The Heart of Entrepreneurship
Entrepreneurship is about more than your income statement.
10
The Psychology of Motivation No One Taught You
<p>Do you secretly believe success has to come with suffering?<br>In this episode, Jesse Pujji and Dave Kashen challenge one of the most deeply ingrained beliefs in entrepreneurship — that ambition, achievement, and peace can’t coexist. They explore what it means to shift from dirty fuel (fear, lack, and self-criticism) to clean fuel (love, creativity, and flow). From the myth of “losing your edge” to the fear of being lazy without pressure, they break down how founders can grow their companies from joy instead of pain — and why that’s actually more effective.</p><p>✅ Are you bootstrapping? You need this...
Lonely at the Top: Why Success Can Still Feel Empty
<p>Lonely at the Top: How Success Can Disconnect Founders From Themselves</p><p>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.</p><p>This sparks a raw, personal conversation about ego, identity, self-worth, and the invisible emotional toll of entrepreneurship. From the "drama triangle" to the belief that success = love, this episode cuts deep—and offers a path out.</p><p>✅ Are yo...
What Happens When You Move Beyond the Ego
<p>What if your biggest source of stress… is your own mind?</p><p>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 feeling fulfilled. If you’ve ever found yourself anxious despite "winning," this episode is for you.</p><p>✅ Are you bootstrapping? You need this:<br>https://bootstrappedgiants.com/subscribe</p><p>✅ Master the Inner Game of Entrepreneurship here:<br>https://www.davekashen...
Anger Is a Compass: How Founders Turn Emotion into Clarity
<p>Anger as a Compass: How Founders Can Use Emotion to Set Clearer Boundaries and Make Better Decisions</p><p>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?</p><p>In this episode of The Heart of Entrepreneurship, Jesse and Dave explore how anger, when processed healthily, becomes one of the most powerful tools a founder can access. From radical candor to ruinous empathy, they break down why many leaders either over-express or completely shut down their anger—and how that blo...
Why Following Aliveness Might Be the Smartest Business Move
<p>How to Follow What Makes You Feel Alive (Even If It Makes No Logical Sense)</p><p>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?</p><p>In this episode, Jesse and Dave dive into the deeper layers of what it means to follow your aliveness—the felt sense of energy, joy, and presence that can guide your most aligned decisions in work and life.</p><p>✅ Are you boot...
When You Don’t Know What’s Next – You’re Expanding and Growing
<p>Ever feel stuck as a founder—uncertain about your next move, paralyzed by fear, or second-guessing what you really want?</p><p>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 powerful guides, they show how getting unstuck is less about finding the “right” answer and more about trusting your wants, welcoming your emotions, and embracing uncertainty.</p><p>✅ Are you bootstrapping? You need this:<br>https://bootstrappedgiants.com/subscribe<br><br>✅ Master the In...
Why Even Billionaires Still Don’t Feel Safe
<p>Can you build a wildly successful company without sacrificing heart?</p><p>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 rooted in love, freedom, and authenticity rather than fear and scarcity.</p><p>✅ Are you bootstrapping? You need this:<br>https://bootstrappedgiants.com/subscribe</p><p>✅ Master the Inner Game of Entrepreneurship here:<br>https://www.davekashen.com/newsletter-sign-up</p><p>⏱️ Episode Guide<br>...
Beyond Success: Gagan Biyani’s Inner Journey Building Udemy, Sprig, and Maven
<p>What does it take to build, lose, and rebuild as an entrepreneur—while staying true to yourself?</p><p>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 moving beyond pain-driven motivation.</p><p>✅ Are you bootstrapping? You need this:<br>https://bootstrappedgiants.com/subscribe<br><br>✅ Master the Inner Game of Entrepreneurship here:<br>https://www.davekashen.com/newsletter-sign-up</p><p>⏱️ Episode Outline<br>[00:00:00] Intro – Dave opens with gratitude and sets up Gagan’s j...
How to Change Without Willpower, Guilt, or Discipline
<p>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 change without guilt and willpower battles.</p><p>✅ Are you bootstrapping? You need this:<br>https://bootstrappedgiants.com/subscribe</p><p>✅ Master the Inner Game of Entrepreneurship here:<br>https://www.davekashen.com/newsletter-sign-up</p><p>⏱️ Episode Outline<br> 00:00 – Intro: Jesse’s fitness journey and “yo-yo” behavior<br>...
The Parts You Reject Are Blocking Your Potential
<p>Why You Resist Feeling Bad (And How It Holds You Back as a Founder)</p><p>✅ Are you bootstrapping? You need this:<br>https://bootstrappedgiants.com/subscribe</p><p>✅ Master the Inner Game of Entrepreneurship here:<br>https://www.davekashen.com/newsletter-sign-up</p><p>00:00 – Intro + today's topic: “shadows” and the parts we deny<br> 01:30 – Jesse’s shadow: the victim<br> 03:00 – Why founders avoid “weak” emotions like sadness, shame, helplessness<br> 05:00 – What’s the point of all this inner work? (Andrew challenges the premise)<br> 06:30 – Peace vs. success: what are founders really after?<br> 08:00 – Resistance is what drains you, not action<br> 09:30 – Integrati...
