Taking The Bus

Startups are awesome.

You’ve heard that one many times before.

They are awesome because there are things like free beer and snacks, and you can wear shorts and sneakers to work every day if you want (!) and you even have like, a whole half of a percentage point of equity in the company, which pretty much means you’ll be rich in a few years if you just work hard.

But here’s the reality: startups are a grind.

Now, you’ve probably heard that one too, but here’s what that grind actually means.

It means really getting to know your co-workers (co-workers is probably the wrong term?—?family or roommates are a little more accurate). You’ll all be sharing the same conference room (say goodbye to any private phone calls), sharing the the same hotel or Airbnb when you travel for that big conference, and (holds nose) sharing the same bathroom everyday.

It means that you’re going to argue with those co-workers. No, not discuss. Argue. It will happen, and it’s healthy. When you’re at an early stage company, you can’t hide behind passive aggressive emails or Slack messages. You’re all working within a few feet of each other, and when something comes up, that usually means that person will take out their headphones, roll their chair over to you, and just like that you’re forced to have a conversation to resolve whatever conflict you were Slacking or emailing about (“God dammit that button needs to be FOREST green not AVOCADO green! How many times do we need to talk about this!” You get the point…)

It means taking the bus from Boston to New York and each sleeping on a friend’s couch in order to close a deal with a new customer (Hey that’s $40 for a round-trip Bolt Bus ticket for $1200 in new MRR, I’ll take it). Oh and you told that customer that you just happened to be in New York and could “swing by” any time after 10 AM tomorrow because you happened to already be in town. In reality, you had a good feeling they’d sign if you could get in front of them tomorrow and did everything possible (for as cheap as possible) to get to New York.

It means that at some point, something is going to break, and someone who is paying you money?—?like real, monetary money?—?is going to be really, really pissed. And because you’re at a startup, it’s not like there’s some bucket of customer complaint emails that a trained support rep handles and escalates. It means they have your cell phone number (you don’t have a desk phone) and they’re going to call you before you’ve even had your morning coffee on your way to work and let you know that your software just accidentally triggered the wrong email to 10,000 of their customers (not your customers) who are now showing up at all of their stores. Oh and having them churn is not an option, because they’re the golden customer?—?they’re on your website, they’re your go-to case study, and you’ve had investors and prospective employees talk to them about just how great your product is.

It means that you’re going to have to get good at faking it until you make it. There’s going to be some feature of your product that looks like some magic software to the end-user, but is actually just a button that submits something to a Google Doc. There’s going to be a whole lot of “we aren’t sure how well this will work until they’re actually onboard as a customer.”

The real reason to join a startup shouldn’t be because of the things like free beer, snacks (those are perks, btw, not culture) and the glory of telling someone “Oh me? Ha. I work at a startup. It’s pretty sweet.”

Join a startup because you’re passionate about the problem that the team is trying to solve.

Join a startup because you can learn, and the best way to learn is by doing.

Join a startup because you love all of the messy stuff listed above (bathrooms not included).

Just make sure you’re ready to take the bus before you join a startup.