[yevpats]

Firstly, Big Kudos if you were able to bootstrap a big business this is very very hard (actually doing this with VC money is also hard). As someone who did both VC funded startup and self-funded (fuzzit.dev acquired by GitLab), I would say doing a self-funded startup even though it sounds good (because you are an underdog and you win on the hardest level if you succeed), a lot of time is really impossible or if possible there is information people are not sharing - for example for self-funded - did you include 300k-600k you had as saving that you used while working on it (or did you consulting while working on it). Did you take loans to grow faster? - the details are really important.

Personally I got to a conclusion that the common ground is a lot of time what makes sense. If you can validate as much as possible before raising the first round, raising reasonable amount of what you need to prove or get to the next milestone and do a lot of first principal thinking that could be better then beiing on each side of the extreme - let's raise as much as possible or Im not taking any VC money because it is all bad. Just my 2 cents but yes if you can grow a business with your own money - then it's amazing - just think this is not possible in a lot of cases and products.

[x0x0]

I've done the same (funded and bootstrapped), and most of the conversation about this choice is just stupid.

Engineers cost easily $200k. If you need much functionality before you earn significant money, you simply can't bootstrap. If you don't have founders that can afford to earn very little money for probably 2+ years, you can't bootstrap. Even an inexpensive 4 person eng team, one cs, and some basic office space and marketing/ad spend and all the other stuff a functioning company requires costs a million dollars a year.

Or you need significant ad spend (b2c), or you have midmarket or enterprise buyers who -- quite reasonably -- refuse to buy from a small company unless you can use millions in investment to prove that you aren't going to up and disappear after they spend serious internal effort to implement.

Or -- and this one is particularly painful -- one of your competitors raises, and can suddenly hire many more eng and salespeople, or significantly outspend on ads. That is very difficult to compete with.

These realities foreclose most opportunities to bootstrapping.

[kepano]

You raise good points, and it echoes advice I have given many times — follow the funding path that makes sense for you and your business.

That being said, I do think times are changing. I don't think Obsidian could have been bootstrapped as easily 5 to 10 years ago. The leverage we get from cross-platform frameworks, scalable server architecture, etc, make it possible to stay small. LLMs will even further enhance that leverage for entrepreneurs.