Getting Rich With Asymmetric Money Moves

Asymmeric Money Moves

The concept of asymmetric wealth creation is a powerful way to grow your earnings, increase your investment returns, and improve your life more generally.

The best thing about it is that it’s also very easy to incorporate into your decision-making.

All it takes is a slight re-framing of the way you look at opportunities to earn money, invest your savings, and spend your time.

Intrigued?  Let’s dive in.

The Beauty Of Asymmetry

Imagine I offer you the following trade.

We flip a coin.  If it’s heads, I give you $10.  If it’s tails, you give me $10.

Should you take the trade?

Well, it doesn’t really matter.  Assuming a large enough number of coin flips, we both end up exactly where we started, at least financially speaking.

But what if I was to change the rules?

Let’s say that I was willing to offer you $50 for every heads you get, but only take $10 in return every time it’s tails.

Well, now THIS is a game you should be willing to play all day long.

After 100 flips, you would end up about $2,000 ahead (50 heads * $50 less 50 tails * $10).

In other words, every flip has an expected value of $20 (50% chance of winning $50 and 50% chance of losing $10).

Bring it on… except that I am not walking around offering trades like this one.

But the good news is that when it comes to creating wealth, there’s an abundance of asymmetrical opportunities in life.

All you need to do is spend enough time looking for them – and putting your money behind them.

The Ivory Tower

A very basic example of a highly asymmetrical money move is upskilling yourself through part-time or full-time education.

Let’s say you are 25 years old and plan to work for another 30 years.  You can keep plugging away as you currently are – or you can get an advanced degree that will lift your salary by $40k a year.

Over a 30-year working career, that adds up to $1.2m of incremental earnings.

In that context, spending $20k or even $50k to get that degree is an absolute no-brainer.  Financially, you still end up light years ahead of where you started.

This is not to say going back to school is always a wise move.

There’s the time value of money, taxes on incremental income, and expensive degrees that take a long time to complete but give you zero earnings upside.

Also, the math might break down if you decide to pursue extreme FIRE and retire in the next 10 years or so.  In that scenario, you might not be working long enough to get the right return on your investment.

But the fundamental premise holds firm.  This is exactly why so many people (myself included) choose to go back to school as a way to climb the wealth ladder.

Side Hustles

As much as I dislike the “hustler” philosophy, a side hustle is yet another great example of an asymmetrical money move.

Take blogging.

It costs literally nothing to buy a domain and some hosting.

Assuming you’ve got 5-10 hours in your week where you are otherwise unproductive (watching TV, spending time on social media, etc.), the opportunity cost of writing a blog is also likely to be minimal.

Social Media Usage


Now, one of two things can happen here.

Your blog can wither and die.  This happens to most people and is primarily due to a lack of focus, passion, or persistence.

Too bad – but you are NOT any worse off.  A few bucks out of pocket and a bit less time on Instagram.  Zero harm done.

Alternatively, your blog can blossom into a nice digital property generating $1,000 (or much more) per month in side income.

Yes, it’s a lower probability event.  That being said, it makes starting a blog an equivalent of a trade with no downside (which is why so many people try it in the first place).

Investment Opportunities

The concept of asymmetry is equally relevant when you put your money to work.

As an example, I always run a downside case when I look at buying real estate.

That is, I assume that everything that can go wrong, will go wrong – and look at what happens to my returns in that scenario.

Let’s say my downside case suggests I will break even – while my “base case” indicates a 15% annualized return.

In that context, making the investment an absolute no-brainer.  Worst case, I end up where I started.

But if the worst case doesn’t transpire (and it rarely does), it will be a home run and I will generate a return well north of what I would be able to get in the stock market.

Speaking of which…

Money Slam Dunks

Yes, the past does not predict the future.

Yes, valuations, volatility, pandemics, inflation, armed conflicts, Russia, climate change, and everything else.

And yet, stock market investing remains one of the most asymmetrical money-making opportunities available to retail investors.

As a matter of fact, it gets even more asymmetrical – in your favour – as time goes on:

S&P 500 annual performance

I mean, if the worst that could happen is you only make 7.8% on your money over 30+ years, what are you waiting for?

And you can take it to a whole new level if you invest through tax-deferred investment vehicles like UK workplace pensions, 401(k) plans, and Lifetime ISAs.

It’s basically taking the stock market and putting it on the mother of all steroids.

To illustrate the point, here’s what an 8% equity return looks like when you invest through your workplace pension:

UK workplace pension returns

Even a minimum employer match of 75% transforms an 8% return into a 12% – 14% returns.

Those in higher tax brackets or with more generous employers could get up to 15%, annualized.

And it’s all available to you – at a click of a button.

Beyond Money

There are many other asymmetrical moves that can help you live a better, happier life.

A quick 30 minute burst of exercise and meditation in the morning will make you feel dramatically better for the next 14 hours.

A good diet will do wonders to your energy levels – and avoid a lot of health issues down the road.

Similarly, paying proper attention to your spouse will make for a much happier marriage and is likely to save you some expensive counseling or even a trip to a divorce lawyer in the future.

But as it turns out, the asymmetry works both ways.

The Other Side Of The Trade

The obvious thing to point out is that you NEVER want to be on the opposite side of an asymmetrical money move.

That is, unless you prefer to incinerate your wealth as opposed to growing it.  Sadly, there’s plenty of ways to light that hard-earned money of yours on fire.

Some folks do it by financing discretionary purchases with expensive, 20%+ credit card debt.

Many others still pay active money managers a whopping 1% fee to underperform the market:

Active Money Managers

Yet others take things to a whole new level and pay hedge funds a 2% management fee – and 20% of profits – for the illusory promise of delivering “risk-adjusted” returns.

The asymmetry also plays a big role in incentivizing the people who work for you.

As the banks have quickly found out during the financial crisis, it’s not necessarily a good idea to pay traders a percentage of the profits they generate.

For the traders, there’s only upside from taking on increasingly risky trades.

The worst outcome for them is losing a job.  The worst outcome for the banks is being saddled with multi-billion losses that take years to unwound.

Ditto for CEOs who have deep out of the money stock options as part of their comp structure.  They know the only way they will ever get paid is to swing for the fences with risky strategic moves.

No wonder that hedge fund managers, star traders, and risk-loving CEOs usually end up rich – they are on the right side of the trade.  Make sure you are not on the opposite one.

But leaving that aside, take a moment to reflect on the most successful people you know.

Chances are, many of them are probably taking advantage of asymmetrical opportunities to optimize their finances – and life more broadly.

If you want to join them, you may want to do the same.

As always, thank you for reading.

About Banker On Fire

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Banker On FIRE is an M&A (mergers and acquisitions) investment banker. I am passionate about capital markets, behavioural economics, financial independence, and living the best life possible.

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20 thoughts on “Getting Rich With Asymmetric Money Moves”

  1. Your combo of banker compensation and blogging income could be huge.

    I couldn’t last after 2.8 years so I negotiated a severance and spent more time writing on FS.

    But one thing people don’t realize is that blogging can be very lucrative. Instead of $1,000 a month, think $10,000 a month or $100,000 a month as a hurdle, which much less work and more fun!

    Anything is possible! Just gotta try.


    1. Cheers Sam

      Don’t think I’d want to combine “full-time” blogging AND banking at the same time, though if I did leave banking I would probably spend more time writing and monetizing the blog. Doing both full swing as a full time parent is not feasible.

      And yes, agree with you – the $1k/month is not a high threshold. Many folks out there (yourself included!) doing much better than that!

  2. I love this post and how it frames the stock market as an asymmetric bet! It is one of the most well-composed arguments for index investing despite the potential to lose money that I have seen. I wasn’t sure if you would discuss individual stocks or crypto bets, but I was pleasantly surprised that the focus was on more strategic bets rather than ones of sheer luck.

    My favorite asymmetric bet is mountain biking. While there is the risk I could get hurt every time I go out and ride, the chances are I will get a great workout instead.

    1. Cheers Olaf

      I think individual stocks are definitely NOT asymmetric, with the vast majority of them underperforming the index.

      Crypto is an interesting one. Could argue it’s asymmetric when the lower bound is zero and the upper bound is theoretically pretty high. That being said, I cannot in good conscience recommend crypto investing to those who are just starting out (notwithstanding the fact that I own some crypto myself).

  3. I thought you would mention startup investing in this post: one attraction of this asset class is this large asymmetry. Return floored at – 100% when they fail, but potential for a +1000% or more on a few rare cases, which can more than compensate.

      1. @Olaf @Oliver

        I agree with that. For me, the best asymmetric bet is where the downside risk is limited (hence the blogging example) and the upside is multiples of the money/effort invested.

        Startup investing is tough for two reasons. One is that most companies indeed go bust. The other one is that the best opportunities are “reserved” for blue-chip VCs and proven angels/entrepreneurs, as opposed to retail investors.

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  5. I saw myself in this article. This article has resonated with me. There is a hidden asymmetry written about in Nassim Nicholas Telab book “Skin in the game” what stood out in your article was the time lines. For example how asymmetry can work towards a 10 year time line depending on where we are.

    So for me doing a course is to my advantage. At this moment in time my biggest asset is my brain! Like for example doing an on line course

    1. I think that’s spot on.

      Provided you are not signing up for an egregiously expensive course, it has the potential to augment your earnings, and you’ve got the spare time, there’s pretty much zero downside here.

      Good luck!

    1. So I’ve never focused on monetizing this blog other than a bit of ads to cover costs.

      That being said, I did hear folks can do pretty well financially, which seems to be the case based on your and Sam’s comments!

  6. I loved this whole article, but the blogging section caught my attention specifically. I’ve been blogging for almost 16 years now. I feel I may have a unique perspective to add.

    When I started blogging it was easier to make money. After about the first year, I was making around $60K – not as good as my $100K software engineer career, but there was a lot less stress and no manager. Everything was great!

    After about 4 years (in 2010), Google changed its algorithms and almost all my blogging friends lost 75% of their income almost overnight. I did better than most, but it was still a big drop. Around this time people were spending more and more time on Facebook, the attention economy shifted to social media. With that change a lot of viewers and clicks did as well. The professional blogging organizations came in and introduced clickbait – further limiting attention to bloggers writing content with integrity in mind. As you mentioned in the article, there’s no barrier to entry, so of course other personal finance bloggers joined in (while many also went away).

    Lately, I’m making a little more than quarter of what I used to make blogging, a fraction of what I’d make if I continued my software engineer career. It’s not terrible because I need the flexibility now that I have kids and my wife’s military career doesn’t allow for it. My software engineering skills have atrophied to be of little use even in this job market.

    So, I wouldn’t say there’s no downside.

    1. Thank you – fantastic insights and very much appreciated as usually you only hear one part of the story (the rosy one).

      I guess where I was coming from is that if the time one spends blogging would be otherwise wasted on things like TV or social media, there’s no opportunity cost. That being said, I wouldn’t advocate folks giving up their day jobs for it (and certainly I’m not treating this blog as a money maker).

      Out of interest, how much traffic does your blog get these days?


      1. I used to think that time watching TV is wasted, but lately, I’ve grown to realize that such time is necessary to decompress. Aside from that, being able to reference certain things in pop culture helps connect with other bloggers and readers. It may depend on what your other decompression activities are. I could see sports as an healthier alternative, but I often don’t find too many leagues running at 10PM when the kids are in bed ;-).

        My blog traffic is around 20K a month lately. It’s been as high as 250K/mo. I don’t focus too much on SEO – it’s a lot of work to fight for spots on Google’s front page.

        There’s no moat when it comes to blogging so in a lot of ways, it’s a lot like being an Uber driver, but without the guaranteed money. In a lot of ways another system controls your earnings (typically Google, but it could be Facebook or YouTube if you build content on those platforms).

        Sorry to sound pessimistic. Blogging has helped me meet quite a few awesome people and it’s helped me pick up other remote jobs that have paid me over $200,000 easily over of the years. These ancillary benefits shouldn’t be discounted.

        1. Banker On FIRE

          On the contrary, I think these are great insights.

          There are some people who manage to do very well with their blogs, but you are absolutely right, it’s not the home run people represent it to be.

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