Why Group Trips Never Happen and How Jay Raval Is Trying to Fix It

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 lieUnderestimating marketing and distribution from day oneBeing told by a VC not to raise moneyBuilding in public without becoming a self-help guruAnd why travel planning is emotional, not just logisticalThis is a candid, grounded conversation about startups, risk, and learning as you go, not just the highlight reel.Follow us on all platforms!Instagram ~ @fayltalesTiktok ~ @fayltales LinkedIn ~ @fayltales