Scaling Through Recessions, AI, and Everything Else That Goes Wrong

CEO Interview - What does it really take to grow a company from $6 million to more than $100 million in revenue? Leadership... In this episode of Ten Thousand Miles, Vic Pepe sits down with Josh Gould - CEO of The Big Word, investor, and entrepreneur who has spent decades building and scaling businesses through recessions, wars, AI disruption, and private equity ownership. Josh shares the unfiltered realities of entrepreneurship: why failure is the norm, how resilience beats brilliance, and why the companies that survive aren't always the prettiest—they're the ones built like cockroaches. The conversation dives into scaling, private equity, AI, leadership, difficult decisions, and the mindset required to build businesses that can withstand almost anything. Along the way, Josh offers practical lessons on hiring, innovation, and why having fun may be one of the most underrated business strategies of all. Whether you're a founder, executive, investor, or aspiring entrepreneur, this episode is packed with hard-earned wisdom from someone who's lived every lesson he shares. In this episode: - Growing a company from $6M to $100M+ - Why most entrepreneurial decisions fail—and why that's okay - The "cockroach" philosophy for building resilient businesses - Lessons from surviving multiple waves of AI disruption - What it's really like selling to private equity - Build vs. buy: making smarter technology decisions - Hiring leaders who complement your weaknesses - Why entrepreneurship is both freedom and sacrifice - The overlooked importance of having fun while building something meaningful Chapters 00:00 Welcome to Episode 120 & Meet Josh Gould 03:26 The Mission That Has Driven Josh's Entire Career 09:42 Why Failure Is the Real Path to Entrepreneurial Success 19:14 Scaling from $6M to $100M Through Constant Reinvention 29:39 Selling to Private Equity: What Every Founder Should Know 47:00 AI, Automation, and the Future of Business 01:12:31 Lightning Round: Leadership Lessons, Hiring, and Why You Should Never Forget to Have Fun https://www.linkedin.com/in/joshuadgould?utm_source=share_via&utm_content=profile&utm_medium=member_ios https://youtube.com/@exec_craft?si=pZ-kiXjXXgsFn69r https://www.instagram.com/execcraft?igsh=YzNtbGR5bmg5OHNo https://en-us.thebigword.com/