Should You Join a Startup?

Startups are in vogue. It seems like everybody is working on their own startup, working at a startup, looking to join a startup or at the very least, has an idea for a startup. If you’re a recent or soon to be graduate, you might be trying to decide if you should join a startup or take a job at a more established company. Unfortunately, there’s no “right” answer, so rather than give you a blanket answer, I’ll discuss the positives and negatives I’ve experienced during my time working at startups. And while I wish I could offer an apples to apples comparison to working at a larger company, I have only worked at startups and my internships were at very small companies.

It’s important to note when I refer to a startup, I’m talking about something very early stage, as in less than 50 employees, as well as a company that is looking to achieve massive growth and so will likely take on venture funding. And while I believe that companies with more than 50 employees or which are not looking to achieve massive growth or take on venture funding can still very well still be considered startups (I talked about it here), for the purposes of this post that is what I’ll be focusing on, as those are the types of companies I have experience working at.

The Good

Since joining CoachUp, I’ve worn many hats; I’ve worked on marketing, business development, product and customer support. This was hugely beneficial for me as a recent graduate, since, like a lot of people, I didn’t know what type of job I would enjoy or excel at. When I first joined CoachUp it was in a business development/sales capacity, but overtime it became obvious that I was better suited for a marketing and product role. Had I joined a larger company as an inside sales rep or business development associate, it would’ve been a more difficult path toward figuring out I was in the wrong role. I would’ve likely spent a year realizing BD/sales wasn’t for me, and then I would’ve wanted to try product or marketing, but I still wouldn’t have known for sure if that was the right role for me due to lack of exposure. So if I were lucky, I would’ve been given the opportunity to switch positions within the company, but in all likelihood I would’ve had to find a new job. However, at CoachUp, we realized there wasn’t as much need for someone fully dedicated to BD as we originally thought, so I began helping with marketing and product. It quickly became clear I could provide more value there, and so we quickly transitioned me to the marketing department full time. The transition was seamless, because I didn’t have to build rapport or trust at a new company with a new team.

Another huge benefit of wearing many hats is that you get to learn about all different aspects of building a business. Not only is it great that I got to figure out that I enjoy working in marketing and product, but I also got to learn about BD/sales and customer support. The one team I haven’t been a part of is our engineering team, but in the early days when we were smaller we all sat together (now that we’ve grown we sit by department) and so I was able to ask them a ton of questions about the technical aspects of our product and given my role, I still collaborate with them on a daily basis. This has helped me learn a ton more about building an application from scratch and managing an engineering team. I’ve even got to make some simple commits to our repo! This kind of exposure to every facet of a business is not possible at larger companies. You’re much more siloed, which prevents you from learning about other aspects of the business, unless you really go out of your way to do so. At a startup you’ll learn a ton just through osmosis, plus you can learn even more by picking you coworkers brains whenever possible.

The intimate work setting of a startup means that there is a huge amount of transparency into the business. You know everything that is going on because you see it firsthand. It’s also become fairly standard practice at startups to share key business metrics amongst the company so that everyone is aware of how the business is doing as a whole. We send out company-wide updates from the marketing, engineering and customer support teams so that everyone is aware of the happenings of every department. We also have an admin dashboard that shows real time stats for all of our important KPIs, which anyone in the company can access. This was a huge reason why I wanted to join an early stage startup – I wanted to see and be a part of building a company from the ground up, so that I can take those learnings and apply them to my own company one day.

Having the work I was doing on a day-to-day basis actually contribute to the company’s growth was something hugely important for me. Coming from playing sports my entire life, I was used to and enjoyed being a key contributor to my team. The idea of going to a large company where I wouldn’t be able to see how my work was helping the company was not very appealing. The exact opposite is true at startups. You’re going to be given a lot of responsibility and you’ll be able to see very clearly how the work you’re doing is helping move the company forward.

The other things people often cite as benefits of working at a startup are: no dress code, social activities with your co-workers, great perks (stocked kitchen, paid meals, kegerators, etc.), cool offices — just to name a few of the “superficial” perks you often hear about. Unfortunately, early stage startups won’t have those crazy perks or amazing offices you hear about, because they can’t afford them. In fact it’s a giant red flag in my mind if an early stage company has incredible digs or crazy employee perks — they should be spending that money on building their business! And while I’m obviously being a bit of a snob calling them “superficial” perks, I like kegerators as much as the next guy, I just don’t think they’re nearly as important as the other reasons I gave earlier. I also think that in general many workplace environments are moving in the “startup vibe” direction, so joining an early stage startup is not a requisite for finding a company that can offer those types of benefits/perks.

The Bad

A lot of the positives about working at a startup are unfortunately also the negatives — I know weird. By wearing many hats you learn about a lot of different aspects of a building a business, but you don’t go really deep in one area. This can sometimes make it feel like you haven’t learned much of anything at all because you’re not an expert on anything. It can also make it tricky if you want to transition into a larger company, as you’ll be expected to focus on one thing and if your skill set encompasses a little bit of a lot that can be tricky. If many of your skills don’t translate you may be forced to move laterally as opposed to upwards when taking your next job.

Similarly, it’s great to be given ownership of a project or an area of the business, but at the same time it sucks when you don’t know what you’re doing and you have nobody to ask. You’re constantly learning on the fly at a startup, and there won’t be much in the way of mentorship or learning from a seasoned veteran. Either because your company is not yet at the stage to hire someone more senior or because if you do have someone with more experience, chances are they’re too busy doing a million things themselves to really take you under their wing. Don’t get me wrong, you’ll be working with incredibly smart people and will be able to learn a lot from them, but it likely won’t be a very structured mentorship-type of relationship. This means that teaching yourself will be a huge part of your job. For the most part this is very rewarding, but it’s also challenging and when you get assigned a huge project that is unlike anything you’ve ever done before it can be very intimidating.

Priorities are constantly changing at startups; one day you might be told to put a huge project on hold you’ve been working on for sometime (and maybe really enjoy working on) because something else will benefit the business more. Because priorities are constantly changing and there is never a lull in work that needs to be done, you often have to dive in to projects without having as much time as you’d like to lay the foundation. Worse, is when you finish a project, but don’t feel you fully or perfectly executed it because of juggling too many other projects or because of pressure to move on to the next of the ever-growing backlog of to-dos. Similarly, you often won’t have as much time as you’d like to do a thorough debrief after a project to learn from the successes and failures and apply them to future projects.

If you’re joining an early stage startup, there is a good chance you’re either shaking up an existing business model / vertical or you’re operating in an entirely new one. This means there is no playbook. This is not necessarily a bad thing, as it can be fun to trek into unknown territory, but it’s not without drawbacks. You might work very hard on a project only for it to completely and utterly fail. In fact, this will likely happen a lot. You’ll often know going into a project that the likelihood of success is slim and the amount of work is high. You might launch several large, labor-intensive projects, only to have a minor task be the most successful. You have to learn to get over your failures quickly and keep pushing yourself to figure out what’s going to be scalable and repeatable.

The pay will typically be less than what you would get for a similar job at a larger company, while the responsibility and time commitment will likely be more. Not to mention every startup has a finite “runway” until you reach profitability, and if you’ve taken on venture funding you’re likely not optimizing for profitability (at least early on), so one day that runway might end and your job would just disappear. People will often cite equity as the reason why you’re sacrificing pay and job security when joining a startup, but I take issue with that. If this is your first job out of college, if you’re not technical, or if you’re not a founding team member, your option grant will likely be very small. So unless your company ends up being the next Facebook, which is highly unlikely, the best-case scenario is that your equity will amount to a sweet bonus… the worst and far more likely scenario is that it’s worth zilch, nada, zip. That’s not to say that having equity, even a small amount, isn’t an incredible feeling, because it is really cool knowing you own a piece of the company you work for. Just don’t fool yourself into thinking that your equity alone will make up for the salary cut you’re taking from working at a larger company.

The Ugly

I wish I could say that there is no ugly, but that would be disingenuous. Startups are incredibly stressful and you’ll often be given projects with short deadlines and little in the way of direction other than to “get it done.” If you’re looking for a 9-5, then startups are definitely not for you. Your work is never ending, as there is always something that needs doing and you’re constantly juggling multiple projects. Most of the time, those are good things because you’re never bored, but it can take a toll on your psyche and the dreaded “burn out” is a very real issue. Also, because there is always something that needs doing it can be difficult to separate your work and home life – leaving the office only to go home and continue working is often the rule rather than the exception.

I strongly believe that the positives outweigh the negatives, and I wouldn’t want to work in any other type of environment. That being said, I don’t preach the startup gospel as devoutly as many others… perhaps because I have no experience working a “traditional” job. At the end of the day I don’t think you can necessarily go wrong either way, so long as you do your due diligence, join a strong team and find a role where you’ll be learning a lot. It’s also hard to make a catastrophic career decision when you’re young, because there is still plenty of time to figure out what environment you enjoy most.

The last thing I want to emphasize is my belief that the two most important factors in deciding whether you should accept any job, startup or otherwise, is the quality of the team and the amount you’ll be challenged / be in a position to learn. Even if you join a large company you’re likely only be interacting with a small team on a regular basis, so make sure you do your homework on the team. This is even more important with a startup because there is no joining a new team and there is no escaping your team — your team is the company. As for finding a job where you’ll be learning something, that should be relatively easy when accepting your first job, because you don’t know shit about shit, even if you think you do. But you need to make sure you’re taking a job that’s going to push you, because you’ll learn the most when you’re outside of your comfort zone. Unfortunately, you won’t know for sure on either of these factors until you join, so do your best and trust your gut but if it turns out you made a wrong decision don’t be afraid to restart the job hunt. Ideally you want to stay at any job for at least 2 years, but in today’s day and age it’s not unusual, as it once was to move around more quickly than that at the beginning of your career.