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.

In this episode of Bulletproof Your Marketplace, Jeremy Gottschalk sits down with seasoned legal counsel Krishan Thakker to unpack how user contracts and robust privacy practices can act as liability shields for digital platforms.

Drawing on over 15 years advising global technology, e-commerce, and social media companies, Krish shares his expertise at the intersection of data privacy, regulatory compliance, AI governance, and trust & safety.

Together, they explore why privacy can no longer be an afterthought, the dangers of conflating terms of use with privacy policies, and the financial and reputational fallout from neglecting compliance—illustrated through high-profile failure.

Krish also outlines practical steps for platform operators, including conducting a data audit, adopting a “less is more” approach to PII collection, and drafting clear, standalone user agreements.

Whether you’re a founder, legal counsel, or trust & safety leader, this episode delivers actionable strategies to protect your platform, build user trust, and stay ahead of evolving regulations.

In this episode of Bulletproof Your Marketplace, Jeremy sits down with attorney Krishan Thakker to explore the critical role of Terms of Use as liability shields. With over 15 years of experience advising companies like Wish, Match Group, and Meta, Krishan explains why these agreements are far more than legal formalities: they are a platform’s first line of defense and, when crafted carefully, can prevent costly disputes while safeguarding business integrity. The conversation highlights common mistakes founders make, from borrowing irrelevant terms to neglecting user assent, and underscores the risks of misalignment between marketing promises and contractual language. Through practical insights and real-world examples, this episode shows why Terms of Use must be treated as a living strategy rather than boilerplate text, offering founders, legal counsel, and trust and safety leaders the tools they need to strengthen their marketplace’s foundation and scale with confidence in an increasingly complex legal environment.

In this episode of the Marketplace Risk Platforms Podcast x Bulletproof Your Marketplace, Jeremy is joined by risk and regulatory compliance expert Yee Carter to unpack the importance — and potential future — of CDA Section 230 protections for online platforms. Drawing from her experience at Google, X, and in government, Yee explains how Section 230 has enabled marketplace innovation by shielding platforms from liability for user-generated content, while highlighting that these protections are not absolute.

The discussion explores real-world cases — including Amazon’s solar eclipse glasses controversy and recent litigation involving TikTok and AI platforms — to illustrate where Section 230 protections have succeeded and where they’ve been challenged. Yee and Jeremy also dive into emerging gray areas such as algorithmic recommendations, AI-generated content, and evolving bipartisan scrutiny that could reshape the law.

Listeners will gain practical insights into how marketplaces can navigate compliance, mitigate risk, and prepare for a shifting legal landscape, particularly as AI becomes more deeply integrated into platform operations.

In the latest episode of the Platform Podcast, Alexios Mantzarlis, Director of the newly created Security, Trust and Safety Initiative at Cornell Tech (SETS) discusses his motivation for joining Cornell Tech to build a program that bridges the technical knowledge gap in the field of trust and safety. The initiative aims to reduce online harms through innovative clinics and to engage deeply with practitioners and decision-makers in digital safety. Alexios also shares his background in trust and safety, including his significant contributions at Google and his role in the International Fact-Checking Network. Don't miss this insightful conversation on the future of trust and safety in the digital age.

In this episode of the Platform Podcast, Cotera Founder Ibby Syed and Paige Zachs, Head of Operations and Customer at Coterie, explore the intersection of AI and customer experience (CX) in trust & safety. They discuss how CX leaders are leveraging AI-powered tools to enhance customer safety, manage brand risks, and streamline workflows - emphasizing the critical role of CX leaders acting as the "CEO of the customer." The discussion also covers potential pitfalls of mismanaged AI and the importance of robust processes and real-time analytics in safeguarding brand reputation. You'll get insights into the future of AI in CX and advice for leaders navigating this evolving landscape.