[1] The show has appeared on the iTunes podcast charts in multiple countries, reaching number 3 in the United States.

The show has featured several guest stars, including CollegeHumor co-founder Ricky Van Veen,[3] actors and comedians Ben Schwartz[4] and Thomas Middleditch,[5] actresses Allison Williams[6] and Rose McIver,[7] co-workers Streeter Seidell,[8] Emily Axford,[9] Sarah Schneider,[10] Brian K. Murphy,[11] Patrick Cassels, and Dan Gurewitch,[12] The Pete Holmes Show host Pete Holmes,[13] rappers Hoodie Allen[14] and Lil Dicky,[15] singer Alana Haim,[16] Jake's mom Laura Hurwitz, and his brother Micah Hurwitz, all of whom were present for entire episodes, as well as cancer sufferer Ethan Trex[17] and Amir's (at the time) girlfriend Laura,[18] who were only in parts of an episode.

[22] The Guardian's Miranda Sawyer called If I Were You "a typical example of a comedy podcast" and "amiable enough", but said it contained "far too much laughing", commenting that "If I wanted stream-of-consciousness waffle with the occasional funny line, I'd listen to [my small children].

"[23] Sam Tabachnik of The Washington Post has written of the podcast that Jake and Amir "have their fingers firmly on the pulse of the digital comedy scene," and "riff off each other with ease,"[24] while The Concordian's Kayla Culver described it as "comfortable to listen to" and "genuinely funny," "like listening to two best friends having a hilarious conversation on the couch next to you.

As announced on Episode 146, IIWY show left PodcastOne and is now available on radio and podcast website, Spreaker.