The Pick Now Podcast with Jeff Munn

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.   

What if the biggest breakthrough in your career comes from following a person, not a plan? In this episode, Jeff Munn sits down with Chris Younger, founder and CEO of Class 6 Partners, to explore a journey that began in law, wound through Silicon Valley acquisitions, and ultimately led to building a relationship-driven investment banking firm. Along the way, Chris shares lessons from extraordinary mentors, the realities of entrepreneurship, and why purpose matters more than achievement. You'll hear powerful stories about leadership during crisis, the challenge of life after selling a business, and how meaningful relationships shape both success and fulfillment. Key takeaways: • Why great mentors can accelerate decades of learning into just a few years • What entrepreneurs often underestimate about life after an exit • How service, relationships, and purpose create lasting fulfillment Whether you're building a company, leading a team, or searching for what's next, this conversation offers a thoughtful reminder that success is rarely about the transaction and almost always about the people.  

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.  

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.  

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.  

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.  

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.  

What if you're just one yes away from changing your entire life? In this episode, Jeff Munn sits down with serial entrepreneur Bryan Lord to unpack the messy, unfiltered reality of building something from nothing. From feeling out of place in college to raising capital off a 14-page deck, Bryan shares how persistence, irrational belief, and a willingness to hear "no" over and over again shaped his journey. They dive into the truth about entrepreneurship that no one talks about—the politics, getting fired from your own company, and why success doesn't always feel the way you think it will. Bryan also reveals why chasing the destination can leave you empty, and what actually matters in the long run. Key takeaways: Why being a generalist can be your greatest advantage The power of hearing "no" and still moving forward Why you're often better off raising capital with just an idea The hidden downside of "making it" If you've ever felt like you don't fit the mold, this conversation will challenge how you think about success—and what it really takes to build something meaningful.  

What if the rise of AI isn't about replacing us… but revealing who we really are? In this episode, Yen Anderson shares her journey from defense tech to becoming one of the earliest voices inside Microsoft advocating for AI adoption. From experimenting with ChatGPT on day one to influencing thousands globally, Yen explains why AI isn't just a tool. It's a turning point for human identity. Together with host Jeff Munn, they explore what happens when machines take over repetitive work and why the future belongs to those who embrace creativity, psychology, and human connection. Key takeaways: Why AI will replace tasks, not human potential The hidden danger of outsourcing your thinking How to rediscover your identity in an AI-driven world If you've ever questioned your career, your purpose, or your place in a rapidly changing world, this conversation will challenge you to rethink everything.  

What if the thing that looked like failure was actually the moment everything changed? In this episode, Jeff Munn sits down with Scott Millson to unpack a career shaped by risk, reinvention, and powerful relationships. From launching a startup during the dot-com boom to building and selling his own company, Scott shares how "failures" became the foundation for everything that followed. They dive into the mindset shifts that helped Scott move from chasing success to creating impact, and the lessons that now fuel his second chapter as an author and speaker. Key takeaways: Why failure is often just "too early," not wrong The trust equation that defines great leaders How to find mentors without ever asking for one If you're building something, questioning your next move, or redefining success, this conversation will challenge how you think about growth and what really matters.  

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 lose the job he spent decades working toward and how that experience reshaped the way he thinks about ownership, leadership, and risk. This is a conversation about unexpected paths, hard calls, and what it really means to lead when you don't control the outcome.   Connect with Chris and Personify: Website: personifyhealth.com LinkedIn: Personify Health Facebook: Personify Health Instagram: @personify_health  

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 losing it all in the 2008 crash forced him to rethink what it really means to build a business. Key takeaways: The difference between making money and creating value Why most founders unknowingly trap themselves in a "job" How to build a business that can survive without you If you've ever felt like success isn't enough, this episode will challenge how you define it and push you to think bigger.  

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 transformed both his business and his life. You'll learn how to shift from surface-level conversations to meaningful, high-impact interactions that actually convert. Key takeaways: Why "How are you?" kills connection and what to say instead The STRATA framework for influencing any conversation How to read signals, reframe objections, and close with confidence If you've ever struggled with sales, confidence, or connecting with people, this conversation will change how you show up.  

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 knowing someone else is always ready to take your place. This is a conversation about identity, risk, and why the most meaningful parts of the journey often happen long before the final outcome.   Connect with Jacob: LinkedIn: Jacob Turner Instagram: @thejacob_turner YouTube: @TheJacobTurner Website: momentprivatewealth.com

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.  This conversation explores what it really looks like to build something disruptive inside one of the most complex industries in the world and the mindset required to keep choosing forward when the outcome is far from guaranteed.   Connect with Steve: LinkedIn: Steve Neeleman Website: healthequity.com  

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 needs to change, it's on you. This episode is about trusting the nudge. About building from purpose instead of performance. About discovering that entrepreneurship — and leadership — might be one of the most spiritual journeys we can take.   Connect with Kyle: Website: kylejasonleitzke.com LinkedIn: Kyle Jason Leitzke Instagram: @kylejasonleitzke  

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, and a national media brand, Scott shares how he made pivotal decisions without perfect information and kept going when the path was unclear. Scott opens up about delegating to people smarter than him, stepping away from leadership roles he once held tightly, and redefining his identity beyond titles like department chair and CEO. Key themes in this episode: • Hiring people smarter than you and letting them thrive • Knowing when to keep going and when to pivot • Building something meaningful without waiting for perfect conditions If you are navigating growth, leadership transitions, or the early uncertainty of building something from scratch, this conversation will challenge you to ask a powerful question: What is the next right move?   Connect with Scott Becker: Website: beckershospitalreview Connect with Jeff Munn: Podcast: The Pick Now Podcast with Jeff Munn LinkedIn: jeffmunn Start small. Iterate. Keep going.  

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-market fit, and why belief, both in the mission and the team, can be the difference between a stagnant business and a breakout one.   This is a conversation about growth mindsets, scrappy beginnings, and the decisions that don't come with a clear answer. Connect with Manny: LinkedIn: Manny Menendez

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 emotional stamina than intelligence. He also shares hard-earned lessons about ego, purpose, and why money alone doesn't create a meaningful life.   If you've ever wondered when to stay the course, when to walk away, or what success really means, this conversation will give you a lot to think about. Connect with Ronald: LinkedIn: Ronald Diamond Website: familyofficeworldmedia.com

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 more than career pivots. It's about redefining success, questioning inherited scripts, and learning how to make decisions that actually support the life you want to live. Connect with Marc: LinkedIn: Marc Cabrera

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, why authenticity beats scale-for-scale's-sake, and how patience, trust, and values-based decisions have guided Zach through nearly two decades of entrepreneurship.  Connect with Zach: Website: anywhere.com LinkedIn: Zachary B. Smith  

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 healthcare system. In this episode, Jeff Munn and Ashok unpack: Why the scariest part of entrepreneurship isn't failing — it's succeeding How Liazon pivoted from a dead-end pilot into a billion-dollar acquisition What founders get wrong about exits, risk, and building inside big companies Whether you're starting your first company or scaling your fifth, this conversation will challenge how you think about risk, leadership, and what it means to truly build something. The stakes only go up — but so does what you're capable of.     Guest: Ashok Subramanian 🔗 Centivo: centivo.com Host: Jeff Munn 🎙 Pick Now Podcast 🔗 LinkedIn: jeffmunn  

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 expectations and agreements, why control and growth can't coexist, and how real leadership often means creating space—for your team and for yourself.  

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 relentless value creation compound into outsized impact. In this episode, you'll learn: Why progress isn't linear—and why that's a good thing How betting on people early can change everything The mindset shift that turns "Why me?" into momentum If you've ever felt on the edge of something bigger, this conversation might be the push you need.  

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 really means to live without regret. In this conversation, Jeff and Matt explore why clarity beats comfort, how public failure is less dangerous than people think, and why building something uncertain can actually be the safest move of all. Key takeaways include: Why staying at a "secure" company may be riskier than starting a business How entrepreneurs often have more clarity and control than corporate employees Why fear of public failure keeps talented people from ever starting If you've ever felt stuck choosing safety over purpose—or wondered what future you might regret—this episode will challenge how you think about risk, courage, and career decisions.  

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 take the next step. Jeff and Mo talk about the quiet fear that comes with stepping out on your own, the 100-day cash crisis that pushed him to rebuild from scratch, and the principles that guided him from actuarial spreadsheets to training more than 60,000 people around the world.   Connect with Mo: Website: bunnellideagroup.com LinkedIn: Mo Bunnell Books: Amazon YouTube: @MoBunnell1

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, learning to make hard decisions fast, and the role faith and intuition played in reshaping his life. What emerges is not a story about technology, but about alignment, courage, and becoming the version of yourself you didn't know existed.   If you've been waiting for the "right" moment to begin, this conversation is an invitation: Start before you're ready. The path appears when you choose it. Connect with Eric: Website: mysteppingstone.ai LinkedIn: Eric Elwer Email: [email protected]  

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 scaling a tech-enabled education platform, and the surprising moment he walked away from a massive acquisition deal because it didn't align with his values. Michael opens up about the deeper why behind his drive: growing up around scarcity, learning to innovate under pressure, and discovering that entrepreneurship is as much a spiritual journey as a strategic one. We explore: How crisis moments can force your most important innovations Why gut instinct is a business tool, not just a feeling What it takes to build (and protect) a people-first culture How to choose the right private equity partner — not just the highest bidder This conversation is a reminder that the real reward isn't just the exit — it's who you become along the way. Listen in and get inspired to bet on yourself. Connect with Michael McAllister: The CE Shop: https://www.theceshop.com Connect with Jeff Munn: LinkedIn: jeffmunn The Pick Now: jmunn.com

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 how coding before he could read led him into entrepreneurship, why meditation and fear inventories became survival tools, and how pushing limits helps him redefine purpose.    Connect with Jeff: https://linktr.ee/jeffmunn   Learn More About Hans: Website: oralucent.com Code MUNN20 for 20% off your order LinkedIn: Hans Kaspersetz About Our Guest: Hans Kaspersetz is the CEO of Oralucent, a groundbreaking oral care company pioneering the use of red and blue light therapy to improve gum health, whiten teeth, and support systemic wellness.   A seasoned entrepreneur with multiple successful exits and a track record of building a $100M enterprise, Hans has spent more than 20 years at the intersection of health technology, consumer wellness, and marketing innovation. Outside the boardroom, Hans is an avid cave explorer and ultramarathon runner, channeling the same curiosity and endurance that drive his business ventures. Hans is an early stage investor with more than a dozen companies in his portfolio and multiple advisory roles that focus on operations and scaling.   Having endured his own oral health and health challenges, Hans is passionate about the science of oral light therapy, its emerging synergistic links to the biohacking and longevity landscape, and why your mouth may be the new frontier of whole-body health.  

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 fear and inadequacy) and freedom to (creating from wholeness and awareness). Key themes: The hidden cost of chasing success and validation The illusion of "freedom" as an external reward Discovering unconditioned awareness — the ultimate inner freedom This is a must-listen for anyone ready to stop grinding for someday and start living free now.   Connect with Jeff: https://linktr.ee/jeffmunn  

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 forward. Let's get started.   Connect with Jeff: https://linktr.ee/jeffmunn