Pay Your Dues with Greg Inglin: Exploring the Struggle before Success

Greg Inglin
  • 5.0 (12)
  • SELF-IMPROVEMENT
  • UPDATED WEEKLY

Curious what drives the world’s most successful leaders to keep going even when failure seems inevitable? This podcast is a motivational discussion for ambitious leaders, entrepreneurs, and those committed to personal growth. We’ll uncover stories of mental resilience & leadership challenges from athletes, business leaders, and entertainment icons. Whether you’re building a career, seeking redemption stories, or the best motivational podcast for self-improvement, this podcast delivers actionable advice. Subscribe to the podcast for lessons from failure and the motivation to progress forward.

  1. 5D AGO

    Keira D'Amato: From "Hobby Jogger" to American Marathon History

    At one time, Keira D’Amato described herself as a “hobbyjogger”, but she’s about the only one that would see it that way. After a stellar high school and college running career, Keira became a professional runner, but injuries and the pressure that comes with being a pro lead her to retire in her mid 20’s. She took eight years off from running, got married, had twokids, and that’s when the hobby kicked in. On this episode of Pay Your Dues, Keira takes us through the amazing transformation she engineered in her mid-30’s, going from hobby jogger to one of the faster marathon runners in the world. She topped that off by breaking the American Women’s marathon record, an amazing feat for anyone, let alone someone that had been away from running for nearly adecade. Her book, Don’t Call it a Comeback, is chalk full of greatstories and plenty of laughs, and so is this conversation. Keira is the “every woman”, except she just happens to be really fast.  Her story will inspire you to seek new challenges and to have fun along the way. (Note, after taping this episode, Keira decided to address ahip injury that had been bothering her, so she will not be running the Boston Marathon in 2026, but we do look for her to get back on her feet and to come back strong for her future races!) Guest Resources: IG: @keiradamato Website: www.keiradamato.com Book: Don’t Call it a Comeback Guest idea? Feedback? Connect with Greg on his websiteor LinkedIn. If you’re loving the podcast, please leave a 5-star rating!  Want to skip to the good part?Here’s this episode’s segments: Chapters   00:00 The Boston Marathon 04:31 Round One vs. Round Two: A Runner's Evolution 07:22 Finding Balance: Motherhood and Running 10:33 The Power of Community in Running 13:30 Overcoming Guilt: A Mother's Perspective 16:23 The What If Mentality: Embracing Possibilities 19:45 Breaking Records: The Houston Marathon Experience 29:39 Breaking Barriers: The Journey to a New Record 34:22 Life After the Record: Balancing Fame and Family 37:01 Playing with House Money: Embracing the Second Chance 38:45 Adapting Training: The Evolution of a Runner 40:36 Mental Toughness: Preparing for the Pain Cave 44:11 Welcoming Community: The Support of Fellow Runners 46:26 Lessons from Disappointment: The Olympic QualifierExperience 49:47 Training at Altitude: New Challenges and Opportunities 52:56 Encouragement for Dreamers: Pursuing GoalsAuthentically 54:21 Aiming for the Future: The Road to LA 2028 55:49 The Mental Benefits of Running: More Than Competition 57:02 Overcoming Doubt: The Power of Belief 59:11 Not a Comeback: A Journey of Growth Guest idea? Feedback? Connect with Greg on his websiteor LinkedIn.   Ifyou’re loving the podcast, please leave a 5-star rating!   Want to skip to the good part?Here’s this episode’s segments:

    1h 1m

  2. FEB 10

    James Donaldson: NBA, Mentors, and His Life Saving Battle with Depression

    James Donaldson has an amazing story you need to hear. He enjoyed a long, productive basketball career spanning 20 years, with 14 of those in the NBA. He is a big man with a big heart, and his energy can fill a room.  When he moved from the basketball court to the business world, it was a smooth transition. But that all changed suddenly in 2015 with a trip to the emergency room. A heart condition he knew nothing about almost killed him.After twelve hours of surgery, two weeks in a medically induced coma, and three months in intensive care, his battle was only beginning.  Four major surgeries in five years, and his world was falling part. James lost it all: his health, life savings, marriage, business, and home all within a year's time. Hedeclared bankruptcy, lost his home to foreclosure, had to close his long-running business. James was struggling in silence and contemplated suicide.  He battled through the darkness over twelve difficult months and decided to share his story in order to help others. From those dark days he found hope, joy, and purpose and he is committed to speaking up on the topic of depression and mental health. In this conversation, James takes us through his journey and shares his efforts to inspire others to seek help and find purpose in their lives. Guest Resources: Book: Celebrating your gift of Life: From the Verge of Suicide to a life of Purpose and Joy. Foundation: Your Gift of Life Foundation https://yourgiftoflife.org/ Podcast: Standing Above the Crowd Facebook: https://www.facebook.com/james.donaldson.9634340 Guest idea? Feedback? Connect with Greg on his websiteor LinkedIn.If you’re loving the podcast, please leave a 5-star rating! Want to skip to the good part? Here’s this episode’s segments:Chapters 00:00 Nostalgic Beginnings: A Basketball Camp Reunion 02:58 Community Impact: The Role of Sports in Youth Development 05:50 Basketball Legacy: Seattle's Rich History 08:41 From Player to Professional: James Donaldson's Journey 11:08 Mentorship in Sports: Lessons from George Raveling and Lenny Wilkins 14:13 Life After Basketball: Transitioning to Business 17:12 Health Crisis: A Life-Altering Experience 19:53 Struggles with Mental Health: The Aftermath of Adversity 29:42 Facing Darkness: A Personal Journey 33:50 The Catalyst for Change: Tyler's Story 36:21 Understanding Hopelessness: The Depth of Despair 41:11 Breaking the Stigma: Men and Mental Health 45:00 The Need for Representation: Mental Health in Communities of Color 47:38 Empowering the Next Generation: Speaking to Youth 50:58 The Impact of Social Media: A Double-Edged Sword 55:58 The Importance of Connection: Reaching Out to Others 59:54 A Life of Purpose: From Athlete to Advocate

    1h 9m

  3. JAN 20

    Jordan Brady: Commercial Directing in Hollywood, and the Love of the Craft

    In this fun and engaging conversation, Jordan Brady shareshis journey from stand-up comedian to successful commercial director, emphasizing the importance of identity, creativity, and collaboration. He discusses the influence of his family on his career, the lessons learned from his time spent on the road as a comedian, and the evolution of filmmaking in the age of AI. Brady also reflects on the joy of mentorship and the significance of giving back to the community, all while maintaining a sense of humor and passion for his craft. This is someone that clearly cares about his workplace, his team, and having fun along the way. Guest Resources:Podcast: https://podcasts.apple.com/us/podcast/respect-the-process/id712578722 IG: @thatjordanbrady Website: www.trueagent.tv LinkedIn: https://www.linkedin.com/in/thatjordanbrady/ Book: Commercial Directing Voodo About My Guest: Jordan Brady has directed over 1300 commercials. Plus four feature films, (“Dill Scallion”, “Waking Up In Reno”) three full-length documentaries (“I Am Comic” trilogy), one Netflix comedy special in Maria Bamford's living room. A stand-up comedian in a prior life, he’s credited with originating the now-ubiquitous phrase “Bow Chicka Bow Wow” in the 80’s. In the 90’s, he hosted game shows on MTV, NBC and Comedy Central. His short return to stand-up was in 2016 to perform in Afghanistan for our U.S. troops while filming "I Am Battle Comic." Brady donated 100% of the profits from the film to veterans and military families. He’s the founder of both True Gent & Commercial Directing Film School and hosts the filmmaking podcast "Respect The Process." Guest idea? Feedback? Connect with Greg on his ⁠website⁠ or ⁠LinkedIn⁠. If you’re loving the podcast, please leave a 5-star rating!   Want to skip to the good part? Here’s this episode’s segments: Chapters 03:40 The Role of Fatherhood in Career 06:44 From Ohio to LA: The Creative Path 09:43 Stand-Up Comedy: The Early Days 12:49 The Move to Los Angeles: Chasing Dreams 15:49 Navigating the Comedy Scene 18:40 Transitioning Behind the Camera 24:15 First Steps into Commercial Directing 24:45 The Evolution of a Filmmaker 27:43 Balancing Film and Commercial Work 30:41 Reflections on Career Choices 34:16 The Journey of a Commercial Director 34:52 Comedy's Influence on Directing 36:18 Navigating the Commercial Landscape 38:08 The Role of Actors in Commercials 39:47 The Joy of Collaboration 42:24 Creative Problem Solving in Filmmaking 44:43 Self-Taught Filmmaking and Learning 47:42 The Value of Film School 49:29 Teaching Filmmaking: A Personal Journey 53:10 Creating Educational Content for Filmmakers 56:32 The Impact of AI on Filmmaking 59:51 The Future of Commercial Directing 01:05:33 The Pinnacle of Commercials: Super Bowl Ads 01:07:50 Memorable Moments in Filmmaking 01:13:28 The Importance of Passion in Work

    1h 18m

  4. JAN 6

    Alan Stein Jr: Lessons from the NBA and a "Next Play" mentality

    Alan Stein Jr. spent 15 years working with some of the best NBA athletes in the world and he's taken those lessons into the next phase of his life. In this conversation, Alan discusses the power of mindset and the journey of self-improvement which are highlighted in his most recent book, Next Play. Alan shares insights on how to overcome fear, the importance of self-compassion, and practical steps for living intentionally. Alan also reflects on the human side of athletes and the commonalities between performance in sports and business. Guest Resources: website: https://alansteinjr.com Alan on IG: @alansteinjr About My Guest: Alan Stein Jr. is an internationally renowned corporate keynote speaker and performance coach who spent more than fifteen years working with some of the highest-performing athletes on the planet, including NBAsuperstars Kevin Durant, Stephen Curry, and Kobe Bryant. He delivers a powerful, high-energy message from stage, and his client list includes many of the most recognized brands in the world, such as Pepsi, Charles Schwab, American Express, Spotify, and Starbucks. A masterful storyteller, he revealshow the same strategies that elite athletes use to perform at a world-class level will help organizations improve performance, productivity, cohesion, accountability, and culture. He is the proud father of twin sons (Luke and Jack) and a daughter (Lyla), has written two previous books ( Raise Your Game and Sustain Your Game ), and lives just outside of Washington, DC. Guest idea? Feedback? Connect with Greg on his website or LinkedIn. If you’re loving the podcast, please leave a 5-star rating!   Want to skip to the good part? Here’s this episode’s segments: 00:00 New Year, New Mindset 14:10 Emotional Resilience and Growth 24:33 Lessons from the Court: Insights from NBA Greats 30:36 Always Becoming: The Journey of Self-Improvement 31:18 Overcoming Negative Self-Talk 34:22 Compassionate Self-Talk: Treating Yourself Like a Loved One 36:39 Mindset: The Power of Choice 40:56 Next Play: Embracing the Present Moment 45:24 Facing Fears: The Importance of Being Present 48:37 Bookends of the Day: Intentional Living 51:35 The Human Side of Professional Athletes 53:46 Performance Improvement in Business 57:17 Optimism for the Future: The Best is Yet to Come

    1 hr

  5. 12/22/2025

    George Gilder: Writing and Running at 86 Years Young

    In this episode of Pay Your Dues, Greg Inglin talks withGeorge Gilder, a prominent American economist, futurist, author, and investor, famous for his influential work on supply-side economics (especially his book Wealth and Poverty) and his insightful analyses of technology's impact, predicting the rise of the internet and blockchain.  But did you know that George is also an accomplished runner, who is still putting in the miles at the age of 86 years old? Amazing! George shares his story of how he started running, and whyit is so important to him to this day.  Often running six miles per day, George recently finished second in the World Championship 10K for his age division.  This inspiring story of perseverance and pure enjoyment for movement will help motivate you in your own life.  Guest Resources: The Gilder Technology Report: https://www.gilderreport.com/ Strava: https://www.strava.com/athletes/49124414 Facebook: https://www.facebook.com/ggilder1   Guest idea? Feedback? Connect with Greg on his website or LinkedIn. If you’re loving the podcast, please leave a 5-star rating! Want to skip to the good part? Here’s this episode’s segments: 00:00 The Joy of Coaching and Running 03:53 A Lifelong Passion for Running 06:38 Staying Active in Winter 09:15 Competitive Spirit in Aging 12:06 The Connection Between Running and Mental Clarity 14:24 Diet and Longevity 16:54 Managing Expectations in Running 19:27 The Philosophy of Time and Money 26:45 The Value of Time as Currency 33:23 The Evolution of Technology and Time Management 40:06 Predictions and Reflections on Technology 46:59 The Impact of AI and Future Technologies 54:40 Personal Reflections and Future Aspirations

    1h 3m

  6. 11/18/2025

    Anthony Robles: From Underdog to Unstoppable, A Story of Resilience

    There are few examples of resilience and perseverance betterthan Anthony Robles. Born with one leg, Robles refused to see limitation. Instead, he saw opportunity – and turned that belief into an NCAA Wrestling Championship Title, a best-selling book, and a major motion picture called Unstoppable. Join Greg Inglin as he looks back at this amazing journey with Anthony, who shares his struggles along the way. How he almost quit in high school and then again in college, only to find hope from a group of third grade students and their letters of encouragement. Anthony’s mom played a big part in his mental fortitude, anddespite their struggles as a family, Anthony managed to navigate some tough situations without a strong father figure in his life. Hollywood loves his story too, as Amazon produced a majormovie where Jennifer Lopez plays his mom, and captures the struggle and the triumph of his journey.  This is not a wrestling story…it’s one of faith, perseverance, and a belief despite facing the biggest odds.  Guest Resources: Anthony on IG: @arobles125 The Book: Unstoppable: From Underdog to Undefeated The Movie: Unstoppable on Amazon Prime  Gues idea? Feedback?  Connect with Greg on his website orLinkedIn. If you’re loving the podcast, please leave a 5-star rating!  Want to skip to the good part? Here’s this episode’s segments: 00:00 The Essence of Wrestling 04:11 Overcoming Early Challenges 07:10 The Importance of Support Systems 10:15 Navigating Crossroads in Life 13:12 The Role of Faith and Motivation 16:26 Resilience in the Face of Adversity 19:07 The Journey to the National Championship 22:18 The Power of Perspective 25:12 Becoming Unstoppable 28:03 Giving Back and Inspiring Others

    32 min

  7. 11/04/2025

    Sebastien Page on the Psychology of Leadership and the Power of Long Term Goals

    In the high-stake world of high finance, pressure comes withthe job and can cause many great minds to burnout. Learning how to navigate such a stressful world has led Sebastien Page into a deep study on learning, leadership, and fulfillment.  Join Greg Inglin as he explores Sebastien’s book “The Psychology of Leadership” and the practical elements we all can use form his studies. Sebastien is Chief Investment Office at T. Rowe Price,overseeing a team that manages more than $500 Billion in assets. You can often find him on CNBC or Bloomberg TV.  Sebastien opens up about his upbringing in Canada, and what he learned from his father who was both a finance professor and a cattle rancher.  After a near fatal bout with burnout, Sebastien started to study work cultures and habits that created the best environments.  Greg and Sebastien explore the intrinsic motivation and how thinking long term creates short term benefits mentally and physically.  Guest Resources: Sebastien on LinkedIn: linkedin.com/in/sebastien-page Sebastien on IG: https://www.instagram.com/sebastienpagebook/ About My Guest: Sébastien Page is the Global Multi-AssetDivision's head and Chief Investment Officer at T. Rowe Price. He is an investment professional with extensive experience at firms like PIMCO and State Street Global Markets. Page is also an author of several finance books and articles, and is a frequent commentator on financial media. He has beenwith T. Rowe Price since 2015, where he leads a team that manages over $500 billion in assets. Before joining T. Rowe Price, he held senior positions at PIMCO and State Street Global Markets. Page holds a Master of Science in finance and a Bachelor ofBusiness Administration from Sherbrooke University and is a Chartered Financial Analyst® (CFA) charterholder. He wrote "The Psychology of Leadership" and co-authored "Factor Investing and Asset Allocation" and "Beyond Diversification". He has also co-authored severalaward-winning research papers. Page is a regular on financial media outlets like Bloomberg TV and CNBC.  Guest idea? Feedback? Connect with Greg on his websiteor LinkedIn. If you’re loving the podcast, please leave a 5-star rating!  Want to skip to the good part? Here’s this episode’s segments: 00:00 Growing Up on a Farm: Lessons in Work Ethic 04:12 The Psychology of Flow and Engagement 07:04 Distraction in Modern Society 09:50 The Intentionality of Leadership 12:56 The Power of Consistency and Habits 16:03 Understanding Leadership through Psychology 19:12 The Role of Personality in Leadership 21:59 The Journey of Writing a Book 24:59 The Importance of Mindset in Performance 32:51 The Extrovert-Introvert Leadership Debate 35:35 Key Personality Traits for Leadership 40:40 The Role of Stress in Performance 44:41 Breathing Techniques and Decision Making 48:45 Learning from Losses and Building Resilience 52:52 The Importance of Meaning and Engagement 55:52 Understanding and Preventing Burnout 01:01:28 Thinking Long-Term for Leadership Success

    1h 4m

  8. 10/21/2025

    Craig Robinson: The Pursuit of Happiness: The Courage to Pivot and Finding Your Flow

    In this conversation, Craig Robinson opens up about his pivot from the C-Suite to author, mentor, and advocate for the pursuit of happiness. After attending MIT and Harvard Business School, Craig’s climb up the corporate ladder was impressive and his leadership skills put him at the top of some of the country’s largest real estate firms. However, Craig was seeking fulfillment in other ways that led to a pivot and his desire to take a different path. Craig talks about putting ego aside, seeking personal growth and joy by investing in what mattered to him most: relationships, career, and faith.  This self-discovery led to better life balance, mental health, and his desire to research and write a book on happiness. Craig also reflects on his heritage and the impact of his ancestors, highlighting the significance of understanding one's identity. This is a great conversation for those that areseeking change, big or small, and how to curiosity over conviction can open our minds to new possibilities. What you can expect from this episode: How the influence of African American leaders in Atlanta inspired CraigHow education and mentorship played a crucial role in Craig's successWhy Craig's journey was not linear; it was filled with challengesThe importance of nurturing individual talents in childrenEmbracing change and adapting to new opportunities is essential. Fulfillment comes from focusing on purpose,community, and being stretchedHow pursuing a portfolio career can lead to greater balance and joyWhy courage is essential when changing life prioritiesWhy happiness cannot be crowdsourced; it must come from withinHow relationships are key to long-term happiness and healthExamples of how small, intentional changes can lead to greater happinessGuest Resources: www.craigrobinson.com⁠ LinkedIn: ⁠https://www.linkedin.com/in/craigmrobinson/⁠   Guest idea? Feedback? Connect with Greg on his ⁠website⁠or ⁠LinkedIn⁠. If you’re loving the podcast, please leave a 5-star rating! Want to skip to the good part? Here’s this episode’s segments: 00:00 Roots in Atlanta: A Journey of Influence 02:58 The Power of Education and Mentorship 06:01 Understanding Heritage and Identity 09:07 Navigating Academic Challenges and Opportunities 11:58 The Role of Community and Support 14:53 Finding a Path in Real Estate 17:51 The Importance of Networking and Seizing Opportunities 20:48 Seasons of Career Growth and Leadership 24:02 Embracing Leadership and Personal Fulfillment 30:23 Finding Your Flow: The Key to Fulfillment 31:44 The Courage to Pivot: Embracing Change in Career 36:01 Happiness: A Choice or a Discipline? 39:39 The Role of Relationships in Happiness 48:11 Wrestling with Identity: The Ego's Impact on Happiness 51:22 Surprising Insights: What Really Brings Happiness? 55:40 Creating Space for Happiness: Small Steps to Big Changes About My Guest:  Craig Robinson is an experienced independent board director, c-suite executive and advisor forcommercial real estate, professional services and technology companies. Craig currently serves as an independent director for Lessen, Roofstock, and Second Nature. He is also a Strategic Advisor to Dunes Point Capital, a privateinvestment firm that has invested over $5B in industrial and service companies since 2001. Over the course of his career, Craig has led business units within both large global public companies and private mid-cap growth businesses such as Industrious (now CBRE), WeWork, Newmark, and Colliers International. He is a member of the Harvard Business School Alumni Board and has served as advisor to several growth companies. Craig earned his MBA from Harvard Business School, and his BS from the Massachusetts Institute of Technology. Outside of work, Craig is a founding member of the Leadership Now Project where he is a passionate advocate for working and fair democracies.

    1h 4m
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Ratings & Reviews

5
out of 5
12 Ratings

About

Curious what drives the world’s most successful leaders to keep going even when failure seems inevitable? This podcast is a motivational discussion for ambitious leaders, entrepreneurs, and those committed to personal growth. We’ll uncover stories of mental resilience & leadership challenges from athletes, business leaders, and entertainment icons. Whether you’re building a career, seeking redemption stories, or the best motivational podcast for self-improvement, this podcast delivers actionable advice. Subscribe to the podcast for lessons from failure and the motivation to progress forward.

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