Working at a startup is a nightmare

- May 20, 2014 14 MIN READ

Disclosure: This article may get me fired. 

It’s a truism to say that starting a business is hard.

We often hear about the struggles founders face – the tumultuous journey from conception to development, right through to commercialisation.

But little do we hear about the employees who ALSO put their blood, sweat and tears into what is essentially somebody else’s dream.

Running a startup is hard, but so is working in one.

A serendipitous meeting

Founder of Shoe String Media Group, Mathew Beeche and I met at Vivo Cafe. Mentally, I was prepared to ‘sell’ myself as an employee – to persuade Mat of the value I would bring to his company.

As it turned out, I spoke very little. Instead, Mat sold his dream to me – and it was the first time I got to experience his expert sales skills. (Seriously, it’s mind-blowing.)

After the meeting, I was buzzing, excited to be a part of something so precious to someone. Mat has gone so far as to describe Shoe String as an ‘extension’ of his being; and I’m sure this romantic notion resonates with many founders.

To be welcomed in as the first employee, therefore, was certainly an honour – akin to a newfound mother trusting someone to cradle her baby for the first time.

At the time, I didn’t know I was walking into a ‘startup’. Even if I did, it wouldn’t matter, because I didn’t know what that meant.

I’d argue that people who choose to work in a startup environment are drawn by the novelty, the excitement, the vision. Passing up an opportunity to be a part of ‘the potential next big thing’ is surely riskier than accepting a heavy workload, right? Some opportunities come once in a lifetime. Or so it would seem.

But it wasn’t long until reality kicked in.

At first, the workload was a shock to my system. I was balancing full-time study, an unpaid internship and a paid job. But I enjoyed the challenge, because I was delivering more than what I assumed I was capable of. I was realising my full potential.

I’d compare that excitement to the first time I did a decent backflip and cartwheel in dance class.

More importantly though, I was learning what it takes to run a media startup. Should I decide to start my own media empire in the future, I would be at a distinct advantage.

At the same time, this knowledge is a curse. The amount of work it really takes to not only drive a startup to the stage of profitability, but to even keep it afloat, is definitely underestimated.

It’s fucking hard, and it’s not even my business.

In the early days, I felt there was no choice but to prioritise Shoe String over university, interpersonal relationships, leisure activities, and basically everything else. The result was: I almost failed uni, many friendships met their untimely demise, my personal life became non-existent, my mood deteriorated and my sanity almost escaped me entirely.

This is why I was a little shocked when I read about Peter Williams’ comment about “Australian startups’ struggles [being] greatly exaggerated” – and even “bullshit” – on StartupSmart. Williams, who is the CEO at the Centre for the Edge at Deloitte Australia, probably came off harsh in the report – because words on a screen can’t entirely convey a speaker’s intended meaning – but the comment still felt dismissive.

It’s like telling someone who is on the brink of burnout, ‘look, it’s hard, but not that hard. Other people have it worse, so harden the fuck up.’ It’s invalidating what is essentially subjective. You can’t tell a pain recipient that their pain is not that painful.

As such, I am fully cognisant of the fact that founders put in a lot of effort to drive their startup to success. I’ve seen Mat in action. He has overcome challenges that many of us aren’t even willing to face.

My point, however, is that startup employees also put in effort – but they don’t necessarily receive the same rewards or recognition. Startup employees – at least most of them – know that they’ve been assigned an important role and want to respect the privilege.

Pratibha Rai, one of Shoe String’s Top Mentors for Sydney, has spent seven years working across  multiple startups. When speaking to her, it’s obvious that she has a love/hate relationship with startups. Those seven years, she admitted, were “the best years of [her] life”.

“I would not be where I am had I not gone the startup route,” she added.

But Rai is also, admittedly, ‘cynical’ about her experience. She chuckled as she suggested, “it’s probably an understatement to say working in a startup is exhausting.”

“When you start working, you’re all in. You know what’s expected of you. Then three to six months later, you realise that all you’re doing is work. You go to the office to work, you come back home. You might have dinner, and you’re back to work,” Rai said.

“You’re answering emails on the weekend. When I was a community manager, and I got a support email, I’d get onto it straight away. But when I got a coworker email, that would [annoy] me. There’s this level of rudeness. The attitude is ‘there’s so much to be done, and we all have to do it right now’.

“You work your life away and then have zero job security at the end.”

In a previous article about late-stage capital raising in Australia, I make a point at the beginning about the ‘sense of immediacy’ that’s infiltrated our culture – a demand for instant results.

Founders can get consumed by this sense of haste and lose sight of how their employees are coping with the pressure – the amount of hours they are working, the sacrifices they are also making. Sometimes they push too hard because they want to fast track growth.

Rai said both humorously and poignantly, “There’s a lovely little myth we have in the startup community – that the founder is everything … startup founders like to say, ‘we work 16 hours, we sacrifice our family’. Well excuse me, but your employees are doing exactly the same thing, and getting zero recognition!”

Shoe String has been tested me in ways I’ve never been before. And it’s been worth it. My biggest transformation as a writer and overall professional happened here, and I couldn’t be more proud to be a part of this company that’s made me better.

But if I knew exactly how challenging it would be, I wouldn’t have chosen this career path for myself. That’s not to say I regret it – but I would have been like most other people and avoided pain.

Truth be told, in the early days there have been times I regretted taking the job – I thought I wasn’t good enough for such a demanding role. But I felt guilty about changing my mind, so I stuck it out one day at a time. My passion has since fluctuated. Some days I love it. Some days I hate it. But this isn’t all that uncommon among people who have any kind of job.

Rai said working at a startup “kills your passion”.

“At one point, I went ‘why am I doing this?’ And here’s the crux of it: all startups want to hire someone with passion. But all startups do is kill that passion,” she admitted.

This comment may strike a nerve. But another startup employee that I spoke to expressed the same sentiment. He was willing to be quoted, but not named, because he doesn’t have the same relationship with his employer that I do with Mat.

His words were: “Working at a startup is like an exhilarating nightmare. It’s like a video game world. You’re in this dark world fighting villains, and you love the game when you’re winning and hate it when you’re losing.”

Can’t stop. Won’t stop. 

I wouldn’t personally compare a startup to a video game simply because I don’t recall ever playing one, but I do agree with this employee’s ‘addiction’ analogy.

He said, “You want to stop, but you can’t stop. You want to leave, but you can’t leave.”

“There is so much uncertainty that it always feels like things are going to hit the next level very soon. Soon isn’t soon. It takes a long time. You’re just waiting and waiting, thinking ‘soon’. Before you know it, years go by and you haven’t moved as fast as you thought you would.”

Rai goes so far as to say that many employees come to the conclusion that they’ve “wasted” their life.

“I’ve spoken to a lot of startuppers who have come to the conclusion years later that, ‘holy hell, I just wasted my life’. When you’re young, you don’t understand that the hours you put in comes out of the total hours of your life,” she said.

“A lot of startup employees are young, they’ve just come out of uni. When you get into a company and you see everyone doing 16 to 20 hours a day, you think ‘oh I should be doing that as well’.”

Numerous times, I’ve thought about being a small fish in a big pond. But I would never feel the same satisfaction as I do here. I would be bored.

That’s not to say working at a startup doesn’t involve boring tasks, but overall it’s so chaotic that boredom ranks fairly low in your list of feelings. Murderous would come before boredom.

Disconnect: Founders and Employees

The biggest problem, based on my experiences and those of other employees who are currently working or have previously worked in a startup environment, is the disconnect between founders and their employees.

There have been times when I felt that I was losing my mind. The workload was a great distraction for a while – as I was dealing with personal loss – but keeping that up drained the life out of me. Everyday, I would stop working not when daily tasks were complete, but when I was exhausted and incapable of putting together another sentence. In a startup, nothing is ever really complete – well, not until that billion dollar acquisition, which appears to be the ultimate goal for many founders.

I had to address my concerns with Mat – which wasn’t difficult because we have a very open and transparent relationship that I’m grateful for. I told him I was drained of energy and unproductive. Everything started taking quadruple the time it previously took. I began to question my abilities – even wondering whether there’s been some sort of brain damage from when I accidentally banged my head against the inconveniently-located wall. I was incredibly disappointed with myself. I started losing my passion for writing. And above all else, I just wanted to escape.

Before going ahead, I admit, I’m an intermittent complainer. Every hour or so, I’m like ‘what the hell is this…’, ‘why on earth…’, etc. I think this comes down to my extroverted personality. Mat, on the other hand, hates complainers – don’t we all? It’s not that he hates complaints, he just prefers people who offer a solution to the problem. This is fair. I realise now that positive changes will only take place if employees present a solution to the problem – rather than just voice their issues, treating their employers as psychotherapists.

Rai communicated a similar sentiment, saying that, “the cool thing about startups is they’re usually small enough to respond to change. Everyone feels the same thing; it takes one person to say it and it helps everyone in the company.”

When I’d speak to Mat about an issue, I would often say “I can’t do this. This is too much.” I wouldn’t offer a solution – hoping Mat would. In response, he sometimes came across as dismissive to my concerns – especially when he’d say, “Can’t is not an option. You need to have a ‘can do’ attitude”. I appreciate the intention behind this entrepreneurial cliche, but just because someone else can lift a tonne of weight, doesn’t mean I can – at least not without years of training. Some things are unattainable, in my opinion.

“I understand that it may come across as me expecting the unattainable. Whilst I may see hustling and pushing people to get things done as a strength, I do realise upon reflection that this can also be a major weakness in my management style that I need to work on … I’m not naive to the fact that I’m also young and not 100 percent competent in every area of business,” Mat said to me in an interview that I conducted with as much a straight face as I could. (Yes, I interviewed my boss.)

“I believe in setting stretch goals because if you’re not continually striving for something outside your comfort zone, then you will never attain excellence and never realise what your full potential is.”

But not every employee will appreciate goals that are so far outside their comfort zone. The anonymous employee I spoke of earlier said “unrealistic goals worsens the stress”.

I feel that a better approach is to set employees small ‘step goals’. For instance, as an online publication that depends heavily on advertising revenue, pageviews are important. Rather than doubling the traffic goal every month, I would prefer a 30 percent increase – or even weekly average traffic goals, rising at 10 percent week after week. Goals like these are outside our comfort zone, but also realistic.

Accomplishing goals provides a sense of achievement, which in turn motivates employees to continue hitting milestones. Stretch goals can be so far off that the employee feels like a failure; they can end up feeling discouraged altogether.

“I don’t believe I set unreasonable goals. I push my employees to be the best that they can be. I have a 10 year history in managing various size teams and I’ve had high expectations of those people. I know that I have applied a great deal of my sales management skills and crossed it over into a task management environment which is not all that common in the media industry,” Mat said.

“But if I wanted to be like everybody else in the media industry, I may as well pack it all in now because if I don’t drive myself and my team to scale high fences and break down brick walls, we will never reach the goal of becoming the number one business and political publication for Gen Y in Australia. That doesn’t mean, however, that I don’t take on board feedback that I’m given. In fact, I encourage and insist on it because without it we can’t create a system within the business that caters to everyone’s needs.”

This is true. I’m lucky that Mat is open to feedback, and can handle my uninvited critique. I realise upon reflection that I make things worse for myself by being a perfectionist. This comes down to my personality. I always feel the need to do right by Mat. I feel I have a responsibility to help him achieve his dream and I don’t want to disappoint him.

I’m not the only startup employee who feels this way. Startup employees tend to take a lot more responsibility for their work.

Rai said, “the people who tend to get hired by startups are usually self-directed and entrepreneurial.”

I wouldn’t consider myself ‘entrepreneurial’ because it sounds very snobby coming from an employee, but I do like the independence to make my own choices. I appreciate the autonomy Mat gives to write whatever I want – a rarity in the current media landscape.

It’s true that entrepreneurs like to hire entrepreneurial employees – or intrapreneurs.

Mat admitted it himself: “One thing I have noticed is in my recruitment style. I tend to gear towards hiring entrepreneurial and intrapreneurial people, because those types of personalities take ownership of new projects, new ventures, and the duties they’ve been assigned. And in the same way I obsess about my business, they start to do so as well – and that is of great benefit to me especially in the early stages.”

Being a perfectionist, then, can be beneficial. You may however get a little too obsessed, which ends up slowing you down and driving you mad.

Going back to the disconnect between founders and employees, I feel that at times my work outside work hours were overlooked.

It’s a fact that businesses are moving away from a time-centric payment paradigm and towards a value-centric one – meaning that how many hours we work or how hard we try will matter less and less. In the future, it’ll be about the value of the work we’re creating, not how long it took us to do it. At first, this may seem like an advantage, because if you can hit goals by working three hours a day, then that leaves plenty of time to enjoy life.

But there is a disadvantage to this – because on the flipside, if someone is assigned a task which is unattainable within a healthy timeframe, people would be working overtime without being financially compensated.

Rai believes some founders simply don’t care about how many hours their employees are working, and others are just blind to it.

“They don’t realise what their employees are doing and what the effects are,” she said.

Mat admitted he’s a strong supporter, and even advocate for work/life balance.

“But when it comes to me personally, I find it’s an area I struggle with because one blends into another frequently. I think that when you find something you love and you’re passionate about, it’s hard to distinguish what work actually is. Sometimes I don’t realise this is work for my employees,” he said.

“However, I am very conscious of their wok versus their life outside the company. And I don’t ever expect anybody to be working on things outside of normal business hours, unless an arrangement has been made.”

This is where there is a disconnect. Mat has always been ‘outcomes-focused’, which can be easily interpreted as ‘this needs to be done now, whether it takes you 10 minutes or 10 hours’. Most of the time, it’s the latter.

Ultimately, everyone in a startup is learning their role. Although there are times when I stubbornly want change, and Mat stubbornly wants certain systems to stay in place, or the other way around, one thing I believe differentiates Mat is his willingness to reflect and take issues into consideration.

“The downside of being the first employee in a startup is that you’re also the guinea pig. As a founder, I’m testing the boundaries. However, it must be noted that in terms of you being the first employee, the relationship I have with you is a unique relationship. Based on my personal experience and those of other founders I know, there are similar traits in the relationship between a solo founder and their first employee to that of co-founders in a business,” Mat told me.

“The intimacy. The amount of time spent together. The ups and downs, The making and execution of decisions together that determine the direction of the business. These are similar to co-founders. You’re in this weird cocoon that you don’t experience in a corporate environment.”

What’s the solution? I think employees need to open up about their issues – without fear of adverse reactions – and founders need to be more ‘in tune’ with their employees. Talk to them, compliment their work, and for goodness sakes give them a break!

Rai suggests, “founders need to realise that people are their biggest resource. It’s what they’re spending the most money on. If you treat people like slaves, you will get slave level of work – which is ‘I’m just going to do what I need to do and get by’.”

“For employees, the frustration is not only about the amount of work that has to be done, it’s about lack of appreciation. Founders shouldn’t ask questions when employees come in late at 11am because they’ve been working ‘til 3am the night before. Instead, they should be grateful.”

Steve Wozniak, Co-Founder of Apple, once pointed out in a media release that we don’t hear ALL the voices of people behind startups – “all the people working within them, the quiet coders, and the developers who are often overlooked time and time again.”

“It’s important that the truth be told; who does all the work to pull the idea and thought into the new computer, the new software platform or just the new way of doing things. These people often have almost super human concentration and focus and play with hundreds of obscure engineering and programming sequences in their heads. We want to know them and we want to recognise them.”

Happiness and balance maximises productivity. It may seem like a slower route to success, but surely it’s worth the wait?

“I don’t want employees that just churn over. I want long-term employees, a tightly-packed team, which means everyone needs to be happy. I am open to building a company with my employees to achieve that,” Mat said.

While many startup founders lament the lack of talent in Australia that are willing to leave their cushy corporate jobs and embark on a stressful and unpredictable startup journey, can you really blame them? Those who reject the idea of working in a startup, know that it’s going be one hell of a challenge.

This doesn’t necessarily mean people are lazy – just that they don’t want to put themselves in a position where they don’t have a work/life balance or job security. The other side of the story is that many Gen-Yers study hard at university, so they don’t have to work hard after graduating.

Our parents have conned us into believing that studying hard for a few years will lead to a comfortable career thereafter. As soon as we start looking for a job in this unstable employment environment, we realise that what our parents really wanted was to establish status. And now we’re left figuring out how to earn a living with all the wonderful yet unwanted skills and lack of practical experience we have.

I agree with Rai when she says joining a startup is a much better way of gaining experience than working in a corporate environment. At the same time, however, founders need to carefully consider whether they’re exploiting their interns and employees.

“The good thing about startups is that they will also take you in even if you have no industry experience – even if you’re fresh out of uni. But they’re really going to use you. They don’t necessarily do it with bad intentions; it’s just how it happens,” Rai said.

“I still recommend startups to noobs who want to get anywhere in the industry. It’s the best way to learn, because it’s hands-on experience.”

So would employees want to work at a startup ever again? Ironically, Mat said he would never work for a startup.

“I like founding a startup, being part of something innovative. I don’t think I could work for someone else’s startup. I know that I excel working as an employee in a corporation, not as an employee in a new business,” he said.

“I was always an entrepreneurial employee. When I worked in a corporate environment, I treated my department as my own business. I’m good at building on top of things that have been established. Take Mark Harbottle from 99designs, for instance. He builds businesses until the $2 million mark, then brings in a CEO. He knows his strength is early stage. My strength is growing a stable business, which is why it’s been such a struggle to date.”

Despite all the frustrations I’ve communicated, I would definitely work at a startup again, but one that operates in a different industry. Working at a startup is a better way to learn about an industry than a university degree.

Rai said she would also consider working at a startup again, but would be much more cautious about who she is working with.

“I would almost lay down the law in terms of what I will and will not do because things can get out of hand really quickly,” Rai said.

Working at a startup is a nightmare at times … but one worth living.

Featured Image: Cartoon created exclusively for Shoe String.