The Boss Society Podcast

What if your business was built to bloom again and again, instead of constantly feeling like you’re starting over? In this solo episode, Megan shares a powerful visibility audit to help you look at your business foundations, your marketing, and the way people experience your work. Inspired by the conversations happening during the She Blooms retreat, this episode is a reminder that sustainable gro...

Starting a business doesn’t always begin with a perfect plan. Sometimes it begins with a conversation, a spark of encouragement, and the courage to believe you might actually be capable of more than you thought. In this episode, Megan sits down with Bryn Silver, owner of  The Ease Project , to talk about what it really looked like for her to start a business from the ground up. Just a few mon...

In honor of International Women’s Day, this bonus episode is a little different. At a recent Olympia Boss Society event, we walked around the room and asked a simple question: “What do you love about being a woman in business?” The answers were thoughtful, empowering, and deeply relatable. In this short mash-up episode, you’ll hear a collection of voices from women in the Olympia Boss Society comm...

Season 2 of  The Boss Society Podcast  is here (🎉) and we’re kicking it off with an honest behind-the-scenes look at what’s happening inside Olympia Boss Society. In this episode, Megan shares February wins inside the community, lessons that surfaced along the way, and a powerful reframe about growth that many entrepreneurs experience but rarely talk about. She also reflects on a questi...

Over the last several weeks, we’ve talked about pace, community, marketing, motherhood, capacity, trust, and credibility. But this final episode isn’t a recap. It’s a zoom-out. In this closing chapter of the 2026 Ins & Outs series, Megan pulls together the most powerful moments from each conversation and reflects on what’s actually shifting for women entrepreneurs this year. This isn’t about t...

In this episode of our 2026 Ins & Outs series, we’re talking about something many business owners are feeling but not always saying out loud: copy culture. Megan opens the conversation by sharing a personal experience that’s been unfolding since late last year... a situation where inspiration crossed the line into replication. Not buzzwords. Not industry overlap. But tone, structure, visuals,...

If you’ve been feeling like you have to be louder, post more, and constantly perform just to stay relevant… this episode is for you. We are in what I call a  trust recession. People are overwhelmed. They are skeptical. They are slower to buy and quicker to disengage. And the old “just show up consistently and post your best content” advice is not enough anymore. In this solo episode of the 20...

What happens when motherhood collides with neurodivergence, entrepreneurship, and a culture that still expects women to “do it all”? In this powerful conversation, Megan sits down with Bailey Gordon, photographer, founder of the Mom Boss Meetup, and community builder, to talk honestly about what 2026  actually  needs to look like for mom entrepreneurs. From late ADHD diagnoses and PMDD,...

We’re continuing the  2026 Ins & Outs series , and this two-part conversation is focused specifically on  mom entrepreneurs . In  Part 1 , I’m joined by Bailey Gordon, founder of The Mom Boss Meetup, to talk about what’s shifting beneath the surface for moms who are building businesses while raising kids... especially when neurodivergence, burnout, and changing capacity are part...

Marketing feels louder, heavier, and more exhausting than ever. In this episode of The Boss Society Podcast, Megan sits down with returning guest  Amy Carlson , founder and creative director of Sand & Pine Creative, to unpack what’s  actually  working in marketing as we head into 2026 and what needs to be left behind. This conversation goes beyond trends and tactics and gets hon...

We’re kicking off the  2026 Ins & Outs series  with a grounded, honest conversation about what’s shifting in community, networking, and small business as we head into a new year. In this episode, Megan is joined by  Rachel Rowland , a local community leader who has a front-row seat to how women are showing up, what they’re craving, and what no longer fits. Together, they unpack...

In the first episode of 2026, Megan Gillespie slows the conversation down. Instead of pushing predictions, hustle, or “new year, new me” pressure, she reflects on her real wins and lessons from 2025 and what she’s witnessing in women entrepreneurs right now. This episode explores why so many women are craving stability over speed, belonging over performative networking, and visibility that doesn’t...

We’re closing out the year with a powerful small business story for women entrepreneurs who are building their business one brave step at a time. In this final episode of 2025, Megan sits down with  Sarah, owner of Moonstruck by Sarah and Moonstruck Studio , to talk about what it really looks like to grow from  selling at vendor markets and Etsy  into opening a  brick-and-morta...

This week on The Boss Society Podcast, I’m joined by three of our Inner Circle members: Heather Foster, Bryn, and Katie Fama-Silver, to share the heartwarming story behind  Project Cheer . What started as a simple idea to gift a fully decorated Christmas tree to a local family turned into something even bigger… two families receiving a little holiday magic when they needed it most. In this co...

In this episode, Megan returns after a tech-glitch break to share her most powerful December rituals for women entrepreneurs: seasonal reflection, capacity-based planning, and scripting your 2026 with intention. We talk about the difference between  desire and capacity , how to review your year without self-criticism, and why traditional goal setting often leads to burnout. Megan breaks down...

It’s only November… and somehow, the new year pressure is already creeping in. In this solo episode, Megan gets honest about what it really looks like to stay visible during the holiday season  without burning out. From why she skips Black Friday deals to how to show up in a way that feels grounded, she shares a fresh perspective on doing business differently this time of year. This isn’t abo...

You know that feeling when everything finally  clicks... when you realize you’re exactly where you’re meant to be? That’s what  Her Season  felt like. In this episode, Megan and Stef pull back the curtain on Olympia Boss Society’s first-ever retreat: a weekend filled with transformation, laughter, late-night breakthroughs, and the kind of connection that changes you from the inside...

Episode Description: It’s Halloween week and what better way to celebrate than with a few truly terrifying tales from the world of networking? 👻 In this special spooky-season episode, Megan shares her own “introvert’s nightmare” story from the buttoned-up, performative networking days that inspired Olympia Boss Society, along with real stories from local women about the awkward, cringey, and down...

This October, we’re diving into  spooky situations  in business... the ones that make us squirm a little but hold so much power when we finally face them. And this week’s fear? Being  seen. Megan sits down with  Amy Carlson , founder of  Sand & Pine Creative , to talk about what it really takes to show up in your business with authenticity, vulnerability, and self-trus...

This week, Megan sits down with financial advisor  Anna Fanning  to talk about what it really feels like to be underestimated at work. The conversation started at Coffee & Convos when a question about handling constant objections from men lit up the room. Anna shares how being underestimated began for her as a kid, how it shows up in male-dominated spaces, and the quiet confidence mo...

It’s spooky season 👻 and here on The Boss Society Podcast, October is all about  spooky situations  ... from networking horror stories to next week’s conversation about being underestimated by men. But before we dive into all of that, we’re starting the month with one of the scariest things in business: not having a plan. In this solo episode, Megan walks you through her simple method f...

What does it mean to keep showing up for your business when the world feels unbearably heavy? In this candid roundtable conversation, Megan sits down with Olympia business owners  Nicole Pate  and  Melanie Asher to unpack the tension between running a business and holding space for humanity in difficult times. Together, they explore how to market with integrity, lead with responsibi...

This week on  The Boss Society Podcast , Megan sits down with Inner Circle member and boutique insurance agent  Katie Fama-Silver  for a raw, heartfelt conversation about stepping out from behind the scenes and into your own spotlight. Katie opens up about what it was like to stand behind more extroverted women in the past, why she finally decided to build her own brand, and how joi...

If you’ve ever tried  all  the business strategies and still felt like something was off, this episode is for you. Megan sits down with Aypril Porter—life and business coach, grief guide, Human Design expert, and projector—to talk about how understanding your energetic blueprint can change everything. From unlearning burnout to working through invisible fears, this is a conversation abou...

Megan’s birthday is on Saturday (🥳), and she’s marking the moment by sharing 38 of the most powerful lessons she’s learned in 38 years. This milestone episode of The Boss Society Podcast blends personal growth, motherhood, and entrepreneurship, reflecting on how these experiences have shaped her life and business. From redefining success and building community, to setting boundaries, honoring sea...