Episode 21: Building Businesses, Masterminds, and Meaningful Conversations with Jocelyn Greenky Something shifted in this conversation almost immediately. What started as a business interview quickly turned into a masterclass on relationships, resilience, and how real success is built over decades, not months. Save to Zero co-hosts Mike and Zach sit down with entrepreneur, educator, and family business coach Joceyln Greenky to talk about everything from masterminds and AI disruption to communication styles, relationship capital, and knowing when to stay focused versus chasing the next shiny object. Jocelyn shares how growing up around a Mennonite farm shaped her work ethic, why she went back to school in her 50s, and what she’s learned from more than four decades in business. This episode dives into entrepreneurship, family business dynamics, emotional intelligence, and why the strongest business advantage might actually be your ability to connect with people. From corporate leadership to teaching students, building businesses, and advising family-run companies, this conversation is packed with practical wisdom and honest insight. You’ll Learn in This Episode: What a “Family Business Whisperer” actually does The difference between macro and micro thinking Why relationship capital matters in business How AI may reshape family business The value of small group masterminds Why emotional intelligence matters at work What makes family businesses complicated How to tell a great idea from a distraction Why being “all-in” changes everything Quotes “Relationship capital is everything. You never know which conversation is going to change your life.” “With AI and the displacement of so many crucial jobs, I think we’re going to see more family businesses emerge.” “Interesting ideas come when your back is against the wall, and you’re faced with what to do.” “You’re not alone in business. The problems you’re facing? Someone else has already faced them, too.” About Joceyln Greenky Jocelyn Greenky, MBA, is a no-nonsense business fixer, keynote speaker, and author with 40+ years of experience transforming companies and business reputations. From Fortune 500 giants to family-run firms, she’s helped leaders cut through chaos, build credibility, and drive real results with an all-in mentality. She’s the author of The Big Sister’s Guide to the World of Work (Simon & Schuster) and a trusted expert featured on CNBC, CNN, and in The New York Times and Forbes. Jocelyn has held C-suite roles across media, tech, and lifestyle brands—ELLE, Rolling Stone, Car and Driver, Men’s Journal, HBO, Material Bank—and served as an adjunct professor at Mercy University and Queen’s College. Grounded, funny, and fearless, Jocelyn brings clarity to complexity—and a serious edge to leadership. She lives in Greenwich, CT, with her husband, three dogs, and a never-empty dinner table full of family. Find Jocelyn Greenky on her Website Find Jocelyn Greenky on LinkedIn and Instagram info@siderroad.com Find REI Capital Guys For Investors & the Fund – Learn how the Fund works and book a call For Borrowers & Deals – Get funding and support for your next investment