Three Magical VC Pitch Questions

There are plenty of places throughout the blogosphere which talk about the typical VC meeting, delivering both advice and tips. (In that corpus, a while ago I blogged about seven mistakes that entrepreneurs often make during a pitch session.) Along those lines, I think the proverbial 12-slide deck helps provide structure to a conversation where a multitude of information needs to be communicated in a short (often an hour or less) period. There’s a reason that’s become “standard.” But after having had the privilege of meeting with hundreds (if not thousands) of entrepreneurs over the past seven years as a VC, I’ve also stumbled upon three non-standard questions which I very often ask during an initial meeting which help facilitate a discussion beyond just a rote “pitch.” The following that are three questions which I frequently ask that attempt to raise the level of discussion beyond that of a typical pitch and break the mold of a “typical VC meeting”:

What’s the founding story?

This question is my absolute favorite to ask when I first meet a team who is fundraising. The answer narrates how founders meet and eventually come together, how the idea for the current incarnation of the business emerged, and how the (inevitably) winding road of the initial days given rise to the current perspective and approach. In short – telling a founding story lends insight into all of the intangible details that make this start-up a unique coming together of real people, not just a valuable coming together of human and technological capital.

This narrative also speaks to the culture of the leading team and how it will spread through the others that will follow. And asking about the founding story ignites an entrepreneur’s passion which truly drives him/her beyond the facts and figures of the business. Whether it’s a relentless pursuit towards solving a problem or an “ah-hah” moment that a problem could be solved, the distinctive details which emerge from the founding narrative bring to light a set of information that few other questions could.

What is your “favorite future?”

Success takes on many forms. Of course a founder can generate a financial forecast and opine on potential exit options years from now for a pitch deck. But asking about a future scenario – again, a real story – that is his favorite, really lends insight into the goals, values, and assumptions embedded into the company. Giving the opportunity to hear one of the possible incarnations of what could happen to this company, really as the next chapter continuation of the founding story, sheds light onto the framework of how decisions are going to be made as the company matures.

What else should I be asking you?

This question is quintessentially open-ended. And great entrepreneurs thrive with the possibilities that a blank canvas provides. A non-specific inquiry sets the stage for an entrepreneur to talk about what s/he wants to talk about beyond the rigid/formality structure of a pitch deck. And to frame a question where the answer is a question itself creates a role reversal that bridges a connection between two of us in a conversation. This question can also drive a discussion towards the real meaningful core issues which will be pivotal in making an endeavor a success.


In sum, all three of these questions above are about context. They allow for a better understanding not of what “the pitch” is today, but rather where the company has been and where it is going, along with how the entrepreneur sees himself and his company in a greater landscape. It provides for an easier way to find a common language between two parties in a short one-hour meeting when the heart & soul of a startup is reduced to a dozen slides, which by definition is impossible to do.

But most of all, these questions opens the discussion to a true conversation – a meaningful dialog where there’s a real exchange back and forth between an investor and entrepreneur, not just a one-way monologue. This approach follows into the ethos which we live by here at NextView in treating each entrepreneur as we’re an “invited guest” at their table. It is my hope when asking these (hopefully thoughtful) questions during an initial meeting sets that very tone .

David Beisel

David Beisel is a co-founder and Partner at NextView Ventures. He has been focused on early stage Internet startups his entire career, both as an entrepreneur and venture capitalist. As an investor in the digital media space, David was most recently a Vice President at Venrock and previously a Principal at Masthead Venture Partners. Prior to becoming a venture capitalist, David co-founded Sombasa Media, an e-mail marketing company best known for its flagship product BargainDog. Sombasa was successfully acquired by where David served as Vice President of Marketing. David holds an MBA from the Stanford Graduate School of Business and an AB in Economics, magna cum laude and Phi Beta Kappa, from Duke University. He also founded and leads the Boston Innovators Group, an organization which holds quarterly entrepreneur events drawing a thousand attendees.