Show notes: http://optionalpha.com/show197

There's a lot of research to support the usage of trend indicators as simple risk reduction elements that can be layered onto an existing strategy. The trouble, however, was that in the past investors had to monitor the trend and execute the appropriate trade reversals when the trend changed. With automation, we can now offload this simple portfolio strategy to bots - and cleverly defined multiple possible trend exits all from one simple automation. This week's podcast walks through the two Macro Trend bots we built to show you how you can start leveraging the new automation tools at Option Alpha to trade either stocks or options in a trend.

Show notes: http://optionalpha.com/show196

Trading short naked puts (i.e. put selling or put writing) can be an effective and profitable options trading strategy. Often the attraction to naked put selling is the ability to collect premium with a margin for error if the stock drops, and have the ability to purchase stock at a discount to the current market price. The trouble comes however when the stock moves lower and challenges the naked put position and today's show is dedicated to helping you understand all the ways you can hedge short naked puts.

Show notes: http://optionalpha.com/show195

It's well documented that not only do investors classically chase performance, ultimately yielding sub-par performance in pursuit but that they also do not have enough patience to stick with strategies long enough. My hope is that it ends today and you can elevate yourself above all this and objectively look at strategies for what their expected outcome range is, not what it's done in the last couple of months or a handful of trades.

Show notes: http://optionalpha.com/show194

This week I'm thrilled to welcome back on a very popular guest, Cameron Skinner, to the Option Alpha podcast. Way back on Show 61, Cameron and I talked at length about his consistent and religious process for trading options even though his "day job" as a real estate investor takes the majority of this focus and attention. Well, Cameron is back for another interview, and this time we dove even deeper into his strategies and how he thinks about risk and the markets. Please enjoy our follow up conversation with Cameron Skinner.

Show notes: http://optionalpha.com/show193

One of the beautiful things about shifting to fully automated trading on the new Option Alpha platform is the ability to finally be able to clone and replicate entire trading strategies using bot templates. Bot templates allow anyone to build a trading strategy and seamlessly share the structure and details of that strategy with one-click. Today, I want to walk through just one type of strategy that I think is the tip of the iceberg when it comes to situational trading and hedging bots. I have no doubt that this discussion will spark some creative ideas, allow you to dream of what's possible, and show you that the future of trading is incredibly bright once you adopt autotrading.

Show notes: http://optionalpha.com/show192

Back on Show 187 we tackled the top 15 questions we consistently get around options expiration. Today, we're taking a slightly different approach and addressing head-on the 18 biggest questions and concerns traders have around options assignment and exercising, whether on or before expiration itself. Regardless of your trading experience level, seasoned investor, or complete options newbie, I promise you that today's episode will help you more clearly understand and navigate any future options assignment or option exercise situation you might find yourself in. After all, this is part of the business and if you trade long enough you'll have to manage through this, dozens of times.

Show notes: http://optionalpha.com/show191

We're all subject to investment biases, often multiple biases working together at the same time trying subconsciously to derail us. And whether we offload the actual order execution and management to an autotrading platform or not, the human element or side of investing still impacts the decisions we make and the strategies we choose to execute or not. Until we take the time to label and recognize these major investor biases, we cannot overcome or manage them in the future. Therefore, today's podcast is geared specifically at exposing these classic and detrimental investor biases that ruin your performance. You're either going to learn how to manage and deal with them or be unknowingly controlled by them for the rest of your life.

Show notes: http://optionalpha.com/show190

One of the most impactful things you can do for your portfolio is add money or capital to it. A consistent and persistent schedule of funding your account, even with small amounts, gives you the added boost that compounds over time. But we all know this already don't we? So why don't we do it, or at least at a higher level than we do now? On today's show, I'm going to help you break down the zillion ways you can save money to invest into core concepts that I have used in my own life to save money at an incredible pace. I'm a firm believer that these "big ideas" around saving money will help free up some cash for you.

NEW Beta Site is Live: https://beta.optionalpha.com

Today?s show is a massive announcement ? we are officially announcing that we have our launch dates set for our new auto-trading platform. Today on the show, we?re going to answer some common questions that we've been getting around the new platform and we're also going to start going through some of the features that you are going to love about it.

We have all the information you need right now about the platform and how to use its new features on https://beta.optionalpha.com.

Show notes: http://optionalpha.com/show188

Ah, taxes, a dreaded but necessary part of investing and trading. And although you might be inclined to skip this week's show, I'd encourage you to dive in because, even for me personally, this discussion helped clarify and re-solidify concepts that were mildly opaque. After all, tax concepts and terminology can get complicated fast and our goal is to help educate and explain things so that it's useful to you moving forward. Plus, I brought in a special guest to help chat through the different sections and I know you're going to love this week's episode on taxes for options trading.

Show notes: http://optionalpha.com/show187

We get a lot of questions around options expiration - hundreds and hundreds each week. Yet, the same vital few seem to float to the top consistently so we're pulling these 15 questions into this week's podcast episode to help you understand and effectively navigate options expiration. And in the off chance, we didn't answer your question during the show, you can always reach out to us anytime for help and support. If you're going to trade options, you can't avoid going through expiration. So, if you're going to trade options, you can't miss this week's podcast.

Show notes: http://optionalpha.com/show186

Summer vacations are in full swing and as everyone rushes to their favorite social distancing hot spot, traders are often left wondering what to do with their positions and trades while away. And since we cannot build automated and trigger-based strategies yet, though it's coming soon from Option Alpha, we wanted to help with a simple but effective checklist you can use to square up your account before going off the grid. Make no mistake though, this checklist isn't just for when you go on vacation, it's also a great workflow to help you before a long business trip or busy week at home when you have limited time to manage your account.

Show notes: http://optionalpha.com/show185

Filling option trades can often feel like pulling teeth. While some trades and orders get through easily and without issue, others are incredibly stubborn and hard to get filled. To add to your frustration, the entire order execution process appears to be just another confusing black box. There's seemingly no rhyme or reason why this trade got filled but that one didn't? So this week's show is dedicated to shining a light on order filling for option trades and helping to demystify what is otherwise a simple market process.

Show notes: http://optionalpha.com/show184

Adjusting trades that move against you can be hard enough. Choosing how to adjust and when to pull the trigger complicates what otherwise was a simple trade to start with. Now, throw in an early assignment to the mix and you've got quite the convoluted option trade on your hands. Sounds daunting already doesn't it? But fear not. Complicated and complex trades like the one that happened to us in FXI the other month give you a great opportunity to learn and grow as a trader. On today's show, we'll walk through the entire FXI position from start to finish, including all the profit and loss calculations including adjustments and an early assignment. Lean into this show and don't skip it - your future self with thank you for taking the time now so that you don't have to freak out later when it happens to you.

Show notes: http://optionalpha.com/show183

Be fearful when others are greedy, and greedy when others are fearful. This classic Buffett quote had echoed though the ranks of investors for decades. But does that data support the methodology? Does investor sentiment, which for many investors is widely considered a contrarian indicator, have enough predictive power to warrant our time and attention? In today's show, we'll explore investor sentiment from all angles and help discover which readings, if any, give predictive power to future stock market returns or trends.

Show notes: http://optionalpha.com/show182

Greed, fear, FOMO, anxiety, panic, over-confident, stubbornness, impatience. These are just a few of the frequent emotional and mental states that traders find themselves in. And while we cannot avoid these emotions and thought processes, we can learn to manage them through emotional intelligence. This week's podcast was curated to help you learn how to more effectively recognize and manage the dozens of emotional and cognitive responses you'll come across in your trading career.

Show notes: http://optionalpha.com/show181

There's an old saying in investing that a "rising tide lifts all boats." And while that might be true, when the tide goes out, all the boats sink and fall just as fast as they rose together. Still, you'll hear the pounding of drums in the name of classic diversification as the portfolio savior during these downturns. Our research suggests, however, that even a well-diversified portfolio can still completely blow up just when you need it to protect you most.

Show notes: http://optionalpha.com/show180

You've got your prized covered call setup and it's working in your account - now what? How do you manage or adjust the position in different market scenarios? Lucky for you, we are going to review the best-covered call management techniques on today's podcast. And if you think this show is just for stock traders, you'd be wrong, because proper covered call management could be a lifesaver for options traders who get assigned and are forced to deal with stock.

Show notes: http://optionalpha.com/show179

You've got your prized covered call setup and it's working in your account - now what? How do you manage or adjust the position in different market scenarios? Lucky for you, we are going to review the best-covered call management techniques on today's podcast. And if you think this show is just for stock traders, you'd be wrong, because proper covered call management could be a lifesaver for options traders who get assigned and are forced to deal with stock.

Show notes: http://optionalpha.com/show178

Box spreads and arbitrage strategies are often synonymous with one another and referenced interchangeably in the options trading community. And after all, who doesn't want a risk-free way to earn money right? But like all things that seem too good to be true, box spreads carry some serious risks if you're not careful in how you set them up. Today's show then focuses exclusively on box spread basics for options traders.

Show notes: http://optionalpha.com/show177

Index options have continued to grow in popularity. Potentially because they are easy to use, available in highly liquid markets, have favorable tax treatment in some cases, and offer a simple settlement process. Therefore, we've dedicated an entire show to help you understand what index options are, how they work, how they are different from equity options, and what you need to be aware of if you decide to start trading them in your portfolio.

Show Notes: http://optionalpha.com/show176

Hedging stock positions can be tricky business. One of the most common schools of thought is to use a simple protective put strategy whereby a stock investor would simply purchase a long out-of-the-money put option to act as "insurance" in case the stock fell. Sounds logical but we're skeptics here at Option Alpha and so we went on a hunt to see what research and data say about the protective put strategy and it's effectiveness at protecting or hedging stock positions.

Show Notes: http://optionalpha.com/show175

Stock trading is easy to understand conceptually because it's one-dimensional. Either the stock goes up or it goes down. Clear and simple, at least from a trading and profit or loss perspective. Options trading, however, is multi-dimensional. Price, time, and volatility all impact the value and price of an options contract. On today's show we're selectively choosing to highlight the impact that volatility has on options because, as we've seen in the 2020 market collapse, if you're not managing volatility, it could become your worst nightmare.

Show notes: http://optionalpha.com/show174

Earnings season comes around four times a year for stocks, and as traders, we've always loved the idea of trading these events for the crush in implied volatility and quick potential moves in option strategy positions. However, after analyzing 1,546 earnings events across 40 underlyings over 10 years we decided to stop trading earnings events completely. In today's podcast, I'm going to walk through the research on earnings moves, and how different options strategies performed under various setups and conditions.

Show notes: http://optionalpha.com/show173

We're excited and honored to have a very special guest this week on the podcast, Richard Hudson, co-founder of the London and Brussels-based Science Business Publishing Ltd. He's the co-author of The (mis)Behavior of Markets: A fractal view of risk, ruin & reward which he wrote with famed Yale/IBM mathematician Mandelbrot. Our discussion frankly should be required listening for any investor and was recorded in January of 2020 immediately preceding the market crash that occurred just weeks later.

Show Notes: http://optionalpha.com/show172

This week on the podcast we're doing something a little different and turning this podcast episode into a full-blown audiobook. Today I'm recording the newest book we 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. We've included dozens of charts, tables, and graphs to help as part of this new book and we hope you enjoy listening or reading your copy.

Show notes: http://optionalpha.com/show171

Today on the show we welcome special guest, Rob, who's the co-author on our recent research report on Covered Calls. On the show this week we go over the top three performance insights we learned from our massive study on Covered Call Performance. If you trade covered calls right now or plan on using them at any point when dealing with assigned stock, then this show should be required listening.

Show notes: http://optionalpha.com/show170

Factor-based strategies and trading systems are all the rage these days. We've been promoting these for many years now but it seems that more and more investors are catching on. As a result, we wanted 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.

Show notes: http://optionalpha.com/show169

This week we're very excited to share our exclusive interview with Kevin Davitt, a special guest with tons of experience not only as a former market maker, but as the Senior Instructor for The Options Institute at CBOE. As many long time listener's know, we are highly selective with people we choose to bring on as guests for interview and Kevin raises the bar yet again for us with an amazing discussion. During the show we'll touch on everything from his time as a market maker, transitioning to the retail side of trading, though processes on managing positions and controlling risk, and so much more. You're going to love this candid and wide-ranging discussion as much as we enjoyed the time with Kevin.

Show notes: https://optionalpha.com/show168

Did you know that fear has nothing to do with logical or cognitive reasoning? It's actually a completely physical response that originates in our body. We fear to be wrong because that might mean we will be alone and people will leave us, which means that we won't be part of a tribe or community, which means it'll be dangerous and we might die. Okay, that's extreme but taken to its logical conclusion we fear because of conditioning we've had as humans for thousands of years to survive on a physical level.

As options traders, we have fears about trading that manifest in dozens and dozens of ways. Today, as we circle the Halloween season, I wanted to tackle the 27 biggest options trading fears that we hear in our community. And, more importantly, how to overcome and conquer these fears. Just saying them out loud and talking through them together might just be what you need to set yourself free and on the right path as a trader. 

Show notes: http://optionalpha.com/show167

Oh, profit targets. The double edge sword of confusion for many traders. Take profits too early and you feel like you left money on the table. Too late and you kick yourself because the trade could have moved against you. And because we've been getting so many questions on when and why we've let positions go beyond traditional profit targets, we wanted to record today's show to talk about the top 3 market setups that would lead us to break profit-taking rules. Yes, you heard me right, and longtime members have known this for years, but we don't always take profits at 25% and 50%. Shocking? Shouldn't be because our Profit Matrix research 2 years ago laid the foundation for holding positions generally longer towards expiration.

Show notes: https://optionalpha.com/show166

When it comes to market signals and timing indicators, the Put Call Ratio is one that naturally jumps to the top of many lists. Because the indicator looks at volume in both put and call options, the logical conclusion is that we can interpret the ratio to signal us from an impending top or possible market bottom. But, is that really the case, and if so, how should we use Put Call Ratios moving forward in our analysis. All this and more on this week's podcast episode.

Show notes: https://optionalpha.com/show165

Personally, I don't like rules. Mostly because I value freedom and flexibility so when someone says that I have to follow the rules I naturally push back. Things that confine me or tell me what to do don't fly well with me. But that only applies to things outside of trading and investing. In the world of investing, and specifically trading options, you need to live by certain rules. Rules that keep you safe and protected from the unknown of the market.

I imagine that the 11 "Golden Rules" I'm going to present in this podcast will cause many of you to push back and challenge their usefulness. Mostly because they'll cause you to trade different than you have in the past, and being different means being uncomfortable. I'm okay with that and I welcome the discussion around them. But don't misinterpret this level of understanding in adoption to also represent flexibility when it comes to these rules. These are "unbreakable" rules for me and should be for you as well.

Show notes: http://optionalpha.com/show164

Since we are option sellers and our edge comes from selling overpriced options out into maturity it's natural to assume that if we want to sell options when IV is high that buying options during low IV markets is a way to make money in the other direction. We get it and understand the rationale argument. When IV is low, and option premiums are cheap, you can and should buy options because they are cheap right? Not so fast bargain-buyer.

This type of thought process and strategy, low IV option buying, has two major problems. And we don't use the word "major" lightly here. Each problem with option buying systems is so important that the probability of getting both problems right or solved is for all intensive purposes, impossible on a long timeline. Curious to know what these major issues are? Let's dive into today's show and find out.

Show notes: http://optionalpha.com/show163

This was a long trade. Maybe not the longest trade we've been involved in, but certainly one of the top ones as this short put option assignment lasted over 5 months. For most options traders looking to make a quick buck, this trade stretches their patience and conviction far beyond a reasonable level. Still, I think that today's case study is important to hear because it proves critical concepts to how we think about trading here at Option Alpha. And what better way to prove something than to show you how we managed the entire position, start to finish, with real money.

Show notes: http://optionalpha.com/show162

It might seem that the markets are a game of price, and while that might be mostly true, what they are is really a game of emotions. With enough self-awareness, the "average" investor can do incredibly well. Better than many sophisticated investors.

There's so much to be said about controlling your emotions and recognizing biases that we could spend hours upon hours dissecting each one. I prefer a more optimized approach which is why I decided to do a podcast specifically on the top 8 biases that investors fall victim to. Once you learn to recognize them, you can then process the emotions behind the scenes so that it doesn't interfere with your trading.

Show notes: http://optionalpha.com/show161

As many of our long-time listeners know, over the years I've become increasingly protective and selective with the guests that I invite to come on the show. Truth be told, we get pitched weekly for people looking to expand their reach. Somethings it's just so off the wall and disconnected to trading that I have to laugh. But this isn't the case with today's guests which I'm super excited to bring on for an interview.

Kevin Smith and Tavi Costa both generously gave their time to join me for an incredible look inside their philosophy and macro models at Crescat Capital, a hedge fund based in Denver Colorado. This is an episode you won't want to miss. In fact, I encourage you to listen to it at least twice to make sure you pick up on all the little details you might have skipped the first time around.

Show notes: http://optionalpha.com/show160

Newest platform updates.

Show notes: http://optionalpha.com/show159

This podcast is a long-time coming but one that needed to be done because we get a lot of questions from newbie traders about how to build an options portfolio with a small amount of starting capital. And while we openly suggest that you really start trading with at least $5,000 or more, as you'll hear me say a bunch in this show, we realize that a good majority of new traders want to start with less. That's why in today's show we'll play "pretend" and assume you absolutely want to start trading with just $3,000.

Inside I'll walk through my though process on building out a portfolio that gives you the highest possible chance of success. We'll cover everything from position sizing, ticker selection, strategies to use, what ranges or targets for setting them up, profit taking and stop losses, and much more. The concepts we'll cover are applicable to any portfolio size so don't think or one second that this show is just for small account traders. If you trade a larger account size you can also pick up a lot of great nuggets of information.

Show notes: http://optionalpha.com/show158

Somewhere, possibly from another planet, this notion of trading options with a high probability of success transformed into a subconscious greed for 100% probability of success trades. And if you think that this mentality doesn't exist in the modern market we are in, you should see the emails we get at Option Alpha on a weekly basis. The truth is that you are going to have losing trades, a lot of them over the course of your career. Sometimes they'll come in groups and bunches that make you question everything you are doing or the strategy/system you are choosing to use. But, the first step on your road to elevating yourself is to ask yourself, "Can I trust the process?".

Show notes: http://optionalpha.com/show157

A couple of weeks ago I was reading the story of the three little pigs to my daughters. And for some reason, I couldn't help but think about the untold story of the three little pigs who traded options? Yes, it's true, many people don't know this but the three little pigs were actually given a large chunk of money from their mother and each decided to trade wildly different options portfolios when they set out on their own. In today's podcast, I'll walk through each of the different portfolios they used and how volatility and variance can impact long-term performance and why it's important that we know the story of the three little pigs that traded options.

Show notes: http://optionalpha.com/show156

Many of our members understand the best times to trade options (i.e. higher IV setups when option premiums are expensive), but should we avoid trading during other market situations? Today's podcast walks through the four general market situations I avoid aggressively trading in and explain why each type requires that you either sit on the sidelines or dramatically scale back your position size.

Show notes: http://optionalpha.com/show155

Everyone loves a good options trading checklist right? Well, here are the 7 questions you should ask yourself before you put on an options trade. Answer each one over the next week and you'll build a strong habit that will keep your positions and portfolio in check before you put your hard earned money at risk.

Show notes: http://optionalpha.com/show154

We get a lot of emails each day - I'm talking hundreds of emails. Naturally, seeing so many questions and comments come through the system, we found that these 17 top questions keep coming up again and again. So, in an effort to help you, and our team reduce the support inquiries, I'm recording answers to each of these questions in today's show.

Show notes: http://optionalpha.com/show153

Assignment for some traders can be scary and cause them to freeze up or throw in the towel. On today's podcast, we'll walk-thru another case study in which we got assigned on our iron butterfly position in TLT not once, but twice. Inside I'll move slowly as we look back at each stage in the trade from the original order entry, adjustments, assignment, and ultimately the covered calls we sold after being assigned stock. This podcast is worth listening to twice!

Show notes: http://optionalpha.com/show152

You're looking at a great setup for a neutral trade, but which neutral strategy do you use? Short straddle or short iron butterfly? It's a question we get all the time and today's podcast focuses exclusively on the trade-offs of using one strategy over the other. And while both strategies are built using the same core short straddle position, the choice of adding protection or not using long OTM options can sometimes lead to analysis paralysis. So, let's clear this hurdle together.

Show notes: http://optionalpha.com/show151

All over the internet, you'll hear stories of why short straddles and short strangles should be avoided at all costs. Stories of how trading "undefined" risk positions can blow up your account when the market moves against you quickly. And while position sizing still needs to be managed appropriately, the fact remains that properly adjusting short straddles and rolling for duration and premium can help turn so-called losers into profitable positions. In today's show, we'll focus on our most recent case study in EWZ in which we turned this losing set of straddles into a $540 winner with a little patience and some mechanical adjusting.

Show notes: http://optionalpha.com/show150

As much as I love options trading and following the financial markets, I enjoy the challenge and process of building wealth. I think about wealth building as a 3-step process in broad terms, possibly in the shape of a pyramid even. And since it's our 150th show, I figured I would take a slightly new angle in today's podcast and discuss what I believe are the most valuable insights I can offer from my own experiences and research on how to manage your money and generate wealth. Plus, we'll use this 3-step or 3-part approach to help frame the conversation as best we can.

Show notes: http://optionalpha.com/show149

For some reason, many traders fear being assigned option contracts as part of an option strategy. Maybe it's the large capital requirement to hold the shares or just the "unknown" around how to manage the position. But, like most things in life, when you slow down and take the time to walk through the position and the mechanics it becomes much easier.

On today's show, I want to once again provide another case study on how we managed a recent assignment on our GLD iron butterfly position. If was fun for me to go back through my own comments and remarks during this 4-month trade and I have no doubt that you'll also find it extremely helpful. We'll take you through each and every step from the initial trade entry, adjusting and inversion, being assigned shares, selling covered calls, etc. No details will be left out and we'll walk through the P&L calculations together step by step. Let's begin, shall we?

Show notes: http://optionalpha.com/show148

No system is perfect. No trader is perfect. You will have losing trades. But it's how you react to those losing trades, or even false positive trades, that defines how long you'll survive in this business. Today's show focuses on what I'm calling the 5x2 "Victim Matrix" in which there are 2 paths you can take follow each and every trading event. Each path has 5 stages or steps. Which path should you choose? Well, it's all inside our latest podcast episode.