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Pricing is one of the most challenging decisions for any startup. One of the simplest ways of discovering customer willingness to pay is simply to ask them.

At first blush, that might seem a reasonable and effective solution, it is prone to wild inaccuracy. Absolute pricing judgments are hard without reference points. For example:

How much would you be willing to pay for a new iPhone?

It’s a very challenging question to answer in the abstract. It all depends on what the phone can do and what sacrifices I would have to make to be able to afford that phone. That calculus isn’t any different for smart phones, expense management software, or flash storage. Every pricing conversation is a game of trade-offs.

I once read a book by Antonio Damasio, a neuroscientist researching decision-making from USC, about a man who had lost the capacity to feel emotions after he was struck by lightning. Much to my surprise, his man was totally incapable of making decisions.

His cognitive ability, the capacity to process and analyze data, remained fully intact. He could articulate the pros and cons of every alternative to each decision. His logical ability was flawless. But, he never could decide on an option.

Over the past 15 years, we’ve seen a wholesale migration of software development on the web towards cloud away from client/server models. The cloud offers many benefits: seamless upgrades, synchronization of data across different devices and lesser hardware requirements.

But the cloud centralizes all the data. All of our Dropbox files, Google documents, and emails are held within one or few companies' servers - which provides easy access for hackers and government.

Reading TechMeme and HackerNews this morning, you’ll find more stories about legal issues relating to technology than stories about innovation: the PRISM affair, the DoJ’s suit against Apple for anticompetitive ebook pricing, Samsung’s win of a sales injunction banning iPhones and iPads, Chinese hacking of US assets, patent trolling and reform and so on.

It’s frustrating. But this isn’t a trend that will reverse its course.

In the center of this firestorm is the user and his data, bewildered by the scale and magnitude of these confrontations.

The reason most startups go out of business is they run out of money. The CEO bears the responsibility for raising money, managing those assets and growing the business into profitability and ultimate sustainability.

But the CEO shouldn’t bear this load alone. To help defray that critical responsibility, the CEO ought to have a consigliere, an advisor who helps plan, allocate resources, and illuminate the trade-offs between decisions. That consigliere is the head of finance and the most under-appreciated startup team member.

We all type quite a bit. I’ve never measured how many words each day I type but I imagine it’s probably a few thousand each week between my laptop and my mobile phone and across emails and blog posts. And no one can deny the toll this takes on our wrists.

In the past week, I’ve been suffering from some carpal tunnel pain particularly as I’ve been coding more. Coding often requires all kinds of odd key combinations because of the varying syntaxes of CSS, Ruby, R, MySQL and the English language.

Do you measure your product’s time to utility? If not, you should.

The best products reward users as quickly as possible after installation and account creation. But it’s easy to forget about this and as a result, watch conversion rates from download/install-to-active fall.

CRM products have the longest time to utility of most software products. The end user, a salesperson, logs into a blank Salesforce installation. She must type in a bunch of data about a customer. If the customer account closes, great. But it’s not until twelve or eighteen months later when the customer considers renewal and she has to strategize how best to pitch the customer that this salesperson benefits from any of the data entered into the CRM.

As the number of Android users continues approach 1B devices, more and more startups are looking to deploy complementary applications on Android, in addition to their iOS applications. Some startups are beginning looking to launch on Android first. But the dynamics of the Android app store are quite different from iOS. In fact, they are much more challenging for startups.

Like iOS’s app store, Android’s app store also ranks applications. But the ranking system is very different in four key ways:

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Last night, Elon Musk inspired the audience at D. It is hard to overstate the scope and breadth of his ambitions or the impact of his start ups PayPal, Tesla, and SpaceX on payments, automobiles and space.

Behind the desire to listen to great men like Musk speak about their perspectives is a hope to receive some insight, some pearl of wisdom. Last night, I came away with two of those both about startups.

At the D conference yesterday, Tim Cook said many things without saying much. But one story did strike me. Cook described the product management and strategy process at Apple.

Walt Mossberg asked Cook why the iPhone has only one flavor when the iPod had so many including the shuffle, the nano, the mini, and the classic. Even though both products originally launched as a single model, the iPod flourished into a family of products while the iPhone has remained a single SKU.