When Everything Falls Apart, Build Something Better with Shashank Shekhar | #27

The Exit Every Founder Fears with Elizabeth Ledoux | #29

What happens when the business you built becomes your identity? In this episode, Jeff Munn sits down with Elizabeth Ledoux, founder and CEO of The Transition Strategists, to unpack the emotional, financial, and deeply personal realities of succession planning for entrepreneurs and family businesses. From leaving her career as a petroleum engineer to helping founders navigate life after leadership, Elizabeth shares hard-earned wisdom on what it really takes to let go without losing yourself. They explore why most business transitions fail, how founders unknowingly hold companies back, and why the next generation often struggles under the weight of expectations. Elizabeth also shares her own transition story and how she found the successor to carry her life's work forward. In this episode: * Why founders struggle to let go of control * The difference between building a business and sustaining one * How family dynamics shape succession decisions * Why clarity about your "next chapter" matters more than money * The hidden emotional cost of leaving the business If you're building something meaningful, this conversation might change how you think about legacy, leadership, and what comes next. Follow Jeff Munn and The Pick Now Podcast for more conversations with entrepreneurs, leaders, and visionaries navigating the biggest decisions of their lives.

Why Employees Stop Caring with Barry Wolfe | #28

What happens when loyalty disappears from the workplace and nobody knows what success actually looks like anymore? In this episode of The Pick Now Podcast, Jeff Munn sits down with Barry Wolfe, President and CEO of Argos HR Solutions and author of It's All in Your Head, for a fascinating conversation about leadership, employee engagement, and why modern workplace systems are failing both managers and employees. Barry shares his journey from working in his father's manufacturing business at 14 years old, to touring as a musician, to building a consulting company focused on helping organizations rethink how they define success. Together, Jeff and Barry unpack why traditional performance reviews, personality tests, and corporate leadership programs often miss the mark and what leaders should focus on instead. In this episode, you'll learn: * Why most employees do not actually know what success looks like at work * The hidden damage caused by transactional leadership cultures * How "value-centric leadership" changes the way organizations grow people * Why personality testing and workplace assessments may be doing more harm than good * The one question every new employee wants answered immediately If you've ever questioned corporate culture, struggled with leadership, or wondered why talented people disengage, this conversation will challenge the way you think about work and management. Connect with Jeff Munn and tune into more conversations on The Pick Now Podcast.

When Everything Falls Apart, Build Something Better with Shashank Shekhar | #27

What happens when you lose your job in a new country with no money, no network, and no backup plan? On this episode of The Pick Now Podcast, Jeff Munn sits down with entrepreneur and author Shashank Shekhar to unpack the remarkable journey from immigrant startup employee to award-winning FinTech founder. After his company collapsed during the 2008 mortgage crisis, Shashank turned uncertainty into opportunity by building a mortgage business centered around education, trust, and technology. What started as late-night blog posts eventually became Instamortgage, one of the fastest-growing mortgage companies in America. Along the way, he taught himself AI, built one of the first AI-powered digital humans in the mortgage industry, and even outpaced Zoom on Deloitte's FastTech rankings during the pandemic. In this conversation, you'll hear: * How resilience beats talent without persistence * Why education became his ultimate business strategy * What founders can learn about AI right now * How to think long-term when building a company * Why limiting beliefs stop more dreams than lack of skill If you've ever wondered whether your big idea is worth pursuing, this episode might be the push you need to start.

From Rock Bottom to $400M Exit with Mike Fata | #26

He went from 320 pounds and rock bottom to building and selling a $400 million company. In this episode, Mike Fata shares how a personal health crisis led him to discover hemp, build Manitoba Harvest from scratch, and navigate two decades of uncertainty, setbacks, and breakthrough growth. From dropping out of high school to becoming a $100M+ CEO, Mike breaks down the mindset shifts that fueled his success and the identity changes required to sustain it. You'll also hear what happened after the exit, including the unexpected personal challenges that forced him to rebuild his life from the ground up and redefine success on his own terms. Key takeaways: * Why "just one more day" is the most powerful entrepreneurial mindset * The difference between being your best self vs trying to be better * How discipline, not motivation, drives long-term success If you've ever felt stuck, overwhelmed, or on the edge of quitting, this conversation will challenge how you think about growth, resilience, and what it really takes to win.

Get Your Financial House in Order with Elke Rubach | #25

What if one hard conversation today could save your family years of chaos tomorrow? In this powerful episode of The Pick Now Podcast, Jeff Munn sits down with founder Elke Rubach to unpack how childhood loss, legal training, entrepreneurship, and personal reinvention shaped her mission to normalize money conversations. From wills and wealth planning to identity, trust, burnout, and family values, Elke reveals why financial planning is about far more than money. It is about protecting the people you love most. In this episode: * Why avoiding money conversations can create generational chaos * How founders and families can build real security through intentional planning * The hidden link between values, trust, burnout, and long-term wealth Your legacy will exist whether you plan for it or not. This episode will inspire you to take control before life does it for you.