When I was nine, I decided to be an entrepreneur. Back then, Mum was selling timeshare in Taupo, working for a round man with a red face, a big smile and rugged laugh. He told me how he'd started gyms and restaurants, and now a timeshare resort. I thought of all the businesses he had learned about, and the interesting people he’d met. He described himself as an ‘entrepreneur’. From then on, when people asked what I wanted to be when I grew up, I’d reply ‘an entrepreneur’.

I didn't realise it, but I already was one. I opened my first business at age seven, selling flowers outside the front of our house with a friend. Our garden was full of them. I cut some, set up a table on the footpath, and between us made up price cards ranging from 5 cents to 20 cents, with a sign advertising our enterprise. But we were on a busy road, and by the time people in cars saw us, they'd passed. For a whole day we didn't have one customer.

My chilhood

I asked Mum if she'd buy some balloons for us to display around our stall. Next day, we decorated our stand, and it worked! Car drivers saw us, stopped and bought flowers; by day's end, we'd sold out. I remember marching into the house and telling Mum we'd sold all our flowers - to the reply that I'd need to pay back the money she'd spent on the balloons. After that, we only had a very small profit, but I learnt some business concepts around marketing, profitability and most importantly – if I failed once, don’t give up.

At university, I was appalled to discover that my hometown of Wellington had one of the highest youth suicide rate in the world. It was something I felt young people should know, and an issue we should discuss and solve as a community. So, I organised an event to expose this hidden epidemic and put it on the political agenda, drawing attention to support organisations available to young people in the area.

For months, I felt it wouldn't come together: artists pulled out, helpers failed to follow through, and politicians tried to stop it because they thought that talking talk about suicide was bad. The costs kept piling up and I couldn't see how the whole thing would come together. I was terrified. Yet, I was so far in that I couldn’t back out.

The Levi's Life Festival did take place, drawing 15,000 young people to watch twelve of New Zealand's music artists perform across two stages. Compères included celebrities and high profile politicians who agreed that it was time to start addressing the issue, and the whole event was broadcast live, nationwide, on free-to-air TV. Here's some press about the event.

By then, I’d become interested in radio and noticed that one of the big companies, 'The Radio Network' had a frequency they weren't using. So, I developed a proposal to start a station on it. '9inety6dot1' would play alternative rock music for 16-30 year olds with an emphasis on local bands. We'd play no ads and fund the station with sponsors like Pepsi and Vodafone who'd buy day-parts. I didn't ask for any money but rather suggested that my (then non-existent) team and I would receive 20% commission on any income the station generated.

Rebekah's dream of saving lives

Within a couple of months we were an eager team of eight - all of whom signed up to work for free until we made money from sponsors, which we'd split equally. We ranged in age from 18 - 22 and none of us had much idea how to run anything let alone a radio station. We came up with crazy rouge competitions and promotions - some of which landed us in trouble - but our formula of fighting as an underdog and playing more ‘on the edge’ music and announcers worked.

A year later, I moved to Sydney and worked awhile with Grant Thomas Management - I'd met them at the Life Festival as they managed Neil Finn. Within three months, I’d taken on my own band 'george', then a little-known group from Brisbane. I released their EPs independently; with sales of around 20,000, these created an expanding street following. Then, after nearly two years, Festival Mushroom released george’s debut album, Polyserena. It debuted at Number One on the ARIA Chart, reaching Triple Platinum status and became one of the biggest sellers of 2002.

Fortuitously, I met Australian music industry legend John Woodruff at a bar in Cockle Bay when celebrating george’s number 1 album debut. John encouraged me to launch my own management company and offered support, a loan and a free office to help me get started.

Within a few weeks of establishing Scorpio Music, I discovered and signed my first client - three brothers from Feilding, New Zealand, aged fourteen to eighteen, playing under the name Evermore. In their early days, we toured relentlessly, building the kind of grassroots fan base that had helped launch george. In 2004, Evermore’s first album, Dreams, sold over 100,000 copies, and was nominated for five ARIA awards. It established both the band and Scorpio, which moved into its own premises.

Two years later, their second album, Real Life, sold 200,000 plus copies. Scorpio expanded, with an office in London and a co-management partnership in New York. It took on more artists, notably Matt Corby, Lisa Mitchell and Operator Please who have had considerable success in the UK, Europe and Japan. Scorpio Music became one of Australia’s largest music management companies, with a reputation for innovation, hard work and a high strike rate of hits.

Rebekah and Evermore

In 2011, while promoting a tour for Evermore, I hit a problem when ticket sales to the band’s Perth show flagged.  I decided to ask the band’s Perth fans if they’d become promoters of the show at school or university, offering to pay commissions for tickets sold. It worked. Evermore fans started putting up posters in school common rooms and university foyers and selling tickets to their friends.

The following year I launched an internet version of this. ‘Posse’ enabled bands to empower their fans to promote concerts online. The platform became an effective and measurable advertising channel for concerts. Fans earned commissions and felt like they were a part of the music business. I raised an initial round of Angel capital and began recruiting engineers.

18 months in it was clear the model was flawed. Although we had sold more than $2M in tickets, our cut was small, and the cost of onboarding clients (tours) was large. There were many stakeholders to win over: promoters, agents, venue owners, ticketing companies, artist management and the bands themselves. Worse, our clients (bands) all churned after eight weeks when their tour finished.

TED Sydney 2012 | Photo by JJ Halans

The sales cycle was just too expensive and the yield to us too small to ever be profitable.  We eventually sold Posse’s technology platform, community and some key team members to Future Music who still run the business under their own brand today.

In 2013, I tried again.  I reused the name ‘Posse’ which wasn’t part of the sale to Future Music, and launched a similar model for shops.  I developed a process to scale our engagement with small business owners and within 12 months, we had signed up 40,000 shop owners from around the world.  This time I had an effective scale and engagement loop but hadn’t worked out how to generate revenue.

In 2014, we merged Posse with Beat the Q and E Coffee Card to create Hey You.  In partnership with my co-founder from Beat the Q, we raised a $5M Series A funding round led by Reinventure (Westpac) and began to grow the combined business.  We recruited a small but brilliant Sydney-based team and I spent time in Manila building mobile app development and customer support teams.

Hey You has become the dominant mobile ordering and payment application in Australia.  We’ve grown by a factor of ten since we brought the businesses together in late 2014 and now process more than 20,000 paid mobile transactions every weekday.  We’ve integrated into the Westpac banking app and now continue to ride a wave of growth fuelled by the market trend of mobile payments.

Beat The Q Posse group raises $5 million

The Hey You brand mission is to make the city more human.  It personalises to the customer’s name when they open the app (“Hey Jill”, “Hey Jack”) and helps them learn the name of the people who work at their favourite café.  Hey You applies technology to help customers and café owners develop a personal connection with people they encounter every day.

My most significant life event was in February 2016 when I gave birth to my beautiful daughter Eve. The first few months of motherhood were challenging as I tried to emulate Marissa Mayer and return to work with baby in tow after just four weeks. You can read more about my experience here.

Becoming a mother made me evaluate my contribution to the world. I questioned if I was using my talents most effectively. I’d always thought ‘impact’ work would be in my future.

But the burden of launching a child into an uncertain world meant I was no longer able to procrastinate. Every night I’d lie awake frustrated, unable to justify that day’s achievements. Time to make a change.

Rebekah and babe Eve

In 2016 I joined the Innovation and Productivity Council to advise the NSW Government on the future of work in NSW. I identified a vacuum of career advice and information available to high school and university students. We all know the workforce is changing; what are the opportunities of the future? How should young people prepare?

In April 2017, I stepped into the unknown once again to try to solve this problem. I’ve spent months interviewing industry, students, parents and others. My co-founder and I plan to launch our Minimum Viable Product soon. Watch this space!

My passion is to support and inspire others to discover and reach their dreams. Imagine a world where all of our talent is deployed effectively, with no potential left behind.

My work is to achieve this both one-on-one and by using technology for scale. I run capital-raising workshops in Sydney, Melbourne and Brisbane to support entrepreneurs to launch their ideas. I love career coaching students and career changers one-on-one. Please contact me for further information