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Danny Brown

Danny Brown

podcaster - author - creator

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jason calacanis

Why Jason Calacanis is the Ultimate Twitter Fail Whale

I don’t like openly criticizing people, but Jason Calacanis is the equivalent of the Twitter fail whale.

Now I’ve mentioned Calacanis in this blog before, and actually stated that while he may not be my cup of tea, I did find his “never-say-die” approach was better than a negative one. However, all that has changed and for the award for the human version of the Twitter fail whale, Jason Calacanis takes first place.

Why? Simple – his recent actions have shown him to be a pretty shallow creature.

Never one to back off from blowing his own horn, Calacanis recently had to let 10% of his employees go due to the current lack of advertising in the online market. Calacanis is the CEO of Mahalo, a “human powered search engine” that needs advertising income.

At the time, Calacanis stated, “It’s my responsibility to make this hard decision and I don’t take it lightly.” He also mentioned, “We’ve got a significant amount of cash on hand… The net result of this effort is we are giving Mahalo another year…”.

Reading that, you may feel that this is the difficult and upsetting decisions that many CEO’s have to make when times are tough – to keep the company going, sometimes people have to be sacrificed. It’s not pleasant, particularly for those let go, but then if the company can survive and then re-employ at a later date, it’s a decision that has to be made.

You would have thought that. Until you learn that Jason Calacanis is picking up a new $109,000 Tesla Roadster this weekend. Until you learn that Jason Calacanis is boasting about picking up his car and asking his Twitter followers if they know any media types that would be interested in going along to record the pick-up.

If Calacanis was really interested in the best interests of his company and his employees, then he wouldn’t be wasting $109,000 on a frivolous purchase. Yes, even in times of difficulty businesses still need to spend money to try and keep the business going. Yet this is normally for new IT systems that can improve performance, or core company-specific needs.

A $109,000 sports car? I don’t think so.

So enjoy your new car, Jason. Enjoy the “fresh from the showroom” smell and the adoring looks in the mirror. For when your company goes through even tougher times and you have to lay off more employees – the people who really make your business – at least you’ll have a nice car to drive to your computer to send out another sob story.

So, congratulations. For the inaugural Twitter Fail Whale Award – Jason Calacanis, come on down.

Jason Calacanis and the Contradiction of What Defines Great

I’ll be the first to admit that I’m not a huge fan of Jason Calacanis. The entrepreneurial CEO of Mahalo, and the co-founder of Weblogs, Inc and TechCrunch50, Calacanis is the epitome of self-promotion and flag-waving. However, that’s not to say it’s wrong – it’s just an approach I’ve never favored.

Additionally, there’s no doubting that Calacanis has a never-say-die attitude that, while potentially grating, is better than the fatalistic approach that too many people take when faced with any kind of crisis. However, a recent jobs posting for his company Mahalo seems to contradict everything he advises his readers.

Posted on the Fresno area job board of Craigslist, this is the description for positions available at Mahalo:

  • Mahalo.com seeks freelance remote writers to build search results pages on breaking news, politics and entertainment topics. Candidates must be excellent writers capable of creating perfect, concise copy at a fast pace. Familiarity with online research, journalism and wiki markup language strongly recommended. Shifts are flexible, ability to work weekends/nights a plus. Pay: $10 – $12 / hour. Please attach your resume and writing samples in an email with subject line: “Remote Guide Application” to evanb@mahalo.com.

While any company hiring in these times of uncertainty should be applauded, the job posting raises other questions, due to the views Calacanis shared with his email subscribers in a recent newsletter (also available at his website). When talking about how to improve your company’s success, Calacanis writes:

  • 3. Firing the average people: Again, it?s totally politically incorrect, but I highly recommend firing anyone who is good or average. Startups are an Olympic sport and every slot on your team is critical. You wouldn?t put a ?good? swimmer in a relay, would you? Don?t have one in your startup. Fire the good and replace them with the great.

If indeed the right thing to do is fire anyone that’s doing a good job at a company (something I’m against – I tend to find the good workers are the ones that give the superstars the solid platform from which to work), then the economic crisis must be really hitting home. I can’t think of how else Mahalo will attract superstars with an hourly pay rate that may be able to buy a movie ticket.

Unless it’s an example of another piece of Calacanis’s advice: “Cut spending everywhere you can.”

© 2026 Danny Brown - Made with ♥ on Genesis