The Bootstrapper's Parable

Apr 17, 2025

Quit job. Dive headfirst. Start first company with impostor syndrome.
Anxious Me: "What if I can't do this?"
Zen Me: "We'll see."


6 months in. No PMF. Shut it down.
Anxious Me: "I failed. I was right. I am not built for this brutal bootstrapped world."
Zen Me: "We'll see."


Decide to start something new. New zing and new energy.
Anxious Me: "This time it has to work."
Zen Me: "We'll see."


Great co‑founder joins. Late‑night ideation sessions, sparks of mutual vision.
Anxious Me: "This is awesome to build with someone who gets it!"
Zen Me: "We'll see."


Together we send 400 cold emails. Zero replies.
Anxious Me: "This is going nowhere."
Zen Me: "We'll see."


First dream client signs up. We are making mooooney!
Anxious Me: "Finally! Success!"
Zen Me: "We'll see."


Trial clients demand free work, exploit our time, disrespect us.
Anxious Me: "I'm never going to explain this on my resume. I didn't expect the world to be this unfair."
Zen Me: "We'll see."


Long days debugging, doubt creeping in, Slack pings at midnight.
Anxious Me: "I'm burning out. This is not sustainable."
Zen Me: "We'll see."


Hit €15K MRR.
Anxious Me: "PMF? Is this it? Two of us made money from internet from a random corner of the world from scratch!"
Zen Me: "We'll see."


Some clients churn out of nowhere.
Anxious Me: "We're back to square one?"
Zen Me: "We'll see."


Clients appear from referrals of our past good work.
Hopeful Me: "Maybe you are built for this?"
Zen Me: "We'll see."


Adithyan