Why Subscribe?
I'm Ajay Yadav, and I've scaled 2 startups to over 20 million combined users. My first company started in a college dorm room, a platform helping people find roommates in New York that reached 3+ million users and $17M+ raised. But it also taught me expensive lessons about growth-at-all-costs culture and why 90% of funded startups still fail.
Then I co-founded Simplified AI, one of the first 50 AI companies globally, using OpenAI's APIs back in 2020-2021 when most founders had never heard of GPT. We scaled that AI-powered platform to 20+ million users and raised from top VCs including Craft Ventures and Khosla Ventures.
Now I'm doing it differently with Otto AI:
Building AI back office for creative small businesses and solopreneurs. This time, I'm bootstrapping first, then seed-strapping, proving you can build incredible AI products with small teams and smart capital.
What you'll get every week:
Real-time insights from building Otto AI with a lean team and limited runway
Hard-won lessons from scaling two companies to 23M+ users (one pre-AI, one AI-native)
Frameworks for SMB SaaS that actually work (not enterprise playbooks that don't scale down)
Why SMB startups are finally getting funded after years of VC neglect, and what changed in the AI era
How indie developers are now building million-dollar businesses with 1-2 person teams and competing with venture-backed companies
Behind-the-scenes from my podcast conversations with VC’s about this massive shift in startup funding and what it means for solo founders
Exclusive access for paid subscribers:
Monthly deep-dive lessons and learnings from Otto AI's growth with detailed metrics, failures, and pivots you won't see anywhere else
Private community of founders building in the AI + SMB space
Exclusive VC interviews about why they're now writing checks to solo founders and SMB-focused startups
I publish every Tuesday (tactical AI startup insights) and Friday (real stories from building in public).
Join founders who are building the next wave of AI companies, profitably, sustainably, and without needing massive VC rounds to get started.
