Jason Berkowitz Learned SEO to Get Gym Clients (Then Built a 7-fig Agency By Accident) - #16

Legends of Scale · May 20, 2026 · 44m

Today we talk with Jason Berkowitz, founder of Break the Web.

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00:00 Meet Jason Berkowitz

01:12 The Exit Interview That Forced Him to Delegate

02:33 Building Links From His Queens Apartment

05:39 Why He Went Fully Global (Zero US Employees)

10:02 "Getting Ghosted by Girls AND Employees"

12:10 Rules vs. Core Values (The Difference)

17:24 "The Hills You'd Die On" Aren't Worth It

19:32 Not Firing Fast Enough (The Fear of Things Breaking)

24:49 The…