Starting Sherlocks was probably the worst financial decision I ever made.
Or so it seemed at the time.
When I decided to start my third company, I had genuinely lucrative options on the table.
Good money, interesting work, and none of the uncertainty that comes with building from scratch.
I chose to start anyway.
Those options were very good, although after doing this three times, I've come to understand something about myself.
I default to being a large part of a small system, not a small part of a large one.
After Doubtnut was acquired, I found myself inside a bigger company that was comfortable, stable, well-resourced, and completely wrong for how I'm wired.
The entrepreneurial default is hard to switch off.
You take ownership, you want to move fast, you want the problem you're solving to actually matter to you. Being one function inside a large machine doesn't scratch that itch, no matter how good the compensation is.
So I left and started Sherlocks, accepting the financial stress of not knowing how long the runway is or when the next funding round closes.
I knew the problem I wanted to solve.
I knew AI was ready to do something real in reliability.
That was enough to make the "stupidity" feel worth it.
Has there been a moment when you chose the harder path, knowing it made no financial sense?