If This Doesn’t Work…

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://...

Ray Wroten from Bond & Bentley pulls up to the studio to talk touring, local Maryland venues, why the band re-recorded fan-favorite songs instead of “remastering,” and how recording live in the room keeps the human feel intact. We also get into: ridiculous band name ideas, bar-gig requests, “Two Dollar Hot Dog / One Dollar Water,” sobriety + anxiety spirals, meditation that actually works, run...

TMZ Baltimore (YC) pulls up to If This Doesn’t Work… to talk about building Baltimore’s biggest blog/vlog page, going viral during the pandemic, rebuilding the page 11 times, and why he switched from posting drama to posting his own life. YC also shares a heavy, real story about a laced street edible, months in the hospital, therapy, and turning that experience into his independent film “Laced” (d...

Baltimore comedian Bam Jacobs pulls up for a chaotic episode: stage name origin, growing up Baltimore/Bel Air, Chuck E. Cheese stories, getting arrested for stealing chocolate milk, comedy writing vs storytelling, true crime doc obsession, and a full run of unhinged hypotheticals. In this episode:-Why he chose “Bam” (and why stage names can be corny)-Baltimore vs Bel Air + the “claiming the city”...

If This Doesn’t Work… is back! and this one’s for the DMV.We’re joined by The Walking Flame, a rapper from Annapolis, Maryland, to talk about building a real brand, learning to record + mix at home, performing in Pittsburgh, and being open about OCD and what it took to overcome the worst years of it. We get into how visuals changed everything, why Maryland needs more venues for artists, the story...

Dre 91 (Retro Since 91) pulled up and this one went everywhere. From not caring about metrics, to therapy + divorce, to why love is a higher vibration than authenticity, to “brain rot” guilty pleasures like Love After Lockup and public freakouts. We also get into Dre’s new project WAVESSS and how he builds as an artist: short tracklists, retro visuals, wrestling inspiration, and a team behind the...

Standup comedian Adam Freesman joins If This Doesn’t Work… for a fully unhinged hang. We talk about how he went from a Division 1 track & field thrower to a Baltimore comic, getting guns pulled on him by literal kids, bombing at early open mics, porn-brain relationships, intrusive thoughts, Thanksgiving food hot takes, and why so much modern comedy content kinda sucks. In this episode we get i...

Philly legend Reed Dollaz pulls up for Episode 100 of If This Doesn’t Work… and gives us a full timeline, from juvenile placement and “Too Raw for the Streets” VHS & DVDs to URL stages, Eminem’s “Rap God” video and his new project Reedvenge 4.In this episode, Rambo Reed talks about:Starting to rap at 11, ciphers at 13, and being “really him” in Philly before YouTubeThe classic Reed vs. Trigger...

Baltimore’s own TYTY2900 pulls up for his first-ever podcast interview and taps in about hood vlogs, jail, fatherhood, and turning real life in the trenches into YouTube content. We talk about growing up in West Baltimore, doing time in county & city jail, how overdoses and the drug epidemic brought big platforms to the city, and why he refuses to incriminate anybody on camera, no matter how m...

Baltimore’s own Timothy Fletcher, the drummer who went viral for his insane street performances and ended up on Ellen and America’s Got Talent among other big stages, joins If This Doesn’t Work… to talk about his journey from high-school band kid to international performer. He opens up about his early struggles, losing friends, the grind of street drumming, his Fortnite emote deal, YouTube copyrig...

Justin sits down with his longtime friend Dave Pechillo, a finance-minded, crypto-curious realist — to talk about money, freedom, relationships, AI, and why billionaires eventually get bored of everything. They unpack what real financial freedom looks like, why most people don’t actually want infinite money, and how chasing status turns normal dudes into psychos. From Elon Musk and Trump to cartel...