First, let’s be clear: I am not a finance guy. I have no finance training, nor have I worked in the industry.
Nonetheless, this blog will be about investing in the capital markets. Given the above, why bother? Good question. Well, I want to be one of cool kids too, obviously. More importantly, someone wise once said that if you want to grow as an investor and meet smart people to help you, write up your ideas and release them into the wild. So that is what I’m doing. In my experience, it is never a bad idea to share your work; only good comes from that. And just the process of writing up your ideas forces you to collect all your thoughts and distill them down to the simplest story that defends your thesis.
A little about me then. I’m an old guy. A couple degrees in physics a long, long time ago. I spent most of my working career in software. Started a dotcom … yada yada yada … eventually retired at 38.
I initially ran my home office as a fund of funds. I had little interest in trading myself, so sought out managers to run my money for me. I researched funds, found strats I liked, ran all manner of statistics on past performance, interviewed managers … I worked pretty hard at it for a decade. Nobody I found could outperform for more than 5 years, and eventually I got tired of paying managers 2 & 20 to lose me money.
So in 2019 I took the proverbial bull by the horns and started managing all my own money. And it was terrifying. At first I’d get pretty excited when a stock moved $1000 one way or another. Seems so quaint in hindsight.
I started with 100% technical trading. It worked, but I didn’t enjoy staring at charts for hours on end. As I was mostly a breakout trader, I’d end up max short at market bottoms, and max long at tops. I consistently made money, but regularly gave back lots of gains. Vol-adjusted returns were disappointing. I believe there is something to “technicals”, but I also believe the signal/noise ratio is much lower than proponents might suggest. I found the process thoroughly unsatisfying.
Over time, and lots of experimentation, I have evolved into what I think of a “degen investor”. To find an edge, I go where others won’t or can’t, and that typically means buying stuff that makes you uncomfortable. Think politics (eg: ESG/fossil fuels in 2020), cyclicals (shipping), illiquid ($EVO.AX), cheap with hair and lots of upside ($ASPI). My friend The Blind Squirrel could only laugh when I admitted to buying 14% IRR Cayman-listed bonds for a Cambodian casino. It will surprise no one who knows him, that Rupert was intimately familiar with the capital structure of said casino.
These bets I make are often glorified perpetual option trades: very asymmetric upside, but with gut-wrenching downside. “A 10x or a doughnut” is a common theme of my trades. I think these trades can offer excellent expected value, but you damn well better get position sizing right. No full porting allowed. It is this aspect of how I approach the markets that is the inspiration of the name of this blog: I absolutely traffic on the spicy side of the markets.
Anyway, enough about me. I’m not doing this because I’m brilliant or am especially good at this game. I’m here to share my work, as faulty as it may be, in the hope that:
Somebody finds it interesting or valuable.
Readers tell me what they think.
I’m really hoping about #2. Comments here or on X. Please let me know what you think and why I’m wrong.
Whirly.
No posts

Comments
Nothing yet. Say the first thing.
Sign in to join the conversation.