The Boss Society Podcast
Podcast Description
The Boss Society Podcast is where high-achieving women come together to share real business stories, raw conversations, and powerful insights. This isn't just another business podcast—it’s a seat at the table with local women leaders who are making an impact.Each episode gives you a peek inside the rooms where real business happens, featuring unfiltered advice, behind-the-scenes moments, and conversations that go beyond surface-level success. Whether you’re a seasoned entrepreneur or just getting started, this show will challenge, inspire, and connect you with a community of ambitious women rewriting the rules of business.Pull up a chair—your voice belongs in this conversation.
Podcast Insights
Content Themes
The podcast focuses on themes of community building, authentic relationships, and women entrepreneurship, with episodes discussing topics like the unexpected power of connections and the importance of vulnerability in business.
The Boss Society Podcast is where high-achieving women come together to share real business stories, raw conversations, and powerful insights. This isn’t just another business podcast—it’s a seat at the table with local women leaders who are making an impact.
Each episode gives you a peek inside the rooms where real business happens, featuring unfiltered advice, behind-the-scenes moments, and conversations that go beyond surface-level success. Whether you’re a seasoned entrepreneur or just getting started, this show will challenge, inspire, and connect you with a community of ambitious women rewriting the rules of business.
Pull up a chair—your voice belongs in this conversation.
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 require burnout. Megan shares how these shifts are shaping Olympia Boss Society in 2026, what’s coming inside the community this year, and why this season of business calls for building better, not bigger.
This episode also kicks off a new January podcast series featuring community leaders from Olympia to Seattle,diving into the ins and outs of community, networking, and sustainable business growth.
Key Points
- Why many women entrepreneurs are not entering 2026 with a sprint, and why that’s actually a win
- Megan’s most meaningful wins and lessons from 2025, including leadership, capacity, and letting go of performance
- What Megan witnessed in women business owners this past year: the shift toward stability, belonging, and slower rooms
- What Megan is carrying forward into 2026, and what she’s intentionally leaving behind
- The evolving role of community, networking, and visibility for women entrepreneurs
- What’s coming inside Olympia Boss Society in 2026:
- Monthly Connection Nights
- Monthly Coffee & Convos (member-only, with quarterly open events)
- Quarterly Content Creation Days with hands-on support from industry experts
- Spring and fall retreats
- OBS’s 3-year anniversary
- New partnerships and collaborations
- The real “ins and outs” for sustainable business growth in 2026
- An introduction to the upcoming podcast series with community leaders
Special Offer
She Blooms Retreat | March 19–22
If January pressure has you feeling like you’re supposed to reinvent yourself overnight, She Blooms offers a different approach. This spring retreat is designed to help women entrepreneurs gain clarity without burnout and build momentum that actually fits their life.
At She Blooms, attendees will walk away with:
- A fully outlined nurture sequence to automate a freebie funnel and attract aligned leads year-round
- A multi-channel marketing plan blending email, partnerships, community, and sustainable social media
- A customized 90-day Bloom Plan that honors energy, capacity, and season
- A circle of women who see the real you and say “hell yes”
Payment plans are available. Apply HERE 🌿✨
Links Mentioned in the Episode
- Apply for She Blooms Retreat HERE
- Learn more about Olympia Boss Society HERE
- Join the OBS Collective Membership HERE
Preview for Next Week
Next week, the January series begins. Megan sits down with community leaders to talk about what’s shifting in community-building, networking, and small business… and what women entrepreneurs actually need to feel supported and seen in 2026.
Loved this episode? Make sure to subscribe so you never miss a conversation inside The Boss Society Podcast! If you found value in today’s episode, share it with a friend or leave a review—it helps more women like you find the show.
✨ Stay connected:
📲 Follow me on Instagram: @themegangillespie @olympiabosssociety
📩 Join the community: www.olympiabosssociety.com
🎙️ Want to be a guest? Apply HERE
Your voice matters. Your seat at the table is waiting. See you next time!
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