The Inside Word #6 – Captain FI

Disclaimer: This website (the “The Money Pal”) is published and provided for informational and entertainment purposes only.  The information in this article constitutes the interviewees own opinions and it should not constitute as personal advice nor any formal recommendations.

The 6th edition of The Inside Word features a pioneer of the FIRE movement down-under, Captain FI. Captain FI is a retired Air Transport Pilot who lives in Adelaide, South Australia. He is passionate about Financial Independence and writes about Personal Finance and his journey to reach FI at 29, allowing him to retire at 30. 

Let’s get stuck in.


Welcome to the Inside Word Captain FI! Firstly, what’s your coffee order?

I’ve had a break from coffee recently. The caffeine is really messing me up at the moment. If I order coffee, it’s usually decaf almond cappuccino. 

I also drink a lot of herbal tea. I like growing herbs on my balcony and then using those to make lemongrass and mint tea. 

Cats or Dogs?

Both.  Although cats have to be inside just because of the destruction they cause to native wildlife. 

I probably do sway slightly more towards dogs though. I just love how physical they are. And you can play rough with them too, especially big dogs. 

Early Riser or Night Owl?

Definitely an early riser. I have done my fair share of all-nighters and late nights though. 

Especially when you get into the groove on an article you’re writing and you’re just so passionate about it you can be up until 1 am and you’re like, oh my god, I still haven’t finished writing this article.

Now that I’ve got the choice, I choose to go to bed early and then wake up early most of the time.

3 People you’d invite to dinner (dead or alive)?

  1. Mr Money Mustache, the OG FI Blogger.
  2. Vicki Robbins, Author of ‘Your Money Your Life’.  I’d love to have dinner with her just to see her perspective on life. 
  3. This is probably gonna be cheesy, but I’d love to go back and, and chat to some of the early scientists. Like Niels Bohr, Einstein and Stephen Hawking. I don’t think I can give you an exact answer on this one, but definitely someone who’s been really influential in physics, engineering or mathematics. 

Pineapple on Pizza?

Sure, why not.  I’m pretty easygoing. I eat pretty much everything except mushrooms because I’m enough of a fun-ghi. 

Coriander. Yes or No?

I love coriander. I’ve got plenty of growing on the balcony. Some people say it tastes like soap. I don’t really get it.

Favourite Plane?

Easily the Cessna 172 Skyhawk, which is the most manufactured aircraft on earth and hands down the best plane ever. It’s the most forgiving plane, the most docile plane, the most versatile plane. It’s easy to fly, easy to navigate, easy to land. Just easy peasy. 

A close second would have to be The 747 Queen of the Skies. 

1. Can you share the story behind why you chose to get started investing, and if anyone, in particular, inspired you on your journey? 

I grew up in a single-parent household in a big family. My Mum is absolutely amazing, and my Dad was not in the picture. He didn’t support her financially. She also struggled with health issues and was even hit by a car at one point while cycling to work. 

Raising a big family on a low salary as a teacher was a struggle for my Mum. So much so that we grew up below the poverty line.  That’s made me very used to trying to not spend money and to live very frugally from a very young age. That’s just a really important thing to keep in the back of my mind, as I explain this is.

Starting With School

During high school, I found myself in trouble a lot and suffered from some behavioural issues that led me to attend around 20 schools. 

When I got into my last two years of schooling, I had a pretty amazing teacher who asked me if I realised I was on a path to destruction.  He asked me to look in the mirror and think about what I wanted, and where I wanted to be. Initially, I just brushed it off. But it did stick with me and I realised I needed to get my shit together and decided to work really hard in years 11 and 12. 

I should point out that my schooling was quite sporadic. I was put up years I was held back and spent a lot of time either being homeschooled or being taught through behavioural rehabilitation centres.

For example, when I was in year 11, I was learning polynomial division in specialist mathematics, and I had no idea how to do long division, which was crucial for that topic.

Thanks to some great teachers, I ended up doing really well at school and basically got perfect scores, which enabled me to get into Uni on a fully paid scholarship. 

That was really only possible because my Mum was amazing. She sacrificed so much to support us. She’d spend any money she had on stationery and books.  I remember the day she bought me this big corner desk for my bedroom so I could spread all my books out. She was just amazing. I wouldn’t have been able to do it without her. 

University, Flying Lessons & Frugality

That takes me to Uni, where I’m studying engineering, and I’m being paid to study with the dream of becoming a pilot. I was hooked on the idea at 14 when my Mum saved up and bought me a flying lesson. 

Unfortunately, I got rejected so many times from cadetships and pretty much everything I’d apply for. I realised that the only way it was going to happen was if I paid for my training myself, so I decided to start spending all my money on flying.

I continued to live the frugal lifestyle that I grew up doing, didn’t spend my money and started working extra jobs and side hustles like flipping cars and selling on eBay.  Basically, any money that I could make, would go into flying lessons while I was studying.

Eventually, I got my private, recreational and commercial flying license while job-hopping from engineering desk jobs and taking more aviation-related courses.

It was getting to the point where I was spending money on training that I probably didn’t need just because I thought it was so hard to get a job as a Pilot. I thought If I had all the training, then it would be easier to get a job.

Landing A Job, and Becoming An Investor

Eventually, I landed a job as an international transport pilot and absolutely loved it. That meant I had money coming in, but I wasn’t spending it because I continued to live that frugal lifestyle. It didn’t take me long to realise I needed to do something with it. 

Initially, when I’d accumulate 20K or 30K I’d spend it on additional flying training. I knew I should have been saving, investing or buying a house like everyone kept telling me. In fact, I tried to but the agents mucked me around a bit. In the end I pulled my money off the table and just spent that money on aviation training. 

Captain FI’s First Investments

From there I invested in a mutual fund that was performing terribly compared to the market. 

Ironically, the fund manager kept sending me glossy brochures telling me how much money I was making, and how smart I was to be investing with them. But when I cross checked everything in an excel spreadsheet, it just didn’t add up. So I withdrew all my money and had it sitting in cash.

After that, I looked at buying another property but couldn’t find one. From there, I read the Barefoot Investor and decided to invest $28,000 into ASX:AFIC, which I thought was a concrete company. I didn’t realise that it was a listed investment company initially. 

Thinking that AFIC was a concrete company,  I thought, there’s a lot of people building houses that need concrete. As it turns out, that investment was a money mistake because I invested without doing any proper due diligence. 

From there, I signed up to the Barefoot Blueprint, which got me interested in reading about finance and investments. It was only after that I realised, AFIC wasn’t actually a concrete company. I felt kind of stupid, but I was also reassured by the Barefoot community that it was a good thing to do. In the end, I held that stock for years.

That one lesson led me down the rabbit hole where I discovered people like Mr Money Mustache while reading hundreds of books about finance, personal development, and investing.

Other Initial Inspirations

Other early inspirations were people like JL Collins, Go Curry Cracker and Ramit Sethi,  who were all talking about the idea of FIRE, or as Lacey Filipich puts it in Money School, ‘financially independent, time rich’

These people taught me FIRE isn’t about retiring early to go and watch TV all day. It’s about having the time to do the things you love. 

2. Your website is loaded with some awesome content for both experienced, and new investors. Why are you so committed to helping others improve their financial futures?

The main reason I started this site was for me to learn about investing.

If you ask a question online, generally people will dismiss you. But if you post  ‘an ETF is the best way to invest ever’ You’ll get hundreds of comments saying, “no it’s not”, and you’ll end up having an engaging debate about it. 

I started posting about my experience with finance and different financial products on Captain FI so that I could be critiqued by the community and so I could be accountable to myself about my process to financial independence. I also wanted to document my journey as a resource for anybody else to follow along and hopefully, that might help them make some good choices. But really, what I was hoping to attract was the bigger fish that were smarter than me, that could say, “Hey mate, please don’t waste your time on that. That’s crap.”

So I started doing all the research to try and figure out what the best solution was for me, and put that online to save everyone else’s time. From there, the community returns the favour by critiquing my process. Incredibly I’ve got so much feedback from doing that. It’s been amazing. 

I even started getting really emotional, personal letters and feedback.  When I first got the email, I almost had tears in my eyes. I couldn’t believe that people were writing this. Particularly when single Mums would write to me. Single mums are a soft spot for me. My mum was a single Mum and I have a lot of friends who are single Mums. 

I’ve seen the power that financial independence can have on families, particularly single-parent households, and single Mum households. So I love it. And I love talking about it. I have just become a total money nerd. I still don’t think I have the right answers. I’m not perfect, but I’m so happy to keep working on it. 

3. You became financially independent before 30.  Can you reveal some of your secrets? 

When I was a kid I would buy lollies from a discounted Lolley store. I’d take them to school, and undercut the canteen. I’ve always had this need for financial security and a desire to make money by investigating alternative ways of producing some kind of income. 

So the secret is, it’s hard work. It’s sacrificing the short term pleasure for long term gain because there’s no such thing as getting rich quick. 

It’s also about questioning everything, like spending the time to get your bills down as low as possible. And then keep your investing simple. For me, I found the simplest thing has just been total market, broad index-tracking ETFs.  I’ve also invested in property, which has negative gearing perks. This is not financial advice. This is just how I’ve personally done it.

Once you’ve done all of that hard work, the savings, the investing, you automate it so that it automatically happens.

All in all, you need a strategy, you need a desire, and you just have to stick with it. 

Increasing Your Income 

The only way to get rich quicker is to increase your income. To do that, you can negotiate a raise, switch jobs, change careers to do something more lucrative or start a business.

I think starting a business is a way people can accelerate their earning potential, and there are a lot of tax advantages to having a business. Personally, I was well on my way, just through earning a flying wage, saving and investing. From there, I pretty much reached my single FIRE or lean FIRE numbers. And then through online businesses, I was able to generate a bit more income, which I can then either spend on my lifestyle or what I’m actually choosing to do is scale my business with the profits. 

Ultimately, the secret is that there are no secrets. All the information you need is all widely available for free online. The content is all out there. It’s all free, you don’t have to pay a cent. 

4. Cryptocurrencies have been a hot topic of conversation this year.  What’s your take on the cryptocraze? Are you a believer? 

I was very negative and dismissive of cryptocurrencies initially. Jesse, we could talk for hours about the way society is designed to transfer wealth and how capitalism is designed to steal the labour of workers. The reality is, the fiat monetary system is designed to keep the ruling elite in power. In my view, cryptocurrency is fundamentally trying to level the playing field. 

Look, I totally missed the boat on crypto and got bad FOMO. I bought it when it was pretty high. Since then, I’ve done some interviews with some pretty smart crypto guys. Stefan Laverra, Bitcoin Maxie and Andrew Fenton really helped shift my mindset.

The fact is, the technology behind cryptocurrencies is pretty cool. The ledger has the ability to allow people to transfer value without a middleman.

I suspect the central banks, the governments, and the monetary system don’t like it because it gives them less control. I personally see some kind of kickback or aversion on behalf of the status quo because the people in power may fear crypto will change the way we transact.  

I’m not going to go ahead and slap 100k on Bitcoin, I think that’s incredibly risky, but I’m increasingly thinking  I’ll aim to get 1% of my portfolio in cryptocurrency. Maybe even 1 to 5% might be something worth considering.  I’m not rushing out to buy loads of crypto, but I am slowly dollar-cost averaging into bitcoin and ethereum. They seem to be the two biggest ones. Again, I’m not very well educated on this. But to avoid the FOMO, I’m just averaging a little bit into it.

Making money in crypto doesn’t necessarily need to be made from trading it either. There are people out there who have crypto review sites displayed with Google AdSense, or other affiliate products and are making money out of Bitcoin, just from talking about it and may not actually hold Bitcoin. There’s money to be made in selling picks and shovels too. 

5. What’s one share market myth that you’d like to bust for readers without any investing experience? 

Easy. You can’t beat the market.  Let me just say it one more time. You cannot beat the market. 

I tried everything to beat the market. I’d even say, ‘I got around the same’ to try and justify it to myself psychologically. I even used stock picking services and realised that those are just media agencies. They make their money from subscription services, and if they were so smart at picking the market, well then they wouldn’t be sharing that information with you. 

Don’t try and beat the market, just be the market.

I believe the people that can consistently make money stock picking are insider traders, and maybe statistical anomalies like Warren Buffett. There are papers that have proven that Warren Buffett could have just been a statistical anomaly, and if you flipped a coin the right amount of times, you could have copied what he did. 

I don’t want to discredit anything from Warren Buffett, because I think he’s a brilliant man. And I love reading about him, as well as The Intelligent Investor by Benjamin Graham. That one is a bit of a rite of passage. I think everybody should read it. It’s a bit of a hard read, but after you read that, you will basically come to the conclusion that you cannot beat the market and someone else on the other side of the trade is smarter than you.

I think the best thing you can do is just not buy into all the bullshit. Don’t try and beat the market, just be the market.

When To Sell?

The other side of the equation is, when do you sell? At one point you’re going to have to. With index tracking and ETFs, I’m just basically saying I can’t beat the market. Instead, I’m going to be the market and let the index do all its work for me. 

That way, it’s never there’s never a good time to buy, and it’s never a good time to sell. It’s also never a bad time to buy, and never a bad time to sell.

6. What advice would you give to someone brand new to investing, but overwhelmed by all the financial jargon?

Just ignore all the noise, and get some skin in the game. Don’t get me wrong, I think there are a few steps I think people should take, I’ll just give a selfish plug here. I’ve got an article which is about financial independence for beginners, and it goes through the steps that I think people should take.

To get started, don’t do something as silly as I did and invest 28 grand into stock you know nothing about. Instead, try micro-investing. There are a plethora of micro-investing platforms. Take your pick, any one of them is fine. From there, go ahead and invest a very small amount of money. Get some skin in the game, and just see how it goes. 

Start Your Snowball

Once you’ve made a small investment, whether that’s $50 or $100, you will become interested in it naturally. You’ll want to learn how your investments are going, and you will start reading about investments. But until you’ve made an investment,  you probably won’t care. 

Initially, it’s about motivating yourself to become educated, that’s why dipping your toe in the water is important. Just so you can start learning, and that’ll help start your snowball. Starting off with a beginner book is important as well (Captain FI’s book recommendations are listed in question 9). 

If you don’t have the money to start off, sell something in your house. If you have a surfboard or snowboard, or something of value you don’t use, sell it. 

I guarantee you can make a couple of hundred dollars selling sh*t in your house to make micro-investments that will start your compounding process.

7. As some readers may know, you’re a trained pilot. Are there any skills you’ve taken from your flying experience that you can translate into your investing practice? 

To have a successful flying career, you really do need a long term focus to get where you want to go. You don’t just walk into becoming a captain of A830. A lot of people will spend 40 year careers in aviation and never make it to Captain on a superjumbo. That’s why you really need to have that long term focus in aviation, and it’s the same with investing. 

Risk Management Is Key

Day to day, the risk management aspect of flying has assisted a lot by helping me control my behaviour. Owning individual shares is the riskiest thing I could do. Don’t get me wrong, I do it with my one share in Tesla, which isn’t a lot. On the flip side, I have around 400k invested in index-tracking ETFs. So I’ve definitely translated the risk management approach that’s required with flying.

Cockpit Chit-Chat Has Been Really Handy

As pilots working on multi-crew transport aircraft, you talk a lot with your co-pilots in the cockpit.  Mostly about finance and business. I’ve taken a lot of lessons from colleagues about the mistakes they’ve made. Interacting with them has also helped with my social skills and overall emotional intelligence. 

Knowing how to interact with people has been really beneficial in my business ventures because at the end of the day when you’re buying websites, or writing,  you need to be able to relate and talk to people. 

Australian Is Loaded With Opportunities To Grow Financially

One of the bigger things that comes with travelling the world and seeing different cultures, is that it can be an absolute culture shock. Particularly around the Middle East, Southeast Asia. When things go wrong, or when societies aren’t functioning the way they do in Australia, it’s pretty confronting. 

Travelling to these places has given me a huge appreciation for the opportunities that we have in Australia. Especially after spending 6 months in Dubai, and finally coming back to Sydney. It was just like oh, my God, how amazing is Australia? 

Travelling reinforced to me that we live in this amazing country, and all we have to do is not spend all our money and invest a little bit of it and you can reach financial independence. 

Automate, Automate, Automate.

The single most powerful thing that I have taken away from my career as a pilot into investing is the use of automation. Learning to use automation really improves the safety of flying, reducing the number of accidents and incidents. 

By using an autopilot, Pilots can prevent human errors from happening, which can prevent undesired aircraft states.

We use automation to our advantage to make the flying experience safer. By automating your investing, you can take the human out of the loop. You can remove your emotions, you can focus your efforts elsewhere, and you can allow your investments to grow and compound all on their own. 

7. What’s your approach to your own personal investing, do you follow a certain strategy or strategies?

My investing philosophy is a core, and satellite system. The core is broad-based, lower risk passive investments. That’s not just stocks either.  I have an investment property. I have an online business and a bunch of websites that I diversify by having multiple monetization strategies for each website.  My superannuation and annuity are other parts of that diversified core. 

Core & Satellite Approach

I also do satellite investments, small little stabs here and there. We talked about crypto earlier. Bitcoin might go to zero, it might go to $10 million dollars a coin. Who knows, but I think there’s a thing called the asymmetric risk profile, or the upside. At the moment, I believe the risk upside for me personally is worth taking the risk on a very small amount of my net worth. 

Keep in mind, anytime you see people online, or anyone famous talking about their speculative investments, think about it as a percentage of their total portfolio. 

It comes back to risk management. Someone who has a net worth of $50,000 who buys $100,000 of Bitcoin on margin has done something really dumb. On the other hand, someone who is a billionaire buying $100,000 worth of Bitcoin translates to a minuscule fraction of their overall portfolio. That’s like a normal person going out and investing 20 cents in Bitcoin and boasting about it. 

These people are often talking publicly about their investments to manipulate the market, or to sell pick and shovels through connections to exchanges, or some kind of vested interest. 

Captain FI’s Portfolio In a Nutshell

To summarise, my personal approach to investing is to be sceptical. It’s to have a core of diversified investments i.e. property, stocks, business and super. I also have some satellite investments in things like crypto, one Tesla share, and a few other small investments HACK, which is an ETF that’s got a bunch of cyber security companies in it. 

I also have a good portion of money in six Park and Stockspot, which are robo advisors. For me, it’s all about spreading my investments as widely as possible.

9. What’s your go to resource(s) for finance/business related content? (This could be podcasts, websites etc)


  • Aussie Firebug
  • Fire & Chill
  • My Millenial Money (Great for beginners)
  • She’s On The Money (Great for young Women)
  • Her First 100K 


10. Do you have any must-read books you can recommend to our readers? (These don’t need to be associated with finance and/or investing)

Alright this list is going to sound super overwhelming at first. But remember, there are options. You can borrow them from your library, you can listen to them for free online, there are even websites that do simple book summaries so you can get a short summary and take away the big points of each book. 

That said, I don’t think anything could really beat having a physical book and reading it in the park under a tree.

Core Books For Beginners

From There, Go To

After That

Other Awesome Books On Investing

Lifestyle & Mindset Reads

Want To Read More From Captain FI? Check Out His Blog!  If you’d like to listen to Captain FI, why don’t you listen to his podcast?

For more of Captain FI, Follow him on Insta @captainfi, and while you’re at it, why not throw me a follow @themoneypal.

Enjoyed this interview and keen for more? Check out the my other interviews here.

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Disclaimer: This website (the “The Money Pal”) is published and provided for informational and entertainment purposes only.  The information in this article constitutes the interviewees own opinions and it should not constitute personal advice nor any formal recommendations.

2 Responses so far.

  1. CaptainFI says:

    Great interview Jesse, thanks for having me on mate

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