Pitch Masters cover art

Pitch Masters

Pitch Masters

By: Danny Fontaine
Listen for free

About this listen

 The Pitch Masters Podcast is dedicated to helping you win more business. No matter how good your products or services are, without the right story, branding, and marketing, you might not get noticed. Danny Fontaine, AKA ’Pitch Guy’ interviews a master of pitching from industry in each episode and covers how behavioural science, psychology, storytelling, creative, and theatre all play huge roles in the success of your business.Copyright 2022 All rights reserved. Economics Leadership Management & Leadership Marketing Marketing & Sales
Episodes
  • S2 E02:Chris Hay, AI Technologist & Futurist

    S2 E02:Chris Hay, AI Technologist & Futurist
    Jun 22 2025
    Chris Hay, AI Technologist & Futurist When it comes to pitching, most people think about perfect slides, rehearsed lines, and the sweaty palms that come with trying to stick the landing. But as anyone who’s seen Chris Hay in action will tell you, great pitching rarely looks like a rigid script — and increasingly, it doesn’t happen without a little help from artificial intelligence. Chris and I know each other well through our time at IBM, where I’ve watched him pitch complex ideas to huge audiences without ever appearing tied to a slide deck. He describes himself as a “technologist, futurist and disruptor” — and if you listen to this episode, you’ll quickly see why. While he humbly claims he doesn’t ‘do pitching’, what he actually does is convince people to think differently about technology, the future, and how to adapt — and that, in my book, is pitching in its purest form. The Human vs. AI Paradox I wanted Chris on the show not because we needed another AI hype session, but because he’s refreshingly candid about what AI can and can’t do — especially when it comes to human connection. As someone who lives at the sharp edge of emerging tech, Chris knows better than most how quickly AI is changing the landscape. But he’s also quick to remind us that pitching is, at its heart, a human conversation. In the episode, we dig into what happens when you bring AI into your pitch process — not as a replacement for your voice, but as a tool to shape ideas faster, polish drafts, and even pressure-test your slides from the audience’s perspective. Chris jokes that AI can do a lot of what he does, except stand on a stage and read the room in real time — and that’s precisely where your irreplaceable edge lives. Structured Unstructured: How Chris Pitches One of my favourite parts of this conversation is hearing Chris describe his so-called “structured unstructured mess” approach to pitching. He spends hours drafting and organising a story, often building 60 to 100 slides — but when he’s in front of an audience, he might only use ten. He never hands his slides over beforehand and never locks himself into a rigid order. Instead, he pivots and responds based on audience signals: who’s leaning in, who’s drifting off, and where the energy is heading. This is such an important lesson for anyone who feels chained to a script. The real magic of pitching, as Chris shows, is that you can only plan so much. The rest is reading the room and trusting your expertise. AI as Your Pitch Assistant We also talk about how to use AI as your behind-the-scenes pitch helper. Chris outlines practical ways to record your pitch, get an instant transcript, and ask AI to summarise or restructure it in seconds. He calls this an incredible time-saver — freeing you up to focus on the parts AI can’t replicate: your tone, your delivery, and the emotional arc of your story. We get into real tools too: from ChatGPT for quick structure drafts, to ‘deep research’ prompts for gathering audience insights, to using AI as a virtual focus group to test whether your message lands. What struck me is that none of this replaces a good pitch — it just cuts the grunt work, so you can spend more time crafting moments that resonate. What to Watch For Of course, there’s a darker side too: we touch on what happens when AI-generated content starts feeding itself — the so-called ‘model collapse’ problem — and how to make sure your pitches don’t get lost in a sea of generic AI sludge. Chris’s advice? Be hyper-specific, both in your prompts and your message. AI can generate structure, but it can’t copy your lived experience, your stories, or the way you read an audience’s vibe in the room. A Few Takeaways Throughout our chat, Chris drops nuggets worth scribbling down: Don’t skip the prep: The best ‘improvised’ pitches rest on solid planning.Loosen up: Trust your knowledge enough to pivot live.Use AI as a partner, not a replacement: It’s your fastest assistant, not your stand-in.Keep it human: People show up for you, not your deck. Wrapping Up If you’re curious about how to future-proof your pitching skills in an AI world — or you just want permission to ditch your slide prison — this episode is for you. Chris reminds us that no matter how smart our tools get, pitching will always be an act of human connection, improvisation, and empathy. If you enjoy the conversation, don’t forget to grab a copy of PITCH: How to Captivate and Convince Any Audience on the Planet. It expands on these ideas with real stories, actionable frameworks, and a fresh approach to making your next pitch feel more like a conversation than a performance. Listen now — and let me know what you think. I promise it’s more fun than watching an AI pitch to another AI (although we cover that too!). You can find Chris at his YouTube channel: https://www.youtube.com/@chrishayuk
    Show More Show Less
    1 hr and 17 mins
  • S2 E02 VIDEO VERSION:Chris Hay, AI Technologist & Futurist

    S2 E02 VIDEO VERSION:Chris Hay, AI Technologist & Futurist
    Jun 22 2025
    Chris Hay, AI Technologist & Futurist When it comes to pitching, most people think about perfect slides, rehearsed lines, and the sweaty palms that come with trying to stick the landing. But as anyone who’s seen Chris Hay in action will tell you, great pitching rarely looks like a rigid script — and increasingly, it doesn’t happen without a little help from artificial intelligence. Chris and I know each other well through our time at IBM, where I’ve watched him pitch complex ideas to huge audiences without ever appearing tied to a slide deck. He describes himself as a “technologist, futurist and disruptor” — and if you listen to this episode, you’ll quickly see why. While he humbly claims he doesn’t ‘do pitching’, what he actually does is convince people to think differently about technology, the future, and how to adapt — and that, in my book, is pitching in its purest form. The Human vs. AI Paradox I wanted Chris on the show not because we needed another AI hype session, but because he’s refreshingly candid about what AI can and can’t do — especially when it comes to human connection. As someone who lives at the sharp edge of emerging tech, Chris knows better than most how quickly AI is changing the landscape. But he’s also quick to remind us that pitching is, at its heart, a human conversation. In the episode, we dig into what happens when you bring AI into your pitch process — not as a replacement for your voice, but as a tool to shape ideas faster, polish drafts, and even pressure-test your slides from the audience’s perspective. Chris jokes that AI can do a lot of what he does, except stand on a stage and read the room in real time — and that’s precisely where your irreplaceable edge lives. Structured Unstructured: How Chris Pitches One of my favourite parts of this conversation is hearing Chris describe his so-called “structured unstructured mess” approach to pitching. He spends hours drafting and organising a story, often building 60 to 100 slides — but when he’s in front of an audience, he might only use ten. He never hands his slides over beforehand and never locks himself into a rigid order. Instead, he pivots and responds based on audience signals: who’s leaning in, who’s drifting off, and where the energy is heading. This is such an important lesson for anyone who feels chained to a script. The real magic of pitching, as Chris shows, is that you can only plan so much. The rest is reading the room and trusting your expertise. AI as Your Pitch Assistant We also talk about how to use AI as your behind-the-scenes pitch helper. Chris outlines practical ways to record your pitch, get an instant transcript, and ask AI to summarise or restructure it in seconds. He calls this an incredible time-saver — freeing you up to focus on the parts AI can’t replicate: your tone, your delivery, and the emotional arc of your story. We get into real tools too: from ChatGPT for quick structure drafts, to ‘deep research’ prompts for gathering audience insights, to using AI as a virtual focus group to test whether your message lands. What struck me is that none of this replaces a good pitch — it just cuts the grunt work, so you can spend more time crafting moments that resonate. What to Watch For Of course, there’s a darker side too: we touch on what happens when AI-generated content starts feeding itself — the so-called ‘model collapse’ problem — and how to make sure your pitches don’t get lost in a sea of generic AI sludge. Chris’s advice? Be hyper-specific, both in your prompts and your message. AI can generate structure, but it can’t copy your lived experience, your stories, or the way you read an audience’s vibe in the room. A Few Takeaways Throughout our chat, Chris drops nuggets worth scribbling down: Don’t skip the prep: The best ‘improvised’ pitches rest on solid planning.Loosen up: Trust your knowledge enough to pivot live.Use AI as a partner, not a replacement: It’s your fastest assistant, not your stand-in.Keep it human: People show up for you, not your deck. Wrapping Up If you’re curious about how to future-proof your pitching skills in an AI world — or you just want permission to ditch your slide prison — this episode is for you. Chris reminds us that no matter how smart our tools get, pitching will always be an act of human connection, improvisation, and empathy. If you enjoy the conversation, don’t forget to grab a copy of PITCH: How to Captivate and Convince Any Audience on the Planet. It expands on these ideas with real stories, actionable frameworks, and a fresh approach to making your next pitch feel more like a conversation than a performance. Listen now — and let me know what you think. I promise it’s more fun than watching an AI pitch to another AI (although we cover that too!). You can find Chris at his YouTube channel: https://www.youtube.com/@chrishayuk
    Show More Show Less
    1 hr and 17 mins
  • S2 E01: Daniel H. Pink, 7x NYT bestselling author

    S2 E01: Daniel H. Pink, 7x NYT bestselling author
    May 11 2025

    Daniel H. Pink, bestselling author and expert on human behaviour, joins the show to explore the art and science of persuasion. He shares how modern sales is less about manipulation and more about attunement, buoyancy, and clarity—three traits vital in today’s world of information parity. Pink also discusses the surprising power of ambiverts, the myth of extroverted sales stars, and how regret can drive personal growth. With practical insights and research-backed tips, this episode redefines pitching as a collaborative act rooted in empathy and understanding.

    When I first started out in the world of pitching, I was terrible. It wasn't a career I’d ever imagined for myself. Like many people, I had a perception of sales as something manipulative and disingenuous—the classic 'used car salesman' trope, full of slick tricks and empty charm.

    Luckily for me, I stumbled on a book that changed everything: To Sell is Human: The Surprising Truth About Persuading, Convincing, and Influencing Others by Daniel H. Pink.

    It reframed sales not as something pushy or performative, but as something deeply human. At its best, persuasion isn't about control—it's about connection.

    So when I launched Pitch Masters, Dan Pink was at the top of my dream guest list. And I’m delighted to finally share this conversation with someone whose thinking shaped my approach not just to pitching, but to communication in every part of life.

    This isn’t just a conversation about sales or writing—it’s about how humans move each other.

    We dive into why most of us are selling all the time, even if we don’t realise it. Daniel explains why the old image of the pushy, silver-tongued salesperson is completely outdated—and how modern persuasion is built on empathy, emotional resilience, and making sense of information in a noisy world.

    You’ll hear about the surprising science behind what really works in a pitch:

    • Why ambiverts (yes, not extroverts) outperform everyone else.
    • The sweet spot for making a persuasive argument (hint: stop at three points).
    • The moment Daniel realised a great pitch isn’t a performance—it’s an invitation.
    • How AI is like a mediocre colleague with one good idea—and that’s enough to unblock you.
    • And why regret, of all things, might be your most powerful teacher.

    Whether you’re trying to influence a room, sell an idea, or just get your kids out the door, this episode will make you think differently about what it means to pitch.

    Final Thought

    Whether you’re a seasoned presenter, a nervous first-time founder, or someone who just wants to express yourself better, this episode will change how you think about pitching.

    Dan Pink doesn’t give you a script. He gives you a mindset. And once you adopt it, you’ll never pitch the same way again.

    🎧 Listen now to my conversation with Daniel H. Pink on Pitch Masters. Because pitching isn’t just for salespeople—it’s for anyone who wants to move others, honestly and effectively.

    If you enjoy the show, reviews, ratings and shares are the best possible way to show your support and are always appreciated. Sign up for the mailing list for exclusive content at http://pitchguy.co.uk/ and follow me on social media for video clips of the episode.

    Instagram: https://www.instagram.com/dannyfontaine/

    TikTok: https://www.tiktok.com/@pitchguy

    YouTube: https://www.youtube.com/@pitchguy/

    Linkedin: https://www.linkedin.com/in/dannyfontaine/

    My own book, Pitch: How to Captivate and Convince Any Audience on the Planet, is now available for pre-order: https://amzn.eu/d/ewuiZ53
    Show More Show Less
    56 mins
All stars
Most relevant  
if you want to hear about pure agency pitching this is the episode for you

another cracking episode in this excellent series

Something went wrong. Please try again in a few minutes.