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The thin line between investing and gambling

Ben Graham was born in England and moved with his family to the US when he was 1 year old. His father took the family to New York to set up a new branch of a successful family business. This was far from the prototypical immigrant experience. His family was wealthy and moved to 5th Avenue in a house staffed by domestic servants. This lifestyle would not last.

Graham’s father died in 1903 when Graham was just 10 years old. The family business soon went under and his mother sold off their possessions to keep the family afloat. In a last gasp to try and salvage a future for her family his mother took their little remaining money and bought US Steel shares on margin. She was wiped out in the 1907 banking crisis.

This was the origin of Graham’s hatred of speculation and in his most popular book The Intelligent Investor he drew a pronounced distinction between investors and speculators. Chances are he would not like what is going on today.

The not so fine line between securities markets and prediction markets

A derivative is a financial contract that derives its’ value from the price of an underlying asset. For instance, a USD currency future’s value is based on changes in the value of the USD.

Derivatives can be used to hedge an exposure or for speculation. Either way there is a consensus that derivatives on underlying assets like currency and commodities are financial instruments.

Then there is the prediction market. Like a derivatives market a prediction market facilitates two parties entering into a contract whose value will be determined by the outcome of an event.

Some of these outcomes could conceivably be used to hedge a market outcome like the recent contracts on the Iran war or those on consequential elections. Then there was the $145 million in trading volume based on Bad Bunny’s Super Bowl halftime show.

Many of the prediction contracts are on the outcomes of sporting events. The technical difference between sports betting and a prediction market is a bookie is the counterparty in betting while a prediction market just facilitates the trades. This is a difference without a distinction if you are placing the ‘bets.’

Investment markets and prediction markets merge

Investment and prediction markets are starting to merge in the US. Brokers Robinhood and Interactive Brokers Group now offer share trading and prediction contracts side by side. Robinhood has long focused on the gamification of investing. Now they are throwing off the pretense there is any distinction between investing and gambling.

As for Interactive Brokers, their Chairman Thomas Peterffy told Barrons, “In my mind, prediction markets will be the biggest space for investors in the coming years, I think it will far exceed the popularity of even the stock market.”

The regulators in Australia are taking a different approach and have classified prediction markets as gambling and banned them. In the US they have been declared ‘event derivatives’ and are regulated nationally by the Commodity Futures Trading Commission (“CFTC”).

Whatever you want to call prediction markets it is hard to argue they aren’t popular. In November 2025 prediction markets hit $13 billion in trading volume. That is up from $100 million in April of 2024. Polymarket and Kalshi are the two industry leaders.

The Wall Street Journal followed one ‘prediction market trader’ during the Super Bowl in February. The former university student dropped out to trade full time and saw the Super Bowl as an opportunity to take advantage of less experienced traders.

He went through all the motions of having a system in place. One picture showed him with two laptops and multiple monitors which he used to trade what he described as mind numbing volatility.

Reminiscent of a parrot who learned to mimic seemingly complex patterns he constantly traded during the game trying to take advantage of recreational gamblers. After placing $300,000 worth of trades he ended up with net losses of $100,000 during the three-hour Super Bowl.

Exploiting recreational investors

Since Ben Graham drew the distinction between speculation and investing the lines continue to blur. At the risk of seeming anachronistic I think the distinction still matters and your outcomes are dependent on which side you find yourself.

For those that still consider themselves firmly in the investor camp there is some good news. Investing success is reliant on identifying your edge or competitive advantage over other investors. The sources of edge range from analytical ability to simply making fewer mistakes than most investors.

A long-term orientation is an edge that anyone can exploit. And as more people lose sight of the differences between gambling and investing that edge becomes more valuable and easier to gain.

It is easy to look at predication markets from a moralistic high ground. It is satisfying to roll your eyes at the hubris and naivety of ‘prediction market traders.’ But we all can fall into the trap of seeing investing as entertainment and sport.

The reason all of us invest is to try to improve our own lives and the lives of people we care about. As more people treat prediction and share markets as a mechanism to gamble, keep focused on what really matters.

Ben Graham’s words serve as a reminder of where our focus should be. Graham said, “A long-term investor is the only kind of investor there is. Someone who can’t hold on to stocks for more than a few months at a time is doomed to end up not as a victor but as a victim.” Don’t forget that.

 

Mark LaMonica, CFA, is Director of Personal Finance at Morningstar Australia.

 

  •   25 March 2026
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10 Comments
James#
March 29, 2026

Warren Buffett (Berkshire) and Jack Bogle (Vanguard founder) instead advocate average investors buying and owning large diversified index funds for the long haul. "Don't look for the needle in the haystack. Just buy the haystack!" - Bogle.

LIC's are still stock (needle) pickers and annual dividend increases have not kept pace with inflation, especially over the last 10 years. Nor has capital growth! (Since 2016 inflation has cumulatively increased 36%.) The dividends of the likes of AFI, ARG, WHF etc certainly have not kept pace with inflation (AFI's normal dividend is barely higher than it was 10 years ago!) nor have share prices risen appreciably either. From a total return perspective, not good investments even if held forever.

Caveat: if one owns enough of anything, and the income is well in excess of income required/desired then set and forget would work.

Dudley
March 29, 2026


"Caveat: if one owns enough of anything, and the income is well in excess of income required/desired then set and forget would work.":

4% / y of $8M capital = $320k / y cashflow.
Return of capital. Return on capital not necessary if time is short.

Earn 5%, inflation 3%, withdraw 4%, present value 100%, future value 10%:
= NPER((1 + 5%) / (1 + 3%) - 1, 4%, -100%, 10%)
= 31.96 y

= NPER((1 + 5%) / (1 + 5%) - 1, 4%, -100%, 10%)
= 22.5 y

1.1 million Australians aged 80 or older.
5,547 Australians aged 100 or older.

Nadal
March 26, 2026

Cashflows can be generated from the markets through a range of different means, distinguishable based on time horizon and risk:
• Gambling: short time horizon (measured in seconds, minutes, hours, days) coupled with high risk (embodying chance and impulse)
• Speculation: medium time horizon (measured in weeks or months) coupled with medium risk (embodying intuition and judgment)
• Investment: long time horizon (measured in years or decades) coupled with low risk (embodying knowledge, experience and analysis)

1
Harry
March 29, 2026

The global equity markets are simply the biggest casino on earth. Decide your appetite for risk and go for it! It’s SO MUCH FUN ! Why not stick your neck out with 5%, 10%, 20% whatever.
If you don’t do anything risky, you won’t live any longer, but it might seem like you have.

James
March 29, 2026

With all due respect to the author, I strongly believe: gambling is about getting rich overnight, it is only interested in outcome instead of the process to achieve the desired outcome, it only leads to deadly mental addiction that will not create any sustainable wealth but severe psychological harms to any participants; investing is about embarking a life long process to grow and manage your wealth, it requires patience and constant studies of industries and geo politics, it is a joyful journey to accumulate long term sustainable wealth.

L.H. Moore
March 29, 2026

I agree entirely with James. Can I add that, like golf and tennis, but for most people far more profitable than either, investing continues but changes as one ages. As one grows older, the focus shifts from providing for one's partner, oneself, and offspring, to laying a foundation for future generations of one's family (if they prove capable of taking advantage of the start provided, which is far from a given). It is also a time for focus on supporting businesses and causes that one believes will contribute to a better future for mankind. Above all investing in 70's, 80's and 90's provides welcome intellectual challenges, and possible satisfaction, when a person's supposed career is long in the past. A joyful journey indeed.
Lindsay.

1
James
March 29, 2026

Thank you for your kind words. Though it seems to me that you excluded one group of people that is on the rise - single no ties men, who only need an income stream from their portfolio to replace their current employment, so retirement at 55 and live a life of leisure and entertainment is definitely doable.

The only mind set to obtain real happiness is to be able live your life by the following principle: never let others define you, define yourself. Otherwise men will live in perpetual miseries and sufferings.

In order to achieve the above, men, must first and foremost become financially independent, accomplished the task of creating enough wealth to fund his life of freedom and independence.

1
Lyn
March 29, 2026

James & Lindsay,
Agree with both re joyful journey, but also to never have to entrust capital to someone else to manage is important. Later in life it keeps brain oiled to have interest/ discipline of daily/weekly time for 'the job'. Generation with 12% Super Contr may become complacent about others managing such amounts thinking 'she'll be right, mate' so may never learn how to save & invest (plus a little speculation) outside Super as they think 12% adequate but that much in hands of others is scary if no personally managed investments to fall back on if things belly-up elsewhere. Nothing wrong with adage "have to speculate to accumulate" as long as speculation part not overdone. Mr. Graham's mother overdid it with only 1 share type due to lack of experience & panic by sound of after business went under on his father's death. Experience only comes with practice.

James
March 30, 2026

We all have outsource our needs to be met by different service providers ( plumbing electricians accounting landscape…), they all work fine provided there is a recourse If the services are not provided with satisfaction ( refunds or compensation). Except financial services, there is no recourse whatsoever under any circumstances. Therefore, it is definitely not a wise proposition to outsource your wealth management to any party, most average men are better off with fixed term deposit accounts. If you really hire a financial advisor, you must be highly involved in the process otherwise you will never become truly financially independent.

 

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