[4][5] In September 2008, Baio joined the board of directors of Kickstarter, a crowdfunding website that helps people with project ideas to connect with potential funders.

[8] After Yahoo closed Upcoming and offered to sell the domain back to Baio, he launched a Kickstarter campaign that surpassed its $30,000 goal in May 2014 to revive the site.

[10] In October 2018, Baio and his fellow XOXO festival cofounder Andy McMillan announced they would be taking over Drip, a creator funding platform that Kickstarter had acquired in 2016.

[11] However, in mid-2019, they shut it down before launching and returned the remaining funding to Kickstarter, saying that they could not find a way to sustainably run the business without exposing the creators who would rely on it to too much risk.

[17] Baio was involved in the early dissemination of the Star Wars Kid viral video, which depicted teenager Ghyslain Raza clumsily emulating martial arts moves for the camera.

[18] In response to the negative attention the boy received, Baio and another blogger, Jish Mukerji, organized a fundraiser for Raza which gathered almost $1,000 from about 100 donors.

Baio later said in the documentary Star Wars Kid: The Rise of the Digital Shadows that he had "enormous regret about posting the video."

[21] Baio later received a similar cease and desist letter but refused to comply, citing fair use and decrying what he termed "a special kind of discrimination against amateur creators on the Internet", since Cosby had often been parodied in the mainstream media.