My friend and I started it as a side job, working nights and weekends. We also downsized and cut all our expenses to about $1,000/month (mortgages were smaller back in 2005).
We quit our full-time jobs when 1Password revenues were close to $80,000/year.
You mean 1password.com?! That's amazing great work. Huge Canadian success story [1]. You're definitely underselling the achievement here but guess it's funny to look back and were probably super excited about that first 80k. I imagine there is probably a books worth of war stories about this.
This is a good point - reading up on FIRE https://en.wikipedia.org/wiki/FIRE_movement can be useful - perhaps with some intelligent allocation of resources and time you can start bootstrapping today and five years later have the mortgage payment eliminated.
And if you're serious about doing a startup, do consider moving to an area that will have what you need but is cheaper.
I'm working on downsizing and reducing expenses. I'll have repaid a credit fully next year, that allows me to increase savings etc. Slowly those things come together.
Also trying to create small side hustles, bootstrap them, hope that something sticks and try to scale that up till I can quit the corporate job and focus on things I'd love to do.
It's probably a longer journey than expected if you've got no money advantage.
We quit our full-time jobs when 1Password revenues were close to $80,000/year.