What do you do when you’re hogtied at gunpoint in a Brazilian penthouse? Or broke in Sri Lanka trying to make a business work from scratch?

For Evan Cassidy, those weren’t hypotheticals—they were chapter one.

In this raw and revealing episode of Founders & Empanadas, Joshua Eidelman sits down with Evan to unpack the wild, global journey that eventually led him to build Booming Brands, a white-labeled video editing agency now producing 4,000+ videos per month.

They cover:

• The violent home invasion in Brazil that changed Evan’s life

• The freelancer trap most digital founders fall into

• How to tell when a startup is failing—vs. when you’re just quitting too early

• Why founder skills don’t scale (and how to grow into a real CEO)

• A tactical system for finding product-market fit in services

• The difference between resilience and denial when chasing a vision

If you’ve ever wondered whether to keep pushing—or finally let go—this conversation will hit home.

📌 TIMESTAMPS:

0:00 – Intro + Empanadas

2:00 – Leaving corporate life for Brazil

4:30 – The home invasion story

9:30 – Faith, fear, and navigating chaos

12:00 – Moving to Sri Lanka + freelancer years

16:00 – Failed course launch + debt

17:30 – Iterating into Booming Brands

22:00 – Traits that don’t scale from founder to CEO

26:00 – Leadership mistakes that haunt you

29:00 – Picking yourself up after failure

32:00 – Final hot take: Don’t diversify too soon

🎧 Full episode available on Spotify, Apple Podcasts, and wherever you get your shows.