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Drinking During Business Hours with Sarah Halstead and Rich ChasslerWhere comedy & fine wine meet! Author: Sarah Halstead
Comedians Sarah Halstead and RIch Chassler talk with a diverse lineup of creatives about their life's journey, passions, and what may lead them to drink during business hours. Language: en Genres: Arts, Comedy, Performing Arts Contact email: Get it Feed URL: Get it iTunes ID: Get it Trailer: |
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How Ben Gleib Reinvented Late Night on YouTube, Went Viral in Political Debate, and Helped Save Comedy During COVID
Episode 106
Monday, 4 May, 2026
How Ben Gleib Reinvented Late Night on YouTube, Went Viral in Political Debate, and Helped Save Comedy During COVID Hosts Sarah J. Halstead and Rich Chassler welcome comedian, creator, and disruptor Ben Gleib for a fast, funny, and surprisingly thoughtful conversation about career pivots, political courage, crowd work, and building comedy for a new era. Ben opens up about overcoming a childhood speech challenge, creating connection through stand-up, and why he's always pushed beyond the expected lane. The conversation moves from live comedy and dating confidence to the deeper purpose behind making people laugh. This episode also dives into some of Ben's biggest career swings, including his viral Charlie Kirk debate, the launch of Nowhere Comedy during the pandemic, and his newest ambition: Good Night with Ben Gleib, a digitally native late-night show built for YouTube. It's a sharp, hilarious look at what happens when a comic combines talent, activism, and entrepreneurial instinct to build what traditional entertainment wouldn't hand him. Guest Info Ben Gleib is a stand-up comedian, TV host, and creator known for sharp crowd work, high-energy storytelling, and building projects that sit at the intersection of comedy, media, and culture. In the episode, he discusses his work on Idiotest, his long path toward becoming a late-night host, his co-founding of Nowhere Comedy during COVID, and his launch of Good Night with Ben Gleib, a YouTube-first late-night show designed for a global interactive audience. Follow Ben Ben Gleib Website … https://www.bengleib.com/ Ben Gleib on Instagram … https://www.instagram.com/bengleib/ Ben Gleib on X … https://x.com/bengleib Ben Gleib YouTube … hhttps://www.youtube.com/@bgleib Nowhere Comedy Club … https://www.nowherecomedyclub.com/ Good Night with Ben Gleib … https://www.youtube.com/@goodnight/videos 🍷 Featured Beverage Riondo de-alcoholized sparkling wine a de-alcoholized bubbly the hosts use to kick off a fun conversation about the difference between non-alcoholic wine and de-alcoholized wine. Chapters Chapter timings below are adapted from the episode audio and your supplied outline. 00:00 Welcome + de-alcoholized wine vs. non-alcoholic wine 03:13 Meet Ben Gleib 05:00 Why great conversations deserve to be recorded 08:45 Dating, confidence, and being "cool" 13:15 Comedy, politics, and speaking your mind 16:28 The Charlie Kirk debate and going viral 23:27 Building Nowhere Comedy during COVID 31:30 Entrepreneurship, creativity, and doing "too much" 34:35 Childhood speech struggles and finding his voice 36:50 Crowd work, comedy instincts, and serving the audience 42:10 Old material, new material, and comedy philosophy 50:45 Ben's biggest new project yet 52:28 Reinventing late night for YouTube 55:25 Where to find Ben and what's next 🎙️ Hosts 📧 drinkingduringbusinesshours@gmail.com 🎙️ Listen on Apple Podcasts 🎧 Loving the show? Please rate and review on your favorite platform. Every single review helps us reach more listeners. FOLLOW US ON SOCIALS! Sarah IG @sarahhalstead https://www.instagram.com/sarahhalstead/?hl=en FB @sarahjhalsteadcomic https://www.facebook.com/sarahjhalsteadcomic/ X @sarahjhalstead https://twitter.com/sarahjhalstead Website @SarahHalstead | sarahjhalstead.com Rich IG @richchassler https://www.instagram.com/richchassler/ FB @chasslerfans https://www.facebook.com/Chasslerfans/ X @richchassler https://x.com/richchassler Website richardchassler.com 📧 drinkingduringbusinesshours@gmail.com 🎧 Please rate & review the podcast on your favorite platform — it helps more than you know! #DrinkingDuringBusinessHours #BenGleib #ComedyPodcast #LateNightTV #YouTubeComedy #StandUpComedy #CrowdWork #NowhereComedy #PoliticalComedy #PodcastShowNotes
