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HOUSEKEEPING 📨

Last week I made a very small political statement, followed by this poll as to whether you, reader, would allow me / like me to expand the scope of what I wrote about. The poll was pretty close to be fair, but it seems I have some leverage to do so. To those who voted for me to stay in my lane, don’t fret. I kinda feel like I might talk about a few current topics here and there, but I do plan to stay well with the realms of things I feel somewhat comfortable talking about; business, culture, Athyna, Game of Thrones, branding.

I was pleasantly surprised that I didn’t have a lot of unsubscribes, no spams, and only two people yelled at me in the replies. I’d count that as a win really.

And for today’s post, with all this talk of markets and investing and so on, I decided that since it’s been a little while since I ‘open sourced’ anything, I’d spend a few words open sourcing how I am investing today. I am a very small fry, but it will be good to share with you and I plan to ship an update at least once a year to keep me honest. Anyway, without further ado, here is today’s piece.

BUILDING IN PUBLIC 🔎

Open Sourcing My Investment Portfolio

I grew up firmly in the middle class, in the coastal suburbs of Australia. And when I was young, I saw one thing on a daily basis that I promised myself I would not have to live through: financial stress. My parents drifted apart rather quickly when I was growing up, but the one thing that crushed the vibes of our household on a daily basis was financial pressure.

We as a family had a successful business, multiple investment properties, but were ‘cash poor.’ All day, every day. Or at least, that’s what it felt like. So from a very young age I decided I wanted two things: a) the upper body musculature of Arnold Schwarzenegger, and b) no money stress.

As of today I am 92kg across 180cm of dad bod, at ~18% body fat, so it’s safe to say, I have work to do there. As for finances, I have a burgeoning investment portfolio across a few asset classes. And you could say I have somewhere between 1-3 businesses that are ‘working.’ In today’s piece I am going to tell you what those investments are, why I invested in them, and what my plan is for 2025 and beyond.

This is as much about putting myself on the hook to act as an intelligent investor as it is open sourcing some more of my life to you all. A two birds one stone act. Here goes.

My investing backstory

Firstly let me start by saying, I have never been a good saver. I was always a great maker though. My first business consisted of sneaking onto the Dunes Golf Course next door to my house to find balls, wash them, and sell them back to golfers.

My second business was to steal tech decks from the Woolworths at my bus stop, and sell them at a 33% discount to kids at school. Making money for me was something I have always been really good at. Even if it may have meant bending the rules towards criminality somewhat.

But for all my ‘never been a good saver of money’-ness, I was actually very successful as an investor from a very young age. My first foray’s into investing: real estate.

At 19 years old, I purchased my first house. A 3.5 bedroom house in a town outside of Melbourne, called Frankston. After 12-18 months of renovations at night every day of the week I was able to capture some equity which I rolled into a second house at 21, a subsequently a block of land at 22. Then eventually a fourth property at around 25 years old, an apartment in the Melbourne up and coming suburb of Thornbury (before / after).

_{*Below you can see the before and after kitchen photos from the final property I owned in Thornbury.}

The crazy thing was that by the age of 22 I had a net worth—if you take the equity I’d created in my portfolio—of over $200-300k. I was the Scrooge McDuck’s of my neighbourhood. But my life changed when I became ill at ~23 years of age. After a year long battle to get back to full health, I totally changed my priorities and began travelling.

I travelled to 50+ countries over the next four years. From climbing snow-capped peaks in the Bolivian Andes, to walking with lions in Zimbabwe and everything in between. Throughout this period I would go on to slowly sell down my investment portfolio to fund further travels, until I had absolutely nothing left but a bunch of memories, condensed into a few archived web pages. Would. Not. Change. It.

The dark ages

They say the night is darkest just before the dawn, but that also means that is lightest just before the dark. After my incredible years of travelling, I came back to Australia and fell butt first into my first startup, AdventureFit. We would take people all around the world on adventure holidays.

It was a great product, a wonderful experience, and a terrible business.

This was a period where I would rent out my room and sleep on my couch to keep the business alive. Also known as the maxing-out-personal-credit-cards-era. It was actually seriously bad. I would routinely have to shop for food for the week, knowing I had no money and that sometimes my card would allow me to go into debt in order to fulfil a purchase at the supermarket. This type of stress is something I would not wish upon my worst enemy. Financial stress like that is crippling, and I think it probably led to my anxiety and depression that I battle with to this day.

An added level of stress was of the actual business failing. Not so much that I would fail but that a number of people would pay for what they would hope to be a life changing holiday, only to be let down. The thing was, everyone that came on one of these trips did so for some sort of a reason. Recent divorce, been laid off in their role, coming back from an injury, or even a serious health scare. I’d seen it all.

And one of the most rewarding things in that business was the feeling I would get when people thanked me at the end of one of our trips. Aside from ego, and determination, it was the one fire that really kept me going with that business.

Side quest: Millions from sports betting

During the time I was growing AdventureFit, a buddy of mine came to me with an interesting side hustle. Unfortunately, it was in an area I altogether despised, which was sports betting. Fortunately, the system was to basically rob for the bookmakers. Think of me and my friends as Robin Hood and his merry men.

Less tights, but similar outcomes. Robbing from rich, fat cats of this grubby world, and giving to the poor—in this case, ourselves. The system, known as matched betting, is actually pretty well known in college dorms rooms around the world.

The system was pretty simple. We would set up new accounts from online bookmakers, receiving free bets from them in return. And then using a few simple formulas we would turn those free bets into cash. In oversimplified terms, thanks to the free bets, when we placed a wager, we would either win or break even. Sounds crazy right?

Well, it really worked. I remember being at a bar having a couple of afternoon drinks with a friend, and receiving a text from my partner saying; “Hey mate, we had a good day today, we ended $73k up.” The drinks were on me for the rest of the afternoon.

The money I made during this period was funnelled, in full, into AdventureFit, which was burning more money than likes of Fast during the 2021-2022 bonanza. I basically raised a seed round, funded from myself, and evaporated it all. AdventureFit would be wound down in 2019 to move onto what I do now at Athyna.

My portfolio today

Now, before I get started. Let me say that I am a very small fry. Had I stayed in the real estate investing game, I am sure I would be in a very different position. But I didn’t, so I am not. The money that I do have is from my founder salary, which is ~the average of a founder that is at Series A stage in size, funding, revenue etc. And this newsletter, which believe it or not, has made more than $100k in the last 12 months.

A core portfolio should be high growth, but lower risk. Think index ETFs. Whereas your satellite can be your risky bets. Maybe more along the lines of individual stocks, thematic ETFs, more bespoke indexes (it’s actually ‘indices’) around the world. For me, considering I have a handful of angel investments, I decided to add a third bucket, which I call speculative. Below you can see my target allocations, and where those allocations sit today.

As you can see I am pretty close to where I want to be. That’s been due to a lot of hard work over the last 12 months. I was way too heavily weighted in accelerators and VC funds—which I bucket as satellite—and way too underweight in my core. So that meant holding off on accelerator cohorts and angel bets for some time.

Now that I am where I want to more or less be, as my dry powder grows, I plan to start picking and choosing a handful of angel investments that come across my plate. And possibly even launch a syndicate through this newsletter. Here below is my full list of investments.

Let me quickly break these apart for you though, so that you can see each cohort stack together nice and clearly.

Core

As you can see, I consider my core only four investments, or three rather really. First is cash. I have a small stockpile of cash in my bank in case of a rainy day, or nuclear winter. I bank with Up (we interviewed the founder a while back), so saver rate there is 4.1%.

The next investment I have in my core investment is in my own company, Athyna, and our employee investment program. We build an internal program that allows employees (and founders) divert a portion of their salary to receive a 10% p/a return with us. Some of the team actually pulled money from their bank to invest. I heard of this as a strategy with Professor Scott Galloway, who uses this strategy with with Vox Media, who power his podcasts.

I wrote more about it here, but the TL;DR is that we can pay 10% to our team, in pre-tax earnings. Meaning the interest that they gain is equivalent to ~14% post-tax investing. And it works for Athyna because we still currently have a little bit of debt at 17%, and only recently turned profitable so boosting cash reserves really suited us at the rate of 10%.

Satellite

Next we have my satellite portfolio. This part of my portfolio is what I consider higher risk, but I would exactly call it speculative. And it’s more than likely that—with very low risk—it outperforms my core portfolio over the next decade. If it looks concentrated in a couple of places, that’s because well, yeah, it is! Those two places are Australia & New Zealand’s greatest VC fund, Blackbird (also interviewed the founder). And their sister company, Startmate (and where I also interviewed the CEO), the region’s leading startup accelerator.

Blackbird had recently raised the very first billion dollar fund out of ANZ, and I was lucky enough to be invited to invest by a friend who is one of the general partners in the fund. I invested equally into the core (new investments) and follow on funds. Blackbird’s IRR (Internal Rate of Return) since inception is top quartile worldwide, and I believe still top quartile if you remove their darling investment, which was Canva.

As for Startmate, I’ve invested in multiple cohorts of the accelerator. Startmate, in order to mentor in the accelerator, require that you invest. So that you have skin in the game. They also have a world class IRR, better than most of the famed funds out of the U.S. I am also an investor in their follow on fund, which invests strategically into only the best performing startups in their next rounds as they scale. I also have extra carry in a few of the cohorts due to being either the top ranked (#1) or top-5 ranked mentor, voted by the cohorts.

Lastly, I invest in the Argentina ETF out of my satellite investment. I’ve lived in Argentina for 3-years now, and if there is one country I am backing in over the next 20, it’s Argentina. The people are incredibly hungry, driven, and smart. And now they have Milei at the helm. So long as he quits pumping shitcoins on Twitter, I think he is the right man to lead them to a better place.

Speculative

And then it comes to my speculative class of investing. The class of investing that allowed me to punt on ApeCoin, doubling my money on it’s launch in 2022. Since moving on from ApeCoin (sold my holding at a healthy profit), this cohort of my investments totals just under 10% of my holdings, and is reserved for angel bets and Bitcoin, of which I hold very few sats.

Some fun notes on my speculative holdings include my investment into Humane, a startup no one understood. Humane was a replacement of the phone, but punters couldn’t get their head out of the whole ‘Why do I want to carry a second device everywhere with me’ mindset. I actually think if they did their product launch less absurdly badly, the world would have really gotten it.

The highlight of my very few angel investments, is in beehiiv, that platform I used to send you this email. The last post we shipped was actually written by their founder, Tyler. I think beehiiv will be a truly generational company. Kiki and Atomic8 are struggling, Future Super doing fine. I like Future Super. Ethical investing. My kind of stuff.

And what might be my portfolio tomorrow

I have some big decisions to make with my portfolio going forward. Blackbird are raising their next fund, and the minimum is $250k, which is a big step up from my investment in the last fund. I am moving back to Australia in 3-weeks, and that means I’ll likely start mentoring at Startmate again, which means two investments per year per cohort. (When will it ever end!, jokes)

But I do also really love the idea of investing with you, dear reader, in an Open Source CEO syndicate. If I follow through with all of these investments, then a very large portion of my investing will be to the middle of the stack—the satellite portfolio. Which is fine, but maybe not what I want. Liquidity is good after all.

_{*Note: There is no context here for this image of Smaug, sitting smugly on his pile of gold in the Lonely Mountain.}

The other thing that is on my mind is Trump. I expect the world to get a lot more volatile over the next four years. Not so much that I worry about my investment tanking—which I do—but more so that I feel like the world is a tinderbox right now. And something tells me things are about to get a lot worse. Geopolitically speaking. With this in the back of my mind, my subconscious is screaming at me to pull everything out of everywhere, and buy a house—or as much of a house as that would get me—build a bomb shelter and hope for the best.

A pulse check, and goodbye

One thing that would help me decide is to keep gauging if we have enough interest in the community to actually build a syndicate out of this newsletter. The audience here is filled with the best founders, investors, and leaders in tech. And I can now get my hands on pretty great early (and/or late) stage deal flow. So let me ask you, the audience, again.

Anyway, that’s it from me team. I hope you enjoy snooping through my personal receipts. It was a fun one for me to lay out actually, and something that I plan to keep you updated on over time. If you enjoyed this post, let me know by sending a reply. Thanks for reading, and have a good one!

Fun facts

• My earliest illegal hustle: My first ever shady dealing was when I would collude with a friend who worked in the canteen at school. I would buy lunch, give him $2 in change, and would give me $20 in change. It was a great business.

• The first album I purchased: With my proceeds from my first hustle of cleaning golf balls, I was able to save up and purchase my first ever album, The Presidents of the United States of America (self titled).

Extra reading

• The Ultimate Founder Mental Health Stack - August, 2024

• Open Sourcing My Content Diet - October, 2024

• How (This & Other) Newsletters Make Money - November, 2024

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.

HIRING ZONE 👀 

Today we are highlighting AI talent available through, Athyna. If you are looking for the best bespoke tech talent, these stars are ready to work with you—today! Reach out here if we can make an introduction to these talents and get $1,000 discount on behalf of us.

BRAIN FOOD (KINDA) 🧠 

TWEETS OF THE WEEK 🐣 

ASK ME ANYTHING 🗣

I want to be a trusted resource for you. If you think anything I know in relation to brand, culture, global teams, sales and growth would help you unblock a problem in your weeks shoot me a line.

Ask in the comments or reply to this email and I will do my best to answer it in a future edition. 🙌🏼

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