are you kidding me? This guy is the definition of bootstrapped. How do you think he got that $55K? He was bootstrapping design courses - I've been following this guy for a few years.
In fact (don't know full facts, but I too have been reading his blog for some time), I think he was a designer (of mobile apps and web sites, maybe had dev skills too), then wrote a few books for a while (on areas where he had skills, like design, later on other areas too), then used the earnings from that to start Convertkit. IIRC he even mentions this approach in one of his blog posts. Bootstrapping all the way, seems like, to me :)
I am absolutely not claiming he didn't work very hard to start his company or earning his money.
I am neither claiming he's bad or wrong or anything like that. Like jacquesm said it's probably more of a problem of definition between a dominant one and mine (in other words, looks like I am wrong). I have seen people starting companies with nothing, not even a roof on their heads. I started a company with the amazing comfort of 50k€. I am working hard to make my company a success, but I command the efforts of the guys I have seen eating noodles for years before their company finally took off.
We are talking living way below the poverty line here, which is not what I lived when I started a company with 50k€
Given how easy it is these days for a developer to make €50k (e.g. by contracting on a day rate fee for a company), there really is no need to eat noodles for years. You do work for 6 months, save up €50k, and live frugally (but not crazy frugal) for a while.
Let's say 500€ daily rate (which is probably average in France with a very large standard deviation between Paris and deserted zones and factoring varying daily rates which are domain specific and experience related. No way a junior RoR freelance would make 500€ in Massif Central for instance. Likewise, 500 is low for an experienced data science freelance working in banking in Paris). 206500=60k€ gross
After social contributions, 30k€ net revenue in France (actually a little more but I take the liberty to round that down).
In large cities, 33% of revenue for housing is not uncommon.
We're left with 20k€, of which we have to substract revenue taxes (rule of thumb in that revenue range, about 1 month revenue per year) so here 5k€.
15k€ for 6 months. living frugally you can probably save 2/3 so you can save 10k€ in 6 months.
Assuming these ratio, it would take 2.5 years of steady, near fulltime employment as a contractor to save these 50k and go all out on your project.
"keep it in a company" at least in France won't really help you, as social contributions are collected every 3 months.
They are very good at hounding you to pay (and inversely keen on giving you back any overpaid amount ;-) ) so the incorporation does not really help here. You still owe them about half the gross revenue.
