It has been a little over a year since I announced the news that my marketing software startup closed it’s Series
B round of funding.  The article, “Insanity?
Why A Bootstrap Entrepreneur Raised $17 Million in Venture Funding”, was a
candid glimpse into the rationale for raising what seemed like a huge amount of
money to me at the time (it seemed huge, because it was — at least to me).

Today, we’ve released news that HubSpot has just closed on another
$16 million funding round (our Series C) bringing our total capital raised to a
whopping $33 million. 

As I write this, I’m a bit worried that this article is going to come off as
arrogant and/or self-indulgent.  I promise that’s not my intent.  I’m just going
to let you “inside my brain” in the hopes that some of you will find the
excursion interesting, amusing or useful.  Although not all of you are out
raising money (thank goodness!), I thought you might want an insider’s view on
why an otherwise rational and pragmatic entrepreneur would make this kind of
leap.  I promise, the decision to raise this kind