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.

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.

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.

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.