Influence of Dungeons & Dragons on my investment style.

The daddy of all role-playing games has turned 40 lately.

I'd just like to share the influence Dungeons & Dragons have on my life.

I picked up D&D when I was 10. I started out with the D&D Action figures by LJN ( I used to have Warduke the Fighter and Strongheart the Paladin ) and was told by a senior in my primary school that there's such a thing as a role-playing game. Being a spoiled brat that I was when I was a kid, I was able to got to a place called Leisure Craft at Orchard Point to buy the 1st Edition Player's Handbook ( Yes, I started with AD&D, BECMI is for wusses ). It took me a while to really understand the system and I was only able to start DMing a game for my classmates a year later ( I think it was a Dragonlance module ).

Here's what D&D taught me :

a) Delayed gratification can get you anything you want. 

I remember when Oriental Adventures came out, Leisure Craft charged a whopping $32 a copy. Even though I was a spoiled brat who had $15 pocket money a week, I had to starve myself for 3 weeks before I could get it.     

I think this trained my willpower to delay my spending. At my current stage, I can delay gratification for decades.

b) Arbitrage and Securitization is awesome.

I remember trying to get hold of a Dungeon Master's guide was problematic as I already had the Player's handbook, Unearthed Arcana and the Monster Manual. I suddenly has a bright idea.

My dad's friend who was an old coot, collects copies of Playboy magazine. Somehow, being a corrupt kid, I asked him and he give me a copy because I was curious about human sexuality. My idea was to cut out pictures of the nudes and I sold them individually to kids from Whitley Secondary school (which as next door to my secondary school). I remember getting $15 for a pic of Madonna ( yeah, she did porn ! ) I think my senior in St Johns caught me making the trade but thankfully nobody reported me. 

At the tender age of 13, I was able to make a riskless gain (arbitrage) by splitting an asset in multiple components ( securitization ). If I was'nt caught by my uniformed group, I think I would be with Goldman Sachs today.

Of course, on hindsight, vintage pics of Madonna naked would be worth a lot more $15 these days. But what's a naked picture of Madonna compared to brilliance which was the 1st Edition Dungeon Master's Guide ?

NB:  And that senior who caught me might have become an auditor, go figure. 

c) All the advanced maths and vocabulary for the SATs at the age of 10

D&D is not a game for dumb kids. I learnt about the bell curve from the DMG and basic probability from rolling polyhedral dice. By the time I did my SATs during my JC days, I was able to get 96+% for my SAT Verbals. Needless to say, having advanced mathematics allowed me to ace my S papers and even got to an IT Olympiad training team. 

Eventually, maths was critical to passing CFA 2. 

d) Dividends investing

I was instinctively able to grasp dividends investing because of D&D trolls. You see, trolls are monsters who regenerate. If you strike a troll and did less damage than its regeneration, it is the same as not doing dmaage to it. I always thought that trolls would particularly like getting dividends because if the incoming cashflow exceeds the damage or your expenses, you will never be defeated by the monster called Modern Living. 

Just be careful of fire or acid attacks.

e) What the rules did not explicitly say that you can't do.

The most important lesson I learnt from D&D was much later during my JC days. I joined a group of pretty insane players and there were all sort of crazy RPG antics which was suited to a different kind of blog. One wizard Stoned to Flesh dungeon walls, fireballed the flesh and told the fighters to eat their way through their rooms. He also cast an Item spell on various undead creatures to shrink them into a cloth-like state and threw the resulting "skeleton-dolls" on party enemies. The druid fire-trapped his mouth and bit his enemies. The fighter has boots of flying and attacked monsters by dropping a Daern's Instant Fortress (10d10 damage, like Mjolnir ) on them. 

In between game sessions, my fellow players told me that one way to play D&D is to simply follow the rules. But they played the game differently. They did things which were not explicitly prohibited by the rules. Very often, they interpreted the rules in hilarious ways. ( eg. Any closeable item can be firetrapped. A mouth is a closeable item. )

My DM called them rules-rapists, they went further than any rules lawyer from other RPG groups. 

I think playing D&D with this group had the most profound influence on my life.

• There is no law in Singapore that say that Engineer's can't write a bestselling non-fictional work.
• There is no law in Singapore that say that you can't create a perpetual cashflow to replace your living expenses.
• There is no law against 8.5% portfolio if your risk appetite can handle it.
• There is no law against reinvesting 150% of earned income to ramp up your cash flow. 
• There is no law that says that you can't work and earn one income and supplement your expenses from another source of cash flow. 
• There is no law in Singapore that say that you can quit the rat race at 39 to reinvent yourself.