Knowledgable Skeptics: When to listen to them, and when you should ignore them.

The best feedback I’ve gotten over the past year has been my blog post “Startup Handbook: How to identify and deal with the slow masses, knowledgeable skeptics, and savvy dreamers.” Since I spend about 99% of time on Twitter, CDC (Calacanis dot com), and Facebook promoting Mahalo (what can I do, I am what I am 🙂 I’ve decided to try to expand upon my advice for startups and entrepreneurs. Seems like most of the value people get out of CDC comes from my thought pieces on that topic.

Today I’d like to talk more about skeptics.

In it I define “knowledgeable skeptics” as such:

  • “These folks are smart and they get it your idea–they just don’t think it will work. They will, in fact, probably identify all the weaknesses in your business plan within 10 minutes of hearing it. They will interrupt you and shoot you down as quick as they can.”

Knowledgeable skeptics are invaluable because they are free consultants for your business. They may seem negative and harsh to savvy dreamers–as entrepreneurs tend to be–but if you forgive them for their nature you can get a lot out of them.

There are many more types of skeptics out there, so I thought today we would try to define some of them and discuss the best ways of dealing with them. There are skeptics all around us, and in fact there is a specific carear path for skeptics: journalism.

As many of you know (and many do not), I edited Silicon Alley Reporter magazine back and the day and hosted many conferences about the Web 1.0 era. We have 70 full-time employees at the company and our events had 500 to 2,500 people at them. At those events, and while doing the magazine, I played the skeptic. That’s the job of a journalist, you can’t hold it against them.

Of course, you can’t take it personal when they are skeptical because they are just doing their job. Let’s look at the range of skeptical jouranlists, VCs, and bloggers out there and how a startup should deal with them.

The Triple S

These are the surly, savvy, and skeptical folks. Om Malik, Michael Arrington, Kara Swisher, and Rafat Ali come to mind (just to name a few). If one of these folks comes after you, doesn’t like your startup, and/or thinks your ideas are stupid you’ve got a big problem because these folks ten to be right.

What defines a Triple S? They’ve probably:

  • a) been covering technology for over 10 years and have seen a couple of cycles.
  • b) have run, or are running, a business in the space. Mike, Om, and Rafat are owner/editors, and Kara might as well be since AllThingsD.com and the conference are run as a separate unit of Dow Jones.
  • c) been well respected for some time, even by the folks they slam, because they are freqently right.

How to deal with a Triple S:

  1. Thank them for their interest in your company. They’ve got plenty to right about, the fact that they’ve even taken the time is a blessing.
  2. Take their suggestions and issues to heart. They could be wrong sure, but they right more often than not. So, pretend they are right for a moment and “play out the scenario.” For example, if they said ‘Mahalo will never work because it will never scale’ your response would be ‘you’re correct, scaling the service is the biggest challenge. Any suggestion on how you would do that?’ What you’ll find is they will a) possible give you good suggestions, and/or b) respect you for not being delusional. Now, in this actual case I had an answer for this question that many asked, but I left it ambiguous and let them come to me with suggestions. The result? Many of them guessed that we were going to build a social network into Mahalo. The result of that? Entrepreneurial synchronicity!

Bottom line: You have to run your business, but courting these insiders for their sage advice is smart.

The Angry Skeptics
These folks are your biggest headache because they are wired to not only be skeptical, but they are also angry in their nature. They might have a valid criticism of you, your product, and your vision, but it’s going to be layered in anger. These folks come in two flavors: credible and standard. Dave Winer would be your classic credible angry skeptic, and Allen Stern from Center networks would be your standard Angry Skeptic.

Dave has done some successful things, so his opinion is not ill-informed, however much of this advice flows from anger. Let’s not get into where that anger comes from, let’s focus on how it manifests itself: an assult on you, your company, and your vision. If you look at Dave’s blog over the years he will fall in love with a product/person and then attack. Adam Curry was his podcasting partner in crime before they had a falling out. Twitter was his favorite thing since sliced bread, now he’s trying to make a competitor.

Angry skeptics lack empathy and their critisism is based on a toxic combination of that lack of empathy, general anger, and some logic.

Here’s how to deal with the Angry Skeptics, you have two choices:

  1. Ignore them: This is what someone like Evan Williams and Adam Curry have done. Why waste your life on them.
  2. Mix it up with them: If they’re going to attack you then you might as well get the satisfaction of attacking them headon and forcing them to watch your success.

Bottom line: Don’t bother trying to covert, ignore or attack.

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