Link Live with Lorenzo Costa
Welcome back to the Link Live Podcast, presented by Link Creative. For Episode 19, host Lorenzo Costa, CEO of Link Creative, is joined by a powerhouse in the Chicago hospitality and real estate scene: Sebastian, the Founder and CEO of The Dream Rental Chicago and the operator of the Plymouth Hotel Chicago. Sebastian is a master of the "Hospitality Pivot," transitioning from a career selling and managing at Cutco into building a massive short-term rental empire. From a "trial by fire" start right before the global pandemic to managing a portfolio of over 100 units, Sebastian joins the pod to discuss the shift from simple "Airbnbs" to high-level boutique hospitality and the grit required to scale in one of the most regulated cities in the country. Inside the Episode In this conversation, Lorenzo and Sebastian break down the evolution from a side-hustle mindset to a high-stakes hospitality CEO: * The Arbitrage Advantage: Why renting properties to re-rent them (Arbitrage) allowed Sebastian to scale faster with less capital than traditional real estate investing. * Surviving the "Wild West": Navigating the early days of COVID-19, dealing with "disaster scenarios," and the reality of high-stakes parties and property damage. * The Shift to Hospitality: Why "staged" properties are failing and why Sebastian is positioning his brand as the "Host of Chicago" to survive the algorithm. * The Plymouth Project: A behind-the-scenes look at winning a bankruptcy auction for a hotel and the massive operational leap from single units to full-building management. > “Revenue is vanity, profit is sanity. As you grow a business, it’s less about the numbers and more about who you are becoming to actually handle that stress.” — Sebastian SEBASTIAN & THE DREAM RENTALS * Instagram: @sebas___tian * Business Instagram: @thedreamrentals * Website: thedreamrentals.com [https://thedreamrentals.com] LINK CREATIVE: * Website: linkcreativeco.com [https://linkcreativeco.com] * YT: @linkcreativeco * Instagram: @linkcreativeco * TikTok: @linkcreativeco * LinkedIn: Link Creative 00:00:00 Intro & Hook 00:00:32 Guest Introduction 00:01:37 Upbringing & Early Career 00:02:27 First Airbnb & Surviving Covid 00:05:33 Airbnb Arbitrage vs. Traditional Rentals 00:08:01 Navigating Chicago Regulations 00:10:08 Crazy Airbnb Horror Stories 00:11:35 How to Get Started in Arbitrage 00:15:29 Building a Hospitality Brand 00:17:46 Quitting the 9-to-5 Job 00:19:20 Transferable Skills from Sales 00:21:39 Building Systems & Hiring a Team 00:23:25 Best Software Tools for Airbnb 00:26:26 The Value of a Business Partner 00:28:24 Best Locations to Invest 00:30:46 Expanding Out of State & Internationally 00:33:08 Future Portfolio Goals 00:34:27 Realistic Profit Margins 00:36:00 Leveraging Debt to Scale 00:37:51 The Plymouth Hotel Acquisition 00:43:50 Hotel Operations vs. Airbnbs 00:46:31 Driving Additional Revenue Streams 00:48:22 Social Media & Networking 00:50:52 Managing Stress & Preventing Burnout
12 episodios
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