Meet the founder of Rad Season




Hi Oli, I love what you’re doing, so of course I’m intrigued to find out about the man behind this amazing company. Tell me a little bit about yourself.

I'm Oli Russell-Cowan (pleased to meet you)- a guy who created Rad Season as a solution to a problem in an industry I love. Rad Season is the world's first platform bridging the industry gap between online travel agent, event directory, and media. We specialize in the adventure travel + action sports niche, providing a community for rad enthusiasts and athletes alike. With 15+ years of my own personal experience in International business development, spanning multiple industries including Events, Media, Digital, ICT, the Arts, Action Sports, Travel and Tourism, this industry has always been a natural fit for my interests and skills.


So, you went on your honeymoon to Latin America, came back and made a swift decision to move to Australia and shortly after launched Rad Season. Tell me more about that journey and why Australia?

Fun fact: my first travel job was as a surf instructor/tour guide in Fuerteventura, Canary Islands. With my love for surfing acting as a big motivator for my move from the UK to Australia, you could say adventure is in my blood. I really believe we have certain tendencies ingrained in us that propel us toward a dream or vision, and it looks like Rad Season was mine. While traveling on my four-month honeymoon in Latin America, I found it difficult to find cool events and festivals going on that had an element of adventure and general ‘radness’ to them. There was no detailed information or website with an easy-to-use calendar or location map showing what the current festival and events season was, or where to find the happening spots for action sports and cultural events. I knew that there was always something rad worth going to see in the world. I just had to find it. I held the idea for Rad Season in my mind and knew there was a niche for adventure travel that wasn’t being served.




How did you develop key partnerships to grow Rad Season?

In the startup space, you have to really hustle to get your brand 'out there'. Early on, I utilized AngelList , "where the world meets startups", to create my startup profile and build brand awareness, since PR is more than just a press release in this technology age. Paired with building strategic journalist relationships (outreach with influencers whose "beat" closely aligned with my messaging), my brand was picked up by Skift as One of the New Travel Startups to Watch. This accolade led to a big win for Rad Season: Priceline contacted me about a partnership to provide streamline travel accommodations to adventure travelers. What started out as a passion for travel and adventure has now transformed into the world’s first one-stop-shop for all your action sports and adventure festival booking needs. We're redefining the way people travel; moving beyond the "tourist bubble" and bringing cultural and adventure experiences to a new generation of traveler.


Do you take the time to build an entire strategy before making a business decision?

Every decision you make needs to be backed by strategy infused with intuition. Your gut feeling counts for a lot.  As a startup founder, we're always acutely aware of what our bottom line is and that trends come and go with the slightest breeze. With a business model based on cyclical events and seasons, it's a risky move to invest your life's work in a niche instead of a broader industry. Because of the risk, it's critical to understand tipping points and analytics models (what's converting and what's not).


What do you think sets you apart from other competitors?

Rad Season is known for being the world’s first one-stop-shop for all your action sports and adventure festival booking needs, backed by Priceline. Prior to the launch of Rad Season, no such resource bringing event calendars, adventure festivals, and travel booking together in one place was in existence. Despite a super crowded travel market generating $683 billion in 2016 (a whopping 10 percent of the GDP), no one was focused on the niche catering to adventure travel, a $263 billion market, until Rad Season.

HOW WE STAND OUT: Say you’re exploring Southeast Asia in search of the sickest waves (as rad people do), and you keep hearing from people you meet about this awesome event they just went to, or a contest the next island over from you -- this is what you traveled halfway around the world for, but it seems like you’re always one step behind the action. HERE’S THE PROBLEM: there’s no one-stop-shop search engine for all your interests. Action sports and adventure travel information is very fragmented, not only among the various sports, but in how people obtain it -- across the web, print media, and word of mouth. If you get lucky and hear about an event in time, you still have to pull up multiple websites to work out all your travel details, accommodation, transport, and reviews. The process is a mess. HERE’S THE SOLUTION: Finding rad things to do shouldn't be this hard. Now it's not. Rad Season eliminates the click-work by integrating all these elements and making the planning process seamless.


How do you fend off or deal with those moments of doubt, that every entrepreneur struggles?

As entrepreneurs, we can create a laundry list of excuses and choose to buy into fear or we can choose to focus on the genius and magic that comes with bold risk. Do you want to look back on your life and think "I could have" or "I should have"? That feeling of knowing that you could have made a difference in the lives of others or created something truly innovative should be the driver of pursuing your dream. To stop fear in its tracks, I visualize my life and goal cast based on what my true desires are. Meditating on that thought; living and breathing it until each goal comes to fruition.

The other key element in fending off fear is acknowledging you can’t carry the torch alone. Leadership is often defined by strength, but leaders need to ask for help as much as the next person. Acknowledging that you don't have all the answers contributes to a humble learning culture that encourages growth and open communication across your organization. Leaders who seek mentorship and advisors have the ability to take their leadership and business to the next level. Don't tackle everything on your own. Know when to listen to your intuition and when to ask for mentorship.

What question do you think every entrepreneur should be asking themselves?

Every entrepreneur should check in with themselves often to keep a pulse on how they’re progressing, starting with naming their fears and confronting them head on. What scares you about failure? should be a regular question entrepreneurs ask of themselves as a way to acknowledge what’s potentially interfering with their progress. As Winston Churchill said, "Success is not final; failure is not fatal: It is the courage to continue that counts".



With your incredible experience in business development, what do you think small businesses should be doing to sustain their business, while innovating their industry?

Grow your community to create brand loyalty. Early on we put a team of highly talented contributors in place who helped build out Rad Season’s messaging, digital presence, and content marketing, which in this age of technology, will make or break your brand. Our team of content contributors (travel writers, bloggers, and photographers) have helped grow our online community by leaps and bounds, and served as Rad Season ambassadors across social media platforms and within the adventure travel community to increase brand awareness.


How did you navigate your way through a new country while building the only business of its kind in Sydney?

The excitement in moving to a new country while launching a business adventure and growth lie within the “rad hunting”. I refer to my work trips as rad hunting: field research by exploring the world for the best action sports and adventure the earth has to offer. My wife and I welcomed our first baby into the world earlier this year and I guess you could say we’re pretty unconventional since not long after the birth of our baby, we headed to New Zealand, Spain, Portugal, and Germany to “rad hunt” for six weeks … baby gear in tow.

What are your thoughts of bootstrapping or raising investment before launch?

Rad Season is a bootstrap startup for a few key reasons:

  • Bootstrapping keeps you humble and hungry.

  • Bootstrapping your startup keeps you in control of your vision while granting you the freedom to be selective about what partners you want to help you scale your business. Write your own story.

  • Resilience and creativity: bootstrapping forces you to get creative about solutions, projects, and outsourcing. It’s amazing what lessons you learn without a safety net.


What plans do you have for Rad Season over the coming 12 months?

My focus is on rolling out the next phase of Rad Season’s business model. I can’t share much since we lead the pack in the adventure travel space but the drawing board is full and we’ve got some talented people on board to help propel Rad Season to the next level.

Whether it's a snowboarding music festival in the Australian Alps in April, a surfing contest in Hawaii in December, or a camel riding race in the Outback in July, this all sets the stage for Rad Season's notion that it's always the season somewhere...