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Your Conversation Pit

Your Conversation Pit

By: Ashleigh Henry
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Your Conversation Pit® Podcast is hosted by Founder and CEO Ashleigh Henry of The Cheetah Company. This is where life & business-changing conversations happen. We’re fusing the past and present, taking a step back in time to the 1950-70s conversation pits that created spaces of true connection over cocktails (or mocktails!), while a record plays in the background. We’re harmonizing lives and businesses, chatting about strategies and innovations for both, all while expanding the conversation beyond the current - and well into the future. Welcome to the pit. Bring a friend, and join the elevation conversation.

© 2025 Your Conversation Pit
Economics Leadership Management & Leadership
Episodes
  • Ep 30 | Not Just a Pivot — A Purposeful Transition into Life Design
    Apr 25 2025

    We love conversing with you. Chat with us in Your Conversation Pit by sending a text message!

    This is the episode I’ve been writing in my body for years. One part closing chapter, one part initiation, this conversation brings you behind the scenes of why I’m closing The Cheetah Company®—the brand that brought me into rooms with the most brilliant female founders and allowed me to serve at the highest level in business advising, coaching, and consulting.

    But this episode isn’t about a pivot in business. It’s about a deeper calling. A reclamation. A reckoning with what happens when success looks incredible on the outside but starts to quietly erode the inside.

    Whether you’ve outgrown the business you built, or you’re navigating your own silent “what now?”—this is a space for your truth to breathe.

    Inside This Episode:

    • Why I’m officially closing The Cheetah Company® after five beautiful years
    • The unseen addictions inside the female founder space: stress, being needed, being known
    • The silent grief that cracked me open and changed the trajectory of my life
    • What happens when ambition goes unchecked—and why so many high-achieving women are quietly asking, “Is this it?”
    • A look at one client’s journey navigating the tension between building her empire and choosing van life
    • The difference between productivity and presence, and how pleasure is often the missing ingredient

    A Look at My Client Work (Then + Now):

    • Supporting multi-six and seven-figure entrepreneurs in seasons of reinvention
    • Holding space for “successful” women as they unedited their lives and quietly unraveled
    • Shifting from strategy-heavy consulting into soulful, somatic, life-based guidance
    • How I moved from helping clients build scalable businesses to helping them build spacious lives

    Key Takeaways:

    1. If you feel like you’re holding it all but losing yourself in the process—you’re not alone.
    2. There’s no business strategy that can make up for a life that feels misaligned.
    3. Real harmony asks us to slow down, feel, and reorient before we build again.
    4. Sometimes your legacy lives on the other side of letting go.

    This work is just beginning. If you’re in a season of softening, surrendering, or shifting, join me over at The Deep Edit — my weekly newsletter where we blend narrative, nuance, and the next evolution of leadership for high-achieving women ready to live differently.

    Subscribe to The Deep Edit to receive your welcome issue and a podcast to anchor you into this next season of life.

    ______

    | CONTINUE THE CONVERSATION |

    Join The Deep Edit – a weekly newsletter full of topics like this podcast episode

    Let’s Keep the Conversation Going Online:

    @ashleighchenry on Instagram and Linkedin

    @ashchenry on Substack

    Show More Show Less
    48 mins
  • Ep 29 - The Client Sessions: Building a Sustainable Business, Annual & Quarterly Planning, Hiring, and Sales Projections
    Feb 20 2025

    We love conversing with you. Chat with us in Your Conversation Pit by sending a text message!

    In this episode, we take you behind the scenes of a private client session focused on building a sustainable business in 2025. We break down tangible actions for annual and quarterly planning, creating a hiring plan, and demystifying sales projections for female founders looking to scale without burnout.

    Inside This Episode:

    • How my latest CEO Day helped me reconnect with my brand’s evolution over the past six years.
    • A deep dive into a client session with a seasoned female founder preparing to scale to seven figures while maintaining a 10-15 hour workweek.
    • Annual and quarterly planning strategies that merge business growth with personal alignment.
    • Hiring plans that ensure operational efficiency without CEO overwhelm.
    • Sales projections simplified—how to forecast revenue while keeping flexibility for real-time adjustments.

    A Look at Our Client’s Journey:

    • A multi-six-figure entrepreneur seeking sustainable growth into the seven-figure range.
    • Expanding her brand beyond a signature program and private client work.
    • Strengthening omnichannel presence through podcasting, blogging, and strategic partnerships.
    • Creating a hiring plan to transition from wearing multiple hats to leading a high-performing team.

    Key Takeaways:

    1. Annual & Quarterly Planning: How to assess past performance and create an actionable plan for sustainable growth.
    2. Hiring Strategies: Identifying the right roles to fill based on time constraints and business needs.
    3. Sales Projections: Forecasting revenue with a balance of structure and fluidity to adapt to real-time business performance.
    4. Building a Sustainable Business Model: Aligning business growth with personal fulfillment and lifestyle goals.

    If you’ve been looking for a way to structure your business while allowing room for creativity, ease, and personal alignment, this episode is for you.

    Let’s Connect: Want to implement a consistent CEO Day into your business? Send me a DM on Instagram with the word CEO, and I’ll share what I went over in my latest session!

    | CONTINUE THE CONVERSATION |

    Send us a text message through your podcast catcher

    | ASHEVILLE RESOURCES TO DONATE & SUPPORT |

    Beloved Asheville

    Hearts With Hands (disaster relief)

    ABCCM (donations for motels, food, and the like)

    Living Document with Local Needs

    | RESOURCES MENTIONED |

    Paige Hulse Law

    The Foundry

    | LEARN MORE |

    The Cheetah Company: www.thecheetahcompany.com

    Become timeless through our signature sales course, The Timeless Sales Method® Course: https://thecheetahcompany.com/sales/

    Apply to work with Ash in private consulting: https://thecheetahcompany.com/empowered-consulting/

    Secure Ash as a speaker for your next experience:

    https://thecheetahcompany.com/press/

    Sip & pour over at The Cheetah Café:

    https://thecheetahcompany.com/blog/

    Show More Show Less
    44 mins
  • Ep 28 - Part II: Top 7 Business Trends for 2025 Every Ambitious Female Founder Needs to Embrace for a Thriving, Softer Life
    Dec 21 2024

    We love conversing with you. Chat with us in Your Conversation Pit by sending a text message!

    In this episode of Your Conversation Pit®, we dive into the business trends that we’ve been noticing for 2025. If you’re a female entrepreneur that’s interested in growing a thriving business and harmonious life, this is your place and space to learn how to prepare for 2025 in a grounded way.

    The Cheetah Company is here to support your 2025 business planning with our consulting expertise, guiding you to transform creative ideas into clear, repeatable actions that drive both personal and business success. If you’re interested in having us by your side through private consulting, reach out to explore how we can support you in creating a banner year in 2025.

    Female Founder Business Growth, Personal Branding for Female Entrepreneurs, Self-Development for Female CEOs, Leadership in Business Strategy, Emotional Resilience for Entrepreneurs, Business Strategy for Women Leaders, Personal Vision for Business Success, Authentic Personal Branding, Entrepreneurial Success Stories for Women, and Holistic Harmony in Life and Business®

    ______

    | CONTINUE THE CONVERSATION |

    Send us a text message through your podcast catcher

    | ASHEVILLE RESOURCES TO DONATE & SUPPORT |

    Beloved Asheville

    Hearts With Hands (disaster relief)

    ABCCM (donations for motels, food, and the like)

    Living Document with Local Needs


    | RESOURCES MENTIONED |

    Wintering by Katherine May


    | LEARN MORE |

    The Cheetah Company: www.thecheetahcompany.com

    Become timeless through our signature sales course, The Timeless Sales Method® Course: https://thecheetahcompany.com/sales/

    Apply to work with Ash in private consulting: https://thecheetahcompany.com/empowered-consulting/

    Be emboldened through these complementary resources: https://thecheetahcompany.com/emboldened-resources/

    Secure Ash as a speaker for your next experience: https://thecheetahcompany.com/press/

    Sip & pour over at The Cheetah Café:

    https://thecheetahcompany.com/blog/


    Let’s Keep the Conversation Going Online:

    www.thecheetahcompany.com

    @thecheetahcompany on Instagram, Facebook, Linkedin, & Pinterest

    @yourconversationpit on Instagram & Facebook

    @ashleighchenry on Instagram

    @stayatharmony on Instagram


    Show More Show Less
    47 mins

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