For my last blog in this series, I have chosen to write about my lessons from being an entrepreneur. For most of my working life, I have either started businesses or worked for myself. In many ways, everyone works for themselves, trading their time for money. The difference with an entrepreneur is that they do so without the security of a regular pay-cheque or the benefit of the potential upside of running one’s own business.

I don’t overestimate the security of a steady income. When I had my role as CEO at Turbo Recruit, part-owned by News Corp Australia, I got to feel what it was like to have a contract and a regular pay-cheque. There is little doubt that the security from regular employment is liberating. Knowing that one will be paid that week and not have to sell a job, convincing a buyer to get the opportunity to be paid, certainly makes for good night sleep.

However, a regular pay-cheque may also deprive a person of some of the pleasure made possible through an entrepreneurial career. Developing products or services, then convincing people that what you have is of value, negotiating the price, and then delivering the service connects one to their work in a truly unique way. Growing a business creates a different connection with one’s labour and the creation of meaning through work. Bringing people into the company and having them share the fruits of your success is a truly unique and rewarding experience. Expanding the business into different locations nationally and internationally gives one an immediate sense of making a mark on the world and seeing how capitalistic endeavours enrich many.

I know little of what it must take to grow a truly global business or a business that hires not 10’s but 100’s of people. However, I have had the opportunity to taste the experience of entrepreneurship as a small fish in a massive pond. I have learnt many lessons along the way, the most memorable I note below.

Lesson 1: Thinking about business is different from doing business

Many people are likely to think about owning their own business at one stage or another in their life. For some people, this might be a small local business. For others, their dream may be to grow a multinational company. Whatever the goal, however, most people will never make the leap and with good reason.

The doing of business is much different from what anyone imagines. Indeed, many people I have known will often say that if they knew the hardship of running a company, they would have never started the venture in the first place.

Business and entrepreneurship are not about having an idea. Having an idea is the easy bit, and ideas are a dime a dozen in many ways. Business is in the execution. For this reason, I’m often quite comfortable sharing my ideas with others. I know that some entrepreneurs are fearful of sharing ideas, but I don’t understand the problem. People, more often than not, will not do anything with the idea.

Moreover, even if they did execute the idea, it was not an idea that I was going to manifest. Otherwise, I would have put the idea into action already. Thus, better the idea is out in the universe doing good instead of locked in my head.

There are simply aspects of running your own business that preparation is invariably inadequate, and the idea is just the start of the process. An entrepreneur will have to weather macroeconomic forces from the global financial crisis through to COVID. An entrepreneur will have to deal with staffing issues, including potentially malice and incompetence. No longer are your issues your only concern. Decisions people make, quite rightly for their life, potentially have an immediate impact on your company. And let us not forget the competition. For every good idea that you have an investment in, many other entrepreneurs are doing a similar thing.

Lesson 2: Playing with your own money is a whole new ball game

In all areas of life, there are armchair critics, people who will provide advice from the safety of their armchair. Business is, however, very different from the inside. Every decision is a decision that carries an opportunity cost. Could those funds be spent better in another area of the business? Could those funds be spent better outside the company? Will this idea provide the profit that makes the risk worth the effort?

These questions have an edge to them when one must answer them with their own money. Every entrepreneur has skin in the game, and as quite rightly pointed out by Nassim Nicholas Taleb, having skin in the game changes the nature of the game and the game itself.

Entrepreneurs can’t simply walk away from their businesses like employees can walk away from jobs. Entrepreneurs are committed to their careers and, in many ways, forced to endure difficult times and revel in the good times. There is no getting off the ride.

Every entrepreneur has sunk costs, as the very nature of being an entrepreneur involves sunk costs. Those of us who have been fortunate enough to have successful businesses get a return for those sunk costs. Many others do not, and they go down with the ship. Most importantly, the ship is their ship and their money and every decision will count to either add or detract from their financial position.

Lesson 3: One of the best parts of being an entrepreneur is the company of other entrepreneurs

Many of my good friends are now entrepreneurs. These are people that I have to meet through business who share a familiar zest for living, risk-taking and accountability for their own life. These people want to enjoy the feeling of creating something from scratch and growing the entity. As discussed, there is a uniqueness to this type of person, and as a result, it is not uncommon for these people to find solace with each other. Early on in my entrepreneurial journey, I remember having regular drinks with my friend Bruce Duncan and building a bond over the trials and tribulations we experienced.

To Bruce, I could add many more entrepreneurs from around the world I consider friends, people I love nothing more than to share a beer and have a yarn with. Each person has their own war stories, trials and tribulations to share. Each makes for good dinner time company. Without a doubt, one of the greatest gifts of entrepreneurship is the friends that one makes along the journey.

Lesson 4: Entrepreneurship has its rewards

While entrepreneurship is not an easy road, a point I’m attempting to make abundantly clear. The life of an entrepreneur is also not without rewards. Many people toil at their jobs, and we all have the same 24 hours in a day. However, as an entrepreneur, one has the benefit of the opportunity. One is very unlikely to achieve financial freedom without taking the risk to become an entrepreneur.

While financial rewards are not the only reason people aspire to entrepreneurship, the rewards are certainly part of the motivation, and so they should be. Most countries are desperate for people to take the risk to start businesses, provide jobs, and increase the nation’s wealth. Given all the trials one is likely to face, the high rate of failure and the life commitment, aren’t the rewards justified? Ironically, I believe that money is not the driver for most entrepreneurs; the passion for the endevour is in their blood. That said, the money certainly does help.

Lesson 5: The entrepreneur life can be expansive

What I love most about being an entrepreneur is that it offers a type of life that is hard to get in any other way. As an entrepreneur, I have had the opportunity to work globally, delivering work across six continents (I have not yet had a gig in the Antarctic). I have lived across the globe, and my entrepreneurial background resulted in me getting handpicked for roles that would never have been the case had I taken a more conventional route to my working life.

I remember a lawyer friend commenting to me early on in my career how my career was likely to result in opportunities that he would envy. At the time, I thought little of it; I had not had said options at this point. Looking back, I see his words had a foresight that I now recognise. While my friend was eventually transferred to Auckland and became a partner in the legal firm, the point he made was that his career was local by its very nature. My career was different, and even during the height of COVID, I was somewhat unaffected, able to deliver my services virtually.

I feel a deep sense of gratitude for the life that has been afforded me by taking the entrepreneur’s route. I never take my good fortune for granted. The experienced life is all we have, and I’m grateful to have had the expansive existence offered to me as an entrepreneur.

I can’t say that I had some grand master plan to be an entrepreneur. If someone told me that I would still have an association with OPRA late into my 40’s as I write, some 25 years since starting the business, I would have said they are out of their mind. But 25 years on, I have the same passion for my career and running businesses as I did when I first had the vision for the company. Have I achieved everything that I would have liked? Certainly not, but the industry is still young! The lessons I have learnt from being an entrepreneur provide me with the platform for the next 25 years, and I look forward to experiencing new lessons as the journey continues.