Ten Thousand Miles

Success Isn't Enough! | Dave Guttman

June 29, 2026·1h 12m
Episode Description from the Publisher

Learn entrepreneur mentorship strategies from Dave Gutman. Discover practical business advice and founder lessons for your next venture. This episode sits down with Dave Gutman, a seasoned founder, speaker, and startup investor. We discuss his approach to building businesses and the core principles that guide his professional journey. Whether you are scaling a company or just starting out, his insights on entrepreneurship tips provide a clear roadmap for navigating common industry challenges. Throughout our conversation, Dave breaks down the realities of being a founder in today's market. He shares honest perspectives on mentorship and investment that helped shape his career. This discussion is designed for anyone looking to refine their business strategy and understand the mindset required for long-term growth. Chapters: 00:00 – Welcome to Ten Thousand Miles with Dave Guttman 01:20 – Early Life, Wrestling, Entrepreneurship, and Lessons from Failure 07:39 – Learning Business Through Search Funds, Mentors, and Acquisitions 20:29 – Defining Moments, Dyslexia, Brown, Wharton, and Life’s Turning Points 28:17 – The Cancer Misdiagnosis That Changed Everything 39:32 – Fundraising, Building Sellable Companies, and the Anti-MBA Philosophy 59:20 – AI, Lifelong Learning, Success, Leadership, and Final Lessons Subscribe for stories and business breakdowns, and comment below with which specific entrepreneurship topic you want us to cover next. Please Comment, Like, Share, and Subscribe!

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