Episode 154: Robbie Danger Webb

The first openly trans person to cycle around the world

When I sat down with Robbie Danger Webb, I already knew they had an incredible story. I’d been following their posts for months and loved how they shared the real parts of long-distance cycling. Not just the ‘summits and sunshine,’instagram perfect’ parts, but also the tougher days too. In May, 2025 Robbie successfully completed a full circumnavigation of the world, becoming the first openly trans person to do so, and I wanted to go right back to the beginning to understand how it all came together for them.

From Push Scooters to Bikepacking

Robbie didn’t grow up as a “bike kid.” In fact, one of their earliest memories is doing a school triathlon while running around a grass field carrying a push scooter, because they didn’t yet know how to ride. Cycling didn’t ‘click’ until their early twenties, when climate concerns, daily walking and watching other people ride pushed them to think, well, if they can ride a bike, why can’t I?

That thought opened a door. Commuting turned into exploring. Exploring turned into bikepacking. Pretty quickly, Robbie was looking for their first big challenge.

Building a Bike in Two Days and Riding 3,000 km

Only a year or so after getting into bikepacking, Robbie signed up for the Tour Aotearoa, New Zealand’s 3,000 km brevet that traverses the full length of the North and South Islands of the country. Most people would obsess over bike choices for months before taking on the toure. Robbie built their bike themselves in just two days. The bike lasted and it also still works!

That ride was a turning point for them. While many riders reached the finish line ready to head home, Robbie felt something else entirely. They didn’t want the experience to end. Bikepacking had revealed a new way of seeing the world, and suddenly travel which is something they hadn’t been drawn to before, started to become really appealing.

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Genesis of the World Record Ride

But it’s a long way from riding the length of New Zealand to deciding to ride around the world. I really wanted to understand how it was that Robbie came up with this idea. For that we need to go back to COVID lockdowns in New Zealand. Borders closed. Life paused. Robbie found themselves wondering what to do next. They had always had a small thought in the back of their mind about cycling around the world, but now that idea had space to grow.

Out of curiosity, Robbie checked whether there was a Guinness World Record for the first transgender person to circumnavigate the world by bike. There was. And nobody had claimed it yet.

Seeing that record listed sparked something immediate. As Robbie put it, “it felt like a sign. That’s for me”.

Planning, Packing and Leaving Life Behind

Planning a world record ride is no small thing. Robbie had to design their entire route, submit everything to Guinness, quit their job and pack up their whole life. They also budgeted incredibly carefully, living very simply and stretching every dollar. Their final average cost was just 40 cents per kilometre.

Robbie wanted to change their life and they also saw the world record as a way of facilitating that. They wanted more community, especially queer community, and hoped that this massive journey might help them find it.

Getting Hit by a Car and Choosing to Continue

Just 3,500 km into the ride, Robbie was hit by a car in Iowa. For most people, that would be the end. But Robbie insisted on being taken to the bike shop first, despite blood running down their face. The bike needed attention before anything else. Only then did they go to hospital for stitches and concussion checks. Quitting didn’t cross their mind once because restarting the ride all over again would have been far harder for Robbie to do than continuing.

Travelling the World as an Openly Trans Cyclist

Travelling by bike already puts you in a vulnerable position. Travelling as an openly trans person adds a layer most people never have to think about. Robbie had to navigate countries where political tensions were rising, or where new anti-LGBTQ laws came into effect literally the day before they arrived.

Because Guinness requires daily witness signatures, Robbie often had to out themselves as being trans, to complete strangers. In some regions, that wasn’t straightforward or safe and we talk candidly about how Robbie navigated their way through this.

In so many previous podcast interviews, guests will tell me how the overwhelming kindness afforded to them by complete strangers, blows them away. And this was very much the case for Robbie as well. They were welcomed into homes. Fed by strangers. Hosted by queer people around the world who reached out. Many people had simply never met a trans person before and were curious, warm and supportive.

Finding Community in the Unlikeliest Places

Robbie said they met people around the world who felt like them. People they connected with instantly. Robbie indeed, found the community they were seeking out. The more they rode, the more they realised that they could find community anywhere. Even in places they never expected.

And that’s also the magic of bike travel. It’s the conversations at petrol stations. The people who wave you down to ask where you’re going. The families who bring you inside for tea. The tiny towns you’d never visit if not for riding through it on your bike.

Robbie also highlighted that their experience was also an example of where Social Media can actually be a good thing, helping to connect you with others in your community from around the world.

A Message for Others Who Feel Like Adventure Isn’t Accessible to Them

Robbie knows that for many queer or trans people, big adventures can seem out of reach. And it’s true that there are extra considerations, risks and at times safety precautions to take seriously.

But Robbie’s experience shows that it is also possible. That the world is not as scary as it often looks on the internet. And that with preparation, awareness and community support, you can absolutely do something bold like cycle around the world.

Robbie is now going through the process of having their world record ride officially recognised. With all the administration involved it’s actually something which in ways is more challenging than the ride itself!

I’m certain that more adventures lay ahead of them, so be sure to give them a follow on their instagram account, to check out their future adventures. @DirtDropRobbie

The Seek Travel Ride podcast