S10E8 - He Won Mexico For A Joke & Lost It To Bad Seafood; Comedy, Chaos, Connection & Lessons Beyond the Algorithm!!

What if reading a room could change how you brand, publish, and grow online? We sit down with comedian turned podcaster and tech founder Jeff Dwoskin to unpack the craft behind connection: the split-second choices that make strangers lean in, the nerves that never fully leave, and the moments on stage that teach you more than any marketing playbook ever could.

Jeff takes us from a bold tag that won a comedy contest to the rebrand that finally fit his show. The journey from The Jeff Dwoskin Show to Live From Detroit to Classic Conversations came down to clarity: names and artwork should explain, not confuse. We dig into why shortening intros, cutting filler segments, and ditching distracting music boosted listener focus and reclaimed precious prep time. The result is a format you can sustain, not just survive.

We also explore the roots of Stampede Social, born from years running trending Twitter games and rebuilt for Instagram and Facebook. Jeff explains how DM automation, trackable links, and top-fan insights turn casual comments into measurable actions. No more shouting URLs; invite listeners to DM a keyword and watch the data tell the story. Along the way, we talk boundaries with Facebook and Threads, and how to protect your headspace while still showing up for your audience.

The heartbeat of this conversation is a creator’s mindset: stop contorting your voice to every algorithm tweak. Earn the follow through craft, not clickbait. Keep your channel messy if that’s your truth. Book guests through genuine relationships. And remember Rob Lowe’s line that Jeff shares: don’t judge your insides by other people’s outsides. If you’re ready to refine your show, organise your socials, and create with less noise and more intent, you’ll find practical steps and a lot of laughs here.

If this resonated, follow the show, share it with a friend, and leave a review on Apple Podcasts or a rating on Spotify—your feedback helps more creators find us.

Check out STAMPEDE SOCIAL https://www.stampede.social/ use code PAULA20 for LIFETIME discount.

& Classic Conversations https://jeffisfunny.com/

Chapters

• 0:00 Cold Open And Laughing Start
• 2:32 Jeff’s Path Into Stand-Up
• 6:00 The Craft: Context, Connection, Stage Nerves
• 12:10 Contest Night, A Bold Tag, And A Win
• 16:30 From Comic To Podcaster And Rebrands
• 22:10 Logos, Names, And Letting Go
• 27:30 Streamlining Format And Cutting Filler
• 33:10 Enter Stampede Social: What It Does
• 38:00 Twitter Roots To Instagram Tools
• 41:50 Platform Frustrations And Mental Health
• 46:20 Creator Mindset: Ignore Algorithm Rules
• 51:30 Pivots, Regrets, And Lessons
• 55:05 Classic Conversations: Volume And Vision
• 1:00:00 Friendship, Energy, And Community
• 1:04:30 Where To Find Jeff And Stampede
• 1:07:00 Parting Advice And Closing CTA