Ep: 120: Stanley McChrystal: Four-star General (Ret.) on character and leadership

General Stanley McChrystal is a retired four-star general and former commander of U.S. and International Forces in Afghanistan and the Joint Special Operations Command (JSOC), where he led the nation’s most elite counterterrorism efforts. With 34 years of military service, he’s recognized for reshaping modern warfare and pioneering team-based leadership approaches in high-stakes environments. Today, he is the founder and CEO of the McChrystal Group, a leadership advisory firm that helps organizations adapt and thrive in complex, fast-changing environments. He is the author of multiple bestselling books, and his most recent work, On Character: The Choices That Define Us, explores how leaders are remembered—not just for what they achieve, but for who they are.

 

Summary

In this conversation, retired four-star General Stanley McChrystal reflects on the qualities that define meaningful leadership, focusing on character, culture, and personal growth. He shares how he almost got expelled from West Point for disciplinary issues and poor study habits, and how that period of immaturity helped shape his evolution as a leader. He talks about his famously intense morning routine, including waking up at 4 a.m. and working out for 90 minutes, and how these habits are rooted in self-discipline and clarity of purpose.

McChrystal defines character as a combination of convictions and the discipline to live by them. He makes the case that it’s not enough to believe in the right things if you don’t act on them. He also challenges the idea that someone can be one kind of person in private and another in public. To him, character is consistent, and integrity either holds up across all domains or it doesn’t hold up at all.

He speaks openly about moral ambiguity in leadership, including moments when he disagreed with decisions made by the administration but chose to follow orders because they were legal and within the boundaries of his role. He warns of the dangers of rationalizing small compromises over time, which can slowly erode a person’s values.

McChrystal also explains why elite military units like the Rangers are not necessarily made up of elite individuals. What sets them apart is a shared commitment to high standards. He believes the same principle applies in business and argues that a strong organizational culture drives performance more than talent or strategy.

The conversation touches on charisma, humility, and how leadership style evolves over time. McChrystal admits he wasn’t always consistent in his early years and had to learn to lead in a way that built trust and clarity. He also discusses the importance of critical thinking, especially in an era where media narratives often distort reality.

Finally, he reflects on the abrupt end to his military career following the Rolling Stone article and how he chose to move forward rather than dwell on the past. He credits his wife and close friends for helping him shift his focus and find new purpose in civilian life, including launching a leadership advisory firm, teaching at Yale, and writing multiple books. His latest, On Character, is a deep exploration of what it means to live by your values and be someone others can count on.

 

Takeaways

  • Morning routines and physical discipline help create structure and momentum
  • Character comes from having strong convictions and the discipline to live by them
  • Integrity in your personal life matters just as much as in your public role
  • A strong culture built on shared standards can outperform raw talent
  • Good leadership means knowing how to handle moral complexity, not just following orders
  • The best leaders combine confidence with humility and know when to show each
  • Charisma only matters if it’s backed by substance, courage, and consistency
  • It’s easy to be misled by the media, which makes critical thinking more important than ever
  • Leadership styles change with experience, but consistency builds trust
  • Moving forward after setbacks starts with choosing not to live in the past

 

Notes

Books:

On Character: Choices That Define a Life

Team of Teams: New Rules of Engagement for a Complex World

My Share of the Task: A Memoir

Organizational consulting:

McChrystal Group

Ep: 119: Kwane Stewart: CNN Hero of the Year and Founder of Project Street Vet

Dr. Kwane Stewart is a veterinarian and the co-founder of Project Street Vet, a non-profit that provides free veterinary care for the pets of people experiencing homelessness in cities across the country.  His work earned him CNN Hero of the Year in 2023. His book is titled: What It Takes to Save a Life: A Veterinarian’s Quest for Healing and Hope. 

Summary

In this conversation, Dr. Kwane Stewart, a veterinarian and co-founder of Project Street Vet, shares his journey from a successful veterinary career to providing free care for pets of the unhoused. He discusses the importance of empathy, the challenges faced by both animals and their owners in the homeless community, and the emotional toll of veterinary work. Dr. Stewart emphasizes the need for kindness and understanding towards those experiencing homelessness and highlights the strong bonds between them and their pets. His mission is to expand Project Street Vet to more cities, advocating for both animal welfare and human dignity.

Takeaways

  • Powerful childhood experiences, like watching The Black Stallion, can create powerful emotions that inspire career paths.
  • Bullying can lead to empathy and a desire to protect others.
  • The suicide rate among veterinarians is notably high due to emotional stress.
  • Project Street Vet was born from a desire to help animals in need.
  • Building trust with the unhoused community is essential for effective care.
  • Many unhoused individuals have strong bonds with their pets, often prioritizing them over their own housing.
  • Funding and volunteer support are crucial for sustaining veterinary care for the unhoused.
  • Kindness, compassion, and empathy are vital in addressing homelessness and animal welfare.

Notes

Book: What It Takes to Save a Life: A Veterinarian’s Quest for Healing and Hope

Veterinary care charity: Project Street Vet

Personal Website: Dr. Kwane Stewart

Ep: 118: Michael Grab: World’s Greatest Rock Balancing Artist on Making the Impossible Possible

Michael Grab is one of the world’s premier rock balancing artists.  He has created rock art all over the world and has inspired a global movement for stone balancing art.

Summary

In this conversation, Michael Grab, a renowned rock balancing artist, shares insights into his creative process, the philosophy behind his art, and the technical aspects of balancing rocks. He discusses how he finds inspiration in nature, the evolution of his hobby into a professional pursuit, and the meditative state he enters while creating his sculptures. The conversation also touches on the ephemeral nature of his work, emphasizing the beauty in its temporary existence.

In this conversation, Michael Grab discusses his journey as a rock balancing artist, emphasizing the ephemeral nature of his work and the meticulous process of capturing it through photography and film. He reflects on the transition from a conventional job to pursuing his passion full-time, driven by a desire for creative fulfillment. Grab shares insights on self-competition and the personal standards he sets for his art, ultimately defining excellence as the ability to inspire himself through his creations.

Takeaways

  • His creative process is organic, often allowing the rocks to dictate the final arrangement.
  • He finds inspiration in nature and specific locations that resonate with him.
  • Rock balancing started as a hobby influenced by a psychedelic experience.
  • The art form is highly technical, requiring a deep understanding of gravity and balance.
  • Michael practices for hours, often pushing his limits to create more complex structures.
  • He experiences a flow state while working, feeling deeply connected to the environment.
  • The process of balancing rocks is meditative and exists solely in the present moment.
  • Michael embraces the ephemeral nature of his art, often dismantling structures after photographing them.
  • He believes that the journey of mastery in rock balancing is ongoing and never truly finished.
  • He doesn’t set strict standards but rather focuses on the process and his growth.

Ep: 89: James Burrows: King of Sitcoms

Jimmy Burrows has directed more than one thousand episodes of sitcom television and has earned eleven Emmy Awards and five Directors Guild of America Awards. In 1974 he began his television career directing episodes of The Mary Tyler Moore Show, The Bob Newhart Show, and Laverne and Shirley. He became the resident director on Taxi and co-created Cheers, directing 243 of the 273 episodes, as well as all 246 episodes of Will and Grace. He has directed the pilots of multiple episodes of Frasier, Friends, Mike & Molly, the pilots of Two and a Half Men and The Big Bang Theory, and hundreds of other shows.  His new book is titled: Directed by James Burrows: Five Decades of Stories from the Legendary Director of Taxi, Cheers, Frasier, Friends, Will & Grace, and More.

 

Some interesting insights from this episode:

  • He operates with kindness. Everyone has to row together and pull equally with everyone else. He doesn’t allow ego to get in the way.
  • He has the perfect temperament for TV directing. He doesn’t lose his temper, he’s patient, he has low ego, and he knows how to encourage others.
  • He feels as a director it’s important to “die with your boots on”. That is, to try to do something to make a difference.  To provide input to make the best show possible.
  • When deciding whether to work on a show, he likes to meet with the writer and have him/her defend themselves but not be defensive.
  • When asked about same-sex marriage, then Vice President Joe Biden said, “I think Will & Grace probably did more to educate the American public than almost anything anybody’s ever done so far. People fear that which is different. Now they’re beginning to understand.”
  • His success is attributed to his ability to create a harmony on the set so everyone’s involved in making the show better. On his sets, you have to check your ego at the door.
  • “Excellence is to try to be the best you can be in your particular field.”

 

Notes:

Book: Directed by James Burrows: Five Decades of Stories from the Legendary Director of Taxi, Cheers, Frasier, Friends, Will & Grace, and More

Ep 46: Chris Wilson: From a life in prison to a life of purpose

At the age of 17, Chris Wilson was sentenced to life for murder.  He turned his life around while in prison and was released after 16 years.  Today he is the owner of Barclay Investment Corporation, a social enterprise specializing in residential and commercial contracting work and employing out of work Baltimore residents.  His other business ventures include the House of DaVinci, a high-end furniture restoration and design company, and Master Plan Productions, a social impact content development company. His book is called: The Master Plan: My Journey from Life in Prison to a Life of Purpose.

 

Some interesting insights from this episode:

 

  • At the age of 17, Chris Wilson was sentenced to life in prison for murder.
  • Despite being sentenced to life, Chris believed that if he focused on turning his life around, he would get his sentence reduced and be set free after 7 years. He called this kind of thinking a “positive delusion”.
  • While in prison, he created a “Master Plan” which was a list of goals he wanted to accomplish in his life. He shared the list with his grandmother and the judge because he felt it was important to have others hold him accountable.
  • It was also important to include a number of shorter term goals on the Master Plan which were easier and quicker to accomplish to boost his confidence and create momentum.
  • He went to therapy to learn how to stop making excuses and take full responsibility for his past actions in order to move forward.
  • Instead of chasing money and living an easy life, he chose to give back to the community by starting a company which employed out of work residents including recently released prisoners.
  • It’s important to surround yourself with a support system of people you can turn to in order to stay on track and not revert back to bad habits.
  • “Excellence is pushing yourself to achieve high standards and doing so in a way that’s humble and considerate.”

Ep. 3: Raj Raghunathan: Happiness Guru

Raj Raghunathan is a Professor of Marketing at the McCombs School of Business at the University of Texas.  He has also become an expert in the field of happiness.  He is the author of the book If You’re So Smart, Why Aren’t You Happy.  He teaches an MBA course on happiness as well as a class on the online learning platform Coursera entitled: A Life of Happiness and Fulfillment.  Over 170,000 students have taken the course and it’s consistently ranked as one of the top ten courses (amongst thousands of others).

 

Some interesting insights from this episode:

  • If you’re so smart, why aren’t you happy?
  • Why do we devalue happiness even though we know how important it is?
  • How fear of failure often prevents us from trying things we know would make us happier.
  • How having wealth and status and success can make us happy, yet the pursuit of those things can make us miserable.
  • Once you stop comparing yourself to others and just focus on immersing yourself in your work (or activity), you’ll actually increase your likelihood of success.
  • How we can rewire ourselves to increase our level of happiness.

 

If you’re so smart, why aren’t you happy?  This counterintuitive philosophical question is the aptly named title of Raj’s quintessential book on happiness.  Generally speaking, smart and successful people are pretty good at setting goals and achieving them.  So one would think that if they are able to set goals around wealth and success, they could just as easily set goals around happiness.  But more often than not, they don’t.

So why exactly do we devalue happiness?  Why is it that despite knowing intuitively how important happiness is, we rarely prioritize it?  One reason is what Raj refers to as “Medium Maximization”.  That is, we focus on the means to the end (i.e. money, status) and not the end itself (happiness).  Since we think the money and success will naturally lead to happiness, we end up concentrating all our efforts on the money and success while forgetting about the very reason we were wanting it to begin with.  While the money and success may boost happiness levels initially, those feelings quickly subside in which case we need even greater levels of wealth and power to maintain those levels.  It’s a vicious cycle that repeats itself over and over.

We also have a difficult time articulating what happiness means to us.  And if we can’t visualize the goal in concrete terms, we don’t prioritize it.  So we end up prioritizing those things which are easier to measure (and easier to control) such as money and accomplishments.

Raj also points out that as humans, it’s in our DNA to seek superiority.  In fact, studies show that higher status does indeed enhance the quality of our lives and our happiness levels.  Yet, paradoxically, the actual pursuit of that higher status can backfire and cause us misery.  Tethering your happiness on being superior to others is ill advised.  Instead, if you focus solely on immersing yourself in your work (or hobby or activity), you’re much more likely to enjoy yourself and actually end up being more successful as well.  This “immersion” is what’s commonly known in positive psychology circles as “flow”.

So while we may have a better understanding intellectually why happiness is so elusive, how do we reverse course and become happier people?  Raj offers a few action items:

  • Do the things on a day to day basis that are meaningful and enjoyable. It doesn’t have to be work-related (although that’s ideal).  It can be tennis or guitar or gardening.  Anything that brings you joy.
  • Spend more time on personal relationships. Don’t take your friends and family for granted.  Your interactions with the people you care about in your life are as important as anything else.
  • Build habits that give an internal sense of wellness (i.e. exercise, meditation). Being physically and mentally healthy are essential ingredients to happiness.

As Raj reminds us of the cliché we all know too well, days and weeks will become months and years and next thing you know, you’ll be 70 and regretting your life.  So don’t wait another year or even another day.  Start today.  Take baby steps if you need to.  But take action.  Do something.  Anything.  After all, this is your life.  You deserve to be happy.