After the Deal: When Can You Afford to Fly Private? with Preston Holland

Selling your business changes everything. But what happens next?

That’s why we created the After the Deal series on Built to Sell Radio. This series explores life after selling a business—delving into the personal, financial, and emotional transitions that come when work becomes a choice, not a requirement.

In this episode, we speak with Preston Holland, author of Private Jet Insider and an expert in private aviation. Preston shares why private jet travel isn’t just for celebrities and explains how business owners use private aviation to buy back their most valuable asset: time.

You’ll discover how to:

• Evaluate the financial benchmarks for chartering, fractional ownership, or buying a plane.

• Determine the “2 and 20 rule” for private jet readiness.

• Use private aviation to gain a competitive edge in business.

• Keep your private jet use… private.

• Navigate the world of charter brokers, jet cards, and fractional ownership.

• Identify whether private aviation is right for your post-exit life.

Whether you’re growing your company or preparing for life after an exit, Preston breaks down the costs, commitment levels, and unexpected benefits of flying private, making this episode a must-listen.

Show Notes & Links

Check our Private Jet Insider

Follow Preston on X

Connect with Preston on LinkedIn

About Our Guest

Preston Holland

Preston Holland is the founder of Private Jet Insider and a seasoned expert in the luxury aviation industry. With years of experience helping individuals and businesses navigate the world of private aviation, Preston has become a trusted voice for those looking to elevate their travel experience. His work focuses on simplifying the complexities of private jet ownership, charters, and fractional programs while delivering insider tips and strategies to maximize value and convenience. Known for his deep industry knowledge and ability to demystify the private aviation space, Preston is dedicated to helping clients achieve seamless, luxurious, and efficient travel solutions.