To begin, you will want to play well in the 'MyCareer' portion of the game, and continue to build fans (doing endorsements, meeting with other NBA players etc).
Pay special attention to the shoe endorsement company (Nike, Jordan, Adidas etc.) events and make a strong effort to attend each event for your chosen shoe company during the season. This will allow you to progress through the levels of compensation for your shoe company faster.
After you reach 'level 4 compensation' on your shoe deal, you will soon be able to attend the signature shoe event for that company (this will appear in the schedule like every other event). After this event (where you create your shoe), you will be given the option to create a shoe commercial that is either 'funny' or 'serious'.
To get the achievement, you simply need to choose the 'funny' variation of the signature shoe commercial.
This can be done on any difficulty, and it is possible to be done in your first season; however, you will have to accomplish this before the start of the playoffs. If not, you will have to wait until your second season as there are no events (other than 'free practices) active during the playoffs.