AI financial advice, reconsidered

In May 2023, I tested out Bing to see how good its financial advice was.

When asked general questions, like a request for a to-do checklist for absolute beginners, it performed very well.

When getting into the nitty-gritty of investment advice, it did poorly because it got sidetracked by financial media noise.

It was carrying on about stock picking, investing styles and so on, instead of the meat-and-potatoes of beginner investment: index funds, minimizing fees, and making regular investments.

It did say to focus on the long run so it got half marks for that.

Today I tried exactly the same prompts on ChatGPT-5, the uncelebrated recent upgrade from OpenAI, and here is a result comparison:

Me: What’s the best way to invest in stocks?

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Friday Finance -100% stocks forever

Stocks vs bonds, 2000-present. Yellow = bonds, red = stocks and black = stocks including dividends reinvested.
Source

It occurred to me that I need to edit the chapter on setting financial goals in my book.

Everyone’s financial goal is to have as much money as possible.

Aside from savings put aside for specific anticipated expenses, everyone just wants lots of money.

You can’t have too much money. An unexpected need might come up, or you can just give it away.

You’ll decide how much you want to work, of course, but there’s no rational reason why you’d invest in something that has a lower return than an alternative (risk-adjusted, of course).

Every so often, a paper comes out showing that actually, you should invest in 100% stocks, 0% bonds throughout your life, even into retirement, because this leads to the optimal likely outcome. It is said to be less likely to eventuate in a wipe-out.

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Friday Finance: the 3 best hedges against anything

Recent market ructions have made me think anew about hedging against risk.

All risk. Risk of market downturn, risk of unemployment, risk of sudden giant expenses, risk of Godzilla smashing up the nearest city.

Some advise cash, bonds, gold, crypto, diversification, timber, ammunition or peanuts (really!) as the best hedge against the many risks posed by life.

However, I reckon these three beat all of those.

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Friday Finance – catch every falling knife

In finance bro terminology, to catch a falling knife means to try to buy the dip only to find that the market falls even further, thus cutting your hand.

Dumb, hey? You should only buy right at the bottom.

The trouble is that no one knows where the bottom is.

The best time to invest, mathematically, is when you have the money to do so.

That is, when your consumer debts are sorted, you have an emergency fund saved, and so on.

Got a few thousand in the bank ready to invest and are wondering when to go for it?

Today’s the day.

So was yesterday.

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Friday Finance: robots, fools and corpses

The three best types of investors are robots, fools and corpses.

Trading bots follow their algorithmic instructions coldly and without emotion. So long as the instructions are sound, they will come out ahead of any human.

Fools can be successful so long as they are foolish enough.

Wildly trading and thinking you can win? Foolish, but not foolish enough.

Not even paying attention to the finance news, ignorant of the fact that you have an investment somewhere, not even sure what that means if you do hear about it? This is the ideal level of foolishness.

If you’re too dumb to even conceive the future or keep track of anything, any automatic investments made on your behalf like superannuation will be safe from your fumbling fingers.

And then there are corpses.

An apocryphal Wall Street legend is that a mutual fund manager investigated who were the most successful retail investors, and realized that most of them were dead and their next-of-kin had not yet notified the firm. These investors invested for a very long time without chopping and changing with market conditions.

So if you want to be a good investor, pretend to be a robot, a fool, or dead.

Today, given current market kabobulations, let’s imagine that we’re robots. Here are few simple instructions given to you as an AI system. Please follow these rules mindlessly, ignoring all other signals. They are based on long-term data and mathematically most likely to maximize returns over the long run:

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Friday Finance – what really beat inflation?

A man goes to buy eggs, 2024

For most of the world, inflation has settled back down to normal levels.

There was a spike in 2021 following the you-know-what interruptions and then the war in the following year, but the rate had largely subsided by the end of 2024.

On this part of the internet, readers are very concerned about inflation, always assuming that their nation’s currency is about to become devalued enough to use as wallpaper. For some, no matter what I say, Zimbabwe is always right around the corner and it will still be right around the corner 30 years from now.

Well, we had a decent bit of inflation there. What actually kept up with it, or beat it? Gold and/or silver? Bitcoin? Real estate? Something else?

Let’s have a look.

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The Infinite Money Glitch

HT

There really is an Infinite Money Glitch.

It won’t make you super rich, but it will ensure that you never come up short.

Before I get to the glitch, it may help to tell you why I’m writing this post, which is not so different from finance posts I’ve written before.

The same old stuff keeps on happening.

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The best and worst retirement plans

HT

A country’s retirement program was once like fjords or mild weather – a nice thing to have, but not a factor that would determine a nation’s position in the world like infrastructure or GDP.

With populations everywhere aging, this has changed. Those countries financially well-prepared for the coming decades are best positioned to prosper and to maintain their power and influence.

I got to thinking about this because I’m compiling the second edition of Poor Man’s Guide to Financial Freedom. I’ve been expanding the section on national retirement plans in the Anglophone countries.

Australia, New Zealand and Canada seem to have pretty good plans (compared to any others; perhaps not in absolute terms) while the USA and UK trail behind.

Further afield, the oldest country, Japan, and the least fertile, South Korea, both have about the worst retirement programs in the developed world. Even Chile does better.

The top ranked countries are the Netherlands, Denmark and Israel.

Because it will be so important in the future, here are my observations about what makes a good retirement plan in terms of adequacy and fairness.

Adequacy

A retirement program needs to be adequate both at a national level and for each individual. The keys to a sufficient and sustainable retirement program at the national level seem to be making it mandatory, a high retirement age, transparency and sound investment.

Mandatory plans

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The perils of FIRE

For a long time, I’ve been following the blog of a lady aiming at FIRE – financial independence, retire early. A few years ago she reached her goal, quit her job, and she and her ‘partner’ (no kids) now wander the world doing whatever they want on about $23k per year.

Her blog used to be quite engaging, with various discussions on personal finance issues that I found interesting. Once she retired, it became this:

We lived here. We ate this. I read these (romance/gay/race hustling) books. I played these computer games and here are my reviews and tips. I overspent my budget by 0.5%. This is how my investments are performing. I got my nails done. I did some paperwork for a visa. Here’s my sleep graph. Here’s a list of animals I saw. This is my emotions report.

I always knew she was like that but looking at it now, it’s clear she’s also autistic. Not that there’s anything wrong with that.

I object to these posts on a narrative level. If her story had ended upon reaching her FIRE amount, disappearing into the sunset with her ‘partner’ as stringed instruments soar, fine. To see the story continue after achieving her goal is like a romantic comedy where the last half hour is the couple fifteen years later, having a tedious argument about the toothpaste cap.

The story was meant to end there, or move on to some new narrative (challenge or problem facing the protagonist). To just read nonsense books, play stupid games, then post boring blog posts about that stupid nonsense is like a mini-death. A person without a narrative is spiritually dead.

You might say, just stop reading the blog if it bothers you so much. Dear reader, I unfollowed years ago. However, I keep creeping back to it, like a dog to its vomit. I can’t look away. Every six months or so something reminds me of her, I go see how she’s doing, and absolutely nothing has changed.

It would be easier for her to completely revamp her entire lifestyle than for me to stop checking her blog, so that is what ought to happen.

I also once reported on a man who achieved FIRE and spent most of his time reading, but after a few years his wife got bored and suggested they start working again. He said you can if you want but I’m good. She said she’d feel uncomfortable working while he’s sitting at home doing nothing.

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Personal finance – putting Bing through the paces

I’m interested to see how well the new chatbots might help people with their finances.

As noted in my book, there are already automated financial advisors that are pretty good for people with basic needs. Can Bing do any better?

Let’s see.

I’ll summarize what Bing says rather than strain your eyes with screenshots.

Me: Hi Bing. Imagine you are talking to someone with absolutely no understanding of personal finance. What ten basic steps would you recommend for them to get their finances under control?

Bing:

  1. Create a budget
  2. Build an emergency fund
  3. Pay off high-interest debt
  4. Save for retirement
  5. Invest your money
  6. Get insurance
  7. Manage your taxes
  8. Set financial goals
  9. Track your progress
  10. Educate yourself

My score: 10/10. I won’t quibble with the slight differences between this list and my list because we’re on much the same wavelength.

I didn’t specify that they should be in a logical order so let’s try that, too.

Me: What would be the logical order to do these in?

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Friday Finance – it really wasn’t financial advice

At the end of my irregular Friday Finance posts, I always add the disclaimer:

  • This article provides general information. It does not take into account your personal circumstances and is not intended to influence readers’ financial decisions. Get your own, professional advice.

I started doing this formally and consistently after the Old Country passed a law banning influencers from promoting any financial products and services.

I didn’t seriously think a tiny blog on the other side of the world spruiking the benefits of index funds would attract the Eye of Sauron, but why risk it?

You’ll see this sort of disclaimer all over the place and it is usually there as a legal fig leaf.

However, DO NOT DISREGARD IT.

You really must do your own research and get your own personal advice. Recent events should have driven that point home rather painfully for those who got caught out.

The collapse of FTX was so dramatic and absurd that within hours people were debating who ought to play the slovenly t-shirt guy when it becomes a Netflix series. I would watch it. Here’s a small taste of the madness (click through to see the full thread):

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Friday Finance – charting the 4% rule

I’ve been meaning to post this priceless table for a long time and today I finally got around to it:

Success Rates for different SWRs, by equity share and retirement horizon (1871-2015) HT

I put it right at the top so that those who already understand the chart don’t need to read the article if they don’t want to. It’s all there.

For the rest of us:

Wot dis?

‘Dis’, as you so vulgarly put it, is an estimate of how long your money will last in retirement depending on how much you withdraw each year and the proportion of shares vs. bonds.

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Friday Finance – what happens when empires crumble?

Some assume that a retracting Global American Empire will cause economic chaos.

On the face of it, this makes sense. The US controls Middle East oil and the global currency (those two go together like electromagnetism), shipping lanes to Asia, plus it has massive sway in global bodies like the IMF, World Bank and so on.

Countries that attempt to break out of the GAE system tend to be destroyed or isolated and impoverished.

However, all of these are now under threat. Some countries are starting to use alternative currencies, including oil producers. China is asserting control over the South China Sea and is either taking over or creating alternatives to international organisations.

Small countries are not yet able to blatantly defy America and get away with it but China, Russia and India can do as they please. Much of the non-Western world is on the cusp of slipping the collar:

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Friday Finance: beating the house

I often refer to the S&P 500 on these pages. It is an index of the largest 500 US stocks.

This is because, as far as investing is concerned, the S&P 500 is The House. It is the standard by which all other investments are measured.

This is not because an index fund based on this particular index is necessarily the best. One that is even broader, encompassing thousands of stocks or perhaps including international stocks, might better suit some investors.

Rather, the S&P 500 is the house because (a) it is the biggest game in town, featuring the world’s largest companies, (b) it is the most well-known index, (c) it has excellent statistics and charts available going way back, and (d) its size and importance makes it a good proxy for how well stocks perform in general. Many other stock market indexes closely correlate with the S&P.

If you want to know how well some other investment option has historically performed, you must ask: compared to what? And the ‘what’ will be the S&P 500, just as you’d compare the carbohydrate content of sorghum against wheat or the strength of chromium against steel. It is the bog-standard investment everybody knows and understands, it’s been around for a long time and it is as mainstream as you can get.

The Holy Grail of investing is to beat this index.

We know that a few manage to do it – Warren Buffet, some lucky geeks who sold their crypto just in time and so on. It is physically possible.

We also know that very few actually manage to do it. The average investor underperforms the S&P because he buys high and sells low rather than buying and holding for the long term.

In this post we’ll analyze various investment options spruiked by some as index-beating miracles and see how well they do. The results may be surprising.

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This is financial advice (for Smaug)

Smaug the Magnificent by Michael Hague

Smaug pursues a unique financial strategy.

Being the Middle Earth version of the Wolf of Wall Street, he emerges from the Grey Mountains and attacks the great Dwarven kingdom of Erebor, located beneath the Lonely Mountain, in 2770. He piles up all the treasure of the underground kingdom in a great hall and makes it his residence. Forbes estimates his net wealth at USD $62 billion.

From this time on, Smaug only emerges occasionally to steal and eat a maiden from neighbouring Lake Town. Good thing he didn’t live anywhere near my town or he’d have been a very hungry worm. Eventually Lake Town is abandoned and he disappears for a long time, presumably inactive and asleep like those snakes in zoos that do nothing and only need to eat once every two years or so.

Smaug chooses not to invest his wealth in stocks, bonds, real estate (aside from the mountain) or in money market accounts. He doesn’t even have a bank account. Instead, he keeps it all in its original treasure form, mostly physical gold but also priceless antiques such as mithril armour and the Arkenstone.

Finally Smaug is killed in 2941, ending his wicked reign of 171 years.

Here are some finance tips that might have helped Smaug.

The Good

1. Bookkeeping
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Friday Finance – DON’T PANIC!

The S&P 500 is down 21% at the time of writing, making this the worst first half of a calendar year on the market since 1970.

PANIC! SELL EVERYTHING! SET FIRE TO YOUR KITCHEN! EAT YOUR DOG! PUT A PAIR OF UNDERPANTS ON YOUR HEAD! This is financial advice.

Okay, if you’ve been reading this for a while you’ll know why that’s the worst thing to do. Unless you sell, the losses are paper losses. Wait long enough and stocks will recover. Based on history, this is likely to take anywhere from several months to several years.

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Friday Finance – stuffing up the 3 basics

It’s now been long enough since I published my book that I’ve received some feedback and seen how it has or has not helped people.

I was initially concerned about higher-level issues, given that it was aimed at absolute beginners: will they be able to figure out the most appropriate index funds/EFTs without me holding their hand? Did I explain the pros and cons of owning real estate well enough for them to make the best decision for themselves? Will an advisor overcharge them just to put their money in shitty managed funds, despite all I’ve said?

As it turned out, these problems rarely arise. It seems that people either get everything, from the basics up, or they grasp nothing at all.

Here are the three biggest finance blunders people are running into, even after reading the book:

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Friday Finance – Millennials will save America

The hard sell

‘Millennials will make the American economy boom over the 2020s.’

It’s an unusual sentiment to hear in this age of doom and gloom.

My first reaction was the same as yours, but Tom Lee has put together a convincing demographic case that American growth ought to be stronger than than of other major economies into the 2030s due to its comparatively large Millennial population.

Let’s examine the stats and consider counterarguments.

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Friday Finance – USD will die hard

female and dollar bills

Source

[Edit: I wrote this article before the Ukraine war and have added an update at the end. Let’s see how wrong I was.]

We’ll all be rooned!

There’s a lot of panic about the American dollar going the way the Zimbabwean dollar, what with all the brrr* and inflation and what-not.

It’s important to keep this in persective.

In the foreseeable future, uncomfortably high inflation is likely but hyperinflation is not.

Given the Japanese experience, the chances of deflation are >0.

Reserve currency
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