Massimiliano "Masi" Ambrosi is South Africa's 2025 Under-23 XCO Champion, a privateer

racing the UCI World Cup circuit on pure belief and a support structure built from scratch.

In this conversation, he walks us through the full arc: growing up in Johannesburg on

motorbikes, the deal his dad made with him to keep his school average above 75% or lose

the bike, seven years with Trek from a borrowed top fuel to a direct contract with Trek

Europe, and what it actually costs — logistically, mentally, physically — to show up at Les Gets or Andorra against the factory riders of the world.

# === CHAPTERS ===================================

# === LISTEN ON THE GO ===========================

Spotify: https://open.spotify.com/show/5GselFmeym7YgYXtcyPUXU

Apple Podcasts: https://podcasts.apple.com/us/podcast/active-hobo/id1846864699

# === FOLLOW ACTIVE HOBO =========================

Subscribe: https://youtube.com/@activehobo?sub_confirmation=1

Website: https://activehobo.com/

Instagram: @theactivehobo

Strava: https://strava.app.link/ciVbx92FJ2b

# === THE CREW ===================================

Dave @davlewjenkins

# === MORE FROM ACTIVE HOBO ======================

Latest episode: https://youtu.be/VRIeP2JYf5U

Full podcast playlist: https://www.youtube.com/playlist?list=PLc2XIoaiAXafwoZykJM-jg6HnrLkWlJXH

Related episode: https://youtu.be/lGfvanjllXY

# === WORK WITH US ===============================

Sponsorships & collabs: david@activehobo.com

Send a question for the show: noah@activehobo.com

#ActiveHobo #CyclingPodcast #SouthAfricanCycling

Join David Jenkins and Orphan Street Clothing Shop founder Matt Kieser for a wide-ranging conversation about what it actually takes to build a third space in a sport that already has plenty of bike shops. They go deep on the OSCS story — from its Orphan Street origins through the move to Sea Point — the cycling community that grew up around it, Thursday rides and Cape Town Cycle Tour traditions, the global Pas Normal Studios partner summits in Barcelona, Mallorca, and Copenhagen, and why people will save up for three months to buy a single jersey and wear it every ride of the week.

They also get into the beautiful collision happening in Cape Town right now: Strava rivals who have been chasing each other's segments for fifteen years, finally sitting down at the same coffee table and shaking hands for the first time.

Who is Matt Kieser?

Founder of Orphan Street Clothing Shop (OSCS), Sea Point, Cape Town — South Africa's home for Pas Normal Studios cycling apparel and one of the city's most beloved community cycling hubs.

What is Pas Normal Studios?

A Copenhagen-based cycling apparel brand founded in 2014 by Karl-Oskar Olsen, Peter Madsen, Tommy Pedersen, and Brian Nygaard. "Pas normal" means "not normal" in French — which is exactly what the brand set out to be.

# === CHAPTERS ===================================

0:00:00 — Matt Kieser: The Man Behind OSCS

0:01:37 — David's First Ride With Matt: Cape Town Cycle Tour Eve

0:04:00 — The Pas Normal Studios Perception Problem

0:07:00 — What Really Happens When You Show Up to a Thursday Ride

0:13:00 — How Matt Got Into Cycling (And Down the Rabbit Hole He Can't Escape)

0:23:00 — The Hong Kong Jersey That Started Everything

0:25:00 — How OSCS Became a Pas Normal Studios Stockist

0:31:00 — What Happens at the Annual Pas Normal Brand Summit

0:36:00 — Is Premium Cycling Kit Worth the Price? An Honest Conversation

0:51:00 — The Fashion World Meets Cycling: Kim Jones, Orphan Street, and Virgil Abloh

0:53:00 — Building a Community Space, Not Just a Shop

1:05:00 — The Coffee Problem (and How Ali Solved It)

1:05:51 — Moving to Sea Point: What Changed

1:13:00 — Strava Rivals Who've Never Met — Until Now

1:28:20 — Closing: What Comes Next for OSCS

# === LISTEN ON THE GO ===========================

Spotify: https://open.spotify.com/show/5GselFmeym7YgYXtcyPUXU

Apple Podcasts: https://podcasts.apple.com/us/podcast/active-hobo/id1846864699

# === FOLLOW ACTIVE HOBO =========================

Subscribe: https://youtube.com/@activehobo?sub_confirmation=1

Website: https://activehobo.com/

Instagram: @theactivehobo

Strava: https://strava.app.link/ciVbx92FJ2b

# === THE CREW ===================================

Dave @davlewjenkins

# === MORE FROM ACTIVE HOBO ======================

Latest episode: https://youtu.be/VRIeP2JYf5U

Full podcast playlist: https://www.youtube.com/playlist?list=PLc2XIoaiAXafwoZykJM-jg6HnrLkWlJXH

Related episode: https://youtu.be/lGfvanjllXY

# === WORK WITH US ===============================

Sponsorships & collabs: david@activehobo.com

Send a question for the show: noah@activehobo.com

#ActiveHobo #CyclingPodcast #SouthAfricanCycling

Garden Route Giro, the race that's been years in the making, finally happened — and we rode every stage.

Mossel Bay to Wilderness. Six days. Nearly 700 kilometres through mountain passes, Klein Karoo desert, and some of the most staggering gravel road on earth. We raced it, we filmed it, and we got humbled by it. This episode is the full debrief — what the racing felt like from inside the peloton, what we got right on the media side, what we'd do differently, and why Dryland have built something this country has genuinely needed.

But this weekend wasn't just about South Africa. Paul Seixas is 19 years old and he nearly broke Tadej Pogačar. Sabastian Sawe ran a sub-two-hour marathon in a sanctioned race for the first time in human history. And someone ran the entire London Marathon with a 25kg fridge on their back — for his mum.

Big week. Here's all of it.

# === CHAPTERS ===================================

0:00 — Back to the roots with Dave and Alec

1:38 — Garden Route Giro from inside the race

8:00 — What Dryland got right with race media

13:10 — Favourite moments, hard stages and riders going too deep

17:00 — The elite racing, women’s field and why the event felt serious

23:45 — Gravel bike chaos and setup debates

26:20 — Pogačar, Liège-Bastogne-Liège and the Paul Seixas moment

32:45 — London Marathon, super shoes and impossible speeds

44:00 — Wheelchair racing, robot marathons and strange endurance stories

50:00 — Alan Hatherly, the Giro d’Italia and what comes next

53:30 — Gattas, gravel bikes and upcoming races

# === LISTEN ON THE GO ===========================

Spotify: https://open.spotify.com/show/5GselFmeym7YgYXtcyPUXU

Apple Podcasts: https://podcasts.apple.com/us/podcast/active-hobo/id1846864699

# === FOLLOW THE BREAKAWAY =======================

Subscribe: https://youtube.com/@activehobo?sub_confirmation=1

Website: https://activehobo.com/

Instagram: @theactivehobo

Strava: https://strava.app.link/ciVbx92FJ2b

# === THE CREW ===================================

Dave @davlewjenkins

Alec @alec.gates

# === MORE FROM THE ACTIVE HOBO ====================

Latest episode: https://youtu.be/VRIeP2JYf5U

Full podcast playlist: https://www.youtube.com/playlist?list=PLc2XIoaiAXafwoZykJM-jg6HnrLkWlJXH

# === WORK WITH US ===============================

Sponsorships & collabs: david@activehobo.com

Send a question for show: noah@activehobo.com

# Like, subscribe, and share with someone who

# needs to hear that endurance sport is never just about the strongest legs.

#TheBreakaway #CyclingPodcast #SouthAfricanCycling #GardenRouteGiro #Pogacar #LondonMarathon