The Heart of Entrepreneurship

When people ask what they'd do if they only had a week to live, they're asking the wrong question. The question worth sitting with is: how would you show up? In this episode of Heart of Entrepreneurship, Dave Kashen and Jesse Pujji unpack what it would actually look and feel like to lead, listen, and connect the way founders would if time were visibly finite. The conversation moves from that thoug...

When founder and CEO Casey Kelly died suddenly in a car accident, Jesse Pujji was texting her the day before. She had no time to say goodbye. That kind of loss has a way of forcing the question that most of us spend our whole careers avoiding: how do you actually want to show up with the time you have? In this episode of Heart of Entrepreneurship, Dave Kashen and Jesse Pujji go somewhere most star...

Three equal co-founders, no titles yet, all best friends from high school. Jesse Pujji met a founder living that exact setup today, and the conversation they had surfaces one of the clearest frameworks for building a co-founder team that actually holds together. The principles that came out of it apply well beyond that one founder. In this episode of Heart of Entrepreneurship, Jesse and his co-hos...

The belief that money will make you feel safe, free, and worthy is one of the  quietest forces shaping how founders make decisions. In this episode of Heart of  Entrepreneurship, Dave Kashen and Jesse Pujji trace that belief to its roots and  follow it all the way through to what it actually costs. Jesse opens with a coaching session from 2019 where he uncovered an unconscious  core belief: more m...

In this episode, Dave Kashen and Jesse Pujji dig into why founders get paralyzed when facing major choices and why the real problem is never a lack of information. Dave explains that most leaders believe they're being rational when they're actually driven by emotions: seeking approval, avoiding fear, chasing safety, then rationalizing it all after the fact. The result is decisions that look logica...

Most founders walk out of a tough investor meeting and straight into the next one. That's exactly what keeps the emotional spiral going. In this episode, Dave Kashen and Jesse Pujji dig into why high-stakes founder moments – investor rejections, difficult employee situations, extended fundraising slogs – trigger threat responses, identity-level doubt, and discouragement even in experienced leaders...

What if accepting things as they are could make you more successful — not less? In this episode, Jesse Pujji and Dave Kashen explore one of the most misunderstood ideas in personal growth and entrepreneurship: acceptance. Most founders believe that if they stop pushing, they’ll lose their edge. But what if that constant resistance — the belief that “I’ll only be happy when…” — is actually the very...

Do you secretly believe success has to come with suffering? 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 t...

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. This sparks a raw, personal conversation about ego,...

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 anxi...

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 healthily, becomes one of the most powerful tools...

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 f...

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...

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...

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 boot...

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 y...

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 – Why founders avoid “weak” emotions like sadness...

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 founders need constant inner work 03:00 – Dave’s persp...

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? (And why we mistake it for our true self) 0...

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 feel unsafe (and how that started in childhood...

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 actually your greatest untapped superpower? In th...

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'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 spirituality actually mean (and why should you ca...

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 so uncomfortable, especially for high achievers, a...

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 limiting beliefs about struggle and success. They explore...