390 / August 17, 2026
ChatGPT Killed My $50M ARR Business Overnight | Swapnil Jain Observe Al
Observe AI raised $125M from SoftBank at an $850M valuation, went on to cross $50M ARR, and worked with some of the world’s largest enterprises. But after 10 months everything changed.
From a growth stage startup, Observe became an early stage startup, not because they did anything wrong, but because world changed forever very fast.
In this episode, Swapnil, Founder & CEO of Observe AI candidly shares what it takes to rebuild a company after you have already built it, why changing people and culture are harder than changing the product, why today’s AI winners could disappear as the technology stack changes, and why he thinks we are still in the first innings of AI.
This conversation is as much about AI as it is about a founder’s drive to win.
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