What can bar bets, coin flips, and the length of your subway commute teach us about options pricing? In this episode of Excess Returns, Matt Ziegler is joined once again by Kris Abdelmessih to break down complex options theory into intuitive, real-world analogies. From prediction markets to probability distributions, Kris helps us understand how the options market reveals what the stock market often hides—how investors are pricing not just if something happens, but how much it matters when it does. This is options math with a twist, taught like you’re five, but ready for Wall Street.

📈 Whether you're an investor trying to size a high-risk, high-reward position, or simply curious about how the market “thinks” about uncertainty, this episode is full of mental models you’ll want to revisit.

📌 Topics Covered:

• Coin flips vs. futures: the two dominant styles of betting

• Over/under bets and what they teach us about prediction markets

• Why odds ≠ probabilities—and how to convert between them

• The difference between probability and magnitude in financial outcomes

• Bar bets and beer-drinking contests on Wall Street (!?)

• Using call spreads to isolate probabilities, not potential profits

• A visual breakdown of skewed vs. symmetric return distributions

• Why two stocks can have the same price but completely different implications

• How the options market understood the dot-com bust better than most investors

• Why thinking in bets makes you a better investor and allocator

⏱️ Timestamps:

00:00 – The stock market vs. the options market
01:42 – Over/under bets and their connection to options
05:59 – Understanding prediction markets and odds
10:00 – Future-style bets: Magnitude vs. probability
14:35 – The subway commute example and tail risk
19:00 – Why volatility and skew matter in pricing
20:38 – Stock A vs. Stock B: Same price, different outcomes
24:00 – Visualizing probability distributions
28:00 – How call values reflect both vol and probability
32:00 – Truncating the tail: turning options into “bar bets”
35:00 – Using call spreads to extract implied probabilities
37:00 – What investors can learn from this framework
39:00 – Options markets during the dot-com bubble
40:45 – Where to follow Kris online

🎙️ Guest: Kris Abdelmessih
🧠 Follow Kris’s work: https://moontower.substack.com

What if the biggest market moves aren't driven by fundamentals—but by flows you can't see?

In this episode, Brent Kochuba of SpotGamma joins us to explain the hidden mechanics of the options market that are quietly reshaping stock prices. We explore how dealer hedging, gamma squeezes, and volatility dynamics like Vanna and Charm are influencing everything from individual stocks to the S&P 500. Whether you're an active trader or a long-term investor, understanding these forces is crucial to interpreting today’s markets.

We discuss:

• Why dealer flows are moving billions in stocks each day

• What Gamma, Vanna, and Charm really mean—and why they matter

• How implied volatility creates powerful reflexive market moves

• Why options expiration dates often mark key turning points

• What long-term investors should know about short-term flows

• Real-world examples: GameStop, Tesla, Nvidia, COVID, and more

Even if you never trade an option, this conversation will change how you think about market behavior.

In this episode of Teach Me Like I'm 5, options expert Kris Abdelmessih breaks down one of the most foundational—and misunderstood—concepts in options trading: put-call parity. Using Lego analogies, homemade spreadsheets, and Fast & Furious references, Kris shows how options are like building blocks you can combine to create any payoff you want—including replicating a stock itself.

Whether you're a beginner trying to understand options basics or a seasoned investor looking for deeper insights into synthetic positions and implied interest rates, this episode is packed with practical lessons presented in the most approachable way possible.

What We Cover:

Why calls and puts are “the same” through the lens of put-call parity

How to visualize and replicate stock payoffs using only options

The concept of synthetic positions: synthetic stock, calls, and puts

How put-call parity collapses complex strategies into basic building blocks

The real mechanics behind covered calls—and what they really are

How professional traders use options pricing to infer interest rates and stock borrowing conditions

A deep dive into "box spreads" and how they replicate zero-coupon bonds

In this episode of our new show Teach Me Like I'm 5, we’re joined by Mat Cashman, Principal of Investor Education at the OCC, to break down a powerful yet often overlooked concept in options trading: the Rule of 16. Whether you're new to volatility or a market veteran, this conversation takes you from the sandbox to the risk desk, explaining how this simple rule transforms annualized volatility into daily insight—and how professionals use it to assess market surprises, portfolio risk, and trading decisions.

What We Cover:

What the Rule of 16 is and why it mattersTranslating annualized volatility into daily expectations

Why understanding standard deviation helps traders interpret large price moves

How experienced traders use the Rule of 16 to adjust to fast-changing volatility

Real-world examples including recent five-standard-deviation events

The psychological and behavioral impact of “surprising” moves on market participantsHow to build a daily baseline for expected price movement

Using the Rule of 16 to contextualize options positions and risk management