Unemployed with Anna Roisman

This is a safe space for anyone who has ever lost a job, left a job, or is sitting at their desks bored out of their mind right now! Based on the hit live digital talk show, "The Unemployed Show," where Anna and guests would wear pajamas every week and commiserate about bad jobs, this podcast is a more intimate look into the world of unemployment and underemployment. Anna sat in front of a camera on her couch for 'The Unemployed Show' for 2 years and then got a job hosting a show in front of hundreds of thousands of people on the app HQ. Is she the fairy godmother of unemployed millennials? Some say yes! Hopefully this podcast will inspire you to pick yourself up and get a new job, or stay on your couch and chill all day. Either way, you'll laugh with Anna and her guests about the insane things they did for work. Each week Anna interviews friends, comedians, and professionals about their worst (and best!) job stories and how they figured out life as an unemployed person. Oh and sometimes they call a stranger from the internet who is unemployed and in need of a pep talk. It's sweet.

Last refreshed: August 24th, 2025 at 9:25 PM ⓘ

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Episodes

Episode 9: From Lawyer to Late Night Comedian, it's Jess Salomon!

In the latest episode of 'Unemployed,' Anna chats with friend and comedian Jess Salomon (The Tonight Show). Jess was once a war crimes lawyer (gasp!) who decided to pursue her passion and become a comedian. She takes us through a journey of what it was like to leave her job, start going to open mics in Holland, and then having to explain to security at the Canadian border that she and her wife are just heading to the states to hit up some comedy shows. It's a wild ride and you're gonna love it. ...

Feb 12, 2020•54 min

Episode 8: Cookies & Dreams! Becoming An Entrepreneur with Gracie Bensimon

On this special episode of Unemployed, Anna talks to the first entrepreneur of the show, Gracie Bensimon of Gracie Baked! She's a psychologist-turned-professional baker and her cookies are out of this world! We talk about how she always had a love for baking, but wasn't sure if she was gonna take the plunge and start a company. (Thank god she did! We are better for it!) Anna admits to stalking her on Instagram after tasting her cookies and that's how the obsession began! Gracie is a fairly new (...

Feb 04, 2020•37 min

Episode 7: Office Hours In A Bathroom Stall with Jessie Jolles

On this week's episode of Unemployed, Anna chats with her friend and comedian, Jessie Jolles (Betches, No Such Thing As Love) about all of the jobs she had from being a teenage professional organizer and making bank, to sitting in a bathroom stall at a toy company for her personal "office hours." Jessie is a self starter, and iconic freelancer! And if you don't hire her, she will have to report you to her mom, who has an important title in the business bureau of DC, so be chill about it! Also, t...

Jan 28, 2020•41 min

Episode 6: Finding The Silver Lining (even in porn!) with Gabe Gonzalez

On this episode of Unemployed, Anna talks to her friend and phenomenal comedian/host, Gabe Gonzalez. You may know him from the Scruff app, or MTV News... but today? He's unemployed! Gabe and Anna talk about nightmare living situations, his stint producing gay porn, and how his parents found out about that venture! (it's actually unreal) They discuss and fangirl over Eliot Glazer, and how he gave Gabe his first real job in entertainment (spoiler it was on Broad City)!! Gabe is amazing at finding ...

Jan 20, 2020•57 min

Episode 5: From Youtube to Me Time with Akilah Hughes

On the 5th episode of Unemployed, Anna finally properly introduces the show! She chats with her good friend Akilah Hughes, who you may know as the hilarious comedian, creator, and author of "Obviously." They learn about Akilah's job history (of never keeping a job for more than 9 months!!) and how she once impressively received 4 hair products as severance. Akilah and Anna discuss the best ways to take care of yourself in case the world crumbles. And on a positive note, they call "Positive Pat" ...

Jan 14, 2020•50 min

Episode 4: From Late Night Froyo to Late Night TV with Alex Song (and a call to an unemployed stranger-turned-friend)

On this episode of 'Unemployed,' Anna chats with her friend, comedian, TV writer, and former froyo expert, Alex Song! Alex opens up about her experience on 'The Tonight Show with Jimmy Fallon' and what it was like to have periods of unemployment after multiple TV writing jobs, as well as professing her love for her former Pinkberry boss! Anna and Alex also discuss the idea of, 'does everything happen for a reason?' Anna and Alex call a stranger-turned-friend from twitter, Cameron, who got laid o...

Jan 06, 2020•59 min

Episode 3: Navigating Jobs With Your Heart (and a phone call to a stranger!!) with Paul Costabile

On the latest episode of Unemployed, Anna sits down with her friend, also a comedian/host, Paul Costabile. From showing up to a PA job in Staten Island in a full suit (ready to go on camera) to maybe DJ-ing Anna's bat mitzvah(?), Paul has been one of the most hardworking entertainers in town, baby! This is the first episode where Anna and her guest call a stranger who is unemployed and can use a pep talk. Anna and Paul talk to the amazing Christina who lost her job as a baker, and doesn't know w...

Dec 30, 2019•1 hr 2 min

Episode 2: "The Secret Project" (it's Astronomy Club & it rules!) with Keisha Zollar

In this real & raw episode of Unemployed, Anna chats with her friend Keisha Zollar who absolutely CANNOT talk about a TOP SECRET project, lol. (Spoiler alert, but not at all, it's her sketch series on Netflix called "Astronomy Club" and if you haven't watched it, do yourself a favor this holiday season and binge, baby!) Keisha is the queen of "gigging" and "gigged" all over, but really Times Square kept luring her back in. That is, before she became a Television writer. Listen for some incre...

Dec 23, 2019•43 min

Episode 1: A Spiritual Journey Through Jobs (& Club Monaco) with Mike Kelton

This is the first episode of Unemployed with Anna Roisman! Anna talks to her friend, and spiritual guide, Mike Kelton, about all of the jobs he had and went through. From majoring in Musical Theater to becoming a full on sales person at David Barton gym in NYC, this episode has it all! (Except health insurance, cuz, that's tough.) Mike convinces Anna that she has manifested her own jobs, which you can do too! Mike also offers amazing advice to those who are going through unemployed times.

Dec 16, 2019•57 min

Episode 0: Meet Anna, she's been unemployed.

Introducing Unemployed with Anna Roisman. Anna gives you the background of The Unemployed Show and why she's bravely starting a podcast in 2019!! People are still without jobs, and she's here to help! Or here to give you a good laugh in the midst of filling out another cover letter.

Nov 28, 2019•3 min

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