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The Rolling Around Story

By Carlo Pizzuti, founder of Rolling Around

What started as a simple search for a long winter escape, became a journey from California to Mexico, and the beginning of Rolling Around.

A simple quest to escape winter evolved into a California-to-Mexico journey and the birth of Rolling Around.

The Spark

It started with an idea

2022

The journey began in the winter of 2022 in London, when casual research into long-distance cycling sparked the idea of riding the Panamericana not by van, but by bicycle, from Alaska to Patagonia.

This was my commuter bike after a snowy night in the winter of 2022

First Attempt

In February 2023 came the first overnighter.No panniers. No tent. Just a bike, a backpack, and a cold night in the forest. It wasn’t comfortable, but it proved the idea was possible.

The Big Challenge

A month later, the GB Divide followed: 18 days of bikepacking across Great Britain. The hardest thing I’ve ever done. Still, I wasn’t put off.

The Journey South

As it was too late in the year to start in Alaska, I flew to San Francisco and began cycling and surfing down the Pacific Coast. The landscapes were unreal. The people lovely. Then came the Baja Divide.

The Turning Point

While struggling to cycle on rough terrain, one thought kept coming back: “Why is there no app that shows what the road ahead looks like?” Cyclists constantly guess terrain, conditions, and difficulty. Some enjoy the uncertainty but others want to choose. That was the moment the seed for Rolling Around was planted.

When the Ride Stopped

Looking ahead

As beautiful as the journey was, something was missing. Months in a tent and limited social connection took a toll on me. I packed up and returned to London, carrying one thing with me: an idea worth building.

From Idea to Product

In March 2024, I shared the idea in cycling groups. Feedback was encouraging.

The idea evolved from a simple “street view” concept into a broader platform.

A landing page followed. Positive feedback kept coming. It was time to turn the idea into a product. The problem? I did not know from where to start. The app was a simple flowchart. I honestly thought it would be “four screens.” Today, Rolling Around has 400+ screens.

Building the Team

After dozens of quotes and dead ends, I found Vipul on Upwork, now CTO and close friend. Without him and his team, Rolling Around wouldn’t exist. I also learned, the hard way, that apps need proper UI/UX. That led to Ivan, who created the logo and visual foundation. By September 2024, the app was ready for testing.

The Process That Shaped Everything

Feedback → Code → Test → Repeat

That loop, run dozens of times, is the reason Rolling Around looks and works the way it does today.

Growing Through Community

There was no gorilla marketing. The goal wasn’t downloads, it was usefulness.

Rolling Around was shared in cycling groups, one helpful answer at a time. It slowly became the “the iOverlander for cycle touring.”

In February 2025, with just 164 users, Max joined the journey. Tester. Ambassador. Community product manager. All unpaid, just the love for the project. No one has contributed to Rolling Around as much as him. Thanks, Max!

What Rolling Around Stands For

Community-based knowledge
Transparency and data ownership
A Waypoints Map that is free, forever

Delete your account, and your data (including waypoints) leaves with you.

Rolling Around holds nothing and never sells your data for marketing purposes!

Gratitude

Rolling Around exists because of its people, early supporters, testers, designers, developers, and hundreds of contributors adding real value to the map every day. This is not a solo project. It never was.

Read the Full Story

This page is the short version

If you’d like every detail, the full journey, names, dates, lessons, and behind-the-scenes moments, you can read the complete story.