When the iPod debuted at $399.99 on October 23, 2001, Apple Inc stock sat at $0.34 a share so this theoretical exercise begins with a nice round'ish 1175 shares with the change getting charged to the game about $160,000 in 2022 dollars for an adjusted for inflation investment of $669.30. Let's be real, if you've held onto AAPL for all these years, HODL is your way of life, and selling shares is blasphemy.
The Mk3 iPod above looks chunky but both it's 5.6 ounce weight and the Mk1 iPod's 6.4 ounces weigh marginally more the Apple's current lightest comparable model, the iPhone SE rocking the scales at a svelte 5.09 ounces. The Sony MD players pictured for scale predate my Mk3 iPod, became instant paperweights that my Inner-Hoarder just couldn't throw away.
Steve Jobs' 2001 iPod introduction provides excellent context on the portable music players from that era in the video below. It's going to sound crazy, but even knowing that I could've made millions of dollars instead of buying my first iPod in 2003, I still feel my life would have been different in unpleasant ways because the liberating feeling of finally having access to any music I wished was a phase change in my technological progression. Watching a hale Steve Jobs talking about biting his fingernails is something that I don't remember when watching this back in 2001, just 42 days after 9/11; and it feels so incredibly period correct to hear Jobs sing along with The Beatles, like a video Easter Egg of unfiltered nostalgia lying in wait for those willing to click.
Correction: $160,000, not $9m.