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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.
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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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Networking Horror Stories: The Spooky Side of “Putting Yourself Out There
The Boss Society Podcast
33 minutes 26 seconds
2 weeks ago
Networking Horror Stories: The Spooky Side of “Putting Yourself Out There

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 downright scary side of building connections.

You’ll laugh, you’ll cringe, and you’ll definitely feel seen... because we’ve all been in those rooms that made us question why we showed up in the first place.


But by the end, these stories remind us why we keep showing up anyway… and what happens when you finally find yourpeople. 🤍


✨ Key Points

  • Megan’s personal story: from cliquey luncheons to cold coffee conference rooms
  • The truth about how intimidating networking can feel for introverts
  • Real community-submitted “networking horror stories” (and a few anonymous icks we can all relate to)
  • The importance of human-first connection and why authenticity always wins
  • A redemption story that reminds us: the scariest part of networking isn’t showing up, it’s thinking you don’t belong

🎄 Special Feature: Project Cheer

We’re partnering with members Katie Fama-Silver + Bryn from the Fama-Silver Agency and Heather Foster on Project Cheer... a community initiative to gift a fully decorated Christmas tree to a local family in need this holiday season.

🎁 Know someone who could use a little extra light and love?

Nominate them for Project Cheer before November 15th.

👉 HERE


🤍 Links Mentioned

  • Olympia Boss Society Membership: Become a Member
  • Project Cheer Nomination Form: Nominate HERE
  • Follow Megan on Instagram: @megangillespie
  • Follow Olympia Boss Society: @olympiabosssociety


🌙 Next Week on The Boss Society Podcast

We’re shifting from spooky to thankful as we head into November & Stef and I are recapping the entire Her Season retreat + are announcing something very exciting! 👀

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.