Wise Words with John Roa

We caught up with John Roa, founder of the global scavenger hunt initiative Rambler, which gamifies travel with the aim of injecting some purposeful excitement into travelers' wanderings.

Rambler aims to pair inquisitive travellers with unique experiences — gamifying travel with a points system to offer something a little different from well-worn tourist trails. Founder John Roa first came up with the idea when, after extensive travelling, he realised that there was no easy way to find out what was going on off the beaten track. Tired of arriving in a new country without any good local recommendations to guide him, he set up the company with the aim of widening a traveller’s experience, through the means of scavenger hunts in new locations.

When we first came across Rambler in March of this year, it was clear that the figure behind this adventure initiative was a busy man. In fact, Rambler is just one of the many ventures founder John Roa has a hand in. He also founded design firm AKTA in 2010, social initiative Digital Hope and SocialCrunch.

His first experience of founding a digital company was at the age of 15 and he happily admits that ‘without the internet, I would probably be homeless’. His background is in marketing and advertising, and after graduating from Western University with a BBA in Sales and Marketing he started out in his career working on increasing brand recognition for other companies. We caught up with John to find out how the early stages of Rambler have been coming together so far.

1. Where did the idea for Rambler come from?

I travel a lot and the more new places I visited, the more I became frustrated about a way to find unique, adventurous things to do, that extend away from a normal guidebook. This crystalised for me while I was in Buenos Aires, Argentina. We weren’t overly impressed with steak houses and tango, which was just about all the other tourists said there was to do. I randomly spoke to a friend on Facebook who used to live there and she directed us to an underground drum show called La Bomba del Tiempo, which was one of the coolest things I had ever seen. While this made our B.A. trip, it was also frustrating that I was only able to find out about this show randomly. There was nowhere to look for stuff like this. Six months later, in Iceland, I was experiencing something similar when I met a girl who was on an Icelandic scavenger hunt. She had to find puffin being served on a menu, a local named Gunnar, and a street sign with more than 40 letters. I thought this was absolutely brilliant. Between both of these, Rambler was born to give real travellers a way to build a fun, experiential game out of travelling that is curated by travellers just like them.

2. Can you describe a typical working day?

Well, Rambler is one of about five projects I am currently working on, and is very much my fun side project (I built it in 12 days over Christmas break). I give it as many nights and weekends as possible, which is a great way to keep my mind (and programming skills) fresh! The rest of my day is spent running AKTA, Chicago’s leading UI/UX studio, as well as Digital Hope, a 501c3 nonprofit focused on changing the way the world donates to international NGOs using social media. Between all of these, I am either hard at work at my messy desk in our badass Chicago loft office, or on an airplane to some corner of the world!

3. How do you unwind or relax when you’re not working on Rambler?

Relax? Not sure what that means. I’ve always preferred speeding up rather than slowing down, so life is generally organised chaos. My recreational/Digital Hope travel is far and wide — my personal release. I love exploring a new town or taking part in a great volunteer project. I’ve visited about 20 countries in the last year or so and don’t intend to slow down!

4. What’s the secret ingredient to success as an entrepreneur?

Passion. Without a doubt. If you truly care about something and are willing to invest yourself, you can succeed. But it is a commitment. You must be the one pushing and pulling and kicking and screaming to achieve your goal or no one else will behind you. This leads to the (underrated) skill of being able to delegate. This is amazingly important but only possible if you have led by example and surround yourself by talented, trustworthy people.

5. What drove you crazy when building your business?

I would love to say that everything was a welcome challenge, but there were certainly things that were frustrating beyond belief. The sacrifice is one. You truly need to prioritise life, and that means making concessions both personally and professionally and that is a tough pill to swallow. You will inevitably miss important dates, ruin relationships and be disconnected from many people. It’s part of the game. Another is nay-sayers. There are always people who want to beat you up, make you question your gut, or just downright don’t like to see success. I learned you have to smile and wave (or maybe flip the bird) but most importantly plow through and believe in yourself. Lastly, (and pardon my colourful language), is a**holes. You will inevitably in life and business come across plenty of people who don’t play by the rules, and who are out to damage and steal. This needs to be considered in every plan and is wholly unavoidable, which is wildly frustrating!

6. What motivates you to keep going?

I have the coolest life I can imagine. I run a number of fun companies made up of amazing people. I travel the world helping those less fortunate via Digital Hope. I get to be at the center of the digital start-up craze that is sweeping the world. My motivation is baked into my desire, and fortune, to be able to focus on the things I want to focus on and live the life I choose.

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

I would probably take more risks and attempt more things. My friends and family would call this insane, as it already appears there are far too many irons in the fire, but to me there isn’t a limit to opportunity if you are out looking for it.

8. Where do you see your business in five years, and how will you get there?

I hope Rambler continues to organically grow, and used as a resource to make travelling cooler. I am not a spiritual person, but travelling is the closest concept to that for me, so knowing this product could heighten that for others is very exciting. As far as AKTA, Digital Hope, SocialCrunch, and my other ventures…I hope to see them grow in the way they were born: great people coming together to solve real challenges that positively affect the world.

9. If you weren’t working on Rambler, what would you be doing?

I often dream of completely disconnecting and living life as a travelling nomad. I would probably get bored in weeks and start creating businesses or something, but it is always in my head.

10. Tell Springwise a secret…

In past lives, I’ve played competitive lacrosse, paintball and poker. I foster kittens, do photography and card magic. I love flying but hate landing. I rarely travel for fun in the USA but am obsessed with Las Vegas. I partially grew up in Venezuela. I’ve become a complete airport snob. The older I get, the more of a thrill-seeker/risk-taker I’ve become. I aspire to become the second most interesting man in the world (or Richard Branson). I will always act half my age. I don’t ever intend to wear a business suit again. I once spent a Vegas weekend convincing the world that I was a member of a British boyband…successfully. There, now you know all of my secrets.

11. Any final words for aspiring entrepreneurs?

Stop thinking about it and do it. And when you fail, do it again. You can read more about Rambler in our article here, or visit the Rambler website here.