I lived my twenties and a good part of my thirties with my foot to the floor. I believed that success would come from hard work and tenacity. The harder I pushed the accelerator, the faster I’d win.
It all started in my twentieth year. I convinced Neil Finn to play at a gig I’d organised to raise awareness of Youth Suicide in New Zealand. The event attracted 15,000 people, was broadcast on live on TV1 and led to a national conversation about youth mental health. What I took from the experience was a deep sense of self belief: “With hard work, I can make things happen.” I thought.
One year later, I finished my university degree and moved to Sydney. I took a job as an assistant to Neil Finn’s manager but quickly discovered that I wasn’t cut out to be an employee. I had too many ideas; I wanted everything to happen now.
In 2002, at age 24, Australian music legend John Woodruff (Savage Garden, The Angels) seemed to think I had talent: he offered me a loan and a free office to start my own music label. I named my company Scorpio Music and we became one of the largest independent music companies in Australia, launching the careers of Evermore, George (Katie Noonan), Matt Corby, Lisa Mitchell, Van She and several other top selling artists. I zipped about the globe like a disorientated dragonfly establishing offices in New York and a joint venture in London. Scorpio Music sold more than two million records, pioneered new business models for online distribution and merchandise and I provided consulting and A&R services to Warner Music.
And then out of nowhere, I found myself crouched down in the corner of a backstage tent at the Big Day Out in Melbourne. The tears wouldn’t stop.
The band I represented – Operator Please – were in full flight on the main stage, a crowd of 30,000 screamed and cheered, but I couldn’t watch. I felt overwhelmed with the sensation of living someone else’s life, following a passion that wasn’t my own. Someone else would be thrilled to be here. I’m in their spot. But I had artists to manage, offices to maintain, staff to pay. My stomach twisted solid. I’m stuck.
What followed was a ten-year mission to find my place in the world.
The obvious career shift was from music into tech. In 2010 I rushed (in hindsight much too fast) into starting Posse.com, an online platform to reward people for sharing music and gig recommendations. I learned about venture capital and raised $1.5M in funding. I hired a small team and we quickly pivoted the business to recommendations for cafes and restaurants.
In 2014, I led a merger of Posse with Sydney start-up ‘Beat The Q’. Together, we formed ‘Hey You’ which is now the largest mobile payments platform for cafes and restaurants in Australia. ‘Hey You’ is used by half a million customers, processes more than 100,000 transactions per week, employs a team of energetic and smart people in the Sydney CBD, and is largely owned by Westpac Bank through their Reinventure fund.
In 2012, I started writing about my experiences and what I’d learnt each week, often enlisting other business leaders and academics for advice. My blog gathered tens of thousands of readers from all over the world and won Smart Company’s ‘Best Business Blog’ in 2013 and 2014. I began writing a fortnightly column for The New York Times and a monthly column in the AFR’s BOSS Magazine.
For me, the experience of founding a tech company has been like threading my whole body through an old-fashioned clothes wringer machine. The process has shown up and squeezed out a lot (never all) of my weaknesses and I’ve grown in ways I couldn’t have imagined on the other side.
In a practical sense, I’ve now raised more than $17M in funding, won significant grants, led a tech team, scaled a salesforce, built a second offshore team in Manila, developed multiple brands, digital and on-ground marketing strategies.
But there have been crashes – it’s impossible not to when you’re driving with one pedal. I made poor decisions, fell out with a cofounder, broke a friendship, made hiring mistakes, leadership mistakes, pivoted too fast, pivoted too slow, wasted money when I should have saved, saved when I should have spent and so on.
I discovered that driving fast with the accelerator pedal down is pointless without two hands planted firmly on the steering wheel.
There are two controls that count: integrity and accelerator. The integrity lever is the steering wheel: it’s about looking deep inside at who you are, what you’re good at and what you’re meant to be doing here. For some people this comes naturally. They’ll live their whole lives following a deeply held vision, always clear what they’re here to do. For others, like me, steering myself is a process of constant reflection, trial, error and iterative course correction.
Then there’s the accelerator. How hard are you willing to push? The most successful people I know live in complete alignment with who they are, they’re clear, focussed on what they want to achieve, and they work incredibly hard.
In 2018, I launched a series of online and face-to-face courses, some led by me and others with leaders from high growth companies including Canva, Atlassian, TEDx Sydney, Google, Koala and more. My mission was to help share the insights from the world’s best minds. In 2020, Covid put a stop to our face-to-face programs (the majority of our business) and I had to re-think my plan.
I’d always wanted to write a book. Mum recently gave me a trunk of my school exercise books along with countless ‘novels’ that I’d started then given up on. As Covid forced me to pause my business activities I decided to focus finishing the project I’d started a year earlier – the story of my search for love.
Download the first five chapters for free here.
I also teach a dating a relationships online course.
If you’d like to learn more about what I’m up to each week then please subscribe to my newsletter below and I’ll send you my latest articles as I write them.
Thanks so much for your interest in my story and I hope you find some of my content useful.