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Your Conversation Pit
Ashleigh Henry
31 episodes
6 months ago
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...
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Entrepreneurship
Business
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All content for Your Conversation Pit is the property of Ashleigh Henry and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
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...
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Entrepreneurship
Business
Episodes (20/31)
Your Conversation Pit
Ep 30 | Not Just a Pivot — A Purposeful Transition into Life Design
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...
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6 months ago
47 minutes

Your Conversation Pit
Ep 29 - The Client Sessions: Building a Sustainable Business, Annual & Quarterly Planning, Hiring, and Sales Projections
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...
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8 months ago
44 minutes

Your Conversation Pit
Ep 28 - Part II: Top 7 Business Trends for 2025 Every Ambitious Female Founder Needs to Embrace for a Thriving, Softer Life
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, guidi...
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10 months ago
46 minutes

Your Conversation Pit
Ep 27 - Top 7 Business Trends for 2025 Every Ambitious Female Founder Needs to Embrace for a Thriving, Softer Life
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, guidi...
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10 months ago
51 minutes

Your Conversation Pit
Ep 26 - Part II: How to Annual Plan 2025 With Ease and Harmony at the Helm
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 stre...
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11 months ago
49 minutes

Your Conversation Pit
Ep 25 - How to Annual Plan 2025 With Ease and Harmony at the Helm
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 ac...
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1 year ago
55 minutes

Your Conversation Pit
Ep 24 - Non-Conforming Ways to Approach Sales Activities as a Female Founder
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 genuin...
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1 year ago
56 minutes

Your Conversation Pit
Ep 23 - The Clients I Decline as a Business Consultant for Female Entrepreneurs
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 externa...
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1 year ago
50 minutes

Your Conversation Pit
Ep 22 - Unconventional Marketing Methods That Are Working in 2024 and Beyond
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 i...
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1 year ago
55 minutes

Your Conversation Pit
Ep 21 - Business Strategy is a Small Fraction of Your Business Success as a Female Founder
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 fo...
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1 year ago
52 minutes

Your Conversation Pit
Ep 20 - The Anxieties Your Potential Clients Are Feeling (And What To Do About It)
We love conversing with you. Chat with us in Your Conversation Pit by sending a text message! In this episode of Your Conversation Pit, Ashleigh discusses your potential client’s experiences and anxieties before working with you and how to navigate conversations through messaging that leads to conversion. Key highlights include: What your potential clients are actually craving and wanting to see from you through your messaging as an advisor, agency, coach, consultant, and service ...
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1 year ago
59 minutes

Your Conversation Pit
Ep 19 - 5 Lessons if You're Pivoting from Agency to Consulting Firm and Educational Hub
We love conversing with you. Chat with us in Your Conversation Pit by sending a text message! There comes a time in every entrepreneur’s life that feels like a make or break it moment. There’s been a long-standing trend centered around “burning it down” in reference to business and business models that are no longer working for the business owners that created them. Once upon a time I actually did burn it down… slowly. One match at a time. In 2021, I was a charred wreck, having poured m...
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1 year ago
57 minutes

Your Conversation Pit
Ep 18 - Visibility Strategies for the Versatile Entrepreneur
We love conversing with you. Chat with us in Your Conversation Pit by sending a text message! From a girlie that’s constantly refining the way to share with you that I run a business consulting company on + offline, am starting a short-term rental business that exists on the same pillars as The Cheetah Company does (curiosity, exploration, and connection), and am a speaker and writer for more than just business (life-advising, healing, and the human experience). In today’s episode, we’r...
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1 year ago
52 minutes

Your Conversation Pit
Ep 17 - Getting Personal: How I'm Harmonizing and Balancing Current Businesses, New Businesses, and Real Estate
We love conversing with you. Chat with us in Your Conversation Pit by sending a text message! In today’s episode of Your Conversation Pit, Ashleigh Henry is exposing the inner workings of running several businesses alongside her husband. New startups, sustaining a current business, and all of the in-betweens. We’re exploring… 🎙️Where I’ve dropped the ball, had to apologize, and had to figure my ish out quick while building new ventures, acting as a general contractor to coordinate every inc...
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1 year ago
53 minutes

Your Conversation Pit
Ep 16 - The Art of Sales Psychology Starts with This
We love conversing with you. Chat with us in Your Conversation Pit by sending a text message! In today’s episode of Your Conversation Pit we are taking a closer look into sales psychology and its role in business. Specifically, we are exploring potential reasons you could be attracting a different audience than desired, why connection is essential to prioritize, and how to speak your ideal client’s love language. Key highlights include: The social playground and why you might be a...
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1 year ago
41 minutes

Your Conversation Pit
Ep 15 - Mastering Sales Psychology in 2024 and Beyond
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 close and personal with sales psychology in 2024 and beyond. We learn the importance of buyer types, buyer love languages, building trust, and key components in creating a timeless sales strategy. Key highlights include: The 4 common buyer types translated as buyer lover languagesThe link between speed and trust to increase sales3 k...
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1 year ago
55 minutes

Your Conversation Pit
Ep 14 - Clara Bow, Taylor Swift, & Becoming a Legend of Your Industry
We love conversing with you. Chat with us in Your Conversation Pit by sending a text message! In this eye-opening episode of Your Conversation Pit, we dive deep into the insightful landscape of Taylor Swift’s ability to spark all of our interest to learn more about the iconic actress known as Clara Bow. Personal branding for business owners is the most crucial it’s ever been—it's the compass guiding your reputation, trustworthiness, and success in the market and we all know that Taylor Swift ...
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1 year ago
53 minutes

Your Conversation Pit
Ep 13 - Marketing Strategies That Are Working in 2024 & The Current State of Online Businesses
We love conversing with you. Chat with us in Your Conversation Pit by sending a text message! In this transformative episode of Your Conversation Pit, we dive deep into the ever-evolving landscape of business, online entrepreneurship in the online business space, and world-wide market trends as we've observed them unfolding since early 2023. Our community and clients have been experiencing significant shifts in their industries, sales patterns, and client behaviors—shifts that have left many ...
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1 year ago
1 hour 4 minutes

Your Conversation Pit
Ep 12 - 10 Signs that You're Evolving & Expanding in Your Life and Business
We love conversing with you. Chat with us in Your Conversation Pit by sending a text message! In this transformative episode of Your Conversation Pit, we delve into the heart of what it means to be a female founder navigating the complexities of growth, both personally and professionally. Unleashing energetic shifts and embracing lifestyle design for female founders is our goal. Our conversation is tailored for women leaders who are feeling the burnout of continuous hard work and are seeking ...
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1 year ago
52 minutes

Your Conversation Pit
Ep 11 - Where to Invest in Your Business When You're Several Years In
We love conversing with you. Chat with us in Your Conversation Pit by sending a text message! In today’s episode, we’re talking about where to invest in your business when you’re several years in. Prepare for a perspective shift to consider what to do next as a service provider, consultant, coach, agency owner, or product business owner with a diversified portfolio when you’ve been in business for a few years and things are going well. There is so much content in the world for the begin...
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1 year ago
37 minutes

Your Conversation Pit
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...