This is a story related achievement.
During Chapter 5, you'll unlock an offroad questline. Complete all the events within the questline and you'll unlock the achievement. These races can actually be rather difficult. The second and third have a lot of sharp turns on cliffs which can be rough. The fourth and fifth involve a construction site with a lot of obstacles to hit.
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.