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What do you do when you spend 8 months building something and nobody pays for it?

For Kyle, the answer was to listen more carefully to what his market was actually asking for and start over. In this honest and practical conversation, Ashley sits down with Kyle Bowen, the founder of a leadership development consulting firm, to talk about what it actually looks like to pivot your entire business model, price your services in a way that communicates real value, and keep going through the emotional roller coaster of the first few years of entrepreneurship.

Kyle spent 6 years doing HR and leadership development at Chick-fil-A where he built a 10 week leadership program from scratch, created a mentorship system for every employee on staff including 16-year-olds in the drive-thru, and watched retention improve by 20% and turnover drop by 33%. Now he helps small businesses build the leadership culture they need to actually grow.

This is the kind of conversation that does not happen enough in entrepreneurship spaces. No highlight reel. No overnight success story. Just a founder who is a year and a half in, figuring it out in real time, and willing to share what it actually looks like.

What You Will Hear in This Episode:

• Why Kyle spent 8 months building a leadership platform that nobody ended up paying for and what he learned from the experience
• How one honest conversation with a client who was leaving completely changed the direction of his entire business
• Why people enthusiastically saying yes to your idea means absolutely nothing until money actually changes hands
• The pricing mistake that almost cost Kyle clients before he even got started and how he fixed it
• What the emotional roller coaster of founder led sales feels like when you have ten people in your pipeline and none of them are moving
• How Kyle built a mentorship program at Chick-fil-A that improved retention by 20% and cut turnover by 33%
• Why getting advice from founders who are one to three years in is sometimes more important than advice from someone 20 years in who has forgotten what the hard part actually felt like
• What Kyle would tell himself on day one if he could go back

About Kyle: Kyle is the founder of Hourglass Leadership, a leadership development consulting firm that helps small business leadership teams develop the clarity, accountability, and skills they need to actually lead. With a background in HR and leadership development at Chick-fil-A, Kyle brings a practical, people-first approach to building leadership cultures that drive real business results.

Connect With Kyle: www.hourglass-leadership.com

About Ponder With Ashley: Ponder With Ashley is a business growth channel and podcast for founders, consultants, and small business owners who are building from the ground up. Every week Ashley drops Pondering Prompts to help you move your business forward, Pondering Lessons from real experience, and honest founder interviews from people who are in the fight right now. No highlight reels. No guru tactics. Just real conversations and practical lessons worth pondering.

Subscribe and Connect:

YouTube: youtube.com/@ponderwithashley

Website: ponderthisconsulting.com

LinkedIn: www.linkedin.com/in/ashley-waddington

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Have you ever considered leaving corporate America but stayed because of health insurance?

For consultants, freelancers, fractional executives, gig workers, and other self-employed professionals, figuring out healthcare can be one of the biggest barriers to leaving a traditional job.

Brian Znamirowski experienced that problem firsthand.

Brian is the founder of Fractional Healthcare, a platform created to help independent professionals find health insurance solutions outside of traditional employer-sponsored coverage. He’s also an HR consultant and former VP of HR who left corporate America in 2023 and decided to build something of his own rather than go back.

In this episode of Ponder With Ashley, Ashley Waddington and Brian talk about health insurance for consultants and self-employed professionals, leaving corporate to start a business, and the realities of building two companies from scratch.

They also get into something many new founders discover quickly: your corporate title, network, and resources don’t necessarily come with you into entrepreneurship.

In this conversation:

💭 Why health insurance can be one of the biggest barriers to becoming a consultant, fractional executive, freelancer, or business owner

💭 Brian’s experience navigating healthcare after leaving corporate America

💭 How his own frustration helped inspire Fractional Healthcare

💭 What Brian learned about sales and rejection after years of leading HR teams inside large companies

💭 Why your corporate network doesn’t always translate into clients when you become an entrepreneur

💭 What it really looks like to bootstrap a business from scratch

💭 Why Brian launched Fractional Healthcare before he even had a website

💭 Why he believes founders should spend less time conceptualizing and more time executing 💭 What the growing fractional and independent workforce could mean for the future of work and healthcare

Whether you’re considering leaving corporate, building a consulting or fractional business, already self-employed, or trying to figure out healthcare outside of a traditional employer, this conversation offers plenty to ponder.

Connect with Brian Znamirowski:

LinkedIn: www.linkedin.com/in/brianznamirowski/

HR by BZ: www.hrbybz.com

Connect with Ashley:

Ponder This Consulting: www.ponderthisconsulting.com

LinkedIn: www.linkedin.com/in/ashley-waddington

Follow Ponder With Ashley for founder interviews, Pondering Prompts, Pondering Lessons, and practical business growth ideas worth pondering. 💭

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Your charitable giving needs a strategy.

What if corporate philanthropy could support employee retention, recruitment, client relationships, and business growth while still creating meaningful impact in the community?

Emily Zimmon spent more than a decade working in the nonprofit sector before recognizing a problem on the other side of the table: many of the companies funding nonprofits were overwhelmed by their own charitable giving.

They didn’t know which opportunities to say yes or no to. There wasn’t always a strategy behind their donations. And corporate philanthropy often became someone’s “additional duties as assigned” rather than an intentional business function.

Emily saw the gap and built An Enduring Legacy, where she helps businesses develop more strategic approaches to corporate philanthropy and charitable giving.

In this episode of Ponder With Ashley, Ashley Waddington and Emily talk about corporate giving strategy, social impact, finding an underserved problem in the market, and what it really looks like to build a mission-driven business through the messy first years of entrepreneurship.

In this conversation:

💭 How Emily identified a gap in corporate philanthropy that became the foundation of her business

💭 Why she went from serving individual nonprofits to potentially impacting thousands through a different business model

💭 What surprised her about how long building a business actually takes

💭 How companies can connect charitable giving with employee retention, recruitment, and client relationships

💭 Why strategic philanthropy isn’t only for large corporations

💭 How solopreneurs and small businesses can incorporate giving into their business strategy 💭 Why talking about the good your company is doing doesn’t have to be bragging

💭 What “trust your crazy ideas” looks like when you’re in the messy middle of entrepreneurship

Whether you’re responsible for corporate philanthropy, building a social impact or charitable giving strategy, considering entrepreneurship, or navigating the first few years of building your own business, this conversation offers plenty to ponder.

Connect with Emily Zimmon: An Enduring Legacy: www.AnEnduringLegacy.com

LinkedIn: www.linkedin.com/in/emilyzimmon/

An Enduring Legacy on LinkedIn: www.linkedin.com/company/an-enduring-legacy/

Connect with Ashley: Ponder This Consulting: www.ponderthisconsulting.com

Follow Ponder With Ashley for founder interviews, Pondering Prompts, Pondering Lessons, and practical business growth ideas worth pondering. 💭

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Sales doesn’t have to give you the ick.

If sales feels like the hardest part of running your business, you’re not alone. You probably don’t need another rigid sales script or someone else’s formula. You need to find an approach to selling that actually feels like you.

Joe Hinderstein is the founder of Joe Hinderstein Healthcare Consulting, an independent sales consulting firm primarily serving the healthcare industry. His work sits at the intersection of sales strategy, revenue operations, sales leadership, automation, and data enrichment.

In three years of building his own consulting business, Joe has helped clients transform how they sell, including helping one client go from a 2% close rate to closing six deals in a single week.

In this episode of Ponder With Ashley, Ashley Waddington and Joe talk about founder-led sales, generating leads, getting ghosted by prospects, building an authentic sales process, and what happens when you let the market help shape the business you’re building.

In this conversation:

💭 How Joe went from corporate sales to a failed startup and eventually built his own sales consulting business

💭 How one free client turned into three paying clients, then ten, and eventually a full business 💭 Why prospects ghost and what founders can do differently

💭 Joe’s three service pillars: go-to-market strategy, sales coaching and training, and revenue operations

💭 How commercial strategy, automation, and data enrichment can help businesses generate leads and close deals

💭 Why Joe approaches sales as a cheerleader, detective, and consultant

💭 How he put his sales knowledge into a Claude AI project and built a tool for his clients

💭 Why an authentic sales approach can be more effective than copying someone else’s process

💭 What Joe wishes he knew when he started his entrepreneurial journey

Whether you’re a founder struggling with sales, a consultant trying to generate more leads, a fractional building a pipeline, or someone considering leaving corporate to start a business, this conversation offers a different way to think about selling.

Connect with Joe Hinderstein: Joe Hinderstein Healthcare Consulting: www.joehinderstein.com

Connect with Ashley: Ponder This Consulting: www.ponderthisconsulting.com

Follow Ponder With Ashley for founder interviews, Pondering Prompts, Pondering Lessons, and practical business growth ideas worth pondering. 💭

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How do you get your first clients when you’re starting a business or consulting practice?

Annia Mercado believes founders need to stop hiding behind their websites and start selling.

Annia is the founder of Unique Blend Consulting, where she helps early-stage founders build sales confidence, land their first clients, and create the systems they need to start generating revenue.

Before entrepreneurship, Annia worked in corporate banking and commercial credit, helping businesses with $10 million to $100 million in revenue secure funding to grow. Starting her own business taught her that understanding business and actually building one are two very different things.

In this episode of Ponder With Ashley, Ashley Waddington and Annia talk about what it really takes to get your first clients, overcome the fear of selling, and stop spending time on activities that feel productive but aren’t generating revenue.

In this conversation:

💭 Why getting your first sale should be a new founder’s priority

💭 Why founders hide behind websites, offers, and networking instead of selling

💭 How to build confidence in sales conversations

💭 The 80/20 rule of selling: 80% listening and 20% talking

💭 How Annia landed her biggest client within six months through her network

💭 Why the business you start is rarely the business you end up building

💭 What founders should consider before spending thousands on courses and programs

💭 Annia’s advice to her earlier founder self: “Get over yourself and stop working on the website.”

Whether you’re trying to get your first consulting clients, grow a service-based business, improve your sales skills, or make the leap from corporate to entrepreneurship, this conversation is packed with practical lessons from someone who has made that transition herself.

Connect with Annia Mercado:

Unique Blend Consulting: www.uniqueblendconsulting.com

Instagram: @uniqueblendconsulting

LinkedIn: Annia Gutierrez Mercado

Connect with Ashley:

Ponder This Consulting: www.ponderthisconsulting.com

Instagram: @ponderthisconsulting

LinkedIn: Ashley Waddington

Follow Ponder With Ashley for weekly founder interviews, Pondering Prompts, Pondering Lessons, and practical business growth ideas worth pondering. 💭

Hey! I'd love to hear your thoughts, send me a voice note.

Welcome to Ponder With Ashley, a podcast dedicated to helping entrepreneurs, founders, consultants, and business owners grow their businesses through practical strategies, authentic leadership, and real-world lessons.

In this introduction, Ashley Waddington, founder of Ponder This Consulting, shares her journey of building a consulting business from the ground up after being laid off. Starting with no referrals, no large network, and no shortcuts, she learned firsthand what it takes to grow a business through persistence, sales, marketing, content creation, operations, and continuous learning.

On this podcast you'll find:

✅ Business growth strategies

✅ Entrepreneurship lessons and founder stories

✅ Sales and marketing insights

✅ Content marketing and personal brand building

✅ Business systems and operations tips

✅ AI and technology for entrepreneurs

✅ Leadership and mindset discussions

✅ Interviews with successful founders and business owners

Whether you're starting a business, growing a consulting practice, scaling a service-based business, or looking for fresh ideas to move your company forward, this podcast is designed to help you think differently and uncover new opportunities.

If you're tired of cookie-cutter business advice and want honest conversations about what entrepreneurship really looks like, you're in the right place. Subscribe/follow for weekly business growth content, founder interviews, marketing insights, and practical ideas worth pondering. 💭