Akshay Verma, COO of SpotDraft explores his non-linear journey through the legal industry. From his early days as a big-law paralegal to lawyer to a business development role to leading legal operations at tech leaders like Facebook and Coinbase, Akshay shares his unique perspective on why the most successful legal departments prioritize process over technology.

The conversation dives deep into the realities of Contract Lifecycle Management (CLM), the evolution of the "agentic" legal tool, and why change management is the biggest hurdle for legal innovation. Akshay also discusses the "underdog mentality" that drew him to the startup world and the future of AI in legal workflows.

Key Takeaways:

• Process First: Technology is not a "magic pill" for broken workflows; centralized repositories and defined approval chains must come first.

• The Power of BD: Business development skills (evangelism and resilience) are critical for successful legal operations leaders.

• The "Holy Trifecta" of Legal Tech: Every department needs a CLM, a Spend Management tool (at scale), and an agentic Workflow/Intake tool.

• AI vs. Lawyering: AI will replace non-legal tasks, not the lawyers themselves, making AI literacy a new standard for the profession.

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

Sophia Contreras Schwartz, General Counsel at Nextdoor, discusses her unique journey of building a legal department from the ground up. Sophia discusses how her background as a musician and fitness instructor informs her collaborative leadership style and why Nextdoor identifies as "Middle Tech"—a category of companies often overlooked by one-size-fits-all regulations.

The conversation explores the strategic value of hiring Legal Operations early, the specific tech stack that keeps a lean team of eight efficient, and why "versatility and curiosity" are the most important traits for in-house counsel today.

Key Takeaways:

• The First Legal Hire: Companies should consider their first GC when they start generating significant revenue or enter highly regulated spaces.

• "Middle Tech" Challenges: Nextdoor faces unique regulatory hurdles, like age verification laws, which are often designed for "Big Tech" giants but create significant operational burdens for mid-sized platforms.

• Force Multipliers: Investing in Legal Ops early allows a small team to scale by focusing on process design and vendor management rather than just manual intake.

• AI as a Strategist: Using tools like GC.AI doesn't just speed up drafting; it helps in-house lawyers ask better questions of their outside counsel by identifying nuances that general AI might miss.

• Legal Tech Tools: Ironclad, SimpleLegal, GC.AI

• Organization: Chamber Music America

Lucas Moskowitz, General Counsel at Robinhood returns to the show to talk tokenization of Real World Assets and the current state of crypto legislation.

Lucas updates us on Robinhood's evolving demographics, noting that while the platform remains a hub for first-time investors, the customer base is maturing alongside the platform's product offerings, such as retirement matching and advisory services. Moskowitz also highlights the company's commitment to financial literacy.

The core of the conversation shifts to the shifting regulatory landscape regarding cryptocurrency and the potential for legislative clarity under a new administration. Moskowitz breaks down the concept of Tokenization of Real World Assets (RWA), explaining how blockchain technology can democratize access to private markets, art, and real estate.

The discussion covers the technical and legal differences between "native" tokens and "wrapper" products, the benefits of 24/7 liquidity, and why the United States risks falling behind global jurisdictions like the EU and Asia if regulatory frameworks do not evolve.

• Robinhood's Evolution: The platform now serves 26 million customers. While half are first-time investors, the company is expanding into advisory and retirement products to serve users throughout their financial lifecycles.

• Crypto Regulation: There is a shift from "regulation by enforcement" toward legislative clarity. Moskowitz discusses the importance of comprehensive market structure bills and stablecoin legislation to provide long-term durability for the industry.

• Tokenization Mechanics: Tokenization is the digital representation of a real-world asset on a blockchain. This innovation promises to increase liquidity, allow for fractional ownership of high-value assets (like private equity or art), and enable faster settlement times.

• The "Wrapper" Concept: Moskowitz explains Robinhood's EU offering, where customers trade a tokenized "wrapper" that represents a share of US stock held in custody, distinguishing this from companies issuing native tokens directly on the blockchain.

• Why Lawyers Should Care: Even those outside of securities law must pay attention to tokenization, as it is poised to impact the documentation and transfer of all real-world assets, including real estate deeds and commercial contracts.

• Robinhood RWA Policy Paper: Read the policy papers mentioned in the episode regarding Tokenization.

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI