
Technically Legal - A Legal Technology and Innovation Podcast
Technically Legal is a legal tech podcast exploring how technology is transforming the legal landscape. Each episode features insightful interviews with legal innovators, tech pioneers, and forward-thinking educators who are leading this change.
Our guests share their experiences and insights on how technology is reshaping legal operations, revolutionizing law firm practice, and driving the growth of innovative legal tech companies. We also explore the broader implication of technology on everyone involved in the legal system, from practitioners to clients.
The podcast is hosted by Chad Main, an attorney and founder of Percipient, a tech-enabled legal services provider. Chad launched Percipient on the belief that when technology is leveraged correctly, it makes legal teams more effective.
Technically Legal Podcast is an ABA Web 100 Best Law Podcasts Honoree.
Latest episodes

Jan 30, 2025 • 32min
From Tractors to Timekeeping: Jack Weinberger’s (CEO Ajax) Legal Tech Journey
Jack Weinberger, co-founder of Ajax and a former finance and private equity professional, shares his transition into legal tech. He recounts his journey from banking to entrepreneurship, driven by insights into lawyers' challenges. Highlighting Ajax's innovative AI timekeeping technology, he emphasizes data security and efficiency. Jack discusses the importance of understanding lawyer workflows and hints at exciting features like capturing spontaneous conversations, showcasing how legal tech can transform daily practices for lawyers.

Jan 16, 2025 • 27min
From Athlete to AI: Summize CEO's Legal Tech Entrepreneurial Journey (Tom Dunlop)
This episode features Tom Dunlop, founder of Summize, a contract lifecycle management (CLM) platform. Tom discusses his unique path to founding Summize, from his background as a professional athlete and lawyer to his passion for solving real-world problems with technology. Key takeaways: The genesis of Summize: Tom explains how his experience reviewing hundreds of contracts manually led to the idea for Summize. Early challenges and the evolution of AI: Tom describes the initial challenges of summarizing contracts using AI in 2018 and how the advent of generative AI has revolutionized Summize's capabilities. Summize's unique approach: Summize differentiates itself by embedding its functionality within popular workplace tools like Slack, Teams, and Microsoft Word, allowing users to manage contracts without leaving their familiar workflows. How Summize works: Tom explains how Summize uses AI to curate contract data and provide summaries that are relevant and tailored to specific business needs. The future of Summize: Tom shares his vision for the future of Summize, including plans to further leverage AI, enhance native integrations, and incorporate validated content from the legal community. Resources and Links: Summize Website: summize.com Connect with Tom on LinkedIn Keywords: legal tech, contract lifecycle management (CLM), AI, generative AI, contract summarization, legal technology, Summize, Tom Dunlop, Microsoft Word, Slack, Teams, Outlook, DocuSign

Jan 9, 2025 • 36min
Connecting Main Street to Wall Street: How Data Driven Financial Regulation and Emerging Tech Like Crypto Can Help Bridge the Gap (Lucas Moskowitz - GC, Robinhood) (Replay)
Lucas Moskowitz, General Counsel at Robinhood, sheds light on the company's mission to democratize finance, making investing accessible to all. He discusses his intriguing career transition from big law and the SEC to shaping digital finance at Robinhood. The conversation dives into the importance of data-driven regulation, balancing investor protection with innovation. Additionally, Moskowitz explores the potential of crypto and blockchain technologies, emphasizing the need for education in legal circles to navigate these emerging fields.

22 snips
Dec 18, 2024 • 28min
Best of 2024: Can AltFee Kill the Billable Hour and Bring Transparency to Legal Billing? (Scott & Digby Leigh)
Scott and Digby Lee, co-founders of AltFee, revolutionize the legal billing landscape with their innovative app designed to replace the billable hour. They delve into the significance of alternative fee arrangements (AFAs), emphasizing the shift towards value-based pricing, especially in the age of AI. Their discussion touches on enhancing client relationships through transparency, the impact of COVID-19 on legal practices, and the integration of technology to streamline billing processes. A must-listen for anyone interested in the future of legal pricing!

Dec 11, 2024 • 43min
Best of 2024: Investing in Legal Tech and the Ingredients of a Successful Start-Up (Zach Posner, The LegalTech Fund)
What does it take to build a successful legal tech startup? In this Best of 2024 episode, we revisit our conversation with Zach Posner, co-founder of the LegalTech Fund, an investment fund focused on supporting innovative legal technology companies. Zach’s unique perspective on legal tech investing is rooted in his broad experience, including building an education tech company acquired by McGraw Hill. During our conversation, he shares valuable insights into what makes startups thrive. From the importance of transparent investor updates to fostering frequent, meaningful customer interactions that guide product development. We also explore the LegalTech Fund’s investment focus: Tools leveraging contracting data for business insights Tech solutions expanding access to legal services Whether you’re an entrepreneur, an investor, or simply interested in the evolution of legal tech, this episode is full of practical advice and inspiring insights. Episode Credits Editing and Production: Grant Blackstock Theme Music: Home Base (Instrumental Version) by TA2MI Want to keep up to date about new episodes? Technically Legal Update List. Want to learn more about Percipient (percipient.co)? Follow Chad on Linkedin: Chad Main | LinkedIn Follow the podcast on LinkedIn: Technically Legal | LinkedIn Follow the podcast on Instagram: Technically Legal | Instagram Follow the podcast on X: Technically Legal | X

15 snips
Dec 4, 2024 • 49min
Best of 2024: Using Agile Project Management to Streamline Legal Workflows (John Grant, The Agile Attorney)
John Grant, a lawyer and founder of The Agile Attorney consultancy, shares his innovative approach to legal project management. He advocates for Agile and Kanban methodologies to transform legal workflows, emphasizing flexibility and efficiency. Grant explains how traditional methods can hinder progress and highlights the power of Kanban boards in visualizing tasks. He also reflects on his unique journey from tech to law, discussing how blending legal expertise with technology enhances client satisfaction and optimizes team performance.

Nov 20, 2024 • 37min
Beyond Billable Hours: Flatiron's Conrad Everhard on a Fixed-Fee and Tech Based Approach to M&A
Conrad Everhart, founder of Flatiron Law Group, shares his journey from Georgetown grad to partner at major law firms like Jones Day. He left BigLaw to offer a cost-effective, tech-driven model for M&A services. The firm utilizes flat fees, low overhead, and custom software like Deal Driver to enhance client insights. Conrad also discusses his work with Stanford’s Codex project, where he's developing an AI negotiation simulator to train future lawyers, emphasizing the crucial blend of AI and human judgment in legal negotiations.

Nov 6, 2024 • 33min
An Inside Look at How Atlassian Uses Its Own Tools to Power Legal Workflows and Encourages Thoughtful Adoption of AI (Stan Shepard, General Counsel)
Stan Shepard, General Counsel of Atlassian, offers an engaging look into his career journey from finance journalist to legal leader at a major tech company. He reveals how Atlassian's legal team leverages internal tools like Jira and Confluence to enhance collaboration and streamline workflows. The conversation highlights the role of AI in automating legal requests and improving efficiency. Shepard also shares valuable advice on adopting AI responsibly within legal departments, emphasizing cultural shifts towards modern communication practices.

Oct 23, 2024 • 32min
100-Day Dispute Resolution: New Era ADR is Changing the Game (Rich Lee, CEO)
Rich Lee, CEO of New Era ADR, discusses his company's mission to revolutionize dispute resolution with a tech-driven platform. He highlights the remarkable 100-day model that drastically cuts resolution time, promoting efficiency and lower costs. Lee also addresses challenges in the legal field regarding technology adoption and the importance of social proof in driving innovation. The podcast explores the recruitment of skilled neutrals, balancing expertise with assertiveness, and the transformative impacts of AI on online dispute resolution.

Oct 9, 2024 • 33min
Transforming Mobile Device Forensics: A Conversation with ModeOne CEO Matthew Rasmussen
This episode features Matthew Rasmussen, Founder and CEO of ModeOne, which is an app that provides targeted smart phone data discovery. Matt discusses his journey from a psych major waiting tables to landing a job in eDiscovery in its earliest days-- a job that ultimately helped him land jobs in BigLaw for multiple firms running their litigation technology departments. It was when he was working for O’Melveny & Meyers when he had his "light bulb moment" that led to the creation of ModeOne, a solution addressing the challenges of efficient data collection from mobile devices. Matt explains how ModeOne works, its benefits over traditional digital forensic collection methods, and how it addresses concerns about evidentiary defensibility. He also highlights the various use cases for ModeOne beyond litigation, including internal investigations, HR matters, and compliance. The conversation delves into ModeOne's development, its unique approach compared to competitors, and its future roadmap, including internationalization and integrations with other platforms like Relativity. Learn more about Matt. Key Discussion Points: [0:39] Matt's unconventional path to eDiscovery [3:35] The "light bulb moment" that sparked the idea for Mode One [9:02] How Mode One works and its advantages [11:36] Addressing evidentiary concerns and gaining credibility [19:19] Expanding use cases beyond litigation [22:48] iOS and Android certification process [23:31] Apps and data supported by Mode One [25:18] Mode One's built-in review tool and Relativity integration [28:04] Future roadmap and upcoming features