Selling your business changes everything. But what happens next? That’s the focus of our After the Deal series on Built to Sell Radio. These episodes dive into life post-sale, exploring the personal, financial, and emotional shifts that come when work becomes a choice, not a requirement.
This week, we’re joined by Preston Holland, author of Private Jet Insider, to tackle one of the most common questions entrepreneurs face after selling: When can you afford to fly private?
Flying private is often seen as the ultimate luxury, but Preston explains why it’s also a strategic tool for business owners. Whether it’s saving time, boosting productivity, or creating meaningful experiences, private aviation offers more than meets the eye.
Here are some benchmarks Preston shared:
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Chartering regularly starts at a net worth of $20 million and $2 million in annual income.
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Fractional ownership requires a $600,000 investment for a light jet share, with monthly and hourly costs on top.
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Buying a jet outright typically means $100 million in net worth and $10 million in annual income.
Preston also breaks down the four ways to fly private, from one-off charters to full ownership, highlighting the trade-offs and financial commitments of each option.
What You’ll Learn:
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The “2 and 20” rule: when to start chartering.
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Why private aviation is more like Elon Musk than Kim Kardashian.
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How to maintain privacy while flying private.
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Why flying private is often about buying back time, not flaunting wealth.
After the Deal episodes are about more than what money can buy—they’re about the new opportunities and challenges that come with life after selling your business. Preston’s insights bring clarity to a topic that’s often shrouded in mystery, making this episode essential listening for anyone thinking about their post-exit life.
Quote of the Week
Most private jet owners look more like Elon Musk than Kim Kardashian—they’re running businesses, not showing off.
Deals
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DealerClub, a digital wholesale auction platform that connects automotive dealers through a reputation-based system, has been acquired by Cars.com Inc. (NYSE: CARS) for an initial payment of $25 million in cash, with the potential for up to $88 million in additional performance-based consideration. The transaction, which closed on January 23, 2025, expands Cars.com‘s presence in the wholesale used car market and introduces a new transactional revenue stream. DealerClub serves over 650 dealer customers, generating revenue primarily through transaction fees. If all performance milestones are met, the total acquisition price could reach $113 million.