Thanks largely to the exposure of Fred Wilson’s kind words, my recent post on the Seven Founding Sins – common mistakes which often divert entrepreneurs off the path towards success – received a number of comments and feedback throughout the blogosphere. I’d recommend reading the original post, but the summary of the sins itemized are: inauthenticity, sloth, extravagance, taciturnity, greed, arrogance, and indecisiveness.

Given that I thought the discussion was interesting, I thought I would highlight a few others’ reactions. There were differing opinions as to which one people “liked best,” which lead me to believe that they indeed are all legitimate and important to avoid. However, my own personal favorite, inauthenticity, was discussed the most:

“Inauthenticity. While there are notable exceptions, most successful entrepreneurial endeavors are sprung from a genuine idea born from true experience or direct & tangible observation. A founding team should not only have the relevant experience, but also immediate and authentic understanding of the end-users’/customers’ need. Blank-slate brainstormed white-board ideas rarely even deserve the material that they’re written on. Great ideas search for a great entrepreneur; great entrepreneurs don’t search for a great idea.”

Fred Wilson agreed with the notion,

“Exactly… We look for entrepreneurs who have lived the pain point they intend to address.”

Rags Gupta, however, pointed out a number of successful companies were established with that the search, not the problem, coming first,

“While entrepreneurs certainly need to be intimately familiar with the problems they’re trying to solve, I also believe great entrepreneurs can search for great ideas. The stuff that’s come out of Bill Gross and his Idealab is probably Exhibit A here. While they got a lot of flak during the dotcom boom and bust, what got lost in all of it was the great ideas (and companies) that they spawned: Goto (Overture) — the idea of having sponsored search results was a bold one, Snap, Citysearch, and several others.”

And finally, Charlie Wood claimed that identifying an authentic idea and entrepreneur is easy (especially compared those of the other traits):

This sin is easy to identify: the entrepreneur can only talk about the macro-scale idea, not the details. He can talk about the problem he’s trying to solve in the abstract, but can’t give real-world examples. He parrots what the press and analysts are saying, and rarely contradicts them. And he’s hesitant to admit the limits of his knowledge in the domain space.

On the other hand, authenticity is just as easy to identify. The entrepreneur will spend less time trying to convince you that he has a great idea and more time demonstrating it to you. He’ll talk about what the potential problems are. He won’t get tripped up on terminology, since it really doesn’t matter. And people will find uses for his idea that he never imagined.

I first heard someone mention the benefit of an entrepreneur’s authenticity when Mark Leslie spoke about it at length, and it struck a deep chord with me. It seemed to go right to the essence of addressing the intrinsic rewards which I think motivate entrepreneurs in addition to external financial gain. Entrepreneurs addressing problems or opportunities that they have seen or observed first hand are creating a real solution, not just a business. Of course we can cite many counter-examples of entrepreneurs searching for an idea as opposed to the other way around, but we can find opposing instances for probably all of the sins enumerated.

I am not putting forth that if someone makes any one of these mistakes, that his/her start-up endeavor will be unsuccessful. Hardly. What I am suggesting is that demonstrating the qualities these is like running against the wind – you may get there anyway, but it’s definitely going to be a more difficult race. An idea and entrepreneur that is authentic starts from a right place at the core, which in turn pushes him/her to be energetic, responsible, communicative, generous, confident, and focused. And hopefully, that much more likely to be successful.