What's it like working at a startup?

In My Humble Opinion
1

Here’s why I’m asking: I’m a software engineer. Two months ago I transferred to a new division in my company which is doing some very exciting new stuff. My new job is not development, it’s kind of a grab-bag of delivery and operations stuff, and it’s on a platform I don’t have much experience about. So not only is the product very exciting (which is the real reason I wanted to work there), but I’m also learning a lot of things that, while not unknown to people at large, are still new to me. I love learning new things and I find that intellectually the job is very exciting.

My question is about how normal the level of chaos is. I’m in a very small group and there is no hands-on manager or team lead. One of our group is a young go-getter type who wants to “make his mark”, the other one is kind of noncommunicative nerdy spacey type, and the other one is me.

Basically I feel like I’m in this Darwinian environment where we’re tasked with high level ideas like “improve I/O” on an operating system I’ve never worked with before. In my opinion the go-getter is a very smart guy but is lacking experience in organization and team communication, but he seems to be taking on a lead role (informally). Normally I have no problem with that, and I bear no grudge.

I’ve talked a bit with my manager (who works remotely) and her refrain is “this is what it’s like working in a start-up.” I’m supposed to “find places that need work” and “make my own projects” and eventually I will “find my place.” This all sounds fine. But I still feel that there’s a lack of communication.

I acknowledge that a new group is going to seem somewhat chaotic. I am able to work in a “fast-paced” environment. I am motivated. I am smart. But I am a low-ego type of person (anxiety and depression issues). I work best when I have a good mentor and I have time to delve deeply into an area and am given space to research it thoroughly and be creative.

This environment seems to me very scattered, needs focus, needs more guidance, etc.

Is my manager right when she says “this is normal for a start-up”? Sometimes I feel like asking whether she’s talking about a good startup or a bad startup; one that is eventually successful or unsuccessful; one where people thrive on the excitement or get burned out by the lack of direction.

I acknowledge I need to be more assertive, and I am trying hard to be that. So if you reply, please don’t come down on me for being shy. I am working on it. I’m mostly wondering whether this environment is as typical as my manager is depicting it.

2

This sounds like my experience in a start-up. When I joined that group they were past the phase where the original visionaries were pulling Coke-fueled all-nighters to do something they were passionate about; they’d hired executives and quarreled with most of the visionaries. What was left was a lot of confused engineers who didn’t understand that the “company” was really just an investor fraud by that point.

It was awful. Morale spiralled lower and lower, as year after year the company failed to make a profit and benefits got cut one by one. Last summer it was “bought”, which just means the investors didn’t see a complete loss, the executives got shiny new jobs, and everyone else is out of work.

3

My one experience with a true startup crashed and burned after 6 weeks. It was chaos and they blamed me for not filling the role of my job when nobody could even tell me what my job was even generally even when I pleaded.

The advise your manager gave you is frustrating but also true. Most managers I have ever had don’t spend much time with their employees even if they are on-site. In the IT world, you are usually expected to carve out your own roles and train yourself as well. It would be rare for someone to give you an actual checklist of your duties because the jobs don’t work that way and nor should you.

There is a fine line however. I have been criticized for both not taking enough initiative and taking too much sometimes by the same person in the same week. What the manager is saying is that they want you to take care of the work and yourself as much as possible but let them know generally what is going on. The only way to figure out your manager exactly is to take some on some things on your own and then send him or her a quick update about it. They will either tell you to start running more things by them first or encourage you to do more of that type of thing.

What you describe isn’t unusual though. I am a senior consultant in IT in a mega-corp so I don’t have a boss there but I do have a ‘mentor’. I am still trying to figure him out after two years. Half the time he asks me why I didn’t just take care of something and the other half, he freaks out a little after I have done something and tells me I should have run it by him first.

4

I was at a Dot Com in 1999 when it launched. I was expecting that you wanted to hear about the ping pong tables and purple walls but you are asking about management.

Wow, you guys have a manager! We didn’t get a manager until the second year of the company.

Yes, she’s right. At the Dot Com I was at, all the developers debated (argued) amongst themselves to agree upon the design and implementation. It was chaotic but also fun and stimulating. The Dot Com was one of the few that survived with several of the original people still there.

Chaos is not just restricted to start-ups. I am at a huge company now and it is very chaotic. When you have time pressure, lack of clear roles, and lack of communication, chaos ensues.

5

It sort of depends what you mean by a “startup” and what stage of growth the company is in. But, in general, “Darwinian” and “chaotic” are two common themes. “Cultlike” tends to also be a common theme as there is no rational reason to work for a start-up other than you have an irrational belief in the company or its founder.

The thing about start-ups is that you can’t take anything for granted. If you find yourself asking “how do we do this?” or “where do I find that?”, you probably won’t find an answer because “this” and “that” didn’t exist until you just thought of it a few minutes ago when you noticed you needed it.

A lot of startups to take on an air of “investor scam”. From what I’ve seen, the startup world mostly consists of Harvard MBA ex management consultant or investment banker types who find some Stamford or MIT nerds to build a website or app similar to something that’s hot right now (B2B, social networking, cloud computing, whatever). And from there it basically becomes a race to get money and create something that can be passed off as worth purchasing by Google or Microsoft. That’s why you get a lot of these serial “startup junkies” who “cofounded” all these bullshit companies that most people have never heard of.

Unless you are in the inner circle of founders/management, you are in the larger pool of jerks expected to work yourself to death pulling all nighters with nothing but Fooseball and dreams of stock options (which almost never pan out) to keep you going.

6

I worked for two startups in dotcom times. One died before the bust, the other survived! I didn’t think it would ever make any profit but it’s still going 12 years later so I guess it must have.

The main thing is, there is absolutely no procedure - or if there is, it’s just there for show and will change next week - and everything is improvised. So you need to be able to flex, and abandon stuff you were really working on and committed to when things go pear shaped. And learn new skills and be prepared to work outside your remit on a daily basis.

If you’re looking to your boss for guidance, you’re looking in the wrong place - your boss will be as clueless as you. If you have an issue and can see the solution, then just do it. Or prep the solution and show it to your boss. There is unlikely to be mentor for you - but in the end that’s good. If you have issues, IMO it’ll help you get stronger and grow anyway.

I was in marketing. But in the nature of these things, not only did I do the writing and the ‘fluffy’ web stuff, I was then required to design a functional secure extranet with zero skills - but the head of development wouldn’t give me any staff, so I had to teach myself - then I designed the UIs for web-based products, then created process flows for teams of content editors, then managed those teams, then filled in as a substitute DBA, meanwhile working with the senior management on designing new business models.

Contrary to the cynicism above, both times I was paid pretty generously and only worked 8-10 hours a day (12 during delivery). The stock options were indeed worth shit, though.

7

Keep in mind a company is only technically a “startup” while it’s trying to get it’s business off the ground. Once a company becomes profitable, it is now a going concern. In other words, at some point “this is what it’s like working at a startup” isn’t a valid excuse. It’s not a startup. It’s a shitty little company that can’t get its act together.

8

I’ve been involved in a several startups starting around the dotcom boom, after many years in more traditional work environments. Yes, we had the free lunches, launch parties, tee shirts, etc. It was fun, I won’t lie to you. The work was very intense though. In a startup you’re expected to be contributing immediately to success, which is achieving cash flow positive and then profit. Very few startups succeed – most die, a few get bought, even fewer go public. So there’s pressure to prove that your company can make it. This leads to a constant concern about revenues and continuing funding (hitting up the investors) to keep the company afloat. So, from my experience, working at a startup can be exhilarating when things are going well, but it’s like death when things turn sour.

9

Some people don’t find that stuff fun though. If I’m working 100 hours a week, I want to be compensated with more than some dorky t-shirt and free takeout. But keep in mind that they value that bullshit so if you aren’t into it, you are setting yourself up as someone who is “not a team player”.

Startups are big on “teamwork”. My former boss used to always go on about what a great “team” we were (right up until he quit to take a better job with another startup) . I don’t see anything particularly special about our team. It’s a typical tech company collection of Ivy League nerds, cute 20-something marketing girls and Indian and Asian programmers.
There’s always a question about career growth at a startup. They are usually so busy trying to get their shit off the ground that there isn’t really much time to think about how what you are doing fits in with what you actually WANT to do for a living. This continues even after the company is no longer a “startup”. Of course the founders and their inner circle are set. People who are identified as “high performers” (whatever that actually means) will have special positions created for them (usually just a title change). But what I’ve seen is that there is actually much less opportunity than in a large company. Typically even if you are kicking ass, you won’t be promoted to that new VP of Whatever job. They will hire an experienced VP of Whatever from outside the company (usually from the founders extended network).

Then again, startups often appeal to the sort of people who don’t “fit” into typical corporate cultures.