Tibet to California – 9 Investment lessons from Cycling the World

What Cycling the World taught me about Investing

Kotomi's heaviest setup over the 12-month adventure allowing for a few days' of independent cycling without supplies (High Atlas Mountains, Morocco). Source: BoW Instagram Profile (Click to view)


One of the biggest misconceptions and most frequent questions that people ask long-distance cyclists is whether they’re lonely.  The fact is, these type of adventures are some of the most exciting and enriching human experiences you can have. 

However, you inevitably end up on your bike alone with your mind, music or audiobooks. There is lots of time to think/process experiences and lessons. You learn much about yourself and your limits

A couple of things have parallels in the Investment World. I tried to make a link to better understand the bigger picture. It’s also one of the reasons I started this blog and some of these experiences profoundly changed my way of looking at investing.

You may think that spending over a decade on Wall Street would teach me more than cycling. As I wrote, technical knowledge needs to be combined with perspective/wisdom to produce results.

Here are 9 lessons I learned.

#1 You only race against yourself

From Tibet to Busan, Korea

In Korea, I cycled trough the ‘Seoul-Busan’ Four Rivers cycling trail (Korean cycling infrastructure is mind-blowing and can only be compared to a couple of European countries) with a Russian world cycling fellow – Dimitri. The ‘problem’ was that I was at the top of my (personal) game at that point. Dimiti wanted to challenge me but didn’t realize the initial conditions were heavily skewed in my favor. 

I just flew from China where I spent a few weeks cycling in Tibet at an average altitude of 3,200m (10,500 feet) above sea level. My lung’ capacity and red blood cell count must have hit ATH (all-time high). Even with more luggage (I had 20 kgs of luggage on top of my 11kgs gravel bike) the race was uneven. 

On the other hand, I wasn’t able to compete with some cyclists outside Taipei, in Taiwan, after an injury or when conditions were not favorable for me. The days I choose to challenge myself, I try to keep in mind to improve my capacity vs. myself yesterday not vs. others since we’re never fighting the same fight.

Investment Portfolio Impact

Assess your risk tolerance and personal life circumstances – your dreams and projects. They, and you are unique. Don’t compare your portfolio performance with someone else that took more risk, because her/his life situation may be completely different. Here is an example of how detrimental it can be to have a wrong assessment of your risk tolerance.

#2 Crashes are bound to happen

Broken ribs in Okinawa, Japan

While trying to avoid any events that would stop the adventure you nevertheless end up with mishaps. I had two major crashes in Okinawa, Japan and Rabat, Morocco. 

I managed to recover in Taiwan where a friend I met in Hokkaido hosted me for a couple of weeks while I was recovering from my broken ribs (what an amazing experience to be hosted by a local family and learn so much about Asia’s complex history and Taiwan’s hidden cycling gems). 

In Morocco, the crash left me unable to cycle much longer.

Investment Portfolio Impact

Investing, like cycling is a risky endeavor. You can minimize risks but you won’t avoid crashes, because factors causing them may be totally outside of your control. 

Prepare your portfolio for the worst as it will hit you when you least expect it e.g. Inflation – while very remote in today’s world and equities may hedge it, what if Equity Bear Market and Inflation come at the same time?  Do you have assets that will perform well in a prolonged deflationary scenario? Try to be as antifragile as possible. 

While this may not always be the case in cycling, there are ways to deal with a market crash when it happens and even take advantage of a recession

#3 Anything that can go wrong will go wrong

Murphy's Law from Tasmania to Mount Fuji

What you may have remembered from the Interstellar movie is valid in cycling, too. Murphy’s law doesn’t mean that something bad will happen. It means that whatever can happen, will happen 

When I started my trip in Tasmania, Australia (a cycling paradise with an ‘edge of the world’ feel to it) I didn’t quite know that everything on a  long distance cycling trip needs to work perfectly fine. 

Or rather ignoring even the slight misconfiguration of your setup will inevitably have consequences. A satisfactory setup was enough for my trips in Southern Europe but once I started cycling hundreds, then thousands of miles through Australia and New Zealand I hit a major issue near Mount Fuji in Japan.

My knee started hurting with every pedal stroke. Tiny changes in your setup will break your body. The same applies to mechanical issues. You need to think about all possible things that can go wrong with your bike e.g. if you don’t have that backup screw that goes missing in the middle of the Alps in New Zealand. 

Investment Portfolio Impact

Small things in your investment process may accumulate and have material an impact over time: (i) do you have an emergency fund to avoid liquidating Stocks during a crash? (ii) do you know how to select an ETF to be cheap and tax-efficient to avoid leakage of cash?

Taiwan - Cycling heart of Asia. Source: BoW Instagram Profile (Click to view)

#4 Ego is the enemy

Vipassana Meditation in British Columbia, Canada

I came to know about Vipassana from a friend from the Financial Institution we both worked for. As a cycling traveler, experiencing meditation through Vipassana seemed like a good option (and a good opportunity to take a break from cycling)

One of the lessons from these tough sessions is that Ego is your enemy.

It taught me one great lesson – I needed to define myself outside of my career. A lot of people in finance struggle with identity, and even if they aim for Early Retirement, they are secretly scared of the idea of being stripped off the status and prestige that comes with their job (much more than the money). 

Investment Portfolio Impact

You may think that you have an edge over other investors but ask yourself the question — am I more qualified than a professional investor to predict which industry player may outperform the rest of the market? 

Do I know how the landscape in a few years will look like? Even if you suspect knowing first-order effects are you sure of the second and higher-order effects? (that can outweigh the first-order effects on prices).

Simple is powerful. Why not trying a Golden retriever portfolio?


#5 Best things happen in the most unexpected places

Exceptional hospitality on the West Coast, US

The beauty of travelling on a bike is reaching destinations and people  you wouldn’t normally have access to. You inevitably gain faith in humanity since you receive help on a daily basis (in North America I was hosted by different locals, every day, 3 weeks in a row!) which is a whole different experience from a hyper-competitive cut-throat Wall Street environment.  

Just a few weeks ago I received a message from a friend that hosted me in Iwate Prefecture, Japan. It was the anniversary of our campfire, where I arrived by midnight exhausted after a long day on a bike and he offered me some dinner. 

The number of connections you make on such a trip is unbelievable  and the depth of conversations incredible. Magic happens off the beaten path. I am immensely grateful for all the help I received. That’s why I also started this blog, to pay forward some of the kindness I received. 

Investment Portfolio Impact

Don’t overengineer your portfolio where you don’t have an edge. Rather, use steps to simplify your portfolio from assets you don’t need.

But there are parts in your life where you may have a massive competitive advantage. That Real Estate business or Start-up could be one of them. 

These underrated places are where wealth is made. Stock market is a powerful passive money-making machine that can be used to compound wealth but, unless you have an edge, don’t expect your performance to be vastly different from someone taking similar risks. 

#6 It's not about the bike

Pareto Principle on the road

I have a Canyon Ultimate bike back in Europe, that I bought back in 2018 following the advice of other more experienced road cycling colleagues. But I now much rather ride my gravel bike that is 5x cheaper. And performance-wise, the difference is not massive. 

Pareto principle states that you can achieve 80% of results with 20% of efforts. The same applies to bikes. 

Investment Portfolio Impact

Define your goals but try to contain them to what really will help you being happy. After spending years in luxury hotels I rather use my tent on a beach in Hokkaido. 

While this is oversimplifying things, you may not need much to retire early and achieve happiness

Hokkaido, Japan. Source: BoW Instagram Profile (Click to view)

#7 Luck favors the prepared mind

No preparation can time the pandemic


Luck has played an enormous part in my adventures and I recognize it. My timing to start the trip a year before the COVID-19 pandemic struck was pure luck. Some unlucky cyclists resigned from their jobs at the start of 2020, gave notice to their landlords just to be stuck without a job for next few months. 

I will look with gratitude at the ability to cycle some during what may be historically looked back upon as the peak of globalization with all its advantages.

There were even more crucial random events that contributed to my trip. We can maybe talk about them, if I travel near your place and we meet one day for a coffee. 

But preparation wouldn’t have helped me. In Investing though, it may. 

Investment Portfolio Impact

In 1854, Louis Pasteur coined the expression ‘Dans les champs de l’observation le hasard ne favorise que les esprits préparés’ – Luck favors the prepared mind. 

I wrote why, despite low interest rates and return expectations for Equities, Wise Money Investors will end up riding the next bull market and become millionaires

In investments, without proper education you won’t be able to seize opportunities and Financial Education to set up your portfolio goes a long way

But in active investing you may have to be more careful. Trader’s long term survival rate in the industry is c. 10%, do you think you are part of them? What if luck, not skills determines most of the winners? 

#8 It's about the journey

Carpe Diem

I recently spoke to a friend who is a semi-pro cyclist (yes, the guys that do 500 km or 300 miles in a single day). 

He told me that what was striking is that he heard from Tour de France participants never having the time to look around when they cycle and enjoy anything of it.

There is a French expression borrowed from cycling,  avoir la tête dans le guidon which could be translated into keeping your head between the handlebars. Literally.

A Japanese cyclist, Aya, was telling me in Okinawa how she regrets having cycled Japan from Kyushu to Hokkaido only to realize that the journey should have been slower to really make the most of it. 

Investment Portfolio Impact

Having a goal, like Financial Independence or Early Retirement is a great source of motivation. 

Destination may matter most for Tour de France cyclists. But let’s not forget about the journey – while I adhere to the FI aspect what motivates me more in my current situation are mini-retirements. 

Objectives vary a lot based on personal circumstances but I try not to neglect the fact that my most precious resource is time 

#9 Getting out of the comfort zone

From hills to 3,300m mountain in Taiwan

People often ask me how much do you need  to train before going on a world cycling adventure. Well, not much. I started cycling in 2017. While I was busy analyzing deals in southern Europe I used the opportunity to stay over the weekends and cycle some of the best European cycling regions. 

Some of my favorite spots include Sa Calobra (Mallorca), Col de la Madone (South of France) or  Cap Corse (Corsica). I never cycled more than a couple hundreds miles during a weekend before embarking on a World cycling adventure.

The same applies to climbing hills and mountains on a bike. I started with steep, small hills in the UK and my longest day yet was climbing from Sea Level to a peak altitude of 3,300m (11,000 feet).

The most difficult part was to leave finance for a year or perhaps much longer, which seemed scary given the uncertain world we live in,  and have no expectations about my next 12 months. I write quite often about Stoic philosophy.  The above framework, which is based on Stoicism, helped me when I decided in Autumn 2018 to go on my biggest adventure yet (needless to say, it was one of the best decisions I’ve ever made)

Investment Portfolio Impact

Just start investing. Even if the market is currently at all-time high – which may seem scary. So is buying the market when the Index falls 10% in a single day.

Invest small chunks over time, if that can help. What matters is to acquire knowledge and then take the plunge. Small steps and persistence will pay off and in the long run you will be rewarded.

Read how to start investing and then construct your Long Term Investment Portfolio

Good Luck & keep’em* rolling!

(* Wheels & Dividends)


(Top 9 Roads, ex-Europe, I would ride again tomorrow)


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About Raph Antoine 77 Articles
Raph Antoine is a Portfolio Manager and Institutional Advisor that witnessed first-hand the 2008 Global Financial Crisis and the 2011 European Debt Crisis working for some of the most prestigious names in the financial industry. Raph has experience across multiple asset classes including Fixed Income and Equity products as well as bespoke Investment vehicles in multiple jurisdictions. Raph holds an MSc in Financial Engineering and is a CFA (Chartered Financial Analyst) Charterholder. He usually rides one of his two bikes. Rarely, a Canyon Ultimate CF SLX 8.0 (that is currently in family's attic) and most of the time a Gravel Pinnacle Arkose (his favorite) that he used to Cycle the World.
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11 months ago

Great article. I am more interested in investing in stocks. But how do you think VTI, VXUS, BND or the right choice of ETF should you add more to any different ETF. Let’s say 60 percent hold only Stocks and everything else in an ETF.

10 months ago
Reply to  Raph Antoine

I have several company stocks that I bought through a US broker and also added a vxus ETF because I want to separate. US and ETF. You are right. But I’m thinking of moving to an EU broker. 

11 months ago

Such a great Blog – fantastic take-aways!

11 months ago

Great website and lots to learn about Investing here, love the cycling references too.

tim clare
tim clare
11 months ago

Hey Raph, I particularly liked #6… what sort of gravel bike do you ride?

tim clare
tim clare
11 months ago
Reply to  Raph Antoine

Thanks Raph. I must agree about Asian manufacturing… in the 70’s it was ‘Jap-crap’ just because of… well xenophobia really. Now we accept the Asians lead the field for quality at price.

11 months ago

you had me at Tibet. And then so much to learn – getting out my comfort zone is one I’ve been fighting lately – especially with a baby. Subscribed and following now on.

Court @ Modern FImily
11 months ago

Great post! Love all the similarities.

Dividend Power
11 months ago

I like your bike ride tour and investing tour perspective. It’s a very unique way of looking at investing.

10 months ago

Just found your site and reading up – thanks so much Raph!

You need a whole section on biking in the future 😀 I’m interested in how you plan some of these trips since I’m a casual cyclist (50kms max) and the thought of forgetting something makes me sweat…