On The AI Floor, Shamil Malachiyev sits down with Jasmine Singh, General Counsel at Ironclad, for a hype-free look at what AI is really doing to legal work. Most people in legal either build these tools or buy them. She does both: she helps shape the platform, then runs her own company's contracts on it.
Before Ironclad she was a litigator in San Francisco big law, led global commercial at Pinterest, was Deputy GC at Patreon, and took her first GC seat at Binti. In this conversation she explains why she requires her team to use AI (and why she also tells them failure is acceptable), what she will never hand to an agent, and what junior lawyers should actually be learning now.
Expect to learn:
- Why she requires AI usage on her team, and why "failure is acceptable" is the other half of that rule
- What junior lawyers should learn now that AI does the first-pass redline
- Why there is no such thing as "right" legal advice in the abstract, only the best advice for the circumstance
- What happens when her AI agent negotiates against their AI agent, and when she just picks up the phone
- The duty of competence and the supervisory duty: what lawyers still legally have to review
- How Ironclad compressed intake to redline, and which agents actually run in production
- How to lead a team into AI: expectation plus enablement, not expectation alone
- The upside nobody talks about: why AI can make practising law less lonely
If you work in legal, lead a team through AI adoption, or you're early in a career that AI is reshaping, this one is worth the hour.
CHAPTERS
0:00 Promo
1:58 "A thousand lives as a lawyer": litigator, spin instructor, GC
4:45 Competitiveness, athletes, and knowing when to pull back
5:53 The industry sprint: who gives you permission to breathe
7:56 What's moving fastest in AI right now
9:26 In-house vs outside counsel: what AI changes, what it can't
14:06 What legal ops teams have to become
16:28 The new skill stack: law, business process, technology
17:41 The three groups of AI adopters
19:54 Her rule: AI usage is required, and failure is acceptable
21:16 Will AI replace lawyers? The duty of competence and supervision
23:48 There is no "right" legal advice in the abstract
24:28 Relationships, human emotion, and agent-vs-agent negotiation
26:57 Junior lawyers: what to learn when AI does the redline
29:24 The productivity treadmill: three hours instead of two days
32:27 Inside Ironclad: from contract acceleration to agents
36:49 Change management: why "why" beats "how"
38:40 What she's most excited about on the roadmap
40:33 Burnout: "I thought I had ruined my professional career"
46:13 Imposter syndrome, therapy, and deep-seated confidence
48:47 Building AI communities and a team learning syllabus
52:45 Her own daily AI stack
54:36 Em-dashes and looking "AI-ish"
55:17 Leading a team into AI: expectation plus enablement
58:12 Is there an AI bubble?
1:00:21 The upside nobody talks about: AI and loneliness
👇 CONNECT WITH JASMINE SINGH
Jasmine Singh ► https://www.linkedin.com/in/jasmine-singh-b4a25274/
Ironclad ► https://ironcladapp.com/
👇 CONNECT WITH SHAMIL
Shamil Malachiyev ► https://www.linkedin.com/in/shamilmalachiyev/
FluidLabs ► https://fluidlabs.com/
🎙 LISTEN to The AI Floor (The Founder's Code, Season 2)
Spotify ► https://open.spotify.com/show/7v6YOQ77R1xzbOiiHsDawd
Apple ► https://podcasts.apple.com/sa/podcast/the-founder-s-code/id1797768317
🔔 SUBSCRIBE for more unfiltered, ground-level conversations with the people actually building AI inside real companies.
ABOUT THIS CHANNEL
The AI Floor - honest, ground-level conversations that cut through the AI hype and count what's really happening with automation and AI agents across the industry. No shiny LinkedIn posts, just AI reality from the people doing the work.
#AI #LegalAI #LegalTech #Ironclad #GeneralCounsel #AIAgents #ContractAI #JasmineSingh #TheAIFloor #Podcast
