The Heart of Entrepreneurship

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

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-upShow Notes:00:00 – Intro + why entrepreneurship doesn’t have to be painful 01:30 – What is a persona? (And why we mistake it for our true self) 04:00 – The firefighter, the hero, the nice guy, the newscaster mom 06:00 – Playing your persona vs. letting it play you 08:00 – Drama Triangle: Victim, Villain, Hero explained 10:00 – A real founder example: sales team missed quota 12:00 – Why “saving the day” undermines growth 14:00 – How founders create crises just to play hero 16:00 – Resentment: when saving others starts to backfire 18:00 – How these patterns cycle inside one person’s mind 21:00 – Recognizing victimhood, blame, and savior energy 23:00 – Identifying your default persona 25:00 – The lie of “that’s not me” and the power of discomfort 28:00 – Internal Family Systems (IFS) explained 30:00 – The parts inside you: protectors, exiles, managers 32:00 – A real-world IFS coaching example (part of me wants to sell…) 35:00 – Jesse’s parts: anxious achiever, the sad boy, and the protector 37:00 – What every part really wants: safety 39:00 – Embracing the shadow: liar, judge, and critic 42:00 – Self-love and reclaiming “ugly” parts 44:00 – Why entrepreneurs avoid emotions with packed calendars 46:00 – Behavioral flexibility = leadership power 48:00 – The awareness cure: why sunlight heals shadows 50:00 – Practical ways to break the drama loop 52:00 – Jesse’s story: “Mr. Unsatisfied” and naming your personas 54:00 – Final exercise: ham up your persona to break its spellWhat You’ll Learn:This episode dives deep into the mental and emotional patterns that silently run the show for most founders—and shows you how to reclaim your power by becoming aware of them.Jesse Pujji and Dave Kashen unpack the concept of personas and the Drama Triangle (Victim, Villain, Hero), then go further with Internal Family Systems (IFS), exploring how parts of us form in childhood to keep us safe—and later, hold us back.You’ll learn:• What personas are and how they limit your leadership• How the Drama Triangle silently fuels resentment, chaos, and sabotage• The connection between fear, avoidance, and distorted decision-making• How to identify your own go-to personas and unconscious patterns• Practical tools to bring awareness, clarity, and freedom• The surprising power of “naming the part” (e.g., Mr. Unsatisfied)In this episode of Heart of Entrepreneurship, Jesse and Dave explore the hidden mental frameworks that drive how founders lead, react, and self-sabotage.From the Drama Triangle (victim, villain, hero) to IFS-inspired founder mindset coaching, they explain how our internal personas shape everything—from decision fatigue to leadership blind spots. If you’ve been looking for a framework to build more emotional intelligence, self-awareness, and behavioral flexibility, this episode is a masterclass.Whether you're working on releasing limiting beliefs, improving conflict resolution, or building a more conscious company culture, this episode gives you the tools to break free from reactive patterns and step into clarity and presence.Enjoyed the episode? Like, comment with the persona you’re working on, and subscribe for more real-talk on leadership, growth, and the emotional side of entrepreneurship.#foundermindset #leadershipgrowth #emotionalintelligence

This conversation tackles the emotional challenges faced by entrepreneurs, exploring how repressed feelings can hinder growth. It delves into the roots of emotional resistance, often stemming from childhood, and highlights the consequences of ignoring emotions like fear and sadness. The hosts discuss the physical manifestations of these feelings and stress the importance of embracing them for improved leadership. They advocate for practices that encourage emotional expression and the need to create supportive workplace cultures where emotions can be safely acknowledged.

This engaging discussion uncovers how embracing emotions can enhance leadership and decision-making in entrepreneurship. The hosts challenge the misconception that emotions hinder success, revealing them as vital sources of clarity. They explore the significance of emotional awareness, highlighting the impact of repressed feelings like fear and anger. Real-world coaching insights emphasize that true leadership involves acknowledging all emotions. Plus, they delve into the balance between personal boundaries in relationships and the entrepreneurial journey, urging listeners to harness their emotional intelligence.

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, and scale your company.✅ 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 / AGENDA00:00 – What is DFS (Desired Future State)?02:00 – How most people use “dirty fuel” (lack/fear) for motivation06:45 – Why judgment and self-criticism lead to yo-yo results10:00 – The power of accepting reality before setting goals14:00 – The “missed flight” analogy for emotional relief18:00 – Acceptance vs. resignation: what's the difference?22:30 – Above-the-line vs. below-the-line leadership25:00 – How to define YOUR DFS (not what’s “right”)29:00 – Why tuning into what you really want matters34:00 – The danger of compromising your vision prematurely36:00 – Rubber band theory: healthy vs. unrealistic tension39:00 – Specificity: Why your DFS must be detailed and vivid41:00 – Jesse visualizes his own DFS for Gateway X44:00 – How to apply DFS across teams, roles, and projects45:00 – Avoiding “fear fuel”: point positive, not negative47:00 – Coaching tool: ask “What’s your DFS?” when problems arise48:30 – JFK, the moon landing, and declaring bold futures51:00 – Final thoughts on vision, leadership, and inspiration🎯 What You’ll LearnThe psychological mechanics behind lasting motivationHow to shift from hustle/grind into creative flowWhy specificity, desire, and presence matter when leading a teamHow to apply DFS to your business, team, and personal goalsThe difference between dirty fuel (lack/fear) and clean fuel (creative tension)🚀 If you're navigating strategy, leadership, or scaling in a startup or bootstrapped business, this is a must-watch. Learn how to stay grounded in reality while still dreaming big—and help your team do the same.💬 Drop your DFS in the comments. What are YOU building?👍 Like, comment, and subscribe for more unfiltered conversations from real entrepreneurs.#Entrepreneurship #LeadershipDevelopment #StartupMindset

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-up00:00 – Jesse introduces the topic: spirituality for entrepreneurs01:00 – What does spirituality actually mean (and why should you care)?04:00 – You're not your thoughts: the voice in your head isn’t you06:00 – The meditation misconception: you don’t have to quiet your mind08:00 – Science vs. spirituality: where they’re already merging10:00 – What meditation really trains: non-reactivity13:00 – Why most inner voices are harsh critics—and how to shift them16:00 – Who am I if I’m not my mind or body?20:00 – The trap of chasing money, goals, and identity23:00 – Above-the-line vs. below-the-line living (for leaders)25:00 – Real-life example: Andrew pulls back during a tough meeting28:00 – The sacred pause: how meditation builds better relationships31:00 – How to treat thoughts like toddler tantrums or noisy strangers32:00 – Meditation and resilience: the founder’s secret weapon34:00 – How to meditate: Dave’s simple starter method36:00 – Best meditation apps and routines Jesse recommends38:00 – Mysticism vs. myth: experiencing truth directly, not through dogma41:00 – Unconditional love vs. conditional thinking44:00 – Why pressure isn’t the only path to success46:00 – Final reflections on choice, peace, and self-awarenessWhat You’ll Learn:This episode challenges how you think about yourself, your goals, and that nonstop inner dialogue most founders have. Andrew Warner, Jesse Pujji, and Dave Kashen explore the deep but practical benefits of meditation, spiritual awareness, and non-reactivity—without fluff or woo.You’ll learn:What it really means to be spiritual (hint: not religious)Why your inner voice isn’t you—and how to create space from itHow meditation improves decision-making, resilience, and leadershipWhy chasing money or goals might be masking deeper needsPractical ways to begin meditating (even if you hate sitting still)What “above-the-line” behavior looks like—and how to get there more oftenIn this episode of the Bootstrapped Giants podcast, we go beyond business strategy into founder mindset, self-awareness, and spiritual growth. Jesse Pujji and Dave Kashen join Andrew Warner to explore how meditation can unlock higher performance by reducing reactivity and increasing presence.This is not just “woo”—we get tactical about how to meditate, why it works even if you’re not spiritual, and how it directly impacts your entrepreneurial leadership, mental clarity, and relationships. If you're looking for more resilience, focus, or just a break from the pressure of building a company, this conversation will offer practical tools and deep insights.If this resonated with you, like the video, leave a comment about your own experience with meditation or mindset, and subscribe for more candid founder conversations.#mindsetmatters  #founderlife  #meditationforentrepreneurs

Discover the surprising truth about our resistance to love and joy. High achievers often downplay their wins, fearing vulnerability and deeper connections. Personal stories reveal how embracing appreciation can transform relationships and enhance success. A heartfelt leadership retreat uncovers the emotional depth of mutual recognition, while discussions highlight the struggles of accepting acknowledgment. Shifting from entitlement to gratitude opens the door to a more fulfilling life. This conversation will change how you engage with the world around you.

Uncover the surprising truth that creating your dream life and business may not be about working harder, but taking radical responsibility. Explore how limiting beliefs about struggle can lead to overwhelm and suffering. The conversation emphasizes the need to confront emotions and let go of resistance. Learn practical tools to shift your mindset and overcome mental blocks. By reframing responsibility, you can design a life and business you truly love, stepping into 2025 with clarity and purpose.

Discover how embracing emotions like fear, anger, and sadness can lead to better decision-making and authentic success. The speakers delve into the impact of emotional awareness on clarity and flow in entrepreneurship. They explore the cost of avoiding feelings and the importance of self-awareness in navigating personal journeys. Learn how processing emotions can help avoid impulsive reactions and lead to greater fulfillment. This insightful discussion reveals that confronting emotions is crucial for both personal and professional growth.