In this celebratory solo episode, Megan Gillespie reflects on two years of building Olympia Boss Society from scratch. What started as a single networking night has grown into a movement—one built not on polish, but on people. She shares the real story behind OBS, how vulnerability became the foundation for connection, and why leadership doesn’t have to mean being the loudest in the room. You’ll also get the full breakdown of all the local events happening in May—and exactly how to plug in if you're craving deeper connection in your business and life.

• Community changes everything.
• Vulnerability creates belonging.
• Perfection disconnects, but humanity invites.
• Be the first one to go first.
• People are craving the real you.
• Your people are waiting—and they can’t find you if you’re hiding.

00:00 — The Birth of Olympia Boss Society

12:06 — Community Building and Its Impact

20:54 — Lessons Learned & What’s Coming This May

Local to Olympia? Come celebrate 2 years of OBS at one of our May events! Whether you’re new or returning, there’s a space waiting for you. ✨

• Join Olympia Boss Society Events & Membership

☕ Coffee & Convos | May 7

Real convos over coffee—zero pressure.

Perfect first event if you're brand new and want to ease in gently.

🥂 Connection Night: 2-Year Anniversary | May 12

Panel, networking, local spotlights, and celebration.

Perfect first event if you're ready to feel the full energy of OBS.

💻 Content & Co-Working | May 23

Work time meets community time—bring your laptop and your goals.

Perfect first event if you're craving productivity and connection.

💃 Founders & Fitness | May 26

90s Dance Night! No pressure, just fun and movement.

Perfect first event if you want to meet people in a playful, low-key way.

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!

In this week’s episode of The Boss Society Podcast, Megan sits down with Kristy Cruz—military spouse, mom of three, and founder of The Succulent Studio. Kristy didn’t start her business until later in life—and now she’s teaching workshops, running a thriving succulent brand, and inspiring women to pursue their passions at any age.

Together, they talk about the realities of building a business while working a 9-to-5, setting boundaries with your time and energy, and finding peace through plant care. From cultivating community to hosting creative workshops, Kristy shares her story of resilience and growth—reminding us it’s never too late to start something new.

Key Takeaways:

• It’s never too late to pursue your passion.
• Boundaries are essential to protect your energy and your vision.
• Plants can be powerful tools for mental wellness and confidence.
• Community support makes entrepreneurship less lonely—and more fun.
• Every part of your journey matters—even the messy middle.

Chapters:

00:00 – Starting a Business Later in Life

10:00 – Balancing Work, Family, and Plants

18:00 – The Mental Health Benefits of Plant Care

34:00 – Building Confidence Through Workshops

49:00 – Community, Creativity & Growth

Special Offer:

Want to host a succulent workshop, learn more her upcoming events, or grab one of Kristy’s signature disco-ball planters?

Connect with Kristy @thesucculentstudio on Instagram or visit https://thesucculentstudio.squarespace.com/ to learn more.

Links Mentioned:

• Kristy Cruz on Instagram: @thesucculentstudio
• Book a workshop or planter: https://thesucculentstudio.squarespace.com/
• Get on Kristy's newsletter: https://thesucculentstudio.myflodesk.com/newslettersignup

Love the show?

Share this episode with your favorite plant-loving business bestie or leave a review ts to help more women find these powerful conversations.

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!

This episode contains discussion of sexual abuse, eating disorders, and religious trauma, as well as candid talk about body image and intimacy. Please listen with care and skip any section that feels unsafe for you.

How much of your business do you hold back because of how you feel in your body? Body‑ and sex‑positive artist, kink‑educator, and intimacy coach Tiffany Nickel joins Megan to unpack the hidden link between body image and business visibility. From hiding behind logos to dreading live video, they explore why stepping up as the face of your brand feels so vulnerable—and how to do it anyway. Expect somatic tools, mindset shifts, and real‑life stories that prove your body is not a barrier to marketing, networking, or leadership; it’s part of your power.

• Visibility lives in the body first—image stories shape how boldly we market.
• Own the room—even if you’re shaking; most people worry about themselves, not you.
• Dress, speak, & show up for you, not an idealized “professional look.”
• Curate your feed with diverse, authentic creators to retrain beauty standards.
• Action > perfection—confidence grows after you show up, not before.
• Your body changes—your mission doesn’t. Lead anyway.
• 
  

• Connect with Tiffany: Instagram | Website
• "Unbound" an Anti‑Diet Culture Immersive Art Experience — Opening Night Apr 24, 2025 at Studio Hanson, Olympia: Get Your Ticket HERE

00:00 – Body image as the hidden business barrier

08:10 – Somatic tools for camera & stage nerves

15:14 – Motherhood and shifting self‑perception

34:18 – Branding authentically when you don’t fit the “ideal”

58:21 – Networking confidence & dressing for yourself

01:11:13 – Action over perfection: rewriting your leadership story

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!

In this episode of The Boss Society Podcast, host Megan Gillespie shares a raw & honest perspective on what it really takes to build meaningful connections through networking—especially at the local level.

From dreading networking events to now hosting them through Olympia Boss Society, Megan walks listeners through the mindset shifts, strategies, and personal growth that come from showing up with intention. You’ll learn how to make networking feel less transactional and more transformational, both in-person and online.

Whether you're brand new to networking or looking to deepen your community, this episode will leave you feeling grounded, prepared, and empowered to connect with purpose.

Key Takeaways:

• Networking is a long-term investment in relationships
• Show up with a clear purpose and a mindset of service
• Listening creates the space for deeper, more authentic connections
• One event won’t change everything—consistency is key
• Following up is where the magic happens
• Blend local and virtual networking to expand your reach
• Building community enhances every part of your business
• 
  

Special Offer:

💡 Ready to find your people and grow your business? Join Olympia Boss Society and get access to curated local events, supportive connections, and opportunities to build real relationships. Click here to learn more.

Links Mentioned in This Episode:

• Join Olympia Boss Society Collective membership: Learn More
• Join for April Speed Connecting: Event Sign-Up

Chapters:

07:07 – Strategic Local Networking: A Game Changer

12:23 – Reframing Networking Mindset

18:23 – Finding the Right Networking Events

24:51 – Listening: The Key to Meaningful Connections

29:52 – Post-Event Strategies for Continued Engagement

37:52 – The Journey of Networking: Building Relationships

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!

In this episode of The Boss Society Podcast, host Megan Gillespie sits down with personal brand photographer Deedre to talk about the power of showing up—visually and energetically—as the face of your business.

Together, they explore how brand photography builds more than just your image—it builds trust, confidence, and connection. From overcoming imposter syndrome to finding your energy in front of the camera, this conversation is an empowering reminder that your presence is your power.

Key Takeaways:

• Brand photos tell your story and build trust.
• Confidence grows with practice.
• Community helps you show up.
• Your brand should look like you.
• Start before you feel ready.

Chapters:

00:00 – The power of personal branding in photography

06:42 – Building confidence through visual storytelling

12:16 – Empowering moments behind the lens

19:03 – Overcoming imposter syndrome and self-doubt

24:20 – Community, connection, and showing up

31:59 – Leveraging your brand photos with purpose

35:58 – Staying consistent and claiming your space

Special Offer:

🔥 Use code "Branding Bestie" when you book your discovery call for as special discount!

Links Mentioned in This Episode:

• Connect with Deedre: Instagram 
• Learn more about Olympia Boss Society: olympiabosssociety.com
• Join Cultivate Like a Boss Waitlist: Sign Up Here

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!

In this episode of The Boss Society Podcast, Megan Gillespie sits down with Danielle Moran to explore the courage it takes to chase your dreams — even when fear tries to hold you back. Danielle shares her experience of navigating entrepreneurship, the lessons learned along the way, and the importance of leaning on your community for support.

From recognizing your worth to embracing the messiness of growth, this conversation is an inspiring reminder that fear doesn’t have to stop you. Whether you’re launching something new or navigating a tough season, this episode will leave you feeling empowered to take the next step.

Key Takeaways:

• Fear is a normal part of growth, but it doesn’t have to hold you back.
• Asking for help is a strength, not a weakness.
• Community support can make all the difference.
• Confidence is built through action — not waiting for fear to disappear.
• The people you surround yourself with impact your growth and success.
• Facing challenges can lead to unexpected opportunities.
• Self-talk and mindset shifts are powerful tools for navigating fear.
• You don’t have to figure it all out alone.
• 
  

Links Mentioned in This Episode:

• Connect with Danielle Moran: Instagram | Website
• Join Olympia Boss Society: Learn More

Loved this episode?

If this conversation resonated with you, we’d love to hear from you! Tag us on Instagram and share your biggest takeaway. And if you haven’t already, please rate and review the show — it helps us reach more women like you who are building businesses with courage and heart.

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!

In this episode of The Boss Society Podcast, Megan Gillespie sits down with her former co-founder and business bestie, Sophie Burley, to talk about how one unexpected connection can change everything. From meeting in a random Facebook group to building a thriving community together, their journey is a testament to the power of putting yourself out there.

They dive into how authentic relationships can transform your business, why community is essential for women entrepreneurs, and how embracing vulnerability leads to real growth. Whether you're struggling to find your people or hesitant to network, this conversation will inspire you to take the leap.

• Unexpected connections can lead to meaningful relationships.
• Building authentic relationships can transform your life and business.
• Putting yourself out there is essential for growth.
• Real recognizes real — authenticity attracts authenticity.
• Embracing imperfection is part of the journey.
• Community over competition requires inner work.
• Success is often about who you surround yourself with.
• In-person connections deepen relationships.
• You don’t have to wait for others — be the one to reach out.
• 
  

• 00:00 - The Power of Unexpected Connections
• 07:50 - Building Authentic Relationships
• 22:44 - Community Over Competition
• 39:40 - The Impact of Relationships on Success
• 54:49 - Embracing Imperfection in Business
• 01:01:53 - Finding Your People and Building Connections
• 
  

Sophie Burley is a Certified Nutritionist dedicated to helping women ditch restrictive diets and understand their bodies on a deeper level. She focuses on gut health, hormones, and blood sugar balance to empower her clients to make sustainable, nourishing choices—without guilt, calorie counting, or restricting your favorite foods. Through education and a realistic approach, she helps women build a healthier relationship with food, feel their best, and create long-lasting habits for a thriving life.

Follow along with Sophie Burley✨

Instagram: @whatsgoodnutrition 

Facebook: @whatsgoodnutrition   

Youtube: @sophies-world29

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!

In this inaugural episode of The Boss Society Podcast, host Megan Gillespie shares her journey of building community and the evolution of her podcasting career. She highlights why authentic relationships are the foundation of business success and how community-driven strategies are shaping the future for women entrepreneurs. Get ready for real, unfiltered conversations, actionable advice, and insights into 2025 trends that will redefine how we network, collaborate, and grow our businesses.

Key Takeaways:

• Success in business doesn’t happen in isolation—your community matters.
• Relationships and collaboration will take you further than strategies alone.
• Community-based marketing is shaping the future of entrepreneurship.
• Unpolished, authentic content resonates more than perfection.
• Hustle culture and overworking aren’t the only paths to success.
• You don’t have to figure everything out alone—support is available.
• The right people in your corner can transform your business journey.
• Building connections isn’t just about networking—it’s about creating impact.
• 
  

Chapters:

00:00 – Introduction to The Boss Society Podcast

02:04 – The Evolution of Community Building

07:03 – The New Era of Business

10:51 – Trends in Community-Based Marketing

13:53 – Call to Action and Upcoming Events

🔗 Links & Resources Mentioned:

RSVP for the OBS x SWAE Night Market Collab HERE

Check out upcoming LOCAL events HERE

Next Episode Preview:

Stay tuned for an candid conversation with OBS co-founder Sophie Burley, where we dive deep into what it truly means to be in a community that lifts you higher.

💬 Love this episode? Subscribe, leave a review, and share it with a fellow boss who needs to hear this! 🎧

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!

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!