Robert Go of Spark Capital recently wrote a post on "What VCs Really Want to Know" asserting that there are often questions a Venture Capitalist will ask that cannot be answered realistically. Rob essentially states that the focus of startups should be on execution, and not necessarily long term planning or metrics that are vague guesses due to their rapidly shifting nature.  However, he goes on to list the 5 "questions beyond the question" to assist all of us. They are: 1. Is this an attractive industry and how do you win? Hopefully, you've targeted a VC that has a clue about your industry, but our knowledge is usually not nearly as deep as it could be.  Help us understand the trends, customer challenges, and business levers that matter. 2. Is this a good entrepreneur? The entire fundraising process is an evaluation of the entrepreneur.  We want to know how resourceful you are, how self aware you are, whether great people will work for you, and whether you can withstand the challenges of a startup.  A lot of the questions I ask are meant to understand how an entrepreneur thinks and will respond to the challenges of the entrepreneurial process.  In a way, I'm also asking myself "if I were interviewing for a job with this person, would these answers give me confidence to work for them?"  Also, I'm trying to figure out whether this entrepreneur is trustworthy and listens to feedback.  It's great when entrepreneurs realize that I'm hung up on a particular problem about their business and comes back later with a potential solution and plan to test it.  It's not great when an entrepreneur tells me about a customer they are about to sign and the diligence shows that they've only spoken to the company once. 3. Does this entrepreneur understand the business she is getting into? Even if startups have a lot of uncertainty, there is a big difference between entrepreneurs who understand their business and those that don't.  Experienced consumer internet executives rarely say: "we will acquire customers through word of mouth and Web 2.0 techniques."  Instead, they have very specific thoughts about distribution partners, specific social media outlets they can tap, how to market effectively through SEM and SEO, etc.  I want to back an entrepreneur who demonstrates intimate knowledge of the industry she is focused on, even if she has never worked in that industry before.  History is littered with previously successful entrepreneurs who failed because they went after a market they did not understand. 4. Will this entrepreneur spend my money wisely? This isn't just about being cheap.  It's about investing in the right areas at the right time in the right amounts.  I want every dollar spent to reduce as much risk as possible or increase as much upside as possible (or both).  This usually comes back to #2 and #3.  Good entrepreneurs may say something like this: "I know I can't get scale in this business by selling directly.  I need channel partners.  But I DON'T know what customer segments I should be targeting first. So, I will spend a little money to test my product with a bunch of customers before spending a lot of time and money marketing the product and securing a big channel partner." Bad entrepreneurs will spend millions of dollars building a product and millions more marketing a product before realizing that no one really wants it.  Shockingly, this happens a lot more than people think. 5. Do I believe in the proposed product? This is very hard to figure out.  Usually, this is answered by a combination of a) customer feedback or b) gut.  Customer feedback means lots of people are using the product (aka traction), or we have called a bunch of potential customers and done technical due diligence and the feedback is positive. Gut means that we have a strong point of view of how the market will evolve and what solutions will be important, and your product meets that vision. Our own NH-based venture capitalist, Jesse Devitte from Borealis Ventures adds a couple key points that are important to consider: Does the entrepreneur understand the items, like market forces, that are bigger than the company itself and may indeed represent the largest single impact on the companies ability to succeed? Lastly Jesse states; My own test at a general level is not to focus on the answers to the standard questions, but on the thoughts that go into the answers and specifically is the entrepreneur being realistic. So, what would you add to this list?  Or, if you have pitched a venture capitalist lately - what did you include in your slide deck? Looking forward to the comments! - Jeffrey Vocell