What if the “big break” you think you need as a speaker is actually holding you back?
On this episode of Path to the Main Stage, host Li Hayes sits down with Kevin O’Connor—longtime host of “This Old House” and a recognized TV personality who never set out to be in the spotlight. In a jaw-droppingly frank conversation, Kevin reveals why being represented by a major talent agency nearly ended his speaking career before it began—and why “celebrity” status isn't the golden ticket most believe it is.
With decades of national TV experience but humble beginnings in banking, Kevin shares his roundabout journey from accidental TV star to in-demand keynote speaker. He pulls back the curtain on what truly matters for landing mainstage gigs, the hidden pitfalls of big agencies (including the unsettling reality of “back-pocketing”), and how your values—and your ability to say “yes”—can open doors you never knew existed.
Key highlights include:
- How Kevin went from weekend “grip and grin” appearances to commanding top-dollar keynotes for leading associations
- The critical difference between being known and being known for something
- Why the wrong agent can quietly sabotage your career, and what Kevin learned from being “back-pocketed” by a huge agency
- Why you don’t need a bureau to start getting speaking gigs—and the mistakes most celebrities make when entering this world
- The unglamorous truth about corporate events: What clients and audiences expect, and why the real work starts after you leave the stage
- The power of “yes”—how being available, present, and engaged off-stage delivers exponential returns in relationships, opportunities, and show-stopping moments
- Practical, hard-won advice for building both a strong speaking business and a personal brand grounded in authenticity
Whether you’re an emerging speaker or a seasoned pro, this episode cracks open the myths of the industry and offers a behind-the-scenes look at what it really takes to own the main stage.
Episode Overview
- 00:00 – Introduction to the journey of professional speaking
- 02:24 – Kevin O’Connor’s unconventional entry into television and speaking
- 04:44 – Major agency experience: the pitfalls of being treated like a “celebrity”
- 09:06 – The back-pocketing tactics of agencies and why exclusivity can hurt
- 14:42 – Kevin’s evolution from “grip and grin” to corporate keynotes
- 20:04 – The dual demands of clients and audiences
- 26:21 – How to prepare—story arcs, props, and professional polish
- 33:50 – The real value beyond the speaker’s fee: relationships, video, access
- 38:40 – The “power of yes” and building lasting value offstage
- 41:17 – Why all clients—big or small—deserve your best
- 42:11 – If Kevin could give advice to his past self: What emerging speakers must do now
- 43:48 – Final takeaways and closing thoughts
Ready to skip the myths and make your own path to the main stage? Listen now!
