Q - First of all, can you tell us a little about yourself, your career so far, and what you do now?
A - In university I studied business, marketing and hospitality. During university, I was working at a boutique hotel in Darlinghurst and saw a position on the UNSW jobs board for an internship working with Australian sporting greats like Greg Norman and Steve Waugh. I applied for the internship and it turned out that it was for a role at Macquarie Bank in the Leisure Investment Banking Team (at the time they were acquiring hotels, theme parks, marinas and other leisure-based assets). This internship turned into a 5-year stint working in real estate investment banking.
In 2009, I left Macquarie and wanted to do something different. I was watching a lot of the show Entourage and thought Ari Gold was pretty cool, so I wanted to be a talent agent. I applied to a bunch of firms in Australia and was super lucky to be given a chance by Chic Management (one of Australia’s top model representation agencies) and in particular by Ursula Hufnagl (the founder of Chic) and Jane Weston who ran Chic’s Celebrity division.
Working at Chic, I stuck out like a sore thumb and when the co-owner of the agency Peter O’Connell popped his head in, he was looking for someone to help him scale new business ventures. We tried lots of ideas including a "twitter for models" product called Model Feed, a "search for a supermodel" platform, and an oil and gas investment fund, but the idea that really stuck was a "low cost, online-only mobile network" called Amaysim. The idea for Amaysim started from the offices of Chic and I think is now the no. 4 mobile brand in Australia.
After being part of the launch of Amaysim, in 2011, Jono (my uni mate who joined Amaysim early) and I were looking for new opportunities. I was moving at the time and asked a friend to help me move, which begged the question: "Why do we ask friends and family to help with all these types of local jobs that people would love to do to earn some extra money?" This spark of an idea led to launching Airtasker, and building this company has been my personal mission ever since.
Q - What were some of the biggest challenges you faced in the early days of Airtasker, and how did you overcome them?
A - For the first 7 years of building Airtasker, our focus was entirely on growth. We raised a round of funding, invested that capital to grow the business, and then repeated the cycle—each time with a bigger round of funding and a higher valuation.
In 2019, we weren’t able to raise a fresh round of capital, so we basically had to get profitable fast. Thankfully, I had a great team around me and—by taking some decisive and hard measures—we were able to turn Airtasker from a $20m+ burn rate to cashflow positive in 9 months.
What I learned is that it’s super important to be decisive and make hard decisions: in general, growth is much easier than getting profitable. It’s fun and motivating to be scaling and investing more—it’s hard and not fun to have to manage costs and really prioritize investments!
Now, when I’m making decisions I’m often thinking: "What will future Tim think about the decisions that present-day Tim is making?" In other words, make the hard decisions today to avoid having to make even harder decisions later!
Q - Can you share a pivotal moment in your career that significantly impacted your leadership style or approach?
A - Raising our first round of capital to start Airtasker was certainly uncomfortable. Being responsible for deploying a 7-figure cheque is kind of gnarly when you’re young and inexperienced...
When we were raising the capital, we were probably pretty fueled with some type of adrenaline, and the enormity of the task ahead only hits you when the raise is done and it’s time to get to work. That said, the responsibility of raising outside capital definitely became a source of motivation to carry through and get the job done—we knew that we would not go back to investors without sweating extremely hard and giving the opportunity 100%!
Q - How do you approach personal growth and continuous learning, and what resources have been most influential for you?
A - For me, personal growth is all about staying curious, being introspective, and surrounding yourself with people and ideas that challenge the way we think.
In terms of resources, I personally learn the most from reading long-form books in paper—for me, this medium allows for greater depth and forces me to actually cognitively engage harder (versus say podcasts or audiobooks). Some of the books that have really shaped my mind are:
- Thinking, Fast and Slow
- Thinking in Bets
- Why We Sleep
- The Righteous Mind
- Good Strategy, Bad Strategy
Q - How do you cultivate a growth-oriented culture within your team at Airtasker?
A - At Airtasker, we’ve always believed that when our team grows, the business grows. So cultivating a growth-oriented culture is something we’ve been really intentional about from day one.
First, we try to create an environment where it's safe to take risks and make mistakes. We encourage experimentation, celebrate learnings—not just wins—and make sure feedback is part of our everyday conversations.
We also invest in personal development, whether through structured learning budgets, mentorship programs, or giving people stretch opportunities. It’s not about ticking boxes—it’s about aligning each person’s growth with what they’re passionate about.
And finally, as a leadership team, we stay open and humble and are always learning ourselves. When people see their leaders growing, asking questions, and evolving, it sets the tone that growth is part of who we are as a company.
Q - What strategies do you use to maintain focus and resilience during challenging times?
A - One key strategy for me is zooming out and trying to be super intentional about caring about what really matters. When things get tough, it’s easy to get caught in the weeds or feel overwhelmed by the day-to-day. Taking a step back to remember the bigger picture—why we started, who we’re helping, and the progress we’ve made—helps put some of the day-to-day crap into perspective.
On a personal level, I’ve found that simple routines make a big difference—sleeping well, regular exercise, taking breaks, and carving out time for reflection. That said, I do have an 18-month-old kid so I must admit that some of this personal stuff has been compromised—so I’m somewhat living on my daughter’s schedule at the moment!
Q - How important is a growth mindset to success, and how do you foster this mindset in your team?
A - A growth mindset is super important to success—especially in startups, where things are constantly changing and you're often building the plane in mid-air. In all areas of building a business: being willing to try lots of things, fail (or ideally succeed) fast, and seeing setbacks as opportunities is what keeps you moving forward.
One thing I wish I’d embraced earlier is the genuine gift of feedback. Early on, I probably spent too much time trying to "do things correctly" before shipping things. But in reality, nothing beats getting something out there, learning from real users or real-world responses, and iterating quickly. I’ve since learned that progress beats perfection.
Q - What are some key lessons you've learned about leadership that you wish you knew earlier in your career?
A - 1. What leadership hat are you wearing? The idea that there are different types of leadership—from "highly collaborative" to "command and control"—and that each can be useful in different situations was powerful. My coach would often prompt me to be intentional and think about which hat I was wearing in a particular situation.
2. What would your future self say about the decision you’re making today? It’s common that we make decisions today which are "kicking the can down the road" and avoiding hard decisions that create bigger problems for ourselves later. The framing of imagining your future self and making sure that your future self would "approve" of the decision that you’re making today has been very helpful for me to force hard decisions.
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