Let’s dive a bit deeper into what it takes to live a big, meaningful life. Some of what we cover in this chapter may challenge you, or you may have resistance to really taking on board what I’m saying. Do your best to embrace it. Yes, it might be outside of your comfort zone, but trust me, I know what that feels like. I intimately know that initial feeling of fear, that lack of confidence, that thought: ‘Can I really do this?’ It’s totally fine to have that thought; what isn’t fine is to let that thought dictate your actions. You want to dictate your actions. You want to be in charge of your life.

Let’s start by looking at the kind of smarts you need to be successful. If you do nothing else but focus on these six principles, you’ll go a long way.

The smarts you need (and they’re not what you think)

I wasn’t an A student by any means, but I was determined to not be stupid. One of the many things that paralyse us in the pursuit of our goals is thinking that we’re not smart enough to achieve them. The self-doubt, the worry that we can’t compete and believing that others are smarter than us can be crippling. But remember: we’re all smart at what we’re smart at.

Steve Jobs said, ‘The world is full of people no smarter than you and I’. People usually think that being smart is about being clever, nerdy or really good at maths. It certainly can be those things, but being smart is about much more than that: it’s about the decision-making process. Don’t worry about what grades you did or didn’t get in school or at uni (remember, I got 44 per cent in year 12 and I dropped out of uni), and instead focus on six principles: be informed, be selective, be open, be determined, be committed and never stop learning. That’s all the smarts you need to excel.

Be informed

Make informed decisions. It only takes a small bit of extra effort to research and understand something more than you did before, so take the time out of your day to inform yourself about what you’re pursuing. Study daily, even if only for 10 minutes, and take notes. Never underestimate the amount of education available online through peer to peer. The more you know, the smarter the decisions you will be able to make. Remember that after 10 000 hours of doing one thing, you’re considered an expert. This doesn’t require a genius level IQ — it requires continually working at the same thing.

Be selective

Be very selective when it comes to your time, and your money. The smartest people are those who manage their time and money the best. Being selective also means learning how to say ‘no’ to people and projects that would take you off course, which isn’t always easy, but it’s important to learn how to do it kindly and firmly. Remember the 80/20 rule: 80 per cent of your results come from 20 per cent of your actions. Identify what those actions are and focus on more of those.

Be open

Being selective doesn’t mean that you can no longer be open to new things, ideas or people. In fact, the more selective you are, the more you’ll be able to weed out the good from the bad, and you’ll find yourself being more open to the new. Know and accept that the path to your goals will be new and uncertain, with unknown obstacles. When you’re open, you’ll discover new ways to get past challenges and continue moving forward. It’s so important to be open.

Richard Branson once told me a story. He was running late for a meeting and the taxi driver who picked him up was begging him to listen to a music tape of his because he knew Virgin was involved in recording music. Branson was anxious, and worst of all the driver had left the tape at his mother’s place. The driver persuaded Branson to allow him to drive to the meeting destination via his mother’s house to listen to the tape. After a much longer than expected trip, Branson listened to the tape and was so impressed with the song that he agreed to meet the driver again at Virgin Records. That driver was Phil Collins, and that song was ‘In the Air Tonight’, which went on to become one of Virgin’s best-selling records!

You never know who you’ll meet — at what train station or beach, at what time of day — who may just change your life forever. That’s real.

Be determined

Determination means being focused on your goal, and having it in mind at all times. Be determined to achieve it, and utilise every moment to help you on your mission. For example, when others are watching TV to chill, you’re watching it for information. What kind of brand is this? What kind of new market is opening up? What demographics are watching this show now? It also means the path of your learning changes so the outcomes you require are the pieces of information you seek.

Be committed

Being committed means sticking to your cause and belief. Even when things are tough. It means designing your daily habits to support you for optimum performance — to be grounded and pumped, so that when challenges arise you’re instantly brainstorming how to move past them, rather than letting them get to you. Being committed is what takes you from a smart strategy with great potential to awesome reality.

Never stop learning

It’s essential to have an attitude of continuous learning; there’s always something you can learn, from everybody. Every day, focus on listening more than you talk, and see everything as an opportunity to learn. Ask questions. Be inquisitive.

Fake it

When you need to fake it, it means you’re pushing the boundaries, which is how you achieve more than you previously thought you’d be able to. Through almost every step of my business I’ve been in the deep end, under pressure. I’ve constantly started before I was ready, faking it until I made it, pulling it all together as I went along. It’s still the way I love to do business! The only way to progress to the next level is to look like you’re already there. I’m not the only one who does this. I’ve met people running massive businesses and people in really big corporate jobs who are still faking it in some ways, and for good reason. It helps build the future. I’ve never bitten off more than I could chew — though my tolerance for chewing a lot at once is pretty high!

OTG recently signed a million-dollar contract with a professional English football league team to make all the players’ outfits, on and off the field, as well as all the fan retail merchandise. It was a full suite of products, which we’d never done before, and we had a 6- to 10-week turnaround time on around 90 000 units. I knew we could pull it off, but it was definitely pushing the limits. The football league was used to dealing with massive, multimultimillion-dollar companies, so we had to act like we were one. We faked it, and we backed it up and delivered all the goods on time and to specification; it was a big leap forward for us. You’d be surprised by what you can pull off! Sir Richard Branson said, ‘If somebody offers you an amazing opportunity but you are not sure you can do it, say yes — then learn how to do it later!’

Build your parachute

Once you have your vision for your future and know the work you want to do, it’s important to actively create a network of people who will support you through thick and thin. The inner turmoil that comes with embarking on a new endeavour can make or break you. It’s a battle between what you think (and hope) you can do and what you believe you can’t do. You need good people who believe in you to abate your fears, and to remind you what you’re made of. There will be a lot of naysayers who talk you down, and though it’s usually a product of their own fear and anxiety, it can bring you down at times. Again, this is when you will need those good people around you — you need to be in the right environment to reach your goals. In fact, sometimes the only thing that holds people back is their unsupportive environment.

If someone is not empowering you, they’re not helping you become the best version of yourself. Don’t take it personally, and remember that it’s okay to move away from those kinds of people. If you have a network of people around you who don’t believe in you and what you can do — who don’t ‘get it’ — then taking a leap will be 10 times harder. You must audit your network. Walking away from unsupportive people doesn’t mean it’s the end of the relationship. Sometimes you’ll reconnect a few years later and be able to have a great, supportive friendship again. Always stay open-ended with that possibility for the future. Business philosopher Jim Rohn famously said, ‘You are the average of the five people you spend the most time with’.

I like the analogy of picturing myself in the belly of an aeroplane, ready to jump. The hatch is open, the wind is blowing in my face and I put on my goggles. Almost ready to jump, I reach back to see if my parachute’s on because that parachute is my lifeline. Would you jump without a parachute? In work and in life, when you’re confronted with a massive new challenge, your network of supportive, dependable, great people is your parachute. You can get on the plane, you can even fly up to a high altitude, but don’t jump before you have that network.

Hard conversations

Having hard conversations is a part of life. Sometimes there’s good news to share, and sometimes there are tricky, awkward things that have to be shared. Hard conversations typically happen when you quit your job, ask for a pay rise, need to fire someone, decide to break up with your boyfriend or girlfriend, have to tell your landlord you’re moving out, have to tell someone you can’t pay them back in time, need to break it to someone that they piss you off, and more.

One of the best strategies I’ve learned for dealing with hard conversations came from my chairman: ‘Tell good news fast, and bad news faster’. I use it all the time, and it’s helped me get through a lot of hard conversations. When it’s bad news, cut to the chase. Trying to soften the blow can extend the hard conversation further than necessary. Of course, you always want to say it nicely. Always. Just don’t beat around the bush. It’s like a bandaid: rip it off!

When you need to have a hard conversation with someone, make sure it’s in person. Never cop out and do it over text message, Facebook messenger, or email. That’s bad taste and negatively affects your long-term relationship. Face it, share it in person, be nice and be fast.

Another strategy that makes hard conversations easier is to set proper expectations in the beginning, before it gets hard. Before you enter into a commitment with someone — whether a boss, mentor, landlord or crush — have a conversation about the end. I know it’s not hugely romantic, but setting expectations well at the beginning is the best way to make what would be hard conversations much easier. For example, you can say, ‘I’m really excited about this opportunity. I think we’ll work well together. Let’s get started on this with a kind of probation, and review it together in a month to see how we’re going and how we’re both feeling’. If it’s a conversation with a potential boss or employee, discuss salary expectations, and more, upfront.

I’ve had to have many hard conversations in running OTG. There have been times when I’ve had to let people go because I knew it was the right time for them to move on, and it’s been tough. During the course of working together, we’ve become close friends, and now I’ve got to sit them down and say they’re being let go. ‘I don’t think it’s right for you, or for us, to continue moving forward. You’re not going to become the best version of yourself here.’ Saying it like it is — showing them I care about them and their own development and career, and facing the reality by having that hard conversation with them — has been essential for both parties.

You’re not in sales? Think again.

We’re constantly selling ourselves; it’s not just salespeople who need to sell. In employment we need to sell our ideas, get backing for initiatives, sell ourselves to get a pay rise, and so on. As an entrepreneur you’re selling non-stop. As a parent you’re selling ideas, behaviours, and better decisions and life strategies to your children. As a spouse you need to sell constantly to get your own way, right? So what is selling?

Let’s say the world is ending — it’s about to explode, and Richard Branson has a rocket ship, but he’s only got one seat left. You have two minutes to tell him why you should get that seat. People often think selling means a pitch like this:

‘I’ve achieved X and Y. I’m a positive person. I’m young. I’ve got great ideas and know how to execute. I’d be a great addition to your team.’

But this isn’t a very good sales pitch. Instead, you could say:

‘Richard, I know you’re going into space and you’re not coming back. Where are the gaps on your team? What don’t you have to successfully live in outer space?’

‘We have all the engineers and technicians we need, sorry.’

‘Okay, and how are you planning to eat? Do you have a chef, someone to cook for everyone and organise meal plans?’

‘Well, actually, we don’t have a chef …’

‘Cool. Hi, my name’s Mick and I’m a trained chef. I’d love to complete your team so we can survive out there.’

Selling is about asking questions to find out the problems people have, and then listening to their answers. From there, find the win–win. No matter how innovative and amazing a product, service, idea or strategy is, if it’s not what the other person is looking for, there’s no sale. The art of the sell is to build a relationship and find out the other party’s needs. And remember: sometimes people won’t buy what you do, they’ll buy why you do it and who you are.

Learn to negotiate

You need to learn how to negotiate. Everything is up for negotiation! Whether it’s asking for an upgrade on a plane, to have a deadline extended, to get a pay rise because of the results you’ve achieved, or to negotiate a better deal for a product or service. We negotiate every day of our lives: with our partners, co-workers, the guy at the car wash. We’re giving offers and making counteroffers, all the while trying to better our interests through the process. Think about discussing chores with your partner, or having banter about what’s the ‘right’ way to put on the roll of toilet paper — whose way gets picked? It’s all negotiation. When both parties feel they’re treated fairly, a relationship can flourish.

Get a person from ‘no’ to ‘maybe’, and ‘maybe’ to ‘yes’

How do you turn a ‘no’ into a ‘yes’? First, be so damn passionate about making it happen that you will literally do anything to get a ‘yes’. If you don’t feel that way, is this something you really want to pursue? If you do feel that way, great!

Ask questions so you can understand what’s holding the person back. Is it budget? Time? Personality? Great sales is about knowing the other person and getting inside their head — thinking how they’re thinking. Learn what’s stopping them from saying ‘yes’ so you can address those concerns.

Brett, a great employee of mine, came to me the other day because he was having some challenges closing a university he had already visited three times. I said, ‘My first sale after delivering the 400 cycling jerseys took me 13 calls to close. On the twelfth call I was ready to give up, but it was that last one that made the difference’. It’s all about persistence. Turn a ‘no’ into a ‘maybe’, and a ‘maybe’ into a ‘yes’. How can you go the extra mile? How can you wow them? Be persistent. Be passionate. Get inside their head to understand their point of view.

There will be a lot of ‘no’s’ when you’re desperately seeking a single ‘yes’. Sometimes you’ll go home dejected. It sucks. I’ve heard far more ‘no’s’ than ‘yes’s’ on my journey. But guess what? It only takes a single ‘yes’ to turn things around, and you never know where that ‘yes’ will come from.

Believe the sale is true before it is

In my view, if you want something to happen, you must believe it ahead of it happening. It’s not ‘the secret’; it’s making your mind believe something so that you approach it with total confidence and calm, already clear in your mind of the outcome. I have always focused on doing things like I can win, no matter what I’m doing — whether it’s an investment deal, a sale, employing staff or completing a project. It’s a must to believe in yourself and what you’re doing before you do it. You won’t win everything, nor should you — no-one deserves that — but with a total belief in yourself you’ll start making great progress. 

Rejection

This is a big one: it’s painful and sucky. In life, we’re faced with rejection all the time: relationship breakups, not getting the pay rise you expected, not getting that apartment you wanted to buy, not getting into the university course you so desperately wanted.

For me rejection started young. I was socially rejected because I was the odd one out — with my coke-bottle-thick glasses, being chubby and short — and it affected me big time. I was a target for bullying, which gave me a constant feeling of rejection. As an adult, I’ve experienced a lot of rejection too. I’ve walked in to pitch to prospective clients, excited about the great things we could do, to have them completely turn me down, not getting what I’m on about. I’ve had staff who I saw the best in — who I developed and mentored and gave my all to; or who I had sleep at my house to get us by when we had no money to pay for accommodation — reject me with their ungratefulness. It was painful and hard to realise that my baby had been broken by people who I thought were dependable and had the company’s best interests at heart. I’ve walked in to many investor meetings and pitches after days of intense preparation, so passionate about what I’m building and the path I’m going to take the investors on, for them to say, after showing great interest, ‘let’s relook at it in 12 months’. That is code for a big fat ‘we’re not going to invest in you’. I’ve put in heaps of hours to submit tenders and then haven’t been short-listed. Even more painful is when we’ve been short-listed, we’ve become super pumped, hoping to get first place, only to get second place — just missing out on the deal. Second place is first loser, and it doesn’t feel good.

Getting rejected is a natural part of progress. To make things happen you need to put yourself out there, make big asks and accept that not everything will come back with a nice ‘yes’. You may apply for jobs you won’t get. You may ask for pay rises you won’t get. You may work your guts out for three years on a start-up that collapses. The goal isn’t to avoid rejection, it’s to collect as much rejection as you can. To put yourself out there so much that you’re getting rejected flat out. The higher the number of rejections you get, the higher the number of ‘yes’s’ you’ll get. Rejection is a learning curve that forces us to look at why we got a ‘no’, and what we can do differently next time to get a ‘yes’.

A lot of the successful people I know are immune to rejection; they understand it’s a natural part of progression, so they accept that they must face rejection head on. In fact, there’s a popular TED talk, ‘What I Learned From 100 Days of Rejection’, that talks about how useful it can be to purposefully seek out rejection, every day, for something little — like asking to speak over a supermarket’s intercom — so you can build your immunity to hearing ‘no’.

As I’m becoming more immune to rejection, I’m becoming a stronger and more confident person. I get through rejection by remembering that it’s all a part of the journey, and that no-one won the first time. Maybe I didn’t win this time because of politics, or because I wasn’t good enough. I get through it by looking at it rationally, and never letting it stop me. I don’t let it get me down. Instead I analyse what we can learn from it — how we can do better next time — and I move on.  

Fear and self-doubt

Fear and self-doubt will always be around; there’s no magical way to remove them. It helps to remember that everyone experiences them, and the only way out is to push through. So many people are fearful they’ll lose their job. I know musicians who are fearful they won’t make it, and when they do make it they’re fearful they’ll lose it. I know millionaires who are fearful of losing their money and having to start again. I know billionaires who are fearful of things going horribly wrong and losing the majority of their wealth, along with their reputation. When I realised that some of the brightest sparks I know go through similar personal struggles, it helped me be less bothered by mine and face them head on.

But still, in the back of my mind there are those nagging questions that kindle my fears: How much money do we have? Can we pay our bills? Is that new customer going to sign? Is so-and-so going to do wrong by me? Am I staying healthy enough? Have I progressed far enough to meet my three-year goals? Can I really get there? Am I burning the candle at both ends? Am I disciplined? Are we training and developing the team enough? Do we have enough money to fuel growth? How is this contract going to go? Is this all real? Are we really going to get there or will I fall over? I have fears in my personal life as well. Am I being a great uncle to my nephews? Do I spend enough time with my family? Am I travelling too much and not spending enough time with my fiancée? Do I spend enough time with each close friend in my life? Fear and self-doubt can be all-consuming.

How to manage fear and self-doubt

I’ve come to peace with the fact that fear and self-doubt will always be there, so I manage them as best I can. When I feel fear or self-doubt rise up, the first thing I do is take away the intensity from the emotion. Becoming somewhat rational when I’m in an emotional state is something I’m constantly learning more about, and the more I do learn, the further I get. The fact is, when you’re feeling doubt or fear you can choose to let it take you down, or to empower you. You can’t be mellow with it; it’s either up or down. When it kicks in I remind myself that it’s just a part of the journey and I look at it with as little emotion as I can. ‘Okay, it’s happening. Can I deal with it or not?’ I dig deep, knowing that it will go away if I just keep going.

In a practical sense, I get through the fear by hedging my risks so I’m managing what could go wrong, and I get through the doubt by having great people around me who I can openly talk to about it. This is why it’s really crucial to have a great ecosystem of people to whom you can say, ‘Mate, I may look like a superstar leading the charge, but I’m feeling rubbish’. My chairman is like a father figure in my business. I’ve got a great relationship with my father. I have the most beautiful fiancée, and I’ve got other people close to me who put things in perspective. When I’m concerned about doing a multimillion-dollar deal and a friend tells me about problems they’re having with their children — maybe bullying at school — it snaps me out of it. It puts what I’m doing into perspective, and it all feels less terrifying.

Making sure I’ve had enough sleep always helps me, as well as keeping myself refreshed with habits and routines. I’m not a meditator in the sense of sitting still, but I leave things at home and go for a mountain bike ride. Moving my body breaks my emotional state, and there’s nothing like riding in the mountains with good people, legs pumping, breathing in the fresh mountain air; the trees are just as they were yesterday and last year — no matter my ups and downs, they’re a refreshing constant. This is how I keep method to the madness. You need to find the routine and habits that work for you.

The imposter syndrome

The imposter syndrome strikes almost every successful person. It’s the experience of feeling that your accomplishments are somehow not real, and that you’re a fraud who could be found out. I go through it a lot actually, thinking I’m a fraud and that somehow my achievements are fake, but it wasn’t until I saw fellow Australian, legend and entrepreneur Mike Cannon-Brookes discuss the imposter syndrome in his TED talk that I put a name to the feeling I’d had so often.

Mike has a great story! He began his company Atlassian with his best buddy, Scott, after finishing uni, and it now has a revenue of over $600 million, a market valuation of $15 billion and employs thousands of staff! For 15 years he had this feeling every day that he didn’t actually know what he was doing and that he would be found out — and he finally placed it as being imposter syndrome. It’s really common.

When I was 20 I set the goal to have a $20-plus million business by the time I was 30. When I was 27, OTG was valued at over $20 million. I was three years early. It’s crazy to think that in 2012 OTG was nothing but an idea! Is this all real? I remember later thinking, ‘Wow, wouldn’t it be great if one of the biggest companies in Australia wanted to work for us?’ And then I reached the point where we started doing deals with that company and I thought, ‘Imagine if I asked them for an investment?!’ And then I got to the point of doing that, and they were keen as mustard. ‘Holy shit’, I thought. ‘Is this real? Is someone going to tap me on the shoulder and say, “Just joking! Your time’s up, mate!”’

The thing that helps me the most with the imposter syndrome is having mentors who have already reached my goals. That way, rather than feeling weird because it doesn’t seem real, I have someone to validate my experience and say, ‘Yes it is real, I’ve done the same thing too’. They help me settle into the reality more comfortably — it’s important to have people around you who help make reality out of your dreams. Do you have these people? I’ve invested in a leadership team (my chairman and executives) who set the company’s objectives with me, and they help make it all feel real when we achieve our goals.

It’s also helpful to accept that feeling like an imposter happens, so don’t let it get to you. As ambitious people, we often set the bar so high that when we get there we can’t fathom that we’ve reached our goal. Take a moment to acknowledge what you’ve achieved — celebrate and ground yourself in the reality of your achievement. Go hang out with loved ones, feel the pride of making your goals happen. And then, set the next goal. My vision for 2022 is to take my company above $100 million. It’s been a calendar reminder for a few years, every single day at 8.00 am (obsessed much?!). Moving on to the next goal keeps me active and engaged, and means there’s not too much time to wallow in the feelings of being an imposter.

Give less fucks

At the end of the day, it’s important to remember that life is way too important and short to give a shit about most things. In five years’ time, will you really be worried and stressed about this? Keep your focus on the bigger picture, and give less fucks about everything else. Don’t let things upset you that aren’t worth your time, emotion or energy. Remind yourself that you’ll die one day, so there really is no time to worry and stress about the majority of things you’re worrying and stressing about. So, if in five years’ time you won’t care about something anymore, stop caring now.