On the flip side, consider PalmOS. It was SotA at its debut in 1996. In the early aughts, Palm made Treo smartphones when almost no one knew what a smartphone was. It had a multiyear lead, yet it got easily marginalized by iOS and Android. Its technical debt was from maintaining backward compatibility with 90's apps, and cost it dearly. To be fair, company management sucked too.
The moral is: caked-in issues suck, but if you're going all in with a design, the most important thing is to time it with the explosion of the market. Palm was too early, others like Maemo and Windows Phone were too late.