Macro Duration Risk And Financing-Continuity As An Existential Variable
Sources: 1 • Confidence: Medium • Updated: 2026-02-20 09:15
Key takeaways
- A counter-argument presented is that OpenAI is not a credible goes-to-zero case because it has a massive user base (claimed ~800M), subscriptions, and a real business.
- Andreessen Horowitz raised $15B, representing over 20% of total venture funds raised in 2025.
- Substitution and cost-rotation pressures in AI software are expected as buyers start actively reducing stacked AI vendor fees.
- Anthropic raised $10B.
- Among CPOs the host speaks with, Claude Code is increasingly the default internal tool and Cursor usage has dropped significantly over the last three months.
Sections
Macro Duration Risk And Financing-Continuity As An Existential Variable
- A counter-argument presented is that OpenAI is not a credible goes-to-zero case because it has a massive user base (claimed ~800M), subscriptions, and a real business.
- OpenAI is described as facing existential risk.
- The current market narrative is described as treating the odds of an economic downturn as effectively impossible.
- The most acute downside scenario for frontier AI companies is described as the combination of continued strong scaling-driven improvements and macro conditions that restrict capital access.
- A bear case presented for OpenAI is that LLMs have very short effective shelf life (claimed <100 days) and that if a macro shock prevents raising the next roughly $100B needed for scaling, OpenAI could freeze and lose relevance to better-funded competitors.
- The core bet being made in current pricing is that exceptionally favorable market conditions persist for at least a decade.
Venture Consolidation, Scale Mechanics, And Correlated Late-Stage Risk
- Andreessen Horowitz raised $15B, representing over 20% of total venture funds raised in 2025.
- Andreessen Horowitz is described as effectively operating multiple roughly billion-dollar boutique funds rather than one monolithic pool for investing decisions.
- By Series C, about 80% of deals are described as having at least one hard-to-beat top-tier investor on the cap table, versus about 40–50% at Series A.
- Early-stage venture is described as primarily taking uncorrelated business risk, while late-stage investing is described as dominated by highly correlated valuation risk.
- Late-stage investing is described as dominated by correlated valuation risk where small growth slowdowns can cause large multiple compression across many companies simultaneously.
- When opportunities feel obvious and growth appears linear, valuation is described as expanding to absorb remaining uncertainty, leaving investors primarily exposed to valuation risk rather than business risk.
Demand-Side Substitution And Pricing Pressure In Ai Software
- Substitution and cost-rotation pressures in AI software are expected as buyers start actively reducing stacked AI vendor fees.
- A view presented is that ElevenLabs is too risky to invest in at an $11B valuation due to perceived fragility and near-term substitution risk.
- For ElevenLabs, defensibility and the ability to justify an $11B entry valuation is described as depending on whether revenue is broadly distributed across many smaller customers rather than concentrated in a few large accounts.
- Since the latest Gemini releases, ChatGPT usage is cited as having declined by about 22%.
- Free alternatives can rapidly pull users away from paid AI products, illustrated by a user switching off paid ChatGPT while continuing to pay for Cursor.
- Compute cost declines over time are expected to improve gross margins for digital products that are not gross-margin positive today.
Ai Capital Intensity And Mega-Round Normalization
- Anthropic raised $10B.
- xAI raised $20B.
- Anthropic’s reported revenue run-rate was about $100M at end-2023, about $1B at end-2024, and allegedly $9–10B at end-2025.
- If Anthropic sustains strong growth for one more year, a $350B valuation could look inexpensive on forward revenue multiples (example framework: ~17x NTM revenue under a 3x run-rate scenario).
- Anthropic’s $10B round was at a $350B valuation and is likely its last private round before an IPO.
Platform Dependency And Supplier Control Risk For Ai Apps
- Among CPOs the host speaks with, Claude Code is increasingly the default internal tool and Cursor usage has dropped significantly over the last three months.
- Cursor’s competitive risk is described as highly price-dependent because it competes with Microsoft/GitHub and also faces supplier competition risk from Anthropic.
- Anthropic reportedly cut off xAI’s access to Anthropic models.
- Model providers can restrict top-model access, degrade service, or copy downstream applications when incentives change, creating platform dependency risk for AI application companies.
- In the current AI market, existential competitive risk can arrive on roughly a six-month cadence.
Watchlist
- Early reviews of Anthropic’s knowledge-work workspace product are described as impressive but somewhat janky.
- OpenAI is described as facing existential risk.
- A counter-argument presented is that OpenAI is not a credible goes-to-zero case because it has a massive user base (claimed ~800M), subscriptions, and a real business.
- Substitution and cost-rotation pressures in AI software are expected as buyers start actively reducing stacked AI vendor fees.
- A proposed wealth tax design is described as estimating ownership based on voting control, which could overstate founders’ economic ownership when they have super-voting shares.
- It is uncertain whether investors can still find $10B outcomes outside the dominant incumbent venture system.
- The current venture environment is described as implicitly pricing near-zero downturn probability, and OpenAI is framed as having existential risk if it requires a decade-long 'best of times' to reliably access capital.
- Jason posits that as venture discovery becomes increasingly efficient via YC and similar networks, the remaining sustainable niche for many VCs may shrink toward inception investing.
Unknowns
- What is Anthropic’s actual recognized revenue (not just run-rate), gross margin, and customer concentration for the period referenced?
- What are the actual terms and structure of Anthropic’s $10B financing (price, liquidation preferences, governance, secondary vs primary)?
- Is Anthropic’s funding round truly intended to be the last private round before an IPO, and on what timeline?
- What are objective adoption and retention metrics for Claude Code versus Cursor in enterprise environments (renewals, paid seats, usage frequency)?
- What is the real-world reliability and workflow completeness of Anthropic’s knowledge-work workspace product, and is it improving rapidly?