The Building Startups
I’m Ajay Yadav. I build things because, honestly, it’s the only survival skill I had that actually worked.
I failed high school twice. Moved to the U.S. at 17 with broken English and a suitcase full of things I didn’t need. I didn’t know anyone. I didn’t understand how anything worked. So I taught myself engineering (dropped out, so calibrate expectations), design, product, and eventually growth. Growth is the thing that turned two ideas built in small apartments into platforms used by millions.
Over the last decade, I accidentally built two companies used by more than 20 million people. A roommate app I started in a college dorm. And later, Simplified, one of the earliest AI platforms built on OpenAI’s APIs, back before “AI founder” became a personality trait.
I learned a lot. Mostly the expensive way.
Now I’m building my third company: Otto AI, a back office for creative entrepreneurs.
Because the world has shifted. We used to be inspired by a handful of people on TV. Today anyone with a phone and an idea can change how we think, buy, learn, vote, dream, or build. But behind every creator is a mess of invoices, expenses, taxes, and admin work no one ever taught them to manage.
And that mess costs money.
Creators leave thousands on the table every year. Untracked write offs. Overdue invoices. Late fees. Undercharging. Inconsistent pricing. Hours lost to admin tasks that drain the energy they need for their actual work. They should be creating. Not doing math at midnight.
So we’re building Otto to help creative entrepreneurs make more, keep more, and waste less time doing things they never wanted to do in the first place.
I’m building it publicly, quietly, stubbornly. Small team, small budget, big belief. The long game only.
This Substack is where I write the real version of that process. Not the investor update and not the LinkedIn highlight reel. The in between parts. The honest parts. The days where you’re sure you’re onto something and the days where you wonder what you’re doing at all.
Somewhere along the way, I also picked up coding again after fifteen years. People call it vibe coding now, so I just went with it. Building things in public with equal parts improvisation and chaos. If you’re into that, I write about it here too: The Vibe Founder.
Why subscribe?
Because I’m not here to preach frameworks.
I’m here to show you what it actually feels like to build a company in 2025, as an immigrant, as someone who taught himself everything the world didn’t hand him, as a founder who has failed, rebuilt, pivoted, and still wakes up wanting to build things that matter.
Every week you’ll get:
Scenes from building Otto AI
Lessons from scaling two companies
A builder philosophy shaped by trial, error, and refusing to quit
Stories for creative entrepreneurs, indie builders, and immigrant founders
The internal stuff, the quiet, unpolished version of building
For paid subscribers
Monthly deep dives with real numbers, pivots, mistakes, and what we’re actually learning while building Otto AI with a tiny team and stubborn optimism.
Plus a private space for founders building unconventional companies without waiting for permission.
Publishing cadence
Tuesdays → Tactical notes on Otto AI
Fridays → Story driven essays
If you’re building something, or trying to rebuild yourself while building your thing, you’ll fit right in here.
Welcome to The Building Startups.
The story is already moving.
