
EP52 — Anthony Raimo: From Selling Drugs to Housing MLB Teams
Anthony Raimo sold drugs as a teenager at Fordham Prep, walked in on his uncle's overdose at age 5, and watched his grandfather die of cancer at 14. Today, at 25, he runs Trident Corporate Housing — a rental arbitrage business currently working with the Houston Astros and in talks with the New York Yankees — and Raimo Renovations, a full-scale general contracting firm. Topics covered: 0:00 — Season 2 intro and episode preview 2:28 — Who Anthony was before he became a business owner 4:04 — Where the self-development mindset actually came from 6:01 — His father, a union carpenter, and lessons learned working with his hands 8:17 — The party years: alcohol, weed, and finding control 11:21 — Give yourself grace 12:35 — Social media: the gift and the curse 13:53 — Creator or consumer: rebuilding your own algorithm 15:52 — What happened in his life to bring him here 16:43 — Death and addiction: walking in on his uncle at age five 17:23 — Watching his grandfather die of cancer at 14 17:43 — Growing up around family dysfunction and substance use 20:43 — The truth behind everyone’s highlight reel 22:18 — You never know who’s watching 22:36 — His first failed business: real estate wholesaling 24:13 — The Florida flip that went wrong: a water line nobody could find 25:20 — Going $30K into debt to learn commercial real estate 25:57 — Raising $5 million in pledges that never actually closed 26:57 — Meeting his business partner and pivoting to corporate housing 27:15 — Why traveling construction crews and sports teams, not vacation renters 28:16 — What rental arbitrage actually is 29:09 — Already working with the Astros, in talks with the Yankees 29:35 — Why “failure” might be the wrong word for any of this 32:21 — When he decided to share his trauma publicly 34:47 — Is God using him as an instrument? 36:04 — His roller-coaster relationship with faith 40:28 — When he felt furthest from God 41:47 — The moment things started to turn around 43:15 — Choice, consequence, and why it’s not God’s fault 45:33 — The one book he’d recommend: The Daily Stoic 46:49 — His biggest fear: letting himself down 47:17 — What he wishes he knew years ago: build genuine relationships 47:46 — Legacy: what he wants people to say about him 51:06 — Raimo Renovations and the roof giveaway 55:00 — How to reach Anthony Raimo Connect with Anthony: Instagram: @anthony.raimo Websites: raimorenovations.com | tridentcorporatehousing.com Book a free real estate consultation with Steven: 📞 (607) 669-3361 🌐 Visit Website 📸 Instagram: @steve_pad Support the show







