Prompt Anxiety, Sad Dinners, & the $8B Question

AI may be changing how we work, but it’s also changing how we interact with software — and not always for the better. CJ and Kyle Poyar dig into the growing pains of product design, IPOs in weird markets, and the unexpectedly depressing world of startup networking.

• Navan IPO: Why a $613M company burning $80M is still pushing for an $8B valuation — and what it says about the state of software IPOs.

• Prompt Bars Are Everywhere: The rise of “blank box” UX, why every app suddenly looks like ChatGPT, and how that’s giving users prompt anxiety.

• Referral Programs: Ponzi Scheme?: Incentives are up, CAC is down — but is this growth channel actually sustainable or just marketing MLMs in disguise?

• When to Disclose AI-Generated: If your calendar link feels cold, wait until your AI avatar shows up in an ad. We debate where the ethical (and strategic) line is for AI transparency.

• Business Blunders:
  • Sad Dinners (CJ): Why every LinkedIn dinner photo looks depressing — and what it says about startup culture.
  • ChatGPT Bad Chart (Kyle): An incredible dataset ruined by a rainbow mess of tiny fonts and meaningless categories.

• Potentially Reliable Thing at 2AM:
  • Arnold Twins Revenue (CJ): The wild deal behind Arnold Schwarzenegger’s comedy debut — and how it made more money than Terminator.
  • Reese Witherspoon Book Club (Kyle): Viral influence, middle-of-the-night decisions, and what media we trust half-asleep.

• Pricing in the Real World:
  • CJ: Iced Coffee Variable Pricing: Starbucks, cold brew, and the surprising economics of how product pricing actually works day to day.

• Something We Tried This Week:
  • Kyle: Fyxer Virtual Assistant: A hands-on experiment with offloading operational drag — what worked, what didn’t, and what Kyle’s still skeptical about.