Instead of paying lawyers $50,000 for deal diligence, Union Square Ventures' Fred Wilson used Google's free AI tool, NotebookLM. He uploaded past deal documents and the new startup's data room into separate "notebooks" and used AI to interrogate the differences, collapsing weeks of expensive work into a few hours.

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Startups are increasingly using AI to handle legal and accounting tasks themselves, avoiding high professional fees. This signals a significant market need for tools that formalize and support this DIY approach, especially as startups scale and require more robust solutions for investors.

Instead of relying on subjective feedback from account executives, Vercel uses an AI agent to analyze all communications (Gong transcripts, emails, Slack) for lost deals. The bot often uncovers the real reasons for losing (e.g., failure to contact the economic buyer) versus the stated reason (e.g., price).

Instead of walking into a pitch unprepared, Reid Hoffman advises founders to use large language models to pre-emptively critique their business idea. Prompting an AI to act as a skeptical VC helps founders anticipate tough questions and strengthen their narrative before meeting real investors.

Individual sellers can use free tools like Google's NotebookLM to build their own specialized AI agents now. By uploading books, articles, and podcasts on topics like prospecting or upselling, they create a personal knowledge base to get instant, tailored answers and stay ahead of the curve.

Unlike simple "Ctrl+F" searches, modern language models analyze and attribute semantic meaning to legal phrases. This allows platforms to track a single legal concept (like a "J.Crew blocker") even when it's phrased a thousand different ways across complex documents, enabling true market-wide quantification for the first time.

To make company strategy more accessible, Zapier used Google's NotebookLM to create a central AI 'companion.' It ingests all strategy docs, meeting transcripts, and plans, allowing any employee to ask questions and understand how their work connects to the bigger picture.

Within the last year, legal AI tools have evolved from unimpressive novelties to systems capable of performing tasks like due diligence—worth hundreds of thousands of dollars—in minutes. This dramatic capability leap signals that the legal industry's business model faces imminent disruption as clients demand the efficiency gains.

AI tools can instantly parse, reformat, and summarize dense documents like congressional bills, which would otherwise require significant manual cleanup. This capability transforms workflows for analysts and researchers, reallocating time from tedious data preparation to high-value strategic analysis.

Venture capitalist Keith Rabois observes a new behavior: founders are using ChatGPT for initial legal research and then presenting those findings to challenge or verify the advice given by their expensive law firms, shifting the client-provider power dynamic.

The legal profession's core functions—researching case law, drafting contracts, and reviewing documents—are based on a large, structured corpus of text. This makes them ideal use cases for Large Language Models, fueling a massive wave of investment into legal AI companies.

VC Fred Wilson Used Google's NotebookLM to Replace $50K in Legal Fees | RiffOn