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.

Measuring the impact of trust & safety initiatives is more and more crucial to securing funding and demonstrating value for them. But how do you go about that? And, what happens when you are unsuccessful? Often, it takes a toll on professionals' mental health, which is already adversely impacted by the day-to-day responsibilities that come with the territory. On this episode, trust & safety product guru Heather Grunkemeier joins to talk about her advice for developing metrics for trust & safety initiatives while looking out for your mental health.

In this episode, we sit down with Kristin Kupiec, Associate Manager of Community Response at DoorDash, to explore the intricate dynamics between platforms and law enforcement. This conversation dives deep into the proactive and reactive measures platforms can take when interacting with law enforcement agencies. Kristin shares her extensive experience and offers practical advice on how can effectively manage these critical relationships.

Once merely an afterthought, trust & safety has quickly evolved from a peripheral function to become one of the most critical and central functions in technology today - and for good reason. The trust & safety discipline has assumed the responsibility of keeping the internet safe, and trust & safety professionals are on the front line of this seemingly insurmountable task. On this episode, Sujata Mukherjee, Head of Global Research for Trust & Safety at Google, discusses the evolution of trust & safety as a function, discipline, profession, industry and ecosystem. She also talks about how trust & safety's importance fits into a platforms growth strategy and more!

AI's Impact on Fraud by Marketplace Risk

For marketplace startups and early-stage tech platforms, lawyers can often seem out of reach due to resource constraints. But, there are significant risks when developing your product that good counsel can help you avoid - and the results will save you exponentially down the road. Join Alex Kroeger in this episode of the Platform Podcast as she discusses how platforms can successfully leverage product counsel as they grow!

All too often platforms focus on VC investment to drive hyper-growth, which usually leads to bloated organizations (and in recent times, layoffs). But what if platforms focused on running a lean organization, with more utility players who could function as 'jacks-and-jills-of-all-trades?' The result would create a solid foundation that enables growth, but also stability and flexibility. In this episode, Clutch VP of Marketplace Strategy Ryan Stevens talks about bootstrapping a company to growth, while achieving great metrics and a culture based on lean principles.

Artificial intelligence seems to be pervading every aspect of our lives - it certainly consumes social media and news feeds. And while AI certainly has many benefits, it also brings some challenges - especially when leveraged as a content moderation tool. The question becomes - what will be the role of humans? In this episode, Camilla Hegarty discusses the evolution of content moderation, the role of AI, and the need for humans in the content moderation function.

Everyone is at risk of having their information compromised - especially in a world where data is so valuable. If you are a tech company, such a compromise could devastate your business. But there are easy ways to mitigate your cyber risk and protect your company with offensive cybersecurity and some common sense. Listen to this episode to hear about both from Azacus.io Co-Founder Nicola Gandy.

California's new high-volume marketplace seller bill. Illinois' junk fee bill (and any other federal action / states with junk fee bills as they impact platforms) Privacy legislation (federal and the 15 states and the ones that are going into force soon) AI legislation (UT and any others) 1099K threshold Age verification regulations

In order for a platform to succeed, it must have integrity. But what does this mean in practice? In the case of Wolt, it's a cross-functional, holistic focus on the entire community they serve from the entire team. This includes offering courier partners more chances to earn, helping merchants to grow and thrive with more customers, and providing a diverse selection of goods for consumers that brings joy and simplicity to people’s lives. Listen now to learn more about how Wolt puts integrity into action.