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HOUSEKEEPING 📨

I am writing this from the plane as I head back to Australia after a few months back in my favorite part of the world, Latin America. Not too much I want to share today, really; I was taken aback somewhat, though, by a response from ChatGPT the other day. I asked a very straightforward question, to which ChatGPT began by responding, “Alright Doc—quick, clean, no wankery.”

I actually began to challenge myself after receiving this response. Do I speak like that? What does ChatGPT think of me? Am I a bogan? Anyway, not important, just something funny that I had to share with you all. Enjoy today’s piece. It’s a personal one. Back next week with more business and tech stories. Cheers!

BUILDING IN PUBLIC 🔎

Getting To Know Me: Sliding Doors

I am a founder. I am a writer. I am a deep thinker. But in the past, I have also been an athlete, a two-time expelled class clown, a smoker, and a party boy. We all wear masks and go through many different stages in life. What fascinates me, though, is the alternate realities, the ‘Bizarro Jerry’ versions of our own lives.

Opening one door closes the next. A random interaction in an elevator—who makes friends in an elevator—can end up in a life partner, or a co-founder in a new business. The decisions we make happen every day, consciously and subconsciously. It’s the sum total of these decisions that make us who we are.

Today, because for no other reason than I feel like it, I am going to run you through a number of decisions that shaped me. Big life decisions (and accidents) that changed the trajectory of the rest of my life. For better, and for worse. For good, and for ill. Here we go.

The Butterfly Effect

As well as being an IMDB 7.6/10 rated mid-2000s Ashton Kutcher thriller, the ‘Butterfly Effect’ is the idea that tiny actions can create massive, unpredictable consequences in the future. Coined by American meteorologist Edward Lorenz, the classic idea is that ‘A butterfly flaps its wings in Brazil … and a tornado hits Texas.’ Not because butterflies cause tornadoes, but because complex systems are insanely sensitive to small changes.

In the 1995 Simpsons episode ‘Treehouse of Horror V,’ we see Homer travel back in time using a toaster and keep making tiny changes that completely screw the future. First, Hime accidentally kills a mosquito. Later, he steps on bugs, moves a few objects, then teleports back to the current timeline, only to find a few things changed. Everyone speaks gibberish, humans are enslaved by giant insects, and Ned Flanders has become a totalitarian overlord. Oh, and of course, Homer’s worst nightmare of all: a world devoid of the one thing he desires most, donuts.

The world we see around is the result of such Butterfly Effects. Alexander Fleming went on vacation in 1928, leaving a bacterial culture uncovered. Mold spores drifted through his window, contaminated the dish, and killed the bacteria around it. He almost threw it away, but noticed something interesting. Voila, we got penicillin, saving an estimated 200 million lives.

In 1968, Lakeside School (an elite Seattle private school) used proceeds from a mothers' club rummage sale to buy computer time on a mainframe. This made it one of the only high schools in the world with computer access. Bill Gates was a 13-year-old student at Lakeside at the time. The greatest ‘what if’ of all, though, is the Vienna Academy of Fine Arts rejecting aspiring artist Adolf Hitler twice (1907-08). After said rejection, the butt-hurt Hitler spent years homeless in Vienna, developing virulent antisemitism. If accepted, he might have become a mediocre painter instead of joining the German Workers' Party. One unknown professor's assessment of his poor figure drawing may have indirectly shaped 70+ million WWII deaths.

Door #1: “Nottttttt”

The first flap of the butterfly’s wings for me was when I was in Grade 3 at Boneo Primary School. It was the end-of-the-year celebration, and my grade was in front of the school singing our own rendition of ‘We Wish You A Merry Christmas.’ The thing was, I happened to be standing on stage directly next to my friend, whom I was secretly head-over-heels in Grade 3 love with, Leah Smith.

I knew that I had an opportunity, and if I could think quickly enough, I could grasp that moment firmly and with two hands. But what was I to do? As I stood there looking side to side for an idea of how to impress Leah, I felt a cold bead of sweat run down my back. I was running out of time. As the lyrics rolled on like a freight train, the pressure built until the dreaded final lines were ringing in my ears. “We wish you a Merry Christmas, we wish you a Merry Christmas, we wish you a Merry Christmas … and a Happy New Year!”

And then it came to me. Just as the final syllable had passed our little eight-year-old lips, I knew what I had to do. I waited just the right amount of time between the song finishing and the round of applause from the feverishly proud parents, and I screamed one word: “Notttttttttttttttt.”

I still remember it to this day. A moment of stunned silence, and then the crowd went crazy. I think they admired the balls on this little pre-pubescent troublemaker. I looked to my right, and I saw Leah standing there, looking me right in my proud little eyes. She liked it.

It was from that moment on that I knew my destiny. I had walked through one of Jeff Bezos’ famous one-way doors, never to go back. Food and water were no longer what nourished me. I lived on a diet of laughter, attention, and adoration. For I was now the class clown.

Door #2: The house

I have written before, in a previous edition, about buying my first house at 19. A decision my dad forced on me, which, years later, I found out the rest of my family thought might be a little extreme for a kid of such a young age. The decision to buy a house changed my mindset entirely. While my friends were enjoying a $2,000 tax return win or stressing a $500 phone bill loss, I was dealing in wins and losses of tens and hundreds of thousands of dollars.

The decision by a) my dad and b) me to buy a house at 19 totally changed the way I viewed risk. Firstly, I had a much higher risk appetite from an early age, and secondly, I understood how to calculate risk relative to gain. I firmly believe that had I not taken the plunge on this house, there would be a future in which I haven’t travelled to 50+ countries, started multiple businesses, lived in countries where I couldn't speak the language, and more.

Door #3: Sickness + travel

Thanks to my newfound confidence as a budding real estate mogul, the first thing I did after my first home purchase and renovation was another home purchase and renovation, this time at 21 years of age. The next purchase came at 22, and if it weren’t for the Great Financial Crisis, I would have had the fourth shortly after. But it would all come to a screeching halt when I went through a terrible illness.

And that’s what I did. A quick Google of ‘best things to see before you die’ led me to the website of Howard Hillman’s 100 Wonders of the World. This became my bible. The next year, once healthy, I took off and began ticking off items on Hillman’s list. I kept one version in my travel diary for myself and another to give to someone else if the opportunity arose. I printed off and handed out dozens of them.

The alternate reality had I not traveled would certainly have been different. Fewer experiences, a shallower understanding of the world, etc., etc. But the bigger impact would be on my livelihood. Had I not had this experience, this newsletter would likely have been about the best real estate deals in Australia, not deep dives on business and tech. I do think, considering I had a million-dollar portfolio and hundreds of thousands in equity at 23, I’d likely have a $20 million dollar real estate portfolio today. That being said, if I had a magic wand, I would still take the sickness and traveling that led to the current version of me 100 out of 100 times.

Door #4: Steve Kennedy recommends

The next major sliding doors moment for me was when a friend of mine, Steve, recommended me for two jobs, which I was not even the slightest bit qualified for. The year was 2012 or 2013, and I had just returned from my last big backpacking trip of my 20s. Upon returning, I uprooted my current career (construction) and entered the fitness industry. Fast-forward 12 months or so, and I was coaching CrossFit and weightlifting with Steve in the daily afternoon classes.

After a trip to his 40th birthday in Bali, Indonesia (see above), Steve decided to nominate me to fill both the vacant head coach position at Bali’s first CrossFit gym—replacing my great friend Dave Driskell, who now runs APAC's largest CrossFit—along with a weightlifting coaching position at the training retreat, Ninja Camp. I had no business being in either position, but Steve believed in me, so his recommendation of me as “The best coach I’ve ever trained under” (he’d only had three coaches) was enough to get me flown over to Bali to interview, to which I was subsequently offered both roles.

The sliding doors moment was not that I moved to Bali, I didn’t. The moment came after I had completed my first fly-in stint with Ninja Camp. I told them that I had always planned to create an offering similar to theirs, which they told me “I should definitely do,” and that “I’d be great at it.” Being the bright-eyed and bushy-tailed naive go-getter I am, I did just that. I incorporated my first startup under the name AdventureFit Travel a week later and shared the news with them, including the bright and shiny logo.

I don’t hold any grudges against the stupid f*cks that ran Ninja Camp, but I do wonder what my life would have been like had I ended up in those roles. I’d no doubt have been living in Bali for at least half of the last decade of my life. And although that is a two-way reversible decision, I have seen many a soul get sucked into the Bali lifestyle never to return (no judgment).

Door #5: The backflip

The year was 2014, and I was in my CrossFit-is-cool phase, when my brother and I stumbled upon a YouTube clip of famed WOD-junkies Rich Froning and Dan Bailey being challenged to a workout by a couple of young gymnasts, which included handstands and backflips among the exercises.

Neither Rich nor Dan knew how to do backflips, but within five minutes, they went from amateurs to backflipping meatheads. It was at that moment that my brother and I looked at each other and decided we needed to learn how to do the same.

A week later, back at my parents’, I had fallen asleep on a nice summer’s day. I was woken from my slumber by an unfamiliar sound. Every 15 or 20 seconds, I would hear the sound. ‘Doompf … doompf … doompf.’ I was perplexed. ‘What is that sound, and where is it coming from?’ I thought. That was until I slowly peeled the curtains open and saw MY BROTHER IN THE BACKYARD DOING PERFECT BACKFLIPS!!

I was shocked. How could he do that? Could he be so impossibly athletic? My brotherly love swung towards a mix of admiration and jealousy. In my half-woken state, I was in no shape to head out onto the sandy patch of our backyard and challenge him. But I knew my time would come.

The following weekend, I found myself at a house party, with a large garage dancefloor. At some point, at around 11pm, I walked into the middle of the crowd and gave the signal for the party-goers to clear out and give me space. You know the one; the Moses-esque hand gestures as if you are parting the proverbial seas. It’s the universal ‘something big is coming’ sign.

As the dancefloor parted, I crouched down into my most powerful position, feet squarely beneath my hips for maximal force production … and I went for it. As I sprang into my first-ever backflip attempt, something didn’t feel quite right. The spilled liquor on the garage floor seemed to create a banana-peel-in-Mario Kart-like problem with my ascent. My right leg had slipped right out from under me, leading to much lower torque than I had hoped for, and an inertia to my flip that could only be described as devastating to my chances of success. Sure enough, as my head hit the concrete with the fury of a thousand suns, I knew that I’d failed. Then, darkness.

I woke up 24 hours later, strapped down to a hospital bed. I had hit my head so hard that I was out cold and immediately soiled myself right there in the middle of the dancefloor (yes, it happens). In the end, I was totally unconscious for 43 minutes. Long enough for the ambulance to call my parents to tell them I was suspected of brain damage and spinal injury. Don’t believe me? Ask ChatGPT.

What followed was six months of migraines, anxiety, depression, and catastrophism. The migraines subsided over time, but the anxiety and depression never really went away. My life is dictated by these two darknesses. It’s very bad, but I have learned to live with it. I wrote about how I manage things in my piece, The Ultimate Founder Mental Health Stack, but it's an ongoing battle.

I don’t want sympathy, though; I have friends and family who have taken their own lives, a number of those close to me taken by cancer or accidents. I am still here, and I am immensely curious. I do wish for, and wonder how much richer my life would be, if my hip explosiveness were just 20-30% higher (or if I had never watched that video).

Door #6: ‘Head of Culture at Zoox’

My final story is an opportunity that presented itself to me a couple of years into founding AdventureFit. I was still coaching at the time, and one of the guys in my midday class every day was Tim Kentley-Klay, one of Australia’s most interesting entrepreneurs. Tim had just founded Zoox, the autonomous taxi company that would later be acquired by Amazon for $1.2B.

The company was founded in 2014 and, by 2015, had raised funding from some of Silicon Valley’s biggest names. Tim, through the early years of Zoox, had been flying back and forth between Melbourne and the Valley, and at one point asked me if I’d like to join the company.

I didn’t understand why he wanted me to join or what the role would entail, but I agreed to meet Tim at Deadman Espresso, a famous South Melbourne coffee spot, on Boxing Day to discuss his plans. Tim told me at that coffee shop that he wanted me to be Head of Culture at Zoox, with an offer of stock (undisclosed at the time), $170k comp, a $25k international move budget, and he also told me that because we were friends, I had free use of the company jet (this is the part that I never really understood, maybe they rented one?).

I said no. And this would become another sliding door moment, one that would have likely ended with me entering the technology ecosystem much earlier, not as a founder, but as an employee. I’d likely have been at Zoox at their exit, making life-changing money in the offing. How different my life would be if I had just said yes to Tim that day at Deadman Espresso.

In sum

I wrote this post just so you could get to know me a little better. This newsletter to me is my baby, and I do try to put personality and love into it. But I also had wanted to write a piece like this for a very long time. I am fascinated by the choices we make; the doors we walk through, some of which will be closed to us forever. It makes me both sad and happy at the same time.

I was sitting once with my psychologist, crippled with fear of the future. I told him I had two options for approaching and couldn’t decide which to take. He told me to talk through the stories of how both would work out with him. Both of which ended with me saying the words, “And I’d probably live happily ever after.” And that is just that. We make millions of micro and macro decisions every day. But if you trust your gut and believe in yourself, the end should always take care of itself.

Extra reading

• The Ultimate Founder Mental Health Stack - August, 2024

• Getting To Know M3 - November, 2024

• Open Sourcing My Investment Portfolio - April, 2025

And that's it! You can follow me on Twitter and LinkedIn, and also don’t forget to check out Athyna while you’re at it.

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TOOLS WE RECOMMEND 🛠️

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