If This Doesn’t Work…

Comedian Karan Singh joins Justin for one of those episodes that starts with a name pronunciation and somehow ends up in Virginia Tech crime stories, Kash Patel impressions, plastic surgery office chaos, dating apps, bad jobs, local comedy, family expectations, and possibly the meanest grandma story ever told on the show. Karan talks about going from “K Squizzy” to his real name, growing up in Nor...

Steve Huber of 100.7 The Bay joins If This Doesn’t Work… for a long, honest conversation about Baltimore radio, growing up on a farm, starting at 98 Rock as an intern, becoming a music director, moving to 100.7 The Bay, and what happens when the station you helped build gets sold. Huber talks about the current situation at 100.7 The Bay, how the staff found out, what the final stretch feels like,...

Skyy Royal is back on If This Doesn’t Work… and somehow this episode starts with grief, turns into a conversation about spiritual massage, and ends up somewhere between the Matrix, Bigfoot, aliens, meat being dead bodies, and whether the world is a “dimensional threshold.”Skyy talks about losing his dog Fluffy, how he sees grief differently now, the coma experience that made him feel like he saw t...

Comedian Matt Pennington returns to If This Doesn’t Work… for a conversation that somehow moves from internet arguments and dispensary customers to childhood Adderall, getting arrested with mushrooms, cocaine heart-rate experiments, fear of looking cringey, and one of the best period-sex analogies ever told. Matt talks about working at a dispensary, why “sativa versus indica” does not tell the who...

Comedian Mert Wolf joins If This Doesn’t Work… for a conversation that starts with whether his mom would help with a drug deal and somehow gets stranger from there. Mert talks about growing up in Turkey, moving to America, legally choosing the last name Wolf, accidentally calling 911 during an argument, being haunted in Columbia, Turkish circumcision ceremonies, kidney stones, conspiracy theories,...

We still can’t believe this happened. On May 8th, we got to sit down with comedian Steve Hofstetter in the greenroom at Baltimore Soundstage before his show. Steve was insanely generous with his time, and the whole thing felt surreal; walking backstage, sitting behind the curtain, and getting a real conversation with someone who has been doing comedy at a level most people never reach. We talked a...

Comedian Luca Spinoso joins If This Doesn’t Work… for one of the wildest episodes we’ve had in a while. Luca talks about growing up between Florida and Maryland, his chaotic childhood, the stepmom from hell, getting stabbed while working as a bouncer, battling addiction, getting sober, becoming a husband, finding out he might be a dad, and somehow ending up in Baltimore comedy. He also tells the i...

This week on If This Doesn’t Work… we handed the microphone to our friend’s 9-year-old daughter and let her answer the kind of questions most adults can’t even handle. What followed was part Kids Say the Darndest Things, part tiny roast battle, part accidental philosophy seminar. Harleigh explains why adults make no sense, why dogs are probably faking it, what she’d do if she ruled the world, how...

Baltimore-area comedian Caitlin Austin joins If This Doesn’t Work… for one of the strangest, funniest, and weirdly heartfelt episodes we’ve done yet. Caitlin talks about growing up around Dundalk chaos, being raised by her grandmother, having a real-life “prison papa,” becoming a pre-K teacher, getting sober, starting stand-up comedy, living in her car while still going to open mics, smoking Newpo...

Baltimore graffiti legends DLordInk and Meca came through If This Doesn’t Work to talk about the real culture behind graffiti; the rules, the respect, the beef, the crews, the toys, the side-busting, and how street art turns into paid murals across the country. In this episode, Danny Lorden aka DLordInk and Meca break down what most people don’t understand about graffiti: how writers earn respect,...

Baltimore comedian Kwame Kumah joins If This Doesn’t Work… for a conversation that goes from completely ridiculous to surprisingly real. Kwame talks about growing up near Annapolis/Odenton, being raised by Ghanaian parents, getting influenced by his older sister’s 90s pop taste, and how his name connects to Ghanaian day-name traditions. He also gets into his finance background, reading graphs, how...

Dre aka RetroSince91 came back through If This Doesn’t Work… for a conversation about music, life, relationships, privacy, and staying true to yourself in a world that constantly pushes people to overshare, compare, and perform online. We talk about his new project Waves 2, why he leans melodic over purely technical rap, building a real community instead of chasing numbers, how divorce changed his...

Videographer Banga Jaxon stopped by If This Doesn’t Work… to talk about what it’s really like shooting music videos in Philly, Baltimore, and Delaware. From chaotic rap shoots, dangerous situations, fake money, contracts, and late-night calls, to working with bigger names, staying neutral in the scene, and why authenticity matters more than fame. This one goes all over the place in the best way. W...

Dom Solesky returns to If This Doesn’t Work… to talk about going viral, getting recognized in public, landing brand deals, getting management with Brillstein, and preparing for a Just for Laughs New Faces audition in New York. The conversation also gets into comedy, content strategy, creator money, construction work, Baltimore media, sports betting, and a lot of wild side roads along the way. Do y...

Jean-Marie Rose Pfeifer joins If This Doesn’t Work… for one of the wildest life stories we’ve heard on the podcast. We talk about addiction, jail, recovery, rebuilding her life, plant medicine, trauma, somatic healing, skydiving, and how she went from absolute chaos to owning a skydiving company and two airplanes. Jean-Marie also opens up about chasing an image of success, leaving New York behind,...

Davey Cook from True Colors Beauty Co stopped by If This Doesn’t Work for a conversation that went way deeper than beauty and business. We got into addiction recovery, grief, family, entrepreneurship, authenticity, confidence, and what it really takes to rebuild yourself while trying to create something meaningful. Davey opens up about getting clean, losing his mom, growing up around chaos, workin...

Matt Brown joins If This Doesn’t Work… for one of our wildest episodes yet. We get into his Kill Tony experience, what it’s actually like waiting in that bucket-pull chaos, why the Austin comedy scene wasn’t for him, and why he thinks most comics need to be bullied a little more. We also get into some much darker territory: losing both parents to cancer, addiction, acting out in high school, baseb...

Tommy Sinbazo might be one of the most interesting guests we’ve had on If This Doesn’t Work...Baltimore comedian, musician, builder, proud geek, and the man behind the band B.U.S.S.I. sits down with us to talk about everything from Dungeons & Dragons, LARPing, and medieval combat to robot building, metal music, murder mystery shows, voiceover work, 98 Rock, and growing up in Baltimore. We get...

Najee Thrash and Josh Grimes join If This Doesn’t Work… for a wild one that somehow covers relationship surveillance, peptides, dating gurus, UFC, Dune, Epstein files, AI, body cam footage, video games, and the absolute chaos of smelling salts. This episode goes from genuinely interesting to completely off the rails in the best possible way. If you like episodes where the conversation keeps mutati...

Justin Schlegel from 98 Rock joins us for one of the funniest episodes we’ve done. We get into his early radio grind, overnight shifts, working multiple jobs with zero sleep, and the insane format changes that had him constantly starting over in radio. Then we get into the good stuff:-Wild 98 Rock stories-how he got into stand-up comedy-moving to Los Angeles and coming back-almost losing the morni...

Na’im Ali pulled up and we got into the real comedian emotional rollercoaster: bombing so hard you question your whole life… then the next week you’re on top of the world. We talk Skankfest excess, Philly vs NYC (and why NYC is basically a rat civilization), writing jokes vs “just telling stories”, getting arrested over a bench warrant, plus the most chaotic hypotheticals you’ll ever hear. You Can...

Mo Noor pulls up and we immediately derail into self-care, Brazilian wax logistics, and the uncomfortable truth that everything is over-sexualized in 2026, and even “fluff the rice.”We get into:The weird politics of lotion / skincare / “serum” and why straight guys act like it’s illegalThe absolute insanity of prison pen-pal dating sites (aka “soup money”)Comedy growth: hosting, warming up a room,...

Roberto Reed pulls up and this episode immediately goes off the rails. From ball pain horror stories to body cam footage obsession, comedy origin stories, therapy debates, and the kind of riffs you can’t plan. We talk: starting standup at 19, dropping out of college, working at a comedy club, why fear is an underrated motivator, the weirdest ER visit ever, and how to stay grounded while chasing bi...

Nitres Tha Veteran pulls up to If This Doesn’t Work… to talk about the real meaning of being independent, why “ownership” doesn’t matter if you have nothing worth owning , and how most artists are doing “music” but not doing business . He breaks down coming up in Raleigh, NC , the difference between old-school album culture vs today’s viral single chase, and why originality is getting watered down...

Comedian Chris Randolph joins If This Doesn’t Work… for an episode that somehow hits everything: comedy scene honesty, weird jobs, “pet bird” psychopath energy, conspiracy rabbit holes (Mud Flood), the scariest truth about death (it’s basically FOMO), a brutal staph infection story, and a wild Baltimore night that ended with a bathroom gunshot story. You Can Find Chris Randolph:Instagram: https://...