I've got a confession to make - I'm a bit of a weirdo when it comes to books. 

Since my early twenties, I’ve read a book almost every week. 

I highlight the lessons that resonate with me and rewrite them in little notebooks to keep them top of mind. This method works for me. 

The summaries of the books on this list have continually shaped my mindset and have helped me in my work, my family and my life.

But when people ask me for recommendations - I’m cautious. Because here’s the thing.

Most books are 300 pages reiterating one or two big ideas that really matter. 

I want to save you that time and share with you 12 books that changed my life and the one big idea from each that really stayed with me.

I like learning and writing on all things people, business, money, and mindset. So we’re going to hit the big ideas in these areas.

Okay, let's dive in with the most important one - People.

People

Peopleware by Tom DeMarco

I first started managing people in my late twenties and made many mistakes. One mistake really hurt the company I was working at. 

We were moving into a new office, and I was responsible for the seating plan. 

Big deal, right? Well, if you’ve ever planned a wedding, you know that the seating plan is a big deal.

I worked out the seating plan and thought everything was fine, but after the employees moved to the new office, the productivity of the engineering team plummeted. 

Our lead engineer, Jimmy, told me the environment was killing their productivity. I had put them too close to the sales teams that are loud and energetic. 

The decline in productivity was my fault.

This taught me to focus not just on quantifiable data like hours worked or products shipped but also on how people feel about their environment and co-workers. 

People's emotions drive their behaviour. The big concept from Peopleware is about change management.

You start in the status quo, then enter the “Chaos State” when changes occur, and eventually, you reach a higher status quo. Understanding and managing this transition is crucial.

We ended up buying all the engineers noise-cancelling headphones, and after a couple of weeks, things were even better.

And it really takes a completely different level of understanding to bring empathy and leadership to keep a team productive and successful. 

Even when I meet people, I shouldn't assume the meeting is a transactional business meeting; there's always some emotional connection we can make.

And the last book on people has the biggest idea that I’ve seen over and over again in my life but never recognized what it was.

Thinking in Systems by Donella Meadows

So before we get to the big idea in this book, there are three really important concepts to define on the spectrum of difficulty:

• Easy - tea bag + hot water = Tea. Easy.
• Complicated - is like going to the Moon. There's a lot of moving pieces, but it's repeatable.
• Complex - is when you can put in the same inputs and get completely different outputs. The best example of this is raising children. Me and my brother are like chalk and cheese on some things.

Why this book hit me so hard is that most people and businesses are just that - complex. And so much of this complexity impacts our happiness.

In systems, the author maps out a super helpful and visual framework for thinking about them. 

I’m from Sydney, Australia. We have tons of traffic. Now you can imagine Sydney's traffic as a system.

The inflow is the rush of cars, buses, and pedestrians entering this complex network, eager to move from point A to B. 

The stock represents the roads, highways, and traffic lights designed to channel this flow efficiently. The outflow is the successful exit as people reach their destinations. 

This cycle appears straightforward, but what happens when we introduce changes in the inflow or outflow, or how the stock moves? 

For example, a new construction project shifts the behaviour of the flow, creating alternative routes that alleviate congestion somewhere but create it elsewhere.

The point here is that while you can understand the components, you can’t really predict the overall system's behaviour with much accuracy when you change stuff. 

Every person we meet is their own system - when we change our work, our environment, our diet - anything. You should expect the system to change.

I’ve really learned to view people like organic systems and avoid treating anyone like a robot or a fixed process, especially in a work environment. 

People are not lines in a spreadsheet.

How to Be an Adult by David Richo

Now I don't know if I lived a sheltered life, but this book was actually the first time I really understood the hero's journey. 

The basic concept is a story of transformation, one which starts with a call to adventure, meeting a mentor, crossing thresholds, entering new territories, facing big challenges, and then going home, transformed by the experience.

Everyone's on their own hero's journey. You're on one right now. And it's the most repeatable playbook you see in lots of adventure movies. 

It's the story of how:

1. Luke Skywalker meets Obi-Wan, discovers the Force, and blows up the Death Star.
2. How Frodo meets Gandalf, destroys the ring, and goes back to the Shire.
3. Neo meets Morpheus, takes the red pill, and defeats Agent Smith.

But listen to this: in all these stories, there is that moment where the main person is going through the darkness, and you're like, “Oh no, he's not going to make it.” 

The author of this book, David Richo, captures it perfectly: 

Trust that darkness always precedes rapid self-growth. 

Time and time again in my life, the biggest breakthroughs come after the worst events, and often nowhere is this more true than in business.

Business

Growing a Business by Paul Hawken

In 2016, I started my first real company, and there was this podcast I listened to every day on my way to the office called Seeking Wisdom. 

The host recommended this book that I had never heard of. 

I'm actually surprised it doesn’t show up on many best sellers lists because the lessons here are timeless.

The most impactful one I got from this book was appreciating that the goal of business is never-ending growth. 

Because in business and life:

1. You set goals
2. Then you run into problems
3. Then you design solutions to solve them
4. Then you solve those problems
5. You update your goals
6. Then you run into your next set of problems. 

Over and over and over again, for years and decades.

And at the end of it, you end up on the top of the mountain of all the problems you’ve solved instead of under the problems you ignored or avoided.

How to Get Rich by Felix Dennis

No other business book I’ve read has made this more entertaining and raw about these problems than How to Get Rich by Felix Dennis. 

This is another book you find off the main track, and Forbes nailed it when they called it an unexpected gem.

How to Get Rich is focused on the harsh reality that business is ugly and messy. 

It has a lot of controversial and sometimes off-putting views, but the most impactful thing for me from this book was understanding Felix's view on iteration.

One of the chapters is called "evolve or die."

During the rise of the internet, many publishers got smoked by online distribution, but Felix was quick to recognize the impact of digital media and was one of the first to include digital versions of his publications. 

The meaning here is to always approach things with an open mind.

At the end of his life, after he had climbed the summit of success, he retired to paint and write poems. He ends the book with,

“You are already rich; not a lot changes... eating is about as good as it gets.”

The Almanack of Naval Ravikant by Eric Jorgenson

One of the huge themes in Felix's book is thinking on a big scale, and this foundational lesson to success is captured perfectly in The Almanack of Naval Ravikant. 

Okay, so I’m sure you’ve seen Naval’s tweet storms, but there is one big idea in his book that I think about daily. That is, you need to find leverage. 

Leverage is just a word for tools that amplify your efforts, and there is a killer example which I’ll share in a moment. 

But first, let me share how he explains it.

So, there are four types of leverage.

The first two are permissioned, meaning people need to give it to you. 

That's managing people through labour and managing money through people's capital. That's the old leverage that's existed for thousands of years. 

Then there is new leverage, which doesn't need permission: writing code that can be used thousands of times or creating media that can be rapidly spread around the world.

Now you can create even bigger outcomes when you combine different types.

Take paint contractors, for example. 

They don’t have much leverage, but their labour creates hundreds of dollars in value. 

A home developer has leverage; they manage lots of painters and contractors to make thousands. 

A real estate fund manages lots of home developers, creating millions. 

Then, if you bring know-how, capital, and technology together, you can build a real estate company like Zillow with a lot of leverage, creating billions.

Money & Investing

Venture Deals by Brad Feld

Unless you're in the venture capital world, it's unlikely you've heard of Brad Feld. He is a venture capitalist based out of Colorado and has published a ton on startups and financing. 

But his book called Venture Deals covers way more than that. 

I thought I understood term sheets. I’d read many, written them myself, and even advised people on what they should do when they got them. But then I read this book, and I realised how little I truly understood about them.

A term sheet is a simple document focused on economics and control in business transactions. They are the most powerful thing in the world for making money. 

Because while the business and the real-world impact happens out there—the products, services, customers, revenues, profits—who actually benefits from that financially doesn't. 

That happens in the written words on a page.

A good example of this in real life comes from a group of superheroes - The Avengers. 

The storyline, production, global advertising, box office revenue, and even a take on the popcorn eaten in theatres were the same for all actors involved. Except for Robert Downey Jr. 

He and his agent negotiated something unique in their term sheet – a percentage of the film's profits. Just as Iron Man upgrades his suit to fight the bad guys, Downey Jr.'s unique clause in the term sheet attached some big boosters to his paycheck. 

And the films crushed it, making about $30 billion so far. Due in large part to that tweak in Downey Jr’s contract, he has taken home almost half a billion of that for himself.

I share this because it was the same set, same movie franchise, same actors, same production - but it had vastly different financial outcomes due to one clause in the term sheet.

Valuation by McKinsey & Company

I studied business and finance in high school and college and learnt all the theory. 

It's a funny thing because you're working off case studies and textbooks, and the examples used sometimes seem like they have no relevance to you because you haven't seen how it works in the real world. 

Then, 10 years later, after working in the world, I picked up this book, and it all made sense.

Now, be warned - this book is a beast. Over 500 pages of dense material that you'll need a few weeks to get through. 

But if you want to truly understand how businesses are valued, this is the book. 

The biggest thing that's stuck with me over the years is understanding how important total addressable market, or TAM, is. 

Market size is the ultimate constrainer of growth. 

TAM reminds us that only so many units can be sold. If you've got ten hungry people, you can sell them all dinner, but once they've eaten, they're not hungry and not in the market for food anymore. What this means is you need to find more hungry people or figure out other stuff to sell them.

Apple offers a masterclass in this. 

See, in the early 2000s, Apple was limited by the small size of the computer industry. Then it created a completely new market to expand its TAM with the iPod. 

Existing Apple customers who liked music, even those who already had an MP3 player (man, that sounds old - do they still use that word?), got one to listen to music on the move. Apple created a new market to increase their TAM. 

But as the company got bigger, the law of large numbers is difficult to escape, so then they combined the phone and media with the iPhone. 

When everyone has a MacBook and iPhone, how do you keep expanding revenue?

Make each new iteration compelling enough to convince consumers to keep upgrading and buy more.

Fooled by Randomness by Nassim Taleb

Now here is an unfortunate truth: even with a complete understanding of term sheets and valuation, there's something that you can't know that will always have a big role to play in money and business, and that's randomness - captured perfectly in Fooled by Randomness by Nassim Taleb.

Remember in 2010 when there was a European debt crisis going on? 

Well, I do. 

I watched a lot of my stocks get smoked by fear in the market. Someone recommended this book to me, and not only does it talk about financial markets, it also teaches about randomness in life.

The big concept that stood out to me in this book is that life is not linear. 

Our views of the world work in straight lines and exclude randomness. We expect to go through life and check off our to-do lists, but then life intervenes and suddenly we need to make a new list. 

Things can also come together in weird and unexpected ways. That meeting with the lawyer, that lucky sales order, the early delivery - these breaks can all come together and cause big changes in your life. 

It’s like the blackout, that stopped the alarm from going off, so that person didn’t make the flight that crashed. And that randomness can manifest in arbitrary ways.

Sometimes you drop your phone, and the screen breaks; sometimes it doesn’t. 

Nassim tells the reader to recognise that it is just randomness and, in the long run, it will balance out.

Happiness

The Obstacle Is the Way by Ryan Holiday

Now, if that philosophy of welcoming both the wins and losses of life with a smile sounds familiar, it's a concept called stoicism. 

Stoic philosophy, interpreted by Ryan Holiday, teaches that the biggest obstacle is your thinking. 

There are two things in life

1. The event (which we can’t control) and
2. The meaning (the story we tell ourselves, which we can control).

I have to admit - sometimes stoicism can come off as inwardly focused and cold to outsiders. 

But in life and our relationships, we're often going to be let down by others and that's okay.

The Four Agreements by Don Miguel Ruiz

This fits perfectly with the big idea from the next book on happiness. 

I first came across this book in 2020. My wife found it through her yoga community and suggested that I read it.

At the time, the pandemic arrived and I felt like the world had stopped spinning and people were dealing with all sorts of stresses under all the massive changes we experienced. 

This book helped me zoom out and see the bigger perspective.

The Four Agreements are:

1. Don't take it personally
2. Always do your best
3. Be impeccable with your word, which is about keeping your commitments
4. Never assume

Now those Four Agreements may sound incredibly simple and something from a child's book, but often in life….

It's the simple principles that are the most impactful and meaningful. They are also the most difficult to follow. 

We all know a healthy diet comes from ‘eating natural foods, not too much, mostly vegetables’.... yet unfortunatley 40% of our developed world is overweight.

And while these principles can make us feel small or imperfect or weak, The Four Agreements remind us to always be a positive force of nature, driving change and good in the world, despite ourselves.

The Algebra of Happiness by Scott Galloway

I feel silly saying it, but the biggest thing I took away from this book was the reminder of something I already knew. 

But, as an introvert, I find myself needing to be reminded of it over and over again. 

So, in 1938, they started tracking the life of 724 men to figure out what factors contribute to human happiness and health over a lifespan.

It became known as The Harvard Study of Adult Development, one of the longest-running studies of adult life ever conducted. 

You know what they found is more important than wealth, fame, money, and exercise? 

It’s the quality of our relationships.

At the end of the book, Professor G shares how he thinks that the quality of people who attend your funeral is a good indicator of your success in life. 

I left Australia in 2014 for 10 years and while I’ve got a tonne of relationships I cherish, I feel sad that I lost touch with a lot of people since then. 

This lesson on relationships was one of the most important ones I learned while I was away.

It wasn’t all bad though… I wrote the things I learned which you can check out here.

I promise it's good stuff.