Side Hustle School Ep. 3295 - TBT: Best Guitar Lessons in the Universe
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Jan 8, 2026 Jake Posco, the owner of Severn River Music and a guitar teaching entrepreneur, shares his journey from side hustle to full-time success. He discusses how he uniquely marketed his lessons through Craigslist and ads. Jake offers a practical three-step startup plan and emphasizes the importance of validation in business ideas. He also opens up about the mental health challenges of working alone and the loneliness of entrepreneurship. His insights highlight the significance of teaching skill over technicality in building a successful service-based venture.
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From Craigslist To A Music Business
- Jake Posco started with a Craigslist ad and grew Severn River Music from that first student into a full business.
- He transitioned from teaching himself to contracting lessons and adding affiliate sales to create passive income.
Scaling Toward Passive Income
- Jake shifted away from teaching to focus on passive income like contracting and affiliate sales.
- This allowed him to reclaim time for writing and music while keeping revenue streams active.
The Hidden Cost: Anxiety And Isolation
- Running a solo business often causes anxiety and isolation that few entrepreneurs discuss openly.
- Jake warns this is normal and preparing for those walls helps you persist and succeed.
