Side Hustle School Ep. 3366 - Failure Friday: “A $300 mistake cost me $100,000”
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Mar 20, 2026 Joel Runyon, founder of the Impossible brand and endurance entrepreneur, shares a trademark nightmare that spiraled into years of legal drama. He recounts early cost-cutting mistakes, the turnaround after hiring top IP counsel, and the $300 registration that would have prevented nearly $100,000 in costs. He urges timely legal protection for growing side businesses.
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Getting Sued Over The Name Impossible
- Joel Runyon woke up to a lawsuit from a company that had trademarked the name Impossible despite his prior use.
- He spent two years and nearly $100,000 fighting it after trying cheap and barter legal help before hiring elite IP counsel.
Register Trademarks When Side Hustle Earns $5k Monthly
- Do register trademarks once your project becomes a real business to avoid future legal exposure.
- Joel recommends filing when you reach about $5,000/month; filing costs about $300 plus optional lawyer fees.
Cheap Legal Help Can Multiply Costs
- Trying to save money on legal work can escalate costs dramatically if the case worsens.
- Joel's cheap and barter arrangements led to missed deadlines and worsened legal position, forcing costly elite counsel later.