Milestone Moments in Business & Leadership

Hosted by Sheila Slick

Business EducationInterviews guests

Website RSS feed LinkedIn

Episodes

125

Latest episode

Aug 2026

Language

About the show

Every entrepreneur, every leader, every woman building something meaningful has a milestone moment. A turning point that changed everything. Milestone Moments in Business and Leadership is a storytelling podcast hosted by Sheila Slick, founder of Five Milestones LLC. Each episode is a guided conversation that goes deeper than business strategy. We explore the life you built, the moment everything changed, and the person you are today. Our guests are entrepreneurs, coaches, leaders, and aspiring authors who are ready to share the real story behind their success. Not the highlight reel. The truth. Select guests are invited to become published authors through our Contributing Author program, where their interview is transformed into a professionally edited, published story using our proprietary PodToBook.ai software. You have a story that matters. It is time to tell it. www.fivemilestones.com

Listen to episodes

60 recent

August 5, 202625 min

What Really Happens After You Become a Published Author?

What if one conversation could change everything? These six women sat down for a podcast interview. That conversation became a published chapter. That chapter became part of an international #1 bestseller in four countries. And in Part 2 of this special roundtable, they answer the question every aspiring author wants to know: what really happens after you become a published author? Then Kassandra Hamilton asked each woman what she would say to the version of herself before she shared her story. What came out is something every woman sitting on her own story needs to hear. Listen in to learn more about becoming a published author through one conversation, building momentum after your first book, and why sharing your story creates opportunities you can't predict. Your story matters. Ready to tell it? Visit fivemilestones.com to be a guest on the show. One conversation is all it takes to become a published author. Get the book: The Rise of the Self-Led Woman on Amazon: https://amzn.to/4hNRtPb Kassandra is now accepting applications for Volume 2. If this episode stirs something in you, this may be your moment. Apply for Volume 2: https://readysetrealign.ca/books/the-rise-of-the-self-led-woman-volume-2 Stay connected! 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: Five Milestones: https://fivemilestones.com/show/ Sponsored by: https://PodToBook.ai | Turn Your Podcast Conversations into a Book

August 4, 202627 min

How One Conversation Made 11 Women Bestselling Authors

What if the only thing standing between you and a published book was a single conversation? In this special episode of Milestone Moments in Business and Leadership, host Sheila Slick sits down with seven co-authors of The Rise of the Self-Led Woman : Stories of Resilience, Realignment, & Rising , the international #1 bestseller curated by Kassandra Hamilton that hit the top of the charts in four countries. Each woman walked into a conversation and walked out a published author. But what happened after the book landed in their hands? The reactions surprised even them. This is Part 1 of a powerful two-part conversation. Listen in to learn more about becoming a published author through collaboration, overcoming the fear of being seen, and building community through shared storytelling. Get the book: The Rise of the Self-Led Woman : Stories of Resilience, Realignment, & Rising on Amazon: https://amzn.to/4hNRtPb Kassandra is now accepting applications for Volume 2. If this episode stirs something in you, this may be your moment. Apply for Volume 2: https://readysetrealign.ca/books/the-rise-of-the-self-led-woman-volume-2 Stay connected! Connect with me on LinkedIn: https://www.linkedin.com/in/sheilaslick/ Subscribe on YouTube: https://www.youtube.com/@fivemilestones For more information, visit: https://fivemilestones.com/show/ Sponsored by: https://PodToBook.ai | Turn Your Podcast Conversations into a Book

July 31, 202615 min

Inside the Empowered Podcasting Conference with Rich Perry

We're giving away FREE tickets to the Empowered Podcasting Conference, a community built to help results-driven podcasters, video makers, and content creators elevate their passion and creativity to new heights! Comment #ShareYourStory on social media for your chance to win. Rich Perry, CMO and partner of the Empowered Podcasting Conference , takes us inside this annual conference in Charlotte, NC dedicated to helping podcast creators build impactful shows and sustainable businesses. From expert-led sessions on monetization and sponsorships to hands-on tools for growing your audience, Rich reveals what attendees walk away with and why the community keeps delivering value long after the event ends. But here's the best part: PodToBook.ai is a proud sponsor of Empowered Podcasting, and we're giving away FREE tickets! Comment #ShareYourStory on social media for your chance to win. Whether you're launching your first episode or looking to take your podcast to the next level, find out why this is the room you need to be in August 21-23. Stay connected! 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: https://fivemilestones.com/show/ PodToBook.ai | Turn Your Podcast Conversations into a Book

February 11, 202613 min

Leveraging Leadership and the Path to Consulting Success with Liz Weber

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 @LizWeberCMC Stay connected! Subscribe to Sheila's newsletter for: Early access to upcoming episodes and events Expanded strategies and resources 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

July 29, 202623 min

Turn Your Creative Gift into a Career with Allen C. Paul

What would you do if you walked away from not one, but two stable careers to chase a creative dream with no safety net? Alan Paul spent 30 years navigating the tension between faith, creativity, and making a living. A classically trained musician turned teacher turned church leader, Alan kept feeling a pull toward something more. But it was the moment he handed in his resignation, just as a promotion was being offered, that everything changed. Now with over 500 podcast episodes, multiple books, devotionals on the billion-download YouVersion app, and performances alongside jazz and soul legends, Alan has built an entire platform dedicated to helping creatives thrive. But how did a "pamphlet" idea sketched out in a bedroom become the foundation for all of it? Listen in to learn more about turning creativity into a sustainable business, overcoming creative blocks as an entrepreneur, and building a platform through community connections. To connect with Alan Paul, visit godandgigs.com or alancpaul.com Stay connected! Subscribe to Sheila's newsletter for: Early access to upcoming episodes and events Expanded strategies and resources 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

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.ca Stay connected! Subscribe to Sheila's newsletter for: Early access to upcoming episodes and events Expanded strategies and resources 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

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.com Cre8tiveCon: https://cre8tivecon.com Stay connected! Subscribe to newsletter for: Early access to upcoming episodes and events Expanded strategies and resources 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/@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

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.com Alex is co-author of Unscripted Brilliance: The PodMatch Edition a 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 events Expanded strategies and resources 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 Join 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.com Speaking: chrismajer.com Book: The Power to Transform (available on Amazon) Stay connected! Subscribe to Sheila's newsletter for: Early access to upcoming episodes and events Expanded strategies and resources 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/@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

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 events Expanded strategies and resources 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