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

Keith Reza on Comedy, Fame, and Never Giving Up

This week on Drinking During Business Hours, Sarah Halstead and Rich Chassler sit down with comedian, actor, writer, and podcaster Keith Reza for a funny, candid, and inspiring conversation about building a career in comedy, staying persistent in entertainment, and carving out your own voice in a brutally competitive business.

With roots in stand-up, a long-running podcast of his own, and years spent learning from the legendary Norm Macdonald, Keith brings the kind of behind-the-scenes perspective comedy fans love.

From the grind of live comedy to storytelling, podcasting, industry survival, and the mindset it takes to keep going, this episode is a great listen for comics, creators, and anybody chasing a creative life. If you love conversations about stand-up, entertainment, mental resilience, and the reality behind making it, this one belongs on your watchlist.

🎤 Guest Info

Keith Reza is a stand-up comedian, actor, writer, and podcast host with more than 20 years in comedy. He was diagnosed with Asperger's Syndrome at 13 and found comedy as a way to connect with people and navigate the world. He was mentored by Norm Macdonald for nine years, contributed as a writer on Norm Macdonald Has a Show and Norm Macdonald Live, has appeared on NBC, Animal Planet, and Netflix Is A Joke, and released the special Keith Reza: Make It Happen. He also hosts the long-running celebrity interview podcast Reza Rifts.

🔗 Guest Social Links

• Website: https://www.keithreza.com/

• Instagram: https://www.instagram.com/keithreza/

• Facebook: https://www.facebook.com/realkeithreza

• X / Twitter: https://www.twitter.com/keithreza

• TikTok: https://www.tiktok.com/@keithreza

• YouTube: https://www.youtube.com/channel/UCpyRbdbee3pBlDrtMDd6Pww

• Podcast - Reza Rifts: https://www.keithreza.com/gallery

🍷 Drink of the Podcast

Drink of the Podcast: Molto Bene Mocktails

Whether it's wine, cocktails, or something unexpected, the drink always sets the tone on Drinking During Business Hours, where comedy, conversation, and happy hour energy always meet in the middle.

⏱️ Chapters

00:00 Intro to Keith Reza

02:15 Keith's comedy journey

06:40 Learning from Norm Macdonald

11:05 Writing, performing, and finding your voice

16:20 The reality of stand-up life

22:10 Hosting Reza Rifts

28:35 Comedy, resilience, and mental toughness

35:00 Entertainment industry lessons

42:25 What keeps comedians going

49:10 Final thoughts and where to follow Keith

📣 Call to Action

If you enjoyed this episode, make sure you like, comment, and subscribe to Drinking During Business Hours for more conversations with comedians, actors, writers, and creatives from across entertainment and culture.

Drop a comment with your favorite Keith Reza moment and share the episode with someone who loves stand-up comedy, podcasts, and behind-the-scenes industry stories.

🥂 Host Links

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!

Follow the podcast here: 🍷 Apple Podcasts: Drinking During Business Hours ,,, https://podcasts.apple.com/us/podcast/drinking-during-business-hours-with-sarah-halstead/id1273935631

Watch it on YouTube ... https://www.youtube.com/@Sarahhalsteadcomedian

#KeithReza #StandUpComedy #Podcasting #ComedyPodcast #DrinkingDuringBusinessHours #SarahHalstead #RichChassler #ComedianLife #EntertainmentPodcast #PodcastGuest #ComedyJourney #CreativeLife #NormMacdonald #JohnCusack #SuccessMindset

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:

1. LIKE this video ... https://www.youtube.com/@DrinkingDuringBusinessHours

2. SUBSCRIBE to Drinking During Business Hours on YouTube... https://www.youtube.com/@DrinkingDuringBusinessHours

3. FIVE-STAR the podcast on Apple Podcasts & Spotify

4. 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

David Leaf on Brian Wilson, SMiLE & The Beach Boys

In this episode of Drinking During Business Hours, Sarah Halstead and Rich Chassler welcome back acclaimed writer, filmmaker, and UCLA professor David Leaf for a funny, wide-ranging, and surprisingly moving conversation about music, storytelling, teaching, and his deeply personal friendship with Brian Wilson. What starts with mocktails and comedy banter turns into a fascinating behind-the-scenes look at Pet Sounds, SMiLE, The Beatles, and what it really means to devote your life to great art.David shares how he moved to Los Angeles determined to write about Brian Wilson, how that dream eventually led him into Wilson's inner circle, and why helping bring SMiLE back to life became one of the defining missions of his career. He also talks about teaching legendary UCLA music courses, the "four Ds of success," documentary filmmaking, movie scores, and why the emotional power of music matters more than technical theory.

Guest Info

David Leaf is an award-winning writer, director, producer, and one of the most respected chroniclers of The Beach Boys and Brian Wilson. He is the author of The Beach Boys and the California Myth, God Only Knows, and SMiLE: The Rise, Fall & Resurrection of Brian Wilson. He also teaches at UCLA, where he leads acclaimed classes on The Beatles, songwriting, and music documentaries.

Guest Social Links

• Website: leafprod.com

• Instagram: @davidleafwriter

• Facebook: David Leaf

Drink of the Podcast

Molto Bene Ginger Beer Mocktail Sarah and Rich sip an alcohol-free mocktail built around Molto Bene ginger beer, while also shouting out San Benedetto, the Italian water brand behind it. They discuss why they love alcohol-free options, sparkling water, and beverages with no sodium making this one of the more mocktail-forward episodes of the show.

Chapters

00:58 What they're drinking: Molto Bene ginger beer mocktails

04:59 Introducing return guest David Leaf

06:33 California drought talk, comedy, and desert living

09:42 David on life, relationships, and long engagements

11:39 Teaching at UCLA and why students don't read

18:54 The Beatles, Yoko Ono, and music storytelling

20:15 David's move to L.A. to write about Brian Wilson

22:16 The accidental rise of The Beach Boys

24:03 David's "four Ds of success"

27:20 Movie scores, composers, and how music shapes film

31:43 David's new book: SMiLE: The Rise, Fall & Resurrection of Brian Wilson

35:15 Pet Sounds, Good Vibrations, and the collapse of SMiLE

41:54 Helping Brian Wilson finally complete SMiLE

48:40 Writing process, oral history, and preserving music history

55:08 Where to find David Leaf online

59:14 Host plugs, thank-yous, and sponsor shout-outs

Call to Action

If you loved this episode, make sure to like, comment, subscribe, and share Drinking During Business Hours on YouTube. Follow Sarah Halstead, Rich Chassler, and David Leaf for more comedy, music stories, behind-the-scenes entertainment talk, and future episodes with incredible guests. And if you're a fan of Brian Wilson, The Beach Boys, The Beatles, or great music documentaries, this is an episode you'll want to revisit.

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!

Podcast

• Apple Podcasts: Drinking During Business Hours

• Spotify: Drinking During Business Hours

#DavidLeaf #BrianWilson #TheBeachBoys #SmileAlbum #PetSounds #TheBeatles #SarahHalstead #RichChassler #MusicHistory #ComedyPodcast #EntertainmentPodcast #RockAndRoll #PodcastClips #YouTubePodcast

Lesley Wolff on Hollywood Casting, Comedy & Acting Careers

In this episode of Drinking During Business Hours, Sarah Halstead and Rich Chassler sit down with casting director, producer, teacher, comedian, and actor Lesley Wolff for a fast, funny, insider-heavy conversation about casting, stand-up, commercials, creative survival, and how the entertainment business really works. The episode starts over a Michigan rosé and quickly turns into a candid, hilarious talk about commercial auditions, stage moms, acting insecurity, networking, comedy culture, and why visibility can matter as much as talent in Hollywood.

Lesley also opens up about her long career developing comedy talent, her Fresh Faces workshop philosophy, and her frustration with gatekeeping in entertainment. One of the most interesting parts of the episode is her discussion of AI, digital casting, and the future of the business — especially how creators, actors, and comedians may need to adapt to a much more self-generated, tech-driven industry. Funny, brutally honest, and packed with useful perspective, this episode is a great listen for comics, actors, casting nerds, and anyone trying to make a living in entertainment.

Guest Info

Lesley Wolff is a casting director, actress, comedy mentor, and founder of the Fresh Faces Stand-Up Comedy Workshop. Public profiles describe her as a longtime talent developer and "Comic Fluffer," with acting credits including Weeds, The George Lopez Show / Lopez, No Way Jose, and Guest House, plus work in digital, TV, film, and comedy development.

Her background also includes TV writing, comedy production, and talent development across multiple lanes of entertainment. VoyageLA notes that she wrote for ABC's Recess and Sweet Valley High, produced comedy showcases featuring major names, and built Wolff Casting as a boutique casting company with a strong digital and comedy focus.

Guest Social Links

Instagram: @lesleywolffisthephotobomb … https://www.instagram.com/lesleywolffisthephotobomb/?hl=en

Website: wolffcasting.com … http://wolffcasting.com/ Email: [email protected] IMDb: Lesley Wolff … https://www.imdb.com/name/nm1078298/

VoyageLA … https://voyagela.com/interview/meet-lesley-wolff-castingfresh-faces/

Drink of the Podcast

This episode features a Michigan rosé from Achrimère Wines in Traverse City, made by Aimee Desautels. In the episode, Sarah describes it as a female-owned Michigan wine with a creamy mouthfeel and red-fruit notes, while the group riffs on rosé, wine education, and how fun it is to discover bottles outside the usual Napa/Bordeaux lane.

Chapters

00:48 Today's drink: Michigan rosé from Achrimère Wines

02:31 Introducing Lesley Wolff

05:42 Commercial casting, beginner's luck, and stage mom energy

10:20 Acting vs casting and why commercials are their own skill

14:35 Audition psychology, networking, and "talent" myths

19:30 Casting power, director callbacks, and how jobs really get decided

20:52 Lesley's new casting venture and cutting through gatekeeping

24:10 AI, self-tapes, digital likeness, and the future of casting

31:45 Romanticizing the old acting world vs today's business

34:45 How Sarah and Rich met in the improv parking lot

39:00 Comedy community, mentors, Brody, Mitch Hedberg, and support systems

47:00 Joke writing vs personal storytelling in stand-up

52:20 Dying on stage, producing shows, and building audience trust

57:00 Why artists can't quit, and what success really means

Call to Action

If you enjoyed this episode, make sure you like, comment, and subscribe to Drinking During Business Hours on YouTube. Share this episode with an actor, comic, casting friend, or anyone obsessed with how Hollywood actually works and drop your favorite Lesley Wolff moment in the comments.

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!

Podcast

Apple Podcasts: Drinking During Business Hours … https://podcasts.apple.com/us/podcast/drinking-during-business-hours-with-sarah-halstead/id1273935631

YouTube: @DrinkingDuringBusinessHours … https://www.youtube.com/@DrinkingDuringBusinessHours

#LesleyWolff #SarahHalstead #RichChassler #ComedyPodcast #CastingDirector #HollywoodCasting #FreshFaces #ActingPodcast #StandUpComedy #EntertainmentIndustry #FreshFaces #CommercialActing #YouTubePodcast #AIinEntertainment

Mateen Stewart Gets Real on Comedy, Rejection & Bigger Doors

In this episode of Drinking During Business Hours, Sarah Halstead and Rich Chassler welcome comedian, actor, and producer Mateen Stewart for a hilarious and wide-ranging conversation over BuzzBox cocktails. The episode kicks off with sports fandom, Detroit pride, Knicks talk, and the emotional damage of being a lifelong Lions fan before shifting into Mateen's path through acting, theater, summer camps, and eventually stand-up comedy.

As the conversation unfolds, Mateen shares how a simple goal to try three minutes at an open mic turned into a full comedy career, along with stories about comedy classes, bringer shows, ticket-selling pressure, and the strange realities of the stand-up business. Sarah, Rich, and Mateen also dig into what makes comedians relatable, why life experience matters on stage, and how the industry keeps changing with streaming, social media, and audience habits.

The episode lands on a personal and inspiring note when Mateen talks about losing his mother, the wisdom she gave him, and how her phrase "Bigger Doors" became the title of his special. Funny, honest, and packed with insight about show business, persistence, and creative life, this is a great episode for comedy fans, entertainers, and anyone trying to build a career in the arts.

Guest Info

Mateen Stewart is a Detroit-born stand-up comedian and actor who studied theater at Florida A&M University. Public sources credit him with screen appearances tied to Last Week Tonight with John Oliver, Jimmy Kimmel Live!, and acting credits including Comics Unleashed, Comedy Parlour Live: Quarantine Edition, The Devil Comes to Kansas City, and NTSF:SD:SUV::. In the episode, Mateen also plugs his special Bigger Doors, available on YouTube.

Guest Social Links

Instagram: @mateenstewart … https://www.instagram.com/mateenstewart/ X / Twitter: @MateenStewart … https://x.com/MateenStewart Facebook: Mateen Stewart Comedy … https://www.facebook.com/mateenstewartcomedy/ Linktree: linktr.ee/mateenstewart … https://linktr.ee/mateenstewart

Drink of the Podcast

This episode features BuzzBox premium ready-to-drink cocktails, starting with a Vodka Cranberry, then moving to Whiskey Lemonade, and finishing with the Mardi Gras Hurricane. Sarah and Rich describe the boxed cocktails as recyclable, portable, and surprisingly strong with a shoutout to Kevin from BuzzBox for supplying the drinks.

Chapters

00:00 Welcome back to Drinking During Business Hours

01:30 BuzzBox cocktails and what everyone is drinking

03:22 Introducing Mateen Stewart

03:35 Detroit sports, Knicks fandom, and Lions heartbreak

09:30 Summer camps, Long Island, and counselor life

17:32 From acting auditions to discovering stand-up comedy

21:50 Comedy classes, bringer shows, and first stage highs

27:47 Success, comedy credits, and industry respect

30:20 Bad networking, comedy etiquette, and checking in with the host

35:10 Social media, ticket sales, and the changing stand-up business

40:20 Third cocktail pour and Mateen's theater background

42:55 Wedding DJing, officiating, and using life in comedy

46:15 Losing his mother and the meaning behind Bigger Doors

50:45 Writing scripts, pitching projects, and handling rejection

55:20 Detroit loyalty, LA life, and hometown identity

57:55 Where to find Mateen and upcoming road dates

59:10 Final thank-yous, plugs, and outro

Call to Action

If you enjoyed this episode, be sure to like, comment, and subscribe to Drinking During Business Hours on YouTube. Share the episode with a comedy fan, drop your favorite Mateen Stewart moment in the comments, and follow Sarah and Rich for more funny, unfiltered conversations with comics, creatives, and culture people over a drink or two.

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!

Podcast

Apple Podcasts: Drinking During Business Hours … https://podcasts.apple.com/us/podcast/drinking-during-business-hours-with-sarah-halstead/id1273935631

YouTube: @DrinkingDuringBusinessHours … https://www.youtube.com/@DrinkingDuringBusinessHours

#DrinkingDuringBusinessHours #MateenStewart #SarahHalstead #RichChassler #ComedyPodcast #StandUpComedy #ComedianInterview #BiggerDoors #PodcastClips #EntertainmentPodcast #FunnyPodcast #YouTubePodcast #DetroitComedian #HollywoodComedy #CreativeLife

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

We Launched Our YouTube Channel | Comedy, Champagne, New York Stories & Married Life

In this episode of Drinking During Business Hours, Sarah Halstead and Rich Chassler catch up on everything happening behind the scenes from the launch of their new YouTube channel to comedy shows, New York stories, burnout, voting, marriage, taxes, and of course, what they're drinking.

Over a bottle of Andre Delorme Blanc de Blanc, the conversation bounces from hilarious married-host banter into a genuinely interesting deep dive on sparkling wine, including champagne history, aging on the lees, riddling bottles, and why "brut" may have gotten its name. From there, Sarah and Rich talk about the evolution of the podcast, what audiences want more of, the pressure of nonstop content creation, and why they're trying to slow down a little this month.

They also recap Rich's New York trip, awkward run-ins with social media comics, upcoming comedy plans, a Byron Allen premiere party, and their appreciation for the comedy community. Funny, loose, and personal, this episode is classic Drinking During Business Hours: wine, comedy, culture, and real-life chaos.

Drink of the Podcast

Andre Delorme Blanc de Blanc A sparkling Burgundy made from 100% Chardonnay.

This bottle Is a standout alternative to champagne and talk about Sparkling Burgundy vs. Champagne:

• Aging on the lees

• Brioche / baked bread notes in sparkling wine

• Exploding bottles in early champagne production

• Riddlers, disgorgement, and Madame Clicquot

• The folklore behind the word brut

Chapters

00:00 Welcome back + married-host banter 02:23 Big news: the DDBH YouTube channel is live 02:33 Drink of the episode: Andre Delorme Blanc de Blanc 04:10 Sparkling Burgundy vs. Champagne 05:40 What "aging on the lees" actually means 07:35 Madame Clicquot and the evolution of champagne 08:37 The story behind the word "brut" 09:59 How much wine talk do listeners really want? 12:09 Sarah's champagne dinner in Beverly Hills 12:57 What kind of content do listeners want more of? 17:04 Why launching the podcast on YouTube matters 19:28 Rich's New York trip and headlining Rodney's 20:17 Social media comics vs. real-life comedy culture

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Sarah

IG @sarahhalstead https://www.instagram.com/sarahhalstead/?hl=en

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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

🎧 Please rate & review the podcast on your favorite platform — it helps more than you know!

Drinking During Business Hours Apple Podcasts: https://podcasts.apple.com/us/podcast/drinking-during-business-hours-with-sarah-halstead/id1273935631 Spotify: https://open.spotify.com/show/3EdszkVArwM4JvBBeLUL7T Email: [email protected]

Enjoyed the episode? Like, subscribe, and share it with a comic, actor, or podcast fan who'd appreciate a real conversation about stage time, social media, comedy hustle, and taking creative risks.

#DrinkingDuringBusinessHours #ComedyPodcast #YouTubePodcast #SarahHalstead #RichChassler #StandUpComedy #SparklingWine #Champagne #PodcastEpisode #MarriedComedians #EntertainmentPodcast #ComedyStories #VideoPodcast #HollywoodComedy #WineTalk

Bob Kushell on The Simpsons, Stand Up, and Starting Over in Hollywood

What happens when a veteran TV comedy writer steps away from the writers' room and starts over in stand-up?

In this episode of Drinking During Business Hours, hosts Sarah Halstead and Rich Chasler sit down with legendary television writer, producer, showrunner, and comedian Bob Kushell for a funny, candid, and deeply personal conversation about comedy, Hollywood, reinvention, and finding your voice again.

Bob Kushell shares stories from his incredible career writing and producing some of television's most iconic shows, including The Simpsons, Dream On, 3rd Rock from the Sun, Grounded for Life, Anger Management, The Muppets, and more. He opens up about the realities of TV writers' rooms, the pressure of writing comedy at the highest level, and why stand-up comedy has become the most authentic creative work of his life.

Over a bottle of 2020 Cab Franc from Absolution Cellars, the conversation explores the changing culture of Hollywood, public setbacks, personal growth, healing through comedy, and the courage it takes to begin again.

If you love comedy podcasts, stand-up comedy, TV writing, Hollywood stories, creative reinvention, and behind-the-scenes entertainment industry conversations, this episode is for you.

Guest Info

Bob Kushell is a veteran television writer, producer, and showrunner whose credits include Dream On, The Simpsons, 3rd Rock from the Sun, Grounded for Life, Anger Management, The Muppets, and the British comedy Way to Go.

In this episode, Bob shares stories from his decades in television, talks about the changing culture of Hollywood, and explains why performing stand-up comedy full-time now feels like the most authentic work of his career.

Guest Social Links

Bob Kushell Instagram: @bob.kushell

Drink of the Podcast

2020 Cab Franc, Absolution Cellars A Central Coast California Cab Franc with a story behind it, discovered by Sarah and Rich during a trip to Morro Bay. The hosts also shout out the winery's distinctive hand-painted labels and family-run feel.

Chapters

00:00 Welcome and wine intro: Absolution Cellars Cab Franc

04:40 Introducing Bob Kushell

07:10 Why stand-up now feels like home

15:45 Bob's early writing life and first TV jobs

21:30 Dream On, The Simpsons, and 3rd Rock from the Sun

34:50 The joy of making his own work

38:15 Career fallout, writers' rooms, and changing Hollywood

59:20 Returning to stand-up after years away

1:01:45 Socials, upcoming shows, and wrap-up

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!

If you enjoyed this episode, make sure to like, comment, and subscribe for more conversations with comics, creators, and entertainment industry insiders. Tell us in the comments: What was your favorite Bob Kushell moment from this episode?

#DrinkingDuringBusinessHours #BobKushell #ComedyPodcast #StandUpComedy #TVWriter #TheSimpsons #3rdRockFromTheSun #ComedyWriter #HollywoodStories #CreativeReinvention #SarahHalstead #RichChasler #WineAndComedy #ComedianInterview #PodcastShowNotes

x

Danny Farber on Vertical Filmmaking, Platform Strategy, and the Future of Storytelling

Danny Farber joins Drinking During Business Hours for a smart, energetic conversation about what it really takes to build a creative career across directing, acting, producing, and modern platform-driven storytelling. Sarah and Rich dig into Danny's rise in vertical filmmaking, his approach to respecting the platform, and why story, pacing, and audience behavior matter just as much as traditional craft. The episode also explores the balance between art and commerce, the realities of international production, and why authenticity and relationships still drive the industry forward.

As an actor, Danny has appeared in 1923, Chicago Fire, Proven Innocent, national campaigns for Chase, Home Depot, and Subway, and comedy/digital outlets including Funny or Die, Cracked, and The Onion. He trained at Second City, The Groundlings, UCB, and iO Chicago.

If you're interested in vertical filmmaking, directing, acting, film production, networking, storytelling, or platform strategy, this episode is packed with useful insight from someone actively shaping the space.

Guest Info: Danny Farber

Danny Farber is a Chicago-born director, actor, writer, and producer based in Los Angeles. His work spans vertical dramas, music videos, commercials, branded content, and narrative film, and his projects have generated tens of millions of views across social platforms. Since 2023, he has directed more than twenty feature-length vertical dramas for platforms including ReelShort, Dramabox, Goodshort, Dramapops, and KalosTV, with productions in Los Angeles, Istanbul, London, and Vancouver. He also wrote, directed, and starred in the award-winning short film "Thoughts and Prayers," executive produced by Amy Poehler.

Guest Social Links

Danny Farber Instagram: https://www.instagram.com/sirdannyfarber/ Website: https://www.sirdannyfarber.com/ Pretty Awesome Productions: https://www.sirdannyfarber.com/shop Thoughts and Prayers: https://www.instagram.com/reel/C8uo4EOPz5v/

Drink of the Podcast

This episode features two wines on the table: a 2022 Shafer TD-9 Napa Cabernet and La Fiorita Brunello. In the conversation, the hosts describe the Shafer TD-9 as iconic with a phenomenal nose and palate, and later shift from Cab to Brunello during the interview. Danny specifically joins them in drinking wine rather than a mocktail.

Chapters

00:00 Welcome back and introduction

02:45 The business of show business

05:37 Meet Danny Farber: director, actor, producer

08:32 Respecting the platform

11:12 The art of vertical storytelling

14:02 Navigating the challenges of production

16:48 Authenticity in performance

19:13 The balance of art and commerce

22:32 International productions and global filmmaking

27:25 Building relationships in the industry

32:08 The evolution of directing and storytelling

37:43 Understanding the vertical format

47:07 Leadership, collaboration, and communication on set

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Sarah

IG @sarahhalstead https://www.instagram.com/sarahhalstead/?hl=en

FB @sarahjhalsteadcomic https://www.facebook.com/sarahjhalsteadcomic/

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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!

Enjoyed the episode? Like, subscribe, and share it with a comic, actor, or podcast fan who'd appreciate a real conversation about stage time, social media, comedy hustle, and taking creative risks.

#DannyFarber #VerticalFilmmaking #FilmIndustry #Directing #Acting #Storytelling #PlatformStrategy #CreativeCareers #FilmProduction #Microdrama

From Teen Dad to Touring Comic: Willie Macc on Pain, Parenting & Punchlines

What happens when comedian Willie Macc sits down with Sarah J Halstead and Rich Chassler over a killer bottle of wine? You get one of the funniest, rawest, and most unexpectedly heartfelt episodes of Drinking During Business Hours.

In this episode, Willie opens up about becoming a father at 16, building a career as a commercial actor, choosing the uncertain road of stand-up comedy, and why he's betting on himself now more than ever. The conversation dives into parenting, religion, mental health, growing up under strict rules, being on the autism spectrum, and how pain can become powerful comedy material.

They also talk about Willie's upcoming special "Good Dad, Bad Father," his relationship with his son, comedy club politics, and why the long road might be the real road.

If you like comedy podcasts with real depth, big laughs, and zero fake energy, this episode is for you.

Guest Info

Willie Macc is a comedian, writer, actor, father, and "problem solver," with his official site calling him "Your New Favorite Storyteller." His X bio describes him as going "From BET College Hill to the commercial king and touring comic." In the episode, Willie also shares that his special Good Dad, Bad Father is headed to Amazon Prime in July.

Social Links

• Willie Macc Website: https://www.williemacc.com/

• Willie Macc X: https://x.com/funnywilliemacc

• Willie Macc Facebook: https://www.facebook.com/imwilliemacc/

• In-episode handle/spelling: "Willie Mack on everything" — W-I-L-L-I-E M-A-C-C Willie Macc Official Site X

Drink of the Podcast

2017 Michel Chapoutier Costieres de Nimes A Rhône blend discussed in the episode as including Grenache, Syrah, Mourvedre, Cinsault, and Carignan. Sarah frames it as a special bottle from the cellar, opened because Willie is a guest they genuinely wanted to celebrate.

Chapters

00:00 Intro, new glasses, upcoming shows 03:22 Opening the wine and welcoming Willie Macc 07:59 The casting advice that changed Willie's commercial career 09:39 Why Willie is choosing stand-up over comfort 12:24 Becoming a dad at 16 and the origin of Good Dad, Bad Father 16:47 Religion, preacher-family pressure, and hard questions about faith 25:20 Willie's son, parenting, and autism 36:43 Fathers, grandparents, discipline, and what changes over time 43:38 The stand-up grind and comedy club politics 46:20 Mental health, dark thoughts, and staying in the fight 48:20 Braille, perspective, and Willie's dark comedy film idea 50:20 Questions for God, upcoming special, socials, and outro

Drink of the Podcast

2017 Michel Chapoutier Costieres de Nimes A Rhône blend discussed in the episode as including Grenache, Syrah, Mourvedre, Cinsault, and Carignan. Sarah frames it as a special bottle from the cellar, opened because Willie is a guest they genuinely wanted to celebrate.

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!

Enjoyed the episode? Like, subscribe, and share it with a comic, actor, or podcast fan who'd appreciate a real conversation about stage time, social media, comedy hustle, and taking creative risks.

#DrinkingDuringBusinessHours #WillieMacc #SarahHalstead #RichChassler #PodcastClips #ComedyPodcast #StandUpComedy #GoodDadBadFather #ComedyLife #SingleDadStories #Fatherhood #EntertainmentPodcast #ComedianInterview #DarkComedy #BehindTheLaughs #PodcastRecommendations #ComedyFans #WineAndComedy #FunnyAndRaw #BetOnYourself