When you are in the thick of building a business, legal protections often feel like a ”someday” problem—until a cease and desist letter arrives. In this episode, Ryan sits down with Tiffany Donaldson, a trademark educator and attorney who is transforming how founders view intellectual property. Tiffany breaks down the critical difference between simply having a logo and owning a protectable asset that scales with your valuation.

We dive deep into the often-overlooked mechanics of brand protection, from the dangers of falling in love with a name before ”clearing” it to the complexities of using AI for logo design. Tiffany shares why intellectual property is often the only thing that survives a business collapse and how securing your trademark is actually a strategic investment in your eventual exit. If you are building for the long haul, this conversation is your blueprint for protecting what you build.

In this episode, you will learn:

• The ”Clearance” Reality Check: Why you must research your brand name before you commit, and how to avoid the costly mistake of trading on someone else's registered mark.

• The Whack-a-Mole Stage: Understanding your legal requirement to police your brand against imitators to prevent ceding your rights.

• AI & Copyright Risks: The nuanced current laws regarding AI-generated logos and why human authorship is currently required for full copyright protection.

• Asset Protection for Exit: How a registered trademark ensures your brand’s value matches the longevity of your operations when it’s time to sell.

• The Toys ”R” Us Lesson: A powerful look at how IP often retains value even when the underlying business operations cease.

About Tiffany Donaldson:

Tiffany Donaldson is a trademark attorney and educator who specializes in helping small business owners and entrepreneurs protect their brands. As the force behind Trademark Prospector, she focuses on demystifying the legal process, moving founders past the ”terror barrier” of legal costs, and helping them build foundational assets that secure their business's future.

Connect with Tiffany Donaldson & Cynergists

Guest Website: http://www.trademarkprospector.com

Cynergists Website: http://www.cynergists.com

Chapters:

0:00 – Intro

1:53 – Trademark Education & Strategy

4:05 – The Clearance Protocol: avoiding Lawsuits

6:27 – Scaling & Defending Against Imitators

9:04 – The Impact of AI on Copyright & Trademarks

13:42 – Exit Strategy: Maximizing IP Value

16:45 – Rapid Fire Questions

22:21 – Connect with Tiffany