From Musician to Entrepreneur | Episode 74 with Jarrett Forrester

Jarrett Forrester joins Sunday Afternoon Smokes to discuss entrepreneurship, customer service, branding, and the unexpected path that led him from full-time musician to business owner. Known throughout the Southeast as a touring Americana and country artist, Jarrett shares how Cowboy Custom Printing was born almost by accident after a frustrating business experience revealed an opportunity to do things differently. What started as a side venture quickly grew into a thriving apparel and promotional products company built on relationships, creativity, and helping customers succeed. Chris and Jarrett explore what makes great merchandise actually sell, why customer trust matters more than a single transaction, the challenges of building a business from scratch, and how authenticity creates long-term opportunities. Along the way, they discuss branding, entrepreneurship, fatherhood, music, cigars, and the value of creating products people are genuinely excited to wear. This conversation offers an inside look at the mindset of a creator who has built careers in both music and business by focusing on relationships first and sales second. Topics include entrepreneurship, branding, custom apparel, merchandise design, small business ownership, customer service, touring musicians, fatherhood, creativity, marketing, and building a business through genuine connections. Cowboy Custom Printing: https://www.instagram.com/cowboycustomprintinggvl/ Jarrett Forrester Music: https://www.instagram.com/jarretforrestermusic/ https://www.youtube.com/@jarretforrestermusic Sunday Afternoon Smokes: https://sundayafternoonsmokes.com/ https://www.instagram.com/sundayafternoonsmokes/