This is exactly why I've avoided raising so far. Not because VC money is bad - obviously it enables things that wouldn't otherwise be possible - but because I know myself well enough to recognise I'd react exactly like this.

The author nails it: "I started to actually operate in a way that is counterproductive for my startup, while thinking I was actually doing what was best." That's the dangerous part. The pressure doesn't announce itself as pressure. It masquerades as ambition, urgency, drive.

Bootstrapping has its own version of this though. Instead of investor expectations, you've got the slow burn of "am I wasting years of my life on something that needs capital to work?" The grass is always greener. At least with VC money, you can move fast and find out if you're wrong. With bootstrapping, you can spend 3 years proving out something that would have taken 6 months with proper funding.

Neither path is inherently better. But knowing which one will fuck with your head less is worth figuring out before you're in the middle of it.

If you can bootstrap, bootstrap. That's my advice.

You might be able to move faster with VC money, depends on your product. But getting that VC money can break you. And now you're on the hook and you've lost full control.

It's a hard call to name root causes.

If they hadn't taken the money, what would the counterfactual article have said?

Everybody creates narritives and belief-systems, where causes and effects seem so clear.

Perhaps I'm far too skeptical about their self-analysis. I've met very few people where their own analysis about themselves has matched what I have read in them. So many people misread their own minds and emotional drives. So I have learnt to cynically look for excuses and rationalisations and justifications.

The article is brilliant because we too rarely hear about people's doubts and negatives.

Some people (whether successful or not) do know themselves, but it is uncommon in my experience.

I helped bootstrap a business and we were in an incubator. There I saw some of the side-effects on businesses and founders from taking investment. We were just lucky that we couldn't be bothered with doing the distracting pony-show to get an investor onboard: we would have taken investment if it weren't so costly to do so.

Money and ownership causes weird pressures.

With boot strapping at least you can de risk with consulting/freelancing. And I think with the new generation of software development tools it’s much easier to validate the core business problems without grinding out code for weeks on end.