• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
CommentaryTaxes

250 years after the Boston Tea Party, America still struggles to navigate its complex relationship with tax

By
Scott McFarlane
Scott McFarlane
Down Arrow Button Icon
By
Scott McFarlane
Scott McFarlane
Down Arrow Button Icon
December 15, 2023, 10:55 AM ET
There are currently over 900 different tax types that a tea merchant can encounter in the U.S. selling domestically and abroad.
There are currently over 900 different tax types that a tea merchant can encounter in the U.S. selling domestically and abroad.Getty Images

On Dec. 16, 1773, an import tax dispute with England set off one of the key sparks that ultimately led to the American Revolution. As we reflect on the significance of that event so long ago, there’s an opportunity to dive a little deeper into the topic of taxation and how it evolved in our country.

Had I paid a little more attention in high school, I might have understood that the nation whose founding principles included “no taxation without representation” was built on a federalist model that granted most day-to-day powers to the states, rather than the national government. Key among those powers was the ability to impose taxes at a local level.

People debate the pros and cons of our country’s federal system to this day, but there’s one thing nobody can deny: Our system of local taxation has created a tremendously complex, and burdensome, environment in which to do business.

Most people, even many tax experts, do not realize that there are more than 13,000 taxing jurisdictions in our country. Each with its own particular rates, rules, and compliance requirements. Imagine what that means for businesses that sell goods and services throughout the land.

To illustrate this point, and in honor of the Tea Party in the Boston Harbor way back when, let’s talk about tea. There are currently over 900 different tax types that a tea merchant can encounter in the U.S. selling domestically and abroad. Think about that: 900 potentially different considerations in charging, collecting, and ultimately paying tea taxes to individual governments.

Loose or bagged. Matcha or mint. Box or bulk. Served hot in-store or ready for you to brew at home. It all depends on which state you’re selling from as well as the state where the buyer resides. Every consideration changes the seller’s compliance exposure.

Most people are not aware of these complexities, and that extends to the people on the front lines of commerce. According to research our company did into the evolution of tax complexity, 94% of tea merchants are unclear on this question as well. In fact, eight in 10 modern tea merchants feel anxious about staying on top of the complexity and rate of change when it comes to sales tax on goods like tea.

But it’s not just Americans who are struggling to manage their transaction tax obligations. The British are still getting into hot water over it after all these years as well. Four out of five UK tea merchants have faced penalties or fines due to unintentional non-compliance with U.S. sales tax obligations.

And that is just involving tea. Most other goods and services sold in the U.S. are subject to their own set of compliance requirements. Unless they’re not, of course. But how do you know which items are subject to what taxes? Taxes affect every business, every person, every day. From the ancient Egyptians until recent decades, tax has been managed manually and businesses have struggled to keep pace with incredible complexity and fast-moving changes.

Fortunately, we have technology today that greatly relieves the burden of tax compliance from businesses of all sizes. Automation has freed many businesses from tax compliance management concerns.

250 years ago, soon-to-be Americans boycotted a tax on tea. Today, our own tax system has created complexity for businesses that the Boston Tea Party participants could have never imagined. And of course, taxes aren’t going away. As founding father Ben Franklin said in 1789, “Our new Constitution is now established, everything seems to promise it will be durable; but, in this world, nothing is certain except death and taxes.”

Scott McFarlane is the co-founder and CEO of Avalara, a provider of tax compliance automation software.

More must-read commentary published by Fortune:

  • Economic pessimists’ bet on a 2023 recession failed. Why are they doubling down in 2024?
  • COVID-19 v. Flu: A ‘much more serious threat,’ new study into long-term risks concludes
  • Access to modern stoves could be a game-changer for Africa’s economic development–and help cut the equivalent of the carbon dioxide emitted by the world’s planes and ships
  • The U.S.-led digital trade world order is under attack–by the U.S.

The opinions expressed in Fortune.com commentary pieces are solely the views of their authors and do not necessarily reflect the opinions and beliefs of Fortune.

Join us at the Fortune Workplace Innovation Summit May 19–20, 2026, in Atlanta. The next era of workplace innovation is here—and the old playbook is being rewritten. At this exclusive, high-energy event, the world’s most innovative leaders will convene to explore how AI, humanity, and strategy converge to redefine, again, the future of work. Register now.
About the Author
By Scott McFarlane
See full bioRight Arrow Button Icon

Latest in Commentary

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Leadership
  • Success
  • Tech
  • Asia
  • Europe
  • Environment
  • Fortune Crypto
  • Health
  • Retail
  • Lifestyle
  • Politics
  • Newsletters
  • Magazine
  • Features
  • Commentary
  • Mpw
  • CEO Initiative
  • Conferences
  • Personal Finance
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Commentary

CommentaryE-commerce
Agentic commerce will reward the fastest learners, not the biggest retailers
By Simon JamesFebruary 10, 2026
11 hours ago
abhas
CommentaryCloud
I’m Cloudera’s chief strategy officer and here’s why your $1 billion AI budget just became obsolete
By Abhas RickyFebruary 10, 2026
12 hours ago
chapman
CommentaryGender Issues
Sam Altman told me AI should be ‘an equalizing force in society.’ That’s why I’m working on the $1.6 trillion AI gender gap
By Valerie ChapmanFebruary 10, 2026
12 hours ago
women
Commentarynational debt
America is shorting one of its best assets as the $38 trillion national debt runs out of control 
By Katica RoyFebruary 10, 2026
13 hours ago
trump
CommentaryInequality
The economy isn’t K-shaped. For 87 million, people, it’s desperate and for another 46 million it’s elite
By Josh TanenbaumFebruary 10, 2026
13 hours ago
hudson
CommentaryPharmaceutical Industry
Sanofi CEO: The enterprise AI shift will reshape pharma in 2026
By Paul HudsonFebruary 10, 2026
14 hours ago

Most Popular

placeholder alt text
Economy
America borrowed $43.5 billion a week in the first four months of the fiscal year, with debt interest on track to be over $1 trillion for 2026
By Eleanor PringleFebruary 10, 2026
15 hours ago
placeholder alt text
C-Suite
Meet Jody Allen, the billionaire owner of the Seattle Seahawks, who plans to sell the team and donate the proceeds to charity
By Jake AngeloFebruary 9, 2026
1 day ago
placeholder alt text
AI
As billionaires bail, Mark Zuckerberg doubles down on California with $50 million donation
By Sydney LakeFebruary 9, 2026
1 day ago
placeholder alt text
Economy
China might be beginning to back away from U.S. debt as investors get nervous about overexposure to American assets
By Eleanor PringleFebruary 9, 2026
2 days ago
placeholder alt text
Economy
It turns out that Joe Biden really did crush Americans' dreams for the future. Just look at how the vibe changed 5 years ago
By Jake AngeloFebruary 10, 2026
6 hours ago
placeholder alt text
Success
Super Bowl champion Sam Darnold says his plumber dad played with him every day after work, no matter how tough his day was—and that taught him resilience
By Emma BurleighFebruary 9, 2026
1 day ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.