The Boss Society Podcast

About 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.

Publisher

Megan Gillespie

Category

business

Language

en

Explicit

No

First episode

7 Mar 2025

Latest episode

29 Oct 2026

Latest episodes

79 episodes in the feed.

1. 

   29 Oct 2026

   Six Months Can Change Everything: October Reflections on Visibility, Vulnerability & Trusting the Timing

   In this solo episode of The Boss Society Podcast, Megan is wrapping up October with a look at the wins, unexpected lessons, and full-circle moments that made this month so meaningful. From Halloween Speed Connecting and reflective Coffee & Convos conversations to wrapping up six weeks of masterminding inside The Room, October was a reminder of just how powerful the right community can be. Megan also opens up about launching The Room during a difficult personal season in April, what changed over the following six months, and why she's so grateful she didn't give up on the vision. And of course, we're talking about HOT MIC: A Boss Society Live Podcast Experience! Megan shares the inspiration behind bringing her podcast to the stage, the vulnerability of publicly documenting her Road to 100 ticket-selling journey, and why she's challenging women business owners to think beyond social media when it comes to marketing in 2027. Plus, an October card pull that feels a little too accurate, and a sneak peek at everything happening inside Olympia Boss Society this November. In This Episode: The highlights from October's Halloween Connection Night, Coffee & Convos, and The Room mastermind Why the right timing can completely change how an idea comes to life The vulnerability of launching offers, hosting events, and asking people to believe in what you're creating How Megan's life and business have evolved since last year's first OBS retreat Stepping into a new teaching role with the Thurston County EDC's ScaleUp program Why HOT MIC is bringing business conversations beyond the podcast and into a room full of women Behind the scenes of Road to 100 and experimenting with creative marketing strategies October's card pull: One Step Ahead Is All You Need, Cut the Cords of Doubt, and The Spark of Hustle What's coming up in November at Olympia Boss Society 🎙️ HOT MIC: A Boss Society Live Podcast Experience Beyond the Algorithm: Marketing Beyond Social Media Everyone is telling you what to post in 2027. We're talking about everything else. Join us for an afternoon of live podcast conversations, expert insights, real connections, and a whole lot of fun as we explore marketing strategies that go beyond the algorithm. We're bringing together incredible women to talk about podcasting, SEO, community building, lead generation, and the opportunities business owners may be overlooking. Expect live interviews, panel conversations, audience participation, a red carpet experience, curated women-owned shopping, and plenty of opportunities to connect. Friday, January 15, 2027 Centralia Square Grand Ballroom | Centralia, WA Doors open at 1 PM | Live show 2–5 PM VIP After Hours immediately following General Admission: $97 | VIP: $147 🎟️ Get your HOT MIC tickets: https://olympiabosssociety.com/hotmic (https://olympiabosssociety.com/hotmic) ✨ Coming Up at Olympia Boss Society November 5 | Friendsgiving Connection Night Our annual members-only Friendsgiving celebration! We're gathering for a potluck, meaningful conversations, and a special masterminding experience to celebrate the women who make this community what it is. Exclusive to Society Collective members. November 13 | Content Lab: Batching & Planning Get intentional about your content strategy and make real progress planning and batching content for the rest of the year. Plus, professional headshots with Deidre! Open to the public and included with Society Collective membership. November 16 | Coffee & Convos Open House Curious about Olympia Boss Society? Our quarterly Open House is your opportunity to experience the conversations, connections, and community firsthand. Open to the public. Join The Society Collective Connection Nights, Coffee & Convos, quarterly Content Labs, planning sessions, community support, and so much more, all included in one monthly membership. Explore Olympia Boss Society: https://olympiabosssociety.com (https://olympiabosssociety.com/) Let's Connect! Follow along with Megan's Filling the Room series on Instagram and TikTok for a behind-the-scenes look at what it takes to fill a room with 100 women, including creative marketing experiments, event planning, and everything happening along the way. Keep showing up, keep making connections, and remember: sometimes one step ahead is all you need. 💋 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 (https:// www.olympiabosssociety.com) 🎙️ Want to be a guest? Apply HERE (https://forms.gle/T4yTgaH5dG2S4dvg7) Your voice matters. Your seat at the table is waiting. See you next time!

2. 

   22 Oct 2026

   Why Is It So Hard to Talk About Yourself? | Confidence, Networking & Mirror Talk

   Ever walk into a networking event feeling pretty good about your business, only to completely forget how to explain what you do the second someone asks? Or catch yourself downplaying your accomplishments, minimizing your expertise, or adding a quick “but...” every time you say something positive about yourself? Why do we do that?! We're continuing our Spooky Season series on The Boss Society Podcast, where we're exploring the things that scare us as business owners. And this week, we're talking about something that might be more uncomfortable than we realize: confidently talking about ourselves. Megan is joined by Jenny Murtagh and Felicia Severhill, co-founders of The Parent Empowerment Movement, for a conversation about self-confidence, networking anxiety, self-doubt, and what happens when the person we're most uncomfortable hearing us talk confidently about ourselves is actually us. Together, we're exploring why traditional positive affirmations don't always work, how our deeper beliefs influence the way we show up in business, and a practice called Mirror Talk that can help us build a more authentic relationship with ourselves. And the story behind how Mirror Talk came to be? Let's just say it involves a real-life scary experience and a whole new perspective on confidence. Whether you're struggling to introduce yourself at networking events, confidently communicate your value, or simply acknowledge that you're really freaking good at what you do, this episode is for you. In This Episode, We're Talking About: Why successful women entrepreneurs still struggle to talk confidently about themselves The connection between self-doubt, networking anxiety, and fear of judgment Why positive affirmations alone don't always create lasting confidence What Mirror Talk is and how to start practicing it How our internal beliefs influence selling, pricing, visibility, and business decisions Why genuine confidence doesn't require being the loudest person in the room Connect with Jenny + Felicia Jenny and Felicia are the co-founders of The Parent Empowerment Movement, helping parents move beyond guilt, overwhelm, and unrealistic expectations to create lives that reflect their own values, priorities, and capacity. Website: https://www.theparentempowermentmovement.com/ (https://www.theparentempowermentmovement.com/) Instagram: https://www.instagram.com/theparentempowermentmovement/ (https://www.instagram.com/theparentempowermentmovement/) Podcast: Perfectly Imperfect: Embracing Real Motherhood https://podcasts.apple.com/us/podcast/perfectly-imperfect-embracing-real-motherhood/id1839017817 (https://podcasts.apple.com/us/podcast/perfectly-imperfect-embracing-real-motherhood/id1839017817) 🎙️ HOT MIC: A Live Podcast Experience Everyone is telling you what to post in 2027. We're talking about everything else. We're taking The Boss Society Podcast OFF the mic and ONTO the stage for an afternoon of unfiltered conversations, fresh perspectives, and real connection! Join us for HOT MIC: A Live Podcast Experience, where we're bringing together incredible women in business to talk about marketing beyond social media, building community, getting your business found, and creating opportunities that don't depend on an algorithm. Expect live podcast conversations, honest hot takes, audience participation, and plenty of opportunities to connect with other ambitious women who are building businesses on their own terms. Friday, January 15, 2027 2:00–5:00 PM Centralia Square Ballroom | Centralia, WA 🎟️ General Admission: $97 💋 VIP After Hours: $147, including exclusive post-show time to connect with our speakers and guests. This isn't another afternoon of being told to post more content. We're talking about everything else that helps a business grow. Grab your ticket and learn more: https://olympiabosssociety.com/hotmic (https://olympiabosssociety.com/hotmic) Love The Boss Society Podcast? If this episode resonated with you, share it with a fellow woman business owner who needs the reminder that she doesn't have to downplay her accomplishments to make other people comfortable. And if you're enjoying the podcast, be sure to follow the show and leave a five-star rating or review! It helps more women entrepreneurs discover these conversations and become part of our community. Follow along and stay connected: https://olympiabosssociety.com/ (https://olympiabosssociety.com/) Because you deserve to feel just as confident talking about what you do as you are actually doing it. 🤍 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 (https:// www.olympiabosssociety.com) 🎙️ Want to be a guest? Apply HERE (https://forms.gle/T4yTgaH5dG2S4dvg7) Your voice matters. Your seat at the table is waiting. See you next time!

3. 

   15 Oct 2026

   From Grief to Growth: Building a Business with Purpose with Niyah McKay

   The Boss Society Podcast | October Spooky Season Series What happens when life takes an unexpected turn and the business you never planned to build becomes something bigger than you imagined? This week on The Boss Society Podcast, Megan sits down with Niyah McKay, founder of Bubble Buddies Mobile Wash & Fold, Washington State's first mobile wash-and-fold laundry service, based in Lacey, WA. Born out of personal loss, caregiving, and injury, Bubble Buddies has grown into a mission-driven business rooted in three values: sustainability, inclusion, and community. Niyah shares how her lived experiences shaped her entrepreneurial journey, why neurodivergent inclusion in the workplace matters, and what business owners can do to create more accessible opportunities. We're also talking about the exciting (and sometimes scary!) realities of business growth as Niyah prepares to open her first brick-and-mortar location and launches a community initiative bringing clean clothing and essentials to families in need. Because sometimes building a successful business isn't just about what you sell. It's about what you make possible for other people. In This Episode, We Talk About: Turning grief, personal challenges, and unexpected life changes into entrepreneurship Building a purpose-driven business without losing sight of profitability and growth Neurodivergent entrepreneurship and creating more inclusive workplaces The challenges neurodivergent young adults face transitioning from education into employment The realities of expanding from a mobile service into a brick-and-mortar business How small businesses can make a meaningful difference in their local communities The First Annual Battle of the Bowls and Bubble Buddies' community voucher program Support Bubble Buddies & Battle of the Bowls First Annual Battle of the Bowls 2026 November 7, 2026 | Vert Chiropractic | Lacey, WA Bubble Buddies is partnering with the Thurston County Resource HUB on a community voucher initiative helping provide clean clothing and linens to families in need. Learn more about the event and how to get involved: Battle of the Bowls 2026 (https://bubblebuddies.us/battle-of-the-bowls-2026) Connect with Bubble Buddies: Instagram: @bubblebuddieswa (https://www.instagram.com/bubblebuddieswa/) Facebook: Bubble Buddies Mobile Wash & Fold (https://www.facebook.com/profile.php?id=61572267011828) 🎤 OBS HOT MIC: A Live Podcast Experience (https://www.olympiabosssociety.com/hotmic) Everyone is telling you what to post in 2027. We're talking about everything else. On Friday, January 15, 2027, Olympia Boss Society is bringing HOT MIC to the Centralia Square Grand Ballroom for an afternoon of unfiltered conversations about marketing, visibility, and growing your business beyond social media. We're bringing together powerhouse women entrepreneurs and marketing experts from across the Pacific Northwest for live podcast interviews, honest conversations, audience Q&A, and the kind of business advice you don't usually hear from a conference stage. Friday, January 15, 2027 Centralia Square Grand Ballroom | Centralia, WA 2:00–5:00 PM Want even more access? Upgrade to HOT MIC: AFTER HOURS, an exclusive VIP experience where the recording ends, but the conversation doesn't. With just 25 VIP tickets available, you'll get special seating during the show and the opportunity to connect with our speakers afterward. Tickets are officially on sale! Learn more OBS HOT MIC: A Live Podcast Experience (https://www.olympiabosssociety.com/hotmic) Connect with Olympia Boss Society The Boss Society Podcast is brought to you by Olympia Boss Society, a community for women entrepreneurs who believe building a business shouldn't mean doing it alone. We're creating spaces for real conversations, meaningful connections, and networking without the ick. Follow along on Instagram: @olympiabosssociety If you loved this episode, share it with another business owner who believes business can be a force for good. And don't forget to follow The Boss Society Podcast so you never miss a conversation! 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 (https:// www.olympiabosssociety.com) 🎙️ Want to be a guest? Apply HERE (https://forms.gle/T4yTgaH5dG2S4dvg7) Your voice matters. Your seat at the table is waiting. See you next time!

Who has been a guest on The Boss Society Podcast

Names identified in recent episode analyses. Showing up to five guests.

• Rachel Rowland
• Sarah
• Amy Carlson
• Anna Fanning
• Katie Fama-Silver

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

7 ratings

Spotify

5.0 / 5

5 ratings

Podcast Authority Score: 51 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

90

Social presence

0

YouTube

0

Engagement

32

Contact The Boss Society Podcast

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.

Questions about The Boss Society Podcast