Originally Posted by
surak
Use a different set of tires that are an easier fit on your rims.
Get a Koolstop bead jack. Carry it with you on rides or hope the tires stretch out.
I do start opposite the valve because you can squeeze more of the tire from there, but for my hands' sake and sanity I just use the Koolstop unless the tire is well-stretched.
Amazing, I had no idea such a tool exists. Just ordered it on Amazon. Thank you!!!!