Ted sits down with Rob Saccone, CTO at Lega, to discuss the lessons of past legal innovation efforts and the future of law firm business models. From the failures of Clearspire and Atrium to the pressures AI is placing on the billable hour, Rob shares his expertise in legal technology, client-focused service design, and investment strategy. With insights on why “the voice of the client always wins,” this conversation gives law professionals a candid look at how to adapt and thrive in a changing market.

Ted sits down with David McCarville, Director at Fennemore Craig, P.C., to discuss how AI, R&D, and alternative business models are reshaping the legal industry. From implementing alternative fee arrangements to creating playbooks that train the next generation of attorneys, David shares his expertise in innovation, governance, and client-focused solutions. With insights on balancing work-life culture while driving technological change, this conversation offers law professionals a practical look at the future of legal services.

Ted sits down with Lev Loukhton, Legal Tech Investor at GrayHair Venture Partners, to discuss how AI and digital transformation are reshaping the legal profession. From automating due diligence to challenging the partnership model, Lev shares his expertise in corporate law, innovation, and investing in legal technology. With insights on cultural resistance, client-driven demands, and the rise of AI-native firms, this conversation helps law professionals understand the shifts redefining the future of legal services.

Ted sits down with Ben Chiriboga, Chief Growth Officer at Nexl, to discuss how storytelling, business thinking, and technology are reshaping the legal profession. From his journey from practicing law to leading in legal tech, to the rise of AI and agentic workflows, Ben shares his expertise in growth strategy, innovation, and career development. With insights on why law is in a “time between worlds,” this conversation challenges legal professionals to rethink how they adapt, lead, and grow in the future of law.

Ted sits down with Patrick DiDomenico and Kevin Klein, Co-Founders of Legal Tech Connect, to discuss the evolution of legal technology, innovation, and the launch of their new Innovators and Investors event. From building the KM&I Conference to bridging the gap between law firms, vendors, and investors, Patrick and Kevin share their expertise in community building, knowledge management, and legal tech strategy. With candid insights on AI hype, shifting market dynamics, and the power of collaboration, this conversation gives law professionals a clear view of where legal innovation is headed.

Ted sits down with Usman Sheikh, Managing Director at High Output Ventures, to discuss how technology, AI, and market pressures are reshaping professional services and law firms. From the collapse of information arbitrage to the limitations of the partnership model, Usman shares his expertise in entrepreneurship, consulting, and building scalable businesses. With insights on consolidation, new business models, and the future of knowledge work, this conversation offers law professionals a clear view of the challenges and opportunities ahead.

Ted sits down with Ray Sun, Tech Lawyer at Herbert Smith Freehills Kramer, to discuss the global landscape of AI regulation and its impact on the future of law. From building the Global AI Regulation Tracker to unpacking the contrasting AI policies of China and the U.S., Ray shares his expertise in technology law and policy. With insights on how AI regulation is becoming a geopolitical battleground, this conversation helps law professionals understand the opportunities and risks shaping legal practice in an AI-driven world.

Ted sits down with Sarah Thompson, Chief Product Officer at BlueStar, to discuss how AI and M365 are transforming legal investigations and eDiscovery. From solving the modern attachment problem to integrating subject matter expertise into AI workflows, Sarah shares her expertise in building custom, defensible solutions for complex legal data challenges. With insights on accelerating case resolution and preparing for AI’s impact on legal roles, this conversation gives law professionals practical strategies to stay ahead in a rapidly evolving field.

Ted sits down with Gordon Crenshaw, Partner at The LegalTech Fund, to discuss the future of legal services, Law Firm 2.0, and the market forces reshaping the industry. From the challenges of innovation in traditional law firms to the role of AI, private capital, and consolidation, Gordon shares his expertise in legal tech investment and market strategy. With insights on what makes startups succeed and how technology is redefining legal infrastructure, this conversation gives law professionals a clear view of the opportunities and risks ahead.

Ted sits down with Kara Peterson, Co-founder at Descrybe.ai, to discuss the future of legal research, open-source legal data, and the role of AI in democratizing access to the law. From the challenges of building usable tools to the need for independent benchmarking, Kara shares her expertise in legal tech strategy, marketing, and innovation. With insights on navigating underserved markets and cutting through the AI hype, this conversation offers legal professionals a grounded look at what it really takes to build impactful, trustworthy legal tech.