Hiring a Former CEO Keynote Speaker on AI? Here's How I'd Think About It.

If you’re searching for a former CEO keynote speaker on AI and the future of work, you’ve probably noticed there aren’t many of us. This page is my honest take on who’s in that category, what each of us is actually good for, and where I fit, including where I don’t.

This is not an independent ranking. It is my perspective as a speaker in this category, based on public positioning, bureau listings, event-market norms, and where I believe each speaker is strongest.

Why “Former CEO” Is the Right Filter

When you’re hiring someone to talk to your team about AI, you’re not just buying an hour of content. You’re buying judgment that’s been tested against real consequences.

Former CEOs can bring something many consultants and academics do not: direct accountability for decisions that had real consequences. We’ve sat in the chair where the decision actually gets made, balanced innovation against quarterly earnings, managed a board through disruption, and lived with what happens when a bet doesn’t pay off. AI adoption is not only a technology problem. It is a leadership, operating, and judgment problem, and that’s the lens a former CEO brings that a theorist doesn’t.

What that actually looks like:

– Real-world transformation: the late-night conversation with an employee worried about their job, the call on which roles to automate and which to protect. That’s lived experience, not a case study.

– Judgment under uncertainty: if you’ve led a company through one major shift, you know how to make decisions before the full picture is clear.

– P&L accountability: getting it wrong meant real cost, jobs, board confidence, culture. That changes how you talk about risk.

– No-hype honesty: when you’ve had a product flop and had to explain it to a room, you lose patience for hype fast.

Where I Fit

My background, briefly

I scaled Mike’s Hard Lemonade from a startup concept into a $200 million brand in three years, despite being allergic to alcohol, which probably tells you more about how I approach a market than any stat could. I built distribution from nothing, created a category that didn’t exist yet, and did it against beer-industry competitors with a century of head start. Before that I worked in hospitality (Four Seasons, Holiday Inn) and in Hollywood. After Mike’s, I wrote, directed, and produced Beer Wars, a documentary that played theatrically, was distributed by Warner Bros., and has streamed on Netflix, Amazon, and Apple TV.

That combination, operator, brand builder, storyteller, is where my framework comes from.

What I actually talk about

My core material is The Human + AI Equation™: a practical framework for deciding what work stays human-led, what should be AI-augmented, and what can be automated. It’s not about what AI might do someday. It’s about what to do with it next.

The framework breaks into three steps: define the outcome you actually need, identify which parts of the work require human judgment versus where AI capability adds more value, then determine the right mix between the two. That mix isn’t fixed. It shifts as the work changes and as the technology matures.

I built it from the inside of an organization, not from watching one. I’ve managed budgets, hired and fired, launched products that flopped, and made the calls that decided whether the company survived. When I talk about AI adoption, I’m talking about the same forces you’re dealing with: resistance to change, budget limits, the gap between what leadership wants and what the front line will actually do.

Who’s booked me

Hitachi, Rockwell Automation, Farmers Insurance, Bridgestone, Verisk Analytics, United Healthcare, Merrill (Bank of America), AMC, Capgemini, Chevron, and dozens of other organizations and associations across insurance, manufacturing, healthcare, technology, and financial services. Audiences from 50 to 5,000+, formats from executive roundtables to arena keynotes.

Fee range

– In-person: $25,000-$40,000, depending on scope, travel, and customization

– Virtual: starting at $15,000

– Workshops and extended engagements: custom pricing

What clients say

“Throughout the event, I’ve received so many positive comments about your session. The overall response is decidedly NOT dystopian.” – Rockwell Automation

“Your talk asked the team to look within themselves to determine what they were going to do differently to win. Yours was the highest-commented session of the day.” – Farmers Insurance

“Quite simply, your speech was a home run.” – Verisk

Where I Don’t Fit, and Who Does

I’d rather tell you this directly than let you find out after you’ve booked the wrong speaker. None of us are interchangeable, the table below is the fastest way to see who actually fits your event.

Comparison at a Glance

My fee range reflects my own confirmed rate. Fee ranges for other speakers below are public-market estimates and may vary by event type, date, location, format, usage, travel, and booking channel. I cannot confirm these figures on their behalf.