Sales Tax Mistakes That Could Cost You When Selling Your Business With Jessica Rhoads [Ep.181]

Jun 24, 2025

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As Benjamin Franklin famously said, “In this world, nothing is certain except death and taxes.” But for online business owners, taxes aren’t always so certain, especially when it comes to sales tax.

In this episode, we’re joined by Jessica Rhoads. Jessica is an internationally experienced CPA and self-confessed “dumpster fire accountant” who specializes in helping business owners untangle messy tax situations.

We cover the key types of taxes every entrepreneur should understand, and zoom in on the one that’s most commonly misunderstood, and most likely to derail a future exit: sales tax.

Jessica breaks down how sales tax applies to non-tangible goods like SaaS products and apps, what triggers a sales tax nexus, and why ignoring it can lead to massive headaches during due diligence. She also shares insight on the best and worst states to set up your business from a tax standpoint, when to file a Voluntary Disclosure Agreement (VDA), and how to stay compliant if you’re selling across borders.

If you're building a business with the goal of selling one day, this episode is a must-listen. It could save you from tax troubles that scare off buyers, or cost you more than you bargained for.

Topics Discussed in this episode:

The different types of taxes businesses should be aware of (03:45)
Why sales tax is so important when selling your business (06:49)
How sales tax is applied to software and apps (11:43)
An overview of sales tax nexus (17:30)
The different tax softwares that can help you figure out your taxes (19:50)
The best and worst states to set up your business in (23:07)
How to stay compliant if you have sales tax nexus (28:16)
How tax works if you’re selling in foreign countries (30:37)
When to file a VDA (33:56)
A major misconception founders have about sales tax that hurts them later (39:39)

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Sit back, grab a coffee, and learn how to get your business taxes in order - before it’s too late.