Entrepreneurship isn’t simply about building a successful company. It affects your family, your health, your relationships, and almost every decision you make. For Josh Bowling, nearly three decades of entrepreneurship have taught him that building the right life is just as important as building the right business. In this episode of A Founder’s Life, Leo Gestetner sits down with Josh Bowling, founder of The Eve Group, to discuss entrepreneurship, founder mindset, business leadership, family, health, risk, and what it really takes to navigate the entrepreneurial life. Josh’s introduction to entrepreneurship began in childhood. Raised by a single mother who worked two jobs, he also had the opportunity to learn from successful entrepreneurs around him. One mentor in particular, Glenn Weaver, started laying pipe for a fire sprinkler company with an eighth-grade education, eventually bought the company, grew it into one of the largest in the country, and successfully sold it, all while remaining grounded and committed to his family. That example stayed with Josh throughout his career. After starting his professional journey at Arthur Andersen, Josh left to launch his first company shortly before the Enron scandal ultimately brought down the global accounting firm. Watching one of the world’s most respected professional services organizations disappear completely changed his definition of risk. Rather than viewing entrepreneurship as the risky option, Josh realized that relying entirely on an employer could carry risks of its own. From that point forward, he became increasingly comfortable betting on himself. His entrepreneurial journey has since taken him through construction, healthcare, advisory services, coworking, music, technology, fintech, and numerous founder-led businesses. Today, through The Eve Group, Josh works alongside CEOs and founders to develop growth strategies, identify potential challenges, create execution plans, and build capital strategies. But this conversation goes far beyond business. Josh opens up about one of the most difficult periods of his career, a business turnaround that nearly destroyed his family life. He even went into the office on the day his first son was born, something he now looks back on as a pivotal lesson. That experience taught him that saying family is important isn’t enough. Your calendar, career decisions, clients, and priorities have to reflect it. Over the years, Josh intentionally chose lifestyle over maximizing income so he could coach his children, attend important moments in their lives, and build the type of family life he wanted. The same intentionality now shapes his approach to founder health. After years of inconsistent exercise, fluctuating weight, and mounting stress, Josh developed a long-term approach built around mindfulness, meditation, movement, nutrition, sleep, and consistent routines. In this episode you’ll learn: Why entrepreneurship completely changed Josh’s definition of riskWhy betting on yourself can sometimes feel safer than traditional employmentHow founders can prioritize family through their actual decisionsWhy Josh chose lifestyle over maximizing incomeHow mindfulness and meditation support founder healthWhy entrepreneurs should think of themselves as executive athletesHow intentional routines create greater stability and resilienceWhy life balance changes depending on the season you’re inHow accountability helps turn intentions into actionWhy surrounding yourself with other entrepreneurs mattersJosh also explains why entrepreneurial families need community. The challenges of entrepreneurship don’t stop when the workday ends. They affect dinners, weekends, family decisions, finances, and relationships. Having people around you who understand those realities creates a support system that can be incredibly difficult to find elsewhere. For Josh, entrepreneurship isn’t the perfectly polished journey often portrayed from the outside. Things will go wrong. Priorities will shift. Some seasons will be harder than others. The key is surrounding yourself with people who understand the journey while remaining intentional about the life you’re trying to build. If you enjoy conversations about entrepreneurship, founder mindset, business leadership, founder health, work life balance, personal development, resilience, family, and building meaningful businesses, you’ll enjoy this episode. This episode of A Founder’s Life is brought to you by Thankz, helping founders scale with reliable remote talent. Email founders@thankz.com with the subject A Founder’s Life for preferred pricing. Connect with Today’s Guest – Josh Bowling Website: evegroupconsult.com LinkedIn: https://www.linkedin.com/in/jsbowling/ If you enjoyed this conversation, subscribe for more interviews with founders, CEOs, entrepreneurs, and business leaders sharing the real stories behind building meaningful businesses, and meaningful lives. LinkedIn linkedin.com/in/leogestetner Website leogestetner.com/leo Subscribe Now! youtube.com/@afounderslife?sub_confirmation=1
