5. Steve Jobs

Model: Gulfstream V
Cost: $88 million*
Net Worth: $10.2 billion*
The late Steve Jobs was worth billions, thanks to his founding of Apple. The former Apple CEO had to travel in style, so he purchased a Gulfstream V, worth a total of $40 million initially. Once Jobs’ modifications were complete, the total cost, which Apple wrote off as a business expense, was around $88 million.

After Jobs’ death, Laurene Powell Jobs, his widow, inherited it. She didn’t keep the private plane for long, selling it to Jony Ive for just a fraction of what it originally cost. Ive, an Apple designer from 1992 until 2019, reportedly took one look inside the jet and said, “At least I don’t have to redesign anything.”