They had the "Knowledge Navigator" vaporware in 1987, twenty years before iPhone.
https://en.wikipedia.org/wiki/Knowledge_navigator
They started working on realizing the KN concept in 1987, and shipped Newton in 1993, fourteen years before iPhone. Alas, the state of tech was not up to their ambition.
https://en.wikipedia.org/wiki/Apple_Newton
They shipped iPod in 2001, six years before iPhone. In conjunction with iMacs that could rip CDs, they had a massive hit!
Then they shipped iPhone in 2007. The greatest hit in product history.
What made it possible to have so many kicks at the can was, of course, having a successful(ish) business selling Macs.
With VC funding, you strip all the legacy/cash cow business out of the equation. In exchange, you get tremendous financial leverage for founders, but you also have a very limited window in which to ship a hit.