Lessons I Have Learned in Startup Land

- - posted in lifetech

I dunno if y'all knew this about me, but I’ve worked at a lot of startups. Pretty much every kind of startup. Some of them seem silly now. Some of them, when I remember them, they tug at my heartstrings a little as I contemplate what could of been, or what was. Some of the companies had no future when I left them; some of them went on to live out the rest of their startup life cycle. A couple have gotten sold, while a couple got sold down the river. Here are just some things that I learned along the way. They might apply to you, they might not. It’s okay if they don’t. I don’t mind.

Lesson 1: Every startup is a carnival ride, in a bad way

I can almost hear the groaning from here. “Of course it’s a carnival ride!” I can hear you say. It’s okay. Then there are some of y'all who are probably nodding along, because you know I wasn’t talking about the ups and the downs and the excitement and the thrill of the ride. I’m talking about the unshaved drunk grizzled harbinger of your ultimate doom who’s working the controls.

As you roll up and queue for the ride, you see him there in the corner, right next to the plywood standee that admonishes you to be sure you are THIS tall before you ride it. Next to him is an old pickle jar filled with a questionable but almost certainly flammable liquid he might just as easily drink from as use to degrease the tilt-a-whirl. That man is the CEO of that tilt-a-whirl, and before you get on the ride you should feel like you trust him at least a little bit.

Founders and entrepreneurs in general make a lot of bad decisions. That’s okay. They haven’t made enough mistakes yet to make really great decisions. Or maybe they have and they’re just having an off day. It doesn’t really matter. They’re in charge, though, so their poor decision-making will affect your work and thus your life a lot more than it would at a bigger company where there is more of a dissipative effect for decisions from up on high. If you’re at a startup, the CEO and founder is probably sitting about as far away from you as the carny who got put in charge of the tilt-a-whirl: maybe as little as a couple meters as the thing wildly spins around. You don’t have to like your CEO when you’re working at a Fortune 500 company but you should damn well like them if you’re working at a company where you are a double-digit percentage of the workforce there.

If you’re at that phase, too, you and the CEO can learn together. If your CEO is a good CEO, even if they are inexperienced, they’ll learn things from you. If your CEO is a bad CEO, they’ll make decisions by fiat that you are expected to execute and realize for them. That’s fine, if you like them and if the decisions are the best decisions, but not so great if you don’t and they’re not.

Lesson 2: The constant need for fund-raising causes incredible stupidity

Have you ever worked for a company that was on the brink of collapse? Have you ever held your breath every paycheck you cash, because it might be the first one that bounces as the entire house of cards comes tumbling tumbling down upon you? Well, if you haven’t, consider yourself lucky that you’ve only worked at successful places. Go ahead and give yourself a pat on the back for that, you jerk. Now, the rest of y'all, you should know that this is basically what working at a startup that’s in the midst of fund-raising. When a company that’s a household name passes the hat around, there are dozens of established players in the venture capital game who are more than willing to throw money at it on the likely chance that when it has an IPO they will make more money than Jesus for a few shining moments then sell off their stock to whoever looks gullible enough to purchase it. For your company, this might not be the case, and it will take a lot of discouraging groveling, ring-kissing, and bullshittery to make it happen. It will also mean your company giving up more equity than it would in later rounds of funding, which then means that the piece of that pie that might be allocated to you is smaller.

The worst thing that fund-raising does, though, is create perverse incentives, causing many CEOs to chase metrics before building a good product, a classic startup mistake.

Venture capitalists know what kinds of things indicate successful companies: rising user metrics, increasing engagement, etc. They want to look at a bunch of charts that are all shaped like hockey sticks. That’s how they know when something is a good bet. So, knowing that, guess what startups do! They pursue these metrics for their own sake, and even otherwise really smart and intelligent leaders suddenly become priests in their own cargo cult. I’ve now seen this happen with a bunch of startups, and it’s become a red flag for me. Either you have the metrics or you don’t, because the metrics aren’t the thing; the thing is having a great product that people genuinely love to use, and want to encourage their peers to use, and that drives the metrics. If your product is an unusable piece of shit, it doesn’t matter how many fucking Facebook “Like This” badges you gussy it up with; it’s still not putting butts in the seats.

Too often, I’ve seen metrics take precedence over the needs of real, actual users, and that’s a shame. The fund-raising isn’t for fund-raising’s sake; it’s to use the money to develop a great product.

Lesson 3: You will wear many hats. Some of them will not fit right.

It should surprise no one that more established companies, having a larger workforce, also have more individually specialized employees. At a tiny startup, when there are less than 10 people overall, the distinction between a product manager and a project manager might be too small for that to be two different folks. And that’s fine, because what they do is, at the 30,000 foot level, similar enough that one can serve as another in a pinch.

But what happens when your startup is running so lean that there’s just not enough people for all the roles? This is how project managers become CFOs, how CFOs become COOs, how engineers become managers, how dogs become cats, and how general mayhem commences. There comes a certain point where you have people having to fill in temporarily roles they have absolutely no clue how to perform. If those people want to learn how to do the things they’re being asked to do, that’s great! They can learn while they earn, a little, and will get progressively better with time. What happens when one of them has no interest whatsoever in the role you’ve put them in? Well, they’re going to be terrible at it, even if they genuinely want to do right by the company in whatever role they’re in.

Put another way, this is the mistake of thinking that human beings are fungible, as identical cogs. If one is missing, you can grab another one from some other part of the machine to put there. It might wobble a little, but it’ll be okay. Well, it probably won’t be okay.

People train for years to be in the role they’re in, and if they’re in a senior or lead engineering role, they have trained for years in school, then probably been out in the real world close to ten years! If your company is in desperate need of a product manager, go and get a product manager. That’s a job that people train for and have real-world experience doing, and they will be much better at it than an engineer, and assigning a new person to the role will mean not taking time away from your engineer.

If you’re running short on staff, and you need someone to occupy two roles, it’s worth asking them if they want those two roles. If they’re not interested in one of them, they’re gonna be awful at it; you’d be better off spending the time and money to get someone who’s whole life is just that one specialty, if you feel like your company has evolved to the point where that role exists there.