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

Fear Doesn't Make Anybody Better With Brittany Greenfield | #35

What if the thing keeping you from your next level is not lack of skill, but the fear of getting it wrong? In this episode of The Pick Now Podcast, Jeff Munn sits down with Brittany Greenfield, founder of Wabbi and host of the Good Enough podcast, for a conversation about entrepreneurship, leadership, founder pressure, perfectionism, and learning to move before everything feels certain. Brittany shares how she moved from building companies inside larger organizations to founding her own software security company. She talks about the importance of doing the uncomfortable founder work early, including making the calls, hearing customer feedback directly, and learning the value of the product before handing that work off to a sales team. Together, Jeff and Brittany explore why successful leaders often forget that they are already good enough. As responsibility grows, so does the pressure to make every decision perfectly. But that pressure can lead to overthinking, paralysis, and fear-based leadership. This conversation is a reminder that growth does not come from endless analysis. It comes from putting something into the world, learning from the response, and separating your self-worth from the outcome. In this episode: * Why founders need to hear customer feedback themselves * How early uncomfortable calls shape the value of a company * Why leaders forget they are already good enough * How success can create more pressure and perfectionism * Why doing something beats analyzing forever * How to separate challenge from self-worth * Why fear does not make anybody better If you have ever felt the weight of needing to get every decision right, this episode will help you loosen the grip, take the next step, and remember that progress comes from movement, not perfection. Connect with Jeff Munn and tune into more conversations on The Pick Now Podcast.

When Does Work Become Optional? with Phil Palumbo | #34

What if retirement isn't the goal at all? In this episode of The Pick Now Podcast, Jeff Munn sits down with wealth advisor, entrepreneur, and author Phil Palumbo, founder of Palumbo Wealth Management and author of Live Well and Never Worry About Money Again, for a conversation about financial freedom, entrepreneurship, purpose, and building a life that gives you more choices. Phil shares his journey from a blue-collar upbringing to building a successful wealth management firm, helping business owners navigate exits, and guiding people through one of the biggest transitions of their lives: figuring out who they are after work is no longer a necessity. Together, Jeff and Phil explore why so many successful people struggle after selling a business, how financial independence creates freedom without requiring retirement, and why true wealth is about having options rather than simply accumulating more money. In this episode: * Why retirement may be the wrong goal for high achievers * The difference between financial freedom and financial security * How entrepreneurs can prepare for life after an exit * Why many business owners struggle with identity after selling their company * What it means to make work optional instead of retiring * The role purpose plays in long-term happiness and fulfillment * Why taking time between chapters can lead to better decisions * How to think differently about money, lifestyle, and freedom * The importance of balancing business, family, and health * Why successful people need space to think about what they truly want If you've ever wondered what financial freedom actually looks like, struggled to balance achievement with fulfillment, or questioned what comes next after reaching a major milestone, this episode will challenge the way you think about work, money, and success. Connect with Jeff Munn and tune into more conversations on The Pick Now Podcast.

The Cost of Control with Karthik Ganesh | #33

What if the thing creating the most stress in your life is the belief that you're supposed to control it? In this episode of The Pick Now Podcast, Jeff Munn sits down with Karthik Ganesh, CEO of OnMed, for a conversation about leadership, purpose, resilience, freedom, and what it means to let go of the outcomes you can't control. Karthik shares his journey through healthcare leadership, entrepreneurship, personal loss, and spiritual growth. Together, Jeff and Karthik explore why so many people stay trapped by fear, how attachment to results creates suffering, and why the most effective leaders learn to focus on the process rather than obsess over the outcome. They discuss the power of simplicity, the importance of making decisions quickly, how to overcome self-imposed limitations, and why some of life's most difficult experiences can become our greatest teachers. In this episode: * Why focusing on the process matters more than controlling outcomes * How attachment creates unnecessary stress and suffering * The leadership lessons hidden inside personal loss * Why great leaders communicate with vulnerability and humility * How our minds become our own biggest limitations * The surprising freedom that comes from owning less * Why making decisions quickly can accelerate growth * How to recognize and break free from self-imposed shackles * The role spirituality plays in leadership and personal development * Why resilience starts with acceptance instead of resistance If you've ever felt stuck, overwhelmed by uncertainty, or trapped by the pressure to have everything figured out, this episode will challenge the way you think about success, control, and personal freedom. Connect with Jeff Munn and tune into more conversations on The Pick Now Podcast.

The Hidden Psychology of Power with Jonny Staker | #32

What if the biggest factor influencing your success isn't your skills, experience, or strategy—but the invisible dynamics shaping every conversation you have? In this episode of The Pick Now Podcast, Jeff Munn sits down with entrepreneur, investor, and author Jonny Staker, founder of Vanquish Consulting Group and co-author of The Frame: The Unspoken Laws of Power, Status, and Influence, for a conversation about leadership, negotiation, confidence, resilience, and the hidden forces that influence how we show up in business and life. Jonny shares his unconventional path from leaving school at 15, building and selling successful companies, losing everything almost overnight, and rebuilding from the ground up. Together, Jeff and Jonny explore why certainty creates trust, how people unknowingly give away power in conversations, and why some of the most successful entrepreneurs simply refuse to quit when things get difficult. In this episode: * Why the stories we tell ourselves shape our confidence and decision-making * How power, status, and influence quietly affect every conversation * Why certainty matters more than tactics in leadership and sales * How to recognize needy behavior and communicate from a position of strength * The hidden negotiation lessons most people never learn * What Jonny learned after losing everything and starting over * Why resilience is often the greatest predictor of long-term success * How identity influences results in business and life * Why successful entrepreneurs think differently about failure * The mindset shift that helps people stop seeking validation and start leading If you've ever struggled with confidence, difficult decisions, leadership, sales, or recovering from setbacks, this episode will challenge the way you think about influence, success, and personal growth. Connect with Jeff Munn and tune into more conversations on The Pick Now Podcast.

The Conversations That Shape Us with Chuck Wisner | #31

What if the biggest thing holding you back in leadership is not what you say, but the hidden story behind why you say it? In this episode of The Pick Now Podcast, Jeff Munn sits down with Chuck Wisner, founder of Wisner Consulting and author of The Art of Conscious Conversations, for a thoughtful conversation about leadership, communication, creativity, and the patterns that shape how we show up in life and work. Chuck shares his journey from music to architecture to leadership consulting, and how each chapter taught him something deeper about creativity, language, and human connection. Together, Jeff and Chuck explore why so many leaders get trapped in needing to have the answer, how our old stories can quietly limit us, and why better conversations begin with more self-awareness. In this episode: * Why the stories we tell ourselves shape how we lead and communicate * How to recognize patterns that no longer serve you * Why great leaders shift from being "knowers" to being learners * The difference between closed-fist and open-hand communication * How storytelling, collaboration, creativity, and commitment conversations build on each other * Why slowing down before making decisions can lead to better outcomes If you've ever felt stuck in old patterns, struggled to speak honestly, or wondered how to create better conversations at work and in life, this episode will challenge the way you think about communication, leadership, and personal growth. Connect with Jeff Munn and tune into more conversations on The Pick Now Podcast.