If you’ve ever tried to plan a group trip and watched it fall apart in the group chat… this one’s for you.

In this episode, I sit down with Jay Raval, co-founder of Troopa — an AI-powered travel planning platform built around one simple truth: someone always ends up doing all the work.

Jay walked away from a stable consulting career to build a startup that’s part AI, part collaboration tool, and very human. We talk about what it’s actually like to make that leap — the self-doubt, the imposter syndrome, the messy middle, and the mistakes you only see once you’re in it.

We cover:

• Why quitting consulting “sounded like a stupid decision”
• The reality of building an AI product (and how expensive APIs get… fast)
• Why “build it and they’ll come” is a lie
• Underestimating marketing and distribution from day one
• Being told by a VC not to raise money
• Building in public without becoming a self-help guru
• And why travel planning is emotional, not just logistical

This is a candid, grounded conversation about startups, risk, and learning as you go, not just the highlight reel.

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