Letter To A Young Programmer Considering A Startup

I regularly get emails from young people, usually those with an interest in programming, who are trying to make decisions about school and/or their professional futures. This post is for those young people.

If you’re in your late teens or early twenties, you’ve grown up in a world that has come to idealize startups, their founders, and the people who go to work at them.

If you’re in school, maybe you’ve felt pressure or been incentivized to drop out and join or start a company. If you’re already out in the working world, perhaps you feel that your non-startup job is in some way inadequate, or that you’re missing out on valuable experience and potential wealth.

The generation you’ve grown up in has, for the past few years, teetered on the brink of being “lost”. Jobs are scarce, and going to university offers no assurance of landing one. Big, old corporations are no longer guaranteed safe havens in which to build a career. Startups seem, through the lens of the media, like the only sign of life in an otherwise dying landscape. I understand their appeal.

Everyone’s path is different, and your choices are your own. That said, you aren’t making your choices in a vacuum. Here are some things to consider that, in my experience, you’re less likely to hear about working in startups.

A startup is just a means to an end.

I recently interviewed a young man. I asked him where he wants to be in four years. “Running my own company,” he said without hesitation. I asked why. “Because entrepreneurship is in my blood,” he replied. There was no mention of what his hypothetical company would do, what problem it would solve for people. His goal was business for the sake of business. That’s what he had gone to school for, after all.

People are fulfilled by their work when they operate with a sense of purpose. So much of our understanding of the psychology of success is around setting goals and keeping those goals at top of mind: visualizing the moment of accomplishment, tracking our progress towards it, having others hold us accountable to reaching it. Goals give shape to our individual futures.

Maybe a startup is the best way to meet a goal, and maybe it isn’t. If the goal of the young man described above is to run a business – any business! – then perhaps a startup is indeed his best path forward. For others, though, I often wonder if they’re fitting their goals into the format of a startup because it’s an approach that’s lauded, admired, and easily understood (if not easily accomplished).

Maybe the best way to meet your goal is starting a non-profit or going into politics. Maybe it’s doing research at a university or making art in a squat. Maybe the answer is joining a large, stable company with formidable resources that you can leverage to meet your goal. Maybe your goal is best met by building a stable yet undemanding career that leaves plenty of time for family, friends, community, and self improvement.

A startup is just a means to an end. Consider the end, and don’t seek to revel in the means. What do you care about? Who do you want to help? Does a startup make meeting your goals easier or harder? Where will it leave you when your goal is met? Where will it leave you if it isn’t?

A startup job is the new office job. Startup culture is the new corporate culture.

Startups are portrayed as an exciting, risky, even subversive alternative to traditional corporate work. Startups are thought of as more free, more open and flexible. Some companies surely begin that way, but a few interviews at later-stage startups will make clear just how quickly they ossify into structures that look very much like the organizations that came before them.

As there was in the first dot com bubble, there is a current proliferation of startups, incubators, accelerators, angel/seed funding, and so forth. In order for the “startup community” to replicate itself, nanobot-like, the mechanics of “doing a startup” have been reduced to an easily transmitted sequence of actions accompanied by a shared set of values, norms, and language. As a consequence, the culture of most startups is blandly uniform, right down to a style of dress and grooming that helps “startup guys” – and all too often are they guys – stay with their herd (lest they be picked off by cougars).

Business school graduates like the young man I interviewed are going directly from college to startups, if they even finish school at all. Business majors, traditionally risk-averse, now say they don’t want to work for big companies. But startups are the new big company. They are, as I’ll describe below, the field offices of a large distributed workforce assembled by venture capitalists and their associate institutions.

There’s nothing inherently wrong with an office job. Just realize what you’re signing up for. When the company-provided keg runs dry, the free lunches are making you fat, and playing the Xbox in the break room is no longer as fun as it used to be, what then? When you find that you now report to a politicking middle manager and not the inspiring CEO who interviewed you, will you still want to be there? Is a supposedly novel working environment enough to sustain you? When everywhere you might consider working looks more or less the same, is the novelty even there?

Startups have been systematized, mythologized, culturally and socially de-risked; reduced down to formulas and recipes. Yet, there is no enduring formula for creativity and rebellion. When we attempt to factory farm innovation we breed out the very thing we’re trying raise: the creative destruction that stokes and re-stokes the fire of capitalism.

Startups are part of the system, not a rebellious wrench in the cogs.

The funding for startups – that is, the money that pays your prospective salary – comes from somewhere. Wealthy individuals and institutions invest in startups as just another asset class. The futurist Bruce Sterling recently quipped that “start-ups are full of [young] people working hard to make other people rich – Baby Boomer financiers mainly”. While that might be an overly general and cynical take it’s by no means untrue.

In broad strokes and excluding areas like biotech, venture-backed startups are a machine into which relatively small amounts of capital are inserted in one side and, ideally, quite a lot more comes out the other. (In actuality, this machine doesn’t seem to work anymore, though the effectiveness of VC as an asset class and VCs themselves is certainly up for debate). The salient point, though: what’s in the middle of the machine is you. You make it go.

The machine doesn’t care about you. In fact, the machine is designed with the understanding that most startups will fail, or at most offer unremarkable returns to investors. The majority of the companies in many VC portfolios are acknowledged duds. One or two “10x” companies prop up most portfolios. At best, startup founders who fail get another pull of the slot machine. At worst, their failures drive them to desperation.

There is nothing inherently disruptive about a venture-backed startup. The startup system is just another system; an alternative to the corporate ladder with just as many rungs to climb. Some startups may end up dramatically reshaping a market, but then so might an incumbent player or an active regulator.

The now-perennial celebration of startup-driven disruption raises the question: if we accept that disruption is even happening, are we better off in the resulting disrupted market? Have we solved a problem, or have we shifted the problem elsewhere? Have we created value while furthering justice and equality, thus yielding enduringly positive change? Or have we merely made one group of wealthy people slightly more rich at the expense of another group of wealthy people? Are we creating a better future or just scrambling up the present?

Startups have an ongoing interpersonal cost.

No story of a startup is complete without a scene or two of macho heroics: nights spent programming to exhaustion, weeks away from home trying to raise money in pitch after humiliating pitch. Startups appeal to a desire for daring that’s lost in many forms of modern work, and we’re told stories of the rewards waiting when personal lives are sacrificed on the altar of the launch schedule.

Less frequently do we hear about the damage that startups do to people’s lives. In extreme cases, as with the entrepreneur whose story of failure and suicide was linked to above, the “community” might take a day or two to reflect and mourn in blogs and tweets. Then it’s back to “grinding it out”, and more importantly, making a public show of just how hard you’re working to appease investors and intimidate competitors.

I’ve seen firsthand the damage that startups can do to relationships. I’ve watched marriages and friendships fall apart, seen children and partners pushed aside, and failed those in my life in all kinds of ways when work came to the fore. I’ve listened as people who are the very picture of startup success – visible in the press and social media, headlining conferences, forever founding and exiting – have confided their utter loneliness despite being seemingly at the social center of the entrepreneurial community.

When you’re young, relationships seem like a renewable resource. Friendships are plentiful and come easily. Just out of the house and out in the world, you’re eager to escape the heretofore-constant presence of family. Being pulled into work makes you feel important, independent, and adult. Work itself can provide a new community and new friendships, and the bonds formed during intense collaborative work are strong.

I’ve made such friends through work at early stage companies. Ironically, those relationships are easier to maintain and enjoy when I’m not working at a startup.

Parting thoughts.

I’ve worked in startups on and off for over half my life now. That work has brought me some financial freedom, and I’ve put money I’ve made back into other startups. If there is, as I argue above, a modern “startup system”, I am a part of it.

I won’t equivocate: I am deeply skeptical of this system. I’m skeptical of this system’s slavering, self-congratulatory fetishization of “disruption” while so obviously becoming the sort of stolid institution it seeks to displace. I’m skeptical of the startup community’s often short-term outlook. I’m particularly skeptical of its callous disregard for both the lives of the people who participate in it and the lives of those who live in the world that startups seek to reshape. Let’s not even begin to discuss how commonplace collusion, price fixing, and other market-corrupting activities are in the world of VC. The point being: it’s a bad game and a rigged one.

And yet. There are startups I wouldn’t want to see disappear. There are people working at and funding those startups who are good, kind, balanced in their personal and professional lives, thoughtful of the impact of their work. Just as we might cast aspersions and accusations of corruption on other systems like politics, mass media entertainment, and professional sports, we must admire those who operate ethically and efficiently within them. We should further celebrate those who are pioneering new and alternative systems, for they work in the shadow of a community that has a constant hand on the crank of the hype machine.

Now, you could say that I’m laying too much responsibility at the feet of the startup world. Though this system daily broadcasts itself as the savior of everything from capitalism to culture, surely we can accept that business is business and ideals are best left at the door. As a VC at a top-tier Sand Hill Road firm told me during a pitch several years ago when describing a conceptual feature in Simple that would let users easily and regularly donate a portion of their savings to charity, “let’s not waste time on that stuff; we’re here to make money”.

You could take this tack, but I hope that your idealism hasn’t been worn down at such a relatively young age. I hope you want your work to be imbued with meaning, purpose, and value no matter what form that work takes. More than that, I hope you want your life to be defined by more than work.

Young programmer, I urge you to consider both sides of the startup coin. There are so many ways to make a dent in the world.

A note on feedback.

If you’re part of the intended audience of this post, I’d love to hear your feedback and answer your questions, preferably over email. My address is easy to find on this site.

If you’re not part of the intended audience and are very very mad that a stranger on the Internet has a different opinion than you, I encourage you to direct your energy into an alternative argument that a young person (or, really, any person at a point of career transition) might benefit from reading. They are your future employees, coworkers, or founders. It’s them you need to convince, not me.

— May 23, 2013