The Heart of Entrepreneurship
Entrepreneurship is about more than your income statement.
10
Hard Conversations That Make Your Team Better
<p>Telling someone a hard truth only helps if they can actually hear it. In this second half of a two-part conversation on feedback, Dave Kashen and Jesse Pujji move from caring personally to challenging directly, and dig into how to say hard things in a way that lands.</p><p><br></p><p>Dave opens with a framework he calls speaking inarguably, drawn from the Conscious Leadership Group, Nonviolent Communication, and Stanford's "Touchy Feely" class. The biggest trap in giving feedback is stating your stories about someone as if they were facts, and Dave shares a split-brain study showing...
Why Holding Back Is Hurting Your Team
<p>Every leader eventually has to tell someone a hard truth, and how it lands depends on the relationship built around it. In this episode of Heart of Entrepreneurship, Dave Kashen and Jesse Pujji explore why candor and care work best together, and what happens to a team when fear pulls them apart.</p><p><br></p><p>Jesse opens with his own journey with feedback: growing up in a direct household, giving feedback constantly at McKinsey, and becoming a CEO whose directness left people intimidated, until holding his tongue didn't work either. Dave grew up with very little conflict...
Your Need to Be Right Is Slowing Your Startup Down
<p>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.</p><p><br>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...
Founders Who Say Yes to Everything End Up With Nothing
<p>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.</p><p>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...
Why a Perfectly Designed Company Culture Still Fails
<p><br>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.</p><p>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...
The Real Reason No One Follows Your Company Values
<p>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.</p><p><br></p><p>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.</p><p><br></p><p>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 it...
Co-Founder Relationships That Can Navigate Anything
<p>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.</p><p>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...
Why Spirituality Is a Founder's Edge, Not a Distraction
<p>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.</p><p><br>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...
Why the Smartest Founders Stopped Trusting Their Brain
<p>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.</p><p>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...
How Founders Trick Themselves Into Never Having Enough Time
<p><br>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?</p><p><br>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...
