As Mike Arrington has proven, a large part of growing your presence on the internet (read: becoming known by the masses) involves selling out and engaging in morally questionable activity (not to mention evolving into an enormous dick). Om is probably glad that he didn't compromise his integrity like Arrington did to get attention of the masses. He gets more than enough attention from those that matter.
Probably not. His demographics are epic. Random refreshes of Gigaom give me the following ads in the "lead" spot:
* Sprint
* Best Buy
* Cisco
* Brightcove
The same exercise on TechCrunch gives me:
* Google ads
* Graphical Google ads
* Google ads
* Google ads
Techcrunch runs way more ads per page. Based on the prices of those sponsorship squares ($15,000/mo for ~20 million impressions = ~$.75/cpm), I'm guessing they're all pretty bargain basement. It's just not worth running stuff like that if you're a site like Gigaom.
So that's the measure of success? If I were Om, I'd be sad about being compared to the sensational journalism of Mashable, or the world according to Arrington.
Om's content is far better than the other 2, but that's just my opinion.
For me GigaOm's, or, ReadWriteWeb's content for example, is better than the other two. Mashable is quite good for Social Media News, even if it's sensational.
I'm wondering though if the quality content of GigaOm with fewer readers (how many GigaOm Pro subscribers might there be?) makes him "happy" in terms of revenue.
I don't think he's sad. He caters to a smaller (and I think more influential) audience than TechCrunch/Mashable. His site produces really awesome content with deep/thoughtful analysis. He seems to really enjoy life.
The way to win in the TechCrunch war isn't something that Om wanted to engage in, I think. He doesn't do linkbait, doesn't stir controversy, doesn't declare crusades.
Did he miss a financial opportunity? Maybe. Should you be sad about missing a financial opportunity? Nope. Having met and talked to both of them for a while, Mike Arrington seems more sad than Om does. Money/success, beyond a certain level, ceases to correlate with happiness.
Oh, Om was also asked to be a partner in one of the best/most active early stage VC firms in the Valley (True Ventures-- full disclosure, they participated in our Series A).
