Tech Leaders Reveal The Biggest Risks They Ever Took

It's safe to say you need to take a few risks in life to reap the rewards of success.

That's exactly what these entrepreneurs did to get ahead of the game and establish themselves as leaders in the tech community.

We spoke to senior figures from startups to hear memorable stories from their careers, learning how they put it all on the line to turn their passions into booming businesses.

Brought to you by Deakin University. Find out more about the Master of Information Technology Leadership course at Deakin University, a new kind of master’s degree where your experience counts.

Samuel Raciti is Taxify's Country Manager for Australia. In six years he’s gone from studying at The University of Queensland and working on the shop floor at Virgin Mobile to running one of the world’s fastest-growing ride-hailing services.

What’s the biggest risk you’ve taken in your career?

I had come across a job advertised for a company I’d never heard of based out of a country I could not even point to on a map. With half a mind that the job ad was an elaborate Russian scam, I reached out to the recruiter and inadvertently applied for the role of Country Manager for an Estonian rideshare startup called Taxify.

A whirlwind 48 hours later, that included three interviews and several data tasks, I became one of the founding team of Taxify Australia. At the time, the startup was on the verge of entering the local market so I was thrust into preparations without any real documentation as to what I had got myself into. Within six weeks we had launched the platform in Sydney and soon after in Melbourne, the company’s most successful launch globally to date.

Almost unknowingly I had scored myself a leading role at the world’s fastest-growing ride-hailing service, which now has more than 10 million users globally and a local rider and driver base that grows exponentially every week.

What was the driving force behind pursuing that opportunity?

After watching some recent interviews of Taxify’s founder and CEO, Markus Villig, I was very impressed by his vision for the company and him as a leader. During the interview process for the Australian Country Manager position, I had an instant connection with Jevgeni Beloussov, one of Taxify’s expansion managers, so getting to work closely with the two of them was key.

Beyond that, the opportunity to set up and scale one of the world's fastest growing rideshare companies in Australia to compete with international goliaths greatly appealed to me. I am a sucker for an underdog and love a good challenge!


Nathan Airey is co-founder of beauty and wellness booking platform Bookwell with Matt Dyer, having got his start as a tech entrepreneur with Takeaways.com.au and EatNow.

What’s the biggest risk you’ve taken in your career?

Stepping out on my own, and I’ve done it twice. The first time was the scariest — leaving my full-time job as a commodity trader to found my own startup, Takeaways.com.au — but also the most impactful.

While building the business I met Hezi Leibovich, who convinced me to join the EatNow team. I packed up my home in Brisbane and moved to Melbourne in the space of just one weekend. EatNow merged with Menulog, which was then acquired by Just Eat. Just like that, I was working with a big business again.

I could have stayed on but felt it was time to step out of my comfort zone, this time to take on the beauty industry. I co-founded bookwell.com.au to help make booking beauty treatments easy for consumers and provide digital platforms for salons in a sector notoriously slow to adapt to technology.

Each of these moves felt like a risk at the time but I’ve learnt so much more and progressed so much faster than I would have if I had stayed with the safe options, and of course, if I’d never stepped out on my own at all.

What was the driving force behind pursuing that opportunity?

I’d have to say, a sense of excitement. A traditional career has never interested me. I’ve always wanted the freedom to work on the things I wanted and to create something big. That’s meant looking for gaps in the market, staying one step ahead of the crowd, learning on the fly and adapting quickly in the ever-evolving world of tech.

I could have stayed on as a commodity trader or as operations manager of Menulog Group but in both instances it didn’t feel as exciting to me as stepping out on my own.


Anna Reeves is CEO of That Startup Show, Australia’s number one show about startup culture. She is also a business mentor and was recently nominated for a Techboard Community Leadership Award.

What’s the biggest risk you’ve taken in your career?

For all of us as founders, myself, Ahmed Salama and Sally Gatenby, That Startup Show started as a side hustle. We call it our accidental startup because we didn't plan to pursue it to the next level after the first season.

Pursuing our curiosity has been the single driver for us in deciding to take the risk to go all in. We kept going because people like Alan Jones our mentor and investor encouraged us, and the show had gained so much traction with its audience.

We felt important conversations about innovation and technology were sometimes being lost. For us, building companies and creating innovations for the future, and where we are headed for the next generation of leaders, are hugely important.

What was the driving force behind pursuing that opportunity?

Firstly, having sufficient funding behind the enterprise was a major decision in making it happen. With support from LaunchVic and the Australian Government and other supporters, we've been able to build a purpose-built studio for the production in the heart of the innovation hub in Melbourne.

It's also serving a bigger vision to forge a new path for content that inspires and also educates an audience. I think people like to learn and television is not always about simply being entertained for the sake of it.

We have bigger plans than simply one show, as we are driven by the desire to innovate in everything we do, so watch this space, there's more to come!


Ryan Hanly is CEO of Travello, the social network for travellers. He was head of PE at a Brisbane boys’ school before jumping into the tech world with co-founder Mark Cantoni.

What’s the biggest risk you’ve taken in your career?

Taking the plunge to leave a full-time, secure, reasonably well-paying job to start a startup, with no experience in travel and tech. We didn't even really know we were starting a startup. We just really liked the concept and thought we had to jump into it. Leaving that security was by far the biggest risk. I’m married with kids, I’m not a 21-year-old who can just have a crack at something and live off ramen noodles for months! I did have to provide, so every decision I made impacted my family as well.

Mark and I were big travellers and watched the rise of social networks in every other demographic except for travel, so we thought we’d jump in there and provide a solution. For us now, it’s scale time. That means moving into new regions and really starting to fine tune the operations and growing the community. We’ve got large aspirations of being a global travel brand over the next 12 months.

What was the driving force behind pursuing that opportunity?

The overwhelming belief that this was a good idea and could be something. I wouldn't have jumped into this unless I thought we could make a success of it. We were balancing up the risk and looking at the possible outcomes. The chance of getting that outcome is relatively low but I thought if we can crack this huge problem, there could be huge rewards. The driving force was this belief the concept could be something really big.


Greg Waldorf used to run online dating giant eHarmony. Now he’s CEO of Invoice2go and recently led the team on an unprecedented challenge of rebuilding the app from the ground up.

What’s the biggest risk you’ve taken in your career?

About a year ago, we were in a tough spot as a company. We had more than 250,000 customers who loved and depended on our app to run their business every day. But our code was never really built to support the rapid growth we had seen, or the quickly evolving needs of our customers. We needed to make the very difficult call to build new software behind the scenes, and to move everyone over to the new version.

Many tech companies have tried and failed. We knew if we failed we’d lose the hard-earned trust of our loyal customers who had been using our product for years. But we knew if we pulled it off, we’d be giving them an even better experience on the other side. As a leader, I had another big risk on my hands with regards to my team. I was essentially asking everyone to stop what they were doing, and to rebuild the engine of a plane that was already mid-flight.

We faced many tough questions and hiccups along the way. When we launched the new version of our app, it was far from an instant success. We learned quickly from our customers where we missed the mark. Everyone went into overdrive, working closely with our customers to quickly iterate, continue improving, and to ultimately deliver what we set out to do.

Now, we’re in the best possible position to serve our customers. Our platform is not only more reliable, but it means we can continue improving the experience.

What was the driving force behind pursuing that opportunity?

Invoice2go was originally built more than 10 years ago, much of it during our founder Chris Strode’s train commute to and from his full-time job, if you can believe it! It was built the way many startups are built, and not necessarily to support rapid growth.

For startups in their early stages, it’s hard to plan for that kind of growth. You’re typically just trying to get your idea off the ground. At this stage in our company journey, our technology was really the only thing holding us back from being able to offer the best possible experience for our customers, so we had to make a change. And to make that change, we had to prioritise it over everything else.

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