Fully Managed

From Freelance Writer to 7-Figure Founder — The Origin Story of Content Cucumber

Episode Summary

In this episode of Fully Managed, we sit down with Isaac Morey, Co-Founder and CEO of Content Cucumber, to uncover how a college freelancer turned a handful of writing gigs into a scalable content subscription business.

Episode Notes

Isaac shares: 

• The exact community that landed their first clients 

• Why scaling meant giving up the “writer” hat 

• The unexpected hiring strategy that landed their first 100+ writers 

• How AI has changed (and challenged) the future of content writing 

• The unique backstory behind the name Content Cucumber 

We also dive into his strategies on lead generation, growing a team, and how Penji and Content Cucumber share a kindred subscription-based model for creative services. 

Plus, don’t miss the fun “lightning round” at the end where Isaac shares his go-to karaoke song, favorite emoji, and more