The Challenge Portfolio

An aggressive portfolio to profit in any type of market

Jan 15, 2023

Antagonist premium members have access to two model portfolios:

The Blend Portfolio is designed for long-term investors.
The Challenge Portfolio is for those looking to generate short-term gains by trading options. It’s also designed to let you profit in any type of market.

You can read more about the Blend Portfolio here. The details of the Challenge Portfolio are below:

What is a model portfolio?

Model portfolios are designed to help people start investing for the first time or to help them invest in new areas, asset classes, and/or trading styles.

Rather than starting from scratch, investors can adopt or tweak a model portfolio based on their personal financial goals and risk tolerances.

Model portfolios are great for people who want to profit in the market but don’t have the time or desire to conduct their own research.

What’s so special about the Challenge Portfolio?

The Challenge Portfolio is more than a model portfolio. It’s a personal challenge for me (hence the name).

First, I fund it with my own money This means that when a trade wins or loses, it’s not hypothetical. It’s real money—my money—gained or lost.

Second, I manage the Challenge Portfolio live and share the process with premium members.

Transparency is one of the key values of The Antagonist. Therefore, I share every detail about the portfolio’s performance, both good and bad.

What is the investment style of the Challenge Portfolio?

This portfolio will be geared toward aggressive growth, but it will also hold hedging positions to reduce risk. It’s designed to achieve positive returns regardless of market conditions.

Given the aggressive style of the Challenge Portfolio, the risks are also higher than typical buy-and-hold strategies.

If you’re going to adopt this type of strategy, it’s best to start with a very small percentage of your overall investing portfolio. Doing so will reduce your risk while still giving you a chance to earn large profits. Consider starting with just 1%-2% of your overall portfolio.

What kinds of trades will you make with this portfolio?

I will trade stocks, ETFs, and basic options. A typical retail investor will be able to conduct similar trades with an online discount broker such as Schwab, tastyworks, Interactive Brokers, and other similar firms.

If you decide to place similar trades, you’ll need to add options trading privileges to your brokerage account. I explain how to do that in this article.

Does this mean that the Challenge Portfolio is suitable for all investors?

No!

No portfolio is suitable for all investors!

Everyone has different financial goals, timelines, and risk tolerances. There is no such thing as a one-size-fits-all portfolio.

Before you invest any of your own money, it is essential that you carefully conduct your own research and determine if a trade is right for you. That holds true whether you follow the Challenge Portfolio or any other model portfolio. Please read the disclaimer at the end of this post for more details.

To build a similar portfolio, how much money do I need?

I typically start with $3,000, but the minimum that I suggest is $2,500. That amount will keep your position sizes to a reasonable percentage (from a risk management perspective) of your trading account.

While it is possible to start with an account smaller than $2,500, it’s also riskier. That’s because your open positions will represent a larger portion of your portfolio. This means that if you lose several trades in a row, you could quickly wipe out your entire account.

How will you manage the Challenge Portfolio?

I will only trade using strategies that are easily accessible to retail investors. For example, I’ll open and close my positions online without the assistance of a broker.
I trade via Schwab’s thinkorswim platform and tastyworks. My trades are not unique to these firms, however. You should be able to make similar trades at any discount broker. Commissions, fees, account minimums, and requirements vary across brokers, so be sure to read their rules before you open an account.
I will begin with $3,000 split between two accounts: one at Schwab and the other at tastyworks. I like using two accounts because sometimes orders fill faster through one broker than another.
When I’m considering a trade, I’ll share the details via the chat feature in the Substack app. Be sure to turn on notifications so that you don’t miss an alert. After my order fills, I’ll send an email with all the closing details.
While much will depend on market conditions, I intend to place 1-3 trades per week. In the beginning, trade amounts will range from $50-$125. As my account grows, I’ll increase my position sizes.
Every Antagonist premium member will have access to a dashboard. You’ll be able to track the performance of each trade as well as the overall portfolio.

Are you open to ideas, questions, and/or feedback?

Yes! I love hearing from Antagonist members! You are always welcome to contact me by replying to these emails, reaching out via the member chat, or leaving comments at the end of each post.

What if the Challenge Portfolio isn’t for me?

If the Challenge Portfolio isn’t a good fit for you, I’m glad that you realize that now. You are wise to avoid model portfolios that don’t align with your goals, investment style, and/or risk tolerance.

Check out the Blend Portfolio to see if that is a better fit for you.

That’s all for now. If you have additional questions or suggestions, please free to contact me. I’m extremely excited for the Challenge Portfolio, and I’m equally thrilled to have you along for the ride.

If you know someone else who would be interested in the Challenge Portfolio or other Antagonist content, please invite them to join!

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Happy trading!
Jason Milton