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Side Hustle School

3338 - Failure Friday: “They just weren’t interested in what we were selling…”

Side Hustle School

Chris Guillebeau

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

4.73.3K Ratings

🗓️ 20 February 2026

⏱️ 8 minutes

🧾️ Download transcript

Summary

In this week's Failure Friday segment, we hear from the co-owner of a business that livestreams weddings. When Covid struck, they thought they had the perfect opportunity to expand to a new market—but buyer interest fizzled. 

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

The easiest way to scale your business is to stay connected and not just with your team,

0:05.2

but also your money, your cash flow. That's why you want to make the switch to Intuit QuickBooks

0:10.3

Money Management Tools. With QuickBooks Money Tools, your money and your books are synced

0:15.3

together in one platform. You get real-time insights and visibility. You can see the cash

0:20.6

coming in, going out. You can see your

0:22.8

vendors, what you need to pay, what you can expect. This has been a problem for me sometimes in the

0:27.4

past. So I love the idea of having just simple clarity. Reclaim that clarity and control so you can

0:33.3

grow your business with QuickBooks Money Tools today. Learn more at QuickBooks.com

0:37.6

slash money. Again, that's quickbooks.com slash money. Terms apply. Money movement services

0:43.2

are provided by Intuit Payments Incorporated, licensed as a money transmitter by the New York State Department of Financial Services.

0:52.6

Lemonada. I believe we can learn as much from failure as we can from success, if not, in fact, more.

1:06.8

And that's why every so often, well, every other week.

1:09.3

In fact, we run a segment called Failure Friday.

1:12.5

It is a collection of short stories all about mistakes, missteps, disasters, and of course, failure.

1:16.8

You get to hear directly from a side hustler who has struggled to get something off the ground or otherwise encountered a big setback, and you get to hear what happened along the way.

1:25.1

Like, you know, what do they do in response? How do they

1:27.5

regroup, move forward, et cetera? Today we're going to hear a lesson I'm titling, they just

1:32.8

weren't interested in what we were selling. And this is pretty interesting because we told

1:37.1

the story of this guy's live stream wedding business. His name is Del Wilson. He operates it

1:42.4

together with his wife, Lydia. We told that story way back on

1:45.3

episode 1669. So this goes back many years, actually pre-COVID. And when COVID struck,

1:53.2

you remember that thing, right? That whole global pandemic. They thought, surely with what we do for

...

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