Version Up
Claim This Podcastby Kaj Rozga
Podcast Overview
<p>One lawyer’s journey to transform his legal practice. </p> <p>Version Up (<a href="https://versionup.ai" target="_blank" rel="noreferrer noopener">versionup.ai</a>) is a podcast about deploying AI and technology in legal practice. Host Kaj Rozga — a practicing lawyer leading innovation inside a legal team at a Global 500 — talks with the practitioners, founders, and operators doing the heavy-duty work of repurposing the practice and business of law for the AI era.</p> <p>Each episode is a practical conversation about what’s working, what isn’t, and what’s worth paying attention to. The goal is to work towards clarity through an honest dialogue about building and deploying legal technology at law firms and corporate legal departments.</p> <p>For lawyers, innovation leaders, legal ops professionals, founders and investors who want the bottom-line on the state of play in legal tech.</p> <p>| Hosted by Kaj Rozga | Music by Brett Ryback | views my own |</p>
Language
🇺🇲
Publishing Since
3/28/2025
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Recent Episodes
June 17, 2026
From BigLaw to Solo Practice: Demystifying What it Means to Launch an AI-Native Law Firm
Dan Sito, former federal tax partner and AI innovation partner at Perkins Coie, joins VersionUp to discuss why he left Big Law to launch Sito PC, an AI-native law firm. Our conversation reveals that going "AI-native" does not mean building a tech company, chasing high-volume/low-value work, or rebuilding a practice from scratch — it means a specialist lawyer using agentic tools to deliver premium work on his own terms. The conversation covers how democratized access to agent harnesses like Claude Code and Codex has erased much of the resource advantage that kept top performers inside large firms, and why enterprise legal AI platforms (Harvey, Legora, Microsoft Copilot) solve for scale that a solo practitioner simply doesn't need. Sito explains how AI powers his legal practice and maps his work — client intake, legal research, drafting, risk allocation — into stages where agents add leverage while the lawyer keeps judgment and verification. He also addresses the questions every lawyer thinking about going solo is asking: competitive advantage versus Big Law, the risk of clients insourcing AI, law firm pricing and whether AI-native means cheaper (he argues for expanding value, not just cutting cost), and business development as a solo. On the tech stack, Sito details running a local open model to keep confidential client data under his own control — converting confidential information to generalized inputs for frontier models — and why data autonomy and subscription pricing matter for a bootstrapped practice. A level-headed, practitioner's view of how AI changes the practice and business of law without disruption mythology. At a time of AI-induced anxiety and fear in the profession, I think lawyers practicing at law firms will find Dan’s experience inspiring and hopeful. In-house lawyers practicing at corporate legal departments will find comfort and familiarity with the transition that Dan’s practice offers when compared to AI-native law firm start-ups, legaltech vendors, and general purpose LLM solutions claiming to be able to fulfill their legal needs. Most importantly, Dan’s experience shows that lawyers are not predestined to be victims to AI disruption to the legal market. They are actors can choose to act. Individually, boot-strapped, and without having to restart their legal practice from scratch. https://www.linkedin.com/in/daniel-sito/ https://www.linkedin.com/company/sito-pc/ https://sitopc.com/
June 8, 2026
Commitment Over Curiosity: The Real Drivers of AI Transformation at Law Firms
Abhijat (Ab) Saraswat comes on the podcast to address *the* question that is on the minds of law firm innovation leaders: what makes AI transformation stick? On the surface, it looks like everything is going great. Training sessions, positive usage stats, vibe-coded POCs, vendor demos and pilots, some nice publicity on LinkedIn and at conferences. A law firm going AI-native. But underneath the surface progress is stalling. Cultural constraints, capacity limitations, technical debt, ineffective governance -- hidden icebergs are causing the AI transformation to stall out. Ab says that it all comes down to institutional commitment and use case clarity. It’s a helpful framing that focuses a legal enterprise on the key drivers for whether a law firm is able to deploy AI effectively. These drivers cut across a lot of dimensions: leadership style, organizational structure, build vs. buy, LLM and vendor-agnositic solutions, and building for an agentic enterprise are all part of the formula. These are the things that position legal teams for the future without having to make a “bet” on a constantly changing state of art. It was refreshing to see the conversation go in some directions that I did not expect. Ab is *not* an advocate for the average law firm building the tech stack needed to developing their own bespoke tools. As he sees it, third party solutions are good enough and the added cost of making them great may not be worth it to most legal enterprises. Besides, building out the “middleware” of an AI tech stack that protects a law firm’s “secret sauce” is less about technical architecture and more about achieving the connectivity to tap into enterprise date and practice intelligence. My sit down with Ab was a badly needed sanity check at a moment when things feel extremely fluid in the industry. I’m grateful for him coming on to share his perspective as a legal tech strategist (lupl.com) and thought leader (fringelegal.com). LinkedIn
May 13, 2026
The Digital Brain and the Future of Legal Knowledge
Jamie Tso and Raymond Sun join for a check-in on Legal Quants, their growing community of elite AI-native lawyers who design and deploy AI in their legal practice. A previous episode covered the origin story. This one ends up mostly being about LQ Brain — their adaptation of the "digital brain" concept, applied not to an individual's knowledge but to the collective intelligence of their entire community. The problem they were solving is simple: 700 to 2,000 WhatsApp messages a week, across a global network of highly technical lawyers, with no good way to preserve what gets figured out. A weekly digest helped but had time decay — you read it and toss it, like a newspaper. LQ Brain is the timeless layer on top: a structured knowledge graph built by running agent teams across 12,000 messages, synthesizing them into atomic notes, debates, and insights, cross-linked across eight core themes. It lives in Obsidian, was compiled using Claude Code, and is deployed on their website behind a member password. The conversation is a useful primer on why this approach is different from RAG. The key isn't the retrieval mechanism — it's the compilation step that happens first. When a member queries LQ Brain, they're not searching raw chat exports; they're querying insights that have already been distilled, organized, and interlinked. It works like a reasoning harness: because the notes encode the community's actual debates and disagreements, answers come back with nuance and personality. Several members have said it feels like asking a fellow legal quant. Jamie and Ray also use it internally when thinking through LegalQuants' roadmap — rather than polling the community, he asks the brain how the community would think. Placing Digital Brains in the wider arc of AI, having a second brain is a moat right now, but like agentic coding before it, it will become table stakes fast. The more interesting question is what the playing field looks like once everyone has one. And the second brain is only as good as what feeds it, and the hard problem isn't the technology — it's deciding what context gets captured at all. Calls, meetings, hallway conversations. How much do you record? Who consents? What does systematic capture do to workplace culture? It raises boardroom-level risk questions that are only starting to get asked. Talking to Jamie and Ray tends to feel like seeing around a corner, and this episode is no exception. legalquants.com | Jamie Tso on LinkedIn | Raymond Sun on LinkedIn
30 total episodes available
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- What is Version Up?
<p>One lawyer’s journey to transform his legal practice. </p> <p>Version Up (<a href="https://versionup.ai" target="_blank" rel="noreferrer noopener">versionup.ai</a>) is a podcast about deploying AI and technology in legal practice. Host Kaj Rozga — a practicing lawyer leading innovation inside a legal team at a Global 500 — talks with the practitioners, founders, and operators doing the heavy-duty work of repurposing the practice and business of law for the AI era.</p> <p>Each episode is a practical conversation about what’s working, what isn’t, and what’s worth paying attention to. The goal is to work towards clarity through an honest dialogue about building and deploying legal technology at law firms and corporate legal departments.</p> <p>For lawyers, innovation leaders, legal ops professionals, founders and investors who want the bottom-line on the state of play in legal tech.</p> <p>| Hosted by Kaj Rozga | Music by Brett Ryback | views my own |</p> - How often does this podcast release new episodes?
This podcast updates daily.
- Where can I listen to this podcast?
This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
- Does this podcast accept guests?
No, this podcast does not typically feature guests.
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