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.

Think like a Founder - Important Habits You Should Adopt

If you are launching a new venture, starting a side hustle or thinking about making a big shift in your life then you are probably considering what it takes. What does it take to start something new? What does it mean to your life to commit to building something and succeeding?

I have been a founder many times over the past twenty years and I surround myself with the best founders, business builders and leaders out there. There are some things that business founders do that I think are imperative to your own success if you are starting something new. Here’s a breakdown of what I think founders do that other people should adopt when building something.

1. Obsess

There are problems everywhere. That means that there are solutions waiting to be turned into money everywhere. My favourite founders choose to work on problems that they are obsessed with.

Talented people can work on just about any problem and can likely make it a success of some kind. But it’s when founders obsess over the problem or the solution that they really turn up the heat.

It’s perfectly OK to obsess for one day a week or one hour a day. Your obsession can start out slowly and come up in a nagging sort of way. If you are obsessing then you want to work on the business or venture wholeheartedly. If you’re obsessed with food and eating the right kind of fuel, you’re likely to be a fit and healthy person. If you don’t really care too much about what you eat and how it affects your training then you’ll probably struggle to get into the best shape of your life.

The best founders obsess and that’s a good place for you to start: What are you obsessing over and is that what you are working on every day?

2. Focus

You can’t build multiple side hustles at once. You think you can. Other’s will tell you they did. You’ll really want to but you shouldn’t.

Saying “no” is an indication of obsessive focus. The more you say no to, the more you can focus on the thing you are obsessed with.

If you try to take on every opportunity then you’ll lose out on all of them instead of capitalise on the most lucrative or unique one.

Start saying NO more often, even if it feels like you might be losing out on something.

If you consistently feel like you’re losing out then maybe you’re working on the wrong thing and it’s time to rethink your obsession.

3. REVENUE

Early on in a startup or side hustle every action should lead to revenue. If it isn’t something that will take you a step close to earning money then it shouldn’t be your focus.

Sales and revenue matter more than just about anything else.

This means that if you need your product to improve to make a sale, then that’s a focus. If you need your YouTube channel to hit 100 000 subscribers before revenue, then that’s your focus. Figure out what your triggers are for revenue and then double-down and focus, obsess on hitting revenue.

4. Deliver

Don’t faff around trying to make whatever it is you’re working on perfect. PERFECT DOESN’T EXIST. You are never going to get to perfection and if you think you will, you’re in lalaland and need a hard reset in your thinking.

Stop. Assess what you have. Launch. The first thing you launch is never going to be the best version of your vision but at least it’ll be out there in the world. Deliver something to someone and listen to what they have to say. Put your work out into the world, it only counts when other people can use and critique it.

Many have said it before me: Ideas are fucking worthless, execution is everything.

5. Listen

It’s easy to start something new or make a change when it’s just you on your own. You essentially run your own little dictatorship of one. You decide what to build. You decide when to build it. You decide how it works, what it costs, where it lives and when you make changes.

Then you launch.

And then everyone has an opinion.

It’s difficult to take on every opinion you hear but the best founders listen and know how to curate who they listen to. You can’t take on everyone’s opinion but often when users are telling you something it wont just be one person with one opinion, it’ll be multiple users reporting the same feedback and that’s when you listen and then follow steps 5 and 6 below.

Build, launch, listen, iterate, adapt.

6. Iterate

The first version of whatever you’re selling is going to be good enough to get out there but not good enough to use forever.

Deliver the next feature. Add the next service. Upgrade the product. Listen to feedback (see point 6) from customers and implement the most relevant and practical suggestions.

The faster you can create a flywheel of iteration the better your product will be and the happier you’ll keep your customers.

Build something. Release it. Gain customers. Watch how they use your product. Listen to their feedback. Build the next version. Release it. Repeat.

That’s a simple flywheel that most founders I know use.

7. Adapt

“Everyone has a plan until they get punched in the face.” Mike Tyson’s famous quote applies to the start of something too. If you think you know how people are going to use your product you are sorely mistaken. You have no idea what’s coming at you until you release your baby into the wild and see if it can survive as you planned or if you need to adap, change and rethink the plan.

This is why point 4 above is so important. You have to get over your need for perfection. You need to overcome your fear of what other people say. Founders don’t give a shit what their critics say. They build, deliver, release, listen and adapt.

If you are afraid of making small tweaks, tiny pivots and slight adjustments as you go then you’re likely going to cling on to a sinking ship and drown.

Obsessing is great but do not obsess over the perfection of your initial idea or product. Be prepared that whatever you are building or launching is going to change, even slightly, over time.

8. Be You

In a world of infinite information and personality-overload it’s very easy to find someone to copy. We see the success of the Kardishians of the reality TV stars of the people who do nothing, contribute nothing but have a personality and we think we can do what they did.

You can’t be a better version of Kim Kardashian than she can be. You can’t be a better version of Casey Neistat than Casey. You can’t beat Jordan Peele at his own game or take Trevor Noah on at being Trevor.

But you sure as shit can beat them with your own brand of insanity, skill, dedication, obsession and focus. You can beat anyone in the world at being the most version of yourself that you can be. Founders know this intimitaly and it’s a hidden super power. Everybody reads about Steve Jobs being an asshole and the founders I know who tried to be like Steve - even I did for a brief and devastating period in one of my businesses - suffered greatly because we’re just not built like Steve was.

You need to figure out who the fuck you are and want to be and then you need to be that person as much as you can be.

Be yourself, relentlessly. It will pay off.

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