Episode 71: Million-Dollar Stock to Backing Indian Startups | Sandeep Murthy

In Episode 71 of #DamaniTalks, Anirudh A. Damani is in conversation with Sandeep Murthy, Founding Partner at Lightbox, and one of the earliest champions of long-term, product-first startups in India.From his formative years under Barry Diller to funding Cleartrip and shaping India’s consumer internet story, Sandeep reflects on 25 years of backing bold ideas before they were cool - and staying the course when others walked away.But this is more than just a career recap. It’s a candid, no-frills masterclass on what it really takes to build durable businesses and why the current VC playbook needs a rethink.Expect raw truths about broken feedback loops in venture, distorted cap tables, the obsession with IRR over DPI, and why burn is not a business model.Whether you are a founder navigating PMF, an LP questioning returns, or a VC looking for perspective, this episode is packed with grounded insights, real stories, and hard-won wisdom.Highlights:The inside story of TripAdvisor’s early daysThe $10M deal where Sony took 92% equity - and the hard lessons it leftBetting on Indian travel before it was a thingHow VC signals are failing the founders they fundWhy “valuation is vanity, exit is reality” still holds trueWhat real founder support looks likeTune in for a deep dive into what it truly means to be a founder-first investor and why Sandeep Murthy is still betting on real businesses over flashy pitch decks.Chapters:08:46 – Dotcom days: Match, Expedia & TripAdvisor20:15 – The 92% equity story: A deal that changed everything30:49 – From IAC to India: The Cleartrip chapter44:08 – Betting on Indian consumption50:20 – How to balance ambition and burnout? 1:00:24 – How to invest strategically in emerging markets?  1:10:26 – How to build founder-investor relationships? 1:20:29 – Why do most new venture funds struggle? 1:30:31 – How to choose the right team and investors? 1:40:34 – Measured growth and founder evolution 1:50:38 – Local adaptation in the Indian market 2:00:41 – How to embrace change & redefine failure? 2:10:45 – What is the role of perspective in business?  2:20:48 – The joy of building & the meaning of lightbox 2:23:45 – Rapid Fire: legacy, balance, bold betsMore about our Guest, Sandeep MurthyLinkedin: https://www.linkedin.com/in/murthysandeep?utm_source=share&utm_campaign=share_via&utm_content=profile&utm_medium=ios_appTwitter: https://x.com/sandeepm1?s=21Instagram: https://www.instagram.com/sandeepm1?igsh=a3RrM2dyaHcwMHR6Learn more about your host, Anirudh A. DamaniWebsite: https://www.showmedamani.com Instagram: https://www.instagram.com/showmedamani/ LinkedIn: https://www.linkedin.com/in/showmedamani/ X: https://x.com/showmedamani WhatsApp Channel: https://whatsapp.com/channel/0029ValxvDNChq6Rd5AbUQ3H YouTube: https://www.youtube.com/@showmedamani

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