Can online dating teach us something about legal tech? In the latest episode from Crafty Counsel, Founder Benjamin White takes a walk in the park with Ruben Miessen, co-founder and CEO of LEGALFLY.
Before launching Legal Fly, Ruben and his co-founders worked at Tinder, building AI-powered matchmaking features. Now, they’re using that experience to tackle some of the most pressing challenges in legal AI.
The link between dating apps and legal workflows
Ruben shares three surprising yet insightful lessons from his Tinder days that apply directly to the world of AI in legal tech.
1. Trustworthy AI needs trustworthy data
AI can only be as effective as the data it’s trained on. While Tinder relied on user profiles and swiping behavior, Legal Fly uses court records, contracts, and regulatory updates to train its legal AI tools. Ruben explains how access to millions of high-quality legal documents — through partnerships with law firms and publishers — makes all the difference in building tools that actually work in real-world legal settings.
2. Always keep a human in the loop
Even the best AI models need human oversight. At Tinder, AI helped detect problematic content, but humans made the final call. In legal tech, the same rule applies. AI can highlight compliance issues or redraft clauses, but in-house legal teams still play a critical role in reviewing, validating, and applying those suggestions.
3. AI isn’t replacing the legal process, it is empowering it
Ruben is clear: AI is not here to replace lawyers. Instead, it helps in-house legal teams automate repetitive tasks and shift focus to strategic work. This is especially crucial for small legal teams under pressure, where boosting efficiency can reduce dependence on costly external counsel.
A fresh take on legal tech
This conversation is as refreshing as the park setting itself. With honesty, curiosity, and just a hint of humour, Ruben and Benjamin unpack what it means to build responsible, effective legal AI – without the hype.
Watch the full episode to hear more about Ruben’s journey from Tinder to LEGALFLY, and what legal tech can learn from the dating world.
If you enjoyed this video, be sure to check out our previous video in the series, “Three things I’ve learnt about Employment Law with Dónall Breen”. In this conversation, Donall shares valuable insights about navigating employment law. Watch the video here.