About Riding With: A Podcast by Jonathan E. Kaplan
The podcast, RIDING WITH KAPLAN, dives deeper into the intersection of professional cycling and media, business, culture, and politics.
ridingwithkaplan.substack.com (https://ridingwithkaplan.substack.com?utm_medium=podcast)
REED ALBERGOTTI TOLD ME NOT TO USE AN AI CHATBOT AS A COACH. THEN HE BUILT ONE.
Reed Albergotti covers tech and AI for Semafor — and before that, he co-wrote Wheelmen, the definitive book on Lance Armstrong and cycling’s doping era. When I interviewed him last summer about AI coaching, his advice was blunt: don’t let ChatGPT or Claude train you. Hire a human.
A year later, he changed his mind. Reed built his own AI personal trainer — he calls it Arnold — that reads his smart scale, tracks his diet, checks his calendar, and adjusts his workouts around travel and how he’s feeling that day. We dive into what changed in tools like Claude Cowork and Codex, how a self-described non-coder builds real software now, and why we’re all about to become app developers without realizing it.
Reed also owns up to waking up to a $500 OpenAI bill and tells the story of Semafor Intelligence — the AI tool he prototyped in an hour that became a real product (and created a job).
Plus: Tour de France talk. Pronunciation struggles, podium picks, and Tadej Pogačar’s absurd dominance. Whether you’re a proponent or skeptic of AI, or just AI-curious, this episode is for you.
Show notes should include:
Reed’s latest in Semafor: AI makes mistakes, too (https://www.semafor.com/article/07/08/2026/ai-makes-mistakes-too)
Check out a conversation (https://drive.google.com/file/d/16Bv87046YrIxMREqt4pOnM1GHVvZePBp/view?usp=drive_link) between Reed and his chatbot, Arnold.
Follow Reed on X (https://x.com/reedalbergotti)
Follow Reed on LinkedIn (https://www.linkedin.com/in/reedalbergotti/)
Get full access to RIDING WITH KAPLAN at ridingwithkaplan.substack.com/subscribe (https://ridingwithkaplan.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4)
30 Jun 2026
TOUR de FRANCE FOR BEGINNERS
Last year, my family and I watched the final stage of the Tour de France with a friend of ours who is an accomplished academic and advocate. Her PhD thesis, which she wrote in 2016, predicted that we would be working from home – and the catalyst for that change would be an existential event, such as a pandemic.
So when our friend started asking questions about the Tour de France, I found myself struggling to explain basic parts of the race. I’ve been watching cycling for at least thirty years – is the sport and the race really that inaccessible? Or is it just me?
Two of the sharpest professional cycling analysts and, my friends, Andrew Vontz and Spencer Martin of the Beyond the Peloton podcast, are here to break down the basics of race so that you can tune in and not zone out; so that you can watch the action and understand the commentary; and enjoy the Tour as it moves through Spain and into France.
Wait, the Tour de France starts in Spain?
Get full access to RIDING WITH KAPLAN at ridingwithkaplan.substack.com/subscribe (https://ridingwithkaplan.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4)
23 Jun 2026
CYCLING'S EMERGING POWERS
Professional cycling calls itself a global sport, but its media coverage almost exclusively and not surprisingly focuses on Western Europe.
Dan Challis has taken a different approach. The journalist behind The Global Peloton – now at Escape Collective – joins the RIDING WITH podcast to talk about what it actually takes for a rider from Africa, Asia, or the Americas to break into the WorldTour — and why the formal pipelines that have worked in the past (Qhubeka in Africa, Androni and Colombia–Coldeportes in South America) keep collapsing rather than scaling.
Why has Japan, despite wealth and a massive cycling culture, never produced a WorldTour rider, and why India’s 2.5-million-spectator Pune Grand Tour might be the start of something real.
Of course, we cannot discuss these issues without diving into sportswashing and the financial chain reaction now destabilizing teams across the WorldTour, from Arkéa’s collapse to Movistar’s potential restructuring.
We revisit the Vuelta a España protests, talk about the future of cycling journalism, and make some bold Tour de France predictions.
Dan Challis
Escape Collective (https://escapecollective.com/author/dan/)
Cycling Weekly (https://www.cyclingweekly.com/author/dan-challis)
You can find Dan on Instagram (https://www.instagram.com/danchallis_globalpeloton?igsh=OHRxMDl5YzRjMmNq&utm_source=qr) and LinkedIn (https://www.linkedin.com/in/dan-challis-2362206b/).
Get full access to RIDING WITH KAPLAN at ridingwithkaplan.substack.com/subscribe (https://ridingwithkaplan.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4)
Who has been a guest on Riding With: A Podcast by Jonathan E. Kaplan
Names identified in recent episode analyses. Showing up to five guests.
Orla Chennaoui
Jacob Whitehead
Reed Albergotti
Spencer Martin
Andrew Vontz
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
Apple Podcasts (US)
5.0 / 5
32 ratings
Spotify
5.0 / 5
10 ratings
Podcast Authority Score: 51 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
70
Social presence
0
YouTube
0
Engagement
77
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