I believe the answer to this question is different depending on what stage we were at:
Why bootstrap when Scribbl was just an idea?
This one is easy. I'm an engineer, so the question really became:
Which is more effort?
I happily started building.
Why continue bootstrapping after a POC was built?
When we started https://Scribbl.co, we hadn't ruled out raising funding at some point. We knew getting a POC built would be necessary regardless of the path we took.
After the POC was built I do believe we could've successfully raised funding.
So why didn't we? Like most other decisions, our answer came from weighing many tradeoffs.
Bootstrapping seemed more certain. I can build a product that 1,000 people will love, but can I build something that will dominate a market? Committing to VCs would make a promise I didn't know I could keep.
The end result of bootstrapping provided the lifestyle I wanted. I'm not interested in growing an organization. I'm interested in building a business that can support me and give me freedom to create.
We weren't so sure where we were going yet. Funding would accelerate us immediately. This felt like flooring a gas pedal with a blindfold on.
Acceleration can create mysterious certainty. You sink or you swim.
Why bootstrap once we had paying customers?
For some, I could see a real case for taking some funding once a product was validated with paying users.
For us, we were in a bit of a pickle. We built this thing that had some general value that we were able to sell.
We originally thought: Okay, let's start cranking on the engine. Simple. Drive people to our landing page -> get sign ups -> convert paid users.
Had our engine worked like that, we probably should throw some money into it.
Unsurprisingly, it didn't. We were left with a somewhat valuable product, with no gravitational market pull to carry us to success.
Capital wasn't going to solve this problem.
If you read this far, I hope this helped!
My goal is to be as transparent as I can be while detailing my journey with https://Scribbl.co.
I love all and any feedback you may have.
Thanks for reading.