Because We Were Winning The Wrong Game | Swapnil Jain Observe AI
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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This video is for informational purposes only. The views expressed are those of the individuals quoted and do not constitute professional advice. Receive SMS online on sms24.me
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