Risk, Calibration, and 5,000 Bad Haircut Lawsuits with David Schellhase, 3x GC and Okta Board Member

David Schellhase has been general counsel at three public companies - Salesforce, Groupon, and Slack - and he's learned that great in-house lawyering is less about knowing every law and more about knowing your company's risk appetite cold. In this episode of CZ and Friends, David joins Cecilia to share what three decades in Silicon Valley taught him about risk, prioritization, and when to push back on your CEO.David and Cecilia cover:Why the best in-house lawyers "always be calibrating," reading their company's risk profile the way a trader reads the market, and adjusting advice accordingly.How technology has made lawyers more available than ever, and why that's a problem worth solving.What it was like to be GC at Slack through explosive global growth, and how Stewart Butterfield's obsession with craft shaped David's own approach to legal work.Why David told his CEO, who called from Dublin at midnight, having read the actual GDPR text, that he hadn't read it yet and wouldn't for six months, and why that was the right call.How Groupon ended up with 5,000 lawsuits in Brazil over bad haircuts, and what that taught him about scaling globally without a legal map.Why happy hours are technically criminal in New York (it involves liquor pricing law and a rat-encrusted menu).His thesis that innovation is crime, and why the best in-house lawyers have to believe in their product enough to push the law forward.What "strong opinions, loosely held" and "disagree and commit" look like in practice as a GC.Why he thinks in-house lawyers should seek out productive narcissists, and what makes that combination so powerful in a founder.David now sits on the board at Okta, co-teaches Ethical Issues in Global Technology Product Design at Stanford, and is Entrepreneur in Residence at Ballistic Ventures.Follow David: @David Schellhase on LinkedInChapters: 00:00 Preview 00:12 Welcome and intro: David Schellhase, Okta board member and EIR at Ballistic Ventures 00:25 What David is working on today 02:53 How technology has increased stress in the legal profession 06:52 Always be calibrating: understanding your company's risk appetite 11:12 The difference between in-house and BigLaw prioritization 14:30 Slack, Stewart Butterfield, and the midnight GDPR call 20:45 Innovation is crime: Uber, Airbnb, and the Overton window 25:57 Groupon: happy hours are criminal in New York 30:05 Groupon: 5,000 bad haircut lawsuits in Brazil 34:19 Strong opinions, loosely held, and disagree and commit 43:24 AI: underhyped, and why labeling AI content matters 50:11 Why in-house lawyers should work for productive narcissists 52:43 Lightning round: myths, books, and advice for your younger selfFollow us on all social platforms to get each new episode when it drops.⁠@Cecilia Ziniti⁠ on LinkedIn⁠@CeciliaZin⁠ on Twitter/X⁠@GC AI⁠ on LinkedIn@gcai on X⁠gc.ai⁠ website