Run the Numbers

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

Sep 27, 2025
Dive into the quirks of startup culture with tales of sad LinkedIn dinners and baffling AI-driven UX trends. Explore the eyebrow-raising case of a $613M company pushing for an $8B valuation and whether referral programs are a sustainable growth strategy or a marketing trap. The hosts debate the implications of 'prompt anxiety' in software and the ethics of disclosing AI-generated content. Plus, learn about Arnold Schwarzenegger's surprising comedy debut and how Reese Witherspoon cleverly uses her book club to fuel her media empire.
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INSIGHT

Navan IPO Tests The Market

  • Navan (formerly TripActions) IPO tests whether software IPO demand returns for average companies.
  • Size, growth, and cash-burning determine whether a ~$613M revenue company can hit an $8B valuation and attract large investors.
ANECDOTE

Personal Travel-Marketplace Failure

  • CJ recounts his failed travel marketplace that lost him money and taught him about live inventory complexity.
  • He connects that experience to understanding Navan's much larger challenges in T&E systems.
INSIGHT

Usage Revenue Is Recurring — But Different

  • Usage-based revenue can look recurring but is price-and-volume volatile compared to pure subscription.
  • Investors will value Navan differently because a large share of revenue is a take-rate on travel throughput, not a pure SaaS stream.
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