In this episode, Jason sits down with Jesse Perez, Founder & CEO of Classic Couriers, a Hollywood-based courier company founded in 1982. With 40+ years in the business, Jesse shares a rare behind-the-scenes look at studio logistics, Teamsters, film-era deliveries, and how Classic Couriers pioneered efficiency long before “last mile” became a buzzword.

From getting fired due to nepotism, to landing Paramount Pictures as the first client, Jesse breaks down how he shifted risk away from studios with a pay-per-delivery model, introduced early tech like two-way radios, and built a company that scaled to 100 union drivers and 4,000–5,000 deliveries per day at its peak.

He also shares unforgettable Hollywood moments including a personal encounter with Frank Sinatra and the quote that stayed with him every day: “The best revenge is massive success.”

Jesse explains how the industry changed forever during 2006–2008 (recession + writer strike + digital acceleration), how COVID reshaped studio work, and how he pivoted into tangible freight, entertainment logistics (sports/concerts), prescriptions, and warehousing.

02:17 – Intro: 40+ years in the game + “mob/mafia” stories teased
03:22 – Jesse Perez + Classic Couriers origins (founded 1982)
06:27 – Why Jesse got fired: nepotism + “not clearly legal” business
08:47 – Starting the company (and why delays saved them)
11:27 – What couriers did for studios: film, scripts, dailies, sound
14:27 – The studio problem: guaranteed union hours + “dog house” downtime
16:37 – Jesse’s model: pay per delivery + shift risk to Classic Couriers
18:57 – Indemnifying studios: workers comp, liability, cargo insurance
21:47 – Why W2 only + no subcontracting rules
24:47 – What made them different: preppy uniform concept + brand image
26:57 – Early innovation: two-way radios (before phones)
29:27 – Dispatch software + electronic billing + reporting data
32:37 – “The data is more important than the delivery”
35:37 – Film-era logistics: raw film → labs → dailies → actor homes
40:27 – Celebrities + Sinatra story + “massive success” quote
44:27 – Peak scale: 100 Teamsters + 4,000–5,000 deliveries/day
47:47 – Digital shift + recession/writer strike 2006–2008
52:27 – Pivot realization: “tangible things” vs digitized paper
55:27 – Expansion into sports, concerts, conventions, entertainment logistics
01:00:27 – Minority-owned path + union pushback + legal fight
01:08:57 – Breaking monopoly + opening doors for Black & brown workers
01:14:27 – Warehousing lessons: “cart before the horse” + humility
01:19:17 – COVID impact: studios ghost town + Rx delivery surge
01:23:47 – Last-to-First moment + risk, fear, and pivoting
01:27:57 – Final advice: don’t be afraid to pivot

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