

Why That Worked – Presented by StoryBrand.ai
StoryBrand.ai
Welcome to Why That Worked – Presented by StoryBrand.ai. Have you ever wondered why some brands, trends, or products become massive successes while others fade away? That’s exactly what this podcast explores. Hosted by Donald Miller, creator of the StoryBrand Framework, and co-hosted by Kyle Reed, each episode dives into the strategies behind the world’s biggest wins, breaking them down into clear, actionable insights you can use to create your own success.
Discover how to craft clear and effective messaging that works for your business at StoryBrand.ai.
Discover how to craft clear and effective messaging that works for your business at StoryBrand.ai.
Episodes
Mentioned books

Aug 11, 2025 • 38min
#32: Southwest—The Genius of ‘Bags Fly Free’ and What Happened When It Changed (RE-RELEASE)
Hopefully you're getting a chance to recharge this summer—but that doesn’t mean you have to lose momentum. Fall is just around the corner, and before you know it we’ll be heading into the final stretch of the year. That’s exactly why we’re rereleasing several of our high-impact episodes—designed to give you clarity, sharpen your message, attract the right customers, and ultimately drive more revenue, so you’re not stuck playing catch-up when it matters most! -- Southwest Airlines built one of the strongest brands in the world by doing one thing better than almost anyone: clear, clever messaging that made customers feel like family. “Bags fly free” was more than a tagline. It was a promise that set them apart from every other airline. But when they recently backtracked on that core message, the backlash was instant. In a world where loyalty is fragile and expectations are sky-high, even the best brands can stumble if they don’t communicate the right way. So what happens when a company known for brilliant messaging gets it wrong? In this week’s episode, Don and Kyle unpack the marketing brilliance that made Southwest an iconic brand and why their latest messaging misstep is such a big deal. They reveal how Southwest’s playful, people-first branding created an unbeatable bond with customers, and how this new shift risks breaking that trust. You'll learn what Southwest could have done differently, why your messaging must evolve without abandoning what made you great, and how to communicate tough changes without losing customer loyalty. Tune in to find out how even a beloved brand can slip and how you can avoid making the same mistake. -- Click HERE to find a StoryBrand certified marketing coach to help you grow your business! Unlock the power of a framework that works—the StoryBrand Framework at StoryBrand.ai. It's like having the world’s best copywriter create high-converting marketing whenever you need it. Start your free 7-day trial at StoryBrand.ai. Learn how to make your marketing and messaging work using a proven framework in the updated book, Building a StoryBrand 2.0. Order it now on Amazon or wherever you buy books!

Aug 4, 2025 • 40min
#31: Airbnb—The Brilliant Strategy Behind Their New Messaging Campaign (RE-RELEASE)
Hopefully you're getting a chance to recharge this summer—but that doesn’t mean you have to lose momentum. Fall is just around the corner, and before you know it we’ll be heading into the final stretch of the year. That’s exactly why we’re rereleasing several of our high-impact episodes—designed to give you clarity, sharpen your message, attract the right customers, and ultimately drive more revenue, so you’re not stuck playing catch-up when it matters most! -- If your marketing isn’t working, it’s probably because you’re not talking about the right problem. Most businesses struggle to identify the most compelling issue their customer is trying to solve. They either talk about too many things or pick a problem that’s too vague. When that happens, customers stop listening. But when you finally address the problem that makes your customers say “yep, that’s me!”, sales start to climb. That's what Airbnb just nailed with their new messaging campaign. So, how do you figure out the exact problem your business solves in a way that drives real results? In this episode, Don and Kyle break down Airbnb’s latest messaging campaign and why it hits the mark so effectively. They unpack the brilliance behind how Airbnb redefined the problem it solves and how you can apply the same strategy to your own business. You’ll learn a simple way to clarify the problem your customer actually cares about and how to build an effective messaging campaign around it. Listen in for strategic tips on how to get sharper messaging and more customer engagement. -- Click HERE to find a StoryBrand certified marketing coach to help you grow your business! Unlock the power of a framework that works—the StoryBrand Framework at StoryBrand.ai. It's like having the world’s best copywriter create high-converting marketing whenever you need it. Start your free 7-day trial at StoryBrand.ai. Learn how to make your marketing and messaging work using a proven framework in the updated book, Building a StoryBrand 2.0. Order it now on Amazon or wherever you buy books!

7 snips
Jul 28, 2025 • 33min
#30: AI with Jay Owen—How Smart Businesses Use It Without Losing the Human Touch
In this discussion, Jay Owen, founder of AI with Jay and a StoryBrand certified agency owner, reveals how small businesses can harness AI without sacrificing their unique voice. He emphasizes the need for skepticism and critical thinking when using AI tools, while also exploring how these technologies can enhance creativity rather than replace it. Jay shares insights on maintaining genuine human connections in an AI-driven world and offers practical strategies for integrating AI into business communication and brand messaging.

Jul 21, 2025 • 29min
#29: Infomercials—What OxiClean & Shamwow Can Teach Us About Messaging That Sells
Infomercials, often seen as cheesy, hold powerful lessons in sales clarity and urgency. The dynamic pitches of OxiClean and ShamWow reveal the effectiveness of bold language and strong calls to action. Learn how dramatic presentations and memorable soundbites capture consumer attention. The hosts explore how cost comparisons and clear demonstrations drive decisions. Discover why clarity in messaging outshines cleverness, and unlock the secrets to crafting engaging pitches that can elevate your brand to billion-dollar success.

Jul 14, 2025 • 43min
#28: John Mark McMillan—How to Make Promotion a Part of the Creative Process
The biggest challenge creative people face isn’t making something meaningful, it’s figuring out how to share it without feeling like a sellout. Whether you’re an artist, entrepreneur, or thought leader, there comes a point when the art alone isn’t enough. You realize that if your work is going to make an impact, you have to learn how to promote it. But how do you do that without compromising your voice or turning into a walking ad? In this episode, musician and songwriter John Mark McMillan joins hosts Donald Miller and Kyle Reed to unpack that exact tension. With more than 20 years of music and 10 albums behind him, John Mark shares how he finally merged the art and the business without losing his authenticity. You’ll hear his story of personal and creative transformation, how he learned to lead his own vision, and why real connection (not just attention) is what makes art last. Click HERE to find a StoryBrand certified marketing coach to help you grow your business! -- Unlock the power of a framework that works—the StoryBrand Framework at StoryBrand.ai. It's like having the world’s best copywriter create high-converting marketing whenever you need it. Start your free 7-day trial at StoryBrand.ai. Learn how to make your marketing and messaging work using a proven framework in the updated book, Building a StoryBrand 2.0. Order it now on Amazon or wherever you buy books!

Jul 7, 2025 • 21min
#27: Bombas—The Shark Tank Pitch That Got Everything Right (And What Businesses Can Learn From It)
Discover the secret sauce behind Bombas' successful pitch on Shark Tank that transformed them into a billion-dollar brand. The hosts break down how effective storytelling, catchy soundbites, and emotional connections captivated the Sharks and customers alike. Learn how Bombas revolutionized sock marketing through relatable language and innovative features. They also highlight the importance of strategic funding and clear messaging. Tune in for fantastic insights on crafting memorable pitches that resonate!

Jun 30, 2025 • 31min
#26: Dan Go—The Fitness Coach Who Built a Mega Brand by Niching Down
Discover the power of niching down in personal branding. A focused message builds trust and establishes authority faster than a broad approach. Learn from Dan Go, a fitness coach who zeroed in on entrepreneurs, and understand how clarity in communication can enhance engagement. The podcast shares strategies to master niche marketing and why authenticity and motivational content are key. Embrace the journey of aging positively while honing in on your target audience to create a compelling brand presence.

7 snips
Jun 23, 2025 • 41min
#25: Annie F. Downs—The Strategy Behind Her Breakthrough Personal Brand
Join bestselling author and speaker Annie F. Downs, known for her podcast 'That Sounds Fun', as she discusses the essence of crafting a personal brand rooted in authenticity. She shares how vulnerability and personal stories foster genuine connections. Discover her 'controlling idea' that shapes her messaging and the delicate balance between sharing enough and protecting one’s well-being on social media. Annie offers insights on prioritizing mental health while staying engaging, proving that being real is the ultimate strategy.

Jun 16, 2025 • 28min
#24: Pass/Fail—Breaking Down the Best and Worst in Branding
Dive into the world of branding where messaging can either build trust or shatter it. Explore Shedeur Sanders' bold comments and the fine line between confidence and arrogance in sports branding. Discover the shift towards employee-generated content and how it enhances authenticity. Learn why user-generated reviews carry more weight than company messages, along with inventive strategies that engage audiences. This discussion uncovers the secrets to creating compelling content that resonates and drives connection.

Jun 9, 2025 • 46min
#23: Dadville—The New Rules of Being a Great Dad
Dads often get a bad rap. In sitcoms, commercials, and even day-to-day culture, they’re typically cast as bumbling sidekicks or lovable oafs who mean well but don’t quite get it right. When that narrative takes root, it can be easy for fathers to shrug and settle for doing the bare minimum (especially when they get praise for just pushing a stroller down the street). But kids need more. And deep down, every dad knows he was made for more. So what does it look like to embrace fatherhood with purpose, presence, and even a little swagger? In this special Father’s Day episode, Don and Kyle sit down with Dave Barnes and John McLaughlin, hosts of the hit podcast Dadville. Together, they explore the most important messages a father can send his kids. They break down why dad-messaging matters, what it looks like in the real world, and how even small changes in tone or presence can echo for generations. If you’re a dad, or want to be one, listen in for a refreshing take on what it really means to show up for your family. Check out the Dadville Podcast HERE ! -- Unlock the power of a framework that works—the StoryBrand Framework at StoryBrand.ai. It's like having the world’s best copywriter create high-converting marketing whenever you need it. Start your free 7-day trial at StoryBrand.ai. Learn how to make your marketing and messaging work using a proven framework in the updated book, Building a StoryBrand 2.0. Order it now on Amazon or wherever you buy books!