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  1. The Acquirers Podcast
  2. Value Investing with Options: Selling Puts to Buy Wonderful Businesses at Better Prices | S08 E18
Value Investing with Options: Selling Puts to Buy Wonderful Businesses at Better Prices | S08 E18

Value Investing with Options: Selling Puts to Buy Wonderful Businesses at Better Prices | S08 E18

The Acquirers Podcast · May 27, 2026

Use value investing principles with options by selling cash-secured puts to generate income or acquire great businesses at a discount.

Covered Call Strategies Underperform in Power-Law Driven Portfolios

Selling covered calls caps a stock's upside potential. This makes the strategy a poor fit for portfolios relying on a few massive winners to drive returns, as it trades home runs for more frequent but smaller gains.

Value Investing with Options: Selling Puts to Buy Wonderful Businesses at Better Prices | S08 E18 thumbnail

Value Investing with Options: Selling Puts to Buy Wonderful Businesses at Better Prices | S08 E18

The Acquirers Podcast·3 days ago

The "Wheel" Strategy Systematizes Income Generation By Cycling Puts and Calls

The "wheel" is a continuous options strategy. An investor sells cash-secured puts to acquire a stock at a discount. If assigned, they then sell covered calls against the new position until it is called away, at which point the cycle restarts.

Value Investing with Options: Selling Puts to Buy Wonderful Businesses at Better Prices | S08 E18 thumbnail

Value Investing with Options: Selling Puts to Buy Wonderful Businesses at Better Prices | S08 E18

The Acquirers Podcast·3 days ago

Efficiency Gains Are Visible on Spreadsheets, While System Resilience Is Invisible Until Crisis

It's easy to measure and reward efficiency—fewer crews, less inventory. The value of resilience—the train that isn't delayed, the factory that doesn't shut down—is a non-event and therefore invisible on financial statements until it's too late.

Value Investing with Options: Selling Puts to Buy Wonderful Businesses at Better Prices | S08 E18 thumbnail

Value Investing with Options: Selling Puts to Buy Wonderful Businesses at Better Prices | S08 E18

The Acquirers Podcast·3 days ago

Sell Cash-Secured Puts on Undervalued Stocks to Create Better Entry Points

Value investors can use options as a tactic. By selling a cash-secured put, you either earn a premium if the stock stays above the strike price or you acquire a stock you already want at a pre-determined, lower effective price.

Value Investing with Options: Selling Puts to Buy Wonderful Businesses at Better Prices | S08 E18 thumbnail

Value Investing with Options: Selling Puts to Buy Wonderful Businesses at Better Prices | S08 E18

The Acquirers Podcast·3 days ago

Toyota Reintroduced Supply Chain Slack After an Earthquake Proved Lean Manufacturing Fragile

After the 2011 Japan earthquake decimated its supply chain, Toyota reversed its famous "just-in-time" philosophy. It mandated key suppliers hold two to six months of inventory, deliberately sacrificing peak efficiency for greater resilience.

Value Investing with Options: Selling Puts to Buy Wonderful Businesses at Better Prices | S08 E18 thumbnail

Value Investing with Options: Selling Puts to Buy Wonderful Businesses at Better Prices | S08 E18

The Acquirers Podcast·3 days ago

Option Prices Misalign with Fundamentals When Volatility Is the Key Input

Options pricing models heavily weigh recent stock volatility. This creates opportunities for value investors who can assess a business's fundamental risk as being lower than its volatility-inflated option premiums suggest, especially after a large price drop.

Value Investing with Options: Selling Puts to Buy Wonderful Businesses at Better Prices | S08 E18 thumbnail

Value Investing with Options: Selling Puts to Buy Wonderful Businesses at Better Prices | S08 E18

The Acquirers Podcast·3 days ago

High Switching Costs Insulate Enterprise SaaS Leaders from AI-Driven Disruption

Even if AI makes it easier to build competing software, incumbent SaaS giants retain customers due to immense switching costs. The operational disruption, retraining, and integration challenges of migrating a large organization create a powerful moat against new entrants.

Value Investing with Options: Selling Puts to Buy Wonderful Businesses at Better Prices | S08 E18 thumbnail

Value Investing with Options: Selling Puts to Buy Wonderful Businesses at Better Prices | S08 E18

The Acquirers Podcast·3 days ago

Precision Scheduled Railroading Shows How Efficiency Gains Create Systemic Fragility

The railroad industry's shift to hyper-efficient scheduling (PSR) removed operational slack like extra crews and yard capacity. While this improved financial metrics, it created a fragile system where one delay could cascade, a lesson applicable to any complex system.

Value Investing with Options: Selling Puts to Buy Wonderful Businesses at Better Prices | S08 E18 thumbnail

Value Investing with Options: Selling Puts to Buy Wonderful Businesses at Better Prices | S08 E18

The Acquirers Podcast·3 days ago

AI Revolution Will Invert COVID's Impact, Threatening White-Collar Jobs Over Blue-Collar

While the pandemic primarily affected blue-collar workers who couldn't work remotely, AI is automating knowledge-based tasks. This suggests a reversal where physical, blue-collar jobs like wiring a data center become more secure than many white-collar roles.

Value Investing with Options: Selling Puts to Buy Wonderful Businesses at Better Prices | S08 E18 thumbnail

Value Investing with Options: Selling Puts to Buy Wonderful Businesses at Better Prices | S08 E18

The Acquirers Podcast·3 days ago