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In this episode of Startup Strategies, Juliana sits down with Gaurav Bhattacharya, three-time venture-backed founder and CEO of Jeeva AI, who proves that scrappy execution beats massive funding every time. After getting tired of complex enterprise sales cycles in his previous companies, Gaurav built an AI sales prospecting tool using tactics that sound insane until you see the results: sending two cents through PayPal, getting banned from communities on purpose, and treating legal threats as rebranding opportunities. From aerospace engineer to Forbes 30 under 30, Gaurav shares how a 9-person team generated $5 million ARR competing against Andreessen Horowitz-backed companies spending millions on billboards.
He reveals the psychology behind why "because" is a magic word that bypasses rational thinking, how getting rejected from Slack groups became market validation, and why Disney's lawyers inadvertently helped him build a better company. Gaurav breaks down the exact strategies behind booking 107 meetings in one week, from weaponizing PayPal's notification system to turning freemium users into intelligence assets that led to six-figure enterprise deals.
This conversation challenges everything you think you know about outbound sales, competitive advantages, and building with constraints instead of capital.
Gaurav shares:
Let's break down his Startup Strategies!
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