If you are alive in 2024 (and given you are reading this blog, chances are that you are), you have to know a founder or two. And if you live in Bengaluru, it’s likely your local Barista, your ex-girlfriend, and your high-schooler neighbour are working on a startup idea — together. 

So, given this surfeit of founders in your vicinity, you probably know by now what to say to get them grinning from ear to ear. (Ask them about their first-born, first-born startup that is, compliment them on their CAC, the usual). 

But did you know that there are some things you absolutely must NOT say?

Yes, today I am here to talk about those questions that you must never ask a founder, no matter how strongly you feel the urge to. 

Treat this guideline as precious insight into a befuddling group of individuals or as insurance for when the founder in your life hits the big time. 

So how is it going?

The “it” in question is the startup. 

Now we understand the intent, we really do. People want to show interest, bless them. And they probably expect a platitude in response, such as “Oh, you know, same old” or “Things are ok, can’t complain”. Corporate folks have fine-tuned these responses to an art form, let’s give credit where it’s due. 

But ask a founder how it is going, and you will witness a breakdown. 

While you chomp on your starter, waiting for a banal response that allows the table to move on, the entire life of a founder will flash in front of their eyes. Metrics will come to their fevered mind, an update on funding perhaps, or the latest organizational challenge? Caught between their many avatars, the hapless founder will wonder which one to trot out for this audience — the optimistic, the brazen or the honest. And if they are given to reflection, they may even start pondering the very question — how, indeed, is it going? 

In short, their brain will short-circuit, and before you know it, you will have one frazzled founder on your hands, who either won’t talk or won’t stop talking. 

Also Read: Why finding your co-founder is a lot like meeting your soulmate

So my suggestion is to attempt at your own risk. 

When are you retiring?

Now, I know there are people who plan their lives around their financial goals. They share analyses about money to save up by varying ages of retirement. They buy homes and dream of buying more homes. 

None of them are founders. For, founders don’t have financial goals. They have financial hopes and financial dreams, which are often nested in the ambition they have for their companies and a byproduct of their efforts towards realizing them. 

That ambition could be big or small, slow or fast, but either way, it does not involve a steadily accumulating nest egg to keep you warm and cosy through the uncertain nights. 

How was your vacation?

Now, I have to admit I am more privileged than most, and with my partner being one of the steady paycheck types, we do go on vacation.

But no one can accuse me of enjoying said vacation. 

Founders don’t let go, they don’t relax, they don’t enjoy breaks. Oh, it’s possible they may not always be hustling towards a deadline or making pitch decks, but vacate. They simply do not. 

The red of the setting sun reminds them of the red in their PnLs. White sands are reminiscent of the white spaces yet to conquer. And every fellow vacationer is a prospective client, yet untapped.  

So the next time you ask a founder about their vacation, don’t pay heed to the words but look into their eyes, look under their eyes, and ask yourself if that harried countenance is indeed that of one who has enjoyed relaxation recently. The answer will be obvious. 

And finally…

What about your funding?

Let it come to you, dear people. When the founder is ready, they will happily break it to you. 

Otherwise, you run the risk of spending your night listening to their woes. And no one who didn’t expressly sign up for it should have to subject themselves to the trials that befall a founder on their funding journey. It would unstoic a stoic. 

Also Read: How to split founder equity without splitting up

Well, I am only kidding. 

You can ask a founder anything. Used to being asked why we are not growing at 10x speed and why we aren’t profitable, in the same breath, we can field anything and everything with ease. 

And no matter what I say here for fun, to evoke laughs, we do enjoy this wild, tempestuous roller-coaster. That is, once the head stops reeling. 

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