Lawyers have been reaching out to me about breaking into legal tech for years. Now engineers at some of the biggest tech companies in the world are looking at Harvey too, and I think that's the clearest signal yet that professional services became a hot space to be in, and that just wasn't true a few years ago. Katie Burke spent nearly twelve years at HubSpot before betting on Winston, Gabe and Harvey. She explains why Harvey doesn't want lawyers running from Big Law, what makes someone stand out in an interview, and why top engineers suddenly want to work in legal. And yes, someone still tweets that Harvey is going to zero every six months.

In this episode:

0:00 Zach’s Hot Disruptive Legal Take 4:22 Why Katie Burke Left HubSpot for Harvey 8:48 Betting on Winston and Gabe in Their 20s 11:39 The “Harvey Is Going to Zero” Tweet Cycle 12:54 Is There Actually a Moat in Legal AI? 15:23 Is Harvey Only for Big Law Juniors? 18:01 Can Harvey Compete With the Frontier Models? 20:55 Harvey’s Killer Feature May Be Its SLAs 22:37 Why Top Engineers Suddenly Want to Work in Legal 25:40 How Many Harvey Employees Are Lawyers? 27:34 Who Works Harder: Big Law or Harvey? 30:18 Does Working at Harvey Burn People Out? 32:30 The #1 Way to Stand Out in a Harvey Interview 36:18 Where Harvey Is Hiring Right Now 38:00 The HubSpot Playbook at Harvey 39:50 Should You Even Make a Three-Year Plan? 41:18 Dharmesh Shaw Called It in 2023 42:30 You Don’t Need to Write Code to Use AI 45:08 Where to Find Open Roles at Harvey

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Alex Su is one of those people I need to catch up with every now and then just to see what he's thinking. Since we recorded this, Alex was named President of Latitude Legal. He understands both the people selling lawyers on change and the lawyers they're trying to convince, and those two groups don't always see the same world. We get into Harvey, Legora and Claude, the billable hour, junior associates, where human judgment still matters, why trust may be part of Harvey's moat, and how both of us are using AI differently now than we were in 2023.

0:00 Zach's Hot Disruptive Legal Take 3:22 Harvey vs. Legora vs. Claude 5:58 Can Claude Gobble Up Harvey? 8:00 Why Haven't Junior Associates Been Replaced? 10:30 In-House Is Outpacing Law Firms on AI 12:49 Why Hasn't AI Killed the Billable Hour? 17:49 Why Hourly Rates Could Go Up 20:04 Is Anyone Less Busy Because of AI? 22:39 Where AI-Native Law Firms Could Win 24:28 If NDAs Are Never Litigated, Why Sign Them? 28:06 AI Made My Content More Human 31:11 How We Actually Use AI for Writing 38:28 How Many Lawyers Do You Need With AI? 40:22 When AI Gets Better, Trust Matters More 44:50 Has Harvey Built a Moat? 46:54 How Do You Compete With Harvey? 49:06 Is CLM Dead in the Water?

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Legora just acquired Wexler, and I think it's the clearest signal yet that AI in law is moving from transactional work to litigation. Gregory Mostyn, co-founder and CEO of Wexler, built the company just to the right of discovery. Not doc review, what happens when the documents actually hit the lawyers. He explains why he bet on facts instead of documents, why he stayed a scalpel while Harvey and Legora built Swiss Army knives, and why a company that wasn't for sale sold anyway. I also pushed him on the two questions I get from lawyers every week. Are we in a bubble? And if the models are this good, why buy anything at all instead of building it yourself? His answer to the second one is the part I'd replay. And yes, the company is named after Kim Wexler.

In this episode:

00:00 - Zach’s Hot Disruptive Legal Take 07:33 - Already Seeing the Benefits of Joining Legora 08:26 - Wexler Is Just to the Right of eDiscovery 10:44 - The Atomic Unit of Analysis Is Facts 13:12 - Building a “Case Brain” 15:02 - Scalpel vs. Swiss Army Knife 17:21 - AI for Litigators 21:08 - Are We in an AI Bubble? 24:24 - Product Advice from an Old-School Judge 26:53 - Why Security and Accuracy Are More Important than Speed 28:59 - The Main User of Wexler Is the Wexler Agent 30:55 - Can You Run AI Live in a Deposition? 33:57 - Can Lawyers Build This Themselves? 38:46 - Story behind Legora’s Acquisition 43:50 - Getting in the Room Is the Hard Part 46:01 - Will AI Kill Relativity? 46:58 - Inspired by Kim Wexler from Better Call Saul

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Follow Gregory https://uk.linkedin.com/in/gregory-mostyn-9b3a89b8

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