Can two friends race on different courses at same time?

New user here.  I want to race my friend but we go at different speeds.  I’d like to see if I can finish the Volcano Climb course (14.2 miles) before he can finish the Mountain Route course (18.3 miles).  Is this possible, and if so, how would we set this up?  If not, and we HAD to do the same course, would I be able to take some shortcuts to get my distance shorter?  Thank you.

Just give the slower rider a head start .

You and your friend can certainly be at those certain courses at the same time. But when you ride with a friend it places you where they are, so essentially the same course. There aren’t any shortcuts however. 

Thank you, Robert.  That is definitely the simplest way to go.  That’s what we’ll do.

Thank you, Vincent.  That makes sense.