Opting For Wisdom: Options Trading Basics

Opting For Wisdom: Options Trading Basics

From Thoughts On Money [TOM] by Trevor Cummings

February 27, 2026 · 40 min

About this episode

Trevor Cummings interviews Brett Bonecutter about the complexities and risks of options trading, highlighting personal experiences and broader market implications.

This week's blogpost - https://bahnsen.co/4rAtQvD Trevor Cummings, hosting with a lost voice, interviews blog author Brett Bonecutter about his COVID-era entry into the options-trading subculture after being taught by a former bond trader. Brett describes early euphoric gains from a single strategy in a favorable market that led to confirmation bias, followed by significant losses when conditions changed and he wasn’t nimble enough to adapt, noting how traders often highlight winning trades while ignoring the full sample. They explain options as time-bound contracts to buy or sell an underlying asset (calls and puts), including how contracts themselves can be traded, and warn that complex combinations can create severe or even unlimited losses, citing a widely reported case of a confused young options trader who took his life and examples like meme-stock squeezes. They contrast investing vs speculating, critique overreliance on technical analysis, and conclude options are best for professional hedging, not retail “tinkering,” despite get-rich-quick allure. 00:00 Welcome and Setup 01:07 Subcultures and Finance 02:32 COVID Options Rabbit Hole 05:32 Highlight Reels and Bias 08:34…

People in this episode

Host: Trevor Cummings

Guest: Brett Bonecutter

Topics covered

  • options trading
  • investing
  • speculating
  • technical analysis
  • COVID-19

Keywords

  • confirmation bias
  • derivatives
  • hedging
  • meme stocks

Mentioned in this episode

Books & works: Opting For Wisdom

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