Jake and Amir

In 2013, Jake and Amir started the podcast, If I Were You, an advice show where listeners email in questions which are answered in a humorous way.

[1] Running for over eight years, Jake and Amir was CollegeHumor's longest-running series and has amassed approximately one-billion views as of April 2017.

[6][7] The pair returned with another video on March 31, 2020 on their HeadGum channel in the midst of the Coronavirus pandemic with a skit about Amir's social distancing ideas.

In December 2013, Deadline reported that Jake and Amir were being brought on by TBS to star in a comedy directed by Ed Helms.

[10][2] When news came in February 2015 of Jake and Amir's departure from CollegeHumor, fans pushed for TBS to pick up the production with the Twitter trending campaign #GreenLightJakeandAmir.

[18][better source needed] In May 2013, Jake and Amir started the podcast If I Were You as an advice show where they take listener questions and try to answer them in a helpful but funny way.

[19][20] Jake said that If I Were You was partially inspired by the NPR show Car Talk, in that their audience listens for the banter between the two hosts, not necessarily the questions themselves.

"[2] More than that, Jake says that he enjoys reaching out to "nerdy" younger fans because they can act as role-models to show that their best days are ahead of them: "We're like a little beacon of hope for losers that are told they're gonna be cool in ten years.

[23] On August 1, 2015, after leaving CollegeHumor, Jake and Amir founded a podcast network named HeadGum with their friend Marty Michael.

The podcast description reads:[27] Jake and Amir host a constantly changing show that re-invents itself multiple times per episode.