7 min 7 sec

Bucket List Becomes Swashbuckling Adventure Tour Company

A small-town Oregonian grows a travel blog into a multiple six-figure business.
Adventure High Profit Service Travel

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What It's About

You might call it 'Living the dream' ... this hustler designs epic trips, and then gets paid to take people on them.

Business Model
Skills Required
Planning & Coordination
Profit Potential

Words of Wisdom

Chase suggests connecting with others who have similar hustle ideas to your own. Talk with those who have walked a similar path and ask them about all of their failures and what they wish they would have known before starting.

Fun Fact

Embracing the, “Yes, I’ll figure it out and make it happen” mindset has created enormous possibility for Chase. A guy recently hired his company to have Seal (famous singer) perform four songs for his birthday, then fly him to Japan to meet with a sword maker who reads your soul before he makes your sword.

Notes from Chris

Episode 735
Cue the Indiana Jones themed-music and meet Chase Boehringer. He’s the chief adventure architect of his tour company, The Bucket List Lifestyle. His job allows him to take small, lively groups of people on the world’s most epic adventures.

He’s led all kinds of these adventures, including trekking to Mount Everest Base Camp, celebrating the Holi Festival in India, and attending the carnival in Rio de Janeiro.

Although Chase is now living life to the fullest, that wasn’t always the case. He’s from a small town in Oregon with barely 300 people. Growing up, you were expected to graduate high school, get married and land a job at the local plywood mill. Maybe treat yourself to a Hawaiian vacation if you’re lucky.

After a series of life events, Chase spiraled into a deep depression. It was from that point that he started writing his bucket list. A list of things he never thought he’d be able to do, but wrote them anyway. His list served as a light at the end of the tunnel.

He started a blog and began to tick items off that list. One by one, Chase started ticking items off his bucket list. Every item he completed gave his life direction and pulled him farther out of depression.

After three years of frequent solo travel, posting on his blog and growing his audience to several thousand, his cup was full. Now, he wanted to share the amazing experiences he had been having with others.

His idea was to get people to come on a trip with him. He’d simultaneously design the trip and make a profit. After all, people were already willing to pay for these trips. Why shouldn’t others benefit from his world-traveling expertise?

The first adventure Chase booked was from a Facebook post. It read, “Who wants to run with the bulls in Spain with me this July?” The response was overwhelming. So, he found a great deal on an Airbnb and booked the trip. The Bucket List Lifestyle was born.

Chase arrived at pricing by asking himself three questions: 1) How much will it cost? 2) What’s the experience? 3) What’s it worth to me?

The location of the trip also played a role. For example, India is cheaper to visit than Tokyo. Chase said his trips usually run between $1,500 - $3,000. The key is to gauge the experience factor while keeping prices reasonable.

He’s currently contracted for six more of these high-end adventure tours with one coach alone in 2019. These could be anything from getting a healing from a Maasai medicine man in Africa to climbing Mt. Kilimanjaro to taking groups to Thailand.

So, what’s next for The Bucket List Lifestyle? Chase is writing a book on world travel and giving talks about the freedom of following your bucket list. He’s also currently in the process of hiring more staff (this time more deliberately) to set his business on autopilot.



Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,


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Quote of the Day
"Prepare yourself mentally, emotionally, and financially so the leap isn’t terrifying. See the risk and mitigate it."
—Chase Boehringer #SideHustleSchool

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To infinity and beyond,

Chris Guillebeau