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. 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
  2. Apr 14

    Nadie te enseñó esto sobre el dinero (y necesitas saberlo) | Nieves Villena

    ¿Cuántas veces has escuchado que el dinero no da la felicidad… pero aun así sientes estrés, culpa o miedo cuando piensas en él?👉 En este episodio de Side B Dialogues, hablamos con Nieves Villena, psiconomista, coach y autora de 29 días para conectar con tu felicidad económica, sobre algo que nadie nos enseña:cómo relacionarnos con el dinero de forma sana.Porque el problema no es solo cuánto ganas…👉 es lo que piensas, sientes y haces con el dinero.💡 En este episodio descubrirás:Por qué el dinero sigue siendo un tema tabúCómo tu infancia y tu entorno afectan tu relación con el dineroPor qué muchas personas sienten culpa al gastarCómo empezar a ahorrar sin ansiedadQué hay detrás del miedo a emprenderPor qué no necesitas ser experto para ordenar tus finanzasCómo encontrar tu propio sistema (y dejar de copiar a otros)La verdad sobre la educación financiera que nadie te cuenta🔥 Una historia realNieves dejó una carrera estable en banca…y pasó 2 años sin generar ingresos construyendo su proyecto.Un camino lleno de incertidumbre, aprendizaje y crecimiento que refleja una realidad que pocos cuentan sobre el emprendimiento.🎙️ Sobre la invitadaNieves Villena es psiconomista, coach y experta en bienestar financiero.Su trabajo une economía + psicología para ayudar a las personas a mejorar su relación con el dinero desde dentro.👇 Cuéntanos en comentarios:¿Te enseñaron en casa a gestionar el dinero?🔔 Suscríbete para más conversaciones reales sobre:finanzas, carrera, emprendimiento y crecimiento personal#SideBDialogues #EducacionFinanciera #FinanzasPersonales #Dinero #MentalidadFinanciera #Podcast #Emprendimiento #CrecimientoPersonal #BienestarFinanciero

    1h 1m

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.