The Heart of Entrepreneurship

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.

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⏱️ Episode Outline
[00:00:00] Intro – Dave opens with gratitude and sets up Gagan’s journey
[00:01:57] Gagan’s early story: middle-class upbringing, parents’ split, first business at 13
[00:04:12] Lessons from speech & debate and bootstrapping a youth camp
[00:05:24] Frustration with education system and early path to entrepreneurship
[00:07:03] Founding Udemy – excitement, clashes, and a painful co-founder exit
[00:09:00] The reality of co-founder departures and why they’re more common than people admit
[00:12:00] Founder guilt and the challenge of letting go of employees
[00:16:03] Why firing faster often strengthens culture and execution
[00:19:03] Baseball as a metaphor for hiring “batting averages”
[00:23:06] Pain-driven motivation, control, and lessons from Sprig’s collapse
[00:29:33] Building and losing control: Sprig as an early “ghost kitchen”
[00:36:45] Macro risk, timing, and luck in startups vs. smaller businesses
[00:44:06] Comparison traps—Bezos, Chesky, and the illusion of “proving it”
[00:49:30] Shifting the burden of proof and redefining success after failure
[00:52:51] Relief after shutting down Sprig and finding freedom
[00:56:06] Travel, self-discovery, and learning to separate identity from achievement
[01:05:06] Learning to love yourself without external labels
[01:08:06] Resisting joy and gratitude as much as pain
[01:11:06] Why inner work matters for founders—and how it changes execution and team retention
[01:15:00] Closing reflections on investing in personal growth

💡 What You’ll Learn
  • Why co-founder departures are far more common than founders admit
  • How to reframe letting go of employees as an act of alignment, not failure
  • The trap of pain-driven motivation and how to shift beyond it
  • Why timing, luck, and macro forces matter more than pure talent
  • How self-discovery and inner work fuel long-term entrepreneurial success

📌 About This Episode

This is not just another “startup success” story—it’s a raw, honest look at the heart of entrepreneurship. Gagan and Dave dig into the messy human side of building companies: the guilt of firing, the relief of shutting down, the burden of comparison, and the deep work needed to move from proving yourself to living authentically.

If you’re a founder, this conversation blends practical insights on leadership and hiring with emotional wisdom about resilience, identity, and growth. Think of it as both startup strategy and personal development 101.

🙌 Stay Connected
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What is The Heart of Entrepreneurship?

Entrepreneurship is about more than your income statement.