Podcast Episodes

Lonely at the Top: Why Success Can Still Feel Empty

Episode 21

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 refle…

Published on 10 hours ago

What Happens When You Move Beyond the Ego

Episode 20

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 unco…

Published on 2 weeks ago

Anger Is a Compass: How Founders Turn Emotion into Clarity

Episode 19

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…

Published on 2 weeks, 2 days ago

Why Following Aliveness Might Be the Smartest Business Move

Episode 18

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 practi…

Published on 3 weeks, 6 days ago

When You Don’t Know What’s Next – You’re Expanding and Growing

Episode 17

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 …

Published on 4 weeks, 1 day ago

Why Even Billionaires Still Don’t Feel Safe

Episode 16

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 cha…

Published on 1 month ago

Beyond Success: Gagan Biyani’s Inner Journey Building Udemy, Sprig, and Maven

Episode 15

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 Mav…

Published on 1 month, 2 weeks ago

How to Change Without Willpower, Guilt, or Discipline

Episode 14

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 …

Published on 1 month, 3 weeks ago

The Parts You Reject Are Blocking Your Potential

Episode 13

Why You Resist Feeling Bad (And How It Holds You Back as a Founder)

✅ Are you bootstrapping? You need this:
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✅ Master the Inner Game of Entrepreneurship here:
http…

Published on 1 month, 4 weeks ago

How Enjoyment (Not Hustle) Drives Real Growth

Episode 12

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:…

Published on 2 months, 1 week ago