Best Dave Kashen Podcasts (2025)

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Lonely at the Top: Why Success Can Still Feel Empty 53:59

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8d ago53:59

53:59

Lonely at the Top: How Success Can Disconnect Founders From Themselves What if chasing success actually makes you feel less fulfilled? In this episode, Jesse and Dave unpack Brian Chesky’s viral reflection on the loneliness he felt after Airbnb's $100B IPO. Despite achieving the dream, he felt disconnected, empty, and unsure of how he got there. Th…

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What Happens When You Move Beyond the Ego 58:18

6d ago58:18

58:18

What if your biggest source of stress… is your own mind? In this episode of Heart of Entrepreneurship, Jesse and Dave unpack the concept of ego—not as arrogance, but as the mental identity we all unconsciously carry. They explore how identifying with your thoughts creates suffering, limits your potential, and keeps even successful founders from fee…

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Anger Is a Compass: How Founders Turn Emotion into Clarity 51:50

13d ago51:50

51:50

Anger as a Compass: How Founders Can Use Emotion to Set Clearer Boundaries and Make Better Decisions Most entrepreneurs are taught to suppress anger—or worse, use it as a weapon. But what if anger isn’t something to avoid… but something to listen to? In this episode of The Heart of Entrepreneurship, Jesse and Dave explore how anger, when processed …

1
Why Following Aliveness Might Be the Smartest Business Move 44:26

1M ago44:26

44:26

How to Follow What Makes You Feel Alive (Even If It Makes No Logical Sense) You’ve probably heard advice like “follow your passion” or “do what lights you up”—but how do you actually do that in practice as a founder? And how do you know when you’re following aliveness vs fear or performance? In this episode, Jesse and Dave dive into the deeper laye…

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When You Don’t Know What’s Next – You’re Expanding and Growing 50:27

1M ago50:27

50:27

Ever feel stuck as a founder—uncertain about your next move, paralyzed by fear, or second-guessing what you really want? In this episode, Jesse Pujji and Dave Kashen unpack the hidden dynamics behind “stuckness” and how founders can transform it into growth. From reframing “I don’t know” as liberation, to uncovering fear, anger, and desire as power…

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Why Even Billionaires Still Don’t Feel Safe 47:26

1M ago47:26

47:26

Can you build a wildly successful company without sacrificing heart? In this episode, Jesse Pujji and Dave Kashen dive deep into the Sedona Method—a powerful practice for letting go of the endless chase for security, control, and approval. They share personal stories about money, identity, and ambition, and explore how founders can build businesses…

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Beyond Success: Gagan Biyani’s Inner Journey Building Udemy, Sprig, and Maven 1:15:38

2M ago1:15:38

1:15:38

What does it take to build, lose, and rebuild as an entrepreneur—while staying true to yourself? In this conversation, host Dave Kashen sits down with Gagan Biyani (co-founder of Udemy, Sprig, and Maven) to explore the emotional and practical realities of entrepreneurship: co-founder dynamics, letting go of team members, navigating failure, and mov…

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How to Change Without Willpower, Guilt, or Discipline 56:08

2M ago56:08

56:08

Ever find yourself stuck in a cycle of self-discipline, shame, and yo-yo habits? In this episode of Heart of Entrepreneurship, Jesse and Dave dive deep into the psychology behind personal growth—and why punishing yourself into change doesn’t actually work. From fitness routines to leadership patterns, they explore how to unlock lasting behavior cha…

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The Parts You Reject Are Blocking Your Potential 48:18

2M ago48:18

48:18

Why You Resist Feeling Bad (And How It Holds You Back as a Founder) ✅ Are you bootstrapping? You need this: https://bootstrappedgiants.com/subscribe ✅ Master the Inner Game of Entrepreneurship here: https://www.davekashen.com/newsletter-sign-up 00:00 – Intro + today's topic: “shadows” and the parts we deny 01:30 – Jesse’s shadow: the victim 03:00 –…

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How Enjoyment (Not Hustle) Drives Real Growth 47:51

3M ago47:51

47:51

7 Inner Shifts That Make You a Better Leader (Without Forcing It) ✅ Are you bootstrapping? You need this: https://bootstrappedgiants.com/subscribe ✅ Master the Inner Game of Entrepreneurship here: https://www.davekashen.com/newsletter-sign-up 00:00 – Intro: Dave’s coaching lineage + the Groundbreakers retreat 01:30 – Why even high-performing founde…

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The Personas Playing You: How Founders Get Trapped in Drama & Identity 55:21

2M ago55:21

55:21

The Personas Playing You: How Founders Get Trapped in Drama & Identity ✅ ARE YOU BOOTSTRAPPING? YOU NEED THIS: https://bootstrappedgiants.com/subscribe ✅ Master the Inner Game of Entrepreneurship here: https://www.davekashen.com/newsletter-sign-up Show Notes: 00:00 – Intro + why entrepreneurship doesn’t have to be painful 01:30 – What is a persona?…

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Why Unfelt Feelings Become a Prison for Founders 50:28

3M ago50:28

50:28

What Are You Resisting? How Founders Block Growth by Avoiding Emotion ✅ ARE YOU BOOTSTRAPPING? YOU NEED THIS: https://bootstrappedgiants.com/subscribe ✅ Master the Inner Game of Entrepreneurship here: https://www.davekashen.com/newsletter-sign-up Show Notes: 00:00 – Intro + recap: resisting emotions, what it means for founders 02:00 – Why emotions …

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The Answers Are Hiding in Your Repressed Emotions 48:13

4M ago48:13

48:13

Emotions Are Not the Enemy: Unlocking Leadership, Clarity & Decision-Making Through Feeling ✅ ARE YOU BOOTSTRAPPING? YOU NEED THIS: https://bootstrappedgiants.com/subscribe ✅ Master the Inner Game of Entrepreneurship here: https://www.davekashen.com/newsletter-sign-up Most entrepreneurs think their emotions get in the way. But what if they’re actua…

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Creative Tension: The Secret to Creating Big Results Without the Grind 51:47

4M ago51:47

51:47

Why do some goals drain you while others inspire action? In this powerful conversation, Jesse Pujji and executive coach Dave Kashen unpack a core concept at the heart of entrepreneurship: the Desired Future State (DFS). They explore how clean motivation, grounded in acceptance and vision—not fear or lack—can transform the way you lead, strategize, …

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Is Spirituality the Missing Key for Founders? 46:37

5M ago46:37

46:37

You're Not Your Inner Voice: Meditation, Spirituality, and Mental Clarity for Founders ✅ ARE YOU BOOTSTRAPPING? YOU NEED THIS: https://bootstrappedgiants.com/subscribe ✅ Master the Inner Game of Entrepreneurship here: https://www.davekashen.com/newsletter-sign-up 00:00 – Jesse introduces the topic: spirituality for entrepreneurs 01:00 – What does s…

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Why You Unknowingly Resist Love, Joy, and Fulfillment 49:42

9M ago49:42

49:42

Most people think they struggle with fear or failure. But the truth is, we’re often more afraid of love, joy, and being fully seen. In this episode, Dave Kashen, Jesse Pujji, and Andrew Warner uncover the hidden ways we resist appreciation, connection, and fulfillment—without even realizing it. They break down why receiving acknowledgment can feel …

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The Secret to Creating Your Dream Life and Business in 2025 51:06

11M ago51:06

51:06

What if the key to creating your dream life and business isn’t about working harder—but about taking radical responsibility for your entire experience, including the belief that it has to be difficult? In this episode, Jesse Pujji, Dave Kashen, and Andrew Warner reveal how entrepreneurs unknowingly create their own overwhelm by holding onto limitin…

1
How Emotions Are Your Decision-Making Compass 56:29

11M ago56:29

56:29

What if the emotions you’ve been avoiding are the key to making better decisions and unlocking your true potential? In this episode, Jesse Pujji, Dave Kashen, and Andrew Warner dive into how emotions like fear, anger, and sadness can guide you to clarity and alignment—if you let them. They explore why resisting emotions creates stress and confusion…

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Outperform Yourself By Breaking Your Upper Limit 49:20

11M ago49:20

49:20

No matter how big your goals are or how much you’ve already achieved, you might have an 'upper limit problem' quietly holding you back. In this episode of The Heart of Entrepreneurship, Jesse Pujji, Dave Kashen, and Andrew Warner dive into the hidden barriers that limit success—even for high achievers. Together, they explore how unconscious beliefs…

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The Limiting Stories Entrepreneurs Tell Themselves—And How to Let Them Go 47:51

12M ago47:51

47:51

Entrepreneurs often chase success by pushing harder and striving for more, but what if the real key lies in rethinking the stories we tell ourselves? In this episode, Jesse Pujji and Dave Kashen share practical exercises to help entrepreneurs separate facts from narratives, freeing them from the things that hold them back––like guilt, regret, and b…

1
Why We're Doing This Podcast 48:44

1y ago48:44

48:44

Jesse Pujji sold a big piece of his company, Ampush. He should have felt "safe" and happy and more productive. It didn't work. He hired Dave Kashen to coach him. That was a huge unlock. It led him to build multiple companies, have a happier family life and embrace his love of teaching. This podcast shows why that happened. And why they're launching…

Dave Kashen Podcasts

1
The Heart of Entrepreneurship

Dave Kashen and Jesse Pujji

1
Lonely at the Top: Why Success Can Still Feel Empty 53:59

1
What Happens When You Move Beyond the Ego 58:18

1
Anger Is a Compass: How Founders Turn Emotion into Clarity 51:50

1
Why Following Aliveness Might Be the Smartest Business Move 44:26

1
When You Don’t Know What’s Next – You’re Expanding and Growing 50:27

1
Why Even Billionaires Still Don’t Feel Safe 47:26

1
Beyond Success: Gagan Biyani’s Inner Journey Building Udemy, Sprig, and Maven 1:15:38

1
How to Change Without Willpower, Guilt, or Discipline 56:08

1
The Parts You Reject Are Blocking Your Potential 48:18

1
How Enjoyment (Not Hustle) Drives Real Growth 47:51

1
The Personas Playing You: How Founders Get Trapped in Drama & Identity 55:21

1
Why Unfelt Feelings Become a Prison for Founders 50:28

1
The Answers Are Hiding in Your Repressed Emotions 48:13

1
Creative Tension: The Secret to Creating Big Results Without the Grind 51:47

1
Is Spirituality the Missing Key for Founders? 46:37

1
Why You Unknowingly Resist Love, Joy, and Fulfillment 49:42

1
The Secret to Creating Your Dream Life and Business in 2025 51:06

1
How Emotions Are Your Decision-Making Compass 56:29

1
Outperform Yourself By Breaking Your Upper Limit 49:20

1
The Limiting Stories Entrepreneurs Tell Themselves—And How to Let Them Go 47:51

1
Why We're Doing This Podcast 48:44