Faces of Shift with Fly StraightLine & Pepper Pong

Tom, you have a broad professional background! Tell us about your ventures. 

I’m an entrepreneur owner & operator of a diverse group of businesses I’ve founded and/or acquired, spanning various industries such as private aviation, ecommerce, and sports.  

Under the umbrella of my aviation holding company, Aviation Innovation Holdings (AIH), are three primary companies – Fly StraightLine (membership-based, on-demand private aviation services), Charter Flight Support (functions like travel insurance for private charter flights), and FlightLink (a tech-driven platform monetizing spare flight capacity). 

On the ecommerce front, I invented Pepper Pong (www.pepperpong.com), a unique, highly-portable racket sport complete with its own rules and gear. After years of nurturing this idea, it was finally launched in June. Many liken it to a miniature version of pickleball.   

Further connecting me to the world of pickleball, I acquired Pickleball Portal (www.pickleballportal.com) in 2020. It’s a prominent online platform that curates product reviews and content for pickleball enthusiasts, attracting over 150,000 unique visitors monthly. 

My journey as an entrepreneur began in my mid-20’s when I launched my first venture, Exclusive Resorts (ER). We pioneered the niche of luxury destination clubs, whereby consumers secure a membership, granting them access to a vast array of luxury vacation homes spread across the globe. We were backed and eventually acquired by Steve Case, the visionary behind AOL. Under my leadership, we employed over 1,000 people, grew our real estate portfolio to upwards of $1.3 billion and delivered over 100,000 unique travel experiences across all seven continents. 

 What differentiates each enterprise from its competitors?  

A consistent theme that sets my aviation enterprises apart is our innovative business models. We aim to demystify intricate and fragmented categories, providing consumers with transparency and compelling value. This is furthered by our commitment to utilizing cutting-edge technologies which, whether developed internally or sourced externally, optimize efficiency and reduce costs. 

When it comes to Pepper Pong, its uniqueness stands out. Imagine the portability and universal appeal of a deck of cards, but translated into a dynamic, fun activity for all ages & skill levels in any setting. It fosters connections through the joy of competition. 

As for Pickleball Portal, our competitive advantage is our exclusive network of writers. Unlike many platforms that provide cursory overviews, our experts are deeply invested and meticulously craft comprehensive reviews, ensuring that readers gain significant insights, elevating us above platforms that merely skim the surface. 

How do you keep your private aviation and luxury travel businesses up to date on the current trends? 

I have an insatiable appetite for reading and am always on a quest for knowledge, pondering the future. I tend to strategize by looking 3-5 years ahead, identifying potential gaps, and aligning my businesses to address those. I place significant emphasis on staying abreast of the latest technologies and quickly deploy those that I believe will serve to differentiate us in the marketplace. 

What about your business and/or industry inspires you?  

What truly motivates me is the ability to turn my visions into tangible realities. With the plethora of tools available today, realizing these dreams has become more accessible than ever before. Without today’s tech, there’s no way I’d be juggling 5-6 businesses at once. It’s inspiring to think about bringing even more of my ideas to life in the coming years. I generally build companies around my personal passions, so in some regard, it’s in my self-interest to keep going!  

 What is your long-term company vision or goals? 

 As I look forward, I think about starting and scaling a few more businesses before I start working on a big idea that blends all my passions and business experiences into one. I’ll always focus on businesses that feed my personal passions for flying, outdoors, travel & sports.  

 We know you enjoy traveling – any fun trips planned? 

 We have many trips planned over the next 4-6 months, some to scratch the itch of our family’s newfound love of kitesurfing, to visit our oldest daughter at the University of Michigan, college tours for my younger girls, etc.  

 What do you enjoy doing outside of business?  

 One of my personal passions is flying, I’m an instrument-rated private pilot. I combine that with my lifelong love for fly fishing to get off the grid and away from the crowds. My girls love to fly with me, so we’re always out doing something fun.  

 How has joining Shift Workspaces Corona contributed to your growth and success?  

My wife, 3 daughters & I live less than a mile away, making it super convenient for me. I know enough about myself by now to know that I do my best work when I’m in an inspired “flow state” and so the fact that I can get to the office quickly (in this case in under 90 seconds!) is ideal. The vibe at Shift is friendly and comfortable, so it’s the ideal setup for productivity. 

 Pepper Pong 50% Off Discount Code for Shift Members:  2023SHIFT50 


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