Penny Boy Tattoo

PENNY BOY’S SEMINAR

IT'S ABOUT TIME

The secrets nobody will tell you.

Not a theory class. Real practice, real progress.

SEATS ARE LIMITED

BOOK NOW

March 19th- 20th 2026

📍 Donald E. Stephens Convention Center

5555 N River Rd,
Rosemont, Il 60018

What You'll Learn

In two days you’ll learn to tattoo smarter, not harder.

1. Where the magic starts

Idea & concept: how to turn a brief
into a strong traditional design.

2. How to draw on skin

Structure & composition that hold up on skin for life.

3. Tattoo smarter

Needle, ink & machine strategy
for bold lines and solid color.

4. Learn live

Full tattoo breakdown, step by step.

5. Apply it now

Guided practice with direct feedback.

6. Plus

SURPRISE Starter Pack to use during the seminar and take home + a chance to be randomly selected for a free live tattoo by Penny Boy during the session.

Who Is This For?

Level up your Traditional. In 2 days, you’ll learn a proven system that takes you from idea to stencil, bold lines to solid color, consistently.

This training is for working tattooers and committed apprentices who want to:

  • Create designs that pop instantly and stay powerful over time

  • Work faster with reliable setups, no more guessing

  • Attract better clients and raise your prices with a stronger portfolio

  • Refine your signature style with focused, practical feedback

  • Open doors to conventions, guest spots, and high-level collaborations

Come ready to draw, learn, and put in the work.

Detailed Program

DAY 1 - THURSDAY 19th

9a.m. - 8p.m.

Morning: Mindset, Idea & Design

  • How to build a strong tattoo concept: where ideas come from and how to use symbolism in traditional tattoos.
  • How to structure a design for skin: composition, balance of black, readability from a distance.
  • Sketching session: Penny builds a design live and helps you adjust yours.

Early Afternoon: Free Hand & Technical Setup

  • When and how to draw directly on skin (free hand) vs stencil.
  • Live demo on body flow: adapting designs to anatomy.
  • Needles, machines, and colors: why, how and when to choose the right setup for lines, black, shading and color.

Late Afternoon: Live Tattoo Lottery

  • One participant is randomly selected and receives a free tattoo by Penny.
  • Full live tattoo with step-by-step explanations:
    • station setup, stencil/free hand,
    • lines, black, shading, color order and saturation.
  • You can watch on screen, come close in turns and ask questions during the whole process.
  • Only short stories are allowed – no full recording.

DAY 2 - FRIDAY 20th

8a.m. - 1p.m.

On day 2 you tattoo your own client, and Penny follows you step by step.

Setup & Placement

  • You set up your station and prepare your design.
  • Stencil or free hand placement on your model, checked and corrected by Penny (size, flow, position).

Guided Tattoo Session

  • You tattoo your model from start to finish:
    • linework, black, shading, color.
  • Penny walks around the room constantly:
    • corrects technique,
    • suggests better needles or approach,
    • explains what to change and why, so everyone learns from each correction.

Final Wrap-Up

  • Review of the tattoos: what works, what to improve next.
  • Final Q&A about technique, workflow, portfolio and clients.
  • Closing with a special surprise for participants.

Surprise Starter Pack

Every attendee gets a surprise Starter Pack curated by Penny and powered by our sponsors: a mix of pro-level tools and seminar-only goodies you’ll use during the seminar and take back to your shop.

*exact contents may vary.

Why Learn from Penny Boy

Penny Boy (Massimiliano Pennella) is an internationally renowned Italian tattoo artist specializing in Traditional. With 14+ years behind the machine, he has attended 300+ conventions, judged major contests, and earned 100+ awards across Europe and the U.S.

Book your spot

Join Penny Boy’s exclusive 2-day seminar and unlock a complete professional experience designed for artists who want to elevate their craft.

Your ticket includes:

Full 2-Day Access

Enjoy complete access to all seminar sessions, insights, demos, and live training across both days.

A Chance to Win a Free Tattoo

One lucky attendee will receive a free tattoo, performed live during the event.

Assisted Practice Day

Get one full day of guided, step-by-step support while working on your tattoo.

Free Starter Pack

Receive a curated Starter Pack filled with essential tools and professional items to take home and continue practicing.

Proudly Supported by

Hustle Butter

Sullen Clothing

Radiant Colors Ink

FAQ

Is the seminar hands-on?

Yes. Day 1 includes demos and theory; Day 2 you tattoo your own model under Penny’s supervision.

Mindset, design structure, free hand, tools, and a full live tattoo demo.

Yes. Each participant completes a tattoo from start to finish with real-time guidance.

Only short stories are allowed. No full recordings.

Yes. Penny reviews your setup, technique, and final tattoo, giving direct corrections.

Yes. On Day 2 you must bring a model to tattoo; the entire day is focused on tattooing under Penny’s supervision.

The ticket is not refundable or transferable.

DO YOU HAVE MORE QUESTIONS?

Fill out the form and I’ll write back as soon as possible.

Thank you!

We'll get in contact as soon as possible.

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@pennyboy_tattooartist