[1] Jerry Media founder Elliot Tebele came up with the idea of writing whimsical messages on protest signs, posting a few on Instagram, and employee Seth Phillips later picked up the idea.

[2][3][5] Phillips's first post, featuring a sign reading "Stop 'replying all' to company wide emails", went viral in October 2019.

[3][4] Sponsored content appeared on the account by early 2020, including advertisements for Old Spice, Sprint, and Justin Bieber's album Changes.

[1][6] Later partnerships have included ads for multiple underwear brands,[7][8] a Super Bowl ad for Bud Light Seltzer Lemonade,[9] and informative COVID-19 pandemic posts partnering with both the World Health Organization and President Joe Biden.

[10][11] BuzzFeed News reported in 2023 that at least seven lawsuits had been filed against companies that had created their own Dude With Sign ads without permission.