At the helm of one of the largest independent travel media companies, San Francisco’s Ross Borden is a man that’s “always on”. 

Having bootstrapped his company with $11,000 and a big dream, he’s grown it into a multimillion dollar business with a team of over 60 people.

Borden embodies the essence of a “Challenger,” the crux of Dockers’ global campaign, which focuses on people who inspire change in their communities by the way they think and act. It’s a part of the brand’s larger platform – Always On – that showcases men who are always ready to tackle whatever comes their way.

Tell us about Matador. What does the business offer, and why did you feel the need to create it?
We created Matador because all the major travel magazines and websites were about hotels, resorts, and restaurant reviews. We believe that the soul of travel is in experiences. That can’t be bought, and the people you meet along the way. We have built a platform that serves passionate travellers with articles, videos, city guides, and a social app.

What does ‘adventure’ mean to you? How would you compare that to building a business?
Good comparison! Something is only an adventure when things start going wrong. And I don’t know anyone who has built a successful business where a lot has not gone wrong before they got it right.

What have been some of the biggest challenges that you have overcome in your path to where you are now?
I started with $11,000 and no experience in launching a business. From building a website to  hiring a team, I made a ton of mistakes but learned from every one of them.

What is it about travel that you think brings people together? 
Everyone experiences travel differently but I think it gives everyone a special feeling that we can all relate to: The feeling of experiencing a new culture, trying new food, hearing a new language, and blissfully getting “lost” in a new land. It’s one of the most empowering and enlightening things we can do as humans.  

As a frequent traveller, what is the best advice you have?
If you fly a lot, pick one airline and stick with them! [You’ll] thank me later.

What is the greatest lesson that you have learned from travelling?
Travelling is the only means by which humans will have an understanding and acceptance of each other. It is incredibly important for people to travel and realize that we are not all that different after all.

How does Dockers’ Smart Series fit into the fabric of your business and life? 
It’s versatile, flexible, and ready for anything, which is good for my lifestyle and the way I travel.

How do you define success?
Freedom, and being stoked every Monday morning.