The Wild West of AI: A Legal Tech Reckoning with Ken Crutchfield

Aug 4, 2025

Ken Crutchfield, founder of Spring Forward Consulting, shares insights from his extensive background with legal information vendors. He likens today's AI boom in law to the chaotic American Industrial Revolution, highlighting the lack of regulation amidst hype and overinvestment. Ken discusses the need for law firms to rethink adoption strategies, balancing expectations with startups' limitations, and emphasizes the importance of 'Return on Experience' to maximize tech use. He calls for leadership engagement to navigate this evolving landscape effectively.

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INSIGHT

AI's Wild West Era

AI's rise parallels the American Industrial Revolution's "Wild West" era of rapid expansion and sparse regulation.
Massive investments in AI infrastructure mirror railroads, oil, and steel growth from the 19th century.

INSIGHT

Corporate Giants Rival Governments

Large corporations hold power rivaling governments in shaping AI's trajectory.
Cross-industry influence resembles 19th-century tycoons who built infrastructure and shaped markets.

INSIGHT

Legal Content Protection Challenges

Protecting proprietary legal content will become critical as AI indexing and training evolve.
Licensing terms and content availability may shift significantly post generative AI surge.

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This week, we welcome longtime friend and legal tech veteran Ken Crutchfield, founder of Spring Forward Consulting. Ken brings his extensive experience from major legal information vendors like Thomson Reuters, Bloomberg, and Wolters Kluwer into a timely and candid discussion about the current phase of artificial intelligence in the legal industry. Comparing today’s generative AI surge to the American Industrial Revolution, Ken describes this moment as the “Wild West” era—full of promise, hype, overinvestment, and, critically, few rules.

Drawing historical parallels to railroads, oil barons, and steel magnates, Ken illustrates how unchecked growth and technological innovation can outpace regulation until market forces or policy catch up. He notes the resurgence of large-scale infrastructure investment, now not in steel or steam, but in compute power and data centers. Just as J.P. Morgan helped stabilize chaotic markets in the 19th century, Ken suggests today's AI frontier needs a similar recalibration, and possibly new rules of engagement.

The conversation shifts toward the practical realities of legal tech adoption. Ken emphasizes that law firms' expectations of perfection often collide with startups’ resource limitations. Vendors need to rethink how they engage with firms by building credibility, focusing on integration, and delivering actual use-case wins. Firms, in turn, must move beyond the billable hour mindset and consider new metrics like Return on Experience. Adoption is no longer optional, it’s strategic, competitive, and increasingly client-driven.

Ken also unpacks the looming implications of content rights and data ownership in the age of AI. If firms aren’t investing in data hygiene now, they risk being left behind when more sophisticated AI tools demand clean, structured, and secure datasets. AI isn’t just about automating workflows, it’s about being ready to plug into a future where interoperability, metadata, and permissions will dictate who thrives and who gets leapfrogged.

Finally, Ken calls for scenario planning: not just reacting to what OpenAI or Anthropic might do next, but anticipating it. Firms and vendors alike should double down on what works, define success before launching new projects, and invest in meaningful adoption strategies. In a world moving this fast, it’s no longer about who gets there first, it’s about who gets there with a plan.

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[Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.]

Blue Sky: ⁠⁠@geeklawblog.com⁠⁠ ⁠⁠@marlgeb⁠⁠
⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

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