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 bootstrapping? You need this:
https://bootstrappedgiants.com/subscribe

✅ Master the Inner Game of Entrepreneurship here:
https://www.davekashen.com/newsletter-sign-up

⏱️ 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
If this episode resonated, let us know in the comments. Don’t forget to like, subscribe, and share with a fellow entrepreneur who needs to hear this.
#HeartOfEntrepreneurship #StartupLessons #FounderJourney

Keep Codes & Laws Free w/ Scott Reynolds of Upcodes

Mass Construction Show

What the Pro Codes Act Would Change

The AI-powered Podcast Player