Revealed: My 3 most embarassing ASX investing mistakes

I made these mistakes so hopefully you won't have to.

Woman disappointed at share price performance with her hands on her face.

Image source: Getty Images

As you might expect with a Fool, I've been investing in ASX shares for many years now. Whilst I've been fortunate enough to enjoy relative success with my investing, I have certainly not been blessed with a perfect run. In fact, I have made many rather embarrassing investing mistakes with my ASX stock portfolio in the past decade, particularly in my first few years of investing.

Jaded investors often say that you can only truly become a successful investor by making mistakes and losing money. The pain of those losses can then be channelled into keeping yourself on the straight and narrow.

But I don't subscribe entirely to that theory. Which is why, today, I'm going to share these embarrassing mistakes in the hope that others can learn from them without losing the money that I did.

3 of my most embarrassing ASX stock investing mistakes revealed

Investing mistake 1: Buying a company that went BK

It doesn't take a giant intellect to realise that buying shares in a company that is in danger of bankruptcy is not a savvy business idea. Yet one of my first investments was exactly that. You might think it's difficult to turn a $2,000 investment into $4, but I somehow managed to accomplish this task. Buying Slater & Gordon stock (which has since been delisted) is still, to date, my worst investing mistake.

I purchased this company almost ten years ago when I was first embarking on my investing journey. At the time, I was attracted by favourable coverage and what was then considered to be a pioneering business model. It turns out the only thing that Slater & Gordon pioneered was how to go broke as a leading legal firm.

After a disastrous UK acquisition, Slater & Gordon ended up having to call in the administrators, and subsequently restructured the company at the expense of existing investors. My ownership stake was diluted to almost nothing, and was subsequently reaquired by the company thanks to its low value.

The lesson? Don't buy companies that are anything less than financially sound.

Mistake 2: Chasing a hot trend

In my first few years of buying ASX shares, I was susceptible to 'jumping on the bandwagon' and chasing the latest hot trends on the market. The stock market is almost always in the throes of the latest fad, the industry that everyone simultaneously decides is going to be the next big thing. One year it might be 3D printing companies. The next, it might be buy now, pay later (BNPL) stocks, or lithium shares.

The fear of missing out is a real problem investors have to learn to ignore. It can be hard watching other investors making what looks like easy money. Unfortunately, I once tried to do just that, and bought a bunch of shares that I didn't really understand.

This ended up losing me a whole lot of money when I eventually realised the error of my ways. Fortunately, I did eventually realise, and promptly sold out. As well as knowing when to hold 'em, it's also important to know when to fold 'em.

Mistake 3: Listening to an 'expert'

In the modern world of stock market investing, opinions and recommendations from third parties on which stocks to buy are not exactly as rare as hen's teeth. Whether they come from a family member, a taxi driver or someone on YouTube or TikTok, these opinions should always be taken with a grain of salt.

One of my most embarrassing and costly investments was made on the recommendation of a self-proclaimed 'expert' on social media. I invested heavily in their stock pick, only to lose the vast majority of my money when things went sour.

No one cares about your money as much as you do. As such, you shouldn't put too much stock (pardon the pun) in the opinions or recommendations of others. Use them to serve and inform you, not to guide you.

Motley Fool contributor Sebastian Bowen has no position in any of the stocks mentioned. The Motley Fool Australia's parent company Motley Fool Holdings Inc. has no position in any of the stocks mentioned. The Motley Fool Australia has no position in any of the stocks mentioned. The Motley Fool has a disclosure policy. This article contains general investment advice only (under AFSL 400691). Authorised by Scott Phillips.

More on How to invest

A group of young people lined up on a wall are happy looking at their laptops and devices as they invest in the latest trendy stock.
How to invest

How to build your first ASX share portfolio step by step

Starting your journey in the share market? Here is an easy way to do it.

Read more »

Legendary share market investing expert, and owner of Berkshire Hathaway, Warren Buffett.
How to invest

No savings at 50? Here's how I'd use Warren Buffett's playbook to build wealth and retire comfortably

Following in Warren Buffett's footsteps could help you retire wealthy.

Read more »

Man looking amazed holding $50 Australian notes, representing ASX dividends.
How to invest

How much passive income could I make from ASX shares with $10,000?

Wanting to turn your hard-earned money into passive income? Here's how you could do it.

Read more »

A broker caluculates a hold rating for an asx share price
How to invest

How I'd go about finding undervalued ASX shares to buy and hold forever in 2026

This strategy could help you beat the market over the long term.

Read more »

Man holding Australian dollar notes, symbolising dividends.
How to invest

Where to invest $10,000 in ASX 200 shares this month

Analysts think these shares are buys right now. Here's what they are recommending.

Read more »

Happy young couple saving money in piggy bank.
How to invest

DIY investors: How to build a stable income portfolio starting with $50,000

This is how I would build an income portfolio in 2026 for the long term.

Read more »

A young couple hug each other and smile at the camera, standing in front of their brand new luxury car.
How to invest

How much wealth could I build by investing $500 a month into ASX shares?

Building wealth isn’t about starting big. It’s about showing up consistently and letting time do the work.

Read more »

young people celebrating at a gold party
How to invest

How to become rich with ASX shares over the next 10 years

Here's how you could build wealth with ASX shares.

Read more »