Trading like an Escape Artist: How I made money in October trading S&P Futures Options with 2x leverage

October was a scary month for stocks: the worst monthly S&P 500 return in seven years! And November is off to a volatile start as well! We haven’t even seen a real correction yet but apparently, the drop was bad enough for me to got inquiries from friends and former colleagues asking how I’m doing with our portfolio and if (and when?) I’m going to come back to the office again! Sorry, not anytime soon! As I detailed in the post two weeks ago, we are not too concerned about one month of bad returns early in retirement.

Some friends and readers of this blog were specifically concerned that my options trading strategy might have been hit badly by the wild swings. After all, I’m doing this with a little bit more than 2x leverage and with the market down about 7% does that mean we lost more than 14%? Of course not! To all the rubbernecks out there who suspect we had a bad car wreck in our portfolio last month, I’m happy to report that we actually made a small profit with this strategy in October! And continued to do so in November! How awesome is that!? Well, there were a few close calls but I was able to escape any major damage. It took some Houdini Skills (or luck???), hence the title image of escape artist Harry Houdini (Picture Credit: Lomography).

Let’s take a look at the details…

Continue reading “Trading like an Escape Artist: How I made money in October trading S&P Futures Options with 2x leverage”

Some of my Thoughts on Bitcoin and Cryptocurrencies

As a follow-up to yesterday’s guest post, here are a few of my own thoughts about the challenges and opportunities. For full disclosure, I don’t currently own or have ever owned Bitcoin or any other cryptocurrency myself. I reached Financial Independence (FI) years ago the old fashioned way with equities and a little bit of real estate. Only a few weeks away from early retirement, I have no need to throw “Hail Mary passes” with my money! But just because I’m interested in finance and technology I should have an opinion, of course, so here are some of my random thoughts in random order on Bitcoin and Cryptocurrencies… Continue reading “Some of my Thoughts on Bitcoin and Cryptocurrencies”

Passive income through option writing: Part 2

Last week we made the case for generating passive income through option writing. A quick recap of last week: buying puts to secure the downside of your equity investment is a bit like casino gambling: pay a wager (put option premium) for the prospect of winning a big prize (unlimited equity upside potential). Unfortunately, the average expected returns are also quite poor, just like when you gamble in the casino or buy lottery tickets.

Since we can’t beat the casino, let’s be the casino!

Being the casino means we act as the seller of put options. Let’s see how we implement this:

Continue reading “Passive income through option writing: Part 2”

Passive income through option writing: Part 1

On the path to early retirement (and most likely in early retirement as well), the ERN family will be writing options to generate passive income (in addition to equity and real estate investments, of course). This may be something that people either haven’t heard before or even if they did, they might be turned off by the involvement of derivatives. After we got over our initial aversion against trading exotic instruments like options we found that it’s actually a reliable and profitable strategy to generate passive income. We mentioned this strategy already in a previous post on trading derivatives on the path to FIRE and thought that others might find this interesting too.

Today, in Part 1, we will do a quick intro to cover mostly the conceptual aspects of this strategy. Part 2 will go into how we actually implement our strategy. As a warm up, though, let’s start with a …

Pop Quiz:

Since 2000, the SPY ETF (S&P500 index fund from iShares) returned about 101% (Dec 1999 to August 2016, dividends reinvested), or about 4.3% p.a. What would the return have been if we had participated only when the market went up, i.e., if we had avoided every single down month and received a 0% return during that time?

A: 386% total, 10.0% annualized

B: 1,039% total, 15.7% annualized

C: 2,497% total, 21.6% annualized

D: 3,891% total, 24.8% annualized

Continue reading “Passive income through option writing: Part 1”

Trading derivatives on the path to Financial Independence and Early Retirement

Derivatives and FIRE (Financial Independence and Early Retirement) sound like two things that don’t mix. Like oil and water. Financial derivatives (options, futures, etc.) have the aura of opaque and highly risky investments. On the way to Financial Independence, most people are either oblivious to derivatives or avoid them like they carry communicable diseases. Probably derivatives are also traded in some smoke-filled backroom or an illegal gambling joint, right?

Let’s look at the myths vs. facts! Continue reading “Trading derivatives on the path to Financial Independence and Early Retirement”