Oli Russell-Cowan

Often, innovation lives not in creating something new but refining something that already exists.

 

Oli Russell-Cowan created Rad Season,  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.

Where did the idea for Rad Season come from?

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 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 and at a certain point, I just had to find it.

Founded in April of 2016 on the Northern beaches of Sydney, Australia, Rad Season is an innovative website for finding and going to the best action sports and adventure events in the world. Rad Season is the one-stop-shop for helping you discover events, book event tickets, accommodation, travel and connect with others all on one site. And the name? Well, our mission is to lead you right to the radness. 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…

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

I get up at 4:30 am to spend half an hour prioritizing my day before heading out for a surf (if there are waves). After a morning surf, I drop my son, Theo, off at childcare before heading into the office. I start my morning by organizing my day into time blocks. By allocating designated time slots for each project and task on my ‘to-do’ list allows me to break away from the stress of upcoming or uncompleted tasks. Making the mental transition from managing ‘to-do’ lists to managing a calendar frees up my mind for increased productivity and creativity; a focus on cycles and creative bursts of work within time blocking clears distractions and allows me to unload the stress attached to an endless list of tasks.

How do you bring ideas to life?

Bringing an idea to life can be daunting, but to combat the “where to start” feeling, I put every idea through a three-step process:
-Discuss the idea with my advisors and mentors
-Lean into my intuition
-Research, plan, test- and go all in

What’s one trend that excites you?

Virtual Reality and how it is going to impact the Travel space is something I’m very excited about. Soon, you’ll be able to experience a virtual adventure in the most remote parts of the world to get a taste of what it will actually be like. Then you can plan your travel to experience it in real life.

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

I start my morning by organizing my day into time blocks. By allocating designated time slots for each project and task on my ‘to-do’ list allows me to break away from the stress of upcoming or uncompleted tasks. Making the mental transition from managing ‘to-do’ lists to managing a calendar frees up my mind for increased productivity and creativity; a focus on cycles and creative bursts of work within time blocking clears distractions and allows me to unload the stress attached to an endless list of tasks.

What advice would you give your younger self?

Don’t live a life that you’re not happy with. Reject the thoughts that tell you this is something you “have to do” because of society’s expectations.
-Follow your instinct
-Be open-minded
-Experiences, not things
-Work hard, have integrity

Tell us something that’s true that almost nobody agrees with you on?

England has some of the best surfing spots in Europe, if you know where to look.

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

I’m constantly checking in with myself to keep a pulse on how I’m progressing as an entrepreneur, starting with naming my 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”.

What is one strategy that has helped you grow your business?

Developing key partnerships. 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.

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

As the founder of a startup, entrepreneurship has taught me more than I could have possibly been prepared for. Jumping in too soon without having a plan was a big failure for me. Like in daily life, I could have easily used a laundry list of excuses to hide behind the fear and failure from that experience. But as Winston Churchill said, “Success is not final; failure is not fatal: It is the courage to continue that counts”. Failure is a complex social construct that we all experience in our personal and professional lives. To grow from failure, we must first be able to identify the types of failure: preventable, intelligence/ability, complex systems. Once you can identify the root of the failure, use its source to build resilience. That feeling of knowing that you can make a difference in the lives of others or created something truly innovative should be the driver of pushing your fear aside and pursuing your dream. Entrepreneurship is my personal Everest; you’re never fully prepared, but how fulfilling as you eventually make your way up in elevation.

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

Often, innovation lives not in creating something new but refining something that already exists. Look at older concepts in history and then improve upon it. For example, start a door-to-door milk delivery service (utilizing glass bottles to cut down on purchasing plastic bottled milk and waste). Our generation didn’t invent the “milk man” but we can make it better.

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

I recently purchased tickets for an upcoming Christmas. There’s no better time to celebrate the year that’s just gone by and get excited for what’s to come.

What is one piece of software or a web service that helps you be productive? How do you use it?

Early on in your startup journey, it’s critical to implement a project management system to keep your team on track for deadlines and goals. Trello is my project management system of choice as it provides a space for my team to communicate and brainstorm on their own autonomy while keeping me in the loop on their progress. Building out processes and using a system to track all pieces of your strategy will set you up for success.

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

Disrupted: My Misadventure in the Startup World by Dan Lyons is a pretty funny insight into the strange world of startups. A reminder that startup founders are human and we all experience failure.

What is your favorite quote?

“Success is not final; failure is not fatal: It is the courage to continue that counts.” — Winston S. Churchill

Key learnings:

• Often, innovation lives not in creating something new but refining something that already exists.
• Implement time blocking: making the mental transition from managing ‘to-do’ lists to managing a calendar frees up your mind for increased productivity and creativity; a focus on cycles and creative bursts of work within time blocking clears distractions and allows entrepreneurs to unload the stress attached to an endless list of tasks.
• Early on in your startup journey, it’s critical to implement a project management system and effective communications structure to keep your team on track for deadlines and goals.
• Read “Disrupted: My Misadventure in the Startup World” by Dan Lyons for a refreshing (and humorous) reminder on what all startup founders experience.

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