The Dark Side of Tech Jobs

Free massages. Unlimited sushi. Ballpits.

Tech is a glittering candyland of pure occupational pleasure, right?

Sure… except when it isn’t.

While there are plenty of great things about tech jobs, it’s important to remember that tech companies are still like any other organizations - i.e. they’re run by humans with all the typical human frailties.

So before you take the plunge, I recommend checking out a couple of recent books that examine the dark side of tech.

Disrupted: My Misadventure in the Start-Up Bubble

Dan Lyons covered the original tech boom in the 1990s for Newsweek. So when he got a chance to hop on the gravy train the second time around, he went to work for Hubspot - the hottest startup in Boston.

What Lyons saw there serves as a warning sign for anyone thinking about going to work for the next .com darling:

Vast age imbalances

Despite having three decades of journalistic experience, Lyons’s boss was a 25-year old and his co-workers were more motivated by free candy and Nerf wars than a desire for work-life balance. While these weren’t deal-breakers on their own, it did leave him feeling like an outsider in his own company: “Where others saw a fun place to work, I saw a place where ‘old people’ – those over 40, and certainly people over 50 – were largely unwanted, and the company made no secret of it.”

The real work of startups

While we often think of startups growing virally based on incredible innovation, the majority of startups - especially in the enterprise space - grow the old-school way: By dialing for dollars. Lyons witnessed this in action at Hubspot when he was demoted to the telemarketing department. There, he realized that a team of 100 new college grads spent their entire days cold-calling people who had filled out forms on the website, driving a huge chunk of the company’s revenue.

All that glitters isn’t gold

In the end, even though Hubspot had a successful IPO, the vast majority of the new wealth went to the company’s investors ($1 billion) and founders (over $200 million). Lyons took home $60,000 - not too shabby, but definitely not a life-changing outcome, especially after suffering through a sub-par experience.

Which all leads to the most important takeaway: Don’t pick tech companies based on hype. What you’re hearing on the outside is way less important than what it actually feels like to work on the inside. So instead of falling prey to the tech propaganda machine, do your homework: Talk to past employees, ask them explicitly why they left, and make sure you’ll love working there - not just the idea of telling your friends and family that you do!

Get the full story on life inside Hubspot

Chaos Monkeys: Obscene Fortune and Random Failure in Silicon Valley

Antonio García Martinez fled a Wall Street job during the 2008 crash to find fame and fortune in Silicon Valley’s advertising technology industry. Along the way, he worked at a startup, founded his own through Y Combinator (the most prestigious startup incubator), and went to work for Facebook before its IPO.

Throughout his crazy adventures, García Martinez has several key recommendations for aspiring techies:

Make sure you get to know the CEO of your startup

The leader of a startup has incredible power over the happiness of his/her employees since he/she controls every essential part of the organization - strategy, roles, even culture. In García Martinez’s case, the narcissistic CEO of his startup managed to drive a profitable company into the ground, scare away its employees, and even come after him with lawsuits years later. So choose carefully!

Only launch your own startup with the right amount of risk

When García Martinez’s own startup (helping small businesses advertise on Google) struggled, he realized that he was relying on too many miracles - that mom and pop business owners would embrace his technology, that he could engineer a great solution to a human problem, etc. Whereas the best startups only have to overcome a single miracle (e.g., Google coming up with a better way to rank search results, Airbnb getting people to allow strangers into their homes).

Big tech companies still have regular big company problems

Just because Apple, Facebook, and Google may be sexier than General Electric, Walmart, and Exxon Mobil doesn’t mean that they’re free from the typical bureaucratic pains those companies suffer. For instance, even though García Martinez has a killer idea to grow Facebook’s advertising business, he still needs to go through hundreds of meetings and business partners to get anything done. And even when he finally get his idea off the ground, it flops because he hasn’t done enough to win over his teammates and get the full company onboard. As García Martinez points out: Even the most brilliant techies “can be so smart about code, and yet so dense about human motivations.”

So across all these diverse experiences, the major takeaway should be to focus on what really matters. While it’s easy to glamorize working for a tech giant or starting the next one, a couple of key things usually make all the difference - e.g., who you work with and what the culture’s like. So be sure to prioritize those questions in your search over, say, “How many Michelin stars does the cafeteria chef have?” :)

Get the full story on Y Combinator and Facebook here

Bad Blood: Secrets and Lies in a Silicon Valley Startup

Wall Street Journal reporter John Carreyrou goes behind the scenes of Theranos, the startup that went from a $10 billion valuation to an SEC charge of “massive fraud” just four years later.

While Theranos may be uniquely outrageous in its deception, it’s not unique at all when it comes to its basic operating principles:

A charismatic but controlling founder

Elizabeth Holmes won over everyone from Henry Kissinger to Rupert Murdoch by pitching a vision of personalized medical assessments, all based on a single drop of blood. But because she couldn’t actually deliver on this promise, she tightly controlled any dissent, firing non-believers and even pursuing them in court afterwards.

Doing anything to close a deal

In order to make massive sales to Walgreens and Safeway, Theranos made all sorts of claims that it couldn’t possibly justify (e.g., delivering the power of a whole blood laboratory in a tiny box). And then the company’s scientists had to scramble to come up with hack-y ways of producing this, even though the results were dubious at best.

The ends justify the means

In the pursuit of this ambitious goal, the company routinely delivered test results to patients that were flat-out wrong. But this was allowed to continue because of a fervent belief that Theranos would “change the world” in the long-term - regardless of the short-term collateral damage.

Theranos is definitely the worst case scenario of a bad tech job - and certainly not the norm. But its lessons still apply to any tech jobseeker: If a founder, product, or company seems too good to be true, trust your instincts. Don’t just take the CEO’s word for it - ask to try the product and talk to clients. And then make up your own mind before you take a sip of Kool-Aid!

Get the full story on what really happened inside Theranos

In Summary

I bring up these examples not to scare you away from pursuing your dreams, but to empower you as a savvy consumer of tech organizations. Because as a prospective employee, you have unique talent, skills, and drive. And so you deserve to find an organization, culture, and colleagues that match these traits, strength for strength.

And the best way to do that is to push. Past the hype. Beyond talk of IPOs and “we’re changing the world.” And towards an organization where you can come as you are and make the incredible impact you’re capable of. Because that's the best side of tech - and that's exactly where you want to build your career.