From Bartending on Bourbon St to Multi-Million Dollar Commercial Real Estate Deals: Chris Ross on Short Sales, Hotels and Leveraging Equity

On Episode 42 of Rich Lessons, Sevetri Wilson Taylor (Instagram.com/sevetriwilson) and Sheena Allen(Instagram.com/whoisSheena) sit down with real estate investor, developer, and agent Chris Ross, whose path into commercial real estate began behind a bar on Bourbon Street and led to multi–million–dollar hospitality and mixed-use deals.Chris shares how he went from making $800 on his first $45K deal to brokering $30M+ transactions, and why he believes now is still a powerful moment to move into commercial real estate, especially as others run away from office buildings and underperforming assets. He breaks down how to leverage equity, recognize the subtle signs of opportunity (like worn pool furniture and empty elevators), and think beyond single-family rentals into hotels, large residential properties, and creative adaptive reuse.The conversation also dives into real estate as a reflection of culture—from office-to-residential conversions and content studios to the rise of Airbnb-style hospitality. Chris explains how he utilizes AI and ChatGPT daily in his brokerage work, without compromising the human element that actually closes deals. And in his Rich Lesson, he brings it all back to one core principle: relationships are the real asset in business and in building long-term wealth.Show Notes:(00:00) Intro — Meet Chris Ross: Bourbon Street bartender turned commercial real estate dealmaker(01:07) From phone book to first license — breaking into real estate without a “traditional” background(02:47) Leaving residential behind — the persistence that opened CRE doors(03:43) What most people don’t know about commercial real estate: leveraging equity and financing million-dollar deals(05:02) “Blood in the water” — short sales, distressed assets, and why Chris thinks now is still a good time for CRE(06:15) How he turned bad pool furniture and empty elevators into a $35M transaction(08:19) The $45K building and an $800 commission — why you can’t start at $30M deals(09:49) Balancing culture, preservation, and profit in New Orleans while bringing more Black entrepreneurs into big deals(12:02) Where to start in hospitality and commercial: valuation, learning from the bottom up, and knowing your investing style(21:08) How Chris uses AI and ChatGPT daily in real estate (and why relationships still matter more than ever)(29:26) Real estate follows culture — office conversions, content studios, data centers, and shifting demand(33:00) Airbnb vs hotels — pros, cons, profitability, and why consistency still sells(39:29) Rich Lesson — relationships, credit unions, and why your network is your true leverage—Rich Lessons Podcast // hosted by Sevetri Wilson Taylor and Sheena AllenSubscribe to Rich Lessons on Apple Podcasts (https://podcasts.apple.com/us/podcast/rich-lessons/id1787798124) and Spotify (https://open.spotify.com/show/40jGSUvVrMbxKcJ1ghE8kl)Watch and subscribe to Rich Lessons on YouTube (https://www.youtube.com/@richlessonspodcast)Follow Rich Lessons on Instagram (https://www.instagram.com/richlessonspodcast/) and TikTok (https://www.tiktok.com/@richlessonspodcast)