Anthropic has filed its S-1, and Rick Watson and Jessica Lesesky use the filing to ask whether software companies are in real trouble. Reported targets put the raise at $100 billion or more at a valuation of up to $2 trillion, which would top SpaceX. OpenAI, meanwhile, has pushed back its IPO and is reportedly raising $30 billion privately at about $1.4 trillion.

Jess goes back to the software selloff earlier this year, when investors decided Claude Code and Cowork would kill SaaS, a prediction that hasn’t come true yet. Rick thinks the old buy, build or partner decision now comes down to build, because marketing teams believe they can vibe code their own tools. Jess expects systems of record like NetSuite and Salesforce to hold up and worries more about the small and mid-tier apps someone could rebuild overnight. They also get into what a moat means when code is cheap, and a website that lets prospects check whether your product is just a markdown file.

The IPO race splits them. Rick says OpenAI is making a mistake by waiting while Dario Amodei takes Anthropic public. Jess thinks Sam Altman is playing it like Apple, letting someone else go first and arriving later with something better.

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