Cecilia Ziniti’s started as a paralegal at Yahoo in the early 2000s, when Yahoo was competing with Google and the internet was still being shaped by questions about content moderation, trust and safety, and what it meant to serve millions of users.

She went to law school, then joined Morrison & Foerster, where she represented big brands like Apple. At Amazon, she was the founding lawyer on Alexa - she remembers getting excited about the first user review for a product that would eventually ship billions of devices. She eventually became general counsel at Replit, the developer platform used by millions of programmers.

It was at Replit, in early 2022, that things changed. Cecilia had access to a pre-ChatGPT version of GPT through a deal she herself had negotiated between Replit and OpenAI. She tried it on a legal question. The result gave her chills. Her boss at the time, Replit CEO Amjad Masad, eventually noticed her attention had shifted. He asked whether her head was still in it. It was not. She left Replit and founded GC AI a week later, alongside co-founder and CTO Bardia Pourvakil, a fellow Replit alumnus. The company has since raised $73 million in total funding, including a $60 million Series B led by Scale Venture Partners and Northzone. It now powers over 1,400 companies, from Zscaler to Liquid Death. Cecilia was recently named to Inc.’s 2026 Female Founders 500 list.

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I spoke with Javed Qadrud-Din, co-founder and CTO of General Legal - the AI-native law firm backed by Y Combinator, built to serve growth-stage companies.

Javed has been coding since the age of nine. He went to Harvard, detoured into law at Fenwick & West, then decided he’d rather build things than advise on them. He got deep into deep learning in 2014, built what’s been described as the first semantic search system in legal at CaseText - before GPT existed - and was part of the team behind a multi-million exit to Thomson Reuters in 2023.

Now at General Legal, Javed is rebuilding how legal services are delivered: flat fees, and a three-hour turnaround time.

We discussed:

→ Javed’s extraordinary background and how General Legal came about

→ The difference between being AI-native and being AI-powered

→ What the economics of flat-fee legal services look like under pressure, and whether $500 per contract goes down as AI improves.

→ Why founders using free ChatGPT to draft contracts are “yoloing it”.

→ His vision for what the legal industry looks like in 2030 - and what lawyers should be doing today to prepare.

I hope you enjoy!

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I spoke with Ross McNairn, co-founder and CEO of Wordsmith AI, who trained as a lawyer, retrained as a software engineer, and spent over a decade scaling companies like Skyscanner and TravelPerk.

When he got early access to OpenAI’s AI tool, he quit his CTO role to get building in legal AI.

Wordsmith is built exclusively for in-house teams - connecting legal to the business through AI-powered workflows.

We discussed:

→ How the relentless focus on going after "in-house" led them to build the product they have today.

→ The difference between building AI for law firms versus in-house teams.

→ Why Wordsmith aren't worried about OpenAI or Anthropic "going vertical".

→ What Ross looks for when hiring new employees at Wordsmith.

→ His vision for what the future of an in-house lawyer role will look like.

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Ruben Miessen spent years leading the product teams at Tinder and Match Group, where sitting through weekly legal committee meetings helped him develop a deep understanding of the processes that caused bottlenecks and frustrations.

Rather than build another generalist legal AI tool, Ruben co-founded LegalFly in 2023 with a laser focus on in-house legal and procurement teams at enterprises in highly regulated industries.

The Belgian startup now employs over 50 people across Ghent, London, and Dubai, and closed 2025 with 600% year-over-year growth - with 80% of clients coming inbound rather than through outbound sales.

In this episode, I ask Ruben:

* Why he built exclusively for in-house teams instead of law firms - and why that choice shaped everything from product to go-to-market.

* The role European data privacy regulations played in LegalFly’s product architecture and competitive positioning.

* His predictions for legal AI consolidation in 2026 - and why he thinks data quality will matter more than ever.

* Plus, the roadmap for LegalFly’s Series B and US expansion plans.

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Alexander founded and led Safe Sign Technologies, a frontier AI startup specialising in Legal LLMs whilst he was training at Allen & Overy. The Cambridge- and MIT-based start-up was acquired in a blockbuster exit by Thomson Reuters in August 2024.

In this first episode, I ask Alexander:

• How he built a successful legal AI company while managing the intense workload of a Magic Circle training contract.

• The critical debate for legal tech - is the future in off-the-shelf LLMs or custom-training foundational models?

• Why Big Tech's verticalisation (like DocuGPT) is creating a market squeeze for new legal AI startups.

• The potential collapse of the law firm 'pyramid' as AI handles the work of the £150k+ junior associate.

• Plus, predictions for the legal AI landscape in 2026 and the changing risk-reward for law students.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.bestpractice.media