Leadership, AI & Chasing Greatness with Rajeev Kapur | The Jason Wright Show

What does it mean to lead well when your whole team has access to the same AI? In this episode, Jason sits down with Rajeev Kapur, CEO of 1105 Media, former Dell executive, MIT-certified AI advisor, and bestselling author, to talk about leadership, entrepreneurship, and how leaders should set the playbook for using AI in their organizations.

Rajeev shares how a 100%-commission job at Gateway 2000 in South Dakota launched his career, how 12 years at Dell took him to Asia, and how he got through COVID...

Episode description

Wade Myers grew up in the Badlands of western North Dakota in a Mennonite home with no electricity, no indoor plumbing, and no telephone. He was selling door to door at age nine. He went on to become an Army Ranger, served in the Gulf War, earned an MBA from Harvard Business School, and built a career as one of the most successful entrepreneurs and investors around.

In this episode of the Texas Titans podcast, Jason Wright and Wade talk about why he left corporate America, how a handshake deal with a mentor...

The Jason Wright Show — Jacob Baadsgaard: How to Become (and Hire) the Indispensable Marketer

On the day his new book The Indispensable Marketer launches, Jacob Baadsgaard joins Jason for something closer to a coaching session than an interview. Jacob is the founder and sole owner of Disruptive Advertising. Over 14 years the agency has served 2,000+ companies, managed more than $3 billion in ad spend, and generated a couple hundred million in revenue. Jacob explains why founders and their marketers so often end up pointing fingers at each other. He walks through the math every CEO owes their marketing team, an...

The Key to Happiness: Trade Expectation for Appreciation

What if one of the biggest obstacles to happiness isn’t what you’re missing—but what you’re expecting?

In this episode of The Jason Wright Show, Jason shares a simple mindset shift that has had a profound impact on his life: trading expectation for appreciation.

For years, Jason’s high expectations pushed him to achieve more—but they also made it difficult to appreciate the career, relationships, opportunities, and life he already had. At 51, he’s learning that ambition and gratitude don’t have to compete...

So Good They Can’t Ignore You: Paul Rand

What happens when you become so good at your craft that the most demanding people in the world come looking for you?

In this episode of The Jason Wright Show, Jason launches a new series inspired by Steve Martin’s famous career advice:

“Be so good they can’t ignore you.”

The first profile is legendary graphic designer Paul Rand—a man whose name you may not immediately recognize, but whose work you almost certainly do.

Born Peretz Rosenbaum in Brooklyn in...

When Self-Reliance Becomes Self-Sabotage

Being self-reliant is usually considered a strength. But what happens when independence becomes so deeply ingrained that you stop asking for help, stop expressing what you want, and convince yourself that you don't need anyone?

In this episode of The Jason Wright Show, Jason reacts to performance coach Joe Hudson's discussion of self-reliance and gets unusually personal about how the pattern has shown up throughout his own life.

Hudson describes self-reliance as the belief that you have to handle everything yourself—a pattern that can develop when, as a ch...

Stop Wasting the Life You Already Have

What if most of the things causing you stress, anxiety, and unhappiness aren't actually problems yet?

In this episode of The Jason Wright Show, Jason explores a powerful idea from Naval Ravikant: much of human suffering doesn't come from what is actually happening to us—it comes from the stories, expectations, fears, and desires we create around what is happening.

Drawing from Naval's conversation with Chris Williamson on Modern Wisdom, Jason examines what it means to stop manufacturing unnecessary suffering, become more selective about what we wa...

Stop Doom Scrolling: Replace the Habit, Don’t Just Remove It

In this episode of The Jason Wright Show, Jason continues his digital detox series with a practical strategy for breaking the doom-scrolling habit.

Simply deleting Instagram, putting down your phone, or promising yourself you’ll scroll less usually isn’t enough. When you remove a habit, you create a vacuum—and something will eventually fill it.

The question is: Will you deliberately choose what replaces it, or will your brain choose the easiest source of stimulation available?

Jason explores the idea of...

Your Brain Is Wired to Underperform: Why Excellence Requires an Override

What if the biggest thing standing between you and your potential isn’t a lack of talent, discipline, or motivation—but your own brain?

In this episode of The Jason Wright Show, Jason explores the idea that the human brain is designed to conserve energy, manage risk, and keep us from pushing too far. That protective mechanism may be useful for survival, but it can also become an internal governor that convinces us we’ve reached our limit long before we actually have.

Draw...

The Greatest Productivity Hack I’ve Ever Learned: How to Get Into Flow

What if you could get more meaningful work done in 45 minutes than you normally accomplish in several hours?

In this Monday Morning Mentor episode of The Jason Wright Show, Jason explores one of the most powerful productivity tools he’s learned: the flow state.

After a conversation with one of his mentees reminded him of his previous episodes on flow, Jason found himself experiencing it firsthand—sitting down, eliminating distractions, focusing on a single problem, and accomplishing an enormous amount of wor...

After the incredible response to the first Dad Boss episode, Jason Wright and Abby Neilson are back — this time answering questions submitted by listeners.

And nothing is off limits.

From dating in the age of social media to marriage, singleness, faith, relationships, communication, and figuring out what actually matters in a partner, Jason and Abby bring two very different generational perspectives to the conversation.

Jason shares lessons from marriage and raising daughters, including why small rituals can become some of the most meaningful parts of a relationship. Abby offers the perspective of a yo...

Don't Optimize Yourself to Death

Jason digs into why our obsession with biohacking and longevity can quietly steal the life we're trying to extend — and how to find the balance between pursuing excellence and just plain living.

Episode Summary

Jason opens with the inspiration for this episode: an interview with a couple who run a precision medicine clinic in Basel, Switzerland, and authored a new book called Unlongevity (that interview airs on The Healthy CEO around August 16th). Their premise — that our pursuit of a longer life can come at the cost of actu...

The Jason Wright Show — Dr. Noah St. John: Tame the Caveman in Your Brain

Dr. Noah St. John returns to The Jason Wright Show to break down his newest framework: taming the "caveman in your brain" — the 200,000-year-old survival wiring that's quietly sabotaging how founders, sales teams, and employees respond to AI.

Noah explains why the internet revolution took seven years to reach its zenith, while AI took seven months — and why that speed is exactly what's triggering fear and paralysis inside organizations. He walks through his four "caveman types" (the Chief, the Spark, the Keeper...

The Competitive Advantage of Saying "I Don't Know"

What if the greatest competitive advantage in your career isn't intelligence—but intellectual humility?

In this Monday Morning Mentor, Jason Wright explores one of the most overlooked leadership traits: the willingness to admit you might be wrong. While most people waste energy defending their opinions, history's greatest leaders built their success by questioning their own assumptions.

Drawing lessons from Abraham Lincoln, Charlie Munger, and Ray Dalio, Jason explains why the fastest learners become the strongest competitors and how adopting a "white belt mindset" can accelerate yo...

What if the best career advice you ever received came from someone who cared about more than your résumé?

Welcome to the first episode of Boss Dad, a new series on The Jason Wright Show where I sit down with young professionals for honest conversations about careers, relationships, ambition, integrity, faith, failure, and figuring out adulthood.

My first guest is my former employee and current mentee, Abby Neilson.

About a year ago, Abby was a recent college graduate struggling to land her first real job. A phone call that was originally supposed to...

Go Lay Your Bricks: Staying Busy and Creating to Fight Anxiety and Depression Jason Wright, host of The Jason Wright Show and The Healthy CEO, shares that staying busy and creating something can help fight anxiety and depression. He references Winston Churchill’s lifelong struggle with depression, which Churchill called the “black dog,” and explains how Churchill coped by keeping occupied through painting and even laying bricks to engage his hands and mind. Wright relates this to his own experience of getting into funks and says creative projects like making a podcast or short video help him avoid doom scroll...

Pax Prentiss spent ten years addicted to heroin, cocaine, and alcohol before discovering that addiction was not the root problem—but a symptom of deeper emotional pain.

Today he is the co-founder of Passages Malibu, where thousands have recovered through individualized, holistic treatment rather than traditional addiction models.

Jason and Pax discuss:

Contact Pax for a free consultation

Happy 250th America. I LOVE you!

Digital Minimalism Update: Add Friction to Break Doom-Scrolling Jason Wright shares an update on his digital minimalism effort to reduce dependence on social media and improve focus and cognitive ability, inspired by Cal Newport’s work. He deleted Instagram and YouTube from his phone (leaving them on his iPad), finding the main downside is losing easy interaction with friends via Instagram DMs, not missing the entertainment. Benefits include reading more via Apple News and books (including Ian Fleming’s Casino Royale and Dostoevsky) and feeling “down-regulated” from the urge to scroll; after reinstalling Instagram briefly for a family trip, he felt...

Self-Control and Divine Masculinity Jason discusses self-control as a vital personal asset, focusing especially on masculinity, drawing on ideas from Robert Greene and Jordan Peterson. He frames self-control as an ancient and biblical principle, citing Galatians 5:22–23 and Jesus’ examples in the wilderness and the teaching to “turn the other cheek,” which he interprets as choosing restraint despite having the power to dominate, not being a doormat. He compares this to martial artists who possess capability without seeking fights, and shares workplace and childhood examples showing how losing emotional control gives others leverage and damages credibility. He argues the most admirabl...

Weekend Review: ‘80s/’90s Nostalgia, Simpler Times, and the Luxuries We Took for Granted Jason Wright reflects on nostalgia for the ’80s and ’90s, noting that older music is popular again and arguing that life felt simpler before today’s intense political division. He cites a Vanilla Ice interview about performers dropping out of a White House 250-year celebration over Trump and praises Ice’s wish to return to a fun, non-political era. Using a BuzzFeed list about “luxuries” from the ’80s, Jason recalls special-occasion restaurant meals (like Red Lobster), traveling to another town just to go to McDonald’s, long-distance pho...

00:00 Welcome to Monday Morning Mentor 00:20 The Future Self Concept 00:55 Living Proof of Past Discipline 01:44 Understanding Delayed Gratification 02:16 Financial Discipline and Dave Ramsey 02:56 Finding Your Art 03:54 Making Better Daily Decisions 04:45 Balancing Present and Future 05:11 Looking Back with Gratitude 05:29 Reflections on Getting Older 06:29 Write Yourself Notes 07:32 Finding the Balance 08:42 Final Thoughts and Motivation

00:00 Welcome to Monday Morning Mentor 00:20 The Future Self Concept 00:55 Living Proof of Past Discipline 01:44 Understanding Delayed Gratification 02:16 Financial Discipline and Dave Ramsey 02:56 Finding Your Art 03:54 Making Better Daily Decisions 04:45 Balancing Present and Future 05:11 Looking Back with Gratitude 05:29 Reflections on Getting Older 06:29 Write Yourself Notes 07:32 Finding the Balance 08:42 Final Thoughts and Motivation

Write Your Ideal Self: Lessons from “Rooster” and Monday Morning Mentorship Jason Wright hosts Monday Morning Mentor and shares an idea inspired by the HBO show “Rooster,” in which Steve Carell’s character says he writes for a hero who does what he wishes he could do. Jason encourages listeners to visualize and write down their own “ideal self” (health, relationships, parenting, partnership, presence) as defined by them, aligning with his motto “improve always in all ways” and his Vitruvian Project concept of becoming a more well-rounded human. He suggests journaling or story-form descriptions of an ideal day and asks, if you’re no...

Week in Review: Comprehensive Health Testing, Dopamine in an Age of Abundance, and Marijuana Reclassification Concerns Jason Wright opens with reflections on how fast the year is going and a personal tradition of watching The Holiday on June 25, then shares a clip from his conversation with John Goldman, founder of Rebel Health, about how comprehensive functional-medicine testing (DEXA, VO2 max, A1C and other labs) revealed Goldman was pre-diabetic with visceral fat, fatty liver disease, and other risk markers, prompting Wright to urge listeners to get thorough testing beyond standard annual checkups. He next introduces researcher Anna Lembke on...

Consume Less. Create More.

Low Stakes, Big Try: Why You Should Start (and Stop Making It Do-or-Die) Jason Wright shares a lesson from trying to relearn guitar using the GuitarTuna app: when he stopped treating practice as a performance and gave himself permission to fail, relax, and just learn, he unexpectedly hit a personal best. He connects this to a Will Ferrell interview about pursuing comedy with a safety net and the role of luck, plus a similar story about Stevie Nicks being encouraged to try music for four years before committing to college. Drawing on Carol Dweck’s mindset work and an ex...

Week in Review: Fat, Exercise Snacks, and Outsourcing Your Brain to Tech Jason Wright introduces the first Week in Review format, sharing clips and takeaways from recent conversations. From Dr. Jerry Nixon, he emphasizes that excess body fat is an active, harmful gland linked to inflammation, atherosclerosis, cancer, dementia, heart disease, bone and joint degeneration, and that Americans often live long lives with chronic disease. From Dr. Rhonda Patrick, he highlights “exercise snacks,” including structured vigorous bursts (about 1–10 minutes, reaching ~80–85% max heart rate) and unstructured vigorous intermittent lifestyle activity like fast stair climbs or brisk tasks; cited VPA research suggests...

Even Big Mama Is Using AI: Jason Wright’s Take on Adapting to the AI Revolution Jason Wright opens with a story about his wife’s aunt “Big Mama” posting an AI-altered senior photo of his sister-in-law on Facebook, using it to introduce his perspective on AI and why it’s now unavoidable. He reflects on decades of tech change—from the Commodore 64 and DOS terminals to pagers, early cell phones, BlackBerry, and AOL—then argues people should view AI as “me and AI,” not “me or AI.” He advises workers worried about displacement to befriend AI, start with tools like Gemini and...

Mike Stohler on Creative Real Estate, Syndications, and Boutique Hotels in Spain Jason Wright interviews real estate investor Mike Stoler, who built a portfolio spanning multifamily and hotels, including boutique castle properties in Spain. Stoler shares how Rich Dad Poor Dad and even a bad seminar sparked his start, early failures buying seller-financed homes from a university due to poor due diligence, and later lessons about inspections, leases, and learning operations by working for a property management company. They discuss creative financing (seller financing, assumptions), partnering and structuring deals via LLCs, joint ventures, and syndications with general and limited...

Stop Smoking Weed: The Cognitive Cost No One Wants to Talk About | Monday Morning Mentor In this Monday Morning Mentor follow-up on getting smarter, Jason argues that peak cognitive health matters more than ever amid the AI information onslaught and pleads with listeners to stop smoking weed, criticizing how frequently marijuana use is portrayed as normal or funny in shows and films like Your Friends & Neighbors, This Is Where I Leave You, Sam and Kate, and Love, Sarah. He says legalization doesn’t make cannabis harmless, takes issue with prominent pro-weed voices, and cites 2025 research summaries describing links between he...

The Psychology of Leadership with Sebastien Page: Listening, Strategic Quitting, and Long-Term Thinking Jason Wright interviews Sebastien Page, T. Rowe Price’s Head of Global Multi-Asset and CIO overseeing $500+ billion, about his book The Psychology of Leadership and the mindset and habits behind effective leadership. Page argues leadership is often counterintuitive: listening can matter more than communication; quitting—like selling an investment or stopping a failing project—is harder than persistence; and stress is inevitable but can be used as performance fuel. They discuss goal-induced blindness (including Everest examples), the importance of long-term thinking and meaning (the “three bricklayers” analogy...

Monday Morning Mentor: Focus on What You Can Control Jason Wright discusses a New York Magazine article by Xochitl Gonzalez that uses renewed nostalgia for smoking to express a cynical, nihilistic “nothing matters” reaction to a “deranged year,” framed around political events and a belief that the future is too bleak to justify good habits. Wright argues this mindset shows up in everyday life when people give up on health, appearance, and discipline because they feel powerless over society and current events. He shares a lesson from a former manager about concentrating on the “circle” of things you can control and...

Monday Morning Mentor: 10 Parenting “Don’ts” for Raising Well-Adjusted Kids In this Monday Morning Mentor episode, Jason Wright reflects on parenting his daughters Ryland (26, newly married) and Abby, sharing a list of “not to do” parenting lessons shaped partly by his own experience with conditional love growing up. He advises parents not to make love conditional, not to guilt-trip kids about costs or sacrifices, and not to praise intelligence over effort to avoid a fixed mindset (citing Carol Dweck’s work). He warns against spoiling children and recommends teaching delayed gratification through goals or matching contributions. Other “don’ts” include letting ki...

A Plea to Get Smarter: Brain Fitness, Reading, and Escaping the Attention Economy Jason Wright asks listeners to intentionally “get smarter” by strengthening their ability to reason, focus, and tolerate boredom, arguing society is regressing in communication and thinking and that this correlates with widening wealth gaps. He warns that “free” digital services (Pluto TV, Gmail, TikTok, Instagram, Facebook) make users the product by monetizing attention, and encourages replacing doom-scrolling with reading and other “brain fitness” habits. Citing books and thinkers like Greg McKeown (Essentialism), Arthur Brooks (The Meaning of Your Life), and Cal Newport (Deep Work, Big Questions), he frames re...

After his daughter’s wedding, Jason shares advice from the Bible studies they held leading up to it: to maintain a happy marriage, treat your spouse as though they already are the man or woman of your dreams, because people tend to live up to how they are treated. He extends this idea to all relationships and to personal growth through identity-based habits—acting like the healthier, smarter, or more successful version of yourself makes it more likely you’ll become that person. Jason describes how he cherishes his wife, Jim Lynn, with daily affection and small acts like making...

Dr. Sharon Spano is a transformational executive coach, business strategist, and thought leader specializing in human potential and high-impact leadership. With more than 25 years of experience in corporate and private business settings, she works with CEOs, entrepreneurs, and leadership teams to uncover the hidden barriers that limit growth and fulfillment.

She holds a PhD in Human and Organizational Systems and is a certified Integral Professional Coach, bringing a unique blend of science, systems thinking, and personal development to her work. Dr. Spano is the creator of the Potential Unleashed™ framework and the author of The Pursuit of Ti...

Never Complain, Never Explain

Jason reflects on the quote “never complain, never explain,” which he heard from Robert Greene and believes is attributed to a former British Prime Minister, and describes how he researched it and recognized his own habits of complaining and explaining. He argues that complaining is exhausting, people don’t care to hear it, and it can enlarge problems by reinforcing a negative mindset, noting a perceived correlation between frequent complaints and more aches and pains. He also commits to stopping unnecessary explanations about his unconventional, project-based work and podcasting, emphasizing he doesn’t owe anyo...

JB Glossinger on Reducing Cognitive Load, Saying No, and Building Systems for Consistent High Performance Jason Wright interviews performance coach and MorningCoach founder JB Glossinger about building systems to reduce cognitive load and decision fatigue for entrepreneurs facing information overload. JB shares how early academic struggles pushed him to create a productivity framework rooted in the “six things” prioritization method, later expanded into a mission-vision-values cascade down to goals, projects, and tasks. He emphasizes simplifying, using data for business decisions, and prioritizing lifestyle choices, including learning to say “no,” even to a potential $100M corporate deal, to protect his desired...

Monday Morning Mentor: Never Drink at Work Events Jason Wright introduces a new “Monday Morning Mentor” segment on the Jason Wright Show and shares a core lesson: never drink at work events. He recounts being 23 at his first convention, drinking free alcohol, and then driving colleagues—including a vice president—while intoxicated, followed by intense next-day regret and anxiety. He describes repeatedly replaying conversations after professional outings, the peer pressure and judgment non-drinkers can face, and an embarrassing incident getting sick in a vice president’s hotel room. Wright explains that setting personal rules (e.g., no weeknight drinks, no work-ev...