The Dark Side of Startups

The startup scene is, in many ways, a plethora of good. The number of jobs, wealth, tools and services created by startups in the last few decades is difficult to even quantify. But as the saying goes, the brightest lights cast the darkest shadows. Let's take a moment to acknowledge, and add some contemplation to, the dark side of startups.

Creative license

Coding is a creative profession. By extension, most of the best coders i know are deeply creative people. I am the same. But the landscape of coding is changing. The value of having product managers and designers is undeniable. Little surprise there. Coders by and large lack the user empathy necessary to make a truly pleasurable product for the layman.

The problem here arises in the disparity in reality vs expectation. Many coders want and expect to be a primary contributor to the visions behind their creations. This can be a problem when you end up on a team where the engineering department behaves in a manner more akin to an assembly line than architecture firm.

The masked managers

A theory suggests everyone is promoted to the level of their own incompetence. That is to say, as you do well in your job, you are promoted. You get a new title and start performing well in the new role. Repeat. This trend continues until such time that you are no longer good enough at your job to warrant promotion. There you stay.

This is an unfortunate reality in the startup world. Young people, hungry for success, ascend the ladder of titles rapidly and at times without just cause. This places people in management positions who can be bad at management. But these people are rarely ignorant to this. Instead of admit defeat or incompetence, they often do that feels best: try to adopt some management strategy or operations. They change how they interact with people. They don a mask.

These masked managers often are transparently fake. This distances the trust they get from their employees. Perhaps worse still, this degree of dehumanizing themselves also has the effect of dehumanizing some degree of their decisions as well. In combination the two trend make for tenuous footing.

Monopoly money

Early stage startups don't have much money. What they lack in cash they make up for with impassioned promises about the future. Part of that promise often comes in the form of equity. Equity is great. It shows a commitment to an employee beyond simply hiring them. In the case where a company rockets to the financial stratosphere, your equity can be a life-changing number. The problem with equity is that your company won't be rocketing to the stratosphere.

Equity, for all its good, is often used for bad. Too many companies sell talented employees on salaries that fall far short of market rates. Part of this sale usually involves pointing to equity agreements that are rarely understood. In part because equity is a tricky subject to understand. Concepts like dilution, preferred shares and vetting cliffs are unintuitive and can leave all but the most studied employee agreeing to terms they don't actually understand.

Hours and appreciation

Every company i've been involved with has a cohort of employees who care more than they arguably should. This excessive caring, often expressed in an above-average sense of responsibility, is an invaluable asset to the companies that benefit from it. But these employees rarely go as appreciated as they should. Conversely, when growth slows and numbers lag, executives will seek to incite urgency in the ranks.

Employees with greater senses of responsibility will take these incites more to heart than the rest of your company. Without managers stepping in or preempting these responses, the most dedicated employees with a company may burn out or feel woefully unappreciated. Or both.

Pick your poison

As i said at the onset of this article, i'm a firm believer that startups bring a ton of good into the world. Which again is not to say that they are perfect. When you are joining a startup, especially if you are new to the scene, you should be cognizant of the risks they bring.

That said, every company experiences these problems in different ways. They may have great solutions for some but suffer badly on others. Luckily for engineers, talented candidates have their pick of the litter when applying to startups, if you can suffer the traditionally awful interview processes. But it is better to be patient and find the right culture and team than to rush into a job you grow to dislike.

tl;dr: Startups have a lot of good but also some bad. These are the things to look out for.

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Written by Ben
Ben is the co-founder of Skyward. He has spent the last 10 years building products and working with startups.