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The Boss Society Podcast
Megan Gillespie
34 episodes
5 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
https://is1-ssl.mzstatic.com/image/thumb/Podcasts221/v4/2b/56/61/2b5661c2-b1cb-1d5c-c933-9dbf9db38c24/mza_7517178789324632378.jpg/600x600bb.jpg
Tales of Men Not Taking You Seriously at Work... and What To Do About It
The Boss Society Podcast
43 minutes 51 seconds
4 weeks ago
Tales of Men Not Taking You Seriously at Work... and What To Do About It

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 moves that shift the power back. You’ll hear practical language to use in the moment, how to balance authority with authenticity, and why money knowledge is confidence.


Key Points

  • The Coffee & Convos moment that sparked this episode and why it hit home for Anna
  • Anna’s early story of being underestimated and how she turned it into fuel
  • What underestimation looks like in male-dominated industries and peer dynamics
  • Phrases and proof points that diffuse condescension without getting defensive
  • The “Do you trust me?” question that resets the room
  • Personal brand vs. professional authority and finding the sweet spot
  • Money as power for women, and why knowing your numbers builds confidence
  • Choosing clients who trust you, setting boundaries, and saying no
  • How community helps you quiet self-doubt and stop underestimating yourself


Special Offer

Ready for more of these conversations in real life? Join Olympia Boss Society to get access to member events like Coffee & Convos and Connection Night, our community chat, and ongoing support to grow your business with confidence. Perfect timing with our fall lineup.


Links Mentioned

  • Connect with Anna Fanning: Website
  • Join Olympia Boss Society membership: Join the Collective
  • Come to our next public event: Events Calendar


Preview for Next Week

We’re keeping the spooky season energy going with a hair raising convo all about the fear of being seen!

Enjoying the show?

If this episode made you feel seen, tap the stars and leave a quick review. Share it with a friend who needs the reminder that her voice belongs in every room.

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.