Post-Covid economy will be a trying time for many people across the globe. Yet at the same time, Post-Covid growth can be a time of opportunity. Can you share a few of the opportunities that you anticipate in the Post-Covid economy?

The economy is going to be very polarized in my opinion. Some industries are going to do fine, some are going to come out better and some (at best) are going to take a long time to recover. We’re going to see people out of work, who need to start looking at different industries. For example, if you’re an airline pilot, you might want to start looking at corporate aviation.

I think there’s going to be massive opportunities for domestic manufacturing. We’re all learning a big lesson here. As much as the world wants to be a global economy, it may not be the best thing for individual countries. Economies are going to become more localized. Not only by country, but even more hyper-local. People are going to be more focused on where they live. There already seems to be a building trend for people leaving big cities and moving to small towns. In talking to other CEO’s, we are trying to figure out how we change business models to allow for more remote work, etc. So, there could be a very cool revitalization of small towns in the United States.

For Silver Air, right out of the gate we are getting interest from a lot of new customers who have never flown private before. I would say about 75% of our new bookings are people who have never flown private before. I think our industry is going to thrive in the post-COVID world. You can’t deny it’s a much safer way to fly in terms of health because we can control the environment.

How do you think the COVID pandemic might permanently change the way we behave, act or live?

I think we’re going to be much more mindful about washing hands and all the basic sanitary things we should already be doing.

Considering the potential challenges and opportunities in the Post-Covid economy, what do you personally plan to do to rebuild and grow your business or organization in the Post-Covid Economy?

Specifically, we’re using this to grow stronger. Luckily for Silver Air, we had a pretty healthy bottom line going into this and we decided to not lay anyone off. One of the things this situation has done for us — it was a litmus test to prove to our people that we’re going to take care of them. Healthcare, benefits, paycheck, retirement are all secure. We’ve had such an amazing response of appreciation from our team. Coming out of this, we’re going to be ten times stronger as an organization than we were before. That’s what I care about. I don’t have any big changes to our business plan, but this has reinforced who we are. One of the reasons we’re here is because we have been careful and conservative about our growth.

Similarly, what would you encourage others to do?

I would encourage everyone to look for opportunity everywhere. You can stress about where you’re at, but there’s a lot of opportunity. You have to be open to it. Our industry is one thing, but there are so many opportunities that are going to come out of this. So keep your eyes open and be optimistic.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

If you don’t regret doing it at some point, it’s not worth doing.

Think about everything you’ve done that is meaningful in your life. You probably regretted it at some point, but it turned out awesome. I would say this every ten minutes when I was competing in the adventure race, Eco Challenge.

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