1. What have you found most challenging as a leader?

Being a leader is fundamentally challenging as one has to subvert ones own needs and desires for the wider good. This means being accountable even when the mistakes aren't yours and lifting others up even when you yourself are down. Leadership is about showing up every day, even when you don't feel like it.

2. How did you become a leader? Can you please briefly tell the story?

I don't know that I would describe myself as a leader and even if others do, I am not sure that there was a linear path at the end of which I would have suddenly thought - "that's it, I'm a leader now".
But if I were to talk about some of the things that instilled leadership traits within me, it would be the response to moments of adversity in life. The most vivid one was when one of my warehouses burned down in Papua New Guinea.
I had just returned home to Melbourne after several weeks in PNG and got the call to tell me the factory was on fire. I was on a plane back up within the next 36 hours. I had to show strength even when the business was devastated, to show empathy to those members of staff that we had to let go, I had to fight with the insurers to make sure we got what was due to us - in short, I had to show up and show the path forward.
You don't become a leader by telling people what to do, you become one by showing them in what to do and how to do it in every action and situation you come across.

3. How do you structure your work days from waking up to going to sleep?

It has taken me a long time to work out how I work best. I am someone who works better later in the day, who is easily distracted, but who - when in a deep work flow - can get through an immense amount.
And over time, I realised that my mental and physical health help push me further.
So a typical day for me looks something like this:
Wake between 7 and 8 and after a shower including 30 seconds of ice cold water, I'll have two glasses of water and a decaf espresso and then stretch and head out for a run.
I'll run 5k most days, but anywhere between 3 and 10k depending on how I feel. Every day.
These days I try and do a bit of yoga when I get back but for the most part it's a good stretch before hitting the shower and starting my day proper.
I'm trying to get back into hand written journaling to explore my thoughts so I'll probably spend 30 minutes doing that unless I have something urgent that needs tackling.
I start taking calls from 10am most days, with CFOs that work with me, clients and other partners. Because I am less attuned to deep work in the morning, taking my calls then makes perfect sense, they require my attention but not the sort of focus that might be needed for something more complicated.
I'll typically have my first meal at 1300 but I never eat without having a run (and occasionally I may have to run a bit later in the day than I would like). I know that I have a tricky relationship with food so I try to aim for a salad with protein which is more than satisfying to keep me going during the afternoon.
I'll get back into work mode after 1400, and this might mean catching up on emails, doing some client work or deeper planning work - anything that requires focus and a lack of interruption.
I'll keep going as long as I need to, certainly through till 1800 if not beyond but always interspersed with short breaks to make sure I'm not burning out.
I may go for a 2 - 3k walk with my wife, which is an ideal moment for us to check in with each other and vent or celebrate as we might need to.
My evening meal is light and I spend the evening with my wife and two daughters, maybe watching a programme or two. Occasionally I might pick up the laptop again to finish off something I hadn't done or plan my next day out.
I'll normally be in bed by 2200 after a hot shower, and will spend a good hour or more reading, often fiction, but just as often something business related. I'll almost always feel when I'm ready to sleep and will
But what doesn't come across through all of this is that I am not particularly rigid about any of this. If I need to take a call in the afternoon I will, if I am low energy I'll listen to my body and take some time out.
I also record a podcast which means I have some days where I'll have 3 hours of recordings others with 1 and others still with none.
So I have to build flexibility into everything, to ensure I am on top of it all.
It's taken me 45 years to understand that this is how I work best - in my time and on my terms.

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

Because I am so heavily involved in finance, I am constantly reminded of the need for trust and transparency as a leader. Seeing the recent spate of business closures, failures and outright fraud in the startup ecosystem is painful to watch because often it has resulted from poor or non-existent leadership. A recent case was a startup that went insolvent around March but hadn't paid employees since September - no doubt leading them on with the promise of funding in the future. The reality is that you can only lead if you have people that believe in you and will follow you - that means that they trust you immensely and you have a duty not to break that trust. As a leader, your words, your actions are everything and when you abuse or lose trust, there is rarely coming back from that. So I am reminded of the absolute need for integrity and transparency, whatever the cost.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

I am guessing that I might be the first to recommend this, but I honestly believe that the book (or rather books) that had a massive impact on how I think about leadership were the Discworld fantasy series by the late Sir Terry Pratchett and specifically those that revolved around Commander Sam Vimes!

Why?

Because in the way that only Sir Terry could, we were drawn along the journey of a drunken has been, finding his self and his purpose and ultimately leading a force made up of different people, species and individuals.
And though the novels are clearly fiction, the messages are incredibly clear:
1. Be inclusive.
2. Be transparent.
3. Have integrity.
4. It's ok to make mistakes...
5. But you have to own them.
From a non-fiction standpoint, the most impactful book I read was The Hard Thing about Hard Things by Ben Horowitz.
It was a book that I read just when I was getting into the tech and venture ecosystem and, again, the things that I admired most about the story that Ben tells throughout the book is that there are no easy options and as a leader you have to do the hard things - always.

6. If you could only give one piece of advice to a young leader, what would you say to them?

I think the most valuable piece of advice I could give to anyone who is starting on a journey of leadership is to stay humble and to listen.
The worst kinds of leaders are the ones that drink their own Koolaid and believe their own hype, that stop listening to others because they think they know it all already.
There is always going to be someone more knowledgeable than you, more empathetic, more witty or smart, or just plain better - and you should take the good and ignore the bad.
You cannot be a great leader without a growth mindset so be prepared to get things wrong, the important thing is to learn from those mistakes and from others and move forward regardless.

7. What is one meaningful story that comes to mind from your time as a leader, so far?

I started building a technology startup in May 2021 after raising some capital.
By September 2022 we had pivoted the business and I was trying to raise additional cash but it became pretty clear that was going to be very difficult - I could blame it on the market, but the reality was we simply didn't have the traction to warrant getting additional funding.
I could have hidden this from my small team and tried to hoodwink them into continuing the journey with me.
Instead I was massively transparent, they knew how much money we had, how long it was going to last and that the likelihood was that there wouldn't be any 'new' money coming through unless we could do something immensely transformative.
They could all have quit. Then and there.
None of them did.
They continued to put their trust in me even despite the knowledge that in a few months they were likely going to be out of a job.
For me, that is the epitome, when you can lead people through adversity and know they have your back, whatever the cost.
It's massively humbling as well as inspirational that people will step up as long as you put your faith and trust in them.