When I was an apprentice flipping through tattoo magazines, Jesse Smith's work stopped me in my tracks. Fast forward to today, and I'm sitting down with the man himself, someone who's spent over 25 years proving that unconventional paths can lead to extraordinary outcomes.

Jesse started tattooing with a prison-style gun made from a toothbrush and Walkman motor, learned by trial and error, and built an empire that includes Loose Screw Tattoo, the Richmond Tattoo and Arts Convention, and the Richmond Tattoo Academy.

This conversation isn't about shortcuts or hacks—it's about the real work that transforms artists into industry leaders. Jesse breaks down why your drawing skills matter more than any machine or technique, how to build systems that set you up for success, and what it means to leave the tattoo industry better than you found it.

Connect with Jesse:

• Jesse Smith's Website: jessesmithtattoos.com

• Jesse Smith on Instagram: https://www.instagram.com/jessesmithtattoos

What You'll Learn in This Episode:

• Why drawing fundamentals trump tattoo application every time – Jesse explains that while the technical process of tattooing is relatively straightforward to learn, drawing skills take a lifetime to develop and are the true foundation of great tattoo work.

• The reality of being self-taught in tattooing – Hear the honest story of Jesse's unconventional start, from making ghetto guns to scrubbing tubes barehanded in his first shop, and why he still recommends formal apprenticeships despite his own success.

• How to build systems that force you toward success – Learn practical strategies like Jesse's seven-pair underwear rule and environmental triggers that create accountability and keep you moving forward, even when motivation fails.

• The truth about shop ownership and who you're really working for – Jesse gets real about the misconception that opening your own shop means working for yourself, when in reality you're working for your clients and employees.

• Why self-awareness is your most valuable business tool – Discover how being introspective about your weaknesses, implementing feedback from clients, and constantly checking yourself are what separate successful tattoo artists from those who plateau.

• The importance of drawing constantly throughout your entire career – Even after decades of experience, Jesse still finds himself getting perspectives, light sources, and flow wrong—reinforcing that the learning never stops.

• How to make a lasting impact in the tattoo industry – Jesse shares his ultimate goal: to bend the direction of the tattoo industry in a positive way and leave it better than he found it, offering a bigger-picture perspective on building a legacy.

Jesse Smith, owner of Loose Screw Tattoo and two-time Ink Master competitor, shares his unconventional journey from self-taught scratcher to industry leader over 25+ years. Learn why mastering drawing trumps tattoo application, how to build sustainable systems for success, and what it really takes to make a lasting impact in the tattoo industry.

Links:

boundbyart.com

bluebirdtattoos.com

instagram.com/tattoosbymissiblue

instagram.com/boundbyartproject

instagram.com/bluebirdtattoostudio

Music: Unknown Road - The Harp Project