OpenAI, SBF & Perplexity: What VCs Know That You Don’t

Rory O’Driscoll and Jason Lemkin argue Tiger Global’s OpenAI/Scale bets could salvage a disastrous 2021 vintage, and explain why Perplexity at $14B is a rational ‘at-bat’ on a trillion-dollar prize.

• Tiger Global’s $12B fund only works if they allocated 10-15%+ to OpenAI and Scale; $100M increments cannot dig out of that hole.
• SBF’s FTX positions in Anthropic and Cursor would have covered fund losses if not for the fraud and commingling.
• Perplexity is framed as a credible one-in-three shot at a trillion-dollar search outcome; Jason Lemkin disclosed he is an investor.
• Owner raised $120M at $1B valuation growing ~10% MoM; triple-triple-double-double growth still unlocks essentially unlimited capital.
• Series A volume down 81% per Carta; hosts argue this is correct — B-tier startups shouldn’t get funded, S-tier still gets five term sheets.
• OpenAI is converting to a public benefit corporation structure, mirroring what Anthropic built from day one, to resolve nonprofit/for-profit conflict.
• Microsoft’s OpenAI deal — 10% of all revenue until AGI plus equity — went from looking like a weird antitrust workaround to an epic investment.
• Clay is winning on CMO fear: marketers writing six-figure checks to avoid job loss, but competition is intensifying fast and hosts say Clay should raise another $100M war chest.

2025-05-15 · Watch on YouTube