From IT Staffing to AI Builder: One CEO's System for Finding Opportunities and Failing Fast | Eshwar Prasad | Part 1

This episode is about what a founder actually does when he decides the next opportunity requires starting over.In Part 1 of this conversation, Eshwar - CEO of a global IT staffing company - breaks down why he handed day-to-day operations to his team and went all-in on building AI products alone, 16 hours a day, with no traditional development background.This wasn't a strategy retreat. It was a constraint-driven decision.We cover: Why Eshwar stopped running the business he built to go build something newHow AI collapsed his test-and-fail timeline from six months to a weekWhat "vibe coding" looks like for a non-programmer operating at full intensity The childhood scarcity that built his tolerance for uncertaintyThe partnership that scaled fast and fractured - and what he took from it Why he doesn't use the word "risk" - and what he calls it insteadIf you're a founder operating between what's working and what's next, this conversation will feel familiar.This isn't a highlight reel. It's a real look at how a seasoned operator makes the decision to go back to zero - and what it actually takes to function there.Reach out: [email protected] Milestones is a video podcast featuring honest conversations with founders, parents, and investors about building real businesses, staying healthy, and raising families.New episodes release Tuesdays and Fridays.Youtube: https://www.youtube.com/@ChiefMilestonesInstagram: https://www.instagram.com/chiefmilestones/Spotify: https://open.spotify.com/show/7HLDAe7SP3GnJSTOgAQqLy?si=6e9ac82be46f413cApple Podcasts: https://podcasts.apple.com/us/podcast/chief-milestones/id1861185226