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 preview2:28 — Who Anthony was before he became a business owner4:04 — Where the self-development mindset actually came from6:01 — His father, a union carpenter, and lessons learned working with his hands8:17 — The party years: alcohol, weed, and finding control11:21 — Give yourself grace12:35 — Social media: the gift and the curse13:53 — Creator or consumer: rebuilding your own algorithm15:52 — What happened in his life to bring him here16:43 — Death and addiction: walking in on his uncle at age five17:23 — Watching his grandfather die of cancer at 1417:43 — Growing up around family dysfunction and substance use20:43 — The truth behind everyone’s highlight reel22:18 — You never know who’s watching22:36 — His first failed business: real estate wholesaling24:13 — The Florida flip that went wrong: a water line nobody could find25:20 — Going $30K into debt to learn commercial real estate25:57 — Raising $5 million in pledges that never actually closed26:57 — Meeting his business partner and pivoting to corporate housing27:15 — Why traveling construction crews and sports teams, not vacation renters28:16 — What rental arbitrage actually is29:09 — Already working with the Astros, in talks with the Yankees29:35 — Why “failure” might be the wrong word for any of this32:21 — When he decided to share his trauma publicly34:47 — Is God using him as an instrument?36:04 — His roller-coaster relationship with faith40:28 — When he felt furthest from God41:47 — The moment things started to turn around43:15 — Choice, consequence, and why it’s not God’s fault45:33 — The one book he’d recommend: The Daily Stoic46:49 — His biggest fear: letting himself down47:17 — What he wishes he knew years ago: build genuine relationships47:46 — Legacy: what he wants people to say about him51:06 — Raimo Renovations and the roof giveaway55:00 — How to reach Anthony RaimoConnect with Anthony: Instagram: @anthony.raimoWebsites: raimorenovations.com | tridentcorporatehousing.comBook a free real estate consultation with Steven:📞 (607) 669-3361🌐 Visit Website 📸 Instagram: @steve_padSupport the show