A Fundraising Survival Guide

As a fan and practitioner of bootstrapping I was interested in the part where pg says that the delay caused by bootstrapping can be fatal to many kinds of startups. Flipping that around, are there kinds of startups where the delay is not fatal?

Taking Basecamp as an example, it was released probably decades after the first project management software. Is bootstrapping best if you're going after a mature class of software?

I think that might be the case. When I'd started I was looking at a completely new class of software that didn't seem to have any entrants. Then Ning repositioned with heavy backing and there was no way I could see to compete. So we went into a vertical as a new approach to an existing and mature field. That's when all the bootstrapping pieces came into place. Six months of side jobs built a product that we could build services around which lead to twelve months of ramen-profitability. Now we're in post-ramen-profitability and growing. It's definitely slower and that's let competitors enter with similar approaches but none that could own an entire market the way Ning could.

On the flip side, if we were venture backed we still might not have been able to compete and this story might be about how we'd wasted several million dollars.

on an average how long do YC companies take to raise the next round (could be series A, or another larger angel round) of funding after the YC funding?

Money quote: Startups live or die on morale.

I think pg nails it when he says that talking to tons of investors takes up lots of time, and given the extremely low probability of a deal going through it comes out as extremely hard.

One of the reasons that exacerbate this problem is the presence of 'wannabe' angels in the investing community. These will typically be folks who worked long and hard in a big company or possibly got rich as an early employee and now fantasize about doing angel investments. Obviously the ambiguity of the whole process is too much for them to ever go through an investment.

IMHO the fund raising process is all about waisting as less time on the folks who will not invest and figuring out the potential investors.

Possibly pg should elaborate more about how founders can predict the 'successful' investors and skip the bad ones.

"If you factor out the "bootstrapped" companies that were actually funded by their founders through savings or a day job, the remainder either (a) got really lucky, which is hard to do on demand, or (b) began life as consulting companies and gradually transformed themselves into product companies."

I had to read the paragraph a few times, so I may be misunderstanding it, but why do we factor out bootstrapping through savings or a day job? Is that not 'real' bootstrapping?