Larry Rupp

What is "Deep Work?" How can it help your investing and your life? In this episode, we'll discuss the concept's roots and share tips to improve your daily routine.

Learn more about the Option Alpha Handbook, a free, non-subjective, digital encyclopedia for everything you want to know about trading.

Follow along step-by-step as we build a bot and update automations. Learn how to use the Backtester to identify a strategy and create a bot template with simple, specific decision criteria.

What is hedging? What is diversifying? Are they the same thing? This episode takes a closer look at the pros and cons of each concept, portfolio risk management, and what you really need to know about correlation.

Learn how to intelligently use SmartStops to optimize your trade exits with Option Alpha's proprietary technology that lets you set a profit target and trail the position with a stop loss.

On this episode, Pete Mulmat of the Small Exchange joins the podcast to discuss futures contracts. Learn why Pete is on a mission to make futures more accessible with small, standardized, and simple contracts.

Decision recipes are the building blocks of automations. On this episode, we highlight eight popular decision recipes used in the autotrading platform.

In this interview, Jason Goepfert discusses investor psychology, managing risk exposure, and whether market sentiment analysis actually works.

On this episode, we do a deep dive into the volatility of bid-ask spreads with four case studies, and discuss how you can use automation to address pricing anomalies.

On this episode, we talk about the future of automated trading, if automated trading provides an edge, and the possible downsides of automated trading that you should carefully consider.

On this week's show, we'll do a mini "State of the Union" on what we've been up to, what's new, and what you can expect moving forward.

This podcast walks through the two macro trend bots we built to demonstrate how you can start leveraging the new automation tools at Option Alpha to trade either stocks or options in a trend.

This show is dedicated to helping you understand all the different ways you can hedge a short naked put.

It’s well documented that investors not only chase performance, ultimately yielding sub-par performance in pursuit, but they also do not have enough patience to stick with strategies long enough. My hope is that it ends today. You should objectively look at strategies for what their expected outcome range is, not what it’s done recently.

In today’s show I welcome back Cameron Skinner to learn more about his strategy when trading options.

In this episode I walk through just one type of strategy that I think is the tip of the iceberg for situational trading and hedging bots. This example automates hedging using the VIX.

In this show, we will go through 18 questions to help you prepare for the inevitable moment of options exercise and assignment.

This podcast is geared specifically at exposing 13 classic and detrimental investor biases that ruin performance. Any of these sound familiar?

I’m going to help you break down the zillion ways you can save money to invest in core concepts that I have used my own life to save money at an incredible pace.

In this episode we answer some common questions about the new autotrading platform. We’re also going to go through some of the features you will love about it.

When it comes to trading, tax concepts and terminology can get complicated fast. Our goal in this episode is to help educate and explain trading taxes for all traders so that it’s useful to you moving forward.

We answer 15 of the most popular options expiration questions to help you understand and effectively navigate options expiration.

This is a vacation checklist for options traders to use before going off the grid so you don’t have any surprises when you turn your computer back on after a few days of market activity.

This show is dedicated to executing and filling options trades.

This episode is a case study of a recent FXI position in which we were assigned stock. I'll walk through the entire position from start to finish, including all the profit and loss calculations with adjustments and early assignment.

We explore investor sentiment from all angles and help discover which readings, if any, give predictive power to future stock market returns or trends.

This trading psychology podcast was curated to help you learn how to more effectively recognize and manage the dozens of emotional and cognitive responses you’ll encounter in your trading career.

This podcast episode helps to explain why diversification fails when multiple securities autocorrelate during market drawdowns.

This podcast episode features the best covered call management techniques for stock and options traders.

We’re diving deep into “LEAPS” options contract in this podcast episode with a comprehensive guide for traders to help you make the best decisions for your portfolio.

This podcast episode takes an in-depth look at box spread basics, their advantages and disadvantages, and how they can be used by options traders.

This is a trader's guide to index options, how they work, how they are different, and what you need to be aware of if you decide to start trading them in your portfolio.

After some in-depth research, these are the findings of the protective put strategy and its effectiveness at protecting or hedging stock positions.

In this episode, we discuss the impact of volatility on options pricing.

In this podcast, I walk through the research on earnings moves and how different options strategies performed under various setups and conditions.

We’re excited and honored to have a very special guest on the podcast, Richard Hudson. We discuss the misbehavior of markets and why financial models are flawed.

This episode is a recording of the newest book Option Alpha released entitled “Mastering Covered Calls.” I encourage you to pick up your copy now (did we mention it’s 100% free) and follow along as you listen to this audiobook.

On this episode we go over the top three performance insights we learned from our massive study on covered call performance.

In this episode I want to cover the 5 critical factors that your trading strategy should have. To us, these serve as the foundational elements for choosing which investing vehicles, indicators, or systems most appropriately fit your portfolio.

Check out our interview with former market maker and CBOE instructor Kevin Davitt. You're going to love this candid and wide-ranging discussion as much as we enjoyed the time with Kevin.

This is a list of the 27 biggest fears and questions traders in our community have about options trading.

These are the 3 potential market setups that lead us to break our profit-taking rules, based on the Profit Matrix research about holding positions longer towards expiration.

In this podcast episode, we'll discuss the put-call ratio and investigate if it is a useful market indicator.

In the world of investing, and specifically trading options, you need to live by certain rules that keep you safe and protected from the unknowns of the market. These are the 11 golden rules to follow.

Since we are option sellers and our edge comes from selling overpriced options when IV is high, it's natural to assume that buying options during low IV markets is a way to make money. This podcast explains why that is not always true.

This episode provides an in-depth look at a short put options trade that resulted in assignment of long shares of stock. With patience, mechanical adjustments, and proper position sizing we were able to manage this position over many months.

In this podcast episode, we interview Kevin Smith and Tavi Costa from Crescat Capital, a top performing macro hedge fund.

This is an updated look at the progress of the new autotrading platform at the time of recording. Will and Rob from the Option Alpha team join Kirk for an in-depth discussion about the new platform.

Learn how to build an options portfolio with $3,000.

The truth is that you are going to have losing trades, a lot of them, over the course of your career. The first step on your road to elevating yourself is to ask yourself, "Can I trust the process?"

In this podcast I talk about why it's important we know the story of the three little pigs that traded options. I'll walk through each of the different portfolios the three little pigs used and how volatility and variance can impact long-term performance.

In this podcast I walk through the four general market situations I avoid trading aggressively.

Before you place your next options trade you need to ask yourself these 7 questions first.

This podcast is dedicated to the 17 most popular questions we are asked by Option Alpha members.

If you trade iron butterflies today's case study is for you. We walk through our assignment and covered call adjustment that ultimately netted a profit.

In this show we'll focus on our most recent case study in EWZ, a trade in which we turned a losing set of straddles into a $540 winner with a little patience and some mechanical adjusting.

Learn how to manage your money and generate wealth with this 3 step process..

Were you recently assigned an options contract in your account? Here's a case study on how to manage the new stock shares moving forward.

This episode focuses on what I'm calling the 5x2 trading psychology matrix. This "victim matrix" has 2 paths you can follow every trading event, and each path has 5 stages or steps.

On this show, I have the opportunity to interview former CBOE options market maker and volatility trader David Lincoln. This is an episode you won’t want to miss!

Do you trade options? Struggling to be profitable? See if you are making these 11 common options strategy mistakes.

In this episode, we use backtesting results take a deeper look at whether it is more profitable to sell options 60 days out or 30 days out from expiration.

On this podcast we interview a very special guest, Larry Connors, and discuss his new book, "Buy the Fear, Sell the Greed."

Choosing which ticker symbols and options strategies to use when entering new options trades can sometimes seem overwhelming. This podcast breaks down the key factors when entering new option trades and building out your portfolio.

In this podcast, I want to walk through a recent trade in which we were assigned on a short put and help you understand how being assigned options impacts your account and how you can still trade around these events using a couple key strategies.

In this podcast episode I want to slowly walk through the concept of contango and backwardation. I will offer a couple of different examples showing how it works in real life and how we might be able to use this awareness of futures pricing part of an options strategy in our portfolio.

Ever feel like some of the options trades you make blow up in your face? Here's why it happens and what you can do about it.

When it comes to options trading, there are a lot of things you can control, and a few you cannot. This episode provides tips on how to manage the risks you can control and avoid "blowing up" your trading account.

In this episode, we dive into the three main areas of the expected probability paradox to help you understand why option selling still outperforms the market, even if you can't find perfect pricing.

This podcast is a deep dive into options skew and the volatility smile for both inter-month and intra-month option contracts.

Today's podcast is essential to help you understand how to calculate break-even prices the correct way on iron condors, iron butterflies, and other risk-defined strategies.

The goal of this podcast episode is to help you completely understand how implied volatility works, why we need it, where it comes from, and how we can profit from it as option sellers.

In this podcast episode, you'll learn how to overcome the fear of being "wrong," learn from your trading mistakes, and transition into new habits.

On this episode, we use our backtesting software to analyze the results of a weekly bull call spread in DIA, the Dow Jones Industrial Average ETF, and its performance compared to a monthly bull call spread in DIA.

Some traders wrongly assume that if they can't trade unlimited risk option strategies, such as straddles and strangles, that they should just avoid trading options altogether. Here are four alternatives to convert unlimited risk option strategies into risk-defined positions.

This show focuses exclusively on rolling options forward by showing you two different case studies in TLT and IWM. Both trades took multiple months to turn a profit and multiple rolls of our contracts.

Here are 5 easy tips for smooth option order execution if you're having trouble getting trades filled in the market.

Here is a look at four situations you need to be aware of when building out your portfolio. These early warning signals of a non-diversified options portfolio can help you adapt more quickly to an ever-changing market by making smarter trades and adjustments.

This podcast offers some insight and examples of why higher trading frequency and averaging down (or up) around the market creates an environment in which market direction becomes more irrelevant the longer you trade.

When trading options, what contract month and option strike price should you buy or sell? We have the data from thousands of backtested trades to help you find the answer.

In this podcast episode, we'll break down some of the best resources and tips on managing your options portfolio with limited time.

Want to learn how to trade options the right way? Follow our 90-day framework for mastering the options market.

In this episode we explain why selling cheap options with high win rate probabilities may not be the best idea for your portfolio.

My goal with this podcast is to help you cross the proverbial "trading bridge." Learn to stop focusing on ROI and confidently analyze options strategies before putting money at risk.

These 7 things should be a priority for all options traders. Get them right and you set yourself up for success. Get it wrong and you could go down in flames.

As you start managing larger trading accounts and portfolio sizes, you'll need to make a couple small but important changes to optimize your strategy.

This podcast focuses on the reasons why I believe some traders are always more profitable than others and looks at the six key areas that differentiate successful and unsuccessful traders.

Don't use real money to practice trading options. In this show, I want to get back to basics and re-visit some important concepts or frameworks you can use when trading that will help you navigate the next move down.

In this podcast, I want to take some time to share the top-five options trading psychology lessons I've learned over the last 18 months.

This podcast dives deeper into the lead greek and covers both a basic understanding of what delta is and how it works, plus some more high level insights into how I used delta to enter a trade in XLE.

This podcast episode focuses on the advantages and disadvantages of using a short straddle or short iron butterfly, and when you should use one instead of the other.

In today's podcast, I'll walk through the different market environments and setups that might work best for debit spreads and credit spreads.

On this podcast episode I want to help you avoid five of the big mistakes you can make when executing an options order.

In this podcast I walk through the process of managing inverted option positions and help you understand what numbers to track when making adjustments.

In this podcast episode, I'll preview some of the new research we've done on long straddle option strategies during earnings.

What is a day trader? Does trading every day make you a day trader, and what are the advantages and disadvantages of trading every day? We answer these questions and more in this podcast episode.

On today's show, I'll talk through what our research shows about exiting trades early, when to leave options on to expire worthless, and how it impacts your bottom line.

In this episode I want to help you become a better options trader by not watching the market and focusing on more systematic trading setups, as well as provide the single most important case study in market prediction in the last two decades.

In this podcast I want to conceptually walk through how you can convert unlimited risk strategies into their risk-defined counterparts and limit your exposure.

If you trade options, you'll undoubtedly run into a scenario where you get challenged by a stock moving against your position. When this happens the first question many people ask is, "Do I start rolling up strike prices and adjust the position or close out the trade for a loss?"