Some states make sales tax filing straightforward — and then there are the ones that keep even seasoned pros on their toes.

In this episode of Beyond Death & Taxes, Matt and Clay dig into one of Avalara’s most downloaded webinars: the 10 trickiest states for sales tax returns. From inconsistent deadlines to confusing location reporting and “alphabet soup” schedules, they walk through the quirks and complexities that make filing in certain states uniquely challenging.

You’ll hear expert insights from Avalara’s tax pros as they break down what makes states like California, Colorado, Illinois, New York, Louisiana, Texas, and more so difficult — and what finance teams should be watching out for as rules, thresholds, and interpretations continue to shift.

And before diving in, the hosts pay their respects in the Compliance Graveyard to one of the most persistent myths in the industry: the idea that all states handle sales tax the same way. (Spoiler: they do not.)

Key Takeaways

• States vary widely: Sales tax rules, deadlines, and formats differ dramatically from state to state.
• Nexus keeps evolving: Physical, economic, and marketplace nexus rules continue to shift — and vary by jurisdiction.
• Some states are especially tough: Places like California, Colorado, Illinois, New York, and Louisiana come with added complexity.
• Accurate data matters: Clean, consistent tax data is essential for timely and accurate returns.
• Deadlines can get messy: Filing frequencies and prepayment requirements change as you hit new thresholds.

Whether you file in two states or twenty, this episode will help you better understand the pitfalls, patterns, and prep work needed to stay compliant across the country.

The foundation of compliance starts here!

In this episode of Beyond Death & Taxes, Matt and Clay dust off the fundamentals of compliance with highlights from Avalara’s popular “Sales Tax 101” webinar. They uncover why sales tax matters, how nexus really works, and the five essential steps every finance team should follow to stay compliant.

Along the way, we make a pitstop in the Compliance Graveyard, burying one of compliance’s longest-lived myths: the assumption that sales tax is always somebody else’s problem.

Key Takeaways

• The old “someone else handles sales tax” mindset is officially dead.
• Why sales tax is critical to state budgets — and why it should matter to you.
• The three basics of taxability (Where, Who & What) and how they drive your obligations.
• The five core steps to staying compliant — from registering to remitting.
• Common nexus triggers that could create unexpected tax liabilities for your business.

Even the “basics” of sales tax can trip up the best finance teams. Learn how to spot the risks and streamline compliance before it becomes a headache.

Tax rules are shifting fast in 2025 — are you and your finance team keeping up?

In the debut episode of Beyond Death & Taxes, hosts Matt and Clay kick things off with highlights from Avalara’s 2025 Midyear Tax Changes update. From shifting nexus thresholds to the latest digital compliance rules, they walk through the most important legislative changes shaping tax and finance this year. Along the way, they revisit the now-buried “nexus guessing game” and share practical insights to help finance teams stay ahead of evolving state policies.

Whether you missed the live webinar or just need a quick refresher, this episode packs in everything you and your team need to know to stay compliant — without the guesswork.

Tune in to learn:

• Why the old “nexus guessing game” belongs in the compliance graveyard — and how modern tools make it obsolete.
• The most significant midyear legislative updates across states including Maryland, Washington, and Louisiana.
• How states are expanding their tax bases into digital goods, advertising, and professional services.
• What shifting economic nexus thresholds mean for remote sellers and marketplace facilitators.
• Why AI and new audit tools could change how states enforce compliance going forward.

Stay sharp on the tax changes that matter most — and get the insights you need to keep your business compliant in 2025 and beyond.

Subscribe to Beyond Death & Taxes today, and be ready for whatever compliance throws your way.