My career is an accident. It started when I set out to rediscover my passion and reignite a spark I’d lost — and that journey led me to the work I do now. If you know me from my books or my speaking, you know I’m fascinated by why people do what they do. What makes someone find joy and meaning in their life, or pursue something far greater than themselves? I started A Bit of Optimism to explore those ideas and expand my own perspective. This podcast is a trove of honest conversations, with p ...
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My career is an accident. It started when I set out to rediscover my passion and reignite a spark I’d lost — and that journey led me to the work I do now.If you know me from my books or my speaking, you know I’m fascinated by why people do what they do. What makes someone find joy and meaning in their life, or pursue something far greater than them…
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Ask Yourself "What If?" with Milk Bar Founder Christina Tosi
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47:44What if this podcast turned into a baking show? For Christina Tosi’s third visit to A Bit of Optimism, we decided to find out. So we headed to Milk Bar to make compost cookies from things in my own pantry and my favorite beer bread from scratch! Christina’s not just my best friend—she’s the founder of Milk Bar, host of Bake Squad on Netflix, a cook…
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Revisited: Love Is Not Enough with couples therapist Shawn McBride
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47:49We're taking some time off to bring you even more episodes of A Bit of Optimism that you're going to love! In the meantime, we're revisiting some of our favorite episodes, like this one with couples counselor Shawn McBride. Relationships are hard. No matter how much we like, respect, or love someone, conflict seems inevitable. But even as we fight …
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Revisited: The Secret to Happiness with Harvard professor Robert Waldinger
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45:30We're taking some time off to bring you even more episodes of A Bit of Optimism that you're going to love! In the meantime, we're revisiting some of our favorite episodes, like this one with Harvard professor Robert Waldinger. We all want to live a happy life. But what does the research say about how to achieve it? For more than 86 years, researche…
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Where Is Simon Going? with journalist Cal Fussman
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50:18Sometimes in life, we must stop and ask ourselves, “Where am I you going next?” Other times, it’s more fun to do a podcast takeover. No one has ever interviewed me quite like Cal Fussman. Cal has a gift – he pulls things out of you that you didn’t even know were there. A prolific Writer At Large for Esquire, Cal has interviewed legends like Muhamma…
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The Cure for Nihilism with professor Suzy Welch
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34:37Sometimes in life, we choose the wrong path. When we feel like we're living a lie, it's hard to know what to do next. That’s where Suzy Welch comes in. She’s obsessed with helping people create lives worth living. A professor at NYU’s Stern School of Business, Suzy teaches a popular class called “Becoming You,” where she takes students down a bruta…
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(PART 2) The Climb Out of Pain is Taller Than Everest with National Geographic photographer Cory Richards
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39:47*Please note: At 9:01, Simon and Cory have a discussion about suicide. What happens after we attain success and glory? Where do you go when there's nowhere left to run from yourself? In Part 2 of my conversation with Cory Richards, Cory explains why reaching the summit of Everest marked the beginning of a long, painful fall from grace. After his tu…
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(PART 1) The Climb Out of Pain is Taller Than Everest with National Geographic photographer Cory Richards
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47:27What happens when we reach the top? There’s only one place to go. Cory Richards has scaled the world’s highest peaks and fallen to life’s lowest lows. An acclaimed mountain climber, photographer, and filmmaker, Cory has literally reached the top of the world. He climbed Mount Everest with no supplemental oxygen, became the first American to summit …
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Find Your Allies Fast with philanthropist Melinda French Gates
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38:35Change happens to all of us whether we choose it or not. What’s the best way to go through transition, especially when it’s something we didn’t want? Melinda French Gates has seen her fair share of big transitions. A philanthropist, author, and champion for female empowerment, she spent decades building the Gates Foundation into one of the mighties…
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Who Are You, Really? with journalist Maria Shriver
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41:41We often define ourselves by what we do or who we are to other people. But at our core, who we are is often something much deeper, and sometimes wildly different, from the version that the world sees -- or projects onto you. Maria Shriver was born into the legendary Kennedy and Shriver families, arriving with a script already written for her—an ide…
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The Search for Self-Love with podcaster Lewis Howes
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51:15Self-love is never as easy as we think. Is it possible to fall in love with ourselves the way we fall for other people? Lewis Howes knows that learning to like yourself, let alone love yourself, can take decades. After surviving a traumatic childhood, Lewis spent years working on himself to try and understand what it takes for human beings to achie…
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Revisited: Why Awkward Is Awesome with psychologist Ty Tashiro
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31:51A Bit of Optimism is on hiatus this week, so we’re revisiting one of our favorite conversations! In this episode, Simon talks with psychologist Ty Tashiro about social awkwardness and why being awkward can actually be a superpower. ***** Awkwardness gets a bad rap. But being awkward is often an indicator that someone has extraordinary. Psychologist…
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Does Gender Change How We Lead? with Retired Colonel DeDe Halfhill
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40:39Is there such a thing as female leadership? Or is gender not a factor? DeDe Halfhill would say yes and no. A retired Air Force colonel, Dede spent 20 years in the military, where she advised some of the military’s most powerful leaders during the War in Iraq. She was often the only woman in the room for weeks on end. And while DeDe found the princi…
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The Myth of the Perfect Meditator with podcaster Jay Shetty
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50:25We turn to ancient philosophies to help us cope with the stress of modern life. But what if ancient wisdom could use some help from the modern world? Jay Shetty has made it his life’s work to make wisdom, peace, and purpose available to everyone. After living as a monk for 3 years, he left his monastic lifestyle with the hope of spreading what he l…
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When Your 'Flaw' Becomes Your Edge with Comedian Hasan Minhaj
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44:43To recognize your own talent takes time and self-awareness. But to find the courage to pursue it? That often requires a spark of inspiration from someone else. For Hasan Minhaj, that spark came from an unexpected trio—a teacher, a roommate, and Napster. A former correspondent on The Daily Show, Hasan’s natural gift of gab allowed him to build a wid…
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Humble Leaders Lead Better Teams with Retired Navy SEAL Jocko Willink
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42:07Most 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 mos…
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A Sweet Conversation About Dying with Death Doula Alua Arthur
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45:22Death 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…
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The Secret Art of Micromanagement with Airbnb CEO Brian Chesky
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44:06People 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…
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You Are More Like Grammy-Winner Jacob Collier Than You Think
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57:33To 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 …
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Kids (And Employees) Know More Than You Think with Dr. Becky Kennedy
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42:42Parenting 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 …
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Spite Is The Greatest Motivator with Watch Duty founder John Mills
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39:02When 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…
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The First Steps to Reducing Your Anxiety with author Mel Robbins
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54:35Life 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 be…
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The Cure for Loneliness with U.S. Surgeon General Vivek Murthy
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46:39Loneliness 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 lett…
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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 …
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Should You Work With Your Friends? with my friend Will Guidara
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49:26They 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 own…
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The Secret to Happiness with Harvard professor Robert Waldinger
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45:30We all want to live a happy life, but what does research say about how to actually achieve it? For more than 86 years, researchers at Harvard University have been trying to answer that question. In one of the longest-running and most comprehensive studies of human happiness, Harvard tracked 724 teenagers through every stage of their adult lives sin…
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The First Steps to Find Love with Matthew Hussey
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48:48Finding love is a journey. We might take some wrong turns along the way. Matthew Hussey helps people find love, and sometimes, redefine their relationship with love. Matthew is a dating coach who balances practical advice about the art of attraction with the importance of centering our own sense of self in our search for love. Starting as a teenage…
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Dr. Mark Hyman: To Live Longer You Need...
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48:04Close friends are the best thing for your health. Friendship, it turns out, is one of life’s best medicines. If you don’t believe me, believe Dr. Mark Hyman. Mark is one of the leading voices in the functional medicine movement, which is all about taking a holistic approach to our health for natural healing and preventing disease. The smallest chan…
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Alexis Ohanian: Why I Left Reddit and Why Greed Can Inspire Good
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1:04:18In 2020, Reddit co-founder Alexis Ohanian resigned from his own company in protest. After 15 years building Reddit into a social media juggernaut, why leave? The answer is values. Alexis is the kind of entrepreneur and investor who believes that integrity and long term profits go hand in hand. It’s the reason he started his new company 776, allowin…
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What can we learn from a rural school in Kenya? with principal Carol Moraa
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39:58Kenya's Maasai Mara is rugged, beautiful, and tough. Values are everything for the people who live in this rural countryside, On a trip to Kenya, I had the opportunity to visit The Mara. The intelligence and grit of the young people there blew me away! I met incredibly driven young women determined to uplift their families from poverty. Carol Moraa…
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Peace Is A Process with negotiation expert William Ury
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42:07Peace is a process, not an outcome. It's a process that must begin with understanding the other side. Few people on this planet have as much experience making peace as William Ury. William spent decades as a peace negotiator, resolving the world's most intractable conflicts — from avoiding nuclear catastrophe in the Cold War to mediating ethnic ten…
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Creating Astonishment with Chicago Bears CEO Kevin Warren
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56:08Astonishment. A feeling of amazement so powerful you have to stop in wonder. As President and CEO of the Chicago Bears, Kevin Warren's job is to astonish people with sports moments they'll never forget. A veteran executive of professional football, he's also served as COO of the Minnesota Vikings and Commissioner of the Big Ten Conference. For Kevi…
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A Lifetime of Leadership with President Joe Biden
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32:52Leadership is deeply personal. As people change, the way they lead has to change, too. Few leaders have navigated as much change as Joe Biden. He was elected to the Senate at 29 and will end his time as President at 82. The number of things he has witnessed and been a part of over the course of his career is remarkable. His journey has been shaped …
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Revisited: How To Be A Friend with chef and entrepreneur Christina Tosi
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39:25Friends can help us get through life’s toughest moments. But a true friend remembers to smile about the good times. That’s why I wanted to revisit my conversation with the founder and CEO of Milk Bar, host of Netflix’s Bake Squad, and author of several cookbooks including Dessert Can Save the World, my dear friend Christina Tosi. Christina is the t…
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Revisited: Molly's Game with Molly Bloom
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49:30Some people’s life stories are too crazy not to tell. So today, we’re revisiting one of my favorite episodes, my conversation with Molly Bloom. Her story is so riveting it's no surprise it became a star-studded Hollywood film. After her Olympic dreams were dashed, Molly wound up running an illegal, high-stakes poker game where hundreds of millions …
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Revisited: We Cannot Heal Alone In The Loneliness Epidemic with Rabbi Sharon Brous
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34:12Grief can paralyze us. Most of us aren't given a manual about how to comfort someone grieving or how to ask for help with our own pain. That's why I wanted to revisit one of my favorite conversations, with Rabbi Sharon Brous. I talked with her about being present to someone else's pain and what it means to heal together in the loneliness epidemic. …
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Confident Ignorance with rapper, novelist, and filmmaker Logic
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59:43Vision, not skill, is the heart of creativity. But when a creative vision gets too big for one person, the key is to ask for help. Logic is a platinum-selling rapper who’s made waves in the hip hop world. After a troubled childhood, he started making music with a positive, introspective message, eventually receiving nominations for two Grammy Award…
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Wealth Is Togetherness with community organizer Kennedy Odede
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36:22The slums of Kenya are a tough place to grow up. Stealing a mango could get you killed. Kennedy Odede grew up in Kibera, Africa's largest urban slum. A street kid at age 10, he dreamed of factory work for 10 cents a day. But after stealing a mango out of hunger, a stranger's single act of kindness changed the course of his life. Today, Kennedy is t…
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Landing Moonshots with Google's Innovation Chief Dr. Astro Teller
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44:40Before Elon Musk rebranded Twitter, X was already in use — at Google. Google X was Google's secret research lab, where Google's most imaginative ideas came to life. As CEO and co-founder, Astro Teller's job is to harness X's wildest, most futuristic technology to solve the world's hardest problems. The same "moonshot factory" that created Google Br…
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Creativity Is Connection with poet IN-Q
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37:34Business and poetry usually don't mix. But vulnerability has the power to bring teams together. Poet IN-Q has found an unlikely audience in business. A slam poetry veteran and accomplished songwriter, companies invite IN-Q to help strengthen their cultures. He works with teams to connect on a deeper level, using poetry to share something human. As …
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The Smell of Memory with scent designer Dawn Goldworm
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44:56Our sense of smell has the deepest tie to emotion and memory. But it's also the most overlooked. In business, that's a giant missed opportunity. Dawn Goldworm knows how to use scent to evoke emotion and create loyalty. From Lady Gaga to Ferrari to books, Dawn designs signature fragrances that allow customers to connect with brands in a more meaning…
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Mastery is an Infinite Game with performance psychologist Mike Gervais
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41:40Fierce competition can lead to burnout. How do we train ourselves to maintain excellence without giving in to the pressure to perform? High-performance psychologist Mike Gervais has a solution. He calls it mastery. Mike's approach to mastering our thoughts and emotions has helped Olympians win gold medals, the Seattle Seahawks win the Superbowl, an…
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Breaking Tradition with cellist Anastasia Kobekina
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38:09Classical music could use a little disruption. For Anastasia Kobekina, that means playing outside of its rigid forms. An accomplished soloist, Anastasia has played with prestigious orchestras all over the world. She also bangs on her cello, improvises with Vivaldi, and sings. I was thrilled to sit down with Anastasia to discuss her musical experime…
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How to Breathe Out Fear with freediver Li Karlsen
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46:51Courage isn't about bravado. It's about staying calm. Li Karlsen knows a lot about staying calm under the most inhospitable conditions. One of the most accomplished freedivers in the world, Li is a record-holding champion at holding her breath and diving hundreds of feet below the ocean's surface. I wanted to ask Li what freediving has taught her a…
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More Thinking About Thinking with Brené Brown and Adam Grant: Part Two
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38:10In Part 2 of our conversation, Brené Brown, Adam Grant, and I continue our journey of out loud self-reflection. We discuss identifying our values, the two types of narcissists, explanation-based parenting, and exercising judgment over our own judgment. Listen to Part 1 here or wherever you listen to podcasts. This...is A Bit of Optimism. For more o…
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Thinking About Thinking with Brené Brown and Adam Grant: Part One
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42:49To become more self-aware, sometimes you need a friend. Two friends is even better. Brené Brown and Adam Grant swing by the podcast for one of our trademark conversations with no plan. It turns into a deep dive about knowing our selves and how self-reflection is sometimes best done with others. What's a little metacognition between friends? This...…
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The War On The Young with Professor Scott Galloway
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1:02:20Building wealth is an unequal pursuit. Scott Galloway believes no one is getting more screwed financially than young people. Scott argues what the U.S. is doing to the economic future of its youth is nothing less than a war on the young. The massive transfer of wealth from young to old is a topic he explores in his new book The Algebra of Wealth. I…
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Moral Courage with Diane Foley, mother of executed journalist James Foley
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30:47Seven years after ISIS killed her son, Diane Foley met with one of his killers. Somehow, she was able to find the humanity in her son's murderer. ISIS held journalist James Foley hostage for 2 years before publicly executing him in 2014, when they uploaded a YouTube video of James's beheading. After her son's murder, Diane Foley started The Foley F…
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Humble Confidence with veteran and entrepreneur Blake Hall
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27:55Humility stems from confidence. Confident leaders can admit when they're not the smartest person in the room. Blake Hall exemplifies the type of leadership we need more of in business. A former Army Ranger, Blake was awarded the Bronze Star for leading his platoon in combat during the Iraq War. Now he's the CEO and co-founder of ID.me, a digital wa…
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The Ultimate Infinite-Minded CEO with Trek Bicycle CEO John Burke
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24:32The jump from $250 million to $2 billion in revenue doesn't happen overnight. Over 25 years, John Burke transformed Trek Bikes into a global powerhouse — one mom-and-pop bike store at a time. The key to John's success is simple but powerful. Create value for others first, and you too shall be rewarded. John and I discuss why the best way to win isn…
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