The bootstrap grind: should you do it?

The second .com boom has created many a self-made billionaire. A substantial number of said billionaires come from entirely unremarkable academic and professional backgrounds (case in point: WhatsApp’s Brian Acton). This has inspired an entire generation of people, mostly Gen Y and millennials, to forge their own rags-to-riches stories.

That’s one of the best things that has happened to humanity in the last century, but also one of the worst: for every Mark Zuckerberg, the unvarnished truth is that there are at least a hundred John Does languishing in the pits of startup hell, who will never see a single cent materialise from their misguided efforts at creating the next big thing.

Fortunately or unfortunately, I’m a part of the same tech-crazed generation of dreamers. I gave up a lucrative career at a Magic Circle law firm to teach myself programming, and despite being completely cognisant of my very apparent limitations, still harbour the hope of one day having my own personal fiefdom in the kingdom of technology.

As a result, apart from a short year after my graduation, I’ve spent most of my (admittedly short) working life in and around a variety of startups. In that time, I was briefly involved in two pre-seed start ups in very different industries. At the same time, I’d also spent a year at a well-funded start up, and now work as a web engineer at Tech in Asia.

As a direct consequence of these varied experiences, I’ve also come to form a set of strong opinions about when and whether you should join and/or bootstrap a start up.

Your startup will probably fail

If you spend any significant amount of time with would-be founders, you’ll most likely very rapidly discover that the word “failure” is extremely taboo in such circles, and rightly so.

The startup grind is punishing, and requires unyielding self-belief of those who dare tread where dragons lie.

The fact is, the startup grind is punishing, and requires unyielding self-belief of those who dare tread where dragons lie. But more often than not, the very motivation that drives most founders to start their own companies amounts to nothing more than delusions of grandeur.

Therefore, the first thing any would-be founder, co-founder, or early employee needs to square with is the reality of imminent failure constantly looming on the horizon. It’s often said that failure is the best teacher, and it is. But like most good teachers, it is also utterly terrifying. If you haven’t got the stomach for it, you should probably step away before the incessant fear that all your hard work will very soon come to naught consumes your soul.

You are probably not good enough

Following on, if you’ve decided that the prospect of crushing defeat is something you can stomach, the next question every founder faces is this: “Can I actually do this?” The answer is no, you probably cannot. Men are not made equal, as much as the politically correct horde of neo-liberal millennial would like to convince you otherwise.

Leading is extremely difficult. A leader has to be a walking contradiction. He has to be empathetic to a fault, while at other times, must make merciless decisions on his quest to find the rumoured unicorn. He must both be transparent and a consummate poker player. The list carries on ad naseum. That’s a tough tight rope walk, and one that most don’t get very far in.

As such, it is imperative that you question yourself, and/or your co-founders, if you have any. If you’re an early employee, do you know your founder well enough? Do you, in your heart of hearts, believe with everything you have, that you, your co-founders, or your founder(s) respectively have the iron in them? If not, you should quit, right now, because if any of these key people fall short, your company will invariably blow up in spectacular fashion.

Show me the money

Gone are the days where a group of university students holed up in a hall somewhere on campus could bootstrap the next multi-billion-dollar tech giant.

In the trenches

Life is still good