Milestone Moments in Business & Leadership

Hosted by Sheila Slick

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112

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Jun 2026

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About the show

Milestone Moments is a motivational podcast designed to inspire action and celebrate the pivotal achievements on the path to success. Hosted by Slick, founder of Five Milestones, this show explores the journeys of experts, entrepreneurs and leaders who have turned their visions into reality. Our carefully curated guests share not just their expertise but their milestone moments—those turning points that redefined their paths and led to their achievements. Through engaging conversations, we explore the strategies that led to their breakthroughs, the challenges they overcame, and the lessons learned along the way. Tune in to "Milestone Moments" to ignite your drive, embrace your journey, and celebrate the milestones that mark the path to your success. www.fivemilestones.com

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60 recent

January 30, 202615 min

Why Do Successful People Feel Empty Inside? with Kassandra Hamilton

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

January 28, 202624 min

The Earned Media Strategy Top Entrepreneurs Need with Julie Lokun, J.D.

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

January 23, 202619 min

The PodMatch Strategy: How to Validate Your Business Idea with Alex Sanfilippo

What if one question asked to hundreds of podcasters could reveal a million-dollar opportunity?Alex Sanfilippo did exactly that at PodFest 2020. After 15 years in corporate aerospace, he walked away with a calculated plan. Today, PodMatch has paid over $1 million in commissions to podcasters on the platform.But here's what most people don't know: the single question that started it all, and the four-step framework he used to turn community frustration into a thriving platform.Listen now to discover what he asked and why it changed everything.To connect with Alex Sanfilippo visit PodMatch.comAlex is co-author of Unscripted Brilliance: The PodMatch Editiona book that's brave in its honesty, bold in its approach, and brilliant in its execution. Whether you're a podcast host seeking inspiration, an entrepreneur wanting substance over style, or a leader ready to own your authentic voice, this book offers valuable insights wrapped in compelling stories.Stay 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 BookJoin PodMatch: https://www.joinpodmatch.com/fivemilestones

January 21, 202622 min

Why Your Body Learns But Your Mind Just Understands with Chris Majer

What if the reason your leadership training never sticks has nothing to do with the quality of the program? Chris Majer—who's trained everyone from U.S. Special Forces to Microsoft executives—reveals the uncomfortable truth: understanding happens instantly, but your body only learns through practice. And practice takes time.Why do most adults never actually learn anything new? We're more committed to being comfortable than to changing. Majer shares the exact moment executives realize they've been "practicing being bad" at their own skills, what happened when he put a Fortune 500 leader on a 40-foot pole, and why his flagship program takes nine months instead of two days.Here's what nobody tells you about AI implementation, risk-taking, and breakthrough performance: you can't teach what you haven't experienced yourself. Ready to stop confusing understanding with competence? Tune in to this episode to discover why "impossible" is just a limitation you've invented, and what shifts when you push one step beyond your edge.To connect with Chris Majer:Website: humanpotentialproject.comSpeaking: chrismajer.comBook: The Power to Transform (available on Amazon)Stay 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 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

January 14, 202614 min

True Crime Meets Compliance with Davreen Dixon, JD

What makes someone abandon a potential real estate podcast to spend years dissecting financial crimes? Davreen Dixon, JD discovered her calling through a law school assignment that changed everything—and turned it into a podcast that's redefining compliance training.Here's what most compliance professionals face: dry regulations, endless technical documents, and training that puts people to sleep. But what if financial crime cases were told like the true crime stories millions of people binge-listen to every week?The Compliance Times takes real money laundering cases, fraud schemes, and sanctions violations and asks three questions that transform how professionals learn: What happened? How was it uncovered? And what can you do to protect your organization?From seasonal story arcs to bridging the gap between compliance experts and true crime enthusiasts, could narrative-driven storytelling be the missing piece in financial crime prevention?Tune in to discover how one JD is revolutionizing compliance education through storytelling.To connect with Davreen Dixon, visit The Compliance Times podcast.Stay 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/newsletterConnect 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

January 7, 202622 min

How a Theater Professor Turned Business Into a Quest with Paul Eric Pape

What happens when your side gig makes more than your stable $45K job? Paul Eric Pape—"Santa for Nerds" who's designed for Disney, Universal, and Nickelodeon—faced that exact choice. His wife gave him one year. Within four months, something happened that changed everything.Here's what most creatives get wrong about pricing: they're competing with the wrong companies. Paul reveals why the moment he stopped doing one specific thing, his worst customers disappeared and the right clients started showing up willing to pay premium prices.But there's a bigger problem killing creative businesses before they start. It has nothing to do with talent or market demand. Paul shares the counterintuitive business model that consultants told him would fail—yet it's been his secret weapon for two decades.Ready to stop grinding and start leveling up? Tune in to discover why Paul calls himself a wizard instead of an artist, what "bend, don't break" really means when clients ask for the impossible, and the role-playing game principle that makes boring business tasks actually completable.To connect with Paul Eric Pape:Website: GamifyBusiness.comFree book sample: GamifyBusiness.com/podcast (first two chapters of The Creative Player's Handbook to Business)Social media: @PaulPapeDesignsTEDx Talk: "Santa for Nerds"Stay 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 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

December 31, 202517 min

Leap Into Your Next Reinvention in the New Year with Sabine Hutchison

What if the path you've been told to follow is exactly what's holding you back? CEO and scientist-turned-entrepreneur Sabine Hutchison reveals why career pivots don't mean starting over – and the surprising skill that determines whether your reinvention succeeds or fails spectacularly.From touring with David Copperfield to launching companies across multiple industries, Sabine has cracked the code on pivoting without losing momentum. But here's the catch: most professionals make one critical mistake when changing directions that costs them thousands in lost salary and years of advancement.What's in your "Spotify list of skills"? And why does society's definition of success keep brilliant leaders stuck in careers that drain them? Discover why turning 60 launched Sabine's most ambitious chapter yet – and what she knows about regret that changes everything.Tune in to discover the unconventional framework that turns career chaos into strategic advantage.To connect with Sabine Hutchison, visit SabineHutchison.comStay 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

December 24, 202519 min

Building Confidence to Speak Up with Tonya Lehman

What if being quiet doesn't mean you have nothing to say—it means no one's giving you the space to say it?Tonya Lehman stood in her husband's manager's bathroom, reading every ingredient on the hand lotion bottle, killing time to avoid returning to a party where she'd been completely ignored. That moment became her turning point: just because she's an introvert doesn't mean she deserves to be invisible.Now Tonya helps quiet professionals gain the skills and confidence to speak up for personal growth and professional impact. But here's what most leaders miss: introverts aren't just shy—they're untapped potential sitting in meetings, composing emails in their minds instead of contributing in the moment.The psychological safety problem: Leaders ask "any questions?" and move on within seconds. Extroverts see opportunity where introverts see risk. And the loudest voice always wins—until it doesn't.Tonya reveals why physically raising your hand changes everything, how to address points made earlier in conversations without awkwardness, and the critical mistake she made using one word that dismissed her entire team's concerns (and the email from her boss that followed).Are you leaving your best ideas unspoken?Through her Speaking Games Club and the "I Have a Gift for You" exercise, discover how spontaneously dealing with uncertainty builds the muscle introverts need to contribute powerfully. Connect with Tanya Lehman: Website: https://joylab.biz Social Media: @SpeakUpWithTanya LinkedIn: Tanya LehmanStay connected!Subscribe to Sheila's newsletter for early access to episodes and expanded strategies.Newsletter: https://fivemilestones.kit.com/newsletter LinkedIn: https://www.linkedin.com/in/sheilaslick/ YouTube: https://www.youtube.com/@fivemilestonesFor more information: Sheila Slick: https://sheilaslick.com Five Milestones: https://fivemilestones.com/show/Sponsored by: https://PodToBook.ai

December 17, 202517 min

What CEOs Get Wrong About Being Indispensable with Andrew Brummer

Meet Andrew Brummer, "the business polygraph"—who discovered at 53 that the worst career crisis could become his greatest breakthrough. But the pivotal moment didn't come from what happened to him. It came from what he understood about fear itself.Here's the question keeping successful leaders stuck: What if the one thing you're protecting yourself from is actually robbing you of eight other wins? Andrew reveals why most CEOs are building their empires on a dangerous lie—and it's not what you think.Ready to discover what you're leaving on the table?Tune in now to hear the full breakthrough Andrew shares with leaders from Iraq to India.To connect with Andrew Brummer, visit andrewbrummer.com or find him on LinkedIn.Stay 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

December 10, 202515 min

Become an Essentialist CEO to Build Profitable Systems with Kasey Jones

Kasey Jones works with coaches and consultants who've discovered an uncomfortable truth: they haven't built a real business. They've created what Kasey calls a "full-time side hustle"—a collection of random referral-based projects that never compound or scale.The referral trap feels safe because work comes to you. But what happens when those referrals slow down? Without systems or a repeatable process, you're left wondering what to tell people you actually do.Here's Kasey's perspective shift: if you genuinely believe your work helps people, you have a responsibility to make sure those who need you can find you. Sales and outreach aren't selfish—they're acts of service.But what's really keeping you stuck? Kasey reveals the two hidden reasons smart professionals don't take action (hint: it's not just fear), plus her framework for breaking through when the path forward feels overwhelming.Listen to this episode to discover what it takes to become the "chief experience officer" of your life—not just your business.Connect with Casey Jones: Website: https://essentialistceo.com Social Media: @abetterjones (all platforms)Stay connected!Subscribe to Sheila's newsletter for early access to episodes and expanded strategies.Newsletter: https://fivemilestones.kit.com/newsletter LinkedIn: https://www.linkedin.com/in/sheilaslick/ YouTube: https://www.youtube.com/@fivemilestonesFor more information: Sheila Slick: https://sheilaslick.com Five Milestones: https://fivemilestones.com/show/Sponsored by: https://PodToBook.ai