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The Boss Society Podcast
Megan Gillespie
34 episodes
6 days ago
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.
Show more...
Entrepreneurship
Business,
Marketing
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All content for The Boss Society Podcast is the property of Megan Gillespie and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
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.
Show more...
Entrepreneurship
Business,
Marketing
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Her Season: A Retreat for Women Entrepreneurs
The Boss Society Podcast
29 minutes 24 seconds
3 months ago
Her Season: A Retreat for Women Entrepreneurs

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 before the end-of-year rush, and what makes this retreat feel so different from any other business event. From hot seat masterminds to forest walks, silent mornings to pajama game nights, Her Season blends strategy and restoration in a way that feels grounded, nourishing, and honest.


This isn’t about cramming in more info or pushing harder. It’s about stepping away long enough to hear yourself again.

If you’ve been craving space, support, and a room full of women who get it ... this one’s for you.


✨ Key Takeaways

  • Her Season is designed to support both personal restoration and business clarity...without the pressure.
  • October is a powerful transition month, a chance to reset before holiday overwhelm.
  • This retreat is for the woman who leads everything… but rarely pauses for herself.
  • It’s not a conference. It’s an intimate, in-house experience with 10–14 women.
  • The retreat includes hot seat masterminds, solo reflection, workshops, journaling, and connection.
  • Visibility support is available without pressure to perform or show up a certain way.
  • Participants leave with a personalized Q4 plan, a message to their future self, and restored energy.
  • The retreat offers a rare opportunity to be held, witnessed, and supported by women who understand.
  • This experience is about coming home to yourself... and rising from that place.

💥 Fast Action Bonus — Ends in 24 Hours!

Apply within the first 24 hours and receive:

✔️ A 30-minute 1:1 Strategy Session with Megan

✔️ Early access to bed selection if you pay in full

This bonus ensures you’ll arrive already supported, grounded, and ready to make the most of your retreat experience.


Her Season: An OBS Retreat

October 10–12, 2025 | Union, WA

A weekend of deep connection, personal restoration, and aligned business strategy

→ Click here to apply now


Have questions? Looking for creative payment options? Not sure if this is the right time? Let's talk about it! Send us a message hello@olympiabosssoceity.com

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!

The Boss Society Podcast
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.