The Grind of Comedy with Dean Delray

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

Release Date: 01/20/2026

Chef Steve Samson on Rosso Blu, Bologna, Gnocchi, and the Real Cost of Running a Restaurant

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

Chef Steve Samson on Rosso Blu, Bologna, Gnocchi, and the Real Cost of Running a Restaurant The Italian Food Secret LA Has Been Hiding This week on Drinking During Business Hours, Sarah Halstead and Rich Chassler sit down with Michelin-recognized chef and restaurateur Steve Samson for a rich, hilarious, and deeply personal conversation about Italian food, the restaurant life, and what it really takes to build something lasting in Los Angeles. Steve is the chef and co-owner of Rosso Blu in downtown LA, a Bolognese-inspired restaurant that Rich and Sarah recently visited and could not...

Apparitions, the FBI and a Bottle of Chardonay with Jennifer M Shaffer

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

Jennifer M Shaffer Talks Apparitions, the FBI and a Bottle of Chardonay Comedians Sarah J. Halstead and Rich Chassler pop a 2021 Gentleman Farmer 100% Chardonnay and pour it out with Jennifer M. Shaffer internationally recognized intuitive, spiritual medium, medical intuitive, and former stockbroker-turned-triathlete who’s worked with the FBI, U.S. Secret Service, and Dark Web Division. They cover ADHD-approved Chardonnay, 800 bottles stashed in kitchen drawers, the secret to a 30-year marriage, why Jennifer never watches the news, the French Bulldog bedspread that cracked an FBI fentanyl...

Keith Reza on Comedy, Fame, and Never Giving Up

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...

Inside Darren Carter's Laugh Factory Slot 19 Strategy

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...

David Leaf on Brian Wilson, SMiLE & The Beach Boys

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

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...

Lesley Wolff on Hollywood Casting, Comedy & Acting Careers

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

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...

Mateen Stewart Gets Real on Comedy, Rejection & Bigger Doors

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

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...

She Did Fallon While Raising Twin Boys?! | Jessica Keenan on Comedy, Motherhood & Chaos

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

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...

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

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

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...

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

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

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,...

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The Grind of Comedy with Dean Delray

In this episode of “Drinking During Business Hours,” hosts Sarah J Halstead and Rich Chassler sit down with veteran comedian and podcaster Dean Delray for an honest, inspiring conversation about the comedy hustle. Fresh from a memorable road trip complete with incredible food stops (including the legendary Rose’s Cantina in El Paso), the hosts dive deep into Dean’s journey through the stand-up world. Dean shares the story behind his groundbreaking new comedy special “5836,” filmed in a Tennessee cave, and discusses why self-production has become essential in today’s entertainment landscape. This episode is packed with hard-earned wisdom, hilarious stories, and a raw look at what it takes to survive

FEATURED GUEST

Dean Delray - Stand-Up Comedian, Podcaster, and Host of “Let There Be Talk”

IG @deandelray https://www.instagram.com/deandelray/

X @deandelray https://x.com/deandelray?lang=en

Website https://www.deandelray.com/

Podcast Let There Be Talk https://podcasts.apple.com/us/podcast/dean-delrays-let-there-be-talk/id546210508

Dean Delray is a veteran stand-up comedian known for his authentic, high-energy performances and his popular podcast Let There Be Talk, where he interviews fellow comedians, musicians, and artists. With decades of experience grinding it out on the road, Dean represents the true working comedian, someone who’s built a career through relentless perseverance, authenticity, and an unwavering love for the craft. His latest special “5836” showcases his unique approach to comedy production and his commitment to doing things his own way.