During Chapter 4, you'll unlock a Race questline. Complete all the events within the questline and you'll unlock the achievement. None of these are particularly difficult as long as you're buying one of the 200+ rating cars.
Note that side bets are deducted no matter what. So if you do restart the race or lose, you lose the initial investment. So if you do have trouble on a race and have to restart a few times, keep in mind you lose your side bet money each time.