Passive income through option writing: Part 9 – 2016-2021 backtest: Guest Post by “Spintwig”

November 10, 2021

Welcome to a new post in the Put Option Writing Series. My blogging buddy Spintwig volunteered to perform another backtest simulation. If you remember from Part 5, he simulated selling 5-delta and 10-delta put options going back to 2018. He now added 18 more months of returns to go back to September 2016. In the end, I will also compare my live results with the simulated returns and point out why my live trading achieved even slightly better results.

Mr. Spintwig, please take over…

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Thank you BigERN (can I call you Dr. K?) for another opportunity to collaborate and add to the body of research that supports what is colloquially known as the “BigERN strategy.”

Part 8 of the options trading series is a 2021 update that discusses, among other things, premium capture, annualized return and the idea of lowering leverage while increasing delta.

Let’s throw some data at the idea of trading a higher delta at a lower leverage target and see how metrics like premium capture, CAGR, and max drawdown are impacted. As an added bonus, I’ve obtained SPX data that can facilitate a Sept 2016 start date for this strategy. This gives us an additional 18 months of history vs the SPY data that was used in Part 5.

For the benchmark, we’ll use total return (i.e. dividends reinvested) buy/hold SPY (S&P 500) and IEF (10Y US Treasuries), rebalanced annually, in the following configurations:

  • 100 SPY / 0 IEF
  • 80 SPY / 20 IEF
  • 60 SPY / 40 IEF

Let’s dive in…

Continue reading “Passive income through option writing: Part 9 – 2016-2021 backtest: Guest Post by “Spintwig””

Passive income through option writing: Part 6 – A 2018-2021 backtest with different contract sizes: Guest Post by “Spintwig”

All parts of this series:

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April 21, 2021

Welcome to a new installment about trading options. Alongside my work on Safe Withdrawal Rates, this is my other passion. In fact, on a day-to-day basis, I probably think about shorting S&P 500 put option much more than about Safe Withdrawal Rates. In any case, one of the most frequent questions I’ve been getting related to my options trading strategy is, how do you even get started with this strategy when you have a smaller-size account? Trading CBOE SPX options, with a multiplier of 100x on the underlying S&P index, even one single contract will have a notional exposure of roughly $400,000. I don’t recommend trading that without at least about $100,000 or better $125,000 or more in margin cushion.

How would one implement this without committing such a large chunk of money? 

My options trading buddy Mr. Spintwig who already published another guest post in this series offered to shed some light on this question. He ran some simulations for my strategy using some of the other “option options” (pardon the pun), i.e., implementing my strategy not with the SPX index options but with different vehicles with a smaller multiple than the currently pretty massive 100x SPX contract. For example, the options on S&P 500 E-mini futures are certainly a slightly smaller alternative with a multiplier of only 50. And there are some even smaller-size contract alternatives, but my concern has always been that the transaction costs will likely eat up a good chunk of the strategy’s returns. 

In any case, I’ll stop babbling. Mr. Spintwig has the numbers, so please take over…

Continue reading “Passive income through option writing: Part 6 – A 2018-2021 backtest with different contract sizes: Guest Post by “Spintwig””

Passive income through option writing: Part 5 – A 2018-2020 backtest: Guest Post by “Spintwig” (plus a quick update on last week’s volatility)

All parts of this series:

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June 17, 2020

Welcome back to another post centered around Put Option Writing. Today we got a real treat because my blogging buddy, fellow option trader and frequent commenter “Spintwig” offered to do a guest post to perform an independent review of my trading strategy. If you don’t know Spintwig, he also retired in 2018 (at age 30!!!) from a career in ITnd now writes about FIRE and options strategies at his blog. He does a lot of interesting and important work, including careful and comprehensive back-tests of different option trading strategies, i.e., different underlying assets, different Deltas, different horizons (days to expiration), etc. I highly recommend you check out his work if you’re interested in option writing!

Oh, and following the guest post, I’ll also give a quick update on how my portfolio did during the crazy,  scary volatility last week! Stay tuned!

Over to you Mr. Spintwig…

Thank you BigERN for the opportunity to peer review your options strategy and publically share the results with you and your readers. I’ve relied on your research in my own journey to and through FIRE and I’m happy to be able to add to the discussion and body of research.

A few years ago I stumbled upon BigERN’s blog as I was researching safe-withdrawal-rate topics. Among the material was a novel idea: selling put options on the S&P 500 index could mitigate sequence-of-return risk.

The concept was straightforward but I wanted to know if there was an optimal approach or if it could be applied to other indices and have similar results. Would it be advantageous to replace a traditional buy-and-hold portfolio with an options trading strategy? Unfortunately, there were no definitive or trustworthy answers to this question on the internet so I set out to do my own research and publish what I find.

Continue reading “Passive income through option writing: Part 5 – A 2018-2020 backtest: Guest Post by “Spintwig” (plus a quick update on last week’s volatility)”

Guest Post: Should you invest in Stocks or Bitcoin?

Hard to believe that this blog has been around for almost two years and I never wrote anything about Bitcoin and Cryptocurrencies. I will have some more of my own thoughts and comments in tomorrow’s weekly Wednesday post but to set the stage, our online buddy Matt Paulson has agreed to write a guest post on the topic. Matt runs a site called MarketBeat which is pretty neat. It has a lot of free information, including all the interesting stats on earnings history/forecasts, dividend history, SEC filings, etc. for individual stocks. I don’t think I have seen all that information aggregated so nicely anywhere else, see below:

MarketBeat screenshot.png

In any case, here’s the guest post on Bitcoin, take it away Matt…

Bio: Matthew Paulson is the founder of MarketBeat, an Inc. 5000 financial media company that empowers retail investors to make better trading decisions by providing real-time financial data and objective market research.

The stock market continues to soar, reaching new highs on a regular basis. Many people attribute this to the brighter macroeconomic outlook, lower taxes and less regulation, so markets find it easier to price future expectations. This has led to record highs for both bitcoin and the stock market. However, individuals need to be careful when making an investment. Although bitcoin may appear to be the wave of the future, we need to understand the benefits and drawbacks of both stocks and cryptocurrencies to ensure they make the decision that is right for their unique needs. Continue reading “Guest Post: Should you invest in Stocks or Bitcoin?”

Guest Post: Why geographic arbitrage is so important to retire early and what you can do to about it

Today we feature a Guest Post from my blogging buddy Benjamin Davis. A very exciting and important topic: Geographic arbitrage! Benjamin holds a Ph.D. and decided to become a landlord to retire early. He writes on From cents to Retirement, a blog about early retirement and real estate investing. He also wrote the book My strategy to retire early and runs a real estate and investment consulting business in Portugal. His goal is to build a real estate portfolio with 100 units before he turns 35 and turn From Cents To Retirement into a reference blog for early retirement through Real Estate investments, while he inspires others with his own story. Take it away, Ben!

I was born in Portugal and divided my childhood between Portugal and Italy. I lived in Canada and Germany after that. My family is Canadian and Italian so you can imagine how much I have been exposed to different cultures.

When I decided I was going to retire early, I needed to select the country I was going to live in. I decided to move to a country that would allow me to take advantage of geographic arbitrage, which is defined as the practice of taking advantage of different prices and tax rates in different markets.

There are multiple reasons why I selected Portugal. It would be very easy to talk about the food, the weather, the overall quality of life, etc. But this post is to talk about the financial aspects of this decision. Continue reading “Guest Post: Why geographic arbitrage is so important to retire early and what you can do to about it”

The Other Student Loan Crisis: Half of Parent Cosigners Facing a Shaky Retirement

[It’s a pleasure to introduce Laur (Lauren) Davidson today. Laur is a senior at the University of Pennsylvania majoring in English and Communications. She wants to build a portfolio as a freelance writer and agreed to write a guest post for us – perfect timing because the ERN family is on vacation this week! The post is on a very timely topic: student loans and how they threaten even the parents’ finances if they cosigned their kids’ private student loans. Take it over from here, Laur!]

Half of Parent Cosigners Facing a Shaky Retirement

By Laur Davidson, a soon-to-be graduated freelance writer for hire

The sheer magnitude of the mountainous $1.4 trillion of debt weighing down 44 million Americans is rightfully grabbing headlines as a looming financial crisis. The devastating economic and social impact of student loan debt on borrowers, their families, the communities in which they live and the nation is well documented. Less known, but no less devastating is the impact student loan debt is having on well-intentioned parents who are suffering financially for having helped their students by cosigning their private educational loans. With the number of students unable to repay their private loans increasing each year, more and more parents are having to rethink their retirement plans.

Continue reading “The Other Student Loan Crisis: Half of Parent Cosigners Facing a Shaky Retirement”

Five Unfortunate Facts about Student Debt in America

Our first guest post on the ERN blog! Ever! Let me introduce Drew Cloud who runs the fascinating blog studentloans.net. Not too long ago, I remember U.S. student loans surpassing one trillion dollars (a one with 12 zeros!) for the first time. Now we’re at $1.4t and the amount just keeps growing. Make sure you check out Drew’s blog, too, especially the treasure trove of data on the topic. Take over, Drew!

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A quick online search of student loan debt in America reveals the astonishing truth about the widespread, increasing expense of attending a college or university. Currently, more than 44 million borrowers have amassed over $1.4 trillion of student loan debt, and each year, the total continues to climb. While taking out student loans is now firmly embedded in the college experience for the majority of students, the picture remains bleak for borrowers. Here are five unfortunate facts about student loan debt in America to prove that point.

StudentLoanChart
Student Loans Owned and Securitized, Outstanding. Source: Federal Reserve Bank of St. Louis.

Continue reading “Five Unfortunate Facts about Student Debt in America”

An addition to the ERN family portfolio: Preferred Stocks

Last year in December we noticed that one of our Municipal Bond mutual funds had short-term losses. That’s not a huge surprise after the post-election bond yield surge and hence it was time to harvest those losses. If you’re not familiar with Tax Loss Harvesting, we wrote two earlier posts on the topic, one dealing with the general concept and one dealing with the implementation. In any case, after we sold the underwater tax lots, where do we put the money? For 30 days we can’t invest in the same fund (or different fund with identical benchmark) or we’d run afoul with the IRS wash-sale rule. There was one asset class that we had never owned but had definitely been on our radar screen for a while. Finally, we took the plunge and invested in… drumroll …

Preferred Stocks! Continue reading “An addition to the ERN family portfolio: Preferred Stocks”

Guest Post on Budgets are Sexy: My Top 7 Disagreements With Personal Finance Experts

J. Money, the personal finance blogger who runs Budgets are Sexy and RockstarFinance asked yours truly to write a guest post! Wow, what an honor! And, it turns out, this is actually my first guest post ever (not counting the “Christopher Guest Post” on the Physician on FIRE blog two months ago because that’s actually an interview). What did I write about? Initially, I proposed to go on an all-expenses-paid trip to Tahiti to review some luxury resorts and report back, uhm, some time later this year. But J$ had another brilliant idea: write about my favorite finance pet peeves. And it got published today:

My Top 7 Disagreements With Personal Finance Experts

Of course, to read it all, you’ll have to head over to Budgets are Sexy. But please see below for supplemental material, i.e., some of our blog posts on the seven topics:

  1. Safe Withdrawal Rate:
  2. Robo-Advisers:
  3. Emergency Funds:
  4. Bonds to diversify equity risk:
  5. Bond vs. Stock Risk:
  6. Cash as bear market insurance:
  7. Tax loss harvesting: