Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!

Inside Darren Carter's Laugh Factory Slot 19 Strategy Comedian Darren Carter joins Sarah Halstead and Rich Chassler for a coffee-fueled masterclass on building a stand-up career in the social media age. Carter pulls back the curtain on nearly four decades of comedy, from his Fresno forensics team days to headlining the Laugh Factory, Comedy Central, The Tonight Show with Jay Leno, and booking a Showtime special after landing a Miller Beer national commercial as only his third audition. The trio dives into his headshot story (shot by a Fresno photographer who drove a van down to LA to shoot sets), the strategic genius of always choosing slot #19 at the Laugh Factory Tuesday Night Live, the power of voices and impressions, and his daily social media workflow using iMovie and CapCut, including the secret weapon of trial reels. Along the way Carter shares the legendary Minnie Pearl advice he keeps in his Notes app: "Love them with your heart and they'll love you right back." It's a joyful, generous, hilarious hour that feels like pulling up a bar stool with three working comedians. Today we're drinking coffee. Guest Info Darren Carter is a stand-up comedian, actor, and podcaster based in Sherman Oaks, California. He's performed on The Tonight Show with Jay Leno, Comedy Central, and booked a Showtime special. On screen, he's starred opposite John Travolta. Off stage he's a family man and the host of the podcast Pocket Party. Carter started comedy in his hometown of Fresno in 1989, sharpened his chops in high school forensics (Dramatic Interpretation, Humorous Interpretation, Original Prose & Poetry, and Speech to Entertain, plus the dreaded Lincoln-Douglas debate), took a Variety Arts class at Fresno City College, then moved to LA. He's a paid regular at both the Comedy Store and the Laugh Factory, and he's cracked the social media consistency code with daily uploads across Instagram, TikTok, and YouTube. Guest Social Links Instagram  @officialdarrencarter … https://www.instagram.com/officialdarrencarter/  Linktree … https://linktr.ee/DarrenCarter  YouTube …http://youtube.com/DarrenCarter  TikTok … https://www.tiktok.com/@officialdarrencarter Facebook … https://www.facebook.com/DarrenCarterOfficialFanPage?mibextid=ZbWKwL  Pocket Party on Apple Podcasts … https://podcasts.apple.com/us/podcast/darren-carter-pocket-party/id1373544111?mt=2  Drink of the Podcast (NOT SPONSORED) We just really like this brand of Organic Mushroom Coffee.  Six adaptogenic mushrooms, no jitters, medium price-tier subscription. Hosts Sarah and Rich are drinking it because the guest requested coffee. This is the first time DDBH has gone caffeine-fueled instead of wine-fueled, and the conversation is no less intoxicating. Carter ordered a vanilla iced latte alongside. "It doesn't give me the jitters like regular coffee… but you'll go broke drinking it." - Rich Chassler Ryze Mushroom Coffee … https://www.ryzesuperfoods.com/pages/shop-all?srsltid=AfmBOorKrz2kUh7SB0UHHxzGUhyMObP4iM5xah2BxPOo3xJ0YMdSxYXr  Chapters 0:00 Cold Open & Welcome, Sarah & Rich kick off the show 1:00 The Drink Today: Organic Mushroom Coffee, adaptogens, ~$54/mo, no jitters 4:16 Introducing Darren Carter, Tonight Show, Comedy Central, starred opposite John Travolta 4:40 The Headshot Story, photographer Frankie Lee L driving down from Fresno to shoot LA open-micers 11:00 Beginners Luck vs Inherent Energy, does your excitement get you the room? 13:00 Social Media Routine, daily uploads, 90-second reels, the magic of trial reels (1 to 5/day) 17:51 Editing Workflow, iMovie to phone to CapCut Pro: bright, loud, watermarked 24:00 New Bits vs Old Material, "Think of the room like an art gallery: today I'm putting up Darren Carter 2026." 29:00 Repackaging Old Footage, combine two days, add a GIF, change the hook, fool the algorithm 31:00 Bar vs Belly Room Productivity, 1992 vs 2026 (Barry Katz: "Nothing good happens on the couch") 33:00 Selling Tickets in 2026 vs The Old Days, when clubs had phone-banking teams, radio hits, the Last Laugh in San Jose 36:08 Comedy Origins in Fresno, career day, forensics team (DI, HI, OPP, STE, Lincoln-Douglas debate) 42:00 Moving to LA & Laugh Factory Tuesday Night Live, meeting roommate Julian Jones, the slot-19 strategy 45:10 The Power of Voices & Impressions, Bart Simpson, Snagglepuss, Gangs of Nebraska, Danny Lobell's Jackie Mason 49:00 Breaking Big, Miller Beer commercial (3rd audition, 1995), SAG card, Showtime special, Comedy Store + Laugh Factory regular 51:30 "Love Them With Your Heart," the Minnie Pearl advice that changed his stage life 53:16 A Long Beach Lesson in Professionalism, never call out the crowd (the bringer-caller tanked his set) 54:20 Pocket Party + Where to Find Darren, Instagram, Linktree, YouTube, TikTok 55:28 Shoutouts, Bass Home Studios / Doug Bass (plugs for anyone wanting a podcast space), Riedel Glassware, Corey Fry 57:00 Sign-Off, like, subscribe, five stars, see you next week Call to Action If you dug this episode, do these four things right now: LIKE this video ... https://www.youtube.com/@DrinkingDuringBusinessHours  SUBSCRIBE to Drinking During Business Hours on YouTube... https://www.youtube.com/@DrinkingDuringBusinessHours  FIVE-STAR the podcast on Apple Podcasts & Spotify COMMENT below your favorite Darren Carter moment (or just say hi, we read every one) Thinking about starting your own podcast? Hit up Doug Bass at Bass Home Studios in the West Hollywood-adjacent area. As Darren said: "There's a restroom, plenty of parking, and it's great." Yes, we got a shoutout for the air conditioning, the parking, and the bathroom. DDBH appreciates you, Doug. Host Links 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 📧 [email protected] 🎧 Please rate & review the podcast on your favorite platform — it helps more than you know!   #darrencarter #DrinkingDuringBusinessHours #DDBH #StandUpComedy #ComedyLife #Comedian #ComedyPodcast #LAComedy #NYCComedy #ComedyStore #LaughFactory #TonightShow #ComedyCentral #Showtime #PocketParty  

She Did Fallon While Raising Twin Boys?! | Jessica Keenan on Comedy, Motherhood & Chaos In this episode of Drinking During Business Hours, Sarah Halstead and Rich Chassler welcome comedian, writer, actress, mother, and now homeowner Jessica Keenan for a hilarious and refreshingly honest conversation about stand-up comedy, motherhood, ambition, marriage, wine, and trying to keep your identity intact while juggling all of it. The episode opens with a playful conversation about launching the show on YouTube, dealing with comments online, and a passionate breakdown of the featured wine before the hosts bring Jessica into the mix. Once Jessica joins the conversation, the episode quickly becomes one of those classic Drinking During Business Hours hangs where funny stories and real talk bounce off each other effortlessly. Jessica talks about recently moving closer to the clubs after years of brutal driving, her husband's finance job at a wire manufacturing company, her roots in Las Vegas, and how speech and debate helped shape the performer she would eventually become. She also gets into how she fell in love with stand-up, why classes helped her commit to the craft, and how chasing that first great set feels a lot like gambling.  The conversation gets even richer when Jessica opens up about being a comedian with identical twin boys, balancing life on the road with motherhood, and how comedy fits into family life. Sarah, Rich, and Jessica also dive into the realities of women in comedy, late-night TV pressure, outfit panic before The Tonight Show Starring Jimmy Fallon, hair and makeup anxiety, true crime obsession, sleep habits, and the strange overlap between ambition and everyday chaos. It is funny, candid, and full of the kind of chemistry that makes this podcast feel like being at the table with them.  Guest Info Jessica Keenan is a stand-up comedian, writer, and actress who has performed in high-profile comedy rooms across Los Angeles and beyond. In this episode, Sarah and Rich talk with Jessica about her comedy journey since starting stand-up in 2012, her background in speech and debate, her experience performing on The Tonight Show Starring Jimmy Fallon, and what it means to stay active and relevant in comedy while raising young twin boys.  Jessica comes across as sharp, self-aware, grounded, and seriously funny. She talks openly about the hustle of the business, the importance of balance, and why she never wanted comedy to become the kind of life that prevented her from actually living. That perspective gives this episode a really strong center beneath all the jokes. Guest Social Links Jessica Keenan … https://www.jkeenancomedy.com/ Instagram: @jkeenancomedy … https://www.instagram.com/jkeenancomedy/?hl=en Website: jkeenancomedy.com … https://www.jkeenancomedy.com/  Drink of the Podcast Sangiovese from Tuscany, Italy This week's featured wine is a Sangiovese from Tuscany, Italy. Sarah describes it as transparent in color, Pinot Noir-like at first glance, but unmistakably Sangiovese once you taste it and see the orange rim. She highlights its beautiful red fruit profile, darker brooding undertones from age, and the fact that it works both with food and on its own. The hosts even joke that it is light enough to enjoy with an ice cube by the pool. The producer and vintage are not stated in the episode.  Chapters 00:00 Welcome back and YouTube channel shoutout 01:56 The reality of comments, haters, and playing to camera 02:08 Wine intro: Sangiovese from Tuscany, Italy 03:50 Why good bottles should be opened now, not saved forever 04:35 Introducing Jessica Keenan 08:14 Moving closer to the clubs and years of brutal LA driving 09:48 Jessica's husband, finance, and the mysterious smell of wire 15:24 Comedy rooms, lineups, and women in stand-up 15:38 How Jessica got started in stand-up and speech/debate roots 26:04 Motherhood, identical twin boys, and balancing comedy with family life 35:03 Marriage, dating comics, and finding the right partner 35:13 Jessica's Tonight Show with Jimmy Fallon story 39:11 The pressure of outfits, hair, makeup, and late-night TV presentation 48:44 Sleep habits, meditation music, and true crime at bedtime 54:43 Twin boys, attention, and whether the kids inherited the funny 57:43 Where to follow Jessica, Sarah, Rich, and subscribe to the show's YouTube  Call to Action If you loved this episode, make sure you subscribe to the Drinking During Business Hours YouTube channel, give the episode a thumbs up, and leave a comment telling Sarah and Rich what you thought preferably a good one, as they jokingly note at the top of the episode. You can also follow Jessica Keenan on Instagram and keep up with her live dates on her website.  If this episode hit for you, share it with a friend who loves stand-up comedy, parenting chaos, late-night TV stories, wine talk, and unfiltered conversations.  FOLLOW US ON SOCIALS! YouTube Channel: https://www.youtube.com/@DrinkingDuringBusinessHours 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 📧 [email protected] 🎧 Please rate & review the podcast on your favorite platform — it helps more than you know!     #DrinkingDuringBusinessHours  #JessicaKeenan #JKeenanComedy #SarahHalstead #RichChassler  #ComedyPodcast  #StandUpComedy #WomenInComedy#MomComedian #TwinMom  #JimmyFallon #TonightShow #WineAndComedy #YouTubePodcast #ComedianInterview