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What's In Your Cart, Josh Gondelman?

Welcome back to What’s In Your Cart, where we ask noteworthy creators, athletes, and celebrities about their favorite products, their shopping habits, and their deal hunting acumen. If you or someone you know would like to be featured, shoot an email at shep@g-omedia.com.com with the subject line “What’s In Your Cart.”

This week, we traded emails with writer and standup comedian Josh Gondelman, who currently serves as supervising producer and writer for Showtime’s Desus & Mero, and is a four-time Emmy award winner for his work on Last Week Tonight with John Oliver. His new book, Nice Try: Stories of Best Intentions & Mixed Results, is out now.

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The Inventory: Do you consider yourself a deal hunter? Do you wait for deals on products that you already decided to buy, or do you buy most products because you saw a deal?

Josh Gondelman: I’m more of a deal sucker. Like, I’m an absolute chump for deals. I don’t always scout around for low prices or wait for price drops (except on flights and jeans) but if I see a thing I’d been considering buying go on sale, it feels to me like fate, and I will be tricked into purchasing it.

The Inventory: What’s the best deal you’ve ever gotten?

Josh Gondelman: I got a pair of Adidas NMD Primeknit sneakers for like 55% off about a year ago. They’re super, super comfortable but they’re kind of expensive. Getting them for that steep discount makes me feel better about wearing them with no socks to walk my dog.

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The Inventory: What’s your favorite place to shop online? How about in person?

Josh Gondelman: My big “shopping” often consists of sneaker purchases, so I’m on StockX a lot, browsing sneakers. And in person there’s a very cool boutique in Brooklyn (with a Manhattan location too) called Rime! Plus, Books Are Magic is my favorite NYC independent bookstore!

The Inventory: What’s the biggest purchase you’ve ever made online? Was it worth it?

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Josh Gondelman: Hmmmm. Recently I was recording a TV appearance across the country, and I had to fly home redeye, so splurged for a business class seat that lies flat so I could sleep a few hours and not have to go into work the next morning after pulling an all-nighter. It cost basically my entire fee from the appearance, but it was worth it to not torpedo my week. Normally I will pay for the cheapest seat and sight bolt upright, but I splurged because this was an exciting opportunity, and I wanted to come back from it feeling as decent as possible.

The Inventory: What’s something you bought recently that really exceeded your expectations?

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Josh Gondelman: I got this fancy dental floss called Cocofloss that I think the writer Emily Gould had recommended online, and it was like $8 which felt ridiculous, but it’s very good and has ruined me for dentist office sample quality floss.

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The Inventory: On the flipside, what was the worst purchase you’ve made recently? Anything you had to return?

Josh Gondelman: I impulse bought a baseball cap with a big pug logo on it that ended up being too small, and then I got the same design a size up which is too big. It’s just a bad fit with this particular style and my shape of head. And the worst part is they sent me two of the smaller size by accident. I’m so bad at returning things, and I think I let the window lapse. So now I have three mostly-unwearable hats.

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The Inventory: What’s the best gift you’ve received recently?

Josh Gondelman: My wife got me a giant custom blanket with my book cover on it, which was so sweet!!!

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The Inventory: I’m curious about your writing setup. What’s on your desk while you’re writing?

Josh Gondelman: At work there’s a lot of clutter. Some books I lent to coworkers that they’ve returned. A coffee mug I never use. A bottle of champagne I received as a gift. A jar of candy that my in-laws got me so that people visit my desk (which is incredibly sweet/sad on my part). At home I don’t write at a desk at all. I lie as horizontal as I can with my laptop on my belly like an otter. It’s the opposite of a standing desk, and it’s how I do my best independent work.

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The Inventory: When you’re on the road doing standup or just traveling for leisure, what are some of the things you always have in your suitcase?

Josh Gondelman: I’m always carrying a book that I may or may not read while I’m away. Plus running shorts that I only ever wear to lounge at the hotel. The aforementioned floss comes with me wherever I go. I may not work out much on the road, but I do not neglect my dental hygiene.

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The Inventory: Do you like to collect credit card points when you shop? What are your go-to cards?

Josh Gondelman: I’m just learning to do this! I think my wife signed us up for a Starwood AmEx, but I’m also so nervous about getting out over my skis in terms of credit and remembering to pay bills, so I prefer to pay cash or use a debit card for things, even though there are benefits to be had by using cards. I’m trying to be more mindful of that!

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The Inventory: Do you subscribe to any physical subscription services? Amazon Subscribe & Save? Meal kits? Wine of the month?

Josh Gondelman: I don’t! I’m not a minimalist, but I am bad at receiving gifts, in that if it’s not something I already wanted, I will not use it no matter how good it is a lot of the time. So signing myself up for a subscription service seems like enrolling in a shelf-cluttering delivery program.

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The Inventory: What are three items that you couldn’t live without?

Josh Gondelman: A Physical paper datebook because the layout helps me figure out where the hell I’m supposed to be. Headphones because I can’t read when I’m commuting. And glasses, because without them I’d fall down an elevator shaft and literally die.

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The Inventory: What’s something you buy a lot of that might seem strange to an outside observer?

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Josh Gondelman: I’m a Dunkin’ Donuts year-round iced coffee loyalist, which some people look down their nose at. My destiny is to be one of those old guys just talking shit at a Dunkin’ for three hours every morning before anyone else in town is even awake.

The Inventory: Are there any items that you want to buy, but just can’t pull the trigger on? Anything you keep abandoning in your cart?

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Josh Gondelman: There is one pair of Adidas Ultraboost shoes that was made in a very limited run that I’ve coveted for years. I have a similar pair that I like a lot, but slightly less. I frequently look longingly at them before closing my browser window.

The Inventory: What are the last three items in your Amazon order history?

Josh Gondelman: Dianetics (for a podcast I was appearing on where we talked about it), ConAir for rent online (same reason), and a preorder for my friend Rachel Wilkerson Miller’s upcoming book The Art Of Showing Up.

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The Inventory: And finally, what are the last three items in your Amazon browsing history that you didn’t end up buying?

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Josh Gondelman: Humiliatingly, it’s links to my own book and albums because I was collecting them to tweet or hyperlink to somewhere. I don’t do a ton of browsing on Amazon. I try to buy locally if I can, and I’m also not a big shopping browser. I’m pretty surgical in-and-out unless I’m looking for a specific item of clothing (a new cardigan, dress shirt) for a specific occasion.


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About the author

Zach Custer

Senior Director, Affiliate Partnerships & Commerce Strategy

Shep McAllister

Senior Director of Commerce | Send deal submissions to deals@gizmodomedia.com

Jolie Kerr

Jolie Kerr is a cleaning expert, advice columnist and the host of the podcast Ask a Clean Person