How I Stopped Being An Asshole Entrepreneur

I used to be an asshole. Not in the self-deprecating, funny, quirky sort of way. I used to be the kind of asshole who would make people leave dinner parties and resign jobs. The kind of asshole that people don’t want to work for, don’t want to socialise with and don’t want to call their friend. 

I’m not trying to be humorous here either. It was very difficult to be around me for many years.

Unbelievably, I wore this like a badge of honour, an “A-badge” if you will. I used to proudly declare that upon meeting me, 50% of people hated me immediately and from the rest, I would try to patch together friends or business partners. Those are some shitty odds to impose upon yourself.

Being an entrepreneur is a conflicting endeavour. It’s your job to stay positive, to build something from nothing, to create a narrative and build a vision of the future that you can sell to other people so that they join you and help you build this vision of the future. It’s also your job to get the best out of people and build hard things, to strive for perfection and fight for survival, to be well-read in a wide range of topics while you dive deeply into your particular vertical. It’s a combative career choice filled with ego, failure and massive success if you get a million variables right at precisely the right time. 

Entrepreneurs are always competing. With themselves, with their colleagues, with fellow entrepreneurs, with actual competitors, with partners, siblings, parents and anyone else we can find along the way to compete with. 

There are books, TV shows, podcasts, articles, interviews, movies and legends of entrepreneurial assholes who created the world we live in today because they pushed for perfection at every possible turn. The example that jumps to mind is Steve Jobs. A notorious asshole perfectionist who excelled in almost every avenue of business that he touched. I read the Steve Jobs biography written by Walter Isaacson when it came out in 2011 and instantly became an even bigger asshole than I already was. You cannot fathom the magnitude of asshole that I was at this time. It must have been unbearable. It was laughably predictable and embarrassingly ineffective to fall into the trap of believing that the core reason for his success was that Jobs was an asshole and to repeat his success I just needed to be an asshole too. 

That is absolutely, 100% not the message of the Jobs biography. The message is that Jobs had to learn to be less of an asshole to truly find success and happiness. I completely missed this message and ploughed forward treating my friends, family and staff like they were mere mortals and I was a god sent to them to create a company that would change the world. 

I didn’t change the world and nor did my company. 

I was never going to change the world with that shitty attitude. 

It wasn’t just in my professional life that I was an asshole. In my twenties, I would attend dinner parties with close friends and slowly manipulate the conversation toward topics that I was comfortable with and had read up on extensively so that I could appear to be the smartest person in the room. I am embarrassed by this looking back on it now and don’t know how I kept any friends at all. But the shocking thing is that when I looked back on this time with my psychologist I realised that slowly but surely, as I started to manipulate the conversation more and more, my friends would quietly pay their bills and leave, one after the other. They literally couldn’t stand to be near me. 

Something had to change. 

The breakthrough for me came when I was forced to drive myself to the hospital, burned out with a stomach ulcer that was ready to burst at 2 am in the morning. 

I had nobody around me. My partner was in a different part of the country. I had left my family, my friends weren’t close enough friends to call at 2 am and I was desperate. 

So over the next few years I started to drag myself out of the asshole spiral. 

Here are a few things that changed my life:

Find A Professional

You think you can psychologise yourself. You can’t. 

You think you can therapise yourself. You can’t. 

You think you can council yourself. You can’t. 

You need a mental coach as much as you need a personal trainer for your muscles. If you are trying to be the best entrepreneur you can be, you need perspective, you need a coach, you need a psychologist, you need help. 

And why wouldn’t you utilise every possible resource to become the best version of yourself? Why wouldn’t you want better mental health, stronger mental fortitude, more resilience and the ability to gain perspective on your actions?

I thought I was fine without professional help until I bit the bullet and found a psychologist who changed my life. 

Listen More, Talk Less

I started to derive energy and value from listening and not talking. This was one of the most difficult changes I had to make. 

I finally understood my grandfather telling me that people have two ears and one mouth for a reason. Listen more than you talk. It’s incredible what you can learn when you shut your mouth and listen. 

This applies to your business, your personal life, strangers, meetings and everything else. 

Listen and learn don’t talk and enforce. 

My Opinion vs Your Opinion

I read a lot and that provides me with strong opinions about a lot of topics. I am not right about these things, I just have strong opinions about them. 

But here’s the thing: I know what my opinions are. I don’t know what yours are. 

What’s the best way to figure out what other people think? Listen to them. 

When I reframed listening as the acquisition of other people’s opinions, everything changed. I began to listen to my team, my partner, my parents, my friends, and people online and devour their opinions so that I could challenge my own. 

Your opinion is only valuable when it is held up against other people’s opinions. If you never challenge your perspective then how do you know it holds up?

Winning

I realised that just because my opinion was right for me didn’t mean it was the right opinion.

I studied debating at school. Debate is an art. It’s not a stupid Twitter argument with a nameless, faceless troll. But not every conversation is a debate. Debates usually require two opposing sides to battle one another and in the end, there is a winner and a loser. 

Sometimes a conversation is just an exchange of opinions, not a battle. Trust me, you’re not going to change anyone’s mind over a beer at a pub. So get comfortable expressing your opinion and then moving on. 

Personal Values

At the start of my transformation from asshole to whatever I was becoming, I started to codify my personal values into what I now call my Nicisms. 

Whenever I experienced something that shifted my perspective enough I would write it down and over time I evolved these perspectives into a set of personal values that I now live by. Some drop out occasionally and new ones enter when they shift my world again but on the whole, they are constant and help me lighten the cognitive load of decision making. 

Here are my Nicisms, in case you need some examples: 

1. There is nothing after this

2. Learn the rules but ignore them

3. Be honest if possible

4. Do more but sometimes wait

5. Be patient

6. Trust people until you have a reason not to

7. Listen more, talk less

8. Everything is easier without ego

9. Burn it all down if you have to

10. Strong opinions loosely held

11. Be consistent

12. I am not building a future. I am building a life.

13. Find an optimal challenge

These values trickle into every aspect of my life. They help me figure out what businesses to build, and who to bring into and remove from my life. They help me quieten the asshole within. 

Learn to Apologise

I hate losing. I hate getting things wrong. I hate when other people tell me something and I disagree but am proving wrong later on. I hate it. 

I hated getting things wrong so much in my past that apologising was agonising for me. It was a sign of weakness. It was proof that someone else had beaten me. 

This applied to my friends, my life partner, my co-founders, my employees and mentors, everyone. I hated apologising or admitting I was wrong. 

But then one day my partner and I got into a fight/debate about a petty issue and she said something to me that rocked my foundation: 

“You realise we’re on the same team, right?”

I stopped dead in my tracks. 

I thought about her statement for a minute and then realised that we were, in fact, on the same team. So I apologised for my aggressive approach, listened to her opinion, decided I was wrong and her view was the appropriate one and moved on. 

Apologising is a sign of strength, not weakness. 

This newfound ability to apologise and mean it sincerely has changed my life for the better. 

It helped me drop my ego, it helped me bring people into a safe space and provide them with an intellectual victory that imbues confidence and makes them feel good. “Losing” can be a form of winning if you’re playing a long enough game. 

If you’re all on the same team then the end goal must surely be victory for everyone, not just for you at this particular moment?

Being an asshole entrepreneur was holding me back and it’s probably holding you back too. 

It’s a fallacy that you need to be an asshole to be effective. It’s fallacy that only the assholes survive and thrive in business or as entrepreneurs. 

I know a lot of successful people who are nice too and I want to be one of them. This is how I have started my journey.

Why You Should Need a License To Nap - Dale Rae on the Curious Cult Podcast

In this episode of the Curious Cult, Dale Rae and I chat about the science of sleep, how certain things in society (like working hours) are built around some, but not everyone, and about the power of consistency. This is a fascinating conversation and is worthwhile listening to even if you’re exceptional at sleep.

Dale is the founder of Sleep Science, a former senior researcher at the University of Cape Town. She’s obsessed with the science of sleep and is also the mother of two little kids and is passionate about mountain biking. 

Key takeaways from the episode

Sleep deprivation is a dangerous badge of honour

Many people, especially startup founders and entrepreneurs, glamorise a lack of sleep and seem proud of living on 3-4 hours a night. But it’s not sustainable and the body’s ability to take abuse in the short to medium-term can lead to long-term problems and a severe lack of sleep will catch up years down the line.

Choose your preference: Work in the way that works for you

“Night owls” and “larks” speaks to a sleep pattern and habit, but it goes much deeper than that. According to Dale’s research, the way you are biologically inclined to sleep affects everything in your day, like your exercise routines, your creative efficiency, and your eating habits. So whether you are a night owl or a lark, do your best to build your day around your most productive and efficient times instead of trying to force habit against your biological preference. 

Data is important, but over-tracking can be inefficient

Tracking data can be helpful if there’s a problem and you’re looking to solve it or improve it. But if the data is overanalysed, you might end up trying to solve a problem that isn’t there. For example, if you start tracking your sleep, it can give you interesting data which you might be able to use to better your habits. But if the information contradicts how you are feeling on the day-to-day, measuring it and over-interpreting it might not actually be helpful. 

The golden rule: Consistency is key

With all things in life - from sleep to exercise, work to food - developing routines around consistency is the best way to establish sustainable habits. It’s important to recognise that flexibility is important too. Instead of forcing a bedtime at a certain time, having a range of about an hour or so leads to routines that are far more likely to last. In the same way in work, remember to include flexibility in your regime and take breaks to maximise your efficiency. 

To keep updated on Dale and Sleep Science, you can find out more information here, on Instagram and on Facebook. If you enjoyed this episode, please share it far and wide and let’s start changing the world with curiosity.

Your Side Hustle Should Be Additive Not Subtractive

It’s so easy to start something that you end up hating:

1. Start something new without much thought behind it

2. Do it for a short time

3. Watch vanity metrics only and become frustrated with your lack of likes and followers

4. Keep going but hate the work because your goals are not defined or badly laid out

5. Eventually, quit but not after pain, suffering and loss of capital

That’s it, that’s how easy it is to start something and hate it very quickly.

I believe that side hustles are a fantastic way to make some extra money and also live a bit more of life. Find project, problem or business that interests you and then slowly start turning it into something that other people might want to spend money on. That’s the dream but it often doesn’t work out that way.

Here’s a small tip that can make a huge difference to how you build out your side hustle income streams:

Side hustles should be ADDITIVE to your life and not SUBTRACTIVE.

When you build anything of value it should add more to the life that you live, not subtract from it. Yes, of course, it will be difficult but ultimately it should not be bad or subtractive.

If you decide to start a side hustle and you commit the time and attention to do so you should also be patient and consistent without adding negative pressure to your day to day life.

To make your side hustle additive you should consider the following:

How much time do you really have to commit to your side hustle?

Most people believe that they live full lives and don’t have any extra time in their day to allocate to a new project. The litmus test for this statement is to count how many hours of your day you spend watching TV. For the average person, that figure is anything between 4hrs and 8 hrs PER DAY!!!

If you watch two hours of TV a day then you have two hours a day to build a side hustle. If you can only afford two hours per week, that’s great, segment that time out, put it in your calendar and spend focused, dedicated, non-distracted time building that bad boy out! But remember, do this consistently and be patient. Work in the allocated time and don’t let yourself get distracted.

Have you defined your success triggers?

What does success look like for this side hustle? Are you trying to make a shitton of money or just a little? Are you trying to build an empire or a small and steady stream of income? This part is so key to allowing your side hustle to be additive.

If your goals are too lofty and unrealistic then every minute spent on it will seem like it’s not enough and that you’re letting yourself down. Make sure to scrutinize your success triggers so that they fit in with your life.

Do the people in your immediate life know you are starting this project and understand how much of your time it’s going to take away from them?

If you don’t tell anyone in your life that you are starting something new and big that is going to sap your time then they are going to flip out when you disappear. And that’s on you.

Communication is imperative when it comes to your side hustle so do me and yourself a favour and talk to your kids, your friends, your partner, your parents and whoever else you have commitments with and let them know what you’re planning. They don’t have to like it but you do have to talk to them.

Are you mentally and physically fit enough for this new challenge?

Sure, the main reason most people start a side hustle is to make money but that goal alone isn’t enough to drag you through the mental and physical anguish that a side hustle might cause you. There is no quick way to make extra money (if anyone tells you there is then they are probably trying to sell you Herbalife or Amway pyramid schemes) and if you come to terms with this fact then the most important thing you can do to make your side hustle additive is to get your mind right and treat your body with care.

You can’t stay up until 2 am every morning, eat shitty food and never do any exercise but still expect to stay healthy, mentally fit and ready for the stresses of an extra project on the side.

Take care of yourself first and the rest becomes much easier.

What is Entrepreneurship: The Characteristics of an Entrepreneur

Entrepreneur Success Stories: 51 Businesses That Started as Side Hustles