Reflecting on my practice – what to ask a start-up founder

Over the past year and a half, I took a series of notes on my practice. I gathered those in various documents, shuffled them around, and merged in older thoughts and reflections. Lockdown #6 was an opportunity to bring all this to shape. I am now sharing those thoughts as a series, forming a sort of mosaic on my work, and what has been driving it.

Start-ups typically fail. That’s entrepreneurship 101. Yet founders are typically deluded about the chances of their start-up failing. Worse, success may well depend in part on their delusion, their capacity to convince others, and to keep going against the odds.

When a founder presents their project, particularly when they want something from you, they will probably tread a fine line between honesty, and distortion of reality. Never believe that ‘90% done’ means what it sounds like – it’s often a polite expression for ‘we’ve kind of spoken about it once’.

I’m trusting by nature, and by choice. Working around innovation circles, I often hung out with founders – and learned some wisdom through naivety. From first and second-hand experience, I identified four areas where early stage start-ups are likely to fail, and founders to present a distorted image. I’m sharing those few notes here, in hope that they will be useful for others intending to join an emerging project.

Funding. Building a new venture requires competent people devoting long periods of concentrated time to a project. Those people will probably want some income to pay their bills – not to mention, pay for co-working space, materials, or other business expenses. Start-ups are typically money-poor, yet founders usually confident that the money will come. So, make sure you check how dependent progress is on funding, how much is in the bank right now, and how advanced discussions are with potential backers.   

Technology. Founders often have a distorted relationship to time. Present and future are not clearly distinct. Ideas are presented as complete plans; blueprints as tested prototypes. This confidence extends beyond the realm of the venture. Experimental prototypes from other companies are often identified and presented as available technology. So, whenever someone tells you they’re building a complex AI system, or whatever new piece of hardware or software – check the details of where exactly they’re at, especially if you’re not a tech person. Is there a prototype? Has it been tested? In what setting exactly? And what are the results?

Team. Start-ups attract exceptional talent, high achievers and award winners. You see those names and titles on pitch decks and investment documents. If they believe in the project, then surely, so should I? Except those names on file are likely not full-time workers, or even working at all. ‘Advisory board member’ might mean ‘pops a message once every six months‘. And all credentials are, most likely, inflated – or at least presented from the best angle. So, use the same wisdom you would on a dating app. Are those people actually in? Do they have other commitments? How accurate are their profiles? 

Culture. Start-up life promises a certain form of freedom and excitement. There is often much talk about culture, working to your strengths, and supporting a great team to do their best. This, however, is likely to clash with the founders’ narcissism, quirks, or simple human limitations. So, check in very carefully before committing. How exactly will you be valued? Will you be listened to? Will your needs actually be met? Importantly – try raising the question of power. When push comes to shove, who makes final decisions, and if there is conflict, how will it be solved?

If the founder refuses to give you details on any of those matters – take it as a warning. Yet, remember – they’re more invested than you are, and their delusion is a condition of success, so don’t be too harsh. Risky as it may be – betting on founders may still be the best option we have. Hey – did I mention I’ve been a founder myself?

Values cards project – happiness

All through 2019, following on the reflections and practice I conducted in 2017-2018 on Christian, Confucian and Buddhist virtues, I had a regular (weekly-ish) Skype conversation with my friend and ‘virtue-buddy’ Patrick Laudon in Japan, to reflect on values. We did this simple thing: each time we spoke, we pulled a card out of a ‘values card’ pack, and had an improvised conversation to try and figure what we thought of that value. I took some notes during those conversation, and am now sharing a reviewed version, which I present in dialogue form. Those are neither a full transcript nor a perfect representation of our conversation – even less should they be understood as showing distinct positions in a debate. They’re no more than loose fragments of a conversation saved from oblivion.

A: There is a song by a Belgian singer, Angele, that’s about happiness, and it says: ‘Il n’existe pas sans son contraire.’ I like that song, and I’ve been thinking, it’s probably difficult to recognise happiness, while unhapiness, that’s something you can recognise.

B: Maybe it’s that, one way to define happiness is just as an absence of suffering. So, there is no proper definition, we just look for its opposite.

A: You know the buzzword in startups, ‘chief happiness officer’. I hate it, it makes it sound like happiness is something that the company will try to sell you. Maybe you know this guy? Arnaud C**. That’s his whole platform. Pure platitude.

B: What if we tried to see it from a different angle? I like to think of happiness as a well-functioning immune system. Like a form of Nietschean ‘Great Health’, it works like a kind of armor, it’s, somewhat artificial, and protective.

A: What about this? We could say that most of the things we think about are things that will happen in the future. And they will only happen if we believe that they will. So, happiness is about our approach the world, the way we choose to encounter things. And there are different forms of approach, some more positive, some more negative. But if you somehow anchor yourself in the present, then there is a form of happiness that’s directly connected to this sense of a better future. And so, yes, maybe happiness is just something that derives from hope?

B: Maybe we can tie this with etymology. ‘Hap’ – or ‘heur’ in French – it has to do with what happens, what unfolds. And so maybe, thinking about hope, happiness is a certain way to perceive our environment as conducive to something positive, and that will naturally unfold into the future. If we think of it this way, we can make sense of injunctions, like Gide says, that it is our duty to make ourselves happy. It’s about cultivating a relationship with the world that sees the possibility of future good. And that relationship is experienced in the present as happiness.

A: So maybe, this also tells me something about cynicism and suspicion. When I reject what I would call ‘happiness in a can’, those happiness recipes and tricks and chief happiness officers, maybe that has to do with my own sophistication. I’m saying, this wouldn’t work for me, therefore it’s intrinsically wrong. Or it there is some truth to it, it would work, but only for less sophisticated people. But when I think like that, I fall into the pit of snobbism.

B: I like this image of ‘happiness in a can’. If we come back to the idea of happiness as an immune system, maybe that kind of happiness you describe is like an over-reactive immune system, and that’s dangerous, for individuals and for the collective. It’s like an allergic reaction, it can kill you. Or like drugs, it helps in the short term, but it’s harmful in the long run. Because, that kind of artificial happiness, It disconnects you from the real.

A: Or maybe it’s just that this ‘in a can’ feature, this pre-formatted message, it negates a characteristic of happiness, that it’s always experienced on a personal level, not as an abstract universal.

B: Is it then that this ‘happiness in a can’ presents happiness as a means, not an end in itself?

A: Yes, while wisdom traditions, like the Greeks, take happiness, eudemonia, as an end in itself, as a form of healthy relationship with the world.

B: But could it be that happiness is precisely the means to this healthy, fair, harmonious relationship with the world?

A: I think, happiness is a personal thing, it’s experienced individually, not collectively. It’s impossible for a collective to pursue personal goals. So, we cannot pursue happiness as a group. It doesn’t make sense.

B: Well, that would be particularly true if, as we said in the beginning, happiness is hard to define. Because if an end, or a goal, is hard to define, it is also difficult to pursue. And so, we could shift things a little and say the collective goal is to pursue the absence of unhappiness, but that’s way more depressing.

A: Doesn’t Aristotle write about happiness as a type of satisfaction that directly derives from the pursuit an activity? So maybe, we should think of happiness as an aristocratic type of virtue. That’s what you see today in startups, and all this talk about, your work should make you happy. You can get that kind of happiness if you’ve got slaves who do the dirty work. It’s probably not so easy to feel happiness from your activity when you’re a cleaner or a delivery person. And so –the practice of virtue that leads to happiness, that takes time, and it calls for certain conditions. So, there’s something dangerous about this discourse that says we should pursue happiness, and if we’re not feeling happy, we’re doing something wrong. I think, it’s hiding something, it’s not in touch with the real.