7 Reasons To Work At A Startup, And 1 Reason Not To

Inspired by Chip Huyen's similarly titled post, this post summarises some of my thoughts on why joining a startup might just be the best decision you could make for your career, and a word of caution for those considering doing just that.

7 Reasons To Work At A Startup, And 1 Reason Not To

This post is (as the title might suggest) inspired by Chip Huyen's '7 reasons not to join a startup and 1 reason to' post. While reading it, I was reminded of several conversations I've had over the last year or so with various people inside and outside of startups on why I think people should join a startup. Many of the topics in Chip's post came up in those discussions, though perspectives regularly differed. I also realised I hadn't taken the time to lock-in my own ideas on the topic. In other words: I was inspired to get my thoughts on the subject in order and more presentable, and this post is the result. And because I think the structure of the original post is nice, I'm (roughly) mirroring it here! Let's dive in.

Why did I join a startup?

Time for a short story to explain how I ended up at a startup. Towards the end of my PhD, I attended a conference on autonomous systems that was also attended by a small delegation of engineers from a certain fruit company. True to reputation, the group were highly secretive about what they were working on. Given the context though, I'd hazard a guess they were part of a certain 'secret project' that has been rumoured for the past several years.

After the conference one evening, I ended up getting to chatting with them and spending an evening in various pubs in the local area. One of the engineers was an experienced staff engineer, and during the course of the evening I asked this individual what advice if they were to start their career over. The answer was simple. To paraphrase:

Get a few years under your belt at a small company made up of interesting people that are trying to do something ambitious.

The reasoning for this was quite simple: in a small company, you're required to do more, and partly by extension get exposed to more of what makes a business 'tick' than you typically would in a larger business. In other words, a startup is something of a crash-course in business, and as the old adage goes: a few years at a startup may be worth twice the time or more elsewhere in terms of experience. In hindsight, while this logic made sense to me at the time, I can say that I didn't fully realise the implications of it for my own outlook on the commercial tech world and my future career. I suspect I still don't.

That said, I should be clear that this event alone wasn't the deciding factor in me pursuing 'the startup path' (I was already relatively certain a long-term stint in academia wasn't for me, for example, and I'd had a few experiences with large corporate entities that had put me off that direction a little, too) but this discussion was something that played on my mind as I finalised my PhD and planned my next steps.

With my own priorities (roughly) figured out, and this conversation in my mind, in the spring of 2018, I joined Peak, a plucky AI then-startup (now 'scale-up') headquartered in Manchester, UK. It's now almost three years later and I'm still at Peak, and have no plans on moving on just yet, and I'm glad I took the leap to join such a young company, too.

Why should you join a startup?

Now for the really big question: why do I think you should consider joining a startup? Firstly, I should be clear that I don't think startups are ideal for everyone. For one, if stability is the overriding consideration for roles, joining a startup is unlikely to be the best decision for you – after all, it's an intrinsically uncertain world you'd be entering.

Clearly, everyone's motivations and situations are different, so I can only give my perspective as someone starting out and who could tolerate the level of risk associated with joining a young company. If you're in a similar position, then here's a few of the more compelling reasons I think you should consider taking a similar step:

  • Responsibility - A characteristic of young and/or high-growth businesses is that there's simply never enough hands available for everything that needs doing. Partly as a consequence, there's a good chance you'll find yourself central to the delivery of significant technical features/capabilities pretty quickly. Speaking from personal experience, this can be a nerve-wracking (though often rewarding) situation to find yourself in. You may find yourself taking on responsibilities that may take years to acquire at larger companies. While this can be alarming at first, it can also be an amazing experience.
  • Visibility - You'll find yourself on the frontline of everything from sales calls, to customer support, to technical delivery. This will likely give you lots of face-time with all sorts of people (of every all levels of seniority), both inside and outside your business. This can be great for developing your communication skills, and for giving you insight into other businesses, too. In a larger business, there may well be several teams between you and the customer or other business divisions. In a startup, you'll get exposure to them all from the very beginning.
  • Skills - Generalists are vital to startups. This means you should expect to find yourself doing tasks that you might feel are 'not in your job description'. It's also worth noting that job descriptions are more of a notional thing in a young company, so don't get too caught up in them. On the upside, this means you'll get a taste of roles you may not have previously had exposure to. This may broaden your career horizons, and/or help you round out your skillset more completely than you may otherwise have done.
  • Perspective - Exposure to multiple business functions, as well as to the highs and lows of building a business is an opportunity to gain a more holistic view on what matters and what doesn't in the commercial world. For techies, this can sometimes be a painful process. For example, I've had situations where painstakingly designed tools and services have barely seen any use at all, while other tools and services that were put together almost as an afterthought see prolific use across the business. These experiences can be a great way to learn how to not take things personally, and to see your work as part of the bigger picture. Developing a more mature perspective on these things is also a great way of helping you prioritise work that will be most likely to be useful in the longer run. Which leads me to...
  • Impact - You will change things. Young/high-growth business are a continuous process of discovery. No-one really knows the optimal way of doing anything at any given point, and the business can change significantly on a month-to-month basis. The scary – and somewhat counter-intuitive – part is that this is all quite normal and even desirable. This can be simultaneously bewildering and fascinating. The upshot is that good ideas are usually welcomed, and small suggestions can end up changing the outlook of the entire company. Knowing you've changed something – even small things – can be incredibly rewarding. Unlike bigger companies, it's sometimes easier to map your actions to specific outcomes too, which can be rewarding (just don't allow it to go to your head too much!).
  • Agency - In contrast to 'impact' for me, agency means developing a sense that you can (and should) change things in the business. This is an important distinction to draw. It is one thing to be assigned a problem, deliver a solution and see the result. It is quite another to learn to identify and formulate your own problems, figure out who and what you need to solve them, deliver solutions and to feel like this is something you should be doing and that you're capable of doing. The feeling of ownership and control that comes with this is an eye-opener. The shift in perspective can make many seemingly intractable problems suddenly seem much more soluble. For me, this might be the single most valuable perspective/skill I've begun to develop at Peak. I've heard similar stories from others at other startups, too.
  • Equity - With most startups, you'll be offered some form of equity. The upside of this is that there is a small chance that that equity could make you quite wealthy at an uncertain point in the future. However, it's not a get rich quick scheme: you will typically need to wait several years to realise any significant value for your equity, and there is a good chance you'll never realise any meaningful value at all. From this point of view, equity is best regarded as a bonus if things work out, rather than a primary motivator for joining most startups. As an aside, it also gives you first-hand experience of how equity schemes within companies run in practice, which is a subtle but potentially valuable insight in itself, and could have important implications for how you think about and approach your personal finances thereafter – at least it did for me.

Why should you not join a startup?

It goes without saying that Chip's post is a good starting point if you'd like a more comprehensive answer to this question. For me, the main reason would simply be:

  • It is a rollercoaster - ... And it can sometimes feel pretty brutal. Don't sign up to make a quick buck, or simply because it sounds cool or exciting. Be prepared to commit to a long-haul slog: there will be highs, but there will be lows, and they may well come side-by-side, which can be emotionally draining. What's more, this intensity will often come with a smaller pay-check than you (think you) may be able to get elsewhere, and will naturally occasionally involve longer and more stressful hours. It almost certainly isn't going to be a 9-to-5 job, at least some of the time. Add to that the fact that it's all inherently uncertain business-wise, to boot, and you might be able to see that the entire experience will push you.

I've been fortunate to be in a situation where I can tolerate a higher level of uncertainty at this stage of my career, and to have found a good startup (and bunch of people) in Peak. While things have been tough, I can confidently say that the process has been worth it for me personally – though whether you think it will be worth it for you is a question only you can answer.

What makes a good startup?

Before wrapping up, there's one other thing I'd like to cover off: it is implicit in the discussion above that I'm considering only 'good' startups. Dysfunctional startups are pretty much guaranteed to be a waste of your valuable time, and should be avoided wherever possible. That much is probably obvious.

But what makes a startup 'good'? How can you tell before joining? Based on my experience at Peak (which I regard as being in this class of 'good' startups, if you hadn't guessed) and discussions with folk working at other startups, I think there's a few key criteria. From a prospective employee's perspective, these criteria include:

  • Founders - VCs naturally spend a lot of time grilling founders and when making investment decisions, some VCs place a huge amount of value on the personality and character of these individuals. This is for good reason: founders represent the DNA of the company. Everything flows from their outlook, and the ability of a company to navigate the murky waters of startup-hood is strongly tied to these individuals. For these reasons, you should adopt a similar stance when you consider investing your time in a company. Get a feel for whether you think the founder/s are likely to be capable of realising their ambitions and whether they're 'in it' for the right reasons. If at all possible, this should be face-to-face. Just be sure to have your wits about you: founding CEOs tend to be charismatic people, and this means they often manifest their very own reality-distortion fields. Make sure to reflect carefully on your conversations after-the-fact before making any final decisions.
  • Interesting people - Startups can often be an eclectic mix of people, skills and personalities. This is as likely to be a virtue as a vice. Whatever the composition, you're going to be spending a lot of time with the folks already signed up. It's important to ask yourself if you think the people already at the company offer perspectives, experience or knowledge you could learn from. Note that this isn't necessarily the same thing as people you feel you could get on with 'outside work' (though that is potentially a bonus). Try and get a feel for this too before signing yourself up – again, in person if at all possible.
  • Ambitious plans - From my point of view, a desire for rapid personal growth is probably the overriding top-level reason for joining a startup. While startups with grand plans are potentially among the riskiest of startups to join, to my knowledge (and from discussions with others) they're also the ones that are most likely to maximise this personal growth. Remember though: ambitious doesn't mean impossible, naive, or an outright scam, so think carefully about whether you think the startup's ambitions fall into the 'realistic but challenging' category, rather than the more problematic 'blue sky thinking' or 'snake-oil' camp.

Finally, I'd like to highlight the fact that good does not mean faultless. Startups have 'sharp edges': by definition they're not the 'finished article'. Most people are brand-new to their jobs, with some folks managing people for the first time. There'll likely be few established processes, and the ones that exist might be imperfect. However, the presence of some 'faults' can be yet another opportunity for personal growth: provided you don't think these faults are likely to be fatal to the business, they're actually great opportunities to suggest (and execute!) improvements and further your impact on the business. At very least, they're a good learning experience.

Closing thoughts

I feel as though I've grown a lot in the last few years. I've also become aware of how much I've yet to learn and grow, too. There have been some points where I have questioned my rationale for joining a startup. It has been a rollercoaster, and the rollercoaster is far from over for Peak: I'm sure there are going to be many more highs and lows to come as we continue to grow at a breakneck pace. However, if I had to choose to do it again, I would. And I have no plans to get off the startup train just yet.

One more thing...

The startup world is a strange place. The 'Cult of the Startup' is a real thing, and it can be deeply unhealthy if it reaches obsessive/compulsive levels. If you choose the 'startup' career path for yourself, make sure that you take care of yourself: be clear on your priorities, and know your limits. If your work is always gruelling, it almost certainly isn't worth your time. Remember to take a break. And remember that there are more important things in life that deserve your attention, too.