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I don't know Jason Calacanis, but I get a couple of things out of this. (and yea, I know my two main points are contradictive)

1. Mahalo is blowing in the wind. I have no idea what Mahalo is or what Calacanis wants it to be. SEOing the hell out of near-worthless content is not a long-term strategy. If you want to win - solve a problem!

2. Jason Calacanis is an excellent executive. This Google algo change took place on Fri/Sat. By Tuesday this guy made the huge, painful, most difficult call in the world and laid off 10% of his company. If you have ever had to lay people off - you know what I mean. It is hard, it is painful, it is life changing. I wouldn't wish it on my worst enemy. I understand that the employee takes the blunt of the blow - but believe me, being on the other side of the table is not a desirable place to be.

I know this is not a popular stance on HN, but I have a lot of respect for Calacanis. The guy has done so much for the start up community. TWiST is some of the most valuable content I have found on the web and The Launch Conference - if it hasn't already - will change the startup conference scene forever. Not to mention his home brewed angel network that tilts the table in favor of entrepreneurs.

Calacanis is a hell of a self-promoter - but even if he rubs you the wrong way - you should respect what he has been able to do. If you have been (or were) on 60 minutes talking about internet startups...in your 20's...feel free to rip him apart. If not, show a little respect for what he has done and little empathy for what the guy just had to do.



NEGATIVE:

1) Jason and Mahalo are over. Their new strategy is very expensive and a multi-year road before it's a real business. It's a total rewrite, not a pivot by any means, if they do it well. No way Calacanis lasts a few more years at Mahalo (even if the board doesn't push him out).

2) Calacanis isn't really in charge at Mahalo AFAIK. The employees all report to Jason Rapp. Rapp and the board probably made the decision to layoff, though Calacanis was probably involved. He's being allowed to save face and ego. His role is more of a spokesperson than a CEO.

I think Calacanis simply can't force himself to do what it takes to make Mahalo successful because he's already rich. He's referred to Mahalo as "freeroll" meaning that even if it fails he's still rich. That kind of attitude is fine for getting things you love done, but it doesn't work when you're trying to do something you're not innately passionate about. He doesn't have the hunger (nor would almost anyone) to make Mahalo the kind of success it needs to be to justify its investment.

Paul Graham has said many times that he wouldn't start another startup because it's just too painful and he knows he couldn't stomach it now that he doesn't have the incentive he did before (to get rich).

I don't think there's anything wrong with this. It's natural human behavior to respond to incentives. I think when Calacanis finally realizes (or admits) this he'll be a much happier (if ego-bruised) guy.

POSITIVE:

Calacanis is unbelievably awesome when he's doing things he's passion about. TWiST and LAUNCH are flawless. He's the target demographic for the content himself and it shows.

He should turn LAUNCH newsletter into a head-to-head blog competitor to TechCrunch. Combined with TWiST and LAUNCH conference it really could become as influential and big as TC is.

He's got a ton of talent and energy, but I think Mahalo really drags him down. If he removed that burden he'd be able to do something truly amazing and big.

tl;dr: If you're already rich don't try to do things that you aren't genuinely passionate about, your subconscious will prevent you from doing what it takes to succeed that way. Stick to things you don't have to force yourself to do and are naturally good at.


This entire comment is predicated on the assumption that getting rich is the underlying reason entrepreneurs build businesses. I disagree with this assumption.


I believe the major assumption is actually that getting rich is the underlying reason entrepreneurs build businesses that they are not passionate about. Of course, "getting rich" could be something to be passionate about, but I don't think that precludes other sources of motivation.




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