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The reality of the game of life as an entrepreneur.


In my experience, life is an elevated and elaborate game of Whac-A-Mole. 

Entrepreneurship, therefore, is Whac-A-Mole on a rollercoaster — with insane twists and turns, and every mole’s on fire at the same time screaming for your attention. And yet, as I speak to more and more budding entrepreneurs, I realise that they know close to nothing of this reality. They are often thinking they will be on a consistent upward trend as soon as they control their own life, with little awareness of the real grind and total randomness involved with owning a business. 

This reality is rarely communicated as it does not make for sexy headlines. ‘Entrepreneur spends yet another day endlessly typing, taking calls, learning, f*cking up, learning more, crunching numbers, making prototypes, missing out on life events and slowly but surely building their vision’. So I am here to dive into a few of the non-sexy realities to ensure you know what you’re signing up for.

To be an entrepreneur, you have to be in a continuous problem-solving mode and, ultimately, no matter how hard you try, usually the only thing you get graded on are your sales.  One minute you are solving an employee payment issue, the next, your co-founder gets injured and can’t work for a year, and next, the train carrying $100,000 of your product has derailed. These are all realities I’ve faced. The problems range from the big to the small, and all will need your attention – so grab that mallet.

The rest of this essay may come across as a bit harsh, but, frankly, I think harsh is good –  because the realities of entrepreneurship are harsh and the consequences of poor decision making even harsher.

Avoid Desperation

From my years of meeting countless entrepreneurs at business conferences, industry shows, one-on-one meetings, and everything in between, I’ve come to learn that there are a few key indicators of an entrepreneur in trouble.  From what I have experienced, they all seem to centre around one theme.  When talking about business and why it should succeed, an entrepreneur in trouble often relates everything to their personal life and not the company’s nature. This, to me, is a vital sign of someone being overstretched and not having protected the downside.

Many times I have heard things such as ‘My business has to succeed, I spent all my savings on it’, ‘This brand has to work, or my wife might leave me, ‘I have sacrificed too much time away from my kids for this not to work out’, and so on.  They have no mention of what might make the business work, i.e. ‘My business has to succeed, the product solves a real issue’. As soon as the reason that the business must succeed is primarily personal, there are significant problems. You are no longer thinking clearly about the business. Desperation starts to set in and quickly becomes a tricky position to build a business.

But, of course, that begs the question of how do people end up in this position? Many unknown circumstances are impossible to avoid, they will crop up from time to time, and you just have to ride the wave as best you can with the best data and insights available. But, and it is a big BUT, how much of this desperation is avoidable? I would argue that a lot of it is avoidable by first understanding more about what you are getting into at the beginning of your venture and second protecting the downside.

Is this what desperation looks like?

Beware Misinformation

I have been involved in many projects, from building multi-million dollar food brands, being the original creator, director of photography and co-star of a multi-award-winning feature documentary film and being the original creator and executive producer of an adventure cooking mini-series. I have completed multiple property renovations and love doing stand up comedy, writing and producing sketches and a ton of little creative projects and helping others with theirs. These projects have allowed me to dip into different entrepreneurial worlds from food, entertainment to property – and there are a few global themes that I wish I had known when I started as, in hindsight, they would have helped me avoid some less than favourable circumstances.

Let’s start at the root. The misinformation about entrepreneurship on the internet is rife and arguably, the most dangerous thing about the game. It can trick people into a false sense of security and cause them to lose a lot. Online we mostly just see the wins, the fun team pics, the awards won, the epic after-parties and endless business mantras nice but have no real substance off camera. Before people uproot their lives and risk stability, they need to know the actual risks of entrepreneurship. Of course, none of us can truly predict the future, but a few key indicators can help mitigate risk.  Some of the most brutal regrets are based on ‘if only I had known X’. So, before you spend all of your savings and quit your job for an unproven idea, let’s chat about how to minimise the number of unknown X’s.

The only way to tackle this is to do the research, not surface-level research, serious research like you’re studying for the biggest test of your life because you are.

Most truly successful people I know are not posting online about their success every day. They are too busy doing the work.

Be careful of surface-level research, i.e. the information that finds you.  As soon as you search for anything related to starting a business, you will get hit with many ads trying to sell inspiration. I am at a point now where I cringe when I hear the word ‘inspiring’ – simply because what people think is inspiring is often untrue.  I have seen people with millions of followers post about how excellent everything is with the perfect company image, later sit down to dinner and hear them divulge what is going on. I have watched business influencers take credit for other people’s work. I have watched influencers outright lie about their circumstances to sound more inspiring, simply to gain more followers and more affirmations of success in their comments.  I guess what I am saying is to be very careful. I have been fortunate to see first hand the disingenuous world of entrepreneurial ‘inspiration’ and the misinformation around the path to success. I see this as very dangerous as I have seen people dive into a major project based on excellent motivation, but the person who inspired them has not even done it.  Then, suddenly, the person who was “inspired” has real-life consequences and the influencer just goes about their life gaining more followers and more money without a care in the world that they inspired a string of poor business decisions. Of course, there are a few exceptions. Still, I advise you to be highly diligent with what you believe, always check multiple sources, ask yourself if they are sharing the information as it is a clickbait headline or factual information, think about their motivation for sharing their message. It is likely not to help you, but to gain followers and feed their ego. Most truly successful people I know are not posting online about their success every day. They are too busy doing the work.

Our constant drive to accomplish more and more has made it impossible to experience life completely, ushering in an ominous, perpetual feeling of dissatisfaction.

I once congratulated a business influencer I met on their success and asked them for insight about a distribution play their business had made. They stared at me and said, ‘oh, I’m not an active owner’, and then I learned they pretend they run their business on their social media but have a CEO and an entire team that does. They post about ‘how busy’ they are, but off-camera it was a very different story. They knew nothing about distribution or any in-depth information about the business at all. Of course, if you have the funds and the audacity to post online and pretend that you are doing other people’s work, I guess that is an option. Once again, a peek behind the curtain revealed a less than honest portrayal of entrepreneurial life. 

Be sure that you do not get “inspired” by a lie, the ‘oh they are just like me, I can do it too’, but they forgot to mention the loan from their family, the team behind the scenes, the free place to live, the massive inheritance that makes failure less impactful, or the life circumstances and timing that made it work for them.  Think about your circumstance, gauge what you have in your favour (and what you don’t), and extrapolate the risk level and decide what you are and are not willing to give up.  Ask yourself, what happens if I fail? Make sure you have a rough plan of other options if it does not work out. There is nothing so desperate as when there are no alternatives. You need to fail quickly so you can regroup and try again without evaporating all of your support.

For example, if you are single with major inheritance coming your way, you would approach risk in a very different way than if you have a family to support and live paycheck to paycheck.  Look at your personal information, your costs of living, especially the essentials, i.e. you can probably forego buying another pair of nice shoes. Still, you NEED insurance, food, warmth and so on.  This may sound obvious, but once emotion kicks in and people start pouring all of their savings into a failing business, their funds go fast – so know what your limit is, what is the dollar amount you need per month to be fed, safe, warm and secure.  That is your base number, and you need to plan your life to have at least that income.  Many people do not know this number, which is the beginning of where things start to go wrong.  The classic phrase “a problem shared is a problem halved” I think should be “a problem known is a problem halved” because once you truly know the problem, you are on the first step to solving it. 

“I repeat: minimize the risk!”

Minimize Risk

Too many people have loose numbers in their heads, flexible ideas of what they need and so on.  Before you embark on an unpredictable entrepreneurial venture, understand your financial picture and automate your finances so that you can 100% focus on building your business without worrying if you and your family will be able to eat.  Ask yourself the tough questions early on. What happens if it does not work? What happens if the business closes? And, plan so that if it does close, you do not find yourself in an almost irrecoverable situation.

Likewise, as things start to go well, just sit with it for a minute, don’t just start spending immediately as on the whac-a-mole rollercoaster of entrepreneurship anything can happen, so stay focused and continue to protect the downside. 

In my view, ‘Entrepreneurs love risk’ is a ridiculous phrase and creates a false image. Especially since every successful entrepreneur I know spends their entire time trying to mitigate risk! A failed business in your 40’s is very different depending on your support network and finances.  I am not saying don’t do it. I am saying that you might want to approach it differently depending on your circumstances to maximise the upside and protect the downside. 

I would encourage mapping your weekly hours before giving up the stability of your current job and income.  Most people waste an insane number of hours every week.  Let’s say you have an 8 hour a day job, and you sleep 8 hours a night. You have 56 hours left of your week.  Now, let’s assume 16 of those hours is personal time. You still have a full 40 hours a week to work on your new venture.  Discipline yourself to build the new venture while you still have the security of your job. The ‘all in or bust’ approach often portrayed as a right of passage is, in my opinion, total madness. Suppose you put in these hours on top of your job, and your dream starts to show a little bit of reality, a few sales with positive reviews, some form of tangible and unbiased traction, an investor with genuine interest, and so on. In that case, that’s the time to think about a complete pivot.

Whether you are embarking on a big or small entrepreneurial venture, the same key indicators apply.  For example, a friend of mine is an incredible painter and has a family to support, so she looked after her family, kept her main job, and diligently worked on setting up her art business.  After six months, she sold things faster than she could paint, so she started to wind down the hours at her job and eventually made a complete transition.  She did not sell a lot on day one or day two because things take time to build, so it was good that she still had her primary job.  Her choices made for a solid and low-risk transition. Regardless of the outcome of her venture, she would be financially stable because she was managing the risk. If she was independently wealthy, she could have done things differently. However, she was responsible to her family and, with careful planning, achieved both her dream and maintained her and her family’s lifestyle.  The most painful scenarios I have seen are when someone has spent all their savings on a failed dream. It is tough to try again and arguably even more challenging to live at a lower standard of living because it is a daily reminder of failure.

Please do not, under any circumstances, get anchored on the biased <1% of stories to make a significant life decision. 

A lot of people give up stability too soon. This leads them to a shorter runway to succeed before they are forced to go back to full-time work.  The common mantra ‘I risked it all and started my venture’, may well be a sexy clickbait headline, but the reality is, in a world where 90% of startups fail in their first two years, ‘risking it all to start my venture’ is a fool’s errand. Map your life and hours, build diligently around the stability of your job at first, then if you encounter an issue with your dream idea, you are no worse off. You have learned to build. You now have experience, and next time, you’re starting from a place of precious knowledge.  

I know from my own life that it is much easier to build a second time! The million and one things you learned the first time around are ‘top of mind’, ready to apply quickly and efficiently to your new venture. You have contacts in the space, so you’re no longer starting from scratch. You’ve learned all the processes, the tech stacks, and, of course, you can joyfully avoid all of the painful and, in hindsight, obvious mistakes you made the first time. And, because you never gave up stability, you can build again. Math doesn’t lie. From the 10% that don’t fail immediately, how many of the remaining open businesses are profitable, better than your other options, worth the time/stress/risk, etc.? It’s not many, so go in with your eyes wide open on entrepreneurship statistics and do everything you can to objectively know this is a good business before risking family stability and life savings.

Of course, we have all heard the unicorn stories about sleeping on the floor for years and eating cans of tuna and making it happen – I am not saying they do not exist, but do you operate at your best when you live like that? I know I don’t. It’s quite simply a sample bias. The media leans towards the stories of overnight success; call it the easy path, the rags to riches, the business “struggle porn” that worked out in the end. All the other stories make it feel like you haven’t succeeded because you haven’t taken the risk—total and utter BS. Risk does not lead to success in and by itself. Risk leads to a mathematically weighted chance of failure. That’s why it’s called risk.  Please do not, under any circumstances, get anchored on the biased <1% of stories to make a significant life decision. 

When I first read James Dyson’s story and how he still owns a billion-dollar company in full because he mortgaged his house to the max to fund his company, I thought it was epic.  I have since readjusted my thinking because James is the exception to the rule. You can’t swim in entrepreneurial circles without hearing about all the catastrophic failures that people have endured. From failures that ended as failures and failures that propelled new success. Either you realise that these are treacherous waters and far from the colourful, happy Instagram moments we all get bombarded with.  Thousands have risked it all and failed, and in the process, put their family in jeopardy and ended up in a callous place. Imagine if that 10,000th vacuum cleaner prototype didn’t work. At that point, James had spent ten years, all life savings, all personal time, and had nothing tangible to show for it. That is the reality for 99/100 people, so you need to be fully aware of that before going ‘all-in’… why not go ‘enough to risk what you can, putting in every hour you can, outwork everyone, to get to a place of real traction and get it verified by people more intelligent than you, then when you leap your odds of success are significantly higher.

Stop! Consider what you’re truly willing to lose before jumping into a business head-first.
I know this sounds like a rant against entrepreneurship, but it is more of a rant against going into entrepreneurship too early or for the wrong reasons. My pessimism, in a sense, comes from a near-epic failure in my first business. The fact is that when it ended if I did not have the support of good friends and family, I would be in a very tough place.  I went all in, and as more and more red flags reared their heads, I just worked harder and harder, more and more.  When it was finally over, I sat with my brother, and we spent hours debriefing on the good, the bad and the ugly, a post-mortem of the business.  

Of course, there were good moments, but the bad stuff was overwhelming – why did we keep trying to push through? Emotion? Saving face? The Entrepreneurial Dream? The eternal optimism of a first-time business owner?  I was blinded by sheer hope in hindsight, and I latched onto phrases like ‘those who succeed never give up. I have since learned that this phrase relates to the person, not the business.  If there is a fundamental issue with your project, admit it, evolve and rebuild or just stop and do something else. Businesses close all day, every day. There is no shame in it.  Building a business from an idea in your head that then grows to the point where you are wealthy is one of the hardest things to do, so when it doesn’t work, that is not a failure. That is the expected outcome!

To help keep a level head and access your business, focus relentlessly on learning and building a network of people you trust and respect and who will give you honest feedback.  Keep yourself honest, too and think logically through YOUR situation. Ask yourself:

What do YOU define as a good life?  

What are YOUR skills?

What are YOUR goals?

What are YOU trying to build?

What are YOU willing to risk?

What are YOU not willing to risk?

The answers to these questions do not prevent you from building. They may just adapt how you build.  If you have the idea but are not a leader, find a business partner.  Suppose you are not from a wealthy family. In that case, you might be more cautious about what you are willing to risk financially, in which case find investors early on. You will own less of your business. However, you will also risk less, and the financial upside will likely still be significant if all goes well.

Once you truly know what you are getting yourself into, I think the next question is, what does it take?  Once again, online, we see the good stuff. We do not know the grind, the sacrifices and the everyday ups and downs of entrepreneurial life.  Sure, you no longer have a boss, but you will most likely have investors, and in a sense, your company is your boss, and this boss is relentless with no respect for the time of day, weekends or family commitments – if it needs you, more often than not, it requires you now!  Are you willing to sign up for this? In the early stages, you also have no support team, no 401k, no dental, no paid time off, no sick leave, no promotions, no one else working when you’re not, and all the other downsides of starting from zero by yourself. Do not let the dream of ‘freedom’ guide you down a path you aren’t financially or emotionally able to handle. As the old joke goes, an entrepreneur is French for unemployed. You will be doing more work than ever, initially, for zero income – be prepared for that.

My co-founder and brother, Chris, and I on set. Building and improving always.

Building > Dreaming

I have noticed from many calls over the years with budding entrepreneurs that people often want other people to do their work.  People ask me the most basic questions, which are readily available on hundreds of websites for free. I have spoken to people who have not even researched the basics of how they are going to get an idea off the ground. I can’t help with that.  If they don’t have the motivation to do the level one research and want me to lay it all out over multiple phone calls, I honestly don’t think entrepreneurship is for that person. They’re not building. They are just thinking or dreaming about building.  

I cannot build a company for them, and that is often what people want.  But, you have to want to build it yourself. I can help with the things you cannot find online, the nuances, but not the basics. The amount of people who’ve asked me about the very basics of deciding LLC vs C-Corp, or Convertible Note vs SAFE, is painful… there are hundreds of resources for this online, so why are we going back and forth, scheduling zoom calls, for you to ask me this? I genuinely enjoy helping people and seeing them succeed. Hence, I try to guide them into researching these things for themselves. Not because it is easier for me, but so that they get into the motions of research. If they cannot explore questions with answers, how will they research issues with no definitive answer?

On a side note, also be aware that building a project is not only continuous, it can also be very lonely.  Even if you have a business partner, you sit at your computer by yourself, working out the answer for yourself. Often, there is no answer in the traditional sense… you will be continually making best judgement decisions based on less than perfect information.  You just have to keep researching it and try to fathom the best way forward.

In my opinion, you have to love the process. If you need to drum up the motivation to work on your own company, it is not for you.  You need to have excitement, a passion and a yearning to create to be an entrepreneur, but you also have to have the self-discipline to do the parts that are not your passion.  I doubt that anyone starts a company thinking, “oh, I can’t wait to dive into what insurance I need”, or “I love researching entity structures”, and “I just cannot wait to build the cash-flow model”.  But, it has to be done and done very well. 

Telling people about the book you are going to write over and over again is pointless if you have not started writing it.  Words are easy. Action is hard – you simply have to take action.

So, before diving in, I encourage you to strip away the hope of the glamour, the money, the accolades, the social standing as an ‘entrepreneur’ and instead focus on just doing the work. Of course, ‘the work’ varies depending on what you are trying to build, but in essence, what I mean is stop talking and start doing.  Hours at the coffee shop telling people about your new business are an endless waste of time if you have not built a pitch deck or put together a research document. Telling people about the book you are going to write over and over again is pointless if you have not started writing it.  Words are easy. Action is hard – you simply have to take action.  Work out your goal, work out everything that has to happen to get there, and then start at step one and work upwards from there.  If you can work diligently every day to nudge everything forward and move closer to your goal, you are in a perfect place to build your venture.  

Also, I want to point out that if you don’t have this yearning, that is fine. That is YOU.  In certain circles, you are pressured to be ‘doing your own business, but it is not for everyone, and that is fine.  Feel comfortable working out what you want and where you want to fit in. To do this, I think you have to filter out the noise. This is not what your parents want you to do, not what your partner wants you to do, not what your cat wants you to do, what YOU want to do. Not everyone is a creator, not everyone is a leader, and that is a good thing! There are a million other wonderful things you can do with your life.

If entrepreneurship is not for you, then great. It is sometimes easier to identify what you don’t want to do, who you are not, and identify what you want to do. Keep researching and narrowing things down, and eventually, you will find the glove that fits.  I find that writing down skills and interests helps a lot. For example, I love making films. I love comedy, but I do not enjoy the process every time I have attempted to direct. I love the “idea” of directing, but my reality is that I don’t like actual directing.  So, knowing that I am not a director is fantastic as it allows me to hone in on the parts of the creative process that I do like. 

Exhibit A of the parts of the creative process I like: wearing funky outfits = fun content.

Create Value

Now that I have drilled in some harsh realities, if you are still excited about starting your venture, maybe it’s for you! I love it.  But, I am thrilled that I didn’t get into it due to hype. I got into it due to an incessant need to create. Whether I am making money or not, I am always in creative mode. I just need to get these ideas out of my head and onto paper or into reality. But, of course, creativity is the fun part, the crazy, awesome, everyday excitement of getting to bring your idea into reality, whether that’s a product, service, film, property or any other project.  Suppose you can pair your creativity with the reality of costs, distribution, manufacturing and all the parts of a venture that make your creativity a reality. Then, in that case, entrepreneurship is a good option for you. If you can create value for yourself and your customers, that is a win/win, and you are heading off on a fascinating path.

Remember always to be careful about taking advice from anyone whose life is not affected by the decision

In summary, please remember always to be careful about taking advice from anyone whose life is not affected by the decision, and, of course, my life is not affected by whether you decide to start your venture or not. Still, I genuinely hope this has given you some positive pause for thought. 

I hope that you take the time to look honestly at your circumstances and your motivations. If you decide to build your venture, be sure to strive for the upside, remember to protect the downside, and DO THE WORK!

Jen is an entrepreneur and filmmaker. Follow her journey here.

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