[Trade Feed] @Mathematical Money: 382% RoR via Options Trading & Portfolio Sizing

@Mathematical Money is a rising Star Contributor in the Tiger community, with nearly 10k followers, thanks to his valuable trading insights. He specializes in strategies like cash-secured puts, covered calls, and strangles, focusing on high-yield stocks with strong fundamentals. Using a simple Excel sheet for portfolio management, he emphasizes that proper position sizing is more important than stock picking or timing, helping to achieve outsized gains and reduce emotional decision-making.

Currently, he has achieved a Rate of Return of 382% over 3.6 years, and obtain a profit over $500K USD trading crypto stocks in 2024.

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Briefly introduce yourself, share your personal investment growth experience, and how you made your first bucket of gold in the market?

Hi everyone, Mathematical Money here. To be honest, I used chatgpt to come up with such a name. Just ask chatgpt to suggest a name where my trading habit is largely based on probability and math. They gave me some stupid names and this is the most decent one I got.

I am engineer by training and started my career in the harsh environment of the shipyards. I’ve been lucky to meet great bosses who exposed me to the financial and business aspects of the businesses. I was able to pick up accounting skills in this job, and I became part of the team sourcing for deals, evaluating deals and making feasibility studies on proposed deals. With the exposure in these areas, it sparked my interest in investing in companies to generate “income” for me rather than working for money.

I started my earlier days in short term trading in stocks and forex trading. There was not much consistency for many years until I started buy and hold strategy. Even then, I was not able to generate consistent income as most of our time is “waiting” for stocks to realise its potential value.

During covid, I started learning options trading with a few friends and we found it much easier to manage our entry/exit and emotions. With options, which is now the majority of my transaction volume, our P&L curve is smoothened out to have less spikes and dips.  


What is the most impressive investment experience you have had?

The 2022-2023 downturn was one of the best lessons we’ve had. It was a time where everything will continue to go down no matter what kind of quality stocks you have picked. The impact that money supply, interest rates and money market funds have on the market no matter how strong the individual company/stock is. At this point in time, do not fight the market, you can only take what the market gives you. Everybody is a guru during bull market, but the only guru is the one who can manage a bear market.

Are you trading full-time?

Nope. Actually this is just hobby, and I'm working full time. It's a group of ex colleagues, trying to encourage our friends to trade with us. We just share knowledge and trade together because we believe this is the only way to freedom.

Regarding the team you mentioned, how do you assign the team’s task to each member?

We don't really have a task. but each of us specializes in an area of the market, like china stocks, tech stocks or REITS. We put our thoughts in the group and have free discussions, but we monitor each other to make sure we do not leverage. We don't monitor that much things, just follow a plain excel for portfolio management. Focus on the few high yield stocks with proper fundamentals. Simple as that. 😆

You have been trading numerous cryptocurrency stocks recently, what’s your opinion in this sector? And what’s your thought on Bitcoin’s subsequent trend?

My trades in 2024 are predominantly on crypto for a few reasons. Firstly, believe USD will continue to depreciate because of excessive government spending (but this may change when DOGE is being setup). Secondly, interest rates are expected to fall which also would bring down the dollar's strength. Third, Bitcoin 4 year cycle indicates halving is in 2024, which normally a bull run will follow. That would already support the prices of crypto currency. maybe just to add. We believe it is important to be cautious going into 2025. The stronger the bull we see, the more drastic the drop. We are still cautiously bullish but we hope our followers will cut when they need to cut.

Can you briefly describe your overall options trading strategy? How do you determine the optimal strike price for options?

Mainly cash secured puts, covered calls and strangles. We try to keep to the basics and not go for the fancy stuff like Iron Condor or Butterfly. Strike prices are guided by our own set of deltas and gammas, support/resistant lines and also the bid/ask spread at that point in time.

You mentioned you follow an Excel for portfolio management. Can you elaborate on it?

Our summary page consist of this where it shows the outlook of options expiring every week for next 4 to 6 weeks. Also our target premiums per month based on the options we sell.

The page "portfolio" is the one that the beginners use. Easier to understand and lesser parameters for tracking. Basically we believe portfolio management and sizing are a big part. Much more important than picking the right stock and timing. Sizing it properly allows you to have outsized gains and remove emotions.

What factors or indicators do you rely on when deciding to enter or exit an options trade?

The beauty about options trading is the expiry of options are pre-determined. Hence, exits are mostly due to expiry or assignments. Unless we need the liquidity in somewhere else of the portfolio, we normally do not close the options early.

Entry is usually assessed with quite a lot of factors such as macro conditions (interest rates and money supply), technical charts (basic support/resistant lines and RSI), then finally the fundamentals of company (forward earnings, cash availability and business potential). Once I lock in on a specific counter, we normally don’t switch around too often and stick to the same few counters for quite a few months at least.

Patience is the key in investing and our way of using options is just to ensure we have cash flow while waiting for the stock to pick up momentum.

How do you select stocks and what is the one or few things you focus on a stock?

First few things that will enter our search would be, 1) Market Cap of minimum size of the underlying asset 2) Liquidity of the stock and options 3) Cash holdings 4) Potential tailwind in the business/industry. One of the few things we try not to look at also is the historical price of any stock. Quite a lot of people would always look at the historical high and lows of each stock, but that to us is almost irrelevant as it only puts on emotional baggage to the trading mindset.

What has been your biggest challenge or mistake in options trading, and how did you learn from it?

The biggest challenge is managing emotions and one of the most common mistakes that I will still make sometimes is entering a trade due to emotions. In order to reduce these trades, we have a trading journal that we check on each other regularly. So that we stop ourselves from making emotional trades!

If you were to use one sentence as a slogan to get people to subscribe to your Trade Feed account, what would it be?

I have always had people telling me high % RoR are because of huge risks in my trades. Of course, all these come with a certain amount of managed risk and there will be no investment without risk. So I would say “Extraordinary RoR with properly managed risk!”


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# Star Sharers Interview

Disclaimer: Investing carries risk. This is not financial advice. The above content should not be regarded as an offer, recommendation, or solicitation on acquiring or disposing of any financial products, any associated discussions, comments, or posts by author or other users should not be considered as such either. It is solely for general information purpose only, which does not consider your own investment objectives, financial situations or needs. TTM assumes no responsibility or warranty for the accuracy and completeness of the information, investors should do their own research and may seek professional advice before investing.

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  • JediGingerNinja
    ·12-15
    TOP
    could the tiger community itself be a think tank and executors of similar results as mathematical money and his crew have shown? suddenly retail is smart money [Miser] [Cool] [Silence]
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  • pekss
    ·12-15
    TOP
    @Mathematical Money I’ve been your follower / subscriber for months. Thanks for your sharing your investment philosophy! In your options trading, are you more focused on trading for income from options premium by selling options or capital gains? Have you considered futures as well? @Healthy Tiger @eveev
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  • LiverpoolRed
    ·12-15
    TOP
    Wow. U are much well better than me in options trading. I also just learn to trade options 3 years ago. I find this trading is a good tool to generate passive incomes. I had followed u for quite sometimes. Do you normally exit your options earlier or wait till it expire?
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  • Optionskiwi
    ·12-16
    TOP
    For the sold puts - what is the typical days to expiry and how far out of the money are the strikes?
     
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    • Mathematical MoneyReplying tosingsongone 10
      wow. didn't know that. really honoured. 🙏
      12-16 17:27
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    • Mathematical MoneyReplying toOptionskiwi
      I find weekly too short, hence having the strike price too near the underlying. I find 4 weeks easier to manage. personal preference i guess
      12-16 17:23
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    • Optionskiwi
      Thanks
      I’ve been selling with 0.2 delta but only weekly options just before earnings
      12-16 15:14
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  • Aaronykc
    ·12-16
    TOP
    Congrats on your success bro . I’ve been following you for a long time. Same as you the hardest part about trading is mastering my emotions, I still have not done it successfully so I’ve reduced the amount of trades and only take the high conviction ones. What’s your strategy for mastering your emotions? @TigerEvents @港股窝轮Jenny @Big__Boss
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    • Mathematical Money
      can try joining a group of like minded people or having a mentor. should help quite a bit.
      12-16 20:17
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  • koolgal
    ·12-16
    TOP
    @CL_Wong @MeowKitty @Derrick_1234 @Thonyaunn @CMLeong @rL @AlpineSnow @GoodLife99 please check out this interesting post on @Mathematical Money successful  investing journey and win some Tiger Coins too. 😍😍😍
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  • apgunner
    ·12-16
    TOP
    Amazing story, looking forward learning from your post and i also wonder how did you manage through the 2021-2022 drawdown? Thanks!
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    • Mathematical Money
      by position sizing and really have most of the cash on the sidelines.
      12-16
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  • @BTC_Sandy ya i would love to if I had the chance psychologically. missed out a large part earlier then thought I shouldn't fomo. we place large emphasis on psychology. had some advantage on mara and coinbase because we entered very very early
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  • koolgal
    ·12-15
    TOP
    🌟🌟🌟Thanks for sharing your investing journey @Mathematical Money .  Congratulations on your winning portfolio.🎉🎉🎉
    What is your advice looking ahead in 2025?  Do you think that Crypto stocks like $MARA Holdings(MARA)$ and $CleanSpark, Inc.(CLSK)$ will continue to rise ?  What about Bitcoin?

    @icycrystal @Shyon @ELI_59 @rL please join me to learn more about @Mathematical Money investing journey and his valuable tips on how to trade Options .😍😍😍

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    • icycrystal
      [Like] [ShakeHands]
      12-16 15:22
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    • koolgalReplying toShyon
      Have a wonderful week ahead 🌈🌈🌈💰💰💰
      12-16
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    • koolgalReplying toShyon
      My pleasure 😍😍😍
      12-16
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  • Jeff Chew
    ·12-15
    TOP
    @Mathematical Money Very impressive returns & glad to come across this interview article & just reposted it🙏I’ve been your follower/subscriber for months.Thanks for your sharing your investment philosophy😍 @koolgal @TigerClub @AyKing It's great to follow people with valuable insights & grow together🥰
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    • Mathematical Money
      thanks  @Jeff Chew . let's huat together !
      12-15
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    • AyKing
      @Jeff Chew 🙏🏽 thanks. Let’s learn from each other and grow together.
      12-15
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    • koolgal
      @Jeff Chew All the best 🍀🍀🍀🌈🌈🌈💰💰💰
      12-15
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  • @AyKing thanks. $5k is slightly small but still doable. would have to go with lower priced stocks for the options strategy. however, we do like to enter in 4 tranches usually (once a week over 4 weeks). so the exposure per week narrow to 1.25k. not much choices but still possible.
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    • AyKingReplying toMathematical Money
      👍thanks for sharing. I am also incline to 4 weeks.
      12-16
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    • Mathematical MoneyReplying toAyKing
      normally between 4-5 weeks where the decay is fastest. there's another school of thoughts that does 45-60 days as well. tried both but still prefer the 4 weeks decay in a bull run. probably will switch to 45-60 days when time is right
      12-16
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    • AyKing
      Thanks. :) Can I say your method is like a wheel strategy with short DTE on crypto?
      12-15
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  • thanks  @koolgal
    we think 2025 still looks bullish in general. can't predict when it will be winter again but btc's strength is still positive. Just have to be cautious and be ready to cut when the downturn comes, but let's ride it for now. :)
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    • koolgal
      I am also bullish on Crypto and Bitcoin.
      12-16
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    • koolgalReplying toMathematical Money
      Many thanks🥰🥰🥰
      12-16
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    • Mathematical MoneyReplying tokoolgal
      thanks. merry Christmas and happy new year to you and your family too. may you have a properties 2025 and many more prosperous years ahead!
      12-16
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  • BTC_Sandy
    ·12-14
    TOP

    Very impressive return! Just wondering if you would trade $MicroStrategy(MSTR)$ option which is much more volatile and has more premium? @Mathematical Money

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  • nomadic_m
    ·12-17 17:45
    TOP
    Congrats on your winnings. Your approach to options trading seems to emphasize simplicity and discipline. What advice would you give to newer traders who are looking to develop their own options trading strategies?
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    • Mathematical Money
      setup a plan. trade the plan through different cycles with small amount until you're confident. once confidence is there then increase appropriately reference to the different period of the market cycle
      12-17 22:56
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    • nomadic_m
      @derickt come & learn
      12-17 17:47
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  • Shyon
    ·12-16
    Thank you @Mathematical Money for sharing your strategy and experiences with us! Your insights into options trading, portfolio management, and the importance of proper position sizing are truly valuable. I appreciate how you focus on managing risk while seeking extraordinary returns, and your perspective on how to navigate both bull and bear markets is inspiring.

    May I have a few questions for you:

    1. You mentioned that managing emotions is one of the biggest challenges in trading. How do you deal with moments of uncertainty or when trades don't go as planned?

    2. In terms of portfolio management, what do you consider the most important aspect when choosing stocks, aside from liquidity & cash holdings?

    3. Since you’ve been active in trading crypto stocks recently, do you foresee any specific risks/opportunities in this sector going into 2025?

    Looking forward to your continued insights, and excited to follow your real-time trading updates!

    @TigerClub @TigerGPT @Tiger_comments

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    • Mathematical Money
      3. crypto is largely cyclical due to the nature of its halving cycle together with the fear and greed. as we enter the bull run proper, lots of us will miss out on insane gains, many will also end up being bag holders. my 2 cents worth: 2025 will be a pump hard and dump hard year.
      12-16 20:24
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    • Mathematical Money
      1. when in doubt, zoom out. short term fluctuations affect emotions quite abit. looking at longer term would probably help. other than that, look back to trading journal for the reason of investing in that stock, if the fundamentals or reason for buying has changed, then it's time to exit
      12-16 20:19
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    • icycrystalReplying toShyon
      [Like] [ShakeHands]
      12-16 15:40
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  • tigernaut
    ·12-15
    wow, glad to come across this article. totally agree that position sizing is important. i started out with both cash secured puts and then naked puts. would want to learn not to leverage too much and just go for a few predictable stocks for simple options trading that won't rock my emotions. @Tiger_SG @Mathematical Money
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  • Mathematical Money
    ·12-16 20:22
    2. industry that it is in would be important as well. example, you don't want to choose banks for past 4 years and be stuck with just 10-20% gains over 3-4 year horizon.
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  • @tigernaut it's human tendency to want to leverage or go with naked puts. we tend to be greedy when we do well. you can try to gather a few friends to do it together and check on each other for a start. or sometimes getting a mentor would help as well
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  • 1PC
    ·12-15
    Congratulations 🎉. Impressive Returns [USD]. I'm More on Stocks currently , would like to explore options in the future .. [lovely]... 🤔 maybe 2025 [smile]
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  • AyKing
    ·12-15
    Impressive run. Congrats. Any advice on how to start to grow with small capital like $5k?
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