Go to www.LearningLeader.com for full show notes

This is brought to you by Insight Global. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver.

My guest: Nicholas Thompson is the CEO of The Atlantic and former editor-in-chief of WIRED. He's the author of the best-selling book (and one of my favorites of the year), The Running Ground. Nick shares why great leaders must balance being decisive with staying open to being wrong, how to build teams that challenge your thinking without creating chaos, and why the most important skill for the next decade is knowing what questions only humans can answer.

Consistency Over Intensity Creates Results - If you go out there every day, six or seven days a week, and a couple days you push yourself really hard, you get faster. There's no two ways about it. If you don't do that, you don't get faster. It's a very good reminder that you can get a lot done if you just go and allot time to pushing yourself.

Recommendation letter written by the Stanford faculty about Nick's dad to be a Rhodes Scholar: "Scotty Thompson is the kind of young man that comes along only once in approximately ten years. I cannot recall ever having known a student who possessed the same combination of intelligence, creativity, energy, drive, and dedication. He has attempted more, achieved more, than anyone we have studied– including some who now hold high office. He is generally conceded among those who have observed the student body since World War II to be the outstanding leader of the era. I think it likely that in the entire history of Stanford campus life, he has had no near rival since Herbert Hoover as an undergraduate."

Also about Nick's Dad: Tracy Bennett, one of his graduate students, said, "He was flamboyant, gently endearing, annoyingly arrogant, piercingly intelligent, entertaining, and more. I'd never met a man, nor had a professor, who was clearly so brilliant and at the same time so precariously insecure."

His grandfather, Frank Thompson, placed second in the Southern California extemporaneous speaking contest held at Whittier College. First place was Richard Nixon.

Parenting — "Nothing makes me more worried about failure than parenting." "Parenting is suffused with regrets, confusion, and mistakes. But when I run by, I know my children are rooting for me to succeed with infinite love and enthusiasm."

Running hard... Pushing yourself. Why do it? "Discipline builds discipline. Discipline is cumulative."

Sometimes You Have to Trick Yourself - I ran 10:48 because the track was bigger than I thought, and I didn't realize how fast I was going. If I had known I was running at a 5:23 pace, I would've shut down. My body would've started to hurt. Sometimes you can't let yourself know what you're actually doing, or you'll get scared.

Hiring at The Atlantic - The people he hires at The Atlantic share four must-have attributes: A spirit of generosity. A force of ideas. They're relentlessly hard workers. And they have an edge: an anxiety about getting great work done. That last one stuck with me. The best people aren't just talented... They're driven by a productive anxiety to do work that matters.

Becoming CEO of The Atlantic: The Search & Selection: The Atlantic conducted a yearlong search after President Bob Cohn left in fall 2019. When owners Laurene Powell Jobs and David Bradley announced Thompsont in December 2020, they said "Nick is singular; we've seen no one like him" and that he brought "a surround-sound coverage of relevant experience."

Move at an Uncomfortable Pace - You don't get anything you want by being comfortable. If you're working in a way that feels easy and setting deadlines where everything seems smooth, you're not growing, you're not learning, you're not getting there. That's a lesson from running, and it's a good lesson for work.

Set Audacious Goals - We're setting two extremely big goals at The Atlantic. Our projections don't suggest we're going to hit them. But the same was true last time when I said we're gonna get profitable and a million subscribers in three years. We got there. Sometimes having a really big goal motivates you and forces all the tough choices.

Continuous Forward Motion Matters Most - When I realized yesterday's marathon was going badly, I kept telling myself: continuous forward motion. Sometimes the goal becomes just finishing. It's better to make a full drop in pace and hold that than to slowly slide backwards every mile once you know you won't hit your goal.

Every Extra Word Is an Opportunity to Lose People - Every extra word, every extra thought, every extra detail that doesn't propel the story needs to be removed. This book is 75,000 words, but there's 60,000 words I cut. Is this sentence absolutely essential? No? It's gone. That's storytelling, and that's leadership communication.

The Cocktail Party Test for Storytelling - If you describe what you're writing at a cocktail party, do people come towards you or walk away? I can talk about my 2005 cancer diagnosis and 2007 marathon, and people lock in. I talk about my 2009 marathon, and no one cares. Test what has emotional resonance with your friends.

Write and Speak To Help People SEE a Movie - When somebody's reading, they're visualizing it in their mind's eye. Can you see it? Can you feel it? If you can't run a movie in your head about what I'm writing, it shouldn't be on the page. Help them visualize it—the little white house in Concord, walking around Walden Pond.

Hiring: Spirit of Generosity and Force of Ideas - Spirit of generosity means can they work with people? Will they be territorial or figure out what's best for the org? Force of ideas means are you smart and sharp? I also want edge—a little bit of productive paranoia. Not complacent, but kind to everybody.

Discipline Can Show Up in Different Ways - My editor-in-chief hasn't run a mile in 25 years. Is he disciplined? Hell yeah. Works all the time, focused on every sentence. You can have mental discipline without physical discipline. I try to get the most out of different kinds of people with different strengths.

Keep Going - This is the hardest time to graduate because of AI and uncertainty. Find things you're passionate about and really focus on them. My twenties weren't great professionally. I found journalism, but I wasn't good at it yet. Keep pushing, and eventually things turn out for the best.

• What would happen if you moved at an uncomfortable pace in your most important work?
• Where are you setting deadlines that feel too easy and smooth?
• Are you ruthlessly cutting everything that doesn't propel your story forward? What sentence, meeting, or project exists simply because it always has, not because it's essential?

Former Episodes Referenced

#603 - Michael Easter - The Comfort Crisis

#611 - Codie Sanchez - Main Street Millionaire

#654 - Jake Tapper - Be So Good They Can't Ignore You

Time Stamps:

02:05 Nick's NYC Marathon Experience

03:35 Nick's Father's Legacy

11:43 Running and Leadership

17:08 Overcoming Cancer and Running Again

19:24 The Importance of Setting "Stretch" Goals

21:30 Marathon Challenges and Lessons

27:09 The Warrior Athlete and Early Lessons

28:54 Nick's Role as CEO of The Atlantic

29:30 Unique Talents for a CEO Role

30:42 Balancing Multiple Interests

32:30 Writing 'The Running Ground'

37:37 Crafting a Compelling Story

41:24 Storytelling Tips for Leaders

44:15 Hiring the Right People

51:55 Running and Parenting

54:06 Advice for New Graduates

56:07 EOPC

Go to www.LearningLeader.com for full show notes

This is brought to you by Insight Global. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver.

My Guest: Suzy Welch is known for co-founding the Jack Welch Management Institute and writing bestsellers like 10-10-10: A Life Transforming Idea. Her career includes roles as an editor-in-chief for Harvard Business Review, a crime reporter, and a professor. She teaches at NYU and is the best-selling author of Becoming You.

Purpose Requires Realism, Not Just Passion - Everyone wants to be the drummer in Disturbed, but that guy's good at drumming. My whole methodology is about realism. You have to know what your values are, what your interests are, but you better be good at it or forget it. Otherwise, it's a hobby.

Values Are Choices, Not Virtues - Most people confuse values and virtues. Virtues are things like integrity, courage, and thankfulness... Behaviors we all should have more of. Values are choices about how you want to live, work, and relate. It's a value if it would drive who you married, what job you took, and where you went on vacation.

There are 16 Measurable Values - Values exist on a continuum like a DNA profile. Scope reflects how exciting a life you want. Radius is how much you want to change the world systemically. Belovedness is how important an intimate relationship is to you. Work centrism is whether you love work for work's sake or if it's just a means to an end.

Men Over 32 Value Romantic Relationships Most - We just got data showing that for men over the age of 32, belovedness is their number one value. It's much lower for women. Only 50% of people have family centrism in their top five values—we assume everyone shares our values, but they don't.

Your Authenticity Gap Reveals Your Pain - You could hold the value of scope as number one, but not be able to live it right now because of your job or family situation. That gap between what you value and what you're living—we call that your authenticity gap. If you've got a big one, you know it because it hurts.

Gen Z's Top Value Is Self-Care - 75% of Gen Z have self-care, wellbeing, pleasure, and leisure as their top value. Their top three are self-care, authentic self-expression, and helping others. Meanwhile, hiring managers want achievement, scope, and work centrism. The overlap is 2%.

Aptitudes Are Your Brain's Dominant Hand - We have nine cognitive aptitudes preset by age 15. Are you a generalist or a specialist? A future focuser or a present focuser? A brainstormer or someone who comes up with one fully baked idea per year? It's painful to be a generalist in a specialist job.

Your Personality Is How The World Experiences You - Your personality is not the list of adjectives you write about yourself. It's how the world experiences you. When I did my 360 feedback, people said I was the hurricane, not the calm at the center. I had to learn to communicate better the thoughts I had, and learn to be less chaotic.

Everyone Writes Themselves As The Hero - A police lieutenant once told me: everyone writes the story of their life with themselves at the center as the hero. No matter what story we tell ourselves, we always cast ourselves as the hero. That's why self-awareness is so hard and why we need testing, not just self-reflection.

The Aperture Problem: Kids Only Know Five Jobs - When kids come out of high school, they only know about five jobs, two of which are their parents. By college it goes up to seven. By grad school, MBAs are thinking about two or three options—banking, consulting, or tech. There are 135 industries and thousands of types of work nobody tells them about.

Great Leaders Don't Do It For The Money - I've been blessed to know many of the greatest leaders. They're doing it for love of people, excitement, work, or impact. I've never met a great leader who was doing it for the money. Jensen Huang and Jeff Bezos are examples—clarity, vision, excellence in everything, no shortcuts.

Better To Be The Author Than The Editor - When you're ambitious, you end up surrounded by voices and can become the editor of your life. You have to become the author. Paint a self-portrait of yourself standing still so that when you start running, you know where you're going and why.

• What would the 5 people closest to you say about how you show up? Would their description match how you see yourself, or do you have a self-awareness gap you haven't addressed?
• If you mapped your actual daily behaviors against your stated top values, would they align? Or are you living someone else's version of success while calling it your own?
• Are you the author of your life or the editor? Whose voices are loudest in your head when making big decisions, and have you given yourself permission to write your own story?

Former Episodes Referenced

#127: Adam Grant - How Originals Impact the World

#441: Liz Wiseman - How to Build Credibility, Solve Problems, & Multiply Your Impact

#350 - Tom Rath - Answering Life's Great Question

Go to www.LearningLeader.com for full show notes

This is brought to you by Insight Global. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver.

My guest: James Clear is the author of one of the most influential books of our generation, Atomic Habits. He's sold over 25 million copies worldwide and has helped millions of people transform their lives through the power of small changes. We brought the podcast to the campus of Ohio University, where we recorded live in front of 250 of the most impressive college students I've ever met.

Notes:

I loved the Morgan Housel moment - It was cool to see James' reaction to it (you can watch it on YouTube.com/RyanHawk). Morgan said, "I have absolutely not a single cell of envy for him. Because he is the nicest guy you will ever meet. You will not meet a nicer human than James Clear. You will not meet someone as successful as he is and as humble as he is. He is a saint in my life. And because of that, I adore every bit of this guy, so I cannot envy him. I am just inspired by his success, full stop." We should all strive to be that for the people in our lives.

Your WHO - "Every opportunity in life comes through a person. Relationships are usually the most important thing. If you want to achieve more, there is a relationship that can unlock better results. If you want to make a meaningful contribution, helping others is a great way to do it. If you sim

Willpower – 'People with tremendous self-control aren't that different from those who struggle. They're simply better at structuring their lives in a way that doesn't require heroic willpower.' It's not about determination, it's about design. That's liberating.

Fall in Love with the Process - "When you fall in love with the process rather than the product, you don't have to wait to give yourself permission to be happy. You can be satisfied anytime your system is running. And a system can be successful in many different forms, not just the one you first envision."

Make It Obvious, Easy, Attractive, Satisfying - The four laws of behavior change: make good habits obvious and bad habits invisible, make good habits easy and bad habits difficult, make good habits attractive and bad habits unattractive, make good habits satisfying and bad habits unsatisfying.

Use the Two-Minute Rule - Scale any habit down to something that takes two minutes or less. Want to read more? Read one page. Want to run a marathon? Put on your running shoes. The goal is to master showing up and make the entry point as easy as possible.

Standardize Before You Optimize - You can't improve a habit that doesn't exist. Master the art of showing up before worrying about optimization. Build consistency first, then work on increasing the dose or improving performance.

Track Your Habits Visually - I use a paper clip strategy: start each day with 120 paper clips in one jar, move one to another jar each time I complete a writing session. Visual tracking provides clear evidence of progress and makes the habit satisfying.

Habits Need to Match Your Personality - There's no one-size-fits-all approach. Morning people and night owls need different strategies. Work with your natural tendencies, not against them. Choose habits and contexts that align with who you already are.

Create Commitment Devices - Make bad habits difficult through commitment devices. I had my assistant change my social media passwords every Monday and only give them back on Fridays. This eliminated mindless scrolling during my productive work hours.

Focus on Systems, Not Goals - Winners and losers have the same goals. The difference is their systems. Goals are about the results you want to achieve; systems are about the processes that lead to those results. Fall in love with the process, not the outcome.

Build Habits That Align With Your Desired Identity - I wanted to be a writer, so I wrote every Monday and Thursday for years. Eventually, I had proof. I couldn't deny I was a writer because of the body of work I'd created. Your habits are how you embody your identity.

The Plateau of Latent Potential - We expect progress to be linear, but it's not. Habits often appear to make no difference until you cross a critical threshold. You need to persist long enough to get through the plateau and break through to the other side.

Reduce Friction for Good Habits - I want to work out more, so I lay out my workout clothes the night before. When I wake up, they're the first thing I see. The easier you make the habit, the more likely you are to do it.

Increase Friction for Bad Habits - Want to watch less TV? Unplug it after each use and put the remote in another room. The added friction makes the bad habit less appealing and gives you a moment to make a better choice.

Automate Good Decisions - Technology can lock in good behavior. I set up automatic transfers to my investment account. Once the system is in place, the good behavior happens without requiring willpower or decision-making energy.

On Building Habits in College - The mess of college is actually useful because you're forced to figure out who you are. Use this time to experiment with different habits and see what sticks. You have more flexibility now than you will later in life.

On Breaking Bad Habits - Trying to eliminate a bad habit without replacing it with something else is really hard. The more sustainable approach is habit substitution. If you want to stop scrolling social media, replace it with reading for five minutes instead.

On Staying Consistent - Never miss twice. Missing once is an accident; missing twice is the start of a new habit. Elite performers aren't consistent because they're more disciplined—they have better strategies for getting back on track quickly when life happens.

On Finding Your Purpose - I think the idea of finding your purpose is misleading. You don't find your purpose; you build it through the habits you practice daily. Your life is essentially a collection of your habits, so if you want a different life, build different habits.

On Overcoming Setbacks - After my accident, I had to redefine what success looked like. Sometimes progress means recovering what you lost rather than reaching new heights. Focus on what you can control today rather than what you wish you could control.

On Reading and Learning - I read across many disciplines because insights often come from connecting ideas from different fields. Read widely, take notes, and revisit those notes regularly. The goal isn't to finish books—it's to find ideas that change how you think.

On Building a Writing Practice - I published twice per week for years before anything took off. Most people overestimate what they can accomplish in one year and underestimate what they can accomplish in ten years. Show up consistently and let time do the heavy lifting.

Reflection Questions

• Are you focused on achieving goals or building systems? What's one process you could improve this week that would make your desired outcomes more likely?
• What's one habit you want to build? Can you make it so easy that you can't say no—something that takes two minutes or less? How can you design your environment to make this habit obvious and attractive?
• Which of your current habits align with the identity you want to build? What small votes can you cast today through your actions to prove to yourself who you want to become?

Former Episodes Referenced

• #529 - James Clear - Becoming an Optimist, Creating Your System, & Setting Up Your Future Self
• #655 - Morgan Housel - The Simple Formula For Happiness, Betting on Others, & Gaining Independence & Purpose
• #594 - Charles Duhigg - Becoming a Super Communicator
• #470 - Daniel Coyle - Building Your Culture, Solving Hard Problems, & Winning The Learning Contest
• #428 - James Clear - Asking Better Questions, Taking Action, & Doing A+ Work

Episode Timestamps:

02:20 High Praise from Morgan Housel

04:08 Winning the St. Gallen Symposium & James' College Experience

07:00 The Strategy Behind Writing Atomic Habits

13:58 Designing Your Environment for Success

31:05 The Art of Building Genuine Relationships

39:00 Clarifying Your Thoughts Through Writing

40:11 Applying Atomic Habits to Leadership

41:04 Mental Performance Techniques from a Navy SEAL

43:31 Balancing Success and Personal Life

47:56 The Importance of Reflection and Review

51:10 Adapting Habits in Different Environments

55:19 Habits for Short-Term Goals vs Long-Term Goals

01:04:27 Using Feedback for Habit Building

01:07:55 Internal Dialogue While Building Habits

01:13:28 The Influence of Others on Forming Your Habits

01:17:01 EOPC

Go to www.LearningLeader.com for full show notes

This is brought to you by Insight Global. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver.

My Guest: Derek Sivers is the founder of CD Baby and author of "Hell Yeah or No" and "Useful Not True." He shared how he graduated from Cal Berkeley in two years instead of four because the "standard pace for chumps" - a lesson that shaped his entire career of institutional skepticism and unconventional thinking. From creating viral shipping emails to understanding why explorers make bad leaders, Derek shares why being busy means being out of control, how your first thought is an obstacle to your best work, and why you can't predict what the world will want from you until you try everything and listen closely to what it's telling you.

Notes:

No Speed Limit – Most things are paced so the slowest person can keep up. If you're driven and motivated, you can go so much faster than the standard pace. I graduated from Berkeley in two years by learning four semesters of harmony in one hour. "The standard pace is for chumps. You can do so much better than that."

Question the Standard Process – When someone says you must go through usual channels or something will take a certain time, assume there's probably a hack. Develop institutional skepticism - there's usually a better way than how most people do it.

Create Opportunities, Don't Wait for Them – You don't have to wait until a company is hiring. If you can see how to benefit them, walk in and show them what you can do for free first. Alan Tepper made Warner Brothers more money than anyone that year by just showing up with a plan.

Make Everything Valuable to Others – The starving artist spends all their time on work valuable to them but not to others. Use money as a neutral measure - if you can make money with your art, it ensures what you're doing is valuable to other people. "It's almost impossible to predict what the world will want from you... Keep yourself out there and listen closely to what the world is telling you it wants from you."

Stand Out by Being Different – Don't imitate what everyone else is doing. I wrote a silly shipping email in 10 minutes that became one of the most viral emails ever mentioned in business books. Ask yourself constantly: What has nobody done before?

The First Follower Creates the Movement – We focus on the shirtless dancing guy, but the first follower is what made everything happen. Until then, people kept their distance from the freak. If you find someone doing something great, follow them and show others how to follow.

Every Sentence Must Matter – My books are 90-100 pages, but start as 1,000-page rough drafts. I spend 1-2 years full-time chopping every sentence that doesn't absolutely need to be there. "I'm not gonna put a single sentence out into the world that doesn't need to be there." Make every word count - eliminate everything that doesn't add value.

Hell Yeah or No is Context-Dependent – This tool is for when you're overwhelmed with options and need to raise the bar. Straight out of college, say yes to everything because opportunities are like lottery tickets. Once something rewards you, then say no to other things and double down.

Busy Means Out of Control – "Busy to me implies out of control. You're busy if you've let other people shove shit into your schedule." Leave space instead of filling it - that time to think is what creates valuable insights others don't have time to develop.

Your First Thought is an Obstacle – Don't honor the thought that came first. In brainstorming, acknowledge the first idea, then keep going - don't stop at two or three. Even silly ideas can seed great ones you'd never reach without that stepping stone.

All Beliefs Are a Myth – People worshiped Zeus for centuries; now we call it mythology. But we say our own beliefs are true while others' are superstitions. I expected China to be awful from American news, but found it wonderful - question what you've been told.

Use Prejudice as Your Compass – If you notice you're prejudiced against something, that's exactly what you should explore. Burning Man sounds awful to me; therefore, I should probably go. Steer into your biases to overcome them and gain new perspectives.

Explorers Make Terrible Leaders – Explorers try everything and change direction constantly, which frustrates teams. Leaders go in a straight line to a clear destination, unwavering in mission even if the path changes. I loved changing my mind, which made me a bad leader until I learned the difference. Set projects with clear missions, even if you're personally exploring other things.

Try Everything Until the World Says Yes – I had a booking agency, a record label, a recording studio, and my own music - all failures. Then, a side project to help friends (CD Baby) took off. You can't predict what the world wants from you, so try many things and listen closely to what it's telling you.

1. What "standard pace" are you accepting in your business or career that you could actually accelerate if you questioned it? Where have you assumed something has to take a certain amount of time just because that's how it's always been done?
2. Are you spending time on work that's valuable to you but not to others? How could you test whether what you're creating actually solves problems people are willing to pay for?
3. Are you acting more like an explorer or a leader right now? If you're constantly changing direction, how could you set clearer missions for your projects while keeping your personal explorations separate?

Derek's Content:

• Derek's website and blog
• "Leadership Lessons from Dancing Guy" (First Follower) TED Talk - Derek Sivers
• "No Speed Limit" essay

Former Episodes Referenced

• #647 - Tim Ferriss - Chasing Your Curiosity
• #562 - Nikki Glaser - The Creative Process of a Comedian
• #644 - Blaine Anderson - Confidence, Curiosity, Connection

Episode Timestamps

02:20 Early Life Lessons from Kimo Williams

05:21 Corporate Lessons and Unconventional Paths

09:10 The Power of Adding Value

13:57 Viral TED Talk: Leadership Lessons from the Dancing Guy

22:03 The 'Hell Yeah or No' Philosophy

27:29 The CD Baby Experience

28:02 Starting an Online Record Store

29:10 Creating a Unique Shipping Notice

30:01 The Viral Impact of Creativity

32:53 The Importance of Regular Writing

35:17 Questioning Assumptions and Beliefs

36:23 Exploring New Perspectives

40:41 The Explorer vs. The Leader

48:21 Advice for Aspiring Leaders

Resources:

• Read: The Score That Matters
• Read: The Pursuit of Excellence
• Read: Welcome to Management
• To Follow me on X: @RyanHawk12

Go to www.LearningLeader.com for full show notes

The Learning Leader Show with Ryan Hawk

This is brought to you by Insight Global. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader

My guest: Dave Berke is a retired US Marine Corps Officer, TOPGUN Instructor, and now a leadership instructor and speaker with Echelon Front, where he serves as Chief Development Officer. As a F/A-18 pilot, he deployed twice from the USS John C Stennis in support of combat operations in Iraq and Afghanistan. He spent three years as an Instructor Pilot at TOPGUN where he served as the Training Officer, the senior staff pilot responsible for the conduct of the TOPGUN course.

Notes:

• July 2001: Plans Don't Survive Contact - Dave's Top Gun graduation exercise as flight lead. Wingman yells, "Showtime one-one break right!" - an F-5 snuck into formation. Dave was staring at the radar instead of looking out, had to fall out of formation, and ended up at the back instead of leading from the front. Mission successful, but nothing like he planned. Dave: "The outcome was still really good... except it was nothing like I thought it was going to be." Lesson: You're planning for the success of the outcome, not how you're going to do it.
• The most important attribute in a leader is humility. To be effective, you must be able to listen, learn, be flexible, and admit you're wrong sometimes. One of the biggest issues they deal with when working with leaders is ego and/or the inability to be humble. As leaders, we need to be self-aware enough to realize when our ego is getting the best of us. And surrounding ourselves with people who will help us know when that is happening as well.
• Be Fluid with Plans, Deliberate with Outcomes - Be really fluid and loose with plans, but deliberate about aligning the team on outcomes. Dave grew up as a control freak, OCD planner. Dave: "In life, it's just not how life works... If you can align on the mission and outcome, and you are very open-minded that there are a lot of different ways to get there, you're far more likely to be successful." The military saying, "The enemy gets a vote." Ryan's quarterback coach after an interception: "He's on scholarship too, you know?"
• Process: How You Create It Matters Most - Process is important, but how you create it matters most. If you agree on the outcome, the conversation should be less about agreement, more about "When you talk about step one, what are you thinking? How does this lead to step two?" The process has to be organic. When you create it, you're more likely to maneuver around challenges.
• Book Dedication: Chris and Kat - Book dedicated to Corporal Chris Leon and his mother, Kat. Chris was a radio operator on Dave's 13-man Anglo team. June 20, 2006, Chris was killed by an enemy sniper in Iraq - first Anglican Marine killed there. Dave's son is Matthew Leon Burke - took Chris's last name. Chris's mom Kat is Aunt Kat to Dave's family. Dave: "I always say I really deep down wish I didn't know Kat, because that would've meant Chris came home and life just went on. But that's not what happened." Chris taught bravery. Kat taught strength.
• Top Gun Reality: It's About the Team - 1986 Top Gun most impactful movie on Dave's life at 14. But the movie depicts a lone wolf. Marine Corps teaches: Your contribution to the team matters most. A really good pilot who's self-centered will do more damage than a slightly less capable pilot who's a real team player. Dave: "If there's ever a team sport, it's going into combat... It's not about you. It's about the team."
• Trust: Action, Not Description - Echelon codifies relationships: Trust, respect, listening, influence. Trust is the cornerstone. Dave: "If you don't trust me, I could be good at so many things. If there is a trust gap, there's going to be a problem in the relationship and team." Trust is action you take.
• Ego: The Universal Challenge - When Echelon works with companies, challenges are almost always connected to ego. Dave: "Our egos tend to wreak havoc at each level of organization." From birth, the ego drives us down the wrong path. When debating plans, ego says, "You're right, he's wrong." Building good leadership is managing egos. Dave: "Humility is the most important attribute in a leader. All the attributes, humility is number one, and we don't waffle on that."
• Humility Enables Everything Else - Dave worked with the biggest, toughest SEALs. Attribute most critical to success: humility. Ability to listen, learn, be flexible, change, admit you're wrong, and go with someone else's plan. It even affects fitness. Humility touches everything. Doesn't diminish other attributes, but allows you to strengthen them.
• Teaching Humility: Subordinate Your Ego - You can't tell someone with a big ego to be humble. Dave: "The biggest challenge with someone else's ego is not their ego. It's your ego's response to it." Most counterintuitive thing: If you clash with Ryan, Dave has to subordinate his ego to Ryan's. Lower your ego: "Hey Ryan, I've been pushing back hard, I realize I'm not listening." Natural reaction: Ryan's ego starts to drop. Over time, collaborate more. You connect success to the ability to control the ego. Dave: "Humility is the measurement of how much control you have over your ego." What you give is usually what you get. It's reciprocal.
• Care About Team More Than Yourself - When your people see you working hard to clear paths or block an egomaniac boss, they'll run through walls for you. Outcome of a good relationship: You care about the team, the team cares about you. That selfless act shows you care about them more than yourself. Dave: "That's how you show that you care about them more than yourself, and that's what a leader's job is, to care about the team more than you care about yourself. That's parenting, that's marriage."
• Extreme Ownership - Book Extreme Ownership changed Dave's understanding. When you take ownership, take ownership of everything. Caveat: Not things you literally don't control. But you have ownership over everything, even just how you react. After Chris was killed, Dave said, "That's war, nothing we can do." Problem: When he embraced it wasn't his responsibility, it meant he didn't have as much to change. Should have asked: "What is everything we can do to make sure this doesn't happen again?" The tendency is to undershoot ownership. Try to take it to the extreme. If you can take ownership of everything you can control, you get more influence over the outcome.
• Detachment: A Superpower - Dave: "Detachment is a superpower" - (1) almost nobody can do it, and (2) if you can, it's massively influential. Detachment is being in control of emotions. When overwhelmed with priorities and pressures, you tend to get emotional. When you react emotionally, you make bad decisions. Learn the skill of detaching - not to be devoid of emotion (we're human), but don't let emotions dictate.
• Get Away from Problems to See What's Causing It - When a problem occurs at work, you tend to focus on it, go into it. It seems good but is often wrong. You should get away from it, detach. Getting away lets you look around and see what's really causing it. Military example: The enemy is shooting at you; the tendency is to focus on that. Usually bad because they're hoping you do - then they send a flanking maneuver. If you detach, step back, you'll see the flanking maneuver coming. Be able to see the future - that's the superpower.
• Know Your Red Flags - Intervene Early - You have to understand where you are escalating your emotions. Know your personal red flags. Most people don't go zero to 100. Long day, flight delayed, bad meeting - little things tick up, so zero is actually 4 or 5, which means dirty dishes put you to 7. When Dave gets frustrated, traps tighten up. Some people's nose turns red. If you're at level 8 and someone says, "calm down," it makes it worse. But if at level 1 or 2 and you intervene, you're in control. What an adult does: "I'm an emotional guy, but I have awareness of where I am. If I'm a 4, I gotta intervene then." If at level 10, detaching is not gonna happen. That's the difference between kids and adults. Dave: "You are much more likely to have a hard time controlling your emotions, ironically, with people you care about the most."
• Quotes:
  • "You're planning for the success of the outcome, not how you're going to go about doing that, because things get in the way."
  • "Humility is the most important attribute in a leader. All the attributes. Humility is number one, and we don't waffle on that."
  • "The biggest challenge with someone else's ego is not their ego. It's your ego's response to it."
  • "Detachment is a superpower."
  • "You are much more likely to have a hard time controlling your emotions, ironically, with people you care about the most."

01:16 Introducing Dave Burke

02:21 Dave Burke's Top Gun Experience

05:23 Lessons Learned from Military to Everyday Life

07:56 The Importance of Flexibility in Leadership

13:07 The Need to Lead: Dedication and Personal Stories

16:58 The Realities of Teamwork in Combat and Business

21:03 Building Trust and Relationships in Teams

26:04 The Role of Humility in Effective Leadership

31:03 Understanding Ego and Humility

31:50 Subordinating Your Ego

33:38 Challenges of Teaching Humility

34:07 Personal Experiences with Ego

39:20 The Power of Ownership

42:57 Detachment as a Superpower

52:58 Advice for Young Leaders

57:26 Conclusion and Key Takeaways

Go to www.LearningLeader.com for full show notes

This is brought to you by Insight Global. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver.

My Guest: Helen Lewis is a staff writer at The Atlantic and author of The Genius Myth: Great Ideas Don't Come from Lone Geniuses.

Notes:

• Shakespeare: Talent + Luck + Timing - William Shakespeare died in 1616 at age 52, celebrated but not yet immortal. His icon status required massive luck: friends published the First Folio (saving King Lear), then 50 years later, Charles II reopened England's theaters after Puritan closures and needed content. Companies turned to Shakespeare's IP, adapting his work (including changing tragedies to happy endings). Helen: "If anyone deserves to be called a genius, it's him. But he died as a successful man of his age.
• Scenius Over Genius - Brian Eno coined "scenius" - places that are unusually productive and creative. Shakespeare moved from Warwickshire to London for the theaters and playwrights. Helen: "You don't just have to be Leonardo, you also need Florence... Where do you find the coolest, most interesting bleeding edge of your field?" Modern example: Joe Rogan's Comedy Mothership in Austin created an alternative to LA/NYC for comedians like Shane Gillis and Tony Hinchcliffe. Ryan: "Put yourself in rooms where you feel like the dumbest person... force you to rise up, think differently, work harder."
• Tim Berners-Lee vs. Elon Musk - Tim Berners-Lee invented the World Wide Web. Has knighthood, lives an ordinary life, kids named Alice and Ben. Most people have never heard of him. Elon Musk has a lot of children, talks about his genes needing to live on, and lives a very public life. Helen: "We overrate the self-promoters, the narcissists. We demand oddness and specialness... We don't call modest people geniuses because they're too normal." Elizabeth Holmes (Theranos) and Sam Bankman-Fried (FTX) exploited this - looked like a genius (Steve Jobs cosplay, messy math prodigy) but stood on houses of cards.
• Trauma and the "I'll Show You" Engine - Matthew Parris wrote Fracture after noticing how many "great lives" had traumatic childhoods - loss of parents, being unloved, bullied. Helen: "I don't think that's necessarily genius in objective achievement. It's more like a hunger for recognition or fame... a kind of 'I'll show all of you' engine."
• Stephen Hawking on IQ - Stephen Hawking: "I have no idea. People who boast about their IQ are losers." The Flynn Effect shows average IQ rose over the 20th century through better nutrition, schooling, and living conditions. Higher IQ correlates with better outcomes. But at the top end, every IQ point ≠ is one success point. Christopher Langan (the highest IQ guy) thinks he has a theory to overturn Einstein, and that Bush did 9/11 to cover it up. No history of achievement. Helen: "Smart people don't always prosper. You need the gears that connect the engine to the wheels on the road."
• Conspiracy Theories: Narcissism as Driver - Narcissism is the most correlated personality trait with conspiracy thinking. Helen: "The sheeple, the NPCs think this, but I alone have seen the truth. It positions you as the protagonist of reality." The Internet is a "confirmation bias engine." But conspiracies are sometimes true (Epstein's corrupt plea deal), which is why conspiracy thinking persists. Researcher Karen Stenner's solution: Get back to depoliticized conspiracies like Bigfoot, crop circles, Area 51 - harmless things that got people outside instead of "shoot up a pizza restaurant."
• The Beatles: Finiteness Creates Legend - Psychologist Han Isaac said geniuses should either die before 30 or live past 80. Middle is "eh." The Beatles had both: a short career that ended definitively, then John Lennon was shot at 40, frozen in time. Paul McCartney lives on, performs at Glastonbury with John's vocals. Craig Brown: "The Rolling Stones just go on and on, but there's never as much of the Beatles as you want."
• Quality Over Quantity - Helen: "Incentive now is producing constantly for algorithms... That's neither fun nor produces the best work." Early career: say YES. Later career: "The most important thing you can say is no." Her metric: "Can I say honestly, that was the best I could do? I didn't cut corners. That's the metric." Podcast: advised to do 2-3 episodes weekly for rankings, has been doing weekly for 10.5 years. Shows that went daily? He stopped listening. "I'm gonna increase the quality bar, not the quantity." Robert Greene: "Do not speak unless you can improve upon the silence."
• Improving the Silence - "My dad's not the loudest at family gatherings, doesn't have the most words, but when he speaks, we all stop and listen. That's who you want to be." Applies to meetings: people vomit garbage to show how smart they are instead of waiting for something valuable. When you speak, people should want to listen.
• Thomas Edison: Execution Over Ideas - The Light bulb wasn't Edison's conceptual innovation - the idea dated to Humphrey Davy. What was incredible: Edison made it work (vacuum seal, filament) and created the New York power grid. Helen: "Lots of people can have the idea that a man should be an ant. Not everybody can write the Ant-Man screenplay and have it produced." His Menlo Park lab lasted because he worked with brilliant people on problems they cared about. Logbook shows assistants' names on breakthroughs - collaborative. We underrate logistics and execution. Most "light bulb moments" are actually slow, incremental, contested creations.
• Why Helen Chooses Teams Over Independence - Could go independent on Substack for more money. Works at The Atlantic for: resources, legal support, editorial integrity, and colleagues she doesn't want to let down. Helen: "You must have people in your life, you think, I wanna do work that they like. Finding those people who make you your best version of yourself." Ryan connects to athletics: "Being surrounded by people better than me forces me to raise my game. That's why we want to be part of a great team."
• Sample First, Specialize Later - High achievers have "hot streak" later, but sample early - trying different things, learning transferable skills. Helen: "Take the first job at a publication you could learn from. Even if not wildly interested, if it's good and they'll hold you to high standards, do it. Your second job is infinitely easier to get than your first."
• Work Around People Who Care - Helen: "If you work somewhere where no one cares, it's very hard. You can't care on your own. You'll become infected by the apathy around you." Nothing is more boring than a job you don't care about.
• Don't Wait to Live - Some devote long hours to something for money, promising they'll retire at 30 and then live. Helen: "What if you spent all that time chasing something and then you get hit by a truck? Don't wait for it. Just try and enjoy what you're doing right now."
• Quotes:
  • "You don't just have to be Leonardo, you also need Florence."
  • "We overrate the self-promoters and underrate the humble achievers."
  • "Smart people don't always prosper. You need the gears that connect the engine to the wheels."
  • "The most important thing you can say is no."
  • "Do not speak unless you can improve upon the silence." - Robert Greene
  • "You can't care on your own. You'll become infected by the apathy around you."
• It's funny that we have come to use the phrase 'lightbulb moment' to describe a momentary flash of inspiration, because the birth of the lightbulb was slow, incremental, and highly contested.

Go to www.LearningLeader.com for full show notes

The Learning Leader Show with Ryan Hawk

This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader

Guest: Dakota Meyer, a United States Marine Corps veteran and Medal of Honor recipient. At just 21 years old, Dakota's actions during the Battle of Ganjgal in Afghanistan saved many lives when he repeatedly went against his orders and drove into a Taliban ambush zone to rescue trapped soldiers. He became the first living Marine in more than 40 years to receive the Medal of Honor. Today, he's a firefighter, entrepreneur, and New York Times bestselling author. Dakota is dedicated to developing leaders who can handle crisis and complexity. In our conversation, you'll hear why Dakota believes his most heroic day was actually his greatest failure, what he was feeling the day he received the Medal of Honor from President Obama, and his practical blueprint for bringing our divided country together.

Notes:

• The Three-Phase Life Cycle - Dakota's framework for wisdom: "You have an obstacle you face. You have to get through that obstacle and become better from it. And then the third piece is you have to share how you got through that obstacle."
• Leadership vs. Responsibility - "Leaders are just people too. You can lead from anywhere in an organization... Leadership comes in many forms." True leadership means choosing where your loyalty lies - with the people you're responsible for or with protecting your own position.
• September 8th, 2009: Leadership Failure - Dakota frames his Medal of Honor actions as "an absolute story of leadership failure at its best" - multiple levels of leaders avoiding responsibility while he went against orders to save his teammates.
• The Loyalty Question - "Where does their loyalty lie? Is it in the people that trust them to lead them and to protect them? Or is it in the organization in order for themselves to keep getting promoted?" This fundamental choice defines every leader.
• Risk vs. Results - "Organizations and leaders today are so risk-averse that risk comes before results... You can't be successful, do hard things, and stay comfortable and be safe. In no world does that exist."
• Mental Health Reality Check - Dakota challenges current mental health approaches: "We're giving people no hope because we're trying to accommodate their emotions and not bring them back to reality and logic." He distinguishes between trauma that needs addressing and self-induced mental health issues through poor choices.
• Love as Choice, Not Emotion - "Love is not an emotion. Love is a choice... If you love me, you're going to always help me be the best version of me. That doesn't always feel good."
• Accountability and Fatherhood - As a father of two daughters: "I can't be anything that I wouldn't let anybody else be to them... You set the bar for what they're gonna accept and what they're not gonna accept."
• The Civil War Warning - "America doesn't need a Civil War. What we need is to vote, to lead, to speak up in schools, to teach our kids history, truth, kindness with strength, and how to disagree without violence."
• The Ambush - When his team walked into an ambush, promised support assets (air support, mortars, quick reaction force) weren't available due to rules of engagement restrictions. When Lieutenant Johnson called for artillery support, saying, "If you don't give me these rounds right now, we're going to die," the response was "Try your best."
• The Decision to Act - Dakota requested permission to help multiple times and was denied each time. He finally went against orders with his driver, Staff Sergeant Rodriguez Chavez, making four or five trips into the valley over six hours to evacuate wounded and recover bodies.
• The Human Cost - Dakota describes the helplessness of watching Afghan soldiers get "mowed down" while running toward his vehicle for rescue. He performed basic life-saving measures, loaded wounded in trucks with the dead on the bottom and living on top for triage priority, and ultimately recovered some of his fallen teammates.
• The Immediate Aftermath - Dakota put his teammates in body bags, flew them home, then immediately returned to cleaning his truck and helping Afghan soldiers with their dead. He went back to his base alone - the only survivor of his four-man team.
• Mental Health Crisis - Dakota developed a destructive cycle: daily drinking (depressant), massive caffeine intake to compensate, creating anxiety and amplifying trauma. He was surrounded by people who only wanted to discuss trauma and war stories, preventing healing.
• Suicide Attempt - Dakota reached a breaking point where he held a gun to his head, but it wasn't loaded. This became his turning point - he made a commitment to either "rack it back and go ahead and do it, or go out and find a way to get through this and start living a life worthy of their sacrifices."
• The Path Forward - Recovery came through accountability rather than accommodation. Dakota emphasizes that while trauma needed addressing, he was "amplifying and feeding the problem, not the solution" through his choices.
• Real vs. Perceived Heroism - Dakota challenges the hero narrative: "I am an example of the potential that's in every human being... If they believe in a cause that's bigger than themselves, and they love people so much that they're willing to do whatever it takes to stop the suffering."
• Daily Character Building - "You don't just wake up and do the hard thing. It starts every day. Do you get up when you say you're gonna get up? Do you do what you say?" The Medal of Honor action was simply "upholding my end of the deal to my teammates and to my country."
• Being a Great Dad - Dakota sets an extremely high bar as a dad: "I believe that if your daughters start dating shitty and weak men, it's because you are a shitty and weak man." He sees fatherhood as the ultimate accountability.
• Unity through Truth - His current focus: "I just want to bring people together... I wanna put hope back in the world through truth." He believes in finding common ground with anyone through genuine connection and curiosity.
• Education vs. Knowledge - Dakota distinguishes between theoretical education and practical knowledge: "There's a difference between education and knowledge... those who can't do, they teach. We need more that have done teaching."
• The Power of Love - His core philosophy centers on love as action, not emotion: "Love is limitless... there's no expiration date" compared to hate and negativity, which "there's an expiration date on."
• Practical Application
  • Leadership Loyalty Test - Before making decisions, ask where your primary loyalty lies: with those you lead or with your own advancement
  • Risk-Taking Framework - Understand that meaningful results require accepting risk and discomfort
  • Mental Health Approach - Address trauma while taking responsibility for choices that amplify problems
  • Daily Character Development - Build integrity through small daily commitments before facing major challenges
  • Connection Over Division - Seek common ground through curiosity and questions rather than attacking opposing viewpoints

Go to www.LearningLeader.com for full show notes

The Learning Leader Show with Ryan Hawk

Morgan Housel is the New York Times Bestselling author of The Psychology of Money, Same As Ever, and The Art of Spending Money. His books have sold over 10million copies and have been translated into more than 60 languages.

This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver.

Notes:

• Morgan dedicated The Art of Spending Money to "Kellie the Unicorn" (his sister Kellie) after she was diagnosed with colon cancer and asked him to fulfill her long-running joke request. Sometimes book dedications "mean nothing to the reader, but they can mean everything to the author."
• People Who Bet on You - Brian Richards (Motley Fool boss) bet on Morgan when he didn't have to, providing unconditional support for a mediocre college writer. Craig Shapiro (Collaborative Fund) pursued Morgan for months to join his tiny VC firm as a full-time blogger when it wasn't a business necessity.
• What money can't buy - Morgan once heard a story from a priest that he'll never forget… It's from a priest who delivers the last rites in hospitals. He described the difference between what kids say to their parents when they're about to die. The priest tells them to tell their parents what they're most grateful for… In families with lots of problems, the kids usually talk about something that costs money. In the best families, the ones with solid relationships, the kids say the same thing every time. "Thank you for believing in me."
• Making vs. Spending Money - "There are literally tens of thousands of books written on how to make money... There are virtually no books written about how to spend money." Most people assume spending needs no guidance, but wealthy people often demonstrate this isn't true.
• The Internal vs. External Scoreboard - Donald Crowhurst (fake sailor who killed himself seeking external validation) vs. Bernard Moitessier (expert sailor who quit before winning to avoid attention and live authentically). Modern society pushes us toward Crowhurst's external validation while we actually want Moitessier's internal satisfaction.
• The simplest formula for a pretty nice life: independence plus purpose. The independence to do what you want, and the wisdom to want to do meaningful things.
• Chuck Feeney's Wealth Example - The duty-free store billionaire first lived the stereotypical rich lifestyle, realized he didn't like it, then chose to live modestly and give away $10 billion. "I was happy when I was giving money away, and I was not happy when I wasn't giving money away."
• Every Dollar of Debt - "Every dollar of debt that you have is a piece of your future that someone else owns." Debt narrows the range of outcomes you can endure in an unknowable future.
• Money and Happiness Research - Recent studies show that earning more money only helps if you're already happy, joyful, and content. For depressed, anxious people, more money doesn't improve well-being. "It leverages whoever you are in either direction."
• What Money Can't Buy - The book is "40% about how to spend money to make yourself happier and 60% about realizing what money cannot do for you." Relationships, health, and personal fulfillment must come first.
• "Comedians are the best thought leaders because they understand how the world works, but they want to make you laugh rather than making themselves feel smart."
• "Nobody gives a shit about anything other than how you make them feel."
• Vacation - Morgan realized while building sandcastles with his kids on the beach in Maui (10/10 experience) that building Legos at home with them was almost as good (9/10). The real value was "uninterrupted time with my family," which required travel to avoid daily distractions but pointed to what actually mattered.
• Ambition - Morgan's career drive crystallized while kayaking past $25 million mansions on Lake Washington in 2010: "I need to work harder. I want one of those one day." This wasn't envy but ambition - though he notes the line between inspiration and envy is thin, especially once you know the person.
• A high savings rate is not "saving" but is "purchasing independence." Each saved dollar buys freedom to handle life's unknowable future without someone else's schedule dictating his choices.
• Why Spending Is Complicated
  • People try to fill emotional holes with material purchases
  • Society tells us what we should like, which may not align with our actual preferences
  • We chase peer comparison rather than personal satisfaction
  • We overestimate the social rewards of nice possessions
• The Independence Framework
  • Save money not for retirement but for freedom to handle uncertainty
  • Debt narrows your options when life throws curveballs
  • Independence means being able to do what you want, with whom you want, for as long as you want
• The Internal Scorecard
  • "No one's watching. No one's thinking about you."
  • When people notice your possessions, they're either imagining themselves having them or envying you for them
  • Neither response gives you the social validation you're seeking
  • Use money to buy independence rather than others' admiration
• Relationship Investments
  • Focus on what creates "uninterrupted time with people you love"
  • Consider how purchases enable deeper connections (bigger kitchen for family dinners) vs. impressing others
  • Remember that belief and support matter more than material provision
• Purpose
  • Morgan's purpose became clear the moment he became a father: "There. That's it... I don't matter anymore. That's the only thing that matters right there." Purpose can be parenthood, work, religion, or community, but it needs to be bigger than yourself.
• "Comedians are the best thought leaders because they understand how the world works, but they want to make you laugh rather than making themselves feel smart." They deliver profound psychological and social insights while focusing on how they make you feel, not their own status.
• Regret -- Gerontologist Carl Pillemer interviewed 1,000 Americans aged 90-100. Not a single one said, "I wish I earned more money" or "I wish I worked harder." Nearly all said "I wish I spent more time with my kids" and "I wish I were nicer to my spouse."
• Inspiration vs. Envy -- Morgan credits James Clear as inspiration for "The Psychology of Money" and describes him as incredibly successful yet humble and kind. This creates pure inspiration without envy, unlike other successful writers whose personalities trigger competitive feelings.

Go to www.LearningLeader.com for full show notes

This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader

The Learning Leader Show with Ryan Hawk

Guest: Jake Tapper is an award-winning broadcaster and chief Washington correspondent, currently anchoring The Lead with Jake Tapper every day on CNN. He's also the #1 New York Times best-selling author of 7 books, including The Outpost (which was later made into a movie), Original Sin, and most recently Race Against Terror.

Notes:

• Be So Good They Can't Ignore You. Jake: I'm in control of how hard I work. It is our responsibility to work so hard that we become the obvious choice for the job or the promotion. Be So Good They Can't Ignore You. "I had to be so good that even though maybe on a broadcasting level I wouldn't be the number one pick... they had to give it to me."
• The one leadership skill that is massively important to develop… Don't insulate yourself with "yes" people. You have to have truth tellers in your life. Who are your foxhole friends? Who are the people who are willing and able to tell you the truth? Who are the ones who love you and care about you enough to let you know when you've messed up? Those people are gold. We all need them.
• Rejection: Dr. Seuss was rejected by 47 publishers. Rejection is part of life. You have to stay in the game for a chance to win it. Keep going. And nobody will give you a job to be nice. What value do you bring to a company? How will you make your boss's life better? You get hired to solve a problem, not because someone wants to be nice.
• Pinned tweet since 2017 – "To see what is in front of one's nose needs a constant struggle." -- George Orwell. A reminder to see obvious truths being obscured by spin or wishful thinking.
• "You Can Always Tell Them No" - Ted Koppel's crucial advice to young Jake about maintaining journalistic integrity and not compromising values for opportunities. This became a career-defining principle that Jake still follows 20 years later.
• The Jar Jar Binks Theory of Leadership - Successful leaders often remove critics from their inner circle, creating dangerous echo chambers. "Great people often achieve as much as they can to the point that they are able to remove from their inner circle anyone who tells them they're being an asshole or making a wrong decision."
• Constructive vs. Destructive Criticism - Jake learned to distinguish between useful feedback and personal attacks: "Very few of my critics are people that I actually care what they think... folks who understand I'm just trying to be a good faith operative here."
• Curiosity as Career Driver - Deep curiosity drove Jake from reading microfiche about MASH as a kid to investigating complex stories as an adult: "I find something interesting and I wanna find out everything I can about it."
• Rejection as Constant Reality - Even at his career peak, Jake faces daily rejection: "I get rejected every day... it doesn't matter that I've had New York Times bestsellers before... it's part of life."
• Humility Enables Learning - Accepting expertise gaps allows growth: "Having the humility to accept that I am not an expert on any particular thing... I'm a journalist, which means I try to be an expert on whatever I'm covering at that moment."
• Leadership Lessons From Powerful People
  • The Inner Circle Problem: Leaders systematically remove critics until surrounded only by yes-people, creating dangerous blind spots. Jake witnessed this pattern with Joe Biden (surrounded by aides and family who weren't honest about his declining acuity) and across industries.
  • The Solution: Intentionally maintain truth-tellers in your inner circle who care about you personally but will challenge you professionally.
  • Creating Truth-Telling Environments: Jake encourages healthy disagreement with executive producers, acknowledges power imbalances that make criticism harder for junior staff, and creates indirect channels for feedback ("some people on the staff think...").
  • The Criticism Paradox: Public leaders face constant harsh criticism, making them naturally defensive. Understanding this context helps leaders distinguish between constructive feedback that improves performance versus personal attacks that serve no purpose.
• Following Curiosity Despite Opposition
  • Jake's major works were all advised against by professionals:
    • The Outpost (no military expertise)
    • The Atlantic story of freeing a wrongly imprisoned man
    • Biden book (started the day after the election, despite uncertainty)
  • Key Insight: "Every single one of them, people were telling me not to do it... It's been following my curiosities even when people told me I'm not interested in that."
• The Hard Work Advantage: Jake couldn't compete on appearance or natural broadcasting ability, so he outworked everyone: broke stories constantly, used blogs when he couldn't get on air, and made himself impossible to ignore through sheer output.
• Dealing with Rejection
  • Expect constant rejection even at a career peak
  • Don't take rejection personally unless there's constructive feedback
  • Use rejection as data, not judgment of worth
  • Keep creating regardless of immediate acceptance
• The Wave Metaphor: Like Tom Hanks in Cast Away, timing the waves - "every code can be cracked" if you persist and find the right timing.
• Key Elements for Writers:
  • Strong structure: "Act one, chase your hero up a tree. Act two: throw rocks at your hero. Act three, get your hero out of the tree."
  • Good editor who pushes back - be willing to "kill your darlings"
• Life Philosophy
  • The Acceleration Mindset: At 56, Jake is speeding up output: "I don't know how much longer I have this window where people are paying attention... relevance is ephemeral... when it leaves, it looks fucking brutal."
  • For Young People: "So much of life is rejection... You cannot stop it... don't take it personally." Focus on developing skills and delivering value: "Nobody will give you a job to be nice... They'll do it because you have something they want."
  • Time Sacrifice Awareness: Success requires acknowledging costs: "What I cried about is the stuff I missed that I wasn't there for because I was chasing a story or on assignment."

Time Stamps:

02:46 Jake's Dedication to Influential Figures

05:05 Hot Mic Moment in Alaska

06:59 Preparing for Big Interviews & When to Follow Up

09:01 Dealing with Criticism

12:07 The Story Behind Jake's Pinned Tweet

13:48 Race Against Terror: The New Book

18:29 Balancing Multiple Roles

20:47 Chasing Your Own Curiosity

23:58 Sacrifices for Career Success

29:00 The Importance of Humility in Leadership

31:08 Surrounding Yourself with Truth Tellers

34:18 Healthy Tension in Team Dynamics

37:15 Understanding the Pressure on Public Figures

40:09 Empathy in Leadership

45:17 Balancing Career and Family

49:00 Advice for Aspiring Journalists and Writers

52:01 The Reality of Rejection and Hard Work

57:26 The Importance of Structure and Editing in Writing

01:01:16 End of the Podcast Club

Go to www.LearningLeader.com for full show notes

This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver.

Sukhinder Singh Cassidy is the CEO of Xero. Xero is a cloud-based accounting software designed for small businesses. They did $2.1 billion in revenue last year. Over the past 25 years, Sukhinder has had leadership roles at Google, Amazon, and StubHub.

Notes:

Key Learnings

• Strategic CEO Job Search Criteria – Sukhinder had four non-negotiables: macro tailwinds/good market, customer she could be passionate about, strong business model, and a role where she could "learn for miles" for 5-8 years. Only two companies met her criteria in 18 months of searching.
• "Sell, Interview, Sell" Hiring Process – First meeting is 50% selling the opportunity to attract top talent. Only after candidates lean in do you shift to intensive interviewing with leadership team exposure.
• The Virtuous Cycle Framework – Customer at the top, supported by "high purpose, high performance, high people" culture. "It's an 'and,' not an 'or'" - you don't get to choose just one element.
• Back-Channeling is Critical – Reference checking happens throughout the entire interview process, not just at the end. "The most important thing is not just front channel... it's all the back channel."
• Values Alignment Over Pure Qualifications – "Go where my values fit and my strengths are valued." Cultural fit becomes the deciding factor in close hiring calls, not competence.
• The Layoff Leadership Test – Six weeks after joining, Sukhinder laid off 900 people based on McKinsey benchmarking. Showed consistency between the outside-in analysis presented to the board and transparent communication to employees.
• Portfolio of Bets Strategy – Balance growth, profitability, and customer happiness through diversified initiatives ranging from "safe moves" to "flyers," with clear probability assessments.
• Consistency as Culture Foundation – "Culture means consistency of message and what's important." Authenticity through change, not resistance to change.
• The 10-Slide CEO Interview Deck Framework:
  1. Vision statement (destination in 2-3 years)
  2. Outside-in market analysis
  3. Competitive landscape
  4. SWOT analysis of current position
  5. Five key strategic moves
  6. Implementation approach ("the how")
  7. Estimated outcomes with probability ranges
• Practical Application:
  • Job Search Strategy – Define 4-5 non-negotiable criteria upfront. Be willing to wait for roles that truly meet your standards rather than taking "the job before the job."
  • Interview Preparation – Always build a comprehensive thesis deck even if not requested. Use it to clarify your own thinking and demonstrate strategic capability.
  • Hiring Excellence – Spend equal time selling the opportunity and evaluating candidates. Use diverse interview panels and back-channel extensively throughout the process.
  • Cultural Leadership – Be consistent in messaging across all stakeholders (board, investors, employees). Authenticity enables trust during periods of change.
  • Strategic Planning – Frame initiatives as a portfolio of bets with clear probability assessments. Balance growth, profitability, and customer satisfaction rather than optimizing for one.
• Leadership Hiring Process:
  • The CEO interviews top 2-3 levels even without hiring authority
  • Diverse interviewer panels with "bar raisers"
  • Business problem-solving presentations in the final rounds
  • Multiple leadership team interactions before the final decision
• Life Lessons:
  • Patience in Career Progression – Sometimes the right opportunity requires waiting. Sukhinder was frustrated during 18 months of searching but found the perfect fit.
  • Preparation Separates Candidates – The depth of strategic thinking demonstrated in final presentations often determines CEO selections.
  • Culture Survives Through Consistency – Not avoiding change, but maintaining consistent values and communication approach through inevitable changes.
  • Leadership Requires Tough Decisions – Laying off 900 people six weeks into the role, but doing it transparently and based on clear data/analysis.
  • Value Creation Through Alignment – Finding roles where your strengths are valued and values align creates exponentially better outcomes than pure skill matching.
  • Systems Thinking Builds Trust – Sharing appropriate "behind the scenes" context helps teams understand difficult decisions and builds long-term credibility.
  • Early Career Focus – "Do great work for great people." Find talented leaders to apprentice under and work exceptionally hard to maximize learning.
  • Authenticity Enables Performance – Being genuine about challenges and changes builds stronger relationships than trying to maintain artificial stability.
  • Strategic Communication – Frame personal asks in terms of organizational benefits. Make it about solving their problems, not your desires.
• The Xero Transformation:
  • Financial Performance: $2.1B revenue, 21% YoY growth while maintaining profitability
  • Cultural Approach: "High purpose, high performance, high people" - no choosing between them
  • Strategic Moves: Pricing/packaging optimization, sales motion transformation, customer experience reimagining (new dashboard with 3000+ customer inputs)
  • Leadership Philosophy: Provide a "systems view" to employees, share investor-level insights appropriately, and maintain authenticity during difficult decisions