Side B Dialogues

Jimena Santillán

Hosted by Jimena Santillan and Veronica Diaz, The Side B reveals the human stories behind career success. Through honest conversations with professionals from all industries and backgrounds, we explore how they got there, the risks they took, and the lessons they learned along the way. Real journeys, real talk — to inspire those building or redefining their own path.

  1. 1d ago

    Hernán Casciari: "El mejor infarto de mi vida" | El hombre que hizo llorar a Messi

    ¿Qué hace que un escritor conecte tan hondo con la gente que hasta un ídolo mundial termina llamándolo por teléfono… llorando? En este episodio nos sentamos con Hernán Casciari, uno de los narradores más queridos de la lengua española, para entender de dónde sale su forma tan única de contar historias.Hablamos de su infancia en un pueblo de provincia, de lo que significa emigrar (y volver), del oficio de narrar, de un momento que le partió la vida en dos y de las decisiones que lo llevaron a hacerlo todo a su manera. Una conversación íntima, honesta y profundamente humana, con historias que vas a querer volver a escuchar.🎧 Suscribite y activá la campanita para no perderte los próximos episodios.💬 Contanos en los comentarios cuál fue el momento que más te tocó.⏱️ CAPÍTULOS:00:00 – Quién es Hernán Casciari01:05 – Crecer en Mercedes: militares, jueces y curas04:05 – Leer para ver otros mundos07:05 – El día que descubrió su oficio (tenis y Sherlock Holmes)13:21 – Cruzar el océano por amor: el aeropuerto que lo cambió todo17:39 – El lado oculto de emigrar y el "inmigrante invisible"22:58 – La mentira que lo hizo famoso: ficción en internet antes que nadie26:55 – Qué es Orsai y por qué la gente llora con sus cuentos30:38 – Escribir vs. interpretar: meterte imágenes en la cabeza33:14 – "El mejor infarto de mi vida"37:35 – Siete años sin poder escribir40:04 – Envejecer con curiosidad: "me interesa ver cómo me caigo"42:21 – La historia que hizo llorar a Messi47:21 – Qué nos pasa los argentinos con Messi50:00 – Lo que más extraña: el cielo y el horizonte argentino53:09 – "En tu lugar hablás de verdad"57:19 – Lo que hoy le da paz1:00:39 – Cómo le gustaría que lo recuerden1:01:09 – Ronda rápida#HernánCasciari #Orsai #Messi

    1h 18m
  2. May 25

    He Got Into Oxford Medicine. Then He Walked Away. | Chuk Okpalugo

    What does it take to walk away from Oxford Medicine, Wall Street, and one of the most respected stablecoin companies in the world?It's not ambition. It's not money. It's not even bravery.It's something quieter. Something most people will never understand.In this episode, Chuk Okpalugo — known on LinkedIn as "Mr. Stablecoins" — shares the conversations behind the resume. The doubts. The micro-decisions. The mentor who told him stop trying to look smart in front of his engineers. The moment he realized that prestige wasn't a destination — it was a door.We go deep on:▸ The "noble gambling" theory of entrepreneurship — why founders are addicted to the highs and lows▸ Why he believes prestige is the most misunderstood word in career advice▸ The truth about Oxford that no one tells you (and why he left after 2 years)▸ How four years in finance prepared him for FinTech — and the salary cut nobody talks about▸ The day he discovered stablecoins — and why he calls them "internet rails for money"▸ The leadership mistake that cost him his team's trust early on▸ Why he resisted building a personal brand for a decade — and what changed his mind▸ The "99 No's" rule that rewired how he handles rejection▸ How AI is creating a once-in-a-generation shift in personal agency▸ Why compounding is the most underrated force in any career▸ The Naval philosophy that quietly shaped everything he's done since 2020This isn't a stablecoin masterclass. It isn't a career playbook.It's an honest conversation about what happens when you stop optimizing for what looks right — and start building what is right for you.⏱️ CHAPTERS00:00 — Intro03:44 — A Nigerian household in Manchester05:35 — The Olympic athlete in the family09:01 — "I had no idea what I wanted to be"10:24 — Entrepreneurship as "noble gambling"14:13 — Why founders can't stop building17:18 — The real reason he chose Oxford Medicine22:00 — Prestige is a door, not a destination23:41 — Walking away after 2 years29:50 — Morgan Stanley, Silver Lake, Harvard31:31 — Joining an 11-person startup36:44 — How finance prepared him for FinTech40:34 — Discovering product management by accident46:46 — "Money is broken" — the stablecoin awakening48:48 — Inside Paxos50:39 — Zero-to-one vs scaling51:08 — The micromanaging mistake52:29 — Why he finally built his own voice57:05 — "You can just do things"1:00:28 — The compounding nobody sees1:03:31 — The 99 No's rule1:05:29 — Quickfire round—ABOUT CHUK OKPALUGOFormer Morgan Stanley, Silver Lake, Harvard Business School, EquityZen, and Paxos. Today, one of the most followed voices in FinTech and stablecoins on LinkedIn — writing, advising, and building independently. His focus: stablecoins, payments, and the future of money.Follow Chuk on LinkedIn: [link]—🎙️ SIDE BEAT DIALOGUESThe podcast for the ones who don't follow the script.Hosted by Jimena & Veronica.Subscribe and 🔔 turn on notifications — new episodes weekly.—#ChukOkpalugo #Stablecoins #FinTech #Podcast #Crypto #Paxos #PersonalBrand #CareerChange #AI #ProductManagement #Entrepreneurship #FutureOfMoney #Oxford #HarvardBusinessSchool #SideBeatDialogues

    1h 9m

About

Hosted by Jimena Santillan and Veronica Diaz, The Side B reveals the human stories behind career success. Through honest conversations with professionals from all industries and backgrounds, we explore how they got there, the risks they took, and the lessons they learned along the way. Real journeys, real talk — to inspire those building or redefining their own path.