Ryan Raymond is a comedian working in Chicago, Illinois! 💯In this episode, we discuss Ryan's 'Kaufman' phase (& how Mike Dwyer helped him escape it), why he left Logan Square, how to catch your ideas, why it's important to throw spaghetti at the wall, the brilliance of Bray Wyatt & John Cena, our love for Power Hour, and much more! 🔥_______TIMESTAMPS:0:00 - Intro & Guest Introduction0:45 - Vibes, Vagueness & Communicating Through Comedy4:03 - The Creative Process: Feeling vs. Thinking6:12 - Honest Feedback, Dangerous Encouragement & Early Success9:04 - Mastery in Comedy vs. Music13:53 - Comedy Auditions, Self-Doubt & Ryan's Kaufman Phase17:53 - Subversive Humor, Crashing & Finding What Works22:00 - Community, Hanging Out & Chasing Stage Time27:03 - Comedians, Podcasts & Off-Mic Moments30:05 - Accepting You Might Not “Make It”32:30 - Punk Roots, DIY Comedy & Scene Talk35:01 - Wrestling Tangent: WWE, Cena, Bray Wyatt48:33 - Backyard Wrestling & Writing Jokes on Stage50:28 - Getting Into Comedy Later in Life53:01 - Comedy’s Emotional Rollercoaster & Multiple Mics55:28 - Chicago Transit & Embracing the Cold1:02:00 - Navigating City Chaos & Outgrowing the Scene1:10:00 - Music That Ages With You: The Hold Steady & Tool1:12:00 - Polite Feedback, Bad Art & Comedy Burnout1:16:02 - Bombing, Confidence, & Passion Fatigue1:19:10 - Hobby vs. Career & The Trap of Success1:21:06 - Routines, Joke Fatigue & Creative Voice1:24:50 - Spaghetti Method & Identity on Stage1:29:05 - Balancing Intellect, Emotion, & Political Comedy1:34:05 - Creative Freedom, Comparison & Reinvention1:38:03 - Stunts, Edgy Humor & Meeting the Audience1:42:02 - Catching Ideas, Pop Music Simplicity, & Life Philosophy1:46:31 - Productivity Structure & Open Mic Favorites1:50:13 - Hosting vs. Producing & Having No Kids1:53:25 - Losing a Pet, Hip Replacements & Comedy as Therapy1:58:00 - Tragedy Material, Freestyling & Power Hour Energy2:02:01 - Drinkers, Hecklers & The Chaos of Power Hour2:08:03 - Wild Performances, Upcoming Shows & Final Message
