Welcome to another episode of My First Stage! This is the podcast where we dive into the early moments of some of today’s most seasoned speakers. We talk about the nerves, the mishaps, the lessons, and the surprising paths that can turn one first stage into a lifelong calling—and a business superpower.
This week, I sat down with Jeremy Shapiro, a serial entrepreneur, author of Your Business Growth Playbook, and host of the Your Business Growth Podcast. Jeremy’s story is not just a masterclass in public speaking, but also a hilarious reminder that sometimes the biggest mishaps become our most pivotal memories—yes, even if they involve ripping your pants before a big sales pitch.
Jeremy Shapiro has spent 30 years building businesses and helping other entrepreneurs break through plateaus and frustrations. He’s a systems thinker, a champion of iterative growth, and a firm believer in just getting out there and starting—even if you’re scared, unprepared, or in desperate need of a tailor. As an author, podcast host, and sought-after speaker, Jeremy’s advice is equal parts practical, actionable, and empathetic (with plenty of war stories to prove it).
Here’s what Jeremy and I covered in our conversation:
- A First Stage You’ll Never Forget: Jeremy recounts his first big speaking gig—a nerve-wracking sales presentation, complete with cold calls, last-minute changes, and a catastrophic wardrobe malfunction.
- Teaching vs. Selling from Stage: The psychological and tactical differences between teaching a small interactive class and commanding a big room with a clear sales goal.
- The Power of Systems (and Scripts): How following a tried-and-true framework can help conquer your fears and get real results, but why injecting personality and adapting is key.
- Failing to Sell Live: The painful story of a zero-sales webinar, what went wrong, and how feedback and constant tweaking turned a flop into an eventual success.
- Building Connection and Confidence: How Jeremy learned to bring personal stories, improv, and interactivity into every presentation.
- Secrets to Audience Engagement: From hand raises to “trial closes,” real-world tactics for keeping a crowd involved—even when you can’t see them through the blinding stage lights.
- The Book, the Podcast, and the Trifecta: Why Jeremy believes in having multiple platforms as a thought leader and how he uses each to land more stages and clients.
- Real Advice for Getting Started: Why embarrassment is part of the journey, why MVPs matter, and how every pedal stroke and every ripped pair of pants get you closer to your dream stage.
If Jeremy’s story got you fired up (or left you checking your own pants before your next talk), here’s what you can do:
- Share Your First Stage Story – I want to hear from YOU! What was your most memorable first time on stage? Head to myfirststagepodcast.com and share your story.
- Connect with Jeremy – Check out Jeremy’s book and podcast at yourbusinessgrowthplaybook.com for more tips on growing your business and your confidence.
- Subscribe & Review – If you loved this episode, subscribe to My First Stage, leave a review, and let’s keep sharing these real behind-the-scenes journeys.
- Start Speaking, Start Failing – Seriously: pitch yourself for a local workshop or event, host a webinar, just get in the reps. Every “embarrassing” start is an investment in your future success.
Thank you so much for listening to this episode. I can’t wait to bring you more raw, honest, and inspiring first stage stories right here on My First Stage!
Timestamped Summaries
[00:00-01:02] – I introduce Jeremy Shapiro and set the stage for his first-stage story—about being thrown into a sales presentation he wasn’t expecting (and most definitely wasn’t ready for).
[01:04-03:28] – Jeremy describes his absolute reluctance to be on stage, the shock of having to cold call hundreds of prospects, and the blunt reality of a pre-pitch wardrobe disaster.
[03:28-04:14] – What do you do when you rip your pants an hour before your first big speaking gig? Learn about Jeremy’s mad dash to a tailor and how the show had to go on.
[04:14-06:37] – Breaking down the difference between teaching a workshop and selling from a stage—and why that mental shift tripped Jeremy up at first.
[06:39-09:21] – Why selling from the stage is a different beast, and how bombing a live webinar taught Jeremy the value of iteration, constructive feedback, and refining your pitch.
[09:33-10:40] – How switching from facts to stories, ditching the word-for-word script, and adding trial closes created a dramatic improvement in audience response and sales.
[10:45-11:22] – The practical mechanics of trial closes: getting audiences to nod, say yes, and qualify themselves before the final pitch.
[12:27-13:18] – In-person vs. online audiences, how body language can tell you everything, and what Jeremy learned from his wins and his losses.
[13:37-14:17] – The power (and limits) of techniques like scarcity bonuses, fast-action offers, and social proof to get audiences to actually take action.
[14:28-16:00] – How adding relevant, real, and recent stories instantly personalizes a presentation, breaks the fourth wall, and makes your audience lean in.
[16:18-18:19] – The cringe-worthy mistake of forgetting to click “start meeting” on a webinar with hundreds of people waiting, and how leading with vulnerability set up a more successful second run.
[19:30-20:31] – How Jeremy’s speaking career has evolved—facilitating small mastermind groups, commanding huge ballrooms, and loving every rep and every format.
[21:00-22:07] – The differences in interacting with thousands vs. dozens, how to harness audience energy, and why panels and conversations are a sweet spot.
[22:27-23:44] – Practical tactics for engaging big audiences you can’t see, from house light tricks to collective questions and building peer-to-peer connection.
[24:26-28:35] – Why the “trifecta” of book, podcast, and stage matters, and how each platform feeds the next—by opening doors, boosting authority, and turning audience members into clients.
[28:57-30:18] – Jeremy’s biggest advice: just start, embrace embarrassing failures, get the reps, and don’t try to perfect your way out of ever beginning.
[31:02-31:27] – One pedal stroke at a time: how Jeremy’s cyclist mindset applies to pushing onward in public speaking and entrepreneurship.
