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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