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Leaders Across America With Steve AcornAuthor: Young Entrepreneurs Across America
Welcome To The Leaders Across America Podcast. This show is dedicated to young driven individuals who truly want to choose a path of their life, step out of their comfort zone and create a better future for themselves and in the end, control their own destiny. Each week, we will be interviewing a graduate from our program. You will hear some amazing stories of how being part of the Young Entrepreneurs Program helped transformed them into who they are today. You can determine if you want to be like these individuals and you will understand what it will take to get there. Learn more: https://www.yeaainternship.com/ Language: en Genres: Business, Entrepreneurship, Management Contact email: Get it Feed URL: Get it iTunes ID: Get it |
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138 | Sean Gregory - How Radical Ownership Built Leaders for Life
Wednesday, 17 June, 2026
What would you give to hear the untold truth from one of the very first student entrepreneurs who helped build a movement? In this exclusive, raw conversation, Steve Acorn sits down with Sean Gregory, an original Student Painter from 1987, to uncover the gritty, hilarious, and brutally honest stories that shaped the YEAA legacy. Together, they revisit sleepless launches, wild leaps of faith, and the make-or-break lessons still echoed across today's leadership ranks. This is not a highlight reel. It's the real story behind 40 years of "work hard, play hard" success and the relentless mindset that separates doers from dreamers. Miss this episode, and you risk overlooking the patterns that breed lasting leaders. Listen now for first-hand insights you won't find anywhere else, straight from the roots of YEAA and the heart of entrepreneurship. Timestamped Highlights 00:30 – The wildest leap of faith in Student Painters history 02:55 – Why entrepreneurship still isn't taught in college (and how Sean hacked the system) 06:18 – The tools, grit, and chaos behind launching a business in '87 10:16 – "I've never felt so alive." The real rewards of radical ownership 13:43 – The eye-opening mistakes that nearly killed his profits 16:04 – Campfires, banquets, lifelong friends: The bonds that outlast the business 22:23 – The moment Sean realized he could out-earn his first 'real' job 35:08 – Brutally honest advice for every new leader in the arena right now About the Guest Sean Gregory is a 30+ year veteran in residential real estate, executive producer of the Heart of Influence podcast, and one of YEAA's original Student Painters from 1987. With decades of sales, coaching, and entrepreneurial experience, he brings unmatched perspective on leadership and the long game of transformation. 🔗 LinkedIn Resources & Links Mentioned Heart of Influence podcast Unblinded with Sean Callagy Sherwin-Williams GMC Gaucho Important Links Gain real-world business experience, build leadership skills, and create a foundation for future success: YEAA Website Watch our case study: Leaders Across America Find more success stories here: Our Alumni Connect with Steve: LinkedIn: Steve Acorn Instagram: @steveacornyeaa Leaders Across America is an original podcast brought to you by Steve Acorn. Production and editing by Podcast Your Brand.
