6 Profound Business Lessons From A Teacher Turned Entrepreneur

Last Update: 21st August 2018

Career Guidiance

Reading time: 14 Min

The Journey From Business Teacher to Master of Business Administration Student to Entrepreneur

From humble business teacher to a Master Business Administration (MBA) student to online real estate entrepreneur and CEO of a news media company, Charlie Gunningham has now had so much industry experience that he can see a pair headlights at the end of a tunnel before they even turn on.

Despite his innate skill, this was not how his first experience of entrepreneurship and the digital economy played out.

In 1999 after completing his Master Business Administration, Charlie felt so strongly about making a change in his life and the lives of others, that he left his safe and comfortable position as a Head of Commerce at Hale School, and decided to give business a go.

18 years later, Charlie has started and transformed numerous digital businesses.

He has been around long enough to witness the digital disruption of many industries, yet he is youthful enough to be leading the charge all the way from start ups to internationally based businesses.

Charlie leaves many clues to his success in his life’s story so far.

He proves that students/teachers and academics of all sorts have the power to impact industries and change the way that business is traditionally executed.


What I Learnt From My Time Spent With Charlie Gunningham 

There is a lot to learn from someone like Charlie. He exudes a passionate kind of confidence that makes you feel very confident in his work of leading organisations to victory.


Business Lesson #1 – Leap when you are most comfortable.

Charlie had moved around once or twice during his career, hopping from country to country to have a new challenge. It was when he moved to Australia and completed an MBA that he stopped and thought to himself, is teaching the only thing I want to do?

He has set his path towards becoming head of school, but perhaps there was something else?

A friend approached him with a business idea that he could resonate with and it was at this moment when Charlie ‘jumped off a ledge’, as he would say.


Business Lesson #2 -You Can Build A Business Around A Personal Frustration

Both Charlie and his friend (co-founder) were expats to Australia, and they were captured by the internet being a better way of helping home seekers.

When it came to claiming their dreams of home ownership they were frustrated by one thing; they were made to wait, every week, until Saturday to see the latest property listings because they would only appear in the Saturday paper. This was where the idea for aussiehome.com was born.

The online listing service became a pioneer in the real estate industry.


Business Lesson #3 – It’s Okay To Have A Side Business To Support Your Big Idea

What originally started as a technology based service for the masses would soon be faced with customer adoption challenges.

Real estate agents were slow to adopt listing their properties online when they had only ever been listing properties in the paper; hard to comprehend now, but it happened!

To counter this aussiehome.com provided an offline offering to compliment their online offering. They created a physical magazine that would allow their customers to place a higher value on their services, despite the fact that most of the value was made up online.

At one point of the business they were extremely strapped for cash, but due to their early entry into the dot com era they had built up expert knowledge of the working ways of web development – Yet another business and stream of income was born!


Business Lesson #4 – Sometimes It Just Takes Time To Build A Business

The journey for Aussiehome was 10 years. It took 18 months to become cash flow positive and it took 5 years before their patient investors had any return.


Business Lesson #5 (online media lesson) – It’s Service, Not Eyeballs.

A website used to be able to value itself effectively on the amount of traffic it could generate in any given month.

Now, due to the saturation of content, it is becoming more and more difficult to monetize eyeballs purely based on content.

Now, it is important to consider other ways of maximizing value for your audience. One way you can do this is by building a service around your audience’s needs.

The media company which Charlie became a CEO served local business professionals. They created a product that worked as a hybrid of LinkedIn and Google, linking news stories and executives to their brands.


Business Lesson #6 – Products Can Improve Retention

In today’s world, a subscription (‘software as a service’, or SaaS) business is a popular business model. However, it’s a tough road home and requires many years of persistence.

If you’ve got a product that stands behind your content this can prove to dramatically increase the value of your services.



Bonus Nuggets for Master Business Administration.


How did your Master Business Administration assist in your journey through entrepreneurship?

The MBA turned me from a teacher into an entrepreneur. I met my co-founder on the course, plus a few MBA professors became our early mentors and investors. It gave me the confidence to press forward, and the systemic thinking to sort out problems

How has your MBA differentiated you now?

Many people have Master Business Administrations these days. It is a nice string to my bow, especially due to the fact that I topped the whole business school. That is a nice thing to claim, and have on the resume’!

Where did education play a role in your business success?

Completely. One of my favourite sayings is that you have to ‘educate to sell’, especially in a new market. Education is the bedrock on business.


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