Communication, Connection, and Community on the Freedom Trail

As a business school professor, I often discuss and debate with my students whether it is

better for a small business to develop a deep, intimate connection with a few customers or to

spark awareness among a broad base of potential customers. While many small business

owners try to spark awareness with via a viral social media post, a wild publicity stunt, or an

expensive promotional campaign, most small business owners are better off developing fewer

but deeper connections, with a much narrower group of customers, and then fostering a

community around what they are doing. Freedom Challenge (FC) is an interesting case of

this.

As an FC dot watcher (i.e., spectator), going back to 2013 when my brother and sister-in-law

first participated in the Race Across South Africa (RASA) as their “honeymoon” to more

recently participating in FC events myself, I have been intrigued by the different modes of

communication that have been embraced to track riders and share their stories and

experiences from the trail. These communications have fostered a strong sense of connection

between FC stakeholders, including riders, buffalo herders (trail volunteers), dot watchers,

and hosts. And these connections have coalesced into a pretty special and robust community

of people who all care deeply about this incredible thing we call the Freedom Trail.

Communication

From what I can tell, the modes of communication between riders and others have evolved as

the event has developed. What started as pure dot watching with spectators being glued to a

computer screen, tracking a colorful dot moving imperceptibly slow along a digital map, to

the sharing of a few pictures and videos from the trail via text and a daily written report about

what happened on the trail from race office, has evolved into a more diverse, multichannel

communication strategy involving WhatsApp discussions, Facebook posts and Instagram

reels [Mark Zuckerberg should sponsor the event].

More recently, voice notes have also become integral to trail communication, first pioneered (I think) by Dr Sandy Inglis as he shared daily voice notes about his experiences on the trail in 2021, to the emotional voice note shared by Bruce Biccard about his experience of getting lost in Stettynskloof on the last night of the trail, while leading the race in 2022, and now the voice notes shared by Julia from race office on a daily basis to update us all on the happenings of the day during RASA.

The race office continues to have a robust, multipronged communication strategy, but one of

the wonderful new additions in 2025 is the_free_steve Instagram channel, where Steve

Johnston, a pretty regular, but very funny guy, from the Edenvale, shares his very real,

sometimes inspiring, and mostly hilarious posts about his RASA experience. These video

posts provide an excellent and very entertaining inside view of just how tough the Freedom

Trail is and how difficult it is to chase RASA cut-offs.

Connection

The diverse and varied forms of communication between those following the Freedom

Challenge create a unique sense of connection between dot watchers, riders, and others who

care about this event, even if they never meet face-to-face.

A few weeks back, on the day before Comrades, I connected with the Greves in

Pietermaritzburg for a quick catch-up. I had ridden the majority of RASA with Merak and

Ollie Greves (father and son) in 2021. The interesting thing about the catch-up was that I

spent almost all the time chatting with Ollie’s 84-year-old grandfather. We had never met

before, but he treated me like a long-lost friend and engaged with me as if he knew me. Not

because I am a very friendly person (I’m not), but because he had spent so many hours

watching my dot, looking at photos, and hearing reports from and about me as I rode RASA

with his grandson and son-in-law in 2021. The event had forged this connection.

In 2023, while participating in RASA, I arrived at Vuvu School late in the afternoon after a

strenuous day on the trail and was welcomed by the Graafs, who were riding in the Race to

Rhodes. We had never met in person or even chatted on the phone, but we greeted each other

like long-lost friends. This stemmed from all our interactions on the Freedom Challenge

communication channels. I felt like I knew them from their WhatsApp posts, Facebook

comments, and the general support they have provided to FC events over the years.

This year, nine days into the event, the_free_steve feels like a long-lost buddy from high

school. His posts are so relatable and real. If I ever bump into him at some other strip mall

pub on the East Rand, I will treat him like someone I have known for years. Beers on me (do

you get Devil’s Peak in Edenvale?).

This sense of connection extends to the Buffalo Herders, hosts, and all the other stakeholders

that are so integral to the trail.

Community

The implication of all these tight trail connections is that Freedom Challenge is much more

than just an event or series of events; it’s a community. One definition of community is “a

feeling of fellowship with others, as a result of sharing common attitudes, interests, and

goals.” FC connects people with similar attitudes, interests, and goals. In a world where it can

be quite difficult to find your tribe, Freedom Challenge unearths and connects people who

share a sense of adventure, an appreciation for the wild rural parts of South Africa, a desire to

get outside and take on big challenges, and a general belief in the goodness of people.

Whether it’s Craig Bosenberg engaging with FC all the way from Canada, or Rocket Ron

coming back time and time again to tackle an FC challenge and keep the dot watchers

entertained, or Hestelle packing delicious toasted sarmies with inspiring bike quotes on the

takeaway packets at Damsedrif, or the Buffalo Herders throwing boerewors on the braai at

Kudu Kaya or Jigs and Chris pulling out all the stops to keep riders moving along the

trail….this is one special community, let’s celebrate it.

So, would Freedom Challenge be better off if Netflix caught wind of this awesome event and

commissioned a blockbuster documentary about RASA? I think not. Some things are better

kept close and connected.