In this episode of Pick Now, Jeff Munn talks with Kevin McDonnell, CEO coach, chairman, consultant, and health tech leader, about entrepreneurship, leadership, identity, coaching, and what it takes to scale a business without trying to do everything alone. Kevin shares that his entrepreneurial mindset started with curiosity. Early in his career, he launched several ventures that failed, but each one taught him important lessons about building, experimenting, and learning quickly. He explains that pride often keeps entrepreneurs from asking for help, even when working with someone more experienced could help them move faster and avoid mistakes. A major focus of the conversation is leadership through growth. Kevin talks about becoming CEO of a health tech company and helping it grow from no market share to 80 percent market share in its niche. His approach was not to control every decision, but to trust the team, remove obstacles, and help people do their best work. Jeff and Kevin also discuss expectations, uncomfortable conversations, and the way leaders can accidentally create problems by assuming people should know what has never been clearly said. Kevin explains that when leaders expect more from someone, they need to actually have that conversation. Later, Kevin shares how he became a CEO coach and advisor after realizing founders need someone who understands the journey, can challenge their thinking, and can provide a no consequence conversation outside the board, investors, or team.

In this episode: ● Why curiosity drives entrepreneurship ● How early failures can accelerate learning ● Why pride keeps founders from asking for help ● How CEOs can support without controlling ● Why expectations need to be clearly communicated ● Why uncomfortable conversations create clarity ● How coaching and advisory work together ● Why founders need an independent thinking partner ● How to know when to ask for help ● Why defining "enough" matters

This episode is a reminder that leadership is not about having every answer. It is about building the right team, asking for help sooner, creating clarity, and knowing what success is supposed to mean for you.

In this episode of Pick Now, Jeff Munn talks with Jim Bush, founder of Weather Shield Roofing Systems, about entrepreneurship, growth, leadership, company culture, delegation, succession, and knowing when it is time to step into a different role.

Jim shares how he started his roofing company at just 19 years old during a difficult economic period. With no truck, no ladder, and very little equipment, he began knocking on doors and figuring things out as he went. His early years were built on grit, determination, and doing whatever needed to be done to keep the business alive.

A major focus of the conversation is the transition from being the hero who does everything to building a company that can run through systems and people. Jim explains that in the beginning, founders often have to do everything themselves. But as the business grows, the same habits that helped them survive can eventually make them the bottleneck.

Jeff and Jim also talk about hiring, delegation, and knowing when to pass versus when to keep the ball. Jim explains that founders need to understand their business deeply before handing things off, but they also need to recognize when they are holding on too tightly.

The conversation also explores company culture. Jim talks about how every team can develop its own subculture, and why leaders must put values before performance. He shares the danger of keeping high performers who damage the culture and explains why the right people in the right seats matter as companies grow.

Later, Jim reflects on stepping out of the CEO role. He explains that Weather Shield needed an executive CEO for its next stage, and he had the self awareness to recognize that he was no longer the right person for that seat.

In this episode: ● How Jim started a company at 19 ● Why early entrepreneurship requires grit ● How founders become bottlenecks ● When to delegate and when to stay involved ● Why systems matter as a company grows ● How culture changes through managers ● Why values must come before performance ● What it means to fire yourself as CEO ● How succession planning creates stronger leadership

This episode is a reminder that building a company is not just about starting strong. Jeff and Jim explore how real leadership means growing, letting go, protecting the culture, and putting the needs of the company above your own pride.

In this episode of Pick Now, Jeff Munn talks with Cesar Marin about leaving a 25 year career at CNN, changing his relationship with cannabis, discovering microdosing, and becoming a bridge for people who are curious about psychedelics. Cesar shares how he spent decades working in live news and sports production at CNN. Over time, he found himself on the corporate hamster wheel, unsure of what would come next. Around the same time, he was dealing with a cannabis dependency that had become part of his daily life.

A major turning point came when mushrooms entered his life. What started as curiosity became a deeper wake up call. Cesar explains that psychedelics helped him look honestly at who he was, what he was chasing, and how he wanted to live. Through microdosing, he began to feel more present, creative, grateful, and connected.

Jeff and Cesar also talk about the importance of intention, mindset, setting, and integration. Cesar explains that the medicine itself is only one part of the experience. What happens before and after matters just as much, especially when someone wants real change instead of just another high.

The conversation also explores Cesar's layoff from CNN and how he was able to leave with peace, gratitude, and compassion. Instead of seeing the layoff as only a loss, he used it as a doorway into Cultivating Wisdom, Microdosing Over 50, and later The Summit Within.

Later, Cesar talks about helping older men and fathers reconnect with presence, vulnerability, love, and emotional honesty. He explains that many successful men have provided for their families but have not always been fully present with them.

In this episode: ● How Cesar's CNN career shaped his storytelling ● Why cannabis became a dependency ● How mushrooms changed his relationship with cannabis ● Why intention matters before any psychedelic experience ● What microdosing taught Cesar about presence ● How gratitude helped him move through being laid off ● Why Cultivating Wisdom was created ● How The Summit Within helps men reconnect with themselves ● Why presence matters more than just providing

This episode is a reminder that change often begins when someone becomes honest about what they are chasing. Jeff and Cesar explore how presence, curiosity, storytelling, integration, and emotional courage can help people move from escape into deeper connection.

In this episode of Pick Now, Jeff Munn talks with AJ Jones, founder and CEO of More, about career reinvention, health scares, authenticity, and what it means to stop postponing the life youalready know you want to live. AJ spent years in financial services, building a successful career across firms like Wells Fargo, BlackRock, and Schwab. From the outside, life looked stable. He had a career, a family, a home, and a clear path. But in 2016, everything changed when he suffered a massive Widowmaker heart attack while mountain biking with friends. After surviving, AJ began asking bigger questions. While recovering, he felt called to find his birth parents and later realized he wanted to use his story to help and inspire others. That experience eventually led him away from financial services and toward work centered on authenticity, purpose, and helping people live more honestly. Jeff and AJ talk about the tension between a good life and an authentic life. Jeff names this as the curse of good enough: when the job is fine, the money is good, and nothing is technically broken, but something inside still knows there is more. AJ explains that this does not always mean blowing up your life. It means asking what you actually want and taking intentional steps toward it.

The conversation also explores fear, risk, and small steps. Jeff points out that fear often protects the status quo, not necessarily your future. AJ reminds listeners that action creates clarity, and change does not have to happen all at once. It can start with one small bite, one honest question, and one step toward the life you want.

In this episode: ● AJ's career in financial services ● The Widowmaker heart attack that changed his life ● Why survival made him question his path ● How finding his birth family shaped his story ● Why he built More ● What the curse of good enough means ● Why reinvention does not always mean blowing up your life ● How action creates clarity ● Why fear protects the status quo ● How community helps people transform

This episode is a reminder that life can change fast. You may not need to destroy everything you have built, but you do need to be honest about what you want. The life you are called to live may already be waiting for you to stop postponing it.

https://www.bemorealigned.com

In this episode of Pick Now, Jeff Munn talks with Cabot Earle, a lawyer, founder, former CEO, and advisor who has led companies through growth, acquisitions, succession, and transition. Cabot shares how his legal background became a platform for business leadership. Early in his career, he learned to step into unclear situations, ask for help when needed, and figure out what had to be solved. That mindset carried him from legal work into operating roles, CEO leadership, acquisitions, and eventually founder life. Jeff and Cabot talk about what changes when someone moves from advisor to decision maker. Cabot explains that advising on a decision feels very different from being the person who has to sit with it, own it, and make the final call. The conversation explores succession, founder dynamics, and the pressure that comes with making decisions that affect employees, clients, relationships, and the future of a company. The episode also gets into communication as one of the most important parts of leadership. Cabot says that as a new CEO, he was focused on growth, customers, and profitability, but later realized that communication had to be deliberate. Leaders have to explain where the company is going, who is coming along, and why decisions are being made. Later, Jeff and Cabot discuss fear, ego, and delayed decisions. Cabot explains that leaders often know what needs to happen before they actually act. The delay usually comes from emotion, uncertainty, or fear of how the decision will land. Jeff connects this directly to the heart of Pick Now: leaders can plan, think, and analyze, but at some point they still have to make the call.

In this episode: ● How Cabot moved from law into leadership ● Why "figure it out" became part of his operating style ● What changes when you become the final decision maker ● Why CEO decisions are hard when they affect people ● How succession changes founder and leader dynamics ● Why communication is one of the most important CEO responsibilities ● What Cabot learned from building and buying companies ● Why leaders often delay decisions they already know they need to make ● How fear and emotion show up in business decisions ● Why outside advisors can help CEOs move sooner

This episode is a reminder that leadership is not about having every answer in advance. It is about making the best decision you can, communicating clearly, and moving forward even when you cannot fully predict what happens next.

Connect with Cabot

www.cabotearle.com

What if success is not mysterious, but the result of identity, guidance, action, consistency, and time? In this episode of Pick Now, Jeff Munn sits down with entrepreneur, bodybuilder, musician, author, public speaker, and coach Rob Stein. Rob shares how ambition and drive have shaped his journey from music teacher to full-time entrepreneur, real estate leader, bodybuilder, author, and keynote speaker. Through each chapter, he explains that success is not just about hitting metrics or making money. It starts with identity.

Rob breaks down his Impossible to Fail framework and explains why the first step is getting the right blueprint from someone who has done what you are trying to do and knows how to teach it. From there, success comes through massive action, relentless consistency, and time.

Jeff and Rob also talk about why people quit too early, why boring habits matter, and why proof of concept is what turns discipline into a habit. Rob uses examples from fitness, bodybuilding, real estate, and business to show how people can keep going before the results show up. The conversation also goes deeper into identity, self-commitment, faith, and what it takes to become the kind of person who can actually sustain the results they want.

In this episode:

• Why identity creates results
• Why success is not mysterious
• The Impossible to Fail framework
• Why every goal needs the right blueprint
• How to choose the right coach or mentor
• Why massive action still matters
• Why consistency is boring but essential
• How habits become easier after proof of concept
• Why honoring small commitments builds identity
• How faith, humility, and self-reflection shaped Rob's growth

If you are building something, chasing a goal, or wondering whether you should keep going, this episode is a reminder that success usually comes down to the right blueprint, enough action, enough consistency, and enough time.

What if the problem you keep trying to solve is not actually the real problem?

In this episode of Pick Now, Jeff Munn sits down with Amy Lessinger, entrepreneur, speaker, coach, and leadership strategist, for a conversation about fear, leadership, identity, discipline, and what it takes to build something through uncertainty.

Amy shares her journey from studying speech pathology to entering real estate, building a successful team, growing a group of brokerages through the Great Recession, and eventually becoming President of RE/MAX Worldwide. Along the way, she learned that leadership is not about title, control, or hierarchy. It is about building and elevating other people.

Amy opens up about signing a major lease right as the market began crashing, lying awake at night wondering if she had made the biggest mistake of her life, and deciding that quitting was not an option. Instead, she focused on helping agents develop the skills they needed to win in a market where everything around them was collapsing. Jeff and Amy also talk about fear, coaching, discipline, founder identity, and why leaders often become the bottleneck in their own organizations. Amy explains how fear can sound convincing, how the brain tries to keep us safe, and why transformation begins when leaders stop solving surface-level symptoms and start getting to the deeper problem underneath.

In this episode:

• Why Amy chose real estate over the traditional path
• What it feels like to work without a guaranteed paycheck
• How she built through the Great Recession
• Why fear cannot be allowed to drive your life
• How discipline creates freedom
• Why founders often become their own ceiling
• What happens when leaders are too needed by their team
• How to find the real problem underneath the obvious problem

If you are a founder, CEO, coach, entrepreneur, or leader trying to grow beyond fear and old identity, this episode will help you ask better questions and look deeper at what is really getting in the way.

Connect with Jeff Munn and tune into more conversations on Pick Now.

What if the impossible goal only looks impossible because you have not broken it down small enough yet? In this episode of Pick Now, Jeff Munn sits down with Steven, an entrepreneur, advisor, author, endurance athlete, mountain climber, and founder who built and sold a company after immigrating to the United States from Ukraine as a child. Steven shares how his immigrant upbringing shaped his entrepreneurial drive. His family came to America in pursuit of a better life, and that mindset became part of how he approached business, risk, opportunity, and personal challenge. He tells the story of founding his company in the 1990s, growing through major technology shifts, building around email migration, licensing software to IBM and Microsoft, and eventually selling the company. Along the way, he experienced what he calls multiple exits of the same company, major pivots, painful lessons, and one moment where he nearly lost everything after discovering the business was in serious financial trouble. Jeff and Steven also discuss what happened after the final exit, how he prepared the company to run without him, and why founders should build years in advance if they want to sell without being trapped inside the deal. The conversation also explores Steven's endurance journey, from not being able to swim more than two laps to completing Ironman races, qualifying for Kona through persistence, attempting Mount Everest, and continuing to chase big goals. For Steven, entrepreneurship and endurance are deeply connected. Both require planning, discipline, pivots, setbacks, stamina, and the willingness to keep going.

In this episode: ● How Steven immigrant upbringing shaped his drive ● Why he started his first company ● How he built a business around technology shifts ● What it means to sell the same company multiple times ● The painful lesson that almost cost him everything ● Why founders should build companies that do not need them ● How entrepreneurship and endurance training connect ● Why big goals become possible through small steps

If you are a founder, entrepreneur, leader, athlete, or someone facing a goal that feels too big, this episode will remind you that anything is possible when you commit, prepare, and take the next step. Connect with Jeff Munn and tune into more conversations on Pick Now.

What if the fight you keep having with life is really the fight you are having with yourself? In this episode of Pick Now, Jeff Munn sits down with Daryl Dittmer, author, coach, sales trainer, and entrepreneur. Daryl shares his journey from getting sober at 19 to building a life rooted in freedom, work ethic, teachability, and self-honesty. He opens up about growing up in the Midwest, feeling pressure at a young age, falling into drinking and drugs, and eventually entering recovery after an intervention changed the direction of his life. Jeff and Daryl also explore his entrepreneurial path, from building dorm lofts in college to working in sales, earning ownership, buying businesses, writing books, and helping others through coaching and sales training. Through every stage, Daryl kept stepping into new things, even when fear was present. The conversation also centers on one of Daryl's most important lessons: "When you stop fighting, the fighting stops." He explains how much of life can become a wrestling match with fear, discomfort, ambition, expectations, and ourselves. But freedom often begins when we stop fighting life and start being honest about what is working, what is not, and who we are becoming.

In this episode:

• How Daryl got sober at 19
• Why recovery changed the direction of his life
• How his first business started in college
• Why fear still shows up before something new
• What work ethic taught him about responsibility
• Why freedom became more important than money
• How he learned to stop fighting himself
• Why staying teachable matters at every stage

If you have ever felt stuck in fear, pressure, addiction, work, ambition, or your own expectations, this episode is a reminder that growth does not always come from fighting harder. Sometimes it starts when you stop fighting.

Connect with Jeff Munn and tune into more conversations on Pick Now.

What if success is not just what you build, but how much truth and love you are willing to bring with you?

In this episode of The Pick Now Podcast, Jeff Munn sits down with his longtime friend and colleague Trish Kendall, founder of Enduring Success Strategies, for a deeply personal conversation about love, vulnerability, success, speaking, friendship, and the courage it takes to bring your whole story into your work. Trish shares how her journey from trauma, addiction, and survival eventually shaped the work she does today as a consultant, coach, and inspirational speaker. Together, Jeff and Trish explore the difference between professional success and personal truth, why love is not just an emotion but an action, and how real connection requires the courage to be seen. They also talk about the fear of needing people, the protective armor of independence, the practice of vulnerability, and the barriers that can keep someone from fully stepping into their mission. Through one powerful story about a 15-year-old girl who heard Trish speak, the conversation comes back to the heart of her work: helping one person see what is possible.

In this episode:

• Why love is a verb, not just a feeling
• How professional success can hide personal loneliness
• Why vulnerability creates deeper friendship and trust
• How independence can become protection from being hurt
• What it means to bring your whole story into your work
• Why inspiring one person can be the mission

If you have ever built success while still holding parts of yourself back, this episode will challenge you to look at what is still hidden, what is still protected, and what might become possible when love becomes a practice. Connect with Jeff Munn and tune into more conversations on The Pick Now Podcast.