Marketplace Risk Platform Podcast

In this episode of Bulletproof Your Marketplace, Jeremy dives into the critical topic of marketplace taxation with Nick Furtwengler, senior tax manager at Miller Cooper. Nick brings over 14 years of experience in state and local tax law and has worked extensively with digital marketplaces. Listeners will gain insights into why tax compliance is essential for marketplaces of all sizes, including the risks of noncompliance, economic nexus rules, and how states leverage marketplaces to enforce tax collection. Nick highlights practical strategies for founders and leadership teams, such as tracking sales by state, understanding workforce and inventory obligations, and avoiding common pitfalls like misclassifying employees or contractors. The episode also explores accessible tools and software that help startups and growing marketplaces automate sales tax collection and reporting. Whether you’re a founder, operator, or legal counsel, this episode provides actionable guidance to help make your marketplace safer, stronger, and more sustainable.

In this episode of Bulletproof Your Marketplace, Jeremy Gottschalk dives into one of the most critical yet often misunderstood aspects of scaling digital platforms: insurance program and policy design. Joined by Garrett Johnston, Senior Vice President at Marsh with more than 25 years of experience in the commercial insurance industry, They explore how insurance can serve not just as a compliance requirement but as a strategic tool for managing risk, building user trust, and driving sustainable growth. Drawing on deep expertise working with major platforms like Uber, Lyft, and DoorDash, the conversation highlights how thoughtful insurance design can shape customer experience, regulatory relationships, and long-term scalability. Together, they unpack why partnering with brokers who truly understand the marketplace model is essential, the common pitfalls that lead to misaligned or overpriced coverage, and the core policies every startup should understand — including general liability, directors and officers (D&O), cyber, and errors and omissions (E&O). This episode offers a clear, actionable framework for founders, legal leaders, and trust and safety professionals seeking to balance innovation with protection and build marketplaces that are safer, stronger, and more resilient.

In this episode of Bulletproof Your Marketplace, Jeremy Gottschalk—author of the book and host of the podcast—sits down with Jimmy Toy, Chief Legal Officer at Articor Group, parent company of Redbubble and TeePublic. With platforms that receive tens of thousands of user-generated uploads every day, Jimmy brings his expertise in legal policy, governance, and trust & safety to tackle an unavoidable reality for marketplaces: incidents, threats, claims, and crises. Together, Jeremy and Jimmy explore why these challenges are not a matter of if but when, and how founders and leadership teams can prepare effectively. From building proactive response plans and managing insurance notifications to handling media inquiries with transparency and accountability, this conversation is packed with practical lessons. Whether you’re a founder, executive, or risk leader, this episode will help you anticipate problems, avoid costly missteps, and turn crises into opportunities to strengthen trust with your community.

In this episode of Bulletproof Your Marketplace, we explore one of the most pressing challenges facing digital platforms today: trust and safety. Joining us is Anna Pogreb, Senior Risk Strategist at EverC, who brings experience in compliance, risk, and marketplace operations. Together, we unpack how marketplaces have become a prime target for illicit activities—from counterfeit goods to money laundering and even more extreme cases—and why traditional, reactive approaches are no longer enough. Anna shares stories from the frontlines of risk management, insights into how bad actors exploit platforms, and practical strategies for building proactive trust and safety practices tailored to your marketplace. Whether you’re a founder, legal counsel, or risk leader, this conversation highlights why trust and safety must be a company-wide priority, how to break down silos, and how to design policies and processes that strengthen your marketplace against evolving threats. Stay tuned for actionable takeaways and inspiration to build a safer, more resilient platform.

In this episode of Bulletproof Your Marketplace Podcast, host Jeremy Gottschalk welcomes Jeff Sakasegawa, Trust and Safety Architect at Persona, who draws on over 15 years of experience for a deep dive into the chapter Creating Your Own Best Practices. The conversation explores why identity verification is foundational, why words and transparency matter in policy-making, and how strategic friction can strengthen—rather than hinder—user trust. Jeff highlights real-world examples and emphasizes the importance of cross-functional ownership in trust and safety programs. He also shares how platforms can develop strategies tailored to their unique business models instead of relying on one-size-fits-all policies. For founders and leadership teams, this episode delivers clear takeaways. Jeff leaves listeners with one actionable practice—link analysis—as a powerful tool to strengthen enforcement, connect signals across accounts, and outpace bad actors.