The Heart of Entrepreneurship

Lonely at the Top: How Success Can Disconnect Founders From ThemselvesWhat 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.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.✅ Are you bootstrapping? You need this:https://bootstrappedgiants.com/subscribe✅ Master the Inner Game of Entrepreneurship here:https://www.davekashen.com/newsletter-sign-up⏱️ Episode Breakdown00:00 – Brian Chesky’s viral post: loneliness after $100B success02:50 – Loneliness at the top: why success doesn’t equal being loved06:00 – The perfect life you’re not living: founder stuck in grind08:00 – Authenticity, masks, and leadership loneliness11:00 – Selfish entrepreneurship and the cost of success13:30 – Founders and identity: “This is me” vs. the business17:00 – Vulnerability in leadership: openness builds trust20:45 – Imposter syndrome: you’re supposed to be an imposter22:45 – Dirty fuel vs. clean fuel: compulsion vs. presence24:30 – Fear vs. love isn’t binary—lead with heart and strength26:45 – Are you contracted or expanded? A body-based check-in30:00 – Do you wish things were different? Resistance = suffering33:18 – The Drama Triangle explained: Victim, Villain, Hero36:15 – How to spot the triangle in yourself (and your team)39:00 – Once you see it, you can’t unsee it42:00 – Drama triangle in relationships and leadership44:00 – Tactical tool: write down the triangle to gain clarity46:00 – Responsibility and empowerment: the way out48:00 – Founder conflict example: pipeline report frustration52:00 – Unconscious worldviews that reinforce the drama53:30 – Final challenge: notice the story loops and reclaim your power🧠 What You’ll Learn• How ego traps founders in loneliness and inauthenticity• What the “Drama Triangle” is and how to escape it• The truth about self-worth, identity, and high achievement• Why imposter syndrome is a feature, not a bug• How to stay open-hearted and fierce as a leader• Practical ways to shift from blame to ownership—and get unstuck fastIf you’ve ever hit a big goal only to feel… hollow… this conversation will make you feel seen—and give you the tools to reorient toward wholeness.💬 Let us know in the comments: which role do you default to—Victim, Villain, or Hero? 👍 Like this episode if it gave you clarity. 🔔 Subscribe for more emotionally intelligent conversations on leadership and entrepreneurship.#EmotionalIntelligence #FounderBurnout #LeadershipGrowth

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 feeling fulfilled. If you’ve ever found yourself anxious despite "winning," this episode is for you.✅ Are you bootstrapping? You need this:https://bootstrappedgiants.com/subscribe✅ Master the Inner Game of Entrepreneurship here:https://www.davekashen.com/newsletter-sign-up⏱ Episode Breakdown: 00:00 – What ego really means (not just arrogance) 02:00 – Ego as “sense of self” and why it feels limiting 05:00 – How ego creates internal conflict and suffering 09:00 – The mind as a storyteller obsessed with problems 14:30 – Identity, impermanence, and the illusion of control 20:00 – The founder trap: tying self-worth to startup success 26:00 – Why even after $10M exits, founders feel unfulfilled 33:00 – The ego's role in chasing happiness vs. feeling it 39:00 – “You are not your thoughts” — the essential self 42:00 – Meditation, awareness, and ego detachment tactics 48:00 – Identifying and disarming ego patterns in real time 52:00 – The founder archetype without ego-driven stress 56:00 – Final story: Playing business like a game (Monopoly mindset)💡 What You’ll Learn:• A deeper definition of ego as your mental “self-concept”• How ego shapes your suffering, even in success• The science and spirituality of detaching from identity• Meditation tips for founders (that actually work)• Practical frameworks to see your thoughts clearly and respond with presence, not reactivity• How top founders stay grounded, calm, and joyful—even in chaosKeywords:ego and entrepreneurship, startup mindset, detaching from ego, founder identity, mental clarity, spiritual growth for business, mindfulness for founders, coaching for entrepreneurs, startup success mental health, playing the game of business, mindfulness practices, dealing with startup stress, inner critic awareness, founder therapy, meditation for productivity, mental masteryLet us know in the comments: 👉 What ego pattern do you most relate to? If this helped you shift your mindset, like & subscribe for more grounded conversations on building and leading from the heart.#HeartOfEntrepreneurship #FounderMindset #EgoAndBusiness

Anger as a Compass: How Founders Can Use Emotion to Set Clearer Boundaries and Make Better DecisionsMost 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 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 blocks clarity, boundaries, and momentum.Whether you’re the type to explode or the type who “never gets mad,” this is a conversation you won’t want to miss.✅ Are you bootstrapping? You need this:https://bootstrappedgiants.com/subscribe✅ Master the Inner Game of Entrepreneurship here:https://www.davekashen.com/newsletter-sign-up⏱️ Timestamps 00:00 – Intro: Why anger is an important topic for founders 01:12 – Steve Jobs archetype vs modern leadership norms 02:00 – Jesse’s personal journey with expressing anger 03:00 – Radical Candor framework: Obnoxious Aggression vs Ruinous Empathy 05:00 – Why most leaders are stuck in the “too nice” trap 06:00 – Cultural beliefs around anger and being “uncivilized” 08:00 – Dave’s relationship story: what healthy anger actually looks like 10:21 – What is anger, really? Anger as the energy of boundaries 13:00 – The difference between disappointment and anger 16:00 – Repressing vs expressing: how anger leaks out when suppressed 18:00 – Safe, healthy ways to move anger through your body 20:00 – Teaching kids how to work with their own anger 22:00 – Why anger is often directed at others (and how to break that pattern) 24:00 – When anger is misused: violence, fear, and repression 26:00 – Depression as repressed anger at self 27:00 – Jesse and Dave’s personal examples of using anger constructively 30:00 – Anger as a signal for boundaries and internal clarity 32:00 – Healthy boundaries that help you keep your heart open 34:00 – A founder’s guide to anger: what to do instead of blowing up 35:00 – Why anger helps you know what you actually want 38:00 – Clarity comes from letting anger move 39:00 – Wanting a high-commitment culture? You need anger to get clear 41:00 – Step-by-step: how to feel, welcome, and express anger 44:00 – Sadness vs anger: different repressions, different fears 46:00 – For those who explode: how to stop projecting and start revealing 49:00 – Leaders: why simply saying what you want is so powerful 51:00 – Final takeaway: anger is your compass for knowing what you truly want🧠 What You’ll Learn:• The 4-step process for working with anger (identify → welcome → express → set a boundary)• Why founders who repress anger often feel unclear or indecisive• The difference between expressing anger at someone vs revealing it responsibly• Practical ways to process anger without harming relationships• How anger helps you access clarity, confidence, and leadership alignmentAnger isn’t the enemy—it’s a message. And for founders building from the heart, it can be the difference between burnout and breakthrough. Listen in to learn how to use it wisely.👍 If this resonated, give it a like. 💬 Share your experience with anger in the comments. 🔔 Subscribe for more emotionally intelligent leadership conversations.#emotionalintelligence #foundermindset #leadershipdevelopment

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 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.✅ Are you bootstrapping? You need this:https://bootstrappedgiants.com/subscribe✅ Master the Inner Game of Entrepreneurship here:https://www.davekashen.com/newsletter-sign-up⏱️ Timestamps 00:00 – Intro: What does “aliveness” actually mean? 01:30 – Jesse’s obsession with a new idea and Dave’s cliff-jumping retreat 04:00 – Defining aliveness as a physical, felt experience 06:00 – Are you living half-dead? The cost of ignoring your aliveness 08:00 – Jesse’s examples: business creation, childbirth, deep meditation 10:00 – Flow state, spiritual presence, and the power of “now” 13:00 – Connection, awe, and presence in small everyday moments 15:00 – Anti-patterns: what blocks aliveness in founders 17:00 – Jesse’s client story: heroing the team vs. enjoying the job 19:00 – Survival patterns vs authentic action 21:00 – Why we fear feelings more than outcomes 23:00 – Dave’s coaching distinction: “the right answer” vs. “what feels right” 25:00 – The trick of discerning fear from intuitive truth 27:00 – Why overthinking is a signal you’re disconnected from self 29:00 – Conscious Leadership’s 4 pillars of integrity (unfelt feelings, unkept agreements, etc.) 32:00 – How unspoken truths and misaligned agreements leak energy 34:00 – Redefining empowerment: authenticity despite consequences 36:00 – The difference between fear as fuel vs. fear as signal 38:00 – Shame, guilt, and the hidden drivers of success 41:00 – Outcome detachment + aliveness = surprising success 43:00 – Can you follow joy and succeed wildly? 44:00 – Final question: What are you willing to risk for your full aliveness?🎧 What You’ll Learn:• How to recognize and follow your sense of aliveness• Why fear and shame often block flow and authenticity• The “invisible” cost of ignoring your body’s signals• Practical ways to get back into alignment when you’re stuck• How founders can lead and build from presence, not pressureThis conversation is for any founder, creator, or leader who’s ready to live and work in deeper alignment. If you’ve ever felt stuck, burned out, or disconnected from your spark—this episode is a must-listen.💬 What makes you feel most alive? Drop it in the comments. And don’t forget to like & subscribe for more grounded, no-BS conversations on leadership, growth, and inner work.#foundermindset #emotionalintelligence #authenticleadership

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 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.✅ Are you bootstrapping? You need this:https://bootstrappedgiants.com/subscribe✅ Master the Inner Game of Entrepreneurship here:https://www.davekashen.com/newsletter-sign-up⏱️ Episode Guide[00:00:00] Opening – Why this podcast is about building with heart, not just grinding [00:01:03] 10 problems vs. 10,000 blessings: gratitude framing [00:02:33] Why founders rarely admit when they feel stuck [00:03:27] “Growing edge” reframing – stuckness as a sign of expansion [00:04:21] The genius trap: frustration when things don’t come easy [00:05:24] Expecting to know vs. embracing “I don’t know” [00:07:03] Rick Elias’ billion-dollar lesson: “We have no clue what we’re doing” [00:08:06] Liberation in curiosity and beginner’s mind [00:09:36] Fear as a hidden driver of stuckness [00:10:48] Avoidance disguised as time management [00:12:00] Clarity, murky water, and letting stillness reveal the path [00:15:18] The unknowable nature of “right” answers [00:17:42] Persistence vs. letting go – when forcing success backfires [00:21:00] Why humans cling to certainty [00:23:06] Capacity to handle uncertainty vs. obsession with being right [00:25:12] Founders, hedge funds, and separating “being” from “doing” [00:27:27] Knowing what you want vs. chasing the “right” answer [00:29:24] Rebuilding the muscle of wanting [00:31:03] Founder desires and strategy: why “want” drives company success [00:33:09] Founder energy as the real determinant of persistence [00:34:21] Why people don’t trust their wants (worthiness, work ethic, trade-offs) [00:36:54] “What would have to be true?” reframing conflicting desires [00:40:03] Anger as a signal for boundaries and wants [00:42:00] Welcoming fear instead of resisting it [00:43:39] Stuckness as resisting emotion in the body [00:46:21] Fear-based motivation and why letting go doesn’t kill drive [00:48:00] Magical thinking: fear won’t manifest reality [00:49:57] Final challenge – run the experiment: feel the fear fullyWhat You’ll Learn• Why feeling stuck is often a sign you’ve reached your growth edge.• How to use “I don’t know” as a catalyst for curiosity and action.• Practical ways to build your “wanting muscle” and trust what you truly desire.• Why resisting fear, anger, or uncertainty keeps you stuck—and how welcoming them unlocks clarity.• A founder-friendly framework for balancing persistence with the courage to let go.In this Heart of Entrepreneurship episode, Jesse Pujji and coach Dave Kashen dive into one of the most common but rarely discussed founder challenges: feeling stuck. They explore frameworks from conscious leadership, beginner’s mind, and emotional intelligence to show how fear, uncertainty, and suppressed wants are often the real culprits behind stagnation.If you’re navigating tough decisions, wondering about the “right” strategy, or struggling with founder energy, this conversation will help you reframe stuckness as growth. You’ll hear stories about billion-dollar CEOs, the genius trap, and why authentic wants matter more than market math.Perfect for anyone interested in startup strategy, leadership frameworks, founder mindset, and emotional resilience.What’s your experience of being stuck as a founder? Share it in the comments—we’d love to hear. Don’t forget to like this episode if it helped shift your perspective, and subscribe for more deep-dive conversations with Jesse, Andrew, and Dave on The Heart of Entrepreneurship.#HeartOfEntrepreneurship #FounderMindset #ConsciousLeadership

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 rooted in love, freedom, and authenticity rather than fear and scarcity.✅ Are you bootstrapping? You need this:https://bootstrappedgiants.com/subscribe✅ Master the Inner Game of Entrepreneurship here:https://www.davekashen.com/newsletter-sign-up⏱️ Episode Guide[00:00:00] Opening thoughts – Why Jesse and Dave love doing the podcast [00:01:30] Recap of last week’s conversation with Gagan Biyani (Udemy, Maven, Sprigg) [00:03:00] Defining success: impact vs. numbers [00:04:03] Ambition with heart – what kind of world are we building? [00:05:24] AI, consciousness, and the future of leadership [00:06:00] Jesse’s story: life after Ampush and unexpected anxiety [00:07:21] Introducing the Sedona Method [00:08:42] Security, control, and approval – the “big three” human needs [00:12:09] Why external success doesn’t create inner security [00:16:12] Jesse’s exit story: wealth, scarcity, and the Aston Martin dilemma [00:18:27] The elusive feeling of “enough” [00:21:00] What we’re really talking about when we say “security” [00:23:15] Control, presence, and the Serenity Prayer [00:27:27] Wants vs. needs – the Range Rover story [00:30:00] Impulse vs. compulsion in entrepreneurship [00:34:30] Play vs. seriousness – how attachment kills creativity [00:35:15] Practice: Can you enjoy the wanting? [00:36:00] Guided Sedona Method practice – welcoming security, control, and approval [00:43:39] Self-improvement vs. self-discovery [00:45:00] Head vs. heart – acceptance through presence [00:46:12] Essential self vs. identity [00:47:15] Closing thoughts & resources on the Sedona MethodWhat You’ll Learn• Why chasing money, status, or influence rarely leads to true safety or fulfillment.• The difference between authentic wants and compulsive attachments.• How the Sedona Method helps founders let go of fear and reconnect with their essential self.• Practical ways to approach business with both ambition and heart.Entrepreneurship isn’t just about scaling fast and hitting milestones—it’s also about how you build. In this conversation, Jesse Pujji and Dave Kashen unpack the Sedona Method and the 15 Commitments of Conscious Leadership, linking them directly to the realities of startup life. From exits and scarcity mindset to identity and approval, they reveal why many founders never feel “enough”—and how to break free of that cycle.If you’re exploring branding 101, conscious leadership, or building a startup strategy rooted in wellbeing, this episode is for you. It’s a masterclass in balancing ambition and authenticity, growth and groundedness, and success and soul.We’d love to hear your reflections—have you ever chased security or approval in your entrepreneurial journey? Drop a comment, like the video if it resonates, and don’t forget to subscribe for more deep-dive conversations with Jesse, Andrew, and Dave on The Heart of Entrepreneurship.#HeartOfEntrepreneurship #ConsciousLeadership #FounderMindset

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 moving beyond pain-driven motivation.✅ Are you bootstrapping? You need this:https://bootstrappedgiants.com/subscribe✅ Master the Inner Game of Entrepreneurship here:https://www.davekashen.com/newsletter-sign-up⏱️ Episode Outline[00:00:00] Intro – Dave opens with gratitude and sets up Gagan’s journey [00:01:57] Gagan’s early story: middle-class upbringing, parents’ split, first business at 13 [00:04:12] Lessons from speech & debate and bootstrapping a youth camp [00:05:24] Frustration with education system and early path to entrepreneurship [00:07:03] Founding Udemy – excitement, clashes, and a painful co-founder exit [00:09:00] The reality of co-founder departures and why they’re more common than people admit [00:12:00] Founder guilt and the challenge of letting go of employees [00:16:03] Why firing faster often strengthens culture and execution [00:19:03] Baseball as a metaphor for hiring “batting averages” [00:23:06] Pain-driven motivation, control, and lessons from Sprig’s collapse [00:29:33] Building and losing control: Sprig as an early “ghost kitchen” [00:36:45] Macro risk, timing, and luck in startups vs. smaller businesses [00:44:06] Comparison traps—Bezos, Chesky, and the illusion of “proving it” [00:49:30] Shifting the burden of proof and redefining success after failure [00:52:51] Relief after shutting down Sprig and finding freedom [00:56:06] Travel, self-discovery, and learning to separate identity from achievement [01:05:06] Learning to love yourself without external labels [01:08:06] Resisting joy and gratitude as much as pain [01:11:06] Why inner work matters for founders—and how it changes execution and team retention [01:15:00] Closing reflections on investing in personal growth💡 What You’ll LearnWhy co-founder departures are far more common than founders admitHow to reframe letting go of employees as an act of alignment, not failureThe trap of pain-driven motivation and how to shift beyond itWhy timing, luck, and macro forces matter more than pure talentHow self-discovery and inner work fuel long-term entrepreneurial success📌 About This EpisodeThis is not just another “startup success” story—it’s a raw, honest look at the heart of entrepreneurship. Gagan and Dave dig into the messy human side of building companies: the guilt of firing, the relief of shutting down, the burden of comparison, and the deep work needed to move from proving yourself to living authentically.If you’re a founder, this conversation blends practical insights on leadership and hiring with emotional wisdom about resilience, identity, and growth. Think of it as both startup strategy and personal development 101.🙌 Stay ConnectedIf this episode resonated, let us know in the comments. Don’t forget to like, subscribe, and share with a fellow entrepreneur who needs to hear this.#HeartOfEntrepreneurship #StartupLessons #FounderJourney

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.✅ Are you bootstrapping? You need this:https://bootstrappedgiants.com/subscribe✅ Master the Inner Game of Entrepreneurship here:https://www.davekashen.com/newsletter-sign-up⏱️ Episode Outline 00:00 – Intro: Jesse’s fitness journey and “yo-yo” behavior 03:00 – The guilt loop and resisting change 06:30 – Counter-will: why we rebel against ourselves 10:00 – Shame, guilt, and the myth of “just push harder” 13:00 – Why external success doesn’t equal lasting happiness 17:00 – Experiment: letting go of needing things to change 20:00 – The trap of “when I have this, then I’ll feel good” 24:00 – Cultural roots of shame and self-discipline 27:00 – Shame as the blocker of emotional flow 29:00 – Dave’s “ice cream loop” and welcoming shame 32:00 – Find the emotion behind the habit 33:00 – Using cost-benefit analysis for self-awareness 35:00 – Breaking out of binary thinking (micromanager vs. hands-off) 39:00 – Why shame blocks real change 43:00 – Childhood patterns that carry into adulthood 45:00 – 3 tools for real change:   • Welcome the shame   • Identify the underlying emotion   • Run small, discipline-free experiments 49:00 – Behavior design: making it easier to do the right thing 53:00 – Funny story: the “ice cream safe” (and surprise savings bonds!) 55:00 – Final recap and takeaways🎧 What you’ll learn: • Why “shoulding” yourself leads to burnout and inconsistency • How shame secretly keeps bad habits in place • The difference between willpower and true choice • How to make meaningful change through experiments, not extremes • Why welcoming your feelings (even shame) opens up freedomIf you’re a founder, leader, or anyone trying to break free from burnout loops, this episode will give you mindset tools to grow from love, not fear. A must-listen for anyone navigating growth, ambition, and self-acceptance.💬 Let us know your biggest takeaway in the comments, and don’t forget to like & subscribe!#entrepreneurship #selfgrowth #heartofentrepreneurship

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-up00:00 – Intro + today's topic: “shadows” and the parts we deny 01:30 – Jesse’s shadow: the victim 03:00 – Why founders avoid “weak” emotions like sadness, shame, helplessness 05:00 – What’s the point of all this inner work? (Andrew challenges the premise) 06:30 – Peace vs. success: what are founders really after? 08:00 – Resistance is what drains you, not action 09:30 – Integration vs. high: wholeness as the goal 11:30 – “If you can’t be happy now, you won’t be happy then” 12:30 – The cost of repressing emotion: risk aversion, stuckness 15:00 – “Who would I be if I weren’t afraid to fail?” 17:00 – The loser shadow: Dave’s story 18:30 – How founders self-limit by avoiding identity threats 21:00 – What is a shadow? (The theory) 23:00 – Projection, judgment, and your hidden parts 25:00 – Accepting reality vs. resignation 27:00 – Reality distortion field vs. future vision 29:00 – Why fear of being a fraud stops growth 30:30 – How acceptance leads to effective action 33:00 – The power of admitting doubt 34:30 – Jesse’s pitch vs. Andrew’s pitch: truth builds trust 36:00 – Authenticity, vulnerability, and leadership 37:00 – Self-awareness is a prerequisite to shadow work 38:00 – Self-discovery vs. self-improvement 40:00 – How to find your shadow: what irritates you in others? 42:00 – Andrew’s trigger: negativity and complaining 44:00 – What to do with your shadow (practical exercises) 46:00 – Persona party, exaggeration, and expression 48:00 – Final thoughts and experiment: 5 daily complaintsWhat You’ll Learn:In this episode, Jesse, Dave, and Andrew dive deep into the uncomfortable but transformative topic of shadow work—the parts of ourselves we deny, repress, or judge.Through personal stories, coaching insights, and practical tools, they explore how repressed emotions and rejected traits can silently run the show—impacting leadership, risk tolerance, decision-making, and personal peace.You’ll learn:What “shadow” means and how to recognize it in yourselfHow repressing certain traits (e.g. victimhood, negativity) limits successWhy denying uncomfortable emotions causes energy drainHow to use judgment and projection to identify your shadowsPractical exercises to express, accept, and integrate the parts you resistWhy self-awareness and radical acceptance unlock freedom and flowThis episode of Heart of Entrepreneurship breaks down the hidden patterns that affect how founders lead, relate, and create. Through the lens of shadow work, Jesse, Dave, and Andrew unpack how repressing emotions like fear, sadness, shame, or doubt keeps entrepreneurs stuck in reactive cycles and blocks real growth.They cover concepts from Internal Family Systems (IFS), offer real-life founder coaching examples, and deliver a toolkit for building emotional resilience, behavioral flexibility, and founder authenticity.Whether you’re exploring emotional intelligence, recovering from burnout, or trying to take your leadership to the next level, this episode is both raw and actionable.Thanks for listening. If this resonated, leave a comment with your own shadow, hit like, and subscribe for more honest conversations about what it really takes to grow as a founder.#shadowwork #founderjourney #emotionalintelligence

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-up00:00 – Intro: Dave’s coaching lineage + the Groundbreakers retreat01:30 – Why even high-performing founders need constant inner work 03:00 – Dave’s perspective on “problems” vs. learning patterns 04:30 – First breakthrough: befriending the voice in your head 06:30 – How feelings unlock clarity (not block it) 08:00 – Why exercises over just insights in personal growth 09:30 – “Unfelt feelings are the glue” – Tara’s insight on stuck patterns 11:00 – Dave’s top takeaways from Joe Hudson’s Masterclass 12:30 – The 7 core mindset shifts explained: 15:30 – Real-life sales example: Jesse on objections and trust 18:30 – Dave’s “motorboat vs. sailboat” analogy for leadership energy 21:00 – Kids, walking, and letting life flow (vs. over-managing) 23:30 – Enjoying even hard tasks (like taxes!) 25:00 – Tactical tip: open your heart to feel more joy now 27:00 – Emotional decision-making vs. rationalization 29:30 – Spouse fights, ice cream, and clarity after feeling 32:00 – Jesse’s Growth Assistant story: AI direction driven by want 34:00 – How trusting your team’s authentic wants creates better outcomes 36:00 – Radical idea: you don’t need to improve to grow 38:30 – What you’d have to give up to feel peace without improving 40:30 – The power of authenticity, empowerment, and openness 42:30 – Final thoughts and reflectionsWhat You’ll Learn:In this powerful episode, Jesse and Dave go deep into the 7 mindset shifts from Joe Hudson’s Art of Accomplishment masterclass—principles that can radically reshape how you lead, decide, grow, and relate to others.Whether you’re burned out from over-managing, stuck in self-improvement loops, or craving more ease in your entrepreneurial journey, this conversation offers a grounded, embodied approach to leadership and growth.You’ll learn:Why connection and enjoyment matter more than perfectionHow to feel your way to clarity instead of forcing decisionsHow embracing your wants leads to better alignment and motivationWhy authenticity drives more sustainable improvement than disciplineThe secret to empowering others (and yourself)How to lead with love, not defenseThis episode of Heart of Entrepreneurship is a masterclass in founder mindset transformation. Drawing from Joe Hudson’s Art of Accomplishment, Jesse and Dave unpack how to lead from a place of presence, authenticity, and emotional intelligence—rather than fear, pressure, or performance.They explore core principles like “Enjoy over Manage” and “Connection over Perfection,” using real-life examples from sales, coaching, and company building. You’ll hear how emotional awareness, internal alignment, and letting go of control can actually make you more effective—and more fulfilled.Whether you're deep into self-awareness practices, building a startup, or leading a team, these mindset shifts will challenge and inspire you.Like this episode? Comment with the shift that resonated most with you. Don’t forget to hit like and subscribe for more grounded conversations on growth and leadership.#foundermindset #emotionalintelligence #leadershipskills