Milestone Moments in Business & Leadership

What if the secret to marketing that actually converts has nothing to do with the latest AI tool or trending strategy? Rachel Allen built a global copywriting career across 21 countries starting with $200, a one-way ticket to Hong Kong, and a $3.25 freelance gig. In this episode, Rachel reveals the one AI mistake most marketers are making right now, why your human voice is your most underutilized asset, and the dead-simple action you can take today that most business owners completely neglect.If your marketing feels like it sounds like everyone else's, you need to hear this.Tune in now wherever you listen to podcasts.To connect with Rachel Allen, visit boltfromthebluecopywriting.com or connect with her on LinkedIn.Stay connected! Subscribe to Sheila's newsletter for early access to upcoming episodes, expanded strategies, and direct support.Subscribe to the Newsletter: https://fivemilestones.kit.com/newsletter Connect on LinkedIn: https://www.linkedin.com/in/sheilaslick/ Subscribe on YouTube: https://www.youtube.com/@fivemilestonesFive Milestones: https://fivemilestones.com/show/Sponsored by PodToBook.ai | Turn Your Podcast Conversations into a Book

What if the thing holding you back from launching isn't your expertise, it's your definition of ready?Jake Wysocki spent years training hundreds of professionals inside Fortune 200 companies before one conversation with his wife changed everything. He walked away from a job he loved, skipped the side hustle, and built something entirely new. But the path that followed wasn't straight, and what he discovered along the way reframed how he thinks about programs, perfection, and the cost of waiting.In this episode, Jake breaks down why chasing perfection is the wrong goal entirely, and what to pursue instead. He also shares the low-risk strategy he borrowed from Jim Collins that every entrepreneur needs before going all in on a big idea.If you've been telling yourself "I'll do it someday," this episode will make you rethink that timeline.Tune in now and catch this episode on your favorite podcast platform.To connect with Jake Wysocki, visit workshopy.comStay connected! Subscribe to Sheila's newsletter for early access to upcoming episodes and events, expanded strategies and resources, and direct connection with Sheila for questions and support.Subscribe to the Newsletter: https://fivemilestones.kit.com/newsletter Connect on LinkedIn: https://www.linkedin.com/in/sheilaslick/ Subscribe on YouTube: https://www.youtube.com/@fivemilestonesFive Milestones: https://fivemilestones.com/show/Sponsored by PodToBook.ai | Turn Your Podcast Conversations into a Book

What if everything you've been told about burnout recovery is missing the most important piece?Samantha Catone spent eight years as a litigation attorney doing everything "right" — whole foods, meditation, specialists, supplementation — and still watched her health collapse completely. What she discovered on the other side wasn't another wellness hack. It was something far more fundamental, and it changed everything.In this episode of Milestone Moments in Business and Leadership, former attorney turned burnout coach Samantha Catone shares the surprising truth she uncovered when conventional advice stopped working — and how the very traits that made her successful were quietly working against her. What happened when she finally stopped looking for answers outside herself? The results were unexpected.If you're a high achiever running on empty and wondering why nothing seems to work, this conversation might be the turning point you didn't know you needed.Listen in to learn more about burnout recovery for high achievers, nervous system regulation, and rebuilding self-worth after burnout.To connect with Samantha Catone, visit sammycatone.comStay connected! Subscribe to Sheila's newsletter for early access to upcoming episodes and events, expanded strategies and resources, and direct connection with Sheila for questions and support.Subscribe to the Newsletter: https://fivemilestones.kit.com/newsletter Connect with me on LinkedIn: https://www.linkedin.com/in/sheilaslick/ Subscribe on YouTube: https://www.youtube.com/@fivemilestones For more information, visit: Sheila Slick: https://sheilaslick.com Five Milestones: https://fivemilestones.com/show/Sponsored by: https://PodToBook.ai | Turn Your Podcast Conversations into a Book

What if everything you're working toward is actually taking you further from the life you want? Gwen Bortner has spent four decades and 47 industries watching business owners hit their goals and still end up burned out, disconnected, and quietly miserable.As an operational strategist and business advisor, Gwen asks one deceptively simple question that most entrepreneurs can't actually answer. And until you can, no system, hire, or strategy will fix what's really wrong.In this episode, she challenges the definition of success you've been chasing, reframes what burnout is actually about, and shares a one-word swap in how you ask questions that instantly shifts your brain from defensiveness to problem-solving mode.This episode will make you rethink what you're building and why.Tune in now wherever you listen to podcasts.To connect with Gwen Bortner, visit gwenbortner.com or connect with her on LinkedIn.Stay connected! Subscribe to Sheila's newsletter for early access to upcoming episodes, expanded strategies, and direct support.Subscribe to the Newsletter: https://fivemilestones.kit.com/newsletter Connect on LinkedIn: https://www.linkedin.com/in/sheilaslick/ Subscribe on YouTube: https://www.youtube.com/@fivemilestones Five Milestones: https://fivemilestones.com/show/Sponsored by PodToBook.ai | Turn Your Podcast Conversations into a Book

What happens when a combat veteran, space operations specialist, and math teacher picks up a pen — and uncovers an ancestor who lost everything at 22, yet was remembered as one of the most dignified women of her era?Joseph Bolton spent years chasing a mystery hidden behind his French-Canadian, Native American, Spanish, English, and Irish roots. What he found in the archives of 17th-century Quebec stopped him in his tracks — and ignited a book series that readers of all ages can't put down.In this episode, Joseph shares how a real Algonquin woman named Mirimete Ouagwe — whose story was nearly lost to history — became the beating heart of his Old Grandmother's Tree series. Told in the language of folktales, woven with trickster animals and a little magic, these stories carry truths about family, resilience, and legacy that feel surprisingly universal.And there's one chapter — a conversation between an old turtle and a young moose — that might just be the most quietly powerful thing you'll hear all year.🎧 Tune in now — some stories are too important to forget.To connect with Joseph Bolton, visit oldgrandmotherstree.comStay connected! Subscribe to Sheila's newsletter for early access to upcoming episodes and events, expanded strategies and resources, and direct connection with Sheila for questions and support.📩 Subscribe to the Newsletter 💼 Connect on LinkedIn ▶️ Subscribe on YouTube 🌐 Sheila Slick | Five Milestones✨ Sponsored by PodToBook.ai | Turn Your Podcast Conversations into a Book

What if the gap between where you are and where you want to be isn't about skill, it's about what you're doing when no one's watching?Sabine Kvenberg spent decades as a stage and TV actress in Germany, a director, and a performing arts school founder before bringing those hard-won performance secrets into the business world. She didn't just study communication. She lived it on real stages, in real auditions, with real stakes.In this episode, Sabine introduces a concept that might reframe everything about how you show up in your business. She calls it the invisible stage, and it's where influence is actually built long before anyone sees you. She also breaks down what it really takes to become a "triple threat" in your industry, and why the experts who skip this step stay invisible no matter how good they are.If you've been waiting for the right moment to step into your authority, this episode will make you rethink what "ready" actually means.Tune in now on your favorite podcast platform.To connect with Sabine Kvenberg, visit sabinekvenberg.com/resources or schedule a conversation at talktosabine.comStay connected! Subscribe to Sheila's newsletter for early access to upcoming episodes and events, expanded strategies and resources, and direct connection with Sheila for questions and support.Subscribe to the Newsletter: https://fivemilestones.kit.com/newsletter Connect on LinkedIn: https://www.linkedin.com/in/sheilaslick/ Subscribe on YouTube: https://www.youtube.com/@fivemilestonesFive Milestones: https://fivemilestones.com/show/Sponsored by PodToBook.ai | Turn Your Podcast Conversations into a Book

What if the thing holding you back from video isn't your gear, your lighting, or your editing skills — but something far more fixable?Sarah Berry spent 20 years as a corporate trainer before discovering that the same skills that made her valuable inside companies could build something iconic outside of them. But first, she had to survive the cringe. Her unconventional experiment changed everything — and the results were nothing like she expected.In this episode, Sarah reveals why most people approach video content completely backwards, the mindset shift that separates those who gain traction from those who quit at episode three, and the surprisingly low-effort strategy she now teaches through her program, Invisible to Iconic.If you've been waiting until you feel "ready" to show up on camera, this episode will challenge everything you think you know about what's actually stopping you.Tune in now and discover what's possible when you stop overthinking and start recording.To connect with Sarah Berry, visit her on LinkedIn.Stay connected! Subscribe to Sheila's newsletter for early access to upcoming episodes, expanded strategies, and direct support.Subscribe to the Newsletter | LinkedIn | YouTubeSheila Slick | Five MilestonesSponsored by PodToBook.ai | Turn Your Podcast Conversations into a Book

Your Voice Could Be Your Most Valuable Business Asset , Are You Still Keeping It Silent? with Harry DuranWhat if the podcast you've been putting off could become your most powerful business development tool? Harry Duran, founder of Fullcast and host of 500+ episodes across multiple shows, didn't just build a podcast — he built an entirely new life with one. But it wasn't until a near-death experience on a waterfall in Thailand that he discovered the real reason he does it all.In this episode, Harry reveals the counterintuitive strategy that landed him a sponsor before he recorded a single episode — and how he turned a niche interest into a six-figure revenue stream. He also shares what most new podcasters get dangerously wrong about SEO, and why the answer isn't more content.What would you do differently if you knew your podcast could open doors you never expected? What's the one element Harry says determines whether a show succeeds or quietly disappears?Tune in and find out why Harry believes your voice is too important to keep inside.🎧 Listen to the full episode now!To connect with Harry Duran, visit fullcast.coStay connected! Subscribe to Sheila's newsletter for early access to upcoming episodes and events, expanded strategies and resources, and direct connection with Sheila for questions and support.📩 Subscribe to the Newsletter 🔗 Connect on LinkedIn ▶️ Subscribe on YouTube 🌐 Sheila Slick | Five MilestonesSponsored by PodToBook.ai | Turn Your Podcast Conversations into a Book

What if the biggest threat to your sales team isn't the competition—but the complete lack of leadership development that's silently crushing performance?Rebecca Gebhardt, former top 1% sales leader who generated over $50 million in revenue, exposes a shocking industry secret that's costing companies millions. After burning out at 33 despite loving her job, Rebecca discovered something that fundamentally changed how she views sales leadership development."80% of sales leaders are given zero training once being promoted," Rebecca reveals. "The average person gets their first leadership promotion at age 30, but their first leadership development at age 42. That's 12 years of trial and error."Here's what will stagger you: While companies spend fortunes on sales training, they're completely ignoring the one factor that determines whether any of it actually works. Rebecca shares why even the best sales programs fail—and it has nothing to do with the content.What you'll discover in this episode:Why high performers are actually at higher risk for dangerous burnoutThe brutal truth about how organizations measure training effectivenessHow Rebecca went from "terrible" at sales to building million-dollar teamsWhy strength-based coaching gives sales teams an unfair competitive advantageThe assessment that reveals your sales team's hidden potential (and can be used in interviews)Why women wait for 100% confidence while men leap at 60%—and what this means for your teamBut here's the game-changing revelation: What happens when you discover that most "personality conflicts" aren't personality issues at all—but something much deeper that can be completely resolved?Rebecca reveals her strength-based framework using tools that measure what traditional assessments miss entirely. One assessment focuses on the "do" part of the brain that's completely subconscious, while another predicts whether leaders will thrive or merely survive.The breakthrough moment that changes everything? When Rebecca explains why someone selling medical devices would fail in her role, and vice versa—and how understanding this prevents costly hiring mistakes and team frustrations.Ready to discover what's really driving (or destroying) your sales team's performance?To connect with Rebecca Gebhardt, visit riseupconsultinggroup.com or find her on LinkedInStay connected! Subscribe to Sheila's newsletter for:Early access to upcoming episodes and eventsExpanded strategies and resourcesDirect connection with Sheila for questions and supportSubscribe to the Newsletter: https://fivemilestones.kit.com/newsletter Connect with me on LinkedIn: https://www.linkedin.com/in/sheilaslick/ Subscribe on YouTube: https://www.youtube.com/@fivemilestonesFor more information, visit: Sheila Slick: https://sheilaslick.com Five Milestones: https://fivemilestones.com/show/Sponsored by: https://PodToBook.ai | Turn Your Podcast Conversations into a Book

Dr. Angela Mulrooney, known as "The Arsonist," lost her thriving dental practice in an instant and watched her world burn down. But what she discovered while building five successful businesses from the ashes will change how you think about career pivots, AI, and the hidden crisis facing accomplished professionals today.Why are highly intellectual people being pushed out of corporations while those in their 70s are thriving as entrepreneurs? What's the shocking truth about multi-generational teams that companies are ignoring? And how did Angela turn a 12-hour manual process into an AI tool that reveals your "niche of genius" in minutes?Discover why calling yourself "former VP" or "former executive" is sabotaging your next chapter, how ageism is being disguised as AI disruption, and the one thing senior professionals must do before they lose their identity entirely. Angela reveals the surprising difference between pivoting and evolving—and why one leads to burnout while the other builds unstoppable momentum.Tune in to discover how to make yourself irreplaceable in the age of AI—and why your greatest asset isn't what you used to be, but who you're becoming. To connect with Dr. Angela Mulrooney, visit https://app.unleashinginfluence.com/v2 or find her on LinkedIn as Dr. Angela MulrooneyStay connected! Subscribe to Sheila's newsletter for:Early access to upcoming episodes and eventsExpanded strategies and resourcesDirect connection with Sheila for questions and supportSubscribe to the Newsletter: https://fivemilestones.kit.com/newsletter Connect with me on LinkedIn: https://www.linkedin.com/in/sheilaslick/ Subscribe on YouTube: https://www.youtube.com/@fivemilestonesFor more information, visit:Sheila Slick: https://sheilaslick.comFive Milestones: https://fivemilestones.com/show/Sponsored by: https://PodToBook.ai | Turn Your Podcast Conversations into a Book

Are you drowning in tasks that aren't really yours? What if the biggest leadership trap isn't about doing too much—it's about doing the wrong work entirely?Liz Weber, named one of 2025's Top Global Gurus for Leadership alongside Simon Sinek and John Maxwell, reveals a shocking truth that's been plaguing organizations for 30+ years: most leaders don't actually understand what their job is. But here's what's more surprising—neither do their teams.What happens when high performers unknowingly shoulder 125% of the workload while others coast at 75%? How does a training room conversation expose problems that senior leadership never sees? And why does being "helpful" actually sabotage your team's growth?Liz shares the unexpected journey from thinking she'd be a commodities broker to becoming a trusted advisor to C-suite executives and boards—and the pivotal classroom moment that changed everything. Discover the deceptively simple assessment that reveals whether you're stuck doing work below your level, and why the "easier to just do it myself" mentality is silently crushing your leadership potential.Tune in to discover the one question that exposes whether you're leading—or just enabling.To connect with Liz Weber, visit https://wbsllc.com or find her on LinkedIn at @LizWeberCMCStay connected! Subscribe to Sheila's newsletter for:Early access to upcoming episodes and eventsExpanded strategies and resourcesDirect connection with Sheila for questions and supportSubscribe to the Newsletter: https://fivemilestones.kit.com/newsletter Connect with me on LinkedIn: https://www.linkedin.com/in/sheilaslick/ Subscribe on YouTube: https://www.youtube.com/@fivemilestonesFor more information, visit:Sheila Slick: https://sheilaslick.comFive Milestones: https://fivemilestones.com/show/Sponsored by: https://PodToBook.ai | Turn Your Podcast Conversations into a Book

What if every problem you're frantically solving is actually making things worse?Vandana Piranek spent 25 years watching brilliant teams pour millions into solutions that missed the mark entirely—until a factory worker with a desk fan exposed the fatal flaw in how we think. After surviving a two-week coma and delivering her TEDx talk three days post-hospital, she decoded what separates leaders who thrive from those trapped in endless problem-solving cycles.Here's the unsettling truth: 95% of your daily thoughts are redundant. You're solving problems instead of outcomes. And that perfume manufacturer? They spent millions overhauling their production line when the answer cost less than $20.But there's a bigger question nobody's asking—the one Abraham Wald posed during WWII that saved countless lives by looking at what everyone else ignored. What are YOU not seeing?The gap between where you are and living limitless isn't about working harder. It's about upgrading your mental operating system. And it starts with one principle most people completely misunderstand.Tune in to discover the three principles that transform impossible situations into breakthrough moments.Connect with Vandana Piranek:Website: https://thebookofmight.comLinkedIn: Connect with Vandana PiranekStay connected!Subscribe to newsletter for:Early access to upcoming episodes and eventsExpanded strategies and resourcesDirect connection with Sheila for questions and supportSubscribe to the Newsletter: https://fivemilestones.kit.com/newsletter Connect on LinkedIn:https://www.linkedin.com/in/sheilaslick/ Subscribe on YouTube: https://www.youtube.com/@fivemilestonesFor more information, visit:Sheila Slick: https://sheilaslick.comFive Milestones: https://fivemilestones.com/show/Sponsored by: https://PodToBook.ai | Turn Your Podcast Conversations into a Book

Are you achieving everything on paper but feeling empty inside? What if the very traits driving your success are secretly fueling your burnout—and you can't even see it yet?Kassandra Hamilton, leadership and alignment coach and two-time best-selling author, collapsed on her floor after losing three family members, her dog, and her relationship in just months. What she discovered in that moment of surrender contradicts everything we're taught about achievement.How does a single word—"abracadabra"—hold the key to reshaping your entire reality? Why do most high achievers refuse to believe they're burned out until it's too late? And what made the "salesiest" approach feel wrong until one simple shift changed everything?Tune in to discover the milestone moment that transformed Cassandra's approach to success—and the one practice that makes life "magical again."To connect with Cassandra Hamilton, visit www.readysetrealign.caStay connected!Subscribe to Sheila's newsletter for:Early access to upcoming episodes and eventsExpanded strategies and resourcesDirect connection with Sheila for questions and supportSubscribe to the Newsletter: https://fivemilestones.kit.com/newsletter Connect with me on LinkedIn: https://www.linkedin.com/in/sheilaslick/ Subscribe on YouTube: https://www.youtube.com/@fivemilestonesFor more information, visit:Sheila Slick: https://sheilaslick.comFive Milestones: https://fivemilestones.com/show/Sponsored by: https://PodToBook.ai | Turn Your Podcast Conversations into a Book

What if the visibility strategy you're betting on is actually keeping you invisible?Julie Lokun, J.D., went from law school labor pains to building Chicago's premier visibility summit, but her journey revealed a controversial truth that most entrepreneurs refuse to accept. While everyone chases followers and engagement, there's a completely different game being played by those who actually dominate their industries.Here's what makes this conversation urgent: Julie works with everyone from Fortune 500 companies to White House insiders, and she's watched countless businesses waste years on the wrong platform. The answer? It's not about posting more. It's about something most people have completely abandoned.What happened when she shifted her entire strategy away from what "everyone knows works"? And why does she call social media "the lowest hanging fruit" that actually keeps you stuck?Plus, discover what makes Cre8tiveCon different from every other conference you've attended, and why networking might be the only thing you're actually taking home from most events.Tune in to discover the earned media secrets that traditional PR has been gatekeeping from entrepreneurs.Connect with Julie Loken:Visit: https://themediacastters.comCre8tiveCon: https://cre8tivecon.comStay connected!Subscribe to newsletter for:Early access to upcoming episodes and eventsExpanded strategies and resourcesDirect connection with Sheila for questions and supportSubscribe to the Newsletter: https://fivemilestones.kit.com/newsletter Connect on LinkedIn:https://www.linkedin.com/in/sheilaslick/ Subscribe on YouTube: https://www.youtube.com/@fivemilestonesFor more information, visit:Sheila Slick: https://sheilaslick.comFive Milestones: https://fivemilestones.com/show/Sponsored by: https://PodToBook.ai | Turn Your Podcast Conversations into a Book