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.
Chapter Markers
00:00 ChatGPT Made Our $850M Startup Irrelevant 00:38 From SaaS to AI Agents 04:30 Growing Fast, But Also Dying 07:36 Why VCs Bet $200M+ on Observe 09:26 FOMO Made Me a Founder 13:30 We Had Users, But No Buyers 15:27 Why BPOs Were the Wrong Market 17:26 “I’ll Never Sell in India” 22:30 YC Made Me Think Bigger 27:22 From $1M to $50M ARR 30:13 Building AI Before ChatGPT 31:11 The Birth of Observe 2.0 32:18 When ChatGPT Changed Everything 33:15 When AI Agents Take Over 34:58 Rebuilding a $50M ARR Product 35:47 When Co-Founders Leave 38:50 Will AI Actually Kill Support Jobs? 43:51 “AI ARR Is Not Real” 45:45 Most Pre-AI Companies Are Bloated 47:34 Learning GTM by Doing It 51:24 Changing Product Is The Easy Part 58:29 Why Voice AI Is Just the Beginning 01:01:25 The Founder Playbook 01:04:10 What Makes a Great Product? 01:05:37 “I’m Here to Win”
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Connect with Siddhartha on: LinkedIn: / siddharthaahluwalia Twitter: https://x.com/siddharthaa7 ------------- This video is for informational purposes only. The views expressed are those of the individuals quoted and do not constitute professional advice.
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