Getting Down & Dirty with Sean Keener – CEO of BootsnAll

We asked CEO and co-founder of BootsnAll, Sean Keener, a little bit about himself.   Come meet the man behind the plan to get you on your own RTW trip.

1. When did you first start traveling? Where have you been so far?

With Ma and Pa, not sure what year it was.  My 1st Long-term travel experience was in 1994.  As for where have I been, I don’t keep track.   I have NOT been to South America though.

2. What is one country, city, or place you’ve always wanted to see but haven’t had the chance to yet?

Chile.  It’s like California 100 years ago, except modern.

3. What do you do when you aren’t being “Sean-CEO of a BootsnAll?  How do you like to spend your off time?

To me, it’s about work-life integration, there is no such thing as work-life balance.  BootsnAll’s cause, A GAP year and/or RTW Trip on every resume is what drives me as it makes the world world a better place for your kids and friends and mine.

My time off, I like to “not plan” and go with the flow and energy of that day.  Some things that I keep coming back to are:

  • Yoga
  • SUP in the Gorge
  • Mountain Bike
  • Trail run/hike (tree bathing)

Be outside, and with people that care and are motivated.  I spend a lot of time with Willie Levenson of the Human Access Project.  He is a genuine bloke who is working tirelessly to change Portland’s relationship with the Willamette River.  I also spend time with Erik Ekman of OutsideVan.  He is my Joy coach and an all around fun and expansive mate.

I have 3 kids under 5 years old, and I’m happily divorced, so I’m grateful and enjoy the time I spend with them.

sean keener, bootsnall, family, father with kids, dad with kids, playing outside,

Sean playing outdoors with his kids; son Kai and twin daughters Blaize and Pepper.

That about covers it.

4. How did you first come up with the idea to start BootsnAll?

The short story is, I wanted to connect and share the lessons of the Code of Conduct that Chris and I came up with on a hike in Yellowstone in the summer of 1997.  The long version is here.

You’ve created now 5 free e-courses (RTW30, RTW30 – Families, RTW30 – Career Break, and the newest GapYear30-Students, & GapYear30-Parents) to help people plan long-term and around-the-world trips.

5. Why do you give away so much free information to people when many others are selling travel planning products?

LOL, I’ve been a small part of creating these courses.  Adam, Jenn, Sherry and many others have contributed to building and improving these courses!

Why?  I want to see a GAP year or RTW trip on every resume.  I don’t care, if everyone books through our site.  In fact, we refer people to other companies if we are not a good fit.  We are a purpose based company versus a profit based company.

6. Where do you live and why do you like living here? What is one place in your town you think is a ‘must see’ for visitors?

I live in White Salmon, Washington and also spend some time in Portland, Oregon.

For White Salmon – which is really the Columbia River Gorge, a must see is to get outside, and move/exercise in the gorge.  On the river, on the trails, where ever.  It’s all “must see”.  Visit Everybody’s Brewing after your outdoor experience.

In Portland, Get on the Wildwood Trail in Forest Park.  I walked the entire trail last summer in 1 day and it’s full on tree bathing.  Afterwards, hit the Sip Juice Cart and Salt and Straw on Alberta.

7. Why do you think travel is important?

Long-term travel is perhaps, the best way to get a boots on the ground education.  It did for me.

I thought the Chicago Cubs, Bears, Bulls and Blackhawks are what mattered most until I left home and started seeing the world from other’s perspectives.  It’s emotional and inspiring to connect with the world outside of the perspective I was brought up in.  I realized, “I can do anything” – versus the fear based ideas I had before.

I’ve seen about 100,000 people via BootsnAll and AirTreks do long-term travel and realize that YES, it is important.

Sean Keener,. family, bootsnall, daughters, twins, father and daughter

Sean with his twin daughters Blaize & Pepper.

8. Do you speak any other languages? If so, which ones and at what level?

Spanish – Spanglish level.

9. You started BootsnAll in 1998. If you were to start BootsnAll today, what things would you do differently?

Go harder, go more aggressive from the get go.  Not be afraid, fail more often, but smaller fails.

10. You like to read. Name 3 books you recommend people read (any kind of book) and why do you think people should read it?


  • 7 Habits of Highly Successful People – This is a classic and principle driven ideas on how to drive success/happiness.
  • Vagabonding – Rolf nailed this book, and it’s the inspiration in many ways for the Indie Travel Manifesto that Rolf and I co-created.
  • Essentialism – Less is more.  Less house, more travel.  Less clothes, just ones you love, and more stuff that matters.

11. What advice would you give someone who has never traveled?

Emotional advice:  You will not regret doing this trip on your deathbed.  I’ve yet to hear from a traveler, even one’s that had difficulty that they “should not have” done the trip.  Most come back with a joy factor baked into life.  Why not you?

Logical Advice:  The world is changing so fast, and a boots on the ground education from an RTW trip will give you a leg up on all the people who follow the robot path.  Don’t be a robot.

Credibility Advice:  I’ve been talking to travelers for 20+ years now, and helped over 100,000 do long-term travel.  I can say, “it works” with conviction.  Go get it for yourself.

Bonus Question: If you could be any superhero, who would you be and why?

I feel like I already am a super hero.  We all are.  Some people just don’t know it or let themselves be it.  :)  – I would be or perhaps am, Yoda.

Sean was recently a finalist for Entrepreneur of the Year with EO (Entrepreneurs’ Organization) Portland.  We are wicked proud of him and you can read more by clicking the link. 

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