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.
9 Oct 2025TRANSCRIPT
Managing Risk — Insurance Policies and Program Design
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.
25 Sept 2025TRANSCRIPT
Managing (the Inevitable) Incidents, Threats, Claims, and Crises
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.
Inside a recent episode
Marketplace Taxation Compliance — An Overview
Published 16 Oct 2025 · Transcript excerpt
[…] But keep in mind, if you're expanding your workforce beyond the states in which you're based, you're going to have tax obligations in those states. So it's important to know that just so that you're not caught off guard where you're what we call your state tax footprint is located. Right. And so in today's kind of tech, well, I guess it's pretty much many industries. But with tech companies and so many of them being remote or remote first companies, I could imagine that that conundrum has exploded since COVID and companies finding out that they have tax obligations or reporting obligations in every state where they've got remote employees. […]
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