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Side Hustle School

Ep. 3366 - Failure Friday: “A $300 mistake cost me $100,000”

Side Hustle School

Chris Guillebeau

Business, Side Hustle, Small Business, Careers, Entrepreneurship,, Entrepreneurship

4.73.3K Ratings

🗓️ 20 March 2026

⏱️ 9 minutes

🧾️ Download transcript

Summary

In this week's new “Failure Friday” segment, we hear from the founder of a lifestyle and apparel brand who wakes up one day to find out he's being sued. 

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

Show notes: SideHustleSchool.com

Email: team@sidehustleschool.com

Be on the show: SideHustleSchool.com/questions

Connect on Instagram: @193countries

Visit Chris's main site: ChrisGuillebeau.com

Read A Year of Mental Health: yearofmentalhealth.com

If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼 



Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.


Show notes: SideHustleSchool.com

Email: team@sidehustleschool.com

Be on the show: SideHustleSchool.com/questions

Connect on Instagram: @193countries

Visit Chris's main site: ChrisGuillebeau.com

Read A Year of Mental Health: yearofmentalhealth.com


If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼 


Hosted on Acast. See acast.com/privacy for more information.

Transcript

Click on a timestamp to play from that location

0:00.0

This week I'm hosting neurodiversion an event in Austin, Texas, featuring people from all over the world.

0:10.9

In fact, hundreds of people who have come into town.

0:13.5

Check it out at neurodiversion.org or a neurodiversion event on Instagram, TikTok, YouTube as well.

0:20.2

That's what I'm doing in my non-Sidustle school life, but naturally the, YouTube as well. That's what I'm doing in my non-side hustle school life,

0:22.5

but naturally the podcast continues as well. So today, we've got a failure Friday segment.

0:28.8

Failure Friday. It is basically a story of a mistake, a misstep, a disaster, something that goes

0:33.3

wrong. What does the side hustler or the entrepreneur, the business owner, what did they learn through this experience? How are they able to regroup? How are they able to hopefully come back stronger? But also, it's not just about the after. I want to take people through the actual experience of what did it feel like in that situation because it's not always pleasant. You don't always feel like, yeah, it's all going to be okay. Often in that moment,

0:54.3

you can feel pretty discouraged. So in this segment, we're going to hear from a friend of mine. This is Joel Runyon. I've known him for, I don't know, 15 years now or so. I knew him before he started this business and he's gone on to grow this business, run an ultramarathon on every continent, raise lots of money for charity, do all kinds of other cool stuff as well. He is just an inspirational

1:14.0

dude. run an ultra marathon on every continent, raise lots of money for charity, do all kinds of other

1:11.6

cool stuff as well. He is just an inspirational dude. We featured him in some other episodes over the

1:16.5

years. But today, again, Failure Friday, we're going to talk about something that did not go well.

1:20.6

A $300 mistake that cost him $100,000. You heard that right. A $300 mistake that cost him $100,000.

1:29.7

Joel is also from Austin, or at least he's been living in Texas for a while.

1:33.3

I'm going to pass the mic to him, let him tell the story.

1:35.5

I'll come back at the end with a few words of wrap up.

1:48.2

Hey, my name is Joel Runyon, and I run a site called Impossible.

1:54.3

It's a blog and lifestyle performance company focused on helping people push their limits and doing something impossible.

2:02.3

This is the story of how a $300 mistake cost me nearly $100,000, two years of my life and resulted in an epic story about getting sued by a billionaire. Sounds cool, right? Not so much. Anyways, I started this company about 10

2:09.2

years ago and I quickly settled on the name and logo, an all-caps version of Impossible with a

2:14.6

distinctive line through it. I trademarked the logo, but I didn't bother

2:18.6

trademarking the company name. I didn't want to spend tons of money on the trademarks or other

2:22.9

legal work early on, and I knew that you get a common law trademark when you start using it,

...

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