Finance Agent v2 (by Vals AI) has emerged as the reference benchmark for evaluating both Anthropic Claude and OpenAI ChatGPT frontier language models on financial tasks. However, it narrowly deals with periodic reporting from publicly traded companies (SEC 10-K and 10-Q filings), and its agentic harness relies on naive, unenriched chunk retrieval. Neither the task design nor the retrieval approach addresses the distinct challenges of IPO due diligence. SEC S-1 filings combine historical financial statements, governance structures, pro forma and common-control accounting treatments, capital-formation narratives, and underwriting-sensitive risk disclosures within substantially longer documents than typical periodic filings. That is why we introduce IPO Finance Agent, which extends the Finance Agent v2 framework along two directions: task domain and retrieval architecture. During our experiments, the original Finance Agent v2 harness basically failed to deliver any output related to the SpaceX S-1 filing, due to document length. We therefore had to improve the agentic harness with contextual retrieval, a more realistic and industry-standard approach for long documents. We also built a dataset of 1,000 IPO-diligence questions, and publicly release 70 questions on the SpaceX (SPCX) S-1 filing to support reproducibility, while the remainder are held private to guard against benchmark contamination. In addition, we introduce an evaluator-optimizer pipeline to automatically generate evaluation rubrics for the benchmark: candidate facts are extracted from model answers, consolidated into draft criteria, then automatically audited for omissions, hallucinations, mistiered items, and redundancy, with LLM feedback driving iterative repair, targeted enrichment, and deduplication. Human experts only review final rubrics before deployment. Results show that the best-performing evaluated model, Alibaba Qwen 3.7 Max, reaches 79.4% accuracy at 0.30 USD per query, and the most cost-efficient model on the resulting Pareto frontier, Xiaomi MiMo-2.5 Pro, reaches slightly lower accuracy (76.8%) at 0.05 USD per query. Both exceed the current Finance Agent v2 leaderboard ceiling-Google Gemini 3.5 Flash at 57.9% for 2.51 USD per querywhile undercutting even FABv2's cheapest entry (MiniMax M3: 48.3% at 0.32 USD) on cost-efficiency. Code and data are released on GitHub: https://github.com/benstaf/ipoagent

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