The Boss Society Podcast

In this week’s episode of  The Boss Society Podcast , Megan sits down with West Olympia real estate guide and community connector  Heather Foster  for an honest, funny, and deeply relatable conversation about what it means to reinvent yourself — again and again — until it finally feels right. From raising three kids as a military spouse to moving 20+ times and walking away from her...

When I recorded this episode a few weeks ago, I was in full “no launches, just nurturing” mode for the rest of summer. But as you’ll hear in the disclaimer, business moves fast, and sometimes the right opportunity changes everything. Mid-summer, the Her Season retreat went from “I’ll do it later” to “I need to do this now,” and this episode is the perfect example of why I decided to pivot. Today,...

In this episode, Megan sits down with her friend and fellow OBS member Stef McDonald to share something that’s been years in the making: the launch of  Her Season  ✨ a cozy, intentional retreat designed to help women reconnect with themselves and rise into their next season of life and business. They dive into how the vision finally came to life, why October is the perfect time to pause...

In this final episode of the  Summer Success Blueprint  series, Megan Gillespie gets real about what summer revealed, and why building a business with vision is the only way forward. From simplifying your offers to embracing the clarity that comes with slowing down, this conversation is a powerful reminder that you get to evolve. You’ll hear Megan reflect on the past few months, the less...

This one is for every woman who’s ever second-guessed whether she had anything worth selling. In this episode of the Summer Success Blueprint series, Megan is breaking down how to generate real income from the skills, ideas, and experience you already have, without launching a course, building a funnel, or burning yourself out. We’ll walk through the 3-lens framework Megan uses with her clients to...

In this episode of the  Boss Society  podcast, we’re getting honest about what it really means to lead through the mess... not just when everything’s going well. Megan shares her own experience navigating energy dips, personal struggles, and unexpected curveballs this summer, and offers a powerful framework for redefining  resilience as a CEO skill, not just a survival response. You...

In this freeing episode of the  Summer Success Blueprint  series, Megan unpacks why the traditional idea of “scaling” might be holding you back, and how to grow your business with more intention and less overwhelm. From simplifying offers to repurposing with strategy, this conversation is your permission to ditch hustle culture and choose sustainable growth that actually fits your life....

You walked into the room. Maybe for the first time. Maybe after a long hiatus. And maybe... it actually felt good. So now what? This week, we’re diving into  what happens after the yes  in part two of our networking redefined chat. Because it’s not just about showing up. It’s about how you hold your energy, carry the conversation, and follow up with intention. This episode is your practi...

In this episode of  The Boss Society Podcast , host Megan Gillespie gets real about what networking  should  feel like for women entrepreneurs—especially in the summer. If traditional networking gives you the ick, this conversation will feel like a breath of fresh air. Megan shares why connection over competition is the future, how to make networking feel more human, and the mindset...

In this episode of  The Boss Society Podcast , host Megan Gillespie unpacks what it really looks like to manage your time as a business owner during summer. Spoiler alert: it’s not about doing more or sticking to strict routines. Instead, she shares how to shift into rhythms that  actually work so you can grow your business  and  enjoy your life. You’ll learn how to ditch the g...

Welcome to The Boss Society Podcast and the kickoff of our brand new summer mini-series ✨ The Summer Success Blueprint✨ . In this episode, Megan shares a behind-the-scenes look at what shifted in her life and business this season, why summer requires a different kind of strategy, and what you can expect from this powerful 8-part series. If you’re a woman entrepreneur craving more visibility but...

In this heartfelt episode, Megan sits down with Valerie Gerrits, founder of Cedar Flats Flower Farm + Olympia Speech & Language, to talk about taking bold leaps in business and life. From private speech therapy practice to launching Olympia’s first u-pick flower farm—and now hiring an employee and moving into her own office space—Valerie’s story is all about trusting your timing and growing in...

In this solo episode, host Megan Gillespie breaks down what it really looks like to get your business ready for summer...without burning out, dropping the ball, or disappearing completely. From simplifying your visibility strategy to using theme days for focus and leaning into the magic of in-person networking, this episode is a crash course for you to make summer feel  lighter  while st...

In this episode, Megan sits down with Elizabeth Tennison—a personal chef with a passion for supporting busy women—to talk about what really happens when dinner becomes one thing too many. From debunking the myth that personal...

In this second half of our powerful two-part conversation, host Megan Gillespie and marketing hype girl Stef McDonald dive into the  real  talk around small business marketing—what actually works, what doesn’t, and how to avoid bu...

What happens when you build a business in the town you grew up in? In this episode, Megan sits down with Stef McDonald—Olympia native, marketing agency owner, and member of the Boss Society Inner Circle—to talk about how...

In this celebratory solo episode, Megan Gillespie reflects on two years of building Olympia Boss Society from scratch. What started as a single networking night has grown into a movement—one built not on polish, but on people. She shares the real story behind OBS, how vulnerability became the foundation for connection, and why leadership doesn’t have to mean being the loudest in the room. You’ll a...

In this week’s episode of  The Boss Society Podcast , Megan sits down with Kristy Cruz—military spouse, mom of three, and founder of The Succulent Studio. Kristy didn’t start her business until later in life—and now she’s teaching workshops, running a thriving succulent brand, and inspiring women to pursue their passions at any age. Together, they talk about the realities of building a busine...

⚠️ Trigger Warning This episode contains discussion of sexual abuse, eating disorders, and religious trauma, as well as candid talk about body image and intimacy. Please listen with care and skip any section that feels unsafe for you. How much of your business do you hold back because of how you feel in your body? Body‑ and sex‑positive artist, kink‑educator, and intimacy coach&nbsp...

In this episode of  The Boss Society Podcast , host Megan Gillespie shares a raw & honest perspective on what it really takes to build meaningful connections through networking—especially at the local level. From dreading networking events to now hosting them through Olympia Boss Society, Megan walks listeners through the mindset shifts, strategies, and personal growth that come from show...

In this episode of  The Boss Society Podcast , host Megan Gillespie sits down with personal brand photographer Deedre to talk about the power of showing up—visually and energetically—as the face of your business. Together, they explore how brand photography builds more than just your image—it builds trust, confidence, and connection. From overcoming imposter syndrome to finding your energy in...

In this episode of The Boss Society Podcast , Megan Gillespie sits down with Danielle Moran to explore the courage it takes to chase your dreams — even when fear tries to hold you back. Danielle shares her experience of navigating entrepreneurship, the lessons learned along the way, and the importance of leaning on your community for support. From recognizing your worth to embracing the messiness...

In this episode of The Boss Society Podcast , Megan Gillespie sits down with her former co-founder and business bestie, Sophie Burley, to talk about how one unexpected connection can change everything. From meeting in a random Facebook group to building a thriving community together, their journey is a testament to the power of putting yourself out there. They dive into how authentic relationships...

In this inaugural episode of  The Boss Society Podcast , host Megan Gillespie shares her journey of building community and the evolution of her podcasting career. She highlights why authentic relationships are the foundation of business success and how community-driven strategies are shaping the future for women entrepreneurs. Get ready for real, unfiltered conversations, actionable advice, a...

Welcome to The Boss Society Podcast – your seat at the table. Your voice in the conversation. THE place where women are rewriting the rules of business, one authentic relationship at a time. If you're tired of being surrounded by cringey small talk and surface-level networking, you’re in the right place. Here, it’s all about real, raw conversations that empower, inspire, and connect you with the r...