This guy is being way too hard on himself. Running out of cash is hard and painful enough, no need to unduly heap blame upon oneself. If people at IBM were talking to him about a deal, then they weren't doing it to coddle his startup or be nice... trust me, if people aren't interested they won't be shy about saying no. I think he got caught out by the slow-moving bureaucracy of a big firm... too bad for them, their loss. As for IBM being a stalwart of the tech industry not needing help from a brash young startup, isn't that exactly how Microsoft got its first big contract?

This wasn't a case of needing harsher advice (too many people are addicted to self-flagellation, as if crushing your own dreams was a sign of maturity) but a case where a fledgling company took a big risk. Risks are risks, there's no way to to apportion blame or change course in hindsight. This just as easily could have been a post thanking his many mentors for their sound advice and encouragement that saw him through to getting his first big sale to IBM. Just because the other party in a negotiation is a big corporation that lumbers along and takes forever to make up its mind, there's no need to berate oneself for not having tried harder or seen x,y,z in retrospect. I say good on him for having gone balls to the wall to bring his vision to life, and good luck with his current venture. But the lesson here is not about advisers, in my view, it is about caution when dealing with massive organizations.