The Hidden Tax Mistakes That Kill E-Commerce Businesses (and How to Avoid Them)

The Hidden Tax Mistakes That Kill E-Commerce Businesses (and How to Avoid Them)

From How To Ride A Roller Coaster by David Ezell

December 16, 2025 · 37 min · Episode 92

About this episode

This episode discusses common tax mistakes in e-commerce and how to avoid them with expert Jared Smithson.

Selling online feels simple... until taxes quietly start working against you. In this episode of How to Ride a Roller Coaster , host David Ezell sits down with Jared Smithson , Founder of RJM Tax Exemption and one of the leading experts in U.S. e-commerce tax compliance. Jared has helped over 5,000 businesses navigate sales tax, multi-state nexus, and regulatory landmines that most founders don’t realize they’ve stepped on until it’s too late. You’ll learn: The most common sales tax mistakes e-commerce founders make (including the “one-click” Shopify error) Why revenue growth can be fake growth if compliance isn’t handled correctly How economic nexus actually works (and why $100K isn’t the only number that matters) Why collected sales tax isn’t “your money”—and how it can block an exit What’s changing next for digital products and services taxation When to DIY vs. when to bring in experts (without wasting money) Whether you’re selling on Shopify, Amazon, Walmart , or planning to expand into the U.S. market, this conversation could save you six figures, months of stress, and a painful audit . Show links: RJM Tax Exemption: https://rjmtaxexemption.com/ Jared…

People in this episode

Host: David Ezell

Guest: Jared Smithson

Topics covered

  • e-commerce
  • tax compliance
  • business mistakes
  • entrepreneurship
  • financial regulations

Keywords

  • sales tax mistakes
  • one-click Shopify error
  • fake growth
  • economic nexus
  • collected sales tax
  • digital products taxation
  • DIY vs. experts

Mentioned in this episode

Products: Shopify, Amazon, Walmart

Books & works: How to Ride a Roller Coaster

Places: U.S.

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