S2 E06: Terry Szuplat, Former Obama Speechwriter and Bestselling Author

What can business leaders learn from the pressure, craft, and discipline of presidential speechwriting?  In this episode of Pitch Masters, I sit down with Terry Szuplat, who spent nearly a decade as a speechwriter for President Barack Obama, to unpack what makes messages land, what makes audiences lean in, and why “generic” is the fastest route to being forgotten. Terry takes us inside the realities of writing for the most scrutinised speaker on the planet, shares the practical framework he uses to help leaders prepare talks and pitches, and offers a simple principle that instantly raises the bar: say what only you can say.   Connect with Terry Szuplat Website: https://www.terryszuplat.com/ LinkedIn: https://www.linkedin.com/in/terry-szuplat-456914137/ 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 book, Pitch: How to Captivate and Convince Any Audience on the Planet, is now available: https://amzn.eu/d/ewuiZ53

Why do talented professionals get stuck in mid-level roles even when they’re doing great work? In this episode of Pitch Masters, I sit down with executive presence expert, keynote speaker, and author Lorraine K. Lee to explore why hard work alone isn’t enough to grow your career. Lorraine shares the moment she realised that visibility, not just performance, was the missing ingredient in her own journey from LinkedIn and Prezi to launching her own successful business.  We dive into: Why “hard work speaks for itself” is a myth How to build executive presence in hybrid and virtual environments The RAVE framework (Relationships, Appearance, Visibility, Expertise) How introverts can lead powerfully without pretending to be extroverts How to communicate your value without sounding like you’re bragging Why eye contact and storytelling matter more than slides If you want to influence more effectively, pitch with confidence, and build a reputation that accelerates your career — this episode is for you. Connect with Lorraine K. Lee: Website: https://lorraineklee.com/ LinkedIn: https://www.linkedin.com/in/lorraineklee/ 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 book, Pitch: How to Captivate and Convince Any Audience on the Planet, is now available: https://amzn.eu/d/ewuiZ53

What separates the world’s best communicators from everyone else? In this episode of Pitch Masters, I sit down with Oliver Aust —former easyJet Chief Communicator, bestselling author, and founder of Speak Like a CEO — to talk about how leaders can pitch, persuade, and present with authenticity. From stories of easyJet’s scrappy early days to his philosophy of anti-fragile communication, Oliver shares practical insights on storytelling, structure, and confidence. His advice is simple yet profound: be cool, be helpful, be flexible. To find out more about the Speak Like A CEO Academy, podcast or books, visit Oliver’s website and become a top 1% communicator.  You can also find Oliver on Linkedin here. If you enjoy the conversation, don’t forget to grab a copy of my book: PITCH: How to Captivate and Convince Any Audience on the Planet. You can also find more free content and resources on my website: pitchguy.co.uk And find me on Social Media here:   Linkedin TikTok Instagram   Thanks for listening. Danny.    #PitchMasters #OliverAust #easyjet #Pitching #presenting #Storytelling #Communication #PublicSpeaking #Leadership #Pitching #SpeakLikeACEO #Marketing #PresentationSkills #Creativity #BusinessStorytelling #Confidence #DannyFontaine

In this compelling episode of Pitch Masters, I sit down with Julian Treasure, renowned sound and communication expert, author, and five-time TED speaker whose talks have collectively been viewed over 160 million times. Julian reveals why listening, not just speaking, is critical in business, pitches, and leadership. Drawing from his new book, Sound Affects, we explore the profound impact of sound and listening on our personal effectiveness, organisational success, and even global economics. Tune in to learn how genuinely tuning in can transform your next pitch and beyond. For more insights, explore Julian’s book Sound Affects, or join his online community, The Listening Society, where you’ll get a whole month for free with this link. 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.

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   

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

The pitch to become British Rail’s advertising agency in 1979 is one of the greatest of all time. It involved an immersive theatrical experience that showed an audience a problem in a completely new light. The story has been told to me many times by many people, but always with a different spin. I decided to find out the truth for myself and tracked down Graham Thomas, who was – in 1979 – an Account Manager for Allen, Brady & Marsh, and played a vital role in this now-legendary pitch.  In this episode, he talks me through the pitch itself as well as taking me on a journey behind-the-scenes of the clandestine world of 1970's advertising. Wire-tapped mini-cabs, walkie-talkies, buttering up hotel porters, theatrics and playbooks - this episode is 80 minutes of pitching GOLD. 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/

Oren Klaff is the real deal. He raises vast sums of investment capital every single day using his unique and hugely popular methods of pitching - as outlined in his international bestselling book, Pitch Anything: An Innovative Method for Presenting, Persuading, and Winning the Deal. We talk about a LOT of topics: swagger, making money, persuasion, human behaviour, capital markets, Anthony Scaramucci, cognitive psychology, power hierarchies and status, billionaires and valets, values, and negotiating - and we even do some role play. WARNING - there is some fairly explicit and expletive language throughout this episode, but if you’re ok with that, grab a drink, sit back, and get ready to take notes. 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/

In this episode of the Pitch Masters podcast, I speak to yet another one of my all-time pitching heroes, the legendary Peter Coughter, founder and CEO of Coughter & Company, Professor at VCU Brandcenter, and author of one of my favourite books - The Art of the Pitch: Persuasion and Presentation Skills that Win Business. In this episode, we discuss a lot of pitch material - the fear we all have, whether we need a deck, bringing the right people, and breaking the rules. But, best of all, Peter is a natural-born storyteller, and this episode is packed to the brim with pitch anecdotes that will make you laugh and cry. He tells me how he helped the Boston Olympic Committee win the honour of being the US City of choice to be put forward for the 2024 Summer Olympics, by employing a highly emotional and heartfelt story about the Boston Marathon Bombings. He tells me the story of how he used a scene from Conan Barbarian to win the hearts and minds of a business that were strongly opposed to his agency. He also tells me the hilarious story of a pitch that went horrendously wrong in a hotel when the slide projectors became effected by the pushing of buttons in the elevator. He tells me a lot of great stories. 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/   Sit back, grab a drink, and get ready to take notes…

You've probably heard of the power of storytelling in business, but how do we actually go about doing it - and do we need to be a natural-born storyteller? Enter, Hilary Salzman, the Business Storyteller.    Hilary is the founder of 22-stories.com and she's on a mission to get more people telling stories to grow their business. In this episode of Pitch Masters, we talk about why we should tell stories in business, the science behind creating emotional connections, and frameworks that you can immediately start using to create your own compelling stories. We also talk about the challenges that women face in male-dominated industries, overcoming imposter syndrome, and we have an open discussion on whether ChatGPT has a role in storytelling. You can connect with Hilary on her website, Instagram, and Linkedin, and I would HIGHLY recommend her Podcast, The Everyday Storyteller.   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/   Sit back, grab a drink, and get ready to take notes…