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:

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