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Risky Business

Dave Berner 1 Episodes Oct 2, 2026

Risky Business is a podcast for professionals working in high-stakes industries such as law, healthcare, and fintech. Host Dave Berner, co-founder of the legal AI platform Parachute, has long-form conversations with founders, entrepreneurs, and operators. They explore what it's like to build ventures where the margin for error is slim and regulation is tight, yet the payoff can be substantial when done well. Each episode delves into the challenges and rewards of operating in these demanding fields.

Episodes

Walked away from over $1M revenue to go all-in on legal | Evan Wong Oct 2, 2026 4205 Hey! I'd love to hear your thoughts, send me a voice note.Evan Wong is the co-founder of Checkbox AI - the front door for legal teams, triaging and resolving requests before they ever hit a lawyer's desk.We dive into:Walking away from over $1M ARRUsing a written memo to bring your team and investors on the journeyWhat happens to engineering identity when nobody writes code by handWhy the goal isn'

Why AI Won't Replace Lawyers | Nandan Subramaniam Sep 18, 2026 4373 Hey! I'd love to hear your thoughts, send me a voice note.Why do some lawyers get fired and then build a better business than the firm that let them go?I spoke with Nandan Subramaniam, principal at Zed Law, who runs a fully remote firm from a farm in the Northern Rivers while advising Parachute on where AI actually helps lawyers, and where it doesn't.Zed has automated around 80% of its internal pr

AI makes bad lawyers worse Sep 2, 2026 3800 Hey! I'd love to hear your thoughts, send me a voice note.Daniel Lord-Doyle co-founded Mary Technology after watching his co-founder Rohan struggle through his first weeks as a lawyer, buried under documents with no time to actually help the client in front of him. Mary started as a glorified recorder for client meetings. It's now a fact-extraction engine that litigation teams use to work through

Risky Business

Episodes

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