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The Heart of Entrepreneurship: Daily Summaries Delivered
by Dave Kashen and Jesse Pujji
Entrepreneurship is about more than your income statement.
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- 6 days ago42 min
Your Need to Be Right Is Slowing Your Startup Down
Jesse Pujji met a CEO one week after he bought a billion-dollar public company, the biggest deal of his career. The first thing the CEO said was "I don't know what I'm doing." Jesse assumed it was false modesty. It turned out to be one of the most useful habits he has picked up from senior leaders, and this episode is about why.In this episode of Heart of Entrepreneurship, Dave Kashen and Jesse Pujji dig into the founder's need to be right: where it comes from, why it creates suffering, and how it quietly slows down learning. Dave traces it to conditional self-worth and the brain's discomfort with uncertainty, then lays out the mechanism. Uncertainty produces fear, fear sends founders into their heads to find the right answer, and the search for certainty ends up blocking the very clarity they were after. They open with a reaction to Travis Kalanick's claim that entrepreneurs have to be willing to suffer more than everyone else.
- 1 weeks ago36 min
Founders Who Say Yes to Everything End Up With Nothing
Most founders say yes to hires they're unsure about, clients that aren't the right fit, investors they don't want as partners, and meetings they have no time for. Then they wonder why their calendar is a disaster and they can't do quality work.In this episode of Heart of Entrepreneurship, Dave Kashen and Jesse Pujji dig into why founders default to yes, and what it costs them. Dave lays out the whole body yes: checking head, heart, and gut before committing, and treating a no from any one of them as a veto. Then he introduces the practice most people will push back on: saying no to everything first, and paying attention to whether what shows up is anger or relief.Jesse shares the studio company he agreed to run as CEO without a whole body yes, and how that turned into eight months of doing work he didn't want. Dave runs a live coaching walkthrough for a founder on the fence about a COO hire, from acknowledging the fear of getting it wrong to bringing the decision down into the heart and gut.
- Aug 14, 202647 min
Why a Perfectly Designed Company Culture Still Fails
Founders spend months defining values and building culture rituals, then assume the work is done. But values get set when you're calm, and tested when you're scared. This episode picks up last week's cliffhanger: even a perfectly designed culture collapses if the founder can't recognize when they've dropped into a reactive state.Dave and Jesse cover above the line vs. below the line, the body and language cues that reveal which state you're in, the question that exposes where you're resisting reality ("Is there anything I'm wishing was already different than it is?"), and the four steps to shift from threat back to presence. Plus: the negotiation where Jesse saying "I feel queasy in my stomach" got the other side to change their terms on the spot.It ends on the line Jesse tells every founder he works with: "You will always be the ceiling of your company."
- Aug 7, 202650 min
The Real Reason No One Follows Your Company Values
Most founders build culture by copying it. Amazon's principles, Facebook's values, whatever sounds good on a wall. Then their team senses the inauthenticity, quietly ignores the values, and the founder wonders what went wrong.In this episode, Dave and Jesse get practical about building culture from the inside out — starting the week Jesse makes his first hire for Gateway X's new chapter.Dave shares the case study of Fetch Rewards, a multi-billion dollar company whose CEO shifted from fear-based motivation ("if we don't do this, bad things happen") to its exact converse, and watched creative output dramatically increase. Jesse tells the inside story of Ampush's culture turnaround, including the employee who said: "You don't say anything different, but I feel different when I walk out of it."Then they run a live coaching session: taking one of Jesse's real values (bias to action + rapid learning) and working it backwards into an actual interview question and a behavior-based survey item — the two places culture stops being words and starts being real.
- Jul 29, 202648 min
Co-Founder Relationships That Can Navigate Anything
Most founders choose a co-founder off a spreadsheet. The skills check out, the background raises money, and the person feels "right on paper." Then they skip the titles, skip the decision rules, and default to harmony, assuming the relationship will sort itself out. It rarely does.In this episode of Heart of Entrepreneurship, Dave Kashen and Jesse Pujji break down the full arc of the co-founder relationship: how to evaluate a potential co-founder before committing, the questions to ask during co-founder dating, why "co-founder" is not a role, and the maintenance practices that keep the relationship healthy years in.Jesse shares how Ampush ran a shared founders email address for three years with no clear decision authority, until, as he puts it, "people called it a three headed monster." He also walks through the team learning exercise he took from McKinsey that gets new teams aligned in a single session, and the moment his COO answered "what are you most afraid to tell me?" with a fear of being steamrolled, which he says shifted their entire working relationship from day one. Dave explains why, in his words, "most drama is created by a lack of clear agreements." The two then work through a hypothetical 60/40 equity conversation, and Dave shows how it can quietly become a fight about worthiness instead of fairness.
- Jul 29, 202650 min
Why Spirituality Is a Founder's Edge, Not a Distraction
Can you explore spirituality and still build a scaling, successful company? In this episode, Dave Kashen and Jesse Pujji take on the fear that drive and awakening pull in opposite directions, and make the case that they reinforce each other.They start concrete with what founders can and can't control (sorting the files, why you can't control the outcome but can control whether you believe your thoughts), then move into the deeper work: letting go of resisting reality, the unfindability of the self, and what it means to lead from awareness instead of a self that always needs defending. The throughline is that none of this runs on belief. It runs on direct experience, and the less defended you are, the easier it becomes to create what you want.Along the way: the train of thoughts, awareness as the sky, the hard problem of consciousness, moths flying into streetlights, and the movie of your life where you're also the screenwriter.
- Jul 15, 202654 min
Why the Smartest Founders Stopped Trusting Their Brain
Jesse Pujji's wife met a CTO candidate at a happy hour and came away with a weird feeling she couldn't put into words. The guy had interviewed perfectly and accepted the offer, then reneged by email on the morning he was supposed to start. This episode is about the kind of intelligence Jesse spent most of his life overriding.Dave Kashen has coached Jesse for almost ten years, and the premise of this show is that success does not require suffering. In this first episode, the two of them dig into why founders over-rely on the intellect even though the brain is a survival organ that overweights threat and often gets its predictions wrong. Dave lays out a simple map of three intelligences: the head that thinks, the heart that holds emotion and desire, and the gut that knows instantly. The conversation works through how to tell them apart, how to start trusting them, and what changes when you stop running every decision through your head.
- Jul 7, 202646 min
How Founders Trick Themselves Into Never Having Enough Time
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 thought experiment into something more practical and more urgent: why the clarity death creates is available right now, and what gets in the way of accessing it every other day.At the center of the episode is a distinction Dave draws between finite and scarce. Finite is a fact. Scarce is a story. And the story of not enough — not enough time, not enough confidence, not enough freedom — is one most founders are running on without realizing it. When that story loosens, something shifts. Founders tend to find the presence, the appreciation, and the boldness that the thought experiment was trying to point them toward in the first place.
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