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Side Hustle School

3302 - TBT: Mystery Trip Biz Doubles Down on Thrills

Side Hustle School

Chris Guillebeau

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

4.73.3K Ratings

🗓️ 15 January 2026

⏱️ 8 minutes

🧾️ Download transcript

Summary

In this week's “Throwback Thursday” segment, we hear from Dave Green, the founder of Mystery Trip. His in-person event planning service has adjusted well to a hybrid world.

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

It's going to be a big year. And January is when so many of us set goals for our business,

0:04.8

for all the things we want to achieve. And in a small business or a side hustle, even,

0:09.6

cash flow can make or break you. So if your money gets tied up, if your tools don't connect,

0:14.1

every decision feels unnecessarily stressful. Maybe it's time to switch to Intuit QuickBooks's

0:20.0

money management tools. Big shout out to QuickBooks,

0:22.9

our sponsor, start the year with confidence about your goals. Learn more at quickbooks.com

0:27.9

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

0:34.7

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

0:43.6

Lemonada

0:44.2

Let me.

0:52.8

Let's talk about taking a mystery trip.

0:55.0

You want to take a mystery trip, or are you interested in the mystery trip business?

0:59.4

Personally, I'm not sure I want to take a mystery trip, but that's because I like to plan.

1:02.9

I like to be in control.

1:04.3

But there are all kinds of people out there who are interested in this type of business,

1:08.6

and that's what we're all about here on Saitosl School, looking at different case studies and how people have found a way to make extra income

1:14.9

without quitting their job. So in this week's throwback Thursday segment, we're going to take a look

1:20.3

at Dave Green, or we're going to hear from Dave, actually. He's the founder of Mystery Trip,

1:24.9

his in-person event planning service adjusted well to a hybrid world.

1:29.7

We first heard from Dave back during pandemic times. He'd started his business a couple of years

1:35.8

before that, worked with a lot of different brands and such, made it through the pandemic and

1:39.8

is still going strong with mystery trip in a variety of cities. Last week in this episode, we heard from

...

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