Your Conversation Pit

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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.

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Let’s Keep the Conversation Going Online:

@ashleighchenry on Instagram and Linkedin

@ashchenry on Substack 

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!

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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/

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®

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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 

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.

| 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 |

Crafting a Strategic and Intuitive Annual Plan 

How to Annual Plan 2025 With Ease and Harmony at the Helm

Part II: How to Annual Plan 2025 With Ease and Harmony at the Helm
Mastering Sales Psychology in 2024 and Beyond
The Art of Sales Psychology Starts with This
5 Lessons if You’re Pivoting from Agency to Consulting Firm and Educational Hub

Holistic Harmony Can Exist Within Your Life and Business

Balance is a Myth: Embrace Holistic Harmony Instead

Paige Hulse for Legal Needs and Staying Up to Date on AI Law

| 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:

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 creating an intuitive and impactful business strategy that aligns with both your long-term vision and day-to-day realities. By focusing on vision mapping, sustainable growth, and intentional planning, founders can structure their year for both profitability and peace. We discuss practical steps like setting clear boundaries, mapping revenue streams, and automating essential tasks to avoid burnout and keep your business flowing smoothly. This approach combines intuitive decision-making with structured planning, empowering founders to grow their businesses while maintaining harmony in their personal lives.Key Points:

1. Vision Mapping: Visualize your goals and integrate your word of the year into a roadmap that guides your decisions. Using your intuition can create a balanced, intuitive approach to business that supports growth without sacrificing peace.
2. Holistic Harmony in Life and Business®: Ensure your business and personal goals align. This type of annual planning helps maintain the peace you’ve worked to create, rather than disrupting it. Strong boundaries and a focus on self-care are foundational for harmony.
3. Non-Negotiables: Create non-negotiable time for activities that support your well-being, like family dinners and workouts, even during demanding seasons.
4. Mapping Revenue Streams: This episode provides strategies for planning multiple revenue streams, from workshops and digital products to retreats, that match your energy and long-term vision.
5. Delegation and Efficiency: Learn how to use your team for content repurposing and automations, allowing you to focus on high-impact tasks without burning out.
6. Filling the Funnel: Increase client touchpoints by implementing a clear funnel strategy, integrating both free and paid offerings, to create a sustainable, profitable, and peaceful business.
7. Work-Life Balance: We encourage female founders to approach 2025 with a blend of structure and intuition, automating where possible to maintain a balance between business growth and personal fulfillment.

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.

| 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 |

Crafting a Strategic and Intuitive Annual Plan 

Holistic Harmony Can Exist Within Your Life and Business

Balance is a Myth: Embrace Holistic Harmony Instead

@imanixnicole on TikTok (Pinterest board an

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

In this episode of Your Conversation Pit®, I dive into strategies female founders can use to plan for 2025 with intention, ease, and harmony. We explore how to reflect on your business year, balance business and personal growth, and use systems and automation to avoid burnout. Whether you're looking to realign after 2024 or implement streamlined workflows for a banner year, this episode will offer actionable tips for consistent success.

My positive focus today is reflecting on how grateful I am to travel safely while my hometown in Western North Carolina deals with a devastating natural disaster. Asheville and surrounding areas are resilient, but they need support. In this episode, I urge listeners to help these mountain towns rebuild and provide options for supporting local communities.

In this episode, I also share our personal journey of reconfiguring The Cheetah Company® and starting Stay at Harmony. It has been a year of internal evolution, a death and rebirth, if you will. 

Key Points:

1. Reflection and Realignment: Start your 2025 planning by reflecting on what worked and didn’t work in 2024. Realignment is key to avoiding another chaotic year and creating harmony between personal and business growth.
2. Ease with Structure: An intentional, structured annual plan brings ease. In our world of constant projects and launches, harmonizing business and personal life is essential for sustainable growth.
3. Quarterly Reviews: Set up quarterly review checkpoints to assess your energy, alignment, and business direction. Quarterly reflection can prevent burnout and misaligned goals.
4. Business Planning Through Consistency and Automation: Consistency is the foundation of ease, while automating workflows (like marketing and sales) helps female founders avoid burnout and free up time for creativity and high-impact tasks.
5. Sexy Automations: Implementing “sexy automations” simplifies lead nurturing and allows more time for what matters—without the stress of high-energy launches.

| 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 |

Crafting a Strategic and Intuitive Annual Plan 

| 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:

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

In this episode of Your Conversation Pit®, I explore unconventional approaches to sales that prioritize relationship-building, personal branding, and emotional resilience over traditional marketing tactics. Female founders can master sales by focusing on psychology, tailored communication, and self-development. Rather than relying on ads and complex software, creating personalized outreach and genuine connections is a far more impactful strategy. Additionally, balancing business growth with personal life and inner growth is crucial for long-term success. Learn how to harmonize these elements to foster both personal and professional development.

Key Points:

1. Understanding Sales Psychology: Female founders can enhance client engagement by focusing on personalized communication and understanding what drives their clients' decisions, which leads to better retention and relationship-building.
2. Personal Branding and Sales Success: Building a strong personal brand helps attract the right clients and makes closing deals easier. Authenticity and consistency are key to creating meaningful connections.
3. Sales Skills Over Marketing Tactics: Rather than relying heavily on ads or software, founders should hone their sales techniques, which often yields higher returns. Following up and emphasizing the value of their service can create a more personalized sales experience.
4. Tailored Communication and Social Media Engagement: Crafting personalized outreach messages and leveraging video content can significantly enhance client relationships. On social media, focus on starting conversations and sharing user-generated content to build engagement.
5. Avoiding Over-Reliance on Ads and Heavy Software: Personal engagement and organic practices like networking or consistent email communication often produce better results than costly advertising campaigns.
6. Balancing Business Growth with Personal Development: Achieving a healthy balance between business and personal life through time management and delegating tasks is key to long-term success. Founders should also focus on personal development to drive business growth.
7. Navigating Challenges with Emotional Resilience: Mindfulness practices and reframing setbacks can help female founders maintain emotional resilience, crucial for overcoming obstacles and sustaining business expansion.

| 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 |

Balance is a Myth: Embrace Holistic Harmony Instead

10 Signs that You’re Evolving & Expanding in Your Life and Business.

Holistic Harmony Can Exist Within Your Life and Business

| LEARN MORE | 

The Cheetah Company: www.thecheetahcompany.com

Becom

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

In this episode of Your Conversation Pit®, I discuss why I often decline clients who lack personal vision, confidence, and leadership, no matter how ambitious their business goals are. Without a clear personal brand or strong self-development, business growth is often halted. Female founders must align their personal vision with business strategy to see meaningful progress. Clients who expect external solutions without owning their journey struggle to lead their businesses, and indecision becomes a constant roadblock.

Key Points:

1. Lack of Personal Vision: Personal branding and business growth are tied together. Clients without clear visions expect others to solve their problems, but success requires self-reliance and decision-making.
2. Absence of Inner Confidence and Leadership: CEOs lacking self-belief can’t lead themselves or their teams effectively. Emotional resilience is key, and without it, business strategy alone won’t drive results.
3. Failure to Execute: Business growth relies on consistent action. Clients who procrastinate or fail to implement strategies halt progress, leaving both themselves and consultants frustrated.

| CONTINUE THE CONVERSATION | 

Send us a text message through your podcast catcher

| RESOURCES MENTIONED |

Business Strategy is a Small Fraction of Your Business Success as a Female Founder

Balance is a Myth: Embrace Holistic Harmony Instead

10 Signs that You’re Evolving & Expanding in Your Life and Business.

Holistic Harmony Can Exist Within Your Life and Business

| LEARN MORE | 

Stay at Harmony: airbnb.com/h/stayatharmony

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 

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

In Season 2, Episode 22 of Your Conversation Pit™, we delve into what’s *actually* working for B2B marketing in 2024. Your communities are more savvy and discerning than ever when they’re approaching their investments – especially if you’re working with a high caliber clientele. They’ve been burned too often by high-ticket masterminds. 

This episode provides a high-level overview of tactics to insert into your fall launches for more profit, peace, producitivity, and play than ever before.

Key highlights include: 

• Mastering Fall Launches: Practical Tactics for High-Caliber Entrepreneurs
• The Non-Launch Launch: Profitable Marketing Without Ads, Funnels, or Affiliates
• Building Community Over Cash: The Key to Sustainable Business Growth in 2024
• The Society of More: Integrating Purpose into Your Business for Greater Impact
• Personal Branding with Purpose: How to Stand Out in a Saturated Market
• Overcoming Content Saturation: What Your Clients Really Want from Your Brand

Resources & Links to Continue the Conversation

Send us a text message through your podcast catcher

The Harmonious Business Mini-Mind Brochure

The Harmonious Business Mini-Mind Application

Other episodes mentioned: 

Marketing Strategies That Are Working in 2024, The Current State of Online Businesses, and What To Do About It

Business Strategy is a Small Fraction of Your Business Success as a Female Founder

Balance is a Myth: Embrace Holistic Harmony Instead

10 Signs that You’re Evolving & Expanding in Your Life and Business

Other links mentioned: 

7-in-1 Dirt Devil Steamer.

Lyndsey Chambers

FoundationInc

OnAudience

Learn more about 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:

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 are getting into the nitty gritty of what effective business consulting looks like, what it means to invest in yourself and business as a female founder, the strategies behind creating business transformation, and if you feel safe enough to achieve the goals you’re setting. 

Key highlights include: 

• Investing in your own well-being as a female founder is a business growth strategy in 2024
• Knowing that your self-trust as a female founder is the key to your longterm success (regardless of how often you invest in mentorship and support)
• Your unique baseline of safety and joy will impact how much success you feel comfortable with
• How your background and trauma experiences can affect your business choices
• Building business transformation stories starts with belief in your own success first
• Why networking and community building are essential for business development

Resources & Links to Continue the Conversation

Mentioned in the Episode:

Podcast Episodes:
Harmonizing Masculine and Feminine Energetics in Life and Business
Balance is a Myth: Embrace Holistic Harmony Instead

Data and Quotes:

Stephen Hunt 

Nigel Frank International

Send us a text message through your podcast catcher!

The Harmonious Business Mini-Mind Brochure

The Harmonious Business Mini-Mind Application

Learn more about 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