Drinking During Dojo Hours with Cobra Kai's Dan Ahdoot
Release Date: 11/11/2025
Laurie Douglas on Comedy, Social Media, and Why Art Should Make People Uncomfortable
Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!
Laurie Douglas on Comedy, Social Media, and Why Art Should Make People Uncomfortable In this episode of , Sarah and Rich welcome for a funny, sharp, and honest conversation about comedy, acting, artistic risk, and what it really takes to build a career in entertainment. From the grind of getting stage time in Los Angeles to balancing stand-up with acting and self-promotion, Laurie shares a real look at the hustle behind the laughs. The episode also dives into how comedians use social media, why live audience response still matters, and why great art should make people feel something. Laurie...
info_outline
How Ben Gleib Reinvented Late Night on YouTube, Went Viral in Political Debate, and Helped Save Comedy During COVID
Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!
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...
info_outline
Fizaa Dosani on Going Viral Without Selling Out | Comedy, Culture & Mental Health
Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!
Fizaa Dosani on Going Viral Without Selling Out | Comedy, Culture & Mental Health Stand-up comedy is changing fast and is right in the middle of that evolution. In this episode of , hosts and sit down with the comedian, actor, writer, and creator of for a funny, honest, and unfiltered conversation about authenticity, sobriety, social media, diversity in comedy, and the unpredictable future of stand-up. Fizaa opens up about building a career without losing her voice, why organic conversations matter more than polished performance, and how comedians are adapting to a world shaped by...
info_outline
From ChoCo Krispies Commercials in Colombia to Netflix Is A Joke Fest: The Brittany Ross Story
Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!
From ChoCo Krispies Commercials in Colombia to Netflix Is A Joke Fest: The Brittany Ross Story Sarah J. Halstead and Rich Chassler sit down with the wonderfully funny and refreshingly honest Brittany Ross, a Los Angeles-based comedian, actress, writer, and podcast host whose life story reads like a comedy special waiting to happen. They kick things off with some Passover prep banter before diving into the kind of real, warm conversation this show does so well. Brittany opens up about navigating identity and religion as a self-described “late in life Jew,” the very specific chaos of being a...
info_outline
We Drink for a Living But Not Tonight (Mocktail Episode)
Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!
We Drink for a Living But Not Tonight (Mocktail Episode) No guest? No problem. Hosts Sarah J. Halstead and Rich Chassler fly solo in one of the most wide-ranging and entertaining episodes yet, fueled not by wine, but by Malto Benny’s Pink Grapefruit Sparkling Water. They dive deep into the shifting alcohol landscape: why Gen Z is putting down the bottle, the ongoing debate over wine’s health benefits, how premium wine is holding strong while budget bottles tank, and the unexpected role cannabis taxes played in nudging millennials back to booze. Then it’s tour recap time as...
info_outline
Meet Eric Guilmette: The Actor Rewriting the Rules of Hollywood One vertical At a Time
Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!
Meet Eric Guilmette: The Actor Rewriting the Rules of Hollywood One vertical At a Time Hosts Sarah J. Halstead and Rich Chassler sit down with Los Angeles-based actor, producer, and poet Eric Guilmette one of the most prolific and buzzed-about names in the exploding world of vertical drama. A Massachusetts native who traded a math and economics degree and a likely Wall Street career for a one-way ticket to Australia, Eric’s path to Hollywood is anything but conventional. He went from fitness coaching on a laptop while globe-trotting, to modeling, to commercial acting, to becoming a bona fide...
info_outline
10 Tonight Shows, One HBO Special, and 40 Years of Telling the Truth: The Unstoppable Cathy Ladman
Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!
10 Tonight Shows, One HBO Special, and 40 Years of Telling the Truth: The Unstoppable Cathy Ladman Episode Summary Hosts Sarah J. Halstead and Rich Chassler sit down with veteran comedian, actress, writer, and comedy coach Cathy Ladman for a rich and deeply personal conversation spanning four decades in stand-up. A native New Yorker now based in Los Angeles, Cathy has appeared on The Tonight Show ten times — with Johnny, Jay, and Jimmy — and was the only female comic to appear on the final two anniversary shows of The Tonight Show Starring Johnny Carson. She’s won the American Comedy...
info_outline
How a Comedy Legacy Shapes Today’s Industry: Zoe Friedman’s Mission
Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!
How a Comedy Legacy Shapes Today’s Industry: Zoe Friedman’s Mission Hosts Sarah J. Halstead and Rich Chassler sit down with Zoe Friedman, comedy industry veteran, co-founder of Comedy Gives Back, former Late Show with David Letterman talent booker, and daughter of legendary Improv founder Budd Friedman. Zoe didn’t just grow up around comedy she grew up inside it, doing cartwheels on stage during Andy Kaufman’s Children’s Cabarets and getting homework help from Richard Pryor at the bar. From talent booking at Letterman to VP of Development at Comedy Central to co-founding the only...
info_outline
I Don’t Want to Be Strong Today: Vanessa Graddick, The Social Worker Who Became a Comedian
Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!
I Don’t Want to Be Strong Today: Vanessa Graddick, The Social Worker Who Became a Comedian Hosts Sarah J. Halstead and Rich Chassler sit down with the brilliantly funny and deeply thoughtful Vanessa Graddick, comedian, producer, social worker, and now published author. Vanessa opens up about starting comedy on November 1, 2006, after her mother’s cancer diagnosis, serving Allen Iverson at Applebee’s, performing for troops across Kuwait, Iraq, Afghanistan, South Korea, and Japan, and why she believes every human being should be required to work in a restaurant for 90 days. The...
info_outline
We’ve All Been One - Doug Bass Gets Real
Drinking During Business Hours with Sarah Halstead and Rich Chassler | Where comedy & fine wine meet!
We’ve All Been One - Doug Bass Gets Real Grab your favorite glass and pull up a chair this week, comedians and husband-and-wife duo and welcome a familiar face to the DDBH couch: LA-based comedian, actor, and podcast host . You may remember Doug from when Sarah and Rich were guests on his show The Basshole Podcast — in what Doug himself called “the first time a married couple has ever graced the show.” Now the tables are turned, the wine is poured, and Doug is spilling everything about building a comedy brand from the ground up, the art of getting people to share...
info_outlineSarah and Rich pour laughs and glasses with Cobra Kai's own Dan Ahdoot for a conversation that's equal parts comedy, wine, and "no mercy." They talk about why Dan is moving back to New York, dining adventures with Ralph Macchio, and even the secrets of "inside wine trading." Grab a glass, settle in, and join them for a mix of comedy, storytelling, and great wine - with a splash of mischief.