June 2026
(Based on a talk for an Angel Curious event)
“Goals aren’t enough. You need goals plus deadlines: goals big enough to get excited about and deadline to make you run. One isn’t much good without the other, but together they can be tremendous.”
– Ben Feldman
“If you think about it, angel investing is an amazing deal. You give a bit of cash to someone who will work the hardest they’ve ever worked in their life, for years, and if they can make it work, you make a lot of money.”
―Lenny Rachitsky
The Mission
I’m going to get Shakespearean with this whole thing. I think that the world doesn’t like change and also rewards momentum. Things that have been around for a long time and growing for a long time keep growing and keep winning. Companies that are dominant in a market stay dominant and because of their dominance, they determine how things work and how society runs. The only way I believe to really change the way a society or the world works is via startups.
Because startups are rockets and money is the fuel and when you capture money from customers, it creates this perpetual motion machine of growth which you can aim at an industry. The rocket ship is basically like harnessing technology and capitalism and hurtling it like wrecking balls travelling at a thousand miles an hour right at a vulnerable spot in a market that when it works changes everything about how that market works and how people do anything in that market.
Anytime you see something broken in the world or a process that can be improved, there is room right there for a new startup to come along and fix that problem. If you can harness that energy and force, you can enact change in the world. But the world itself tries its best to resist that change. Because you’re attacking dynasties and monopolies and oligopolies.
We use corporate language to describe this, product market fit, problem solution, business models. But I think it’s more mission driven than that. It’s entrenched power within a society and within a market that you’re going into battle with when you build a startup. And you do that because startups are the only way I believe that you can go to war with the universe and win. You can solve injustice and exploitation and do good in the world with some of the same tools that create it: capitalism and technology.
What does that mean? What does going to war with the universe and winning look like? It means helping millions of people, it means saving lives, it means changing your own life, it means making unbelievable amounts of money whilst also doing good in the world. Some of the beauty of it is you don’t necessarily know that you’re doing it while you’re doing it. Let’s use some examples. I will stick to my own portfolio and use some rarer unknown examples than popular ones that everyone knows.
When I built my first startup that eventually became Melbourne’s free tram zone, I had no idea how big it would get as I was doing it. Today, millions of people use it every week and the state government receives billions of dollars in revenue from it. Before it existed, homeless people couldn’t move to find shelter, people wouldn’t get medical help because they didn’t want to spent the $5 it would take to catch a tram. Coffees weren’t ordered, movies weren’t watched, friends and family weren’t seen because of the prohibitive effect on the velocity of capital caused by small cost barriers.
I am an angel investor in a company called WeMoney. They’re getting big now, on a unicorn track. But what they do is help people pay off their debts by automatically refinancing them to lower interest rate credit products. It’s magical, you log into WeMoney and all your loans and debt is automatically refinanced to lower rates and they underwrite the risk. In a world of predatory credit cards, gambling, car loans, pay day loans that exploit people, WeMoney is single handedly going to war with all of them and they’re winning.
They’re saying that trapping people in mountains of debt they can’t pay off is wrong and they’re fixing it. They’re emancipating millions of people from cycles of poverty and generational inequality by just doing something as simple as getting them out of debt quickly and then wrapping them in a circle of low rate credit such that the high rate credit can’t get to them anymore. They’re going to get big and they’re going to do more to lift people out of poverty than most charities will and they’re going to make a fortune doing it.
I am an angel investor in a company called Everlab. They’re also on a unicorn track. What they do is wholistic medical diagnostics built on the premise that doctors don’t actually do enough and they can make catastrophic errors. The whole medical system is reactive and it should actually be proactive. It’s really simple: a blood test, a bone scan, a genetics test and then a couple of doctor consults where they look for diseases you don’t know you have rather than you tell them what you already have.
They literally save peoples lives every single day. The bigger they get, the more people they will save and they will make a fortune doing it. They’re going head to head with the entire medical establishment. In fact, when the founder first told me about the idea I asked all my Doctor friends who said it was a terrible idea and that medicine didn’t work like that. So of course, you have to fund them. Whenever the establishment thinks something is bad, fund that company because frontier innovation looks scary to the status quo.
My Dad is one of those lives that were saved. He didn’t know that he was actually really sick, he had consumed a fatal amount of lead and had severe lead poisoning. In about 6 months time he was probably going to go into a coma and we’d just have no idea why. But he used Everlab and they called him and said go straight to hospital emergency, you are about to die with an acute fatal quantity of lead poisoning. That test and that phone call saved his life.
Most doctors don’t even bother to test for lead because of how rare it is. But if Everlab hadn’t, and I’d never invested in them, then my Dad wouldn’t be here anymore. The irony in this story is he had seen a doctor for a full workup just weeks beforehand and it was missed. The entire medical system failed him. But it was a startup that saved his life. I didn’t know it at the time but angel investing in Everlab, in addition to providing a venture return, directly lead to saving my Dad’s life. I didn’t know it when I did it but it was a way of taking back control from the universe.
I now have dozens of stories like this. Much of the venture world is the impact that you don’t know you can have until you’re having it. Being a founder and an angel is like being an agent of change and goodness in the world. That’s why everyone who has the money to should be an angel investor. You don’t know how much change and good you’re able to do until you are doing it. So much of the future upside is in unknown unknowns. There isn’t an amount of money I wouldn’t spend to save my Dad’s life and you can’t see that upside coming when you make the investment.
The Returns
There is almost nothing you can do in this world that can generate a 10X or 100X return within 10 years with any kind of reliability without doing much of the actual work. But that’s what really great angel investing represents. This is a power law industry and you can reliably generate power law returns.
Sometimes the returns can be even crazier and not be 100X but 1,000X. A really excellent angel investment can turn $1,000 into $1 million within a decade. The early Canva investors generated a 1,000X return. The early Xero investors generated 1,000X returns. The early Afterpay investors generated 1,000X returns. It is both exceedingly rare and also quite common to get this kind of outcome.
You can back companies that generate those types of returns and in Australia we are producing them at a rate that is some of the best in the world. People are generally surprised to learn that since 1990, a period of the last 35 years, Australia has produced 13 Decacorns and over 150 Unicorns. So consistently there’s a decacorn created every 3 years and a unicorn created every 3 months. That has held true for the better part of a quarter of a century.
Almost every decacorn produces those kinds of 1,000X returns and almost every unicorn produces a 10X to 100X return. This isn’t even including the 9 figure whales which can also generate venture returns. The opportunity is provably there, it’s just a picking problem. Can you pick which startups you’re looking at that will or won’t turn into the unicorns? The great companies are getting started all around you, it’s just can you pick them. Most of the time when angels flame out it’s because they’re not picking well.
Or they’re bringing main character energy to a field where they’re the side characters. Because the thing about angel investing is we’re the side characters supporting the entrepreneur on their hero’s journey. If this was Hercules by Disney, the entrepreneur is Hercules who starts as a mortal and learns how to battle gods.
While we play the role of Phil, the goat character who is a friend and coach. But actually, we get much of the same returns that the entrepreneur does but without actually having to fight the Hydras. Can you look at scrawny Hercules and picture them getting godlike strength and hurling lightning at Titans? Because that’s really all that great angel investing is.
Angels widen funnels and when you have more angels, it improves the aggregate outcome potential. If really great angels can improve your odds of success from 1% to 2%, still low probability, that doubles your chances of success and the number of successful startups. We can’t really help how big you win but we can definitely reduce your odds of failing and by default not failing is winning.
How much should you invest? Everyone has their own style but I like to do $10,000 investments at volume. I used to think it had to be a lot more than this but then I realized I’d rather have less money in each deal and do way more deals. I believe that everyone good at startups should have about 10% of their net worth in venture. It is both alpha generating and also is a way to give back to the startup world.
It’s high enough to build a portfolio and get the great deals and capture any upside but also low enough that if you miss them all and lose, it doesn’t destroy you financially. And you’d be surprised how low a cheque size founders will accept. I’ve backed companies that went on to become unicorns where the founders accepted $1,000 angel investments which is an amount that just about everyone can do.
It also used to be that you had to know all the founders and companies to do the deals. But then in the last 5 years we’ve had the birth of platform businesses like Aussie Angels and GXE and Ten13. Where you can immediately have more dealflow than you can handle and the exact same dealflow as some of the best practitioners at the craft of angel investing in the country. Being a small country, eventually everyone sees the same deals because there are relatively few capital sources.
That is pretty much angel investing in a nutshell.