RIDING WITH KAPLAN Podcast

Jonathan E. Kaplan
  • 5.0 (32)
  • Sports
  • Updated Daily

The podcast, RIDING WITH KAPLAN, dives deeper into the intersection of professional cycling and media, business, culture, and politics. ridingwithkaplan.substack.com

  1. Jul 13

    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 Check out a conversation between Reed and his chatbot, Arnold. Follow Reed on X Follow Reed on LinkedIn Get full access to RIDING WITH KAPLAN at ridingwithkaplan.substack.com/subscribe

    REED ALBERGOTTI TOLD ME NOT TO USE AN AI CHATBOT AS A COACH. THEN HE BUILT ONE.

  2. Jun 30

    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

    TOUR de FRANCE FOR BEGINNERS

  3. Jun 23

    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 Cycling Weekly You can find Dan on Instagram and LinkedIn. Get full access to RIDING WITH KAPLAN at ridingwithkaplan.substack.com/subscribe

    CYCLING'S EMERGING POWERS

  4. Jun 17

    HOW SOCCER + CYCLING EXPLAIN THE WORLD

    The World Cup is underway. And if you’re looking for someone who saw all of this coming — the sovereign wealth funds buying clubs, the exorbitant costs of fandom, the collision of soccer and authoritarian soft power — Franklin Foer did. Twenty-two years ago. Foer is a national correspondent at The Atlantic, a former editor of The New Republic, and the author of How Soccer Explains the World — a book that used the game as a lens to dissect the forces of globalization long before most American sports writers thought soccer was worth covering. He also is the author of World Without Mind, about Big Tech’s takeover of culture, and The Last Politician, about Joe Biden. Today we talk about what the book got right, what it missed, what Trump and FIFA have in common, and why the World Cup — more than any other sporting event — is a Rorschach test for the world we actually live in. Of course, there’s a cycling angle. Subscribe to RIDING WITH: Follow Jonathan on LinkedIn: https://www.linkedin.com/in/jonathanekaplan/ Follow Jonathan on Instagram: https://www.instagram.com/jonny99kaplan Buy “How Soccer Explains the World: An Unlikely Theory of Globalization” https://a.co/d/01OOqZ6U Get full access to RIDING WITH KAPLAN at ridingwithkaplan.substack.com/subscribe

    HOW SOCCER + CYCLING EXPLAIN THE WORLD

  5. 09/25/2025

    SPORTSWASHING: RWANDA HOSTS CYCLING'S WORLD CHAMPIONSHIPS AMID ALLEGATIONS OF HUMAN RIGHTS VIOLATIONS

    With cycling’s World Championships underway in Kigali, Rwanda, this week, I spoke with my old friend, Mvemba Dizolele, a highly-regarded foreign policy analyst, about the role of sports in diplomacy and politics. (Take the time to read Mvemba’s full bio here.) For background on the issues facing Rwanda, Minky Worden of Human Rights Watch, who is a friend of the RIDING WITH podcast, has a terrific dispatch about Rwanda’s human rights violations and the role it plays in the conflicts in Congo and Sudan. John Prendergast, a leading human rights advocate who has worked for decades to cast light on genocide and conflict, has this piece in Foreign Policy about how Rwanda has used sports partnerships to enhance its reputation in global politics. Dizolele offers listeners a quick history of Rwanda, how the country fits into today’s geopolitics, and how consumers and companies can alter the behavior and policies of countries seeking the benefits of hosting prestigious sporting events like cycling’s World Championships. Get full access to RIDING WITH KAPLAN at ridingwithkaplan.substack.com/subscribe

    SPORTSWASHING: RWANDA HOSTS CYCLING'S WORLD CHAMPIONSHIPS AMID ALLEGATIONS OF HUMAN RIGHTS VIOLATIONS

  6. 09/08/2025

    BEHIND THE SCENES AT THE MARYLAND CYCLING CLASSIC

    Today’s episode of the RIDING WITH podcast is a bit different. I’m trying a narrative with sound mixed in from the biggest, most prestigious cycling race in the United States, which took place in Baltimore on Sept. 6, 2025. You’ll get to hear from the winners, runners-up, and those finishing just off the pace. It’s an inside look at what it takes to produce a massive event in a major American city from race organizers to the mayor’s office, and how the riders themselves view Baltimore and the United States. Get full access to RIDING WITH KAPLAN at ridingwithkaplan.substack.com/subscribe

    BEHIND THE SCENES AT THE MARYLAND CYCLING CLASSIC

  7. 07/16/2025

    BEING THERE

    At the Tour de France, the teams’ buses are equipped with laundry machines. Hotels can range from high end to a box and a cardboard mattress. After crossing the finish line on the Champs-Élysées, the riders celebrate with family and friends, attend a fancy team dinner, and then go clubbing. On today’s podcast, I speak with Kevin Vermaerke, a 24-year-old American professional cyclist, riding for the Dutch team, Picnic PostNL. Vermaerke raced the Tour de France in 2022, but he crashed on Stage 8 and was forced to abandon the race with a broken collarbone. One moment you’re racing in front of thousands of screaming fans, the next you’re sitting in the quiet of a hospital in rural France. But Vermaerke came back the next year and finished the race; he finished the Giro d’Italia in 2024. We talk about going to the Tour, being at the Tour, and leaving the Tour. We also discuss Visma Lease a Bike’s strategy on Stage 10 at this year’s Tour de France, the end of Netflix’s series, Unchained, and book recommendations. I’m also going to have to buy a new pair or two of cycling shoes. Thanks for reading and listening. Please subscribe and share. SHOW NOTES: Fear and Loathing at the Tour de France with Kevin Vermaerke The Finish Line (Vermaerke’s interview is at the 37th minute) LOVE, ACTUALLY. AND TRAVEL LOGISTICS, VISA APPLICATIONS, AND CONCUSSION PROTOCOLS with Rindi Kessler Book recommendations: Challenger: A True Story of Heroism and Disaster on the Edge of Space by Adam Higginbotham Presumed Guilty by Scott Turow The Wide Wide Sea: Imperial Ambition, First Contact and the Fateful Final Voyage of Captain James Cook by Hampton Sides Flow: The Psychology of Optimal Experience by Mihaly Csikszentmihalyi 40% DISCOUNT - JULY ONLY Get full access to RIDING WITH KAPLAN at ridingwithkaplan.substack.com/subscribe

    BEING THERE

  8. 07/05/2025

    ORLA CHENNAOUI ON CYCLING, JOURNALISM, and the CHANGING MEDIA LANDSCAPE

    Orla Chennaoui didn’t just rise through the ranks of sports media — she cut her own path. From reading traffic reports and covering sports for Sky News to anchoring coverage of cycling’s biggest races, she’s now the voice of cycling on TNT Sports and a defining presence in the sport. While TNT Sports airs in the UK and Ireland, cycling fans in the United States who subscribe to MAX (formerly HBO) can watch her pre- and post-race coverage of some of cycling’s biggest races. Today, Chennaoui is more than a journalist — she’s a global brand. She frequently engages with her audience on social media — she has more than 125,000 followers alone on Instagram — where she chronicles her life as mother, journalist, and health, fitness, and wellness advocate. She’s an advocate for people, especially women, battling depression, anxiety, and addiction. Our conversation focuses on her career in journalism, why she loves covering cycling, and her predictions for who will win the 2025 Tour de France. You can follow Chennaoui on Instagram | YouTube | Ten Times Braver. Get full access to RIDING WITH KAPLAN at ridingwithkaplan.substack.com/subscribe

    ORLA CHENNAOUI ON CYCLING, JOURNALISM, and the CHANGING MEDIA LANDSCAPE
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About

The podcast, RIDING WITH KAPLAN, dives deeper into the intersection of professional cycling and media, business, culture, and politics. ridingwithkaplan.substack.com

Information

  • Creator
    Jonathan E. Kaplan
  • Years Active
    2023 - 2026
  • Episodes
    45
  • Rating
    Explicit
  • Copyright
    © Jonathan E. Kaplan
  • Show Website
    RIDING WITH KAPLAN Podcast