A Bit of Optimism

Latest Episodes:

Humble Leaders Lead Better Teams with Retired Navy SEAL Jocko Willink Feb 25, 2025

Show notes

Most people believe the only way to lead is to become the best at something. But what if great leadership means admitting you’re not the best at anything?

Jocko Willink believes the secret to his greatest achievements come down to one thing – humility. A retired Navy SEAL commander, Jocko served 20 years in the U.S. military, leading one of the most decorated special operations units through combat in the Iraq War. A New York Times bestselling author, podcast host, and entrepreneur, he now teaches those in the civilian world the skills he learned from his time in the SEAL Teams.

This was my first time meeting Jocko Willink, and we discussed why new leaders should never try to prove their own competence and the difference between tyrannical and open-minded leaders.

This…is A Bit of Optimism.

For more on Jocko and his work, check out:

jocko.com

A Sweet Conversation About Dying with Death Doula Alua Arthur Feb 18, 2025

Show notes

Death is a word we like to avoid. We dance around the subject or use vague euphemisms to not hurt anybody. But what if being open about our deaths meant we could live happier lives?

That’s where Alua Arthur comes in. Alua is one of the most prominent death doulas in the country, which means it’s her job to help people die. She offers support to her clients and their families as they embark on their dying journey, tackling everything from financial planning and insurance policy to emotional support and grief.

When I sat down with Alua, I was prepared for a grim conversation. Instead, I was pleasantly surprised by her candor and good humor about dying. She shares with me how she made a career pivot from lawyer to death dula, the most interesting stories she’s heard from people on their death bed, and why thinking about our deaths is the key to living the way we wish to live.

This…is A Bit of Optimism.

For more on Alua and her work, check out: Going With Grace

The Secret Art of Micromanagement with Airbnb CEO Brian Chesky Feb 11, 2025

Show notes

People aren’t born great leaders. They learn to become great leaders.

For Brian Chesky, the learning never stops. As the co-founder of Airbnb, he had to transition from an impassioned entrepreneur with a brilliant idea into a CEO responsible for thousands of employees. To make the hard decisions necessary for Airbnb to survive the COVID pandemic, a cataclysmic event for the travel industry, Brian had to lean into the skills and thinking he’d learned and practiced for over a decade of leadership.

I’ve watched Brian grow as a leader for years, and so I was delighted to sit down with him for a conversation on what people get wrong about great leadership. He shares with me the difference between micromanagement and “eyes on” leadership, why leaders should fight the instinct to be liked, and why an existential crisis is the best thing to put a company’s values to the test.

This…is A Bit of Optimism.

For more on Brian and his work, check out:

airbnb.com

You Are More Like Grammy-Winner Jacob Collier Than You Think Feb 04, 2025

Show notes

To create something truly original, do we build something new or break what came before? Perhaps the answer is both—simultaneously.

Jacob Collier does exactly that. A brilliant songwriter and musician, he’s known for transforming his live audiences into massive three-part choirs, making music with the very people who attend his concerts. His album Djesse Volume 4 was nominated for Album of the Year at the 2025 Grammy Awards, alongside icons like Beyoncé, Billie Eilish, and Taylor Swift. Although Beyoncé's Cowboy Carter won, Jacob snagged his seventh Grammy for his rendition of "Bridge Over Troubled Water."

I sat down with him in a music studio a few days before the Grammys, surrounded by multiple pianos, and it was a joy to hear him play. Jacob’s approach to music—blending structure with spontaneity—offers insights into creativity that are as inspiring as his sound.

This…is A Bit of Optimism.

For more on Jacob, check out:

jacobcollier.com

Kids (And Employees) Know More Than You Think with Dr. Becky Kennedy Jan 28, 2025

Show notes

Parenting is the hardest job in the world—and it turns out, it’s also one of the best training grounds for leadership.

Dr. Becky Kennedy, aka the “Millennial Parent Whisperer,” became an essential voice for caretakers by offering practical, actionable parenting advice that resonated with millions during the pandemic. As a clinical psychologist and founder of Good Inside, she’s now helping parents build sturdy leadership skills that not only transform their homes but also their work lives.

In this conversation, Dr. Becky shares how understanding boundaries, emotional triggers, and big feelings can help us become more effective leaders. Whether you’re a parent or a manager (or both!), her insights will help you lead with more intention, connection, and confidence.

This… is A Bit of Optimism.

Check out Dr. Becky's work:

https://www.goodinside.com/

Spite Is The Greatest Motivator with Watch Duty founder John Mills Jan 21, 2025

Show notes

When the wildfires struck Los Angeles, turmoil quickly consumed the city. People were desperate for clear, reliable information—unsure of evacuation routes or how to track the fires as they spread in a history-making wind storm. Then, we found Watch Duty. This intuitive app became our lifeline.

The visionary behind the app is John Mills, a seasoned tech entrepreneur who created Watch Duty out of necessity after his own community in Northern California was repeatedly threatened by deadly wildfires. But John didn’t just build an app—he reimagined how business and philanthropy can intersect to solve real-world problems.

Watch Duty is a not-for-profit initiative that harnesses the power of technology and human talent, relying on volunteers to gather critical data from fire scanners and reporters to save lives. Despite its explosive growth, John has no plans to sell the app, because for him, the value isn’t in making money—it’s in using his skills to help others. In a world where many focus on getting rich, John is challenging us to rethink how we can use our talents to serve the greater good.

This...is A Bit of Optimism.

For more on John and his work, check out:

Watch Duty

The First Steps to Reducing Your Anxiety with author Mel Robbins Jan 14, 2025

Show notes

Life can feel overwhelming, especially when we're too drained to even get out of bed. So, how do we push through those days?

For Mel Robbins, facing this very question turned her life around. Struggling with $800,000 in debt and at rock bottom, she became obsessed with finding practical ways to regain control. Fast-forward to today, and Mel is a bestselling author and podcast host who has helped millions transform their lives. In her latest book, The Let Them Theory, she reveals how shedding the weight of others' expectations can help us live more authentically.

I sat down with Mel to dive into how we can take action when we're emotionally spent, why our need for control ties us to other people's opinions, and how giving others the freedom to be themselves allows us to align with our true values.

This…is A Bit of Optimism.

For more on Mel and her work, check out:

The Mel Robbins Podcast

and her book, The Let Them Theory

The Cure for Loneliness with U.S. Surgeon General Vivek Murthy Jan 07, 2025

Show notes

Loneliness has reached epidemic proportions. Where do we go to feel like we belong?

As the Surgeon General of the United States, Dr. Vivek Murthy has been a leading voice in bringing the loneliness crisis to light, stressing its devastating impact on public health. As his second term nears its end, he leaves behind a powerful reflection in his letter, My Parting Prescription for America and the World.

In an insightful conversation with Dr. Murthy, we delve into what it truly means to be healthy—not just physically, but emotionally and socially—and discuss why the pursuit of fame, wealth, and power often leads us further from what we really need.

This…is A Bit of Optimism.

To read the letter, visit this link: My Parting Prescription for America and the World

To learn more about Dr. Murthy, click here: vivekmurthy.com

Trevor Noah Makes My Brain Hurt Dec 17, 2024

Show notes

It’s our last episode of 2024, so I decided to invite comedian Trevor Noah on…to get as serious as possible.

Most Americans know Trevor as the former host of The Daily Show, a bestselling author, and a stand-up comedian. But his brand of humor isn’t just a barrel of laughs— it’s raw, witty, thought-provoking, and often makes you see the world in a whole new way.

In this conversation, we ditched the small talk (mostly) and went deep into the paradox of choice, the public's response to the murder of United HealthCare's CEO, and why the human experience might be defined by constraint. It will make you chuckle, think, and probably question everything all at once.

This...is a Bit of Optimism.

P.S. Come back and see us on January 7, 2025 for an all new episode. Until then, take care of yourself and each other.

For more on Trevor and his work, check out:

trevornoah.com

Should You Work With Your Friends? with my friend Will Guidara Dec 10, 2024

Show notes

They say business and pleasure don’t mix. But what about business and friends?

My dear friend Will Guidara is the perfect person to dive into this question because we're actively trying to get into business together. And, let's just say, it requires a lot of effort.

In addition to being someone I love, Will is a renowned restaurateur, known for owning and operating Eleven Madison Park, once named the best restaurant in the world. He’s also the author of the brilliant book Unreasonable Hospitality and a co-producer of the FX television series The Bear.

Will and I have worked together before, so I was excited to chat with him about turning friends into colleagues, the reality of friendship breakups at work, and why sometimes showing respect means we have to change the way we treat a friend.

This…is A Bit of Optimism

For more on Will and his work, check out:

Unreasonable Hospitality

The Art of Creating Fiercely Loyal Customers