Chris Stakich

A sound strategy, solid product, clever marketing, and world class customer service are all key ingredients. But what separates good from great is often your willingness to take it to the next level.


Rustic Pathways CEO Chris Stakich has dedicated his career to the intersection of education, travel and philanthropy. Chris joined Rustic Pathways, a global leader in community service and education based travel for students, in 2002 after graduating from Harvard University with a BS in Economics. Chris was appointed Rustic Pathways CEO and Chairman of the Board of Rustic Pathways in 2014. Prior to being appointed Rustic Pathways CEO, Chris held several positions within the company, including: COO, Global Sales Director, Business Development Director, Costa Rica Country Director, and Program Leader.

During Chris’ tenure at Rustic Pathways, the company has grown 40 times in size; employing over 500 people and recruiting students from 60+ countries to work and live in some of the most remote villages in the world. At Rustic Pathways, Chris has developed company strategy, built the executive team, established growth partnerships, and overhauled the client lifecycle.

In addition, Chris also serves as the Chairman of the Board of Thinking Beyond Borders. Poised as the most rigorous Gap Year experience, Thinking Beyond Borders takes students around the world to study global development issues from social, political and economic perspectives.

Chris also serves as a board member of Thrival Academies. Thrival Academies is creating the largest national network of schools specifically set-up to provide middle and low-income students with a 1-year study abroad experience. The goal is to enroll 50,000 students each year by the year 2030.

Over the past five years, Chris has also served as a board advisor for Global Citizen Year, Lifestyle Rewired, Trip Weave and his high school Alma Mater, University School. Chris lives in San Francisco with his wife and three sons, and is committed to developing future leaders who embody compassion and global understanding.

Where did the idea for the Rustic Pathways Foundation come from?

The Rustic Pathways Foundation was born as a natural extension of the Rustic Pathways company. As a company, Rustic Pathways takes students into remote villages in developing countries to work on community development projects. Over the years, we’ve had many clients offer to donate money and supplies to our projects. We realized that through a 501C3 non-profit, we could dramatically increase the positive impact that we create around the world. Last year we raised over $250K for the communities and countries that we serve.

What does your typical day look like and how do you make it productive?

I’m an incredibly early riser so my days start at 4am. To make the most of every day, I stick very closely to a pre-planned schedule. My theory is “plan ahead and execute in the moment”. From 4am – 5:30am I typically meditate, read, and focus on personal development projects. From 5:30am – 7am I clear emails and wrap my head around the day’s activities. From 7am – 9am I feed my kids breakfast and get them to school (I have three sons under six years old). From 9am – 4:30pm I follow a very scheduled day filled with meetings, phone calls, projects, and travel. By 5pm I’m home for quality time with my wife and kids and I don’t look at technology until the following day – and that’s a strict rule.

How do you bring ideas to life?

In some companies, they have people who start small fires, people who fan, grow, and spread the fires, and then people who make sure that good fires stay burning efficiently and always have enough wood to keep going. I’m a fire starter, my brain is always racing, I see opportunities, inconsistencies, and patterns everywhere I go. When it comes to “bringing ideas to life”, I’m lucky enough to work with one of the best executive teams I know who bring those small ideas to life.

What’s one trend that really excites you?

ONE?!? WOW!! There are a lot of very exciting trends out there. My favorite would be the vision of self-driving cars that function on 100% solar power. Imagine a world where you never had to drive, where during every commute you could work, read, exercise, watch TV, socialize or sleep, and there was no negative environmental impact. Who’s up for a trip from Los Angeles to New York City ;))

What is one habit of yours that makes you more productive as an entrepreneur?

I take notes constantly and convert them into various types of lists. The Checklist Manifesto is a must read for every aspiring entrepreneur. It takes creativity and transforms it into action.

What was the worst job you ever had and what did you learn from it?

I delivered furniture for many years, served as a lifeguard, worked in the back office of NFL teams, took out the garbage at restaurants, was an announcer for college sports, drove trucks . . . and I never had a bad job. I love people and believe that you can learn new skills every single day.

If you were to start again, what would you do differently?

I would have taken more risks, not worried so much about “being on a path”, and just followed my heart into a world of exploration.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I set annual and monthly goals for myself professionally and personally and circle back on them once a week. It’s a great way to track progress and accomplish a lot.

What is one strategy that has helped you grow your business? Please explain how.

In college, I played varsity football and it solidified my belief in hard work. A sound strategy, solid product, clever marketing, and world class customer service are all key ingredients. But what separates good from great is often your willingness to take it to the next level. To be clear, I’m NOT a fan of late nights at the office or 60+ hour work weeks. I am a fan of understanding your goals, committing to a plan, and executing it at the 100th-percentile.

What is one failure you had as an entrepreneur, and how did you overcome it?

I’ve thrown some fundraisers and industry events where no one shows up. Boo-hoo. You make the best of it and move on.

What is one business idea that you’re willing to give away to our readers

A private college costs $50K – $65K per year. Originally people enrolled in college to “get a good education”. The content of the best MBA programs in the world is now online, FOR FREE, through massive online education courses. Some people claim that the value of college is the people you meet, and the group of peers that you learn with. Why not set-up a college where the curriculum can be learned online, for free or at a minimal cost, and combine that with traveling the world with a group of 100-200 people who are all taking the same course while also learning the lessons of life. That’s a re-invention of college, and the multi-billion-dollar concept is scary, but it’s a future vision of higher education.

What is the best $100 you recently spent? What and why?

I bought the book Barbarian Days (way cheaper than $100). One of the best stories I’ve read in a decade. If you surf, get it now.

What software and web services do you use? What do you love about them?

One of my favorite software systems is Evernote. The ease in keeping lists is wonderful. I’m also a huge podcast user, Spotify user, and Uber user. They all dramatically enhance my life and get the job done.

What is the one book that you recommend our community should read and why?

Good to Great or Playing to Win for business purposes. The Power of Now, The Peaceful Warrior, Man’s Search for Meaning, The Alchemist, or Siddhartha for spiritual development. And Fierce Invalids Home from Hot Climates for fun.

What people have influenced your thinking and might be of interest to others?

I’m working offline but names include Elon Musk, Peter Drucker, Jim Collins, Steve Jobs, Richard Branson, Elkhart Tolle, Dan Millan, the Dahlia Lama, Barack Obama, Wayne Dyer

Key Learnings:

  • I am a fan of understanding your goals, committing to a plan, and executing it at the 100th-percentile.
  • One of my favorite software systems is Evernote. The ease in keeping lists is wonderful.


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