Could an AI-powered booking system really score you 3 to 8 paid speaking gigs every single month—even if you don’t have a massive following?

In this kickoff episode of Path to the Main Stage Season 2, host Li Hayes and the dynamic tech expert & speaker Ramon Ray pull back the curtain on the promises (and pitfalls) of AI in the world of professional speaking—and reveal why the secret to getting booked still lies in genuine human connection.

From outlandish claims hitting LinkedIn inboxes to behind-the-scenes tactics that event planners actually use, Li and Ramon dissect the hype around AI booking tools. You’ll hear why Ramon believes a handshake still beats any algorithm, how personal follow-ups secure long-term relationships and stages, and why sometimes, it’s showing up in person that seals the deal.

Key highlights include:

• Real talk about using AI for speaking gigs—what it can do, and what it absolutely can’t
• Why top-paid speakers with millions of views don’t rely on automation to get booked
• Ramon’s practical, story-driven strategies to build trust, connect with event planners, and follow up like a pro
• Insights on the “dating game” of nurturing leads, marrying customers, and staying memorable post-event
• Inside advice on navigating no’s, referrals, testimonials, and the importance of reputation management—even among celebrity speakers

If you want actionable, street-smart wisdom for breaking into bigger and better stages (with tech AND heart), this episode is a must-listen!

Episode Overview & Timestamps:

• [00:00:00] – Li Hayes opens with a surprising pitch from an AI-powered speaker booking system
• [00:04:08] – Ramon Ray joins: Is AI truly a golden ticket for speakers?
• [00:07:12] – The power and limits of automated systems vs. the human connection
• [00:09:29] – Event planners’ real decision-making process and why Zoom calls matter
• [00:12:45] – Ramon shares a personal story about building connections at 30,000 feet
• [00:16:18] – The “date your leads, marry your customers” approach to follow-up
• [00:20:47] – Staying top of mind after the contract is signed (gentle follow-up strategies)
• [00:23:33] – Soft confidence and reinforcing your value without bragging
• [00:28:37] – How new speakers can break in—local connections & chamber events
• [00:33:12] – Ramon's secrets for onsite connection and standing out at events
• [00:37:01] – What to do after the curtain falls—testimonials, follow-ups, and referrals
• [00:44:42] – Reputation matters: Why agents talk and why good behavior pays off
• [00:51:51] – Why “no” is not the end—and how to handle rejection gracefully
• [00:56:47] – The power of showing up in person (Li’s game-changing Atlanta story)
• [00:58:27] – Wrap-up and final thoughts on the balance between tools and true connection

Listen in for practical advice, memorable anecdotes, and the energizing chemistry between Li and Ramon that'll inspire you to level up your speaking career—with a human touch.

Subscribe and watch the full episode on YouTube, or learn more at pathtothemainstage.com.