The Boss Society Podcast

The Boss Society Podcast

Download on the App Store

The Boss Society Podcast episodes

  • 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


    Connect with Bubble Buddies:

    Instagram: @bubblebuddieswa

    Facebook: Bubble Buddies Mobile Wash & Fold


    🎤 OBS HOT MIC: A Live Podcast Experience

    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


    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

    🎙️ Want to be a guest? Apply HERE

    Your voice matters. Your seat at the table is waiting. See you next time!

    50 min
  • The Scary Side of Business Growth: Hiring, Delegating & Building a Team

    The Boss Society Podcast | Spooky Season Series 🎃


    Everyone wants their business to grow, but what happens when that growth means you can't do everything yourself anymore?

    In this episode of The Boss Society Podcast, we're continuing our October Spooky Season series, where we're talking about the parts of entrepreneurship that can feel a little scary. And this week, we're tackling something that sounds exciting in theory but can be downright terrifying in practice: hiring your first employees, building a team, and learning to let go of control.


    I'm joined by Bridget, owner and Master Esthetician of Wildflower Estética, a sustainable skin, wax, and makeup studio in Olympia, Washington. Bridget has been navigating the realities of hiring, training, and growing a business beyond herself, and we're pulling back the curtain on what that process actually looks like.

    Because building a team isn't just about finding someone who can do the job. It's about learning to lead, trusting other people with your reputation, and figuring out how to maintain the values and experience that made your business special in the first place.


    In this episode, we're talking about:

    • Recognizing when it's time to hire and grow beyond yourself
    • The unexpected challenges of hiring and training employees
    • Why delegating can be so difficult for entrepreneurs
    • The difference between maintaining high standards and micromanaging
    • Making the transition from business owner to team leader
    • Hiring people who align with your business values and culture
    • Building a sustainable, values-driven business while growing a team
    • The scary parts of entrepreneurship that turn out to be worth it


    Plus, we're having a little fun with our Spooky Business Rapid Fire, covering hiring red flags, business icks, and the things we'd happily never do again. 👻

    Whether you're preparing to make your first hire, already managing a team, or simply wondering what the next stage of growth might look like, this conversation is a reminder that wanting something bigger doesn't mean you have to feel completely ready for everything that comes with it.

    Sometimes the next level of business requires becoming a different kind of business owner.


    Connect with Bridget & Wildflower Estética

    Wildflower Estética is an Olympia-based sustainable beauty studio offering skin treatments, waxing, and makeup services with a commitment to inclusivity, intentional care, and environmentally conscious practices.

    Find Wildflower Estética: Website: wildflowerestetica.com

    Instagram: @wildflower.estetica

    Book an appointment: Visit Wildflower Estética


    Connect with Olympia Boss Society

    You don't have to figure out every scary part of entrepreneurship on your own.

    Olympia Boss Society is a community for women entrepreneurs in the South Sound who want meaningful connections, real business support, and networking without the ick.

    Through our Connection Nights, member-only experiences, and The Collective, we're creating spaces where women can grow their businesses alongside people who understand what they're building.


    Ready to get in the room?

    Explore Olympia Boss Society, upcoming events, and membership opportunities at olympiabosssociety.com.


    Enjoyed this episode?

    Follow The Boss Society Podcast so you don't miss the rest of our October Spooky Season series, and share this episode with a business owner who's navigating her own scary season of growth.

    And if this conversation resonated with you, leave us a rating or review. It helps more women entrepreneurs find the show!

    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!

    47 min
  • September Reflection: The Plan Changed. The Vision Didn’t.

    There’s something about heading into Q4 that can suddenly make everything feel urgent...

    Finish the year strong. Hit the goals. Launch the thing. Make the money. Plan next year.

    But what actually needs to happen before the end of the year? And what are you allowed to leave unfinished?


    In this September reflection episode of The Boss Society Podcast, I’m looking back at a month that felt like a shift in more ways than one.

    The first in-person round of The Room officially began after a launch that didn’t originally go the way I planned, and sitting around that first table reminded me that sometimes the plan needs to change without the vision changing with it.

    I’m also sharing what September looked like behind the scenes of Olympia Boss Society, what I’m learning about marketing as I get back into cold outreach and grassroots relationship-building, why proximity continues to matter so much in business, and the difference between constantly looking for the next thing and going deeper into what you’ve already built.

    Plus, I’m sharing my monthly card pull for what I’m taking with me, leaving behind, and calling in as we move into October.


    In this episode, we talk about:
    • The pressure to “finish the year strong” heading into Q4
    • What September taught me about proximity and community
    • Finally bringing the first in-person round of The Room to life
    • Why a plan changing doesn’t mean the original vision was wrong
    • Getting back to grassroots, relationship-based marketing
    • Why marketing and creating content aren’t always the same thing
    • Taking time to actually notice what you’ve already built
    • What felt hard and what I’m celebrating from September
    • My September card pulls: Shift: The Way to New Potential, What Does Your Soul Say?, and Accept + Receive
    • What I’m carrying with me into October


    Come to October Connection Night 🎃

    If this episode has you thinking you need more real conversations and more people around you who actually understand what it’s like to build a business, come join us in person.

    Our next Olympia Boss Society Connection Night is October 1st from 5:30–7:30 PM, and we're celebrating spooky season with Halloween Speed Connecting.

    Think speed dating... except instead of looking for a husband, you're meeting local women in business. 😂

    Our costume theme is WITCHES, so interpret that however you'd like. Costumes are encouraged but absolutely not required.

    Connection Nights are built around our favorite kind of networking: Networking Without the Ick. You don't need the perfect elevator pitch, you don't need to know anyone before you walk in, and you don't have to awkwardly figure out who to talk to.

    Come get in the room.


    Grab your October Connection Night ticket HERE


    Listen + Connect

    If this episode resonated with you, share it with another business owner heading into Q4 who might need the reminder that everything does not suddenly have to become urgent.

    And before you jump into October, ask yourself:

    What are you taking with you? What are you leaving behind? And what are you calling in?

    See you next week. 🤍

    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!

    38 min
  • Podcasting Isn't Dead: How to Build Community, Relationships & Business Through Your Show

    Is podcasting still worth it in 2026? If you've ever wondered whether starting (or continuing) a podcast is worth the time, this episode is for you.


    This week, I'm joined by Hayleigh Hayhurst, founder of Espresso Podcast Production, to talk about why podcasting remains one of the most powerful ways to build trust, create genuine relationships, and grow your business, even in an ever-changing digital landscape.

    Together, we unpack the misconceptions around podcasting, what actually helps a show grow, and why the biggest wins often have nothing to do with download numbers.

    Whether you're dreaming of launching your first podcast or looking for fresh motivation to keep showing up, you'll walk away with practical insights and a whole new perspective on using your voice to build community.


    In this episode, we cover:
    • Why podcasting is still one of the best long-term visibility strategies
    • The biggest misconceptions about starting a podcast
    • How podcasts create relationships that social media simply can't
    • Ways podcast guesting can lead to collaborations, referrals, and clients
    • What actually helps a podcast grow sustainably
    • Metrics that matter (and the ones you can stop obsessing over)
    • Simple advice for anyone thinking about starting a show


    About Hayleigh

    Hayleigh Hayhurst is the founder of Espresso Podcast Production, a full-service podcast management agency helping entrepreneurs launch, grow, and manage successful podcasts without the overwhelm of production.

    She also hosts two podcasts, Employee to Boss and Podcast Café, where she shares insights on entrepreneurship, podcast strategy, and building sustainable businesses through authentic conversations.

    When she's not helping clients amplify their voices, you'll likely find her exploring Seattle coffee shops with her rescue dog, Captain.

    Resources & Links


    Connect with Hayleigh:

    • Website: https://www.espressopodcastproduction.com
    • All Links: https://www.espressopodcastproduction.com/links
    • Olympia Boss Society October Connection Night Tickets 👻✨


    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!

    47 min
  • Why You Don’t Need More Business Advice. You Need a Room.

    What if the thing holding your business back isn’t a lack of strategy, information, or another course to take?


    If you’ve been in business for a while, chances are you already know a LOT. The harder part is deciding what actually applies to your business, getting out of your own head, and turning what you know into action.

    In this solo episode of The Boss Society Podcast, Megan is talking about why we sometimes need to stop trying to learn our way out of things we actually need to move through and why the right kind of proximity can be so powerful for women business owners.

    We’re also going behind the scenes of The Room, Megan’s new six-week proximity experience designed to help six women move the work that already matters in their businesses.


    In this episode:

    ✨ Why more business advice isn’t always the answer

    ✨ The difference between an information problem and an implementation problem

    ✨ Why consuming more strategy can sometimes keep us from taking action

    ✨ What makes small rooms and consistent proximity different from traditional networking

    ✨ Why business can still feel lonely even when you have a community around you

    ✨ How the right people can help you see what you can’t see from inside your own business

    ✨ What The Room actually is and who it was created for

    ✨ The question to ask yourself instead of “What else do I need to learn?”

    Six weeks from now, what could actually be different in your business?

    Not what could you learn.

    What could you finally move?


    Join The Room

    The Room is a six-week proximity experience for just six women business owners who have something they’re ready to move.

    Bring the offer, launch, decision, pivot, project, or idea that already matters to your business. Through weekly conversations, strategy, accountability, and Voxer support between sessions, we’ll help you stop circling it and start moving it.

    Only a few spots remain.

    👉 [JOIN THE ROOM]


    Ready to Connect with Olympia Boss Society?

    Come join us at September Connection Night on September 10 for an evening of intentional connection with local women business owners, plus a workshop with Shauna Stewart of Pleasure Atelier on Pleasure as Leadership Intelligence.

    Because networking doesn’t have to feel transactional, awkward, or like one more thing you have to perform your way through.

    👉 [GET YOUR CONNECTION NIGHT TICKET]


    Connect with Megan + Olympia Boss Society

    Follow Olympia Boss Society on Instagram and stay connected for upcoming events, business conversations, community opportunities, and new episodes of The Boss Society Podcast.

    If you loved this episode, subscribe to the show and share it with another woman in business who might need the reminder that she probably doesn’t need more information. She might just need the right 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!

    28 min
  • 9 Things I’m Leaning Into in Year 39 | August + Birthday Reflection

    What happens when the version of you from last August wouldn’t recognize the version of you sitting here today?

    In this birthday episode of The Boss Society Podcast, Megan is closing out August and stepping into 39 with a deeply personal reflection on business, relationships, ambition, community, and what success actually looks like in this season.


    After a year filled with incredible moments and some really hard ones, Megan shares the nine anchors she’s carrying into her final year of her thirties, from simplifying her business and protecting her energy to choosing deeper relationships, playing more, trusting herself sooner, and learning to celebrate what she’s already built.

    She also gets candid about a launch that flopped, why she chose to rebuild The Room instead of abandoning the idea, and what failure can teach us when we’re willing to listen instead of immediately moving on.

    And underneath all of it is a bigger reflection: sometimes becoming stronger doesn’t mean being unaffected. Sometimes it means letting something change you without letting it make you smaller.


    In this episode, we talk about:

    • Why simplicity doesn’t mean playing small
    • Relationships over reach in a changing marketing landscape
    • Protecting your energy as a real business strategy
    • Building your business around your actual life
    • Learning to recognize when something is already enough
    • Making room for play, hobbies, fun, and experiences that don’t need to become content
    • Navigating changing relationships and becoming clearer about the people you want around you
    • What Megan learned from one of her hardest seasons personally
    • The failed first launch of The Room and why she decided to rebuild it
    • Why small rooms and deeper relationships are becoming increasingly important in business
    • Redefining success as something you get to experience now, rather than something you’re constantly chasing


    GET IN THE ROOM

    The Room: A Six-Week Proximity Experience is officially open.

    Six women. Six weeks. One thing you’re finally ready to move.

    Bring the offer, launch, decision, idea, or business goal you’ve been circling, and we’ll build your six-week roadmap together. Then you’ll have weekly conversations, coaching, masterminding, accountability, and the proximity of a small group that actually knows what you’re working toward.

    There are only six seats, because the smallness is the whole point.

    [JOIN THE ROOM]


    SEPTEMBER CONNECTION NIGHT

    Join Olympia Boss Society on September 10 for Pleasure as Leadership Intelligence with Shauna Stewart of The Pleasure Atelier.

    We’re exploring what happens when discipline, drive, and responsibility aren’t the only things fueling the way you lead, and how pleasure can expand your capacity for creativity, discernment, boundaries, connection, and leadership.

    Plus, experience our signature Networking Without the Ick and connect with incredible women in business right here in Olympia.

    [GRAB YOUR CONNECTION NIGHT TICKET]

    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!

    38 min
  • Leadership Lessons Every Woman Business Owner Needs to Hear

    What does it actually take to become a confident leader, especially when you don't feel completely ready for the role?


    In this episode of The Boss Society Podcast, we're continuing the Bare Minimum Summer Series with a conversation about a different kind of simplicity: trusting yourself enough to lead without believing you need to have every answer first.

    Megan sits down with Cheryl Selby, longtime Olympia community leader, former small business owner, and former Mayor of Olympia. Cheryl served two terms as Mayor from 2016 to 2023 after two years on City Council. Before stepping into public leadership, she owned Vivala, a women's clothing store in downtown Olympia. Today, she serves as President of the Olympia Arts & Heritage Alliance and remains deeply involved in community and civic leadership.


    Together, Megan and Cheryl talk about what it really looks like to step into leadership before you feel qualified, stay grounded when leadership gets difficult, navigate conflict with poise, and find your voice when you're the only woman in the room.


    In This Episode, We Talk About:
    • Cheryl's journey from small business owner to Mayor of Olympia
    • Why you don't have to feel completely ready before stepping into leadership
    • The merit behind "fake it until you make it"
    • How confidence is built through experience, not before it
    • Staying inspired when leadership gets hard
    • Navigating criticism and conflict without losing yourself in it
    • What Cheryl learned from being the only woman in the room
    • Why your motivations matter when stepping into leadership
    • The importance of surrounding yourself with people who know more than you
    • Leadership lessons women business owners can apply to their own businesses and communities

    Whether you're leading a team, growing a business, building a community, or simply trying to trust yourself in your next season, this conversation is a reminder that leadership doesn't begin when you finally feel ready. Sometimes it begins when you decide to step forward anyway.


    Connect with Cheryl

    Learn more about Cheryl's current work with the Olympia Arts & Heritage Alliance and the Olympia AHA Museum and Visitor Center HERE


    Connect with Olympia Boss Society

    Ready to stop doing business alone?

    Join us for our September Connection Night: Pleasure as Leadership Intelligence, featuring Shauna Stewart of The Pleasure Atelier.

    We're exploring a different kind of leadership conversation: what if the fuel you're missing isn't more discipline, drive, or resilience, but pleasure?

    Shauna will guide us through how expanding our capacity to feel, receive, desire, and experience pleasure can also expand our capacity for discernment, boundaries, creativity, connection, and leadership.

    And, of course, we'll have plenty of time for what Olympia Boss Society does best: Networking Without the Ick and meaningful connection with other local women in business.

    Grab your ticket to September Connection Night and come get in the room with us.


    This Episode is Sponsored By9 Grand Events and Services

    9 Grand Events and Services is an autism-owned company that works with people with physical and intellectual disabilities.

    Since 2000, 9 Grand has provided catering for weddings, corporate events, and social gatherings, along with unique character events featuring famous characters.

    Whether you're planning a wedding, business event, or celebration, 9 Grand Events and Services can help bring it to life.

    Learn more at 9grandevents.com.


    Listen + Subscribe

    If you enjoyed this episode, make sure you're subscribed to The Boss Society Podcast so you don't miss the rest of our Bare Minimum Summer Series.

    And if this conversation made you think of another woman who's stepping into a bigger season of leadership, send this episode her 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!

    54 min
  • A Bare Minimum Summer Guide to Networking

    Summer has a way of changing everything...

    Schedules get busier, routines shift, vacations fill the calendar, and suddenly networking events and coffee chats don't feel quite as doable. If you've found yourself wondering how to stay connected to your business without spending your summer hustling, this episode is for you.

    In this week's Bare Minimum Summer Series episode, we're rethinking networking. Instead of focusing on attending more events or meeting as many new people as possible, we're talking about the small, intentional ways to stay connected that actually build lasting relationships.


    In this episode, we cover:
    • Why networking is about relationships, not events
    • The difference between growing your network and nurturing it
    • A simple three-step networking plan that fits into your summer
    • Easy ways to stay visible without adding more to your calendar
    • Why consistency matters more than quantity when it comes to building meaningful connections

    Whether you're traveling, spending more time with family, or simply protecting your energy this season, you'll leave with practical ways to keep your relationships growing without feeling like you're constantly "networking."


    Your Bare Minimum Networking Challenge

    This week, instead of trying to attend every event, focus on these simple connection points:

    🤍 Reach out to one person you've been meaning to reconnect with.

    🤍 Reply to a few Instagram stories or send a thoughtful message.

    🤍 Invite one person to coffee or a walk.

    🤍 Follow up with someone you met earlier this year.

    Small moments of connection often create the biggest opportunities.


    Mentioned in this Episode

    ✨ Olympia Boss Society Collective Membership

    A welcoming community for women entrepreneurs who believe business grows through genuine connection, collaboration, and support.

    https://www.olympiabosssociety.com/collective

    🎙️ Join us for an upcoming Connection Night

    https://www.olympiabosssociety.com/events


    Connect with Megan

    Instagram:

    https://www.instagram.com/themegangillespie


    This Episode is Sponsored By


    9 Grand Events and Services

    An autism owned company the works with people with physical and intellectual disabilities.

    9 Grand has beenproviding wedding catering, corporate events and social events and character events. since 2000.

    Learn more at www.9grandevents.com


    If You Enjoyed This Episode...

    If this episode encouraged you, I'd be so grateful if you shared it with another business owner who's trying to balance building a business with actually enjoying their summer.

    And if you haven't already, be sure to subscribe so you don't miss the rest of our Bare Minimum Summer Series, where we're simplifying the strategies that matter most.

    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!

    14 min
  • How to Simplify Your Business with Better Systems, Smarter Technology & Less Hustle

    What if technology could actually make your life feel lighter?

    In today's episode of The Boss Society Podcast, Megan sits down with Kyra Delaney, solo indie app developer and founder of SimplyKyra, to talk about simplifying life and business through intentional systems and thoughtful technology.


    Instead of chasing every new productivity hack or app, Kyra shares how she builds tools that quietly reduce mental load, helping people spend less time remembering tasks and more time living their lives.

    Together, Megan and Kyra explore why simplicity is often the smartest strategy, how thinking about your "future self" can change the way you make decisions, and why sustainable businesses are built through intentional systems, not constant hustle.


    Whether you're feeling overwhelmed by your growing to-do list, curious about AI, or simply looking for ways to create more breathing room in your business, this conversation offers practical ideas you can start using today.


    In this episode, we discuss:

    ✨ What it really means to be a solo indie app developer

    ✨ Why simplicity has become the foundation of Kyra's business

    ✨ The surprising reason programmers say "good developers are lazy"

    ✨ How creating simple systems reduces decision fatigue and mental load

    ✨ The power of asking, "What would future me thank me for?"

    ✨ Building technology that supports your life instead of demanding more attention

    ✨ Practical ways entrepreneurs can simplify recurring tasks

    ✨ How to build a sustainable business without falling into hustle culture

    ✨ Small changes that can make your business (and life) feel significantly lighter


    Connect with Kyra

    https://www.simplykyra.com

    https://apps.apple.com/us/developer/simplykyra-llc/id1650115619

    https://www.instagram.com/simplykyraapps/


    This Episode is Sponsored By


    9 Grand Events and Services

    An autism owned company the works with people with physical and intellectual disabilities.

    9 Grand has beenproviding wedding catering, corporate events and social events and character events. since 2000.

    Learn more at www.9grandevents.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!

    37 min
  • Mid-Summer Reset | Bare Minimum Summer Series

    Summer has a way of pulling us in a hundred different directions. Routines shift, vacations happen, the kids are home, and before we know it, we're wondering if we've somehow fallen behind.

    In this solo episode of The Boss Society Podcast, Megan shares a gentle mid-summer reset designed specifically for entrepreneurs who want to move into August with more clarity, intention, and less pressure.

    Instead of focusing on productivity or trying to "catch up," this episode invites you to pause, reflect, and reconnect with what actually matters in this season of business and life.


    In this episode, we'll talk about:
    • Why taking a break doesn't mean you have to "make up" for lost time
    • Four powerful questions to help you reset before August
    • How to recognize what's quietly working in your business
    • What you may be carrying simply out of habit
    • Creating a business that supports your life instead of competing with it
    • One simple exercise to help you finish the summer with clarity and momentum


    Whether your summer has been productive, chaotic, restful, or somewhere in between, this conversation will remind you that sustainable growth isn't built through constant hustle... it's built through intentional, consistent action.


    This Episode's Bare Minimum Challenge

    Grab a notebook and write down:

    🤍 One thing you'll keep doing because it's working.

    🤍 One thing you'll release because it no longer fits this season.

    🤍 One thing you'll commit to doing before Labor Day.

    Small, intentional steps create lasting momentum.


    💕 Q3 OBStie Spotlight

    A huge shoutout to this month's incredible OBSties! These members help make Olympia Boss Society the welcoming, supportive community it is. If you're looking for amazing local businesses to support, be sure to check them out!

    • Senior OBStie | Bryn Silver, The Ease Project
    • Kyra Delaney, iOS & macOS App Developer
    • Elmara Baisubanova, Elmira Captures
    • Andrea Shamansky, Reverie Images
    • Angie Sherrer, Bespoke Cocktails Mobile B


    Interested in becoming an OBStie or joining the Olympia Boss Society community? We'd love to have you. Visit olympiabosssociety.com/obsties to learn more! 💛


    👀 What's Coming Up at Olympia Boss Society

    ✨ August Connection Night | August 6

    Join us for an evening of networking without the ick and a practical LinkedIn workshop with Andrea Florescu of Smart Brand Ideas.

    You'll learn:

    • How to optimize your LinkedIn profile in minutes
    • A simple content strategy that fits your schedule
    • How to turn connections into real opportunities
    • AI-powered workflows to save time and stay consistent

    Whether you're brand new to LinkedIn or ready to use it more intentionally, you'll walk away with practical strategies you can implement right away.


    📝 Content Lab | August 14

    Our quarterly Content Lab is back! This hands-on working session is designed to help you stop staring at a blank screen and finally make progress on your content.

    Bring your laptop, your ideas (or lack of them!), and spend focused time creating alongside other women business owners. You'll leave with content completed, fresh ideas, and momentum you can carry into the rest of the month.


    🎟️ Learn more and register for both events at olympiabosssociety.com/events. We can't wait to see you there!

    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!

    21 min

About The Boss Society Podcast

From the publisher's feed

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…