Preston Holland is the Chief Commercial Officer at FLYING Finance. FLYING Finance is an aviation finance company that helps buyers and fractional owners of airplanes secure traditional or creative financing for personal and private aviation.
Preston has a deep understanding of the aviation industry and a commitment to making dreams take flight. Preston and his team provide tailored financing solutions for the purchase of business jets, piston aircraft, turboprop aircraft, helicopters, and more.
In addition, Preston writes a weekly newsletter called “Learn To Fly Private,” focused on teaching business owners and high net-worth individuals the ways they can fly private.
Before leading FLYING Finance, Preston was COO and second in command for the Private Equity-style roll-up at FLYING Media Group, which acquired 28 Aviation and 10 Marine media brands including FLYING Magazine, aircraftforsale.com, AvBuyer.com, and more.
Listen in for some great takeaways about Preston’s journey in the aviation industry, and how his passion for the profession has allowed himself, his team, and his clients soar to new heights.
You will want to hear this episode if you are interested in…
- Learn more about Preston Holland and FLYING Finance [3:18]
- Why Preston and his team purchased FLYING Magazine [9:20]
- Building FLYING Magazine into a multi-media empire [13:27]
- FLYING’s master-planned air park community [15:05]
- How to get your “Joy and Productivity Journal” [17:54]
- Becoming the Chief Commercial Officer of FLYING Finance [21:29]
- The biggest misconception about flying private [22:57]
- Preston’s biggest tip about flying private [28:30]
- What Preston did today that put him in the mindset for success [33:27]
Learn more about Preston Holland and FLYING Finance
In 2021, Preston was a GM for a regional service business in the Southeast. He helped them triple their revenue and grow their team. He had no intention of leaving—until another friend called and told him he was purchasing “FLYING Magazine.” His friend asked him to join him on the journey.
They have 7 million eyes on their websites in any given month. So they asked the question: What can we do to help these people? They acquired a small finance brokerage. Preston started the hard work to turn it around. They’re growing 100% month over month.
They help facilitate transactions in the private aviation space, anything from a small prop plane to an Elon Musk-style jet. They meet with their customers to understand their financial goals (why they’re buying an airplane) and go to market for them. They work with around 100 lenders to find a package that works perfectly for their customers.
Building FLYING Magazine into a multi-media empire
Preston emphasizes that the private aviation space customer appreciates quality. Preston and his team started creating a product people wanted to read. These people are passionate about aviation—something with a high barrier to entry.
As aviators themselves, Preston and his team understand what their buyer persona cares about. So they set out to create ancillary businesses built around the magazine to come alongside their advertisers.
But they also know this group of people needed to be reached digitally. They’ve built an integrated partnership with Apple. They’re syndicated to Apple News+ in an advanced digital market. They have 28 different websites. Web readers are often top of the funnel. The print product takes them to the next level.
Getting and staying top-of-mind with your target audience is a constant topic of conversation in every business. It’s hard to make money with a media business. But they had a captive audience. They wanted to build ancillary services around the magazine to serve their audience and help them do what they love to do.
FLYING’s latest venture: A master-planned air park community
They recently bought 1,800 acres in Southeast Tennessee to create an air park, or what they like to call a “fly-in community.” It’s a beautiful environment that’s a two-hour flight from 70% of the American population.
They’ve collected $27 million of pre-funded deposits to build the master-planned community (which also allows the investors to reserve their space). They’re building a 4,300-foot runway, accessible to any single-pilot aircraft. The community will also have a grocery store so all of their basic needs can be met on-premises.
30% of it will be primary homes and the other 70% will be a transitory population. They’ll also be creating a hotel on-property so guests can enjoy the amenities on-site but only stay temporarily.
There’s a growing demand for these communities. People want to be near like-minded people. Flying is part of their identity.
What are the biggest misconceptions about flying private? What are Preston’s biggest tips for someone looking into chartering a private plane (or buying their own)? Listen to the episode to learn more!
If you want to fly private and don’t know where to start, Preston is happy to help. Subscribe to his newsletter for a free 15-minute call or reach out on Twitter!
Resources & People Mentioned
Connect with Preston Holland
Bio
Preston Holland is the Chief Commercial Officer at FLYING Finance, an aviation finance company that helps buyers of airplanes and fractional ownership secure traditional or creative financing for personal and private aviation. In addition, Preston writes a weekly newsletter called “Learn To Fly Private” focused on teaching business owners and HNW individuals the ways they can fly private. Prior to to leading FLYING Finance, Preston was COO and second in command for the Private Equity-style roll up at FLYING Media group, which acquired 28 Aviation and 10 Marine media brands including FLYING Magazine, aircraftforsale.com, AvBuyer.com, and more.
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