What if the stress, chaos, and hidden workload of managing your property while living abroad could be replaced with clarity, control, and peace of mind? In this episode, I sit down with Oscar Rubio, founder and CEO of Lodgering, a SaaS platform designed to solve one of the most emotionally taxing problems in real estate and mobility: managing a home from thousands of miles away.

Oscar shares the deeply personal journey that led him from overworked "one-man orchestra" to leading a scalable, global platform used by institutions, homeowners, and relocated professionals. We explore the messy realities of mobility—overbookings, lost bookings, endless emails, operational burnout, and stressful overseas incidents—and how Oscar transformed years of painful, unscalable work into a streamlined, AI-powered ecosystem designed to give every user what they truly want: safety, clarity, and peace of mind. This is a conversation about resilience, reinvention, and building a business that supports your life—not the other way around.

On This Episode

01:10 — The early days: visiting properties in person, doing everything manually, and learning relocation from the ground up 01:50 — Building multiple companies in Madrid… until COVID nearly shut everything down

02:23 — The turning point: digitizing every process into a scalable ecosystem—Lodgering 02:49 — Kyle introduces the idea of a multi-sided marketplace and asks Oscar how Lodgering works 03:14 — Oscar explains why Lodgering is a SaaS, not a marketplace—and why connecting platforms multiplies value 03:39 — Kyle frames Oscar's entrepreneurial journey as a story of scaling through repeated reinvention 04:11 — Oscar explains why experience is both "your enemy and your ally" when building a company 04:36 — Why resilience and learning from mistakes define long-term entrepreneurial growth

05:02 — Kyle asks about the real problems faced by Oscar's ideal clients 05:33 — Oscar describes hearing from CEOs: "you digitalized all our pains" 05:59 — Where the chaos really begins: managing 6+ booking platforms with no centralization 06:10 — The consequences: overbookings, underbookings, lost revenue, missed emails, and zero visibility 06:45 — Kyle presses for more specifics—and Oscar breaks down the true operational pain points 07:00 — Tenant issues, contracts, payments, incidents, and too many tools stitched together 08:00 — Why moving abroad is inherently stressful—and how Lodgering reduces that emotional load 08:41 — Kyle reflects on the "part-time job" hidden inside what should be passive income

09:07 — Oscar reveals the burnout facing operational teams and why they often quit 09:59 — The chaos spiral: missed calls, unanswered emails, confusion between owners, tenants, and institutions

10:11 — Kyle clarifies the definition of "relocated"—midterm stays of 1–11 months 11:06 — The mid-term rental boom: engineers, students, and global project workers 11:25 — The hidden burden for international offices and HR teams

12:00 — Kyle asks what makes Lodgering truly different 12:20 — Oscar reveals Phase 2: integrating AI to anticipate needs, automate proposals, and match services 13:13 — Kyle explores the benefits: saving time, saving money, protecting reputation 13:49 — Oscar describes how incident data helps predict, prevent, and budget issues 14:45 — Lodgering as a system for increasing occupancy, reducing operations costs, and improving decisions

15:00 — Kyle summarizes what users want: safety, clarity, peace of mind 15:21 — Oscar shares Lodgering's internal philosophy: "We Do Care," emphasizing empathy, not just technology

16:15 — Kyle begins the emotional story-mining process—inviting Oscar to recall core moments 17:08 — Oscar's breakthrough realization: booking emails in spam, endless paperwork, and unscalable chaos 18:32 — Kyle asks what Oscar's life looked like during this period 18:45 — Oscar shares honest details: 13–14 hour days, weekends preparing agendas, work as a "hobby" 19:25 — Golf: the only thing that finally pulled him out of work mode

20:10 — Kyle connects his experience to the emotional journey of Oscar's clients 20:36 — Oscar discusses ambition, effort, and the endless drive to improve 21:14 — Kyle asks for the contrasting future moment—when things finally aligned 21:50 — Oscar shares his dream: entrepreneur support, family time, and golf 22:30 — What has already changed: hiring an executive team, stepping into strategic leadership 22:55 — Leaving behind the "one-man orchestra"

23:09 — Kyle retells Oscar's story live—emotional, vivid, narrative form 26:43 — Oscar reacts: "You crossed my mind… that's exactly my story." 27:14 — Oscar reflects on the interview experience—"different in the best way" 27:28 — Where to find Oscar and learn more about Lodgering 27:55 — Closing the episode

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