David Zipkin of Tradewind Aviation

    We Spoke to David Zipkin of Tradewind Aviation on Being an Effective Leader During Turbulent Times

    As part of our series about the “Five Things You Need To Be A Highly Effective Leader During Turbulent Times,” we had the pleasure of interviewing David Zipkin.

    David Zipkin is a founding member of Tradewind Aviation, the leading regional mobility solutions provider operating on-demand private charter and scheduled shared charter flights throughout North America and the Caribbean. As Vice President of Tradewind, David is responsible for sales, marketing, and business development. Prior to co-founding Tradewind with his brother, Eric Zipkin, in 2001, David served as brand and product director for several leading online marketing services and firms.

    David is an instrument rated pilot and holds a B.S. in Finance and Management Information Systems from the University of Vermont. With a keen understanding of aircraft operations, Tradewind is committed to the highest levels of safety by providing the greatest quality aircraft, crew, and service.

    Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

    I am a co-founder and the Vice President of Tradewind Aviation, a private charter operator and airline based in Connecticut, with operational bases in New York and Puerto Rico. My brother Eric and I grew up around flying, inspired by our father who was an aviation enthusiast and private pilot. Our father was a serial entrepreneur and taught us to always look for ways to do things better. Eric caught the flying bug early and landed his first business aviation job with a private charter operator in Westchester, NY. In this experience, Eric immediately saw that while traditional private jet service offered a premium luxury experience, the service level on smaller plane flights was severely lacking. Tradewind was then formed in 2001 on the premise that all flights deserve the highest quality crew, aircraft, and service. We began with one 8 seat Cessna Caravan; today, we operate a fleet of 24 aircraft with 180 talented team members.

    Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

    One early mistake we made was severely underpricing our flights. The goal with our scheduled shuttle offerings is to provide the private flight experience for the cost of a single seat, and these flights are operated from private jet terminals with private lounges, valet parking and expedited security — all of which come at a significant cost. We didn’t fully factor in this high cost of operations when we first began Tradewind, but our clients, of course, loved it!

    In the end, though, they are happy to pay more for such an elevated level of service. We learned that higher pricing is ok if you can deliver the caliber of experience to back it up.

    None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

    In the early years of Tradewind, our good friend David Zara always told us, “Tradewind is in the service business, not the aviation business.” His obsession with service and the client experience ultimately served as the guiding light for our company’s principles and ethos to this day. I recall a moment years ago when after a client’s bag was temporarily lost, David wanted to deliver a bottle of champagne to their villa, but it was too late in the evening. He turned to me and said, “let’s go” and off we went. We didn’t know where they were staying, so after two hours of going door to door and jumping gates, we finally found them and delivered the champagne. Those people have been loyal clients now for over 15 years.

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

    Back around the time when we launched Tradewind, the level of service on large private jets was excellent, but severely lacking on smaller planes with shorter routes, so our mission was to raise the bar for the customer experience on these types of flights. We were, and still are, obsessed with providing the best customer service possible after all these years, which has become an intrinsic part of Tradewind’s brand and reputation.

    Thank you for all that. Let’s now turn to the main focus of our discussion. Can you share with our readers a story from your own experience about how you lead your team during uncertain or difficult times?

    The most recent example for us is, of course, the pandemic. At the outset Tradewind was effectively shut down, and during this time we empowered our teams to work on ways to better our existing practices and methods for when we emerged on the other end. Involving everyone in this process inspired great ideas and gave meaning to work in an otherwise dark period. When business returned, our teams were highly motivated to implement the new projects and ideas that they had been instrumental to creating.

    Did you ever consider giving up? Where did you get the motivation to continue through your challenges? What sustains your drive?

    Not for a minute. We view our team members as family, so providing a stable and successful place to work is very important to us.

    What would you say is the most critical role of a leader during challenging times?

    Communication, even when you don’t have great things to say.

    When the future seems so uncertain, what is the best way to boost morale? What can a leader do to inspire, motivate and engage their team?

    Empowering team members to affect change. People are motivated by the opportunity to contribute, which creates meaning in work.

    What is the best way to communicate difficult news to one’s team and customers?

    In person, in virtual meetings, or on the phone. Stay away from lengthy emails. During the pandemic — and to this day — we hold all company virtual meetings on a regular basis.

    How can a leader make plans when the future is so unpredictable?

    Don’t dwell on uncontrollable circumstances. Focus on the things you can do.

    Is there a “number one principle” that can help guide a company through the ups and downs of turbulent times?

    Never forget your core values. Focusing on this helps everyone see the light at the end of the tunnel.

    Can you share 3 or 4 of the most common mistakes you have seen other businesses make during difficult times? What should one keep in mind to avoid that?

    1. Kneejerk reactions to temporary problems. Focus on core principals and longer-term goals.
    2. Cutting resources in critical areas. Your business is successful because of the talent that you keep.
    3. Lack of communication. In a vacuum people will get discouraged.

    Generating new business, increasing your profits, or at least maintaining your financial stability can be challenging during good times, even more so during turbulent times. Can you share some of the strategies you use to keep forging ahead and not lose growth traction during a difficult economy?

    Sustainable growth. Be prepared to weather a storm. It can be tempting to increase growth at the expense of profitability, but it can backfire, especially in a high-cost business like ours. Many companies in our industry have come and gone in large part due to overly aggressive plans around unproven ideas. We are proud to have created a company that stands on its own.

    Here is the primary question of our discussion. Based on your experience and success, what are the five most important things a business leader should do to lead effectively during uncertain and turbulent times? Please share a story or an example for each.

    1. Communicate well and often. Throughout the pandemic we hosted regular all-company meetings to discuss challenges and plans, and to offer an open forum for questions and input. I know this went a long way towards keeping team members on track and feeling comfortable that we would get through the worst part of the pandemic.
    2. Show empathy, but don’t manage on emotions. Tough times are trying for everyone, but leadership must be the example for calm and stability.
    3. Spend your time wisely. Use the opportunity to learn from the issues that arise during uncertain or turbulent times, and rethink processes to come out of tough times with better systems in place. During the pandemic our teams were empowered to implement improvements, and it paid off in spades as business resumed.
    4. Build a war chest. Tough times can last a while so be prepared. As a company that weathered the 2008 market crash and our fair share of Caribbean hurricanes, we’re always thinking ahead about what could happen and how to prepare for it.
    5. Focus on the long term. During the pandemic, travel restrictions and protocols changed by the day, and it was tempting to go down a rabbit hole with each new challenge we were facing. Team members know what to do for the here and now; leadership must continue to plan for the future.

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

    I like the Mark Twain quote, “The secret to getting ahead is getting started”. This was especially helpful during the pandemic when every challenge seemed new. It’s ok not to know what to do, but it’s important to press forward.

    How can our readers further follow your work?

    Recently, Eric and I have been sharing business insights on our blog and sharing on our Linkedin pages: