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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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What does it look like to build a business with heart over 25 years — not just success on paper, but a legacy rooted in people, purpose, and service?
In this powerful conversation, Winn Claybaugh (author, speaker, and co-founder of Paul Mitchell Schools) shares what it means to lead with generosity, stay grounded in discipline, and build a culture where kindness is non-negotiable. From mentorship to brand stewardship to showing up for your team long before you ask anything of them, Winn breaks down why sustainable entrepreneurship starts with character, not ego.
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KEY TAKEAWAYS:
🔅Lead by serving first – Make deposits into people before you expect performance. Service builds trust, trust builds influence.
🔅Create culture through behavior, not slogans – Culture is what you consistently model, not what you print on a wall.
🔅Kindness should be operational, not accidental – Build it into how you onboard, give feedback, celebrate wins, and repair mistakes.
🔅Schedule your discipline – The “unseen” habits (training, reflection, preparation) are what create longevity, not the public moments.
🔅Mentor early and often – You don’t have to be “finished” to lift others; lead from exactly where you are.
🔅Build people before you build a brand – When your team grows, your business grows with them — not the other way around.
🔅The spotlight isn’t where success is built - Longevity comes from discipline — the quiet, consistent work you do when nobody is watching.
🔅Mentorship multiplies impact - Legacy isn’t what you build — it’s who you build.
RELATED LINKS
👉Follow Winn on Instagram, Facebook, and Twitter/X
👀Check out his website - www.winnclaybaugh.com
Listen to Winn's podcast, MASTERS - www.mastersbywinnclaybaugh.com
📺YouTube channel: www.youtube.com/winnclaybaugh
📚Learn more about Paul Mitchell Schools - www.paulmitchell.edu
The Hairdresser Strong Show is all about Salon Owners, Rising Stylists, and Seasoned Stylists sharing their experiences, successes, failures, and advice to inform, educate, and empower their Fellow Hairdresser. We won’t stop until we are all: Hairdresser Strong.
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The views and opinions of our guests are theirs and important to hear. Each guest's views and opinions are their own and we aim to bring you diverse perspectives, career paths and thoughts about the craft and industry so you can become Hairdresser Strong! They do not necessarily reflect the positions of HairdresserStrong.com.
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