7/21/25

Square vs Toast, AI Red Flags, Sales Mistakes, and Real Leadership | Ep. 4

We’re doing the impossible: Making business content that’s sharp, useful, and actually fun to watch.

In this episode, we cover:

Tech News

• The Square vs. Toast war no one’s talking about

• Google Cloud’s outage. Was it just a config bug or something deeper

• AI models trained on books without permission, plus the questions that separate hype from real magic

AI

• The exact questions to ask before trusting any so-called AI tool

• How to use AI to create leverage without creating dependency

• Where people get it wrong when they plug in automation too early

Sales

• Correlation vs. causation in sales

• Why copying influencer tactics won’t fix your close rate

• How to focus on what actually moves deals forward

Leadership

• Rethinking hierarchy as a role, not a rank

• Why good leaders build and iterate

• What it really means to lead inside a system

If you’re building something real and tired of recycled advice, this one’s worth your time.

Previous

AI’s Impact: Sports, Hiring Wars, and Sales Shifts

Next

The Process | Ep. 3