Two tips on how I got the achievement:
#1 REMEMBER SCOOTER PARTS! Make sure you have a scooter with high speed and handling. The setup I used for this was: X-Bars, Cracked Deck, and Patched-Up Wheels. These three combined kept speed and handling super high.
#2 Easiest track in my opinion is Crayola Color City - Streets. Two almost always come straight out the narrow exit and the other two normally hang around in the starting area. As soon as you start spam the boost and push. You should be able to catch the first two no problem.
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First try with this setup and I was able to get it. However, I tested multiple times. It may take a few attempts but be vigilant it will come!