The Pick Now Podcast with Jeff Munn

In this episode of Pick Now, Jeff Munn talks with Jenn Drummond about entrepreneurship, reinvention, motherhood, resilience, and what it means to stop waiting for "someday." Jenn shares how she moved from wealth management into building her own company, then later stepped back from the business as family life forced her to learn how to delegate and let go. Jenn explains how nearly dying in a car accident changed the way she looked at her life. She realized she had spent years managing everything around her instead of fully living it, and that many of the things she wanted to do had been pushed into an undefined future. That experience became a turning point toward being more present and intentional. That mindset eventually led Jenn into mountaineering. What began as an idea to climb a mountain for her 40th birthday grew into an attempt to become the first woman to climb the Seven Second Summits. Despite having no previous climbing experience, she committed to the challenge and learned the skills along the way.

Jeff and Jenn also discuss how her pattern of saying yes, getting in over her head, and figuring things out has shown up throughout her life. Jenn describes her story as repeatedly going from nothing to something—whether building a business, raising seven children, or setting climbing records.

The conversation closes around Jenn's current mission: helping people turn their "somedays" into action. She explains that almost everyone has things they intend to do eventually, but without action those intentions can become regret. Her goal is to help people identify what matters, break it into manageable steps, and make ordinary days more meaningful.

In this episode: ● Building a business before feeling fully ready ● Learning through sales and rejection ● Letting go of control and learning to delegate ● Losing yourself in achievement and motherhood ● How a near-death experience changed Jenn's priorities ● Moving from managing life to living it ● Saying yes before having all the answers ● Going from no climbing experience to world records ● Breaking big goals into smaller steps ● Turning intention into action ● Why "someday" can become regret ● Making ordinary days more meaningful

Jenn's message is that extraordinary experiences matter, but most of life happens on ordinary days. Instead of waiting for the perfect moment, she encourages people to participate in their lives now, take the next step, and turn the things they keep postponing into something real.

In this episode of Pick Now, Jeff Munn talks with Drew Schiller, founder of Validic, about entrepreneurship, leadership, building a company, and the lessons that come with a recent exit. Drew shares that he had an entrepreneurial instinct from a young age, from creating a neighborhood newsletter as a kid to trying to book gigs for his high school brass quartet. After college, he started doing web and design work on his own, but quickly learned that making money from projects was different from knowing how to build a real business. A major focus of the conversation is Validic's early journey. Drew explains how the company went through multiple pivots before finding the idea that took off: helping health and wellness companies connect data from consumer health apps and devices. That shift led to major traction, including early customer interest, large demo demand, and a seed round led by Mark Cuban. Jeff and Drew also talk about the pressure of startup leadership. Drew shares how fast growth forced him to learn how his presence affected the team, how hard it was to balance work and family, and how he eventually realized that not everything was an emergency. Later, Drew opens up about the emotional impact of a major exit falling apart during Covid after the deal was nearly complete. He describes the loneliness, disappointment, and personal processing that followed, as well as the leadership lessons he learned by listening instead of reacting.

In this episode: ● How Drew discovered his entrepreneurial drive ● Why early business mistakes became important lessons ● How Validic pivoted into a stronger market opportunity ● What happened after Mark Cuban invested ● Why startup success can arrive after years of unseen work ● How founders learn to let go as companies grow ● The personal cost of always treating work like an emergency ● What Drew learned when a major exit collapsed ● Why listening can be stronger than having the answer ● How his 2026 exit opened a new chapter

This episode is a reminder that entrepreneurship is not just about building a company. It is about learning how to lead, how to grow, how to survive disappointment, and how to become the kind of person who can handle the next chapter.

In this episode of Pick Now, Jeff Munn talks with Ted Santos, founder, chairman, and CEO of Turnaround Investment Partners, about leadership, mindset, transformation, and what it takes to help people perform in the middle of chaos. Ted shares how his early career shaped the way he thinks about business and leadership. After working in sales, he stepped into a struggling transportation company that was growing so quickly it was falling apart. When the president challenged him after hearing his suggestions, Ted told him directly that he believed he could run the company better. Within two weeks, the president gave him the role. A major focus of the conversation is how leaders can become bottlenecks without realizing it. Ted explains that when people are trained to bring every problem to the top, they stop thinking for themselves. His approach was different. Instead of giving answers, he asked questions, helped people think through problems, and coached them until they could solve issues on their own. Jeff and Ted also talk about blind spots, mental barriers, and the stories people inherit about themselves. Ted explains that awareness alone is not always enough. People need to reverse engineer the moments and beliefs that still control their behavior. Later, Ted shares powerful examples from his work, including leaders and salespeople who were stuck in old patterns until they learned where those patterns started. Through questions, reflection, and mindset training, they were able to change how they showed up.

In this episode: ● Why fast growth can create chaos ● How leaders accidentally become bottlenecks ● Why asking questions can build stronger teams ● How accountability can transform culture ● Why blind spots control behavior ● Why awareness is not the same as change ● How mindset training helps people navigate pressure ● Why real leadership means helping others become capable

This episode is a reminder that leadership is not about being the hero in every situation. It is about helping people think, grow, take ownership, and become more powerful than they knew they could be.

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.