Option Strategies Insider Review 2023

Jeremy Biberdorf
By: Jeremy Biberdorf
Nov 18, 2021
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Option Strategies


4.8 rating based on 5 ratings


In a nutshell:Option Strategies Insider provides options trade alerts and educational materials for new and experienced options traders.

With both free and paid subscriptions, Option Strategies Insider is a solid introduction to options trading. While new traders can learn all the basics of options trading, more experienced traders can understand and utilize advanced trading techniques.

In addition to providing educational material, Options Strategies Insider supplies market research, watchlists, and trading plugins.

FeesService TypePromotion
$0 - $167/monthOptions trade alerts$7 trial membership

Option Strategies Insider makes it easy to start trading options with both free and paid memberships. It also offers a $7 trial which allows you to try its highest membership tier.

Pros & Cons
  • Track record of success
  • Extensive educational content
  • Numerous discounts available
  • $7 trial membership
  • Only active and new trade positions are available

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Full Options Strategy Insider Review

Would you like to try your hand at options trading but don’t know where to start? Option Strategies Insider can help with both free and paid resources and services. The goal of Option Strategies Insider is both to help people learn about options trading strategies and to make better trades. It offers three membership tiers, including a free membership.

Options Strategy Insider is best for:

  • Options traders
  • Those who want to learn about options on a budget
  • Traders who lack the time to perform their own market research

External Options Strategies Insider Review & Ratings


What is Options Trading?

Options trading involves buying contracts. An options contract gives you the right, but not the obligation, to buy or sell an underlying asset on a specified date.

There are two types of options: call and put. A call option contract then allows the holder to buy a stock and a put option gives the holder the right to sell a stock. With a put option contract, you can sell shares at a higher price if the price drops.

It is not too difficult to see how trading options could be lucrative. For example, if you buy a call option which is the option to buy a security and the price increases, you can buy it at the agreed-upon price and sell for a profit.

What Is Option Strategies Insider?

Product Name
  • Option Strategies Insider
  • Options trading alerts.
Membership Fee
  • $0-$167/month (discounts available).
Education & Support
  • Video courses, eBooks, webinars, and forums.

Option Strategies Insider was founded by CEO Chris Douthit. The company has a high success rate with 87% winning trades since 2015.

Prior to founding Option Strategy Insider, Chris was a professional trader for several well-known companies in the finance industry . Those include TFM, Spear, Leads & Kellogg and Goldman Sachs.

In 2014, Chris was consulting for a man named Jim. Back then, Jim was convinced to sign up for an options trade alert system that was a total bust. Basically, there was zero transparency as far as how its trades worked and there was no exit strategy.

Jim was losing big even though the site claimed 100%+ returns. It turned out that the site was run by people with no real experience in finance who had no idea what they were doing.

It was this predatory scenario that inspired Chris to start Option Strategies Insider . He wanted to both educate people about options trading and also provide them with trade alerts based on real expertise.

And that’s exactly what he did. Chris has over 20 years of experience working as a professional trader, so he has a solid foundation in place for a winning options trade alert service.

If you are looking to learn more about options trading and perhaps even give it a try, this program is worth a look. Even if you decide not to subscribe, there is quite a bit offered for free.

Plus, there are some nice discounts regularly offered, including an exclusive discount for Modest Money. We’ll get to all of that in more in the Option Strategies Insider review below.

But does Option Strategy Insider really deliver? Let’s find out.

Try Option Strategies Insider for only $7

Option Strategy Insider Features

Option Strategies Insider is more than just a simple trade alert service. Instead, it has several features that make it well worth a look. Many features—such as the thinkorswim Training Center & the Options Dictionary—are even available with a free membership! This setup is ideal for the beginning traders who want to educate themselves before making any investments.

However, more advanced features like “Executive Research” will require a paid subscription. Fortunately, there are deals and discounts available that make the platform seem even more appealing (we’ll explain this in further detail later on).


Currently, Option Strategies Insider has six eBooks that you can download. These are even available with a free membership. All you need to do is create an account on the website, and then you can download the PDF for each book. Here are the eBooks currently available for download:

  • The Elements: The Key to a Balanced Stock Portfolio (22 pages)
  • Value Investing: How to Find Undervalued Stocks (13 pages)
  • Cash Flow Positive: Smarter Dividend Investing (23 pages)
  • Covered Call Cash: Leveraging Stocks for Income (40 pages)
  • Time is Money: Conquering the Iron Condor (43 pages)
  • The Risk Reversal: The Ultimate Options Strategy (61 pages)


As a member, you gain access to a variety of educational materials, and some are even available with a free membership. Educational resources include:

  • Options trading video courses
  • Thinkorswim lessons
  • Investing books
  • Webinars
  • Option dictionary
  • Trading examples
  • A “Partner Eligibility” section
  • FAQ index
  • Blog posts

The really nice thing is that all of these resources are included with a free membership. The one exception is the advanced options course. Still, a free membership includes the beginner and intermediate courses, which is great.

As mentioned, you gain access to both Beginning Options and Intermediate Options with a free membership. Because you have access to so much educational material for free, you can learn all about options trading without spending a dime.

Then, if you decide you want to get into advanced strategies and actually start receiving alerts, you can go ahead and sign up.

Beginning Options

This options trading education course covers the ins and outs of options trading. It establishes the “why” and how to read options. Then, it covers how options pricing works, combining factors, and option and position Greeks.

As you can see, this course lays the groundwork for options trading. It doesn’t so much go into the nitty-gritty but serves more as an introduction to the basics of options. Later, you will learn more about how trading actually works.

It will take approximately 90 minutes for you to watch all the beginner lessons. You can post questions in the comments below each video, which will generally be answered by Chris himself. Every video in this section is available to both free & premium members. Currently, there are eight beginning options courses, as listed below.

  • Beginning Options
  • Why Options
  • How to Read Options
  • Option Pricing (Part 1)
  • Option Pricing (Part 2)
  • Combining Factors
  • Option Greeks
  • Position Greeks

Intermediate Options Courses

Intermediate Options is all about buying and selling. If you are trading options to turn a profit, this is what you will spend most of your time doing. Thus, it’s important to understand the ins and outs of how buying and selling work. This is especially crucial when it comes to executing specific strategies (like iron condors or multi-leg options trading).

Chris walks you through buying and selling on thinkorswim, which is TD Ameritrade’s platform. Many traders prefer thinkorswim because it can work well for both intermediate and advanced traders.

Like the beginner course, the Intermediate Options Courses are available to both free and paid members. This section includes around 50 minutes of video instructions (with examples) and includes:

  • Buying Options (Part 1, 2, and 3)
  • Selling Options (Part 1, 2, and 3)

Advanced Options Trading Course

The last course, Advanced Options Strategies is, of course, the most advanced of the three. It’s also the only course not included with a free membership. It also has 11 different modules, making it the meatiest of the three.

As you might expect, Chris devotes the entire time in these videos to advanced trading strategies and how they actually work. You’ve already learned the basics; now it’s time to become a real pro with advanced options strategies. You can expect to spend about 75 minutes watching all of the videos in this section.

You’ll learn the following 11 advanced options strategies throughout this course:

  • Multi-Leg Option Intro
  • Buy-Write Trading
  • Long Vertical Spread
  • Short Vertical Spread
  • Iron Condor
  • Butterfly Spread
  • Calendar Spread
  • The Straddle
  • The Strangle
  • Contracts to Trade
  • Adjusting a Trade

Trading Tools

This service includes a few trading tools to help make things easier for you. The main sets of tools you will have are:

  • Thinkorswim plugins
  • Short put calculator
  • Stock price alert

To get the full experience, I added the thinkorswim plugins on my computer. You can see the results below:

IV Rank (Watchlist)

Option Strategies Insider IV Rank Levels

This plugin adds an implied volatility (IV) column to your watchlist to show where the security’s IV lies compared to its yearly high and low IV.

IV Rank (Chart)

Option Strategies Inside IV Rank (Chart)

This plugin provides the same information as the watchlist plugin, but it allows you to view the data on the chart. Thus, you get a more visual way to see the data.

Short Put Calculator

Option Strategies Insider Short Put Calculator

The short put calculator helps you calculate the percent discount you can receive on a stock or ETF compared to where it trades today. Once you fill in the required information, it will show you whether the security finishes above or below the strike price.

Stock Price Alert Tool

Option Strategies Insider Stock Price Alert Tool

The Stock Price Alert Tool is a relatively simple tool you can use to receive alerts when a stock you are monitoring rises above or falls below your specified price.

Trade Alerts

Trade alerts are what we’re all here for, just as they are for The Motley Fool’s stock picks . It’s nice that they include so much educational material to help you understand how options trading work, of course.

But if you aren’t a full-time stock trader, you likely won’t have time to research every single trade. That’s where Option Strategies Insider’s trade alerts come in, helping streamline your options trading experience.

They don’t inundate you with a crazy number of trade recommendations; the frequency varies as different opportunities arise. However, you can expect somewhere around one trade alert per week, on average.

Chris provides guidance for both when to buy and when to sell. As Chris points out, there are some services that tell you when to buy, but not when to sell.

“Don’t be fooled by other option investing sites that post huge return numbers,” he says. “What these sites all do is tell you when to buy the option and then totally leave it up to you to pick when to sell. What kind of service is that?” Here are some of the performance stats from its recommendations the past two years:

Options Strategies Insider Trade Performance

As you can see, performance was down slightly in 2020, but overall, the numbers look quite good. More than 75% of their trades have been winners with over 40% return on capital, on average.

Note that these alerts are different from the Stock Price Alert tool; those are alerts you set up for yourself. On the other hand, these trade alerts are the ones Chris and his team send to members.

You can either receive OI’s trade alerts via email or via Twitter, if you prefer. Trade alerts are automatically sent to the email tied to your OI account. If you also want to see them on Twitter, the team posts alerts on its Twitter page.

Note: they don’t share their trades on Twitter; you must be a paying subscriber. On Twitter, they simply alert you that there are no recommendations when they are released and instruct you to log in to view them.

Pricing & What’s Included

Option Strategies Insider has three membership tiers, and each one has a generous number of benefits. Even the free tier includes quite a bit.

As with most tiered pricing structures, each tier includes everything the previous tier does while adding additional benefits.

Monthly Membership Packages

You can see the monthly cost of each membership tier above, but note that those are only the monthly payments. If you sign up for the Executive Membership or the Ultra Membership and pay annually, you’ll get two months free.

Then, only for Modest Money readers, you can get an additional 20% off your membership forever . That is a very exciting deal!

Most of the features for each tier are fairly self-explanatory, but some are less obvious.

Free membership is best for complete beginners. It’s extremely easy to sign up for, requiring only an email address (which will need to be verified).

Although this membership level doesn’t provide any trading tools or perks, it has plenty of educational material available for free. Some people learn best through reading; others learn best when using visual examples. The free Option Strategies Insider educational library provides both types of materials, making it easy for anyone to start learning.

In addition to providing sequential video lessons, OI follows up each lesson with a quiz. This provides an opportunity for traders to see how much they’ve learned (and what they might want to review).

Executive membership is best for those who are ready to start—or already are—trading. Of course, this includes people who’ve completed the free learning materials. However, it also consists of those who are already actively trading but would like to brush up on their skills.

The executive membership can even be utilized by those who are confident in their trading abilities but lack time to conduct market research. Subscribers receive trade ideas via the Executive Portfolio recommendations.

These recommendations include not only the stock suggestions themselves but also the data behind the selections. Subscribers can expect to receive between three to six suggestions depending on the month. Historically, these suggestions have performed quite well, achieving a 90% success rate over the last three years.

Ultra membership is best for traders who would like to increase their trade frequency. In addition to the Executive recommendations, subscribers also receive 1-2 “Ultra” monthly recommendations. This membership includes all of the perks from the prior two plans but adds high-risk trading into the mix.

Ultra trade suggestions are based on trading data, market trends, company balance sheets, market settlements, relevant politics, and other factors.

Some stock suggestions are long-term investments, although Ultra membership also provides short-term suggestions. Either way, it’s critical to remember that these investments are more likely to fall through than Executive Portfolio recommendations.

That said, high-risk means high reward. While the majority of portfolio suggestions won’t yield much success, those that do will skyrocket in value. It’s not uncommon for the average return to exceed 300% on winning trades.

With the Ultra membership, you get:

Ultra trade alerts: These are trade alerts on top of what you get with the executive membership. In other words, you’ll get an extra one or two alerts per month to maximize your returns.

Lifetime optional membership: OI doesn’t always advertise the lifetime access rates, but they do give you the option to pay once for a lifetime membership. This can be a great deal, especially if you have confidence in the service. However, it’s important to consider how long you anticipate using the service. If you’re only planning on using it for a short while, then it may make more sense to continue with a monthly or annual plan instead.

Is Option Strategies Insider Right For You?

Option Strategies Insider is a “strong buy” for anyone who’s looking to trade options. They have almost 90% winning trades since 2015, and their annual return on capital is usually around 50%.

That is definitely solid performance and makes it worth a look. Plus, they give members access to a large amount of educational material free of charge.

In other words, if you aren’t sure about trading options yet, you can sign up for a free membership just to learn the ropes. Better yet, you can try the Ultra Membership for $7 for 7 days (normally $167/month) and explore everything the service has to offer.

Because of the wide range of options OI offers, this service is right for just about anyone who’s interested in trading options.

Frequently Asked Questions

It’s a service that educates new and expert traders on Options trading. It provides video courses, eBooks, webinars, and forums for its users. The main feature of Option Strategies Insider is the trade alert services.

The founder and current CEO of Option Strategies Insider is Chris Douthit.

Chris Douthit is the founder of Option Strategy Insider. He founded the company in 2015. Before then, he was a professional trader for TFM, Spear, Leads & Kellogg, and Goldman Sachs.

He holds an M.BA and other financial degrees, making him an expert in his field. With more than 20 years of working experience, he has a reputation in this field. So, you can rest assured of winning option trade alerts.

Option Strategies Insider has three membership options; free, executive, and ultra membership. The executive and ultra membership packages cost $97 and $167, respectively, with a $7 free trial for seven days. You also gain two months of free annual payments and a $20 discount for lifetime memberships.

With a free membership, you can access tutorial courses, books, webinar training, and more for no cost.

Executive membership offers you extra features alongside the free membership. These services include; advanced option courses, executive trade alerts, thinkorswim plugins, and more.

The Ultra plan offers ultra trade alerts and optional lifetime memberships that come with great deals.

If you’re a new option trader that wants to learn the basics of the trade, you can try Option Strategies Insider. Its introductory level courses are a good fit for any beginner in options trading.

Even if you’re an expert, the advanced courses and the trade alerts are things you’ll gain from.

It is also fit for you if you don’t like the stress of researching trades. Option Strategies Insider will do the work for you and give you the best winning trades around.

Chris Douthit offers the best option courses and trading picks you can find. Option Strategies Insider has almost 90% winning trades since 2015, so you’re in safe hands.

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