Today at Gnomedex there was a fascinating interaction between the user-centric Gnomedex crowd and Jason Calacanis. Jason, as you know from previous interactions and engagements on the web and on this blog, is the founder of several successful companies. His current project is the much maligned Mahalo which figures to despam the internet by providing human created search results. I didn’t understand the business before and after hearing him speak today, I don’t understand it now.

I encourage you to listen to the session which I’ve embedded below. In this session, which clips the beginning of the session where Dave Winer blasts him for engaging in “conference spam” after making villains of folks who may or may not legitimatlly also be using the internet for spam purposes.

I was happy to speak my own mind around 10 minutes into the video on an exchange that occurred right here on this blog back on July 18 where Jason promised me and others that there would be search results for the term “WordPress” in Mahalo by days end. As said in the session, I don’t really care that there isn’t but the fact that as of his session, August 11, there still was not any results demonstrates a principle that I’d like to talk about today in terms of trust and user perception in the success of a business. (Disclosure: there is now a WordPress Mahalo result page) But first, the video:

Now here’s the problem that Calacanis has. He has the authority to speak on entrepreneurial issues and he has the track record of success to believe that he can make a company like Mahalo work. He has a problem that the populous doesn’t believe him.

Brand is built on trust and perception and if people don’t trust you, they won’t trust your brand. It’s a principle. It’s tried and true. Geraldo Rivera can tell you that because he has been laughed off Fox News, despite his overwhelming success in previous ventures. George W. Bush can testify because he was a successful business owner prior to becoming the President of the United States and now has zero credibility.

The success of a company is as much entwined in the persona of who the founder is as the business model itself. In other words, Mahalo is doomed not because it’s a bad idea or has bad delivery (though that could certainly be argued in a different post), but because of Jason. We don’t trust Jason. We don’t sympathize with Jason. Jason has not won the hearts and minds of the people. You. And me. The readers. The proletariat. The longtail.

In order for Mahalo to be successful, there must be a critical mass in terms of adoption. Any idea can be good but if there is not market share, there is no value. Jason is challenged on every side. He is polarizing. He is not trusted.

I’m not making this stuff up to write a post villainizing Jason Calacanis. The Gnomedex user base speaks for itself.

Mahalo has a fantastic principle. Fight spam via human interaction and human generated search results. Eliminate conflict of interest by producing stringent content guidelines. Interact with community leaders by producing excellent evangelism of the product – such as what he has done on this blog.

The problem with Mahalo is largely not about Mahalo but about Jason. Jason has created a persona that causes people to dislike him and not trust him. Sure he is a successful entrepreneur, having created Weblogs Inc and the new Netscape. Sure he brings good ideas to the table and takes industry offenders to task. Sure he is an entrepreneur in residence at Sequoia Capital. But we don’t trust him. You and I. Readers. The average joe. The proletariat. The long tail.

With a crisis of conditions at hand, can we really expect success? I doubt it.

Of course, Calacanigroupies will probably stop by and praise Jason’s success in the past and claim that as a planted flag for future success. I think you don’t have to look past the opinions of those who followed Jason’s advertorial to hear the underlying message.

But few take the time to point out that his candidness is usually quite calculated and geared for maximum business leverage””thus, not truly candid. ~ Adario Strange, Wired Magazine

Jason is an interesting guy. He certainly likes attention, either good or bad. His new startup, Mahalo, is pretty… pretty… lame. I see so many problems that I probably need more time to write a full blog entry about the things that won’t work with it.

Either way, when you start justifying a new business “we want to go back to 1994 feeling when all the sites were good” it’s not the right start. Going back is never a good plan. Sorry. (quoted in full) ~Marcello Calbucci

Jason brought up many valid points about spam and the need for better search results. But I was disappointed that each point he made felt like a tailor-made opportunity to mention Mahalo. I think Winer was right to call him out. ~The Nordquist Blog

The people are speaking and I’m not convinced Jason will hear or understand – since understanding is as much a part of this as hearing is. Ultimately, rock solid business plans can only go as far as the trust of the user base and their ability to “buy in”. That’s my theory anyway.

Gnomedex Update: The spat has become known as being “Winered”. Dave challenges Jason and Jason counters. My additional contribution to this spat is only to ask Jason what he expected from Gnomedex. This is a user-centric, anti-establishment bloggers conference. You expect a free pass? Come on, mate!