Five Fundamental Questions

… for the entrepreneur.

Shourov Bhattacharya
4 min readSep 22, 2019
Photograph - Damien Liviciche

I’ve been out and about having a lot of coffees and croissants, meeting a lot of people — customers and investors — talking to them about my new venture/s. As I encounter questions, I note them down in my own list of Frequently Asked Questions (FAQs).

But the list has grown longer, and last week I had the idea of organizing them into categories. I found to my surprise that they naturally split into just five categories — I expected more. Then, I found that every category could be described by a “fundamental” question that captured the essence of all the specific questions within it.

Think of it like the ancient Greeks — they believed that the universe was composed of four elements (air, earth, fire and water) and that any substance was just a variation and/or combination of these. If you’re an entrepeneur with something new for the market, these five fundamental questions are the basic elements of all conversation and enquiry from your customers and investors.

Having answers to these fundamental questions clarifies and organizes your thinking. Of course you still specifically prepare for specific questions from specific parties. But your understanding of these fundamental questions makes an answer to any question more compelling, because you will naturally address the deeper question “behind” the question.

Anyway, it’s helped me a lot and so I thought I should share it. So here goes.

  1. Does it work [well] ?

A common question at an early stage of your venture. Does your thing do the basic function that is the promise of the thing? Questions about quality and effectiveness are also just variations of this, as they are asking the same thing but applying a threshold somewhere above zero to gate success/failure.

For example, if it’s a croissant, does it look and taste croissant-y and crumble like a croissant does? Or is it croissant-y enough that it reminds you of that time you arrived in Paris on your honeymoon and had breakfast in that little place behind your hotel?

Ideal answer: A demo or proof-of-concept (PoC) delivered on the spot — a bite of the croissant is all you need to never ask this question again.

2. Who [else] wants it?

Business people in general are herd animals — and before they join, they want to know there is a herd in the first place. Even just a few other people who love your thing are super valuable here. No one, in my experience, argues with the market. Buzzwords like “validation” and “product-market fit” are really just abstract and intellectualized versions of this fundamental question. People are kind of just asking — do you have an audience?

[A special note— it may not be obvious but that old chestnut of “what problem are you solving” actually belongs here too. A problem maps directly to an audience of problem-”havers”. And if you show someone an audience that loves your thing they never ask the “problem” question.]

Ideal answer: Having some early-adopters/users/fans handy is awesome, or at least some evidence that they exist. Ideally you point outside to that crowd on the footpath messing up their suit jackets with croissant flakes.

3. Who are you? And why you?

Two questions, I know. But they are interlinked.

Your story is always important and relevant. Different people have different ways of approaching this — some like name dropping or long resumes, some need social proof — but everyone will listen to your story if you tell it. Not as a self-promotion, a la social media, but just as a simple story. People need to connect even if they pretend that they don’t.

And your why — your vision — is inextricably linked to your presence. I’ve never put forward one without the other. If you tell your story with clarity and authenticity, the why behind your venture will be self-evident.

Ideal answer: I’m me — with a brief backstory. But the real answer isn’t in the words but in your presence. No one has to ask a French pastry chef why s/he makes croissants.

4. Do you have a plan?

Got a plan? Good, because almost no one will want to see it — they just want to know that you have one. Our culture fetishizes plans and plan-makers. There are endless variations to this question, everything from asking about legals to revenue models to competitor analyses to marketing strategy, but they’re all just pointing back to this same fundamental question. Again, the actual plans and artefacts themselves don’t matter as much as their value as signals of competence (and confidence).

Besides, smart people understand the planning fallacy, which is even worse for an entrepreneur because you are doing something new (e.g. no one ever built a worldwide croissant supply chain before).

Ideal answer: An unequivocal “yes”.

5. Are you going to make it?

Now that you’ve dealt with fear in the previous four questions, you can appeal to hope with your answer to this one (this is about right — non-entrepreneurs operate about 80% on fear). Investors in particular have a million ways to cut this, but in the end they all just want to see a trajectory going up. Everyone wants to be a part of success. The irony/paradox of entrepreneurship is that most people will only (finally) be ready to join you once you don’t need them to join any more.

Of all the fundamental questions, this is the one that needs an answer not so much in words but in a feeling. Actually, you might never get asked this question at all — but you’ll definitely have to answer it.

Ideal answer: A smile. And another croissant. :)

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