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Some of our companies started financing processes in earlier this quarter. At a strategy session with one of our companies, the team and I crafted the outline of the pitch deck. They asked me what questions a venture investor might ask in the initial meeting.

Distilling the investment analysis into a small number of general questions is challenging because of the diversity of businesses we see but, I gave it a try and came up with the following questions I might ask a startup to answer in an initial meeting.

Though the industry is called venture capital, the goal of a VC isn’t to maximize every risk. Instead, we try to understand all the risks a business might face and weigh those risks with the reward - the exit. Here are the major risks that I typically review when a startup pitches.

Market timing risk - Is now the right time for the business? It’s often hard to evaluate this risk, but nevertheless, it’s an important consideration. There are many stories of people saying I invented Facebook before Facebook, which may very well be true. But the market just wasn’t yet ready for it.

When deciding if to raise a venture round, it’s critical to ensure your venture investor shares the vision for the company: both the product roadmap and the financial goals of the company.

Most founders never consider the impact on fund size on VC motivations. As long as there are enough reserves to invest as the company grows, a founder might think, that’s fine with me.

But this is naive. Fund sizes dictate a VC’s strategy. To achieve their target returns, a $50M fund and a $500M fund must pursue very different investment and management styles.

With the analytics tools today, it’s easy to measure hundreds if not thousands of different metrics for your business. Cutting through all the chaff to determine the most important or insightful metrics can be quite a challenge.

Below are the ten metrics I’ve found to be most useful in board meetings. They answer the questions of how should a startup founder might measure the business at the highest level. You should have many more metrics than these, but I’ve highlighted the ones that I recommend presenting to your board and reviewing each week.

If at any time in the past ten years, you might have asked someone at Intuit about the size of the QuickBooks user base, they would have told you the same number: about 4M.

This figure hasn’t grown because Intuit’s customer base, the small-and-medium business market, is a leaky bucket. On the small end of the spectrum, about 750,000 businesses are created each year and about the same number fail. On the upper end of the spectrum, successful medium sized businesses (and the larger, more valuable Quickbooks customers) outgrow Intuit’s products and upgrade to enterprise accounting packages provided by Oracle and others of their ilk. It’s no surprise then that QuickBooks suffers from high churn rates, characteristic of the SMB market.

Over the past few weeks, there has been a new refrain among consumer mobile startups that I’ve met with: we’re designing for normal people or normals as Chris Dixon would put it.

There are a few reasons for this trend. First, there is a movement towards great design. Second, there is a wave to reinvent and reimagine core applications of the mobile phones. The apps shipped with the standard OS were ports of their desktop counterparts. Only now, after using these cloned applications for a while, do we understand how email, phone, calendar, etc should evolve. Third, machine learning technologies make magical experiences possible like priority inbox or Google Now.

You fool! You fell victim to one of the classic blunders - The most famous of which is “never get involved in a land war in Asia”

There is a land war being fought on the web and it’s for files and filesystems. Incumbents and startups alike are duking it out. And things are really starting to get interesting.

The startups, Dropbox and Evernote, reinvented the file system as a synchronized, cross platform file system abstracting the hardware and the data. Now they are moving up the stack. Dropbox’s acquisition of Mailbox and renewed focus on photographs and attachments and Evernote’s every growing battery of point applications like Skitch, Food, Hello and Peek aim to drive further file creation and user engagement within their notebooks.

An entrepreneur shared this quote with me a few weeks ago.

The future is already here – it’s just not evenly distributed.
William Gibson, quoted in The Economist, December 4, 2003

I remembered it this morning when I drove past a Google self-driving car and then again a few minutes later when a Tesla whipped past me and a third time during the same commute when I dictated an email to my mobile phone. Sometimes living in the Bay Area does feel like the living in future.

Steve Sinofsky, executive at Microsoft for 24 years penned an insightful post on the five data biases plaguing product decisions. It can be easy for any founder, product manager, marketer or engineer accept a data point at face value as the rationale behind a decision.

But understanding the nuances and biases of the data, questioning the data, is often just as important as the result. The corollary point argued in his post is data isn’t strategy - data can’t be blindly used to inform product design and decision making because the data might be “lies, damned lies and statistics”.

In social media, like the real world, there’s quite a lot of gossip going on behind your back. At least on the Internet, you can measure it.

Dubbed dark social, this “invisible” sharing brings 40% of the visitors to my blog and similar amounts of traffic to other content sites. The Atlantic Monthly, which receives 5M monthly uniques, reports 60% of traffic from dark social

Like its distant cousin dark energy, dark social is a massive and to date little understood force despite its importance. Dark social clicks originate from instant messages, emails containing links and links embedded in tweets opened in TweetDeck among other sources.