We Got Sad Angels and Mad Angels, But Not So Many Glad Angels After Boston Angel Dinner

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founder of HubSpot and another prominent Boston angel, who missed the dinner. “Although I haven’t been doing angel investing that long (and am likely young and naive like you), my optimism level is still pretty high,” Shah wrote. “I’ve made more angel investments this year than ever.”

Kane, who was at the dinner, commented that he wasn’t really sure what Go meant about not caring about average rates of return, and continued:

But if I get the gist of it, well, I’d love to hear you tell that to your LPs, if and when you raise money from LPs…Returns are really all that should and do matter to professional investors.

Which brings me to what I infer is your proposed remedy for us, tired, old fogey, just don’t “get it” angel investors—we should all take the red pill (or was that the blue pill?) and start acting like, well, amateurs. To hell with due diligence! To hell with caring about returns!

That sparked some more exchanges between Go and Kane, who eventually appear to have found peace. Go admitted that he didn’t mean to disparage the importance of returns and that in parts of his post: “I guess the tone was a bit overboard.”

Landry also weighed in with passion, as is his style—and maybe a reference that Go won’t be invited to another such dinner (read on):

Rob.. I guess I didn’t find the negativity you’re referencing so pervasive at that dinner…nor did I find the conversation ‘lame’. I thought it was actually a good (and sometimes fun) discussion of some of the issues that should be discussed by some folks that have, yes, some experience! Despite all the innovation enthusiasm which I share with you, investing is still investing, or at least gambling but certainly not picking charities for contributions. Losing money isn’t that much fun—but worse, it doesn’t inspire more investments!

Later, Landry wrote:

“You were invited as an fellow investor meant to contribute THERE, not as an uninvited Michael Arrington taking shots at a distance and stirring a comment pot. The fact that you’ve used your blog to suggest the issues that you thought should be discussed, but yet did not offer them in the dinner discussion YOURSELF leaves me perplexed.

Worse, this kind of post suppresses intelligent discourse about topics that at least I think need discussing. Now these angels and more will be increasingly reluctant to discuss THEIR ideas and experiences with others at future forums or dinners, and sadly for you, particularly if you’re there.

Where’s the good? Sad indeed.”

At least one entrepreneur, Derek Skaletsky (who it doesn’t appear was at the dinner), largely agreed with Go.

“hey Rob—thanks for having the stones to write this. from the entrepreneurial side, we couldn’t agree more and have unfortunately made the decision to move the company because of it. my suggestion to you is to stop going to these gatherings. if you want to be extraordinary, stop hanging out with people that don’t contribute to that end…cheers!

What do you think? Are Boston area angels too conservative and defensive? Or is Rob Go just a naïve young investor? Should he have aired his concerns publicly, or kept them private, which itself might be a conservative Boston tradition?

I have a prediction, though: A bunch of entrepreneurs, especially those who haven’t had good luck with Boston angels might well agree with Go. (I’m perhaps biased in the other direction, though, as Xconomy is funded almost entirely by angels, including Landry and Shah.) But I think LPs he is trying to attract might not feel quite the same.

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Bob is Xconomy's founder and chairman. You can email him at [email protected] Follow @bbuderi

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