The Pick Now Podcast with Jeff Munn

What happens when the career you thought was "up and to the right" suddenly isn't? In this episode, Jeff sits down with Chris Michalak, Executive Chairman of Personify and former CEO of multiple organizations, to unpack the real decisions behind a nonlinear leadership journey.  They dig into the moment many leaders avoid talking about: failure at the top. Chris walks through what it felt like to l...

What happens when you "win" the corporate game but still feel stuck? On today's episode of The Pick Now Podcast with Jeff Munn, Eric Togneri shares how he spent 15 years climbing the ladder only to realize he was building someone else's dream. From promotions and prestige to walking away and starting over, Eric breaks down the mindset shift that changed everything. He also reveals how nearly losin...

What if the way you open every conversation is costing you the deal? In this episode, Jeff Munn sits down with Jake Stahl, sales trainer, entrepreneur, and author of Own the Room, to break down why most sales conversations fail before they even begin. From rebuilding his life after addiction to becoming a top-performing sales trainer, Jake shares how mastering communication and presence transforme...

This week, Jeff sits down with former Major League Baseball pitcher Jacob Turner to explore the difficult decisions that shape both athletes and entrepreneurs. Jacob's career took him from being drafted straight out of high school to pitching in the majors at just 20 years old. But like many professional athletes, his journey was filled with uncertainty, failure, and the constant pressure of knowi...

Entrepreneurs rarely start with perfect information. More often, the journey begins with a frustrating problem, a gut instinct, and a decision to move anyway. In this episode, Jeff talks with Steve Neeleman, founder of HealthEquity, about the moment that exposed how powerless healthcare consumers really were and how it led him to build a company focused on putting control back in their hands.  Thi...

What happens when the identity that's defined you your entire life disappears? This week, Jeff sits down with spiritual entrepreneur Kyle Jason Leitzke to explore the hidden cost of achievement and what comes after the grind.  They talk about grief, identity collapse, people-pleasing, burnout, and the moment when you realize: no one is coming to lay you off from the life you've built. If something...

What if the side project you start at night becomes the platform that reshapes an entire industry? On this episode of The Pick Now Podcast, Jeff Munn sits down with Scott Becker, partner at McGuireWoods and founder of Becker's Healthcare, to unpack the entrepreneurial journey he built alongside a demanding legal career. From launching a niche healthcare newsletter to scaling conferences, podcasts,...

In this episode, Jeff sits down with four-time entrepreneur Manny Menendez to talk about the choices that shape a career and the moments when you have to leap without perfect information.   Manny's path moves from the structure of large consulting firms to the chaos of early-stage startups. Along the way, he learned what changes when the infrastructure disappears, how to listen your way to product...

In this episode, Jeff sits down with Ronald Diamond, founder and chairman of Diamond Wealth, to unpack the pivotal choices that shaped his journey from the fall of Drexel to building a $250 million hedge fund and a syndicate of over 100 family offices.   Ronald opens up about the tough decision to sell at the top, why most family offices fail, and why being a successful entrepreneur is more about...

This week, Jeff sits down with Marc Cabrera to unpack a career journey that spans Wall Street, burnout, entrepreneurship, and ultimately, a more intentional way of living and working. They explore the hidden tradeoffs of traditional success, the generational shift in how people think about careers, and why many high achievers feel stuck even after they've "made it."  This conversation is about mor...

What started as a one-way ticket to Oaxaca turned into a global business built on trust, curiosity, and human connection.   This week, Jeff sits down with Zach Smith, founder of Anywhere, to unpack how a passion for immersive travel evolved into a purpose-driven company operating across more than 25 countries.   Jeff and Zach explore what it really means to build something slowly and intentionally...

Ashok Subramanian shares the real story behind leaving McKinsey, building Liazon from nothing, nearly running out of payroll multiple times, and ultimately selling the company in a lightning-fast acquisition that changed everything. Along the way, he reveals how founders misjudge risk, why most "great ideas" are actually wrong, and what it really takes to build something that lasts inside a broken...

What if the biggest thing holding your business back… is you? This week, Jeff sits down with Michael Pickel for a candid coaching conversation about leadership, control, and learning to get out of your own way. Michael reflects on overthinking decisions, being too hard on himself, and how unintentionally holding on too tightly can limit a team's growth. Together, they unpack the difference between...

What if the only thing standing between you and the opportunity of a lifetime is the belief that you belong there? Norm Volsky shares how a career in recruiting turned into an entrepreneurial engine—helping scale category-defining healthcare companies like Livongo and Hinge Health, and eventually launching his own investment platform. Along the way, Norm reveals how conviction, timing, and relentl...

What if the biggest career risk isn't starting a company—but never betting on yourself? Matt Kuta shares why most people wildly overestimate the danger of entrepreneurship while ignoring the hidden instability of corporate life. Drawing from his journey as a fighter pilot, private equity investor, and founder who took a defense and space company public, Matt reframes risk, failure, and what it rea...

In this episode, Jeff sits down with someone who's been in the trenches, taken big swings, gotten knocked flat, and gotten back up again — Mo Bunnell, founder and CEO of Bunnell Idea Group and bestselling author of The Snowball System and Give to Grow. Mo's story isn't a straight line. It's a series of pivots, experiments, wrong turns, bold moves, and moments when he had to trust himself enough to...

This week, Jeff talks with Eric Elwer, founder of Stepping Stone, about what happens when the feeling of being unsettled becomes impossible to ignore. Eric shares how a dark season, a moment of unexpected clarity, and a simple notebook sketch led him from a successful corporate career into the uncertainty—and purpose—of entrepreneurship.   He opens up about rebuilding a product from scratch, learn...

What if the biggest win in your career comes from saying no? In this episode, Jeff sits down with entrepreneur and investor Michael McAllister — founder of The CE Shop, a bootstrapped startup that grew into a national leader in professional licensing education and ultimately exited in a nine-figure private equity recap. Michael shares how he went from selling dictation equipment door-to-door to sc...

Some leaders chase success. Others build it quietly, brick by brick, through discipline, pain, curiosity, and an unwillingness to settle. In this episode, Jeff sits down with serial entrepreneur and explorer Hans Kaspersetz, whose life has been shaped by adversity, near-death cave dives, 14 failed startups, and a belief that the universe doesn't bring us this far just to let us fall. Hans reveals...

What if the freedom you've been chasing has been within you all along? In this solo episode, host Jeff Munn explores why so many founders and entrepreneurs sacrifice their well-being in pursuit of "freedom" — and how that very pursuit keeps them trapped. Drawing from personal experience and years of coaching high-performing leaders, Jeff breaks down the difference between freedom from (escaping fe...

Welcome to Pick Now, a space for founders, leaders, and creators who are ready to stop waiting for the right time. Every great journey begins with one decision. For Jeff Munn, that decision was to stop chasing what looked right and start choosing what felt true. This episode sets the stage for what's to come: honest conversations about the moments that define us and the choices that move us forwar...