What’s it like working at a startup? My answer – it’s a roller coaster. Sometimes it’s amazing. Sometimes, it sucks.
If you think that a startup is where you want to work (or even moreso, if you think you want to found one) I hope you’re ready. Things in the business change day to day or even hour to hour that make it feel like a crazy ride. There’s really no comparison to anything from a typical full-time job that I’ve ever had. You have to be emotionally ready for a sequence of events like the following:
Monday: Big client proposal goes out, you’re pretty sure you’re going to get it. A few deals like this, and everyone’s gonna be rich!
Tuesday: 75% of installed clients experience unrelated issues. Fire drills take up the entire day. God, how can you possibly support a client like the one above?? Serious doubts.
Wednesday: Huge trial expansion with another customer – you expect usage to go up 10x that day and prove to them that you can handle a 10x expansion of usage, commitment, and contract value all the time. You know you’re ready for it. This is going to be awesome. Some members of the cs team work extremely late to make sure everything goes well.
Thursday: You check on results from yesterday’s trial rollout – usage went up 2x, not 10x. I mean, that’s still good right? It wasn’t really our fault, there were outside factors that limited usage! That is kind of disappointing – I wonder what it means for the fulltime expansion.
Friday: The client from Monday still hasn’t gotten back to you – you know the sales cycle is long, but you expected a response by now, you follow up, and continue not to hear anything. Back to the grind of trying to grab the small deals in order to keep your growth rate somewhere respectable.
Monday: The expansion trial customer from Wednesday lets you know that they were impressed with the 2x increase, and they want to go with the full rollout. Verbal commitment for a long term lock-in. This is super exciting!
4 Weeks Later: That verbal commit still hasn’t gotten written down, but it still feels promising.
This sequence is based off of one of the crazier recent weeks at Sestra, but really, it’s like this to some degree or another almost all the time. You know yourself better than anyone else does. Is this intimidating? Exciting? It’s important that you allow yourself to be motivated by the excitement – when it’s easy to keep pushing, and not disappointed too much by the downturns – when it can be really tough to push through. Lev likes to say that one of the things that has made him a successful entrepreneur is that his emotions cycle opposite to most people. When things are rolling well and everything feels like it’s going right, he relaxes a little instead of getting carried away in the excitement, and then when things take a turn the other way, it isn’t demoralizing; it’s just reason to dive in and work even harder to get things right.
This emotional roller coaster is wild enough having only experienced it on the employee side – most founders that I’ve talked to tend to shield their employees from much of the downsides, so it’s clear that for them, the ride is even crazier. Personally, I draw energy from the crazy ride, and if things are too smooth, I risk getting bored. It’s really important to be honest with yourself and talk through with your family whether this type of work lifestyle and risk is the right one for you. Working at a startup can be invigorating and rewarding, both from a career growth perspective, or financially, but those benefits are only worth it if you enjoy the wild ride.
