Coordinates Unknown
Ep. 5

Charlie Ostertag: The Evolution of the Self-Taught COO

00:19:33

In this episode of Coordinates Unknown, we explore the remarkable evolution of Charlie Ostertag, COO of RedTag. Charlie’s journey is anything but linear—starting as a 16-year-old tattoo apprentice, he transitioned through manual labor at UPS and a printing press before teaching himself design on "YouTube University" and eventually rising to lead one of the region's top agencies.

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Guests

  • Charlie Ostertag

    COO, RedTag

Show notes

In this episode of Coordinates Unknown, we explore the remarkable evolution of Charlie Ostertag, COO of RedTag. Charlie’s journey is anything but linear—starting as a 16-year-old tattoo apprentice, he transitioned through manual labor at UPS and a printing press before teaching himself design on “YouTube University” and eventually rising to lead one of the region’s top agencies.

Charlie discusses the “scrappiness” required to survive the “Ramen Years” of entrepreneurship and the specific tenacity needed to turn a tiny six-person shop into an Emmy-award-winning powerhouse during a global pandemic. We dive into his “Diagnostic vs. Prescriptive” philosophy and why the best leaders are the ones who aren’t afraid to ask the hardest questions first.

In this episode, we explore:

  • The Tattoo Apprentice: How connecting with people in a tattoo shop taught Charlie the intimate art of understanding client needs.
  • YouTube University: The grit of teaching yourself a trade on nights and weekends while working manual labor.
  • The Pandemic Pivot: How RedTag doubled in size by doubling down on e-commerce while other agencies were shrinking.
  • Imposter Syndrome: Charlie opens up about the “burnout” phase and realizing that processes, not people, were the problem.
  • Leave Ordinary Behind: A look at the 2025 mission to challenge the expected and push the boundaries of AI and creative democratization.

The “Coordinates” (Timestamps)

  • 00:01:03 — The Kindergarten Hustle: How Charlie got in trouble for charging admission to a book fair.
  • 00:02:04 — The Shively Days: Walking two miles to a tattoo shop and the grit of a 16-year-old apprentice.
  • 00:04:14 — Manual Labor to Design: Moving from the UPS shipping floor to the printing press.
  • 00:05:42 — Self-Taught Excellence: Learning graphic design through “YouTube University” before TikTok existed.
  • 00:06:55 — The Agency Calling: Why “in-house” brand management felt too slow for a scrappy visionary.
  • 00:07:32 — The Frankfurt Ave House: Remembering the early days of a 6-person team in a tiny second-story office.
  • 00:08:48 — COVID & E-Commerce: Reaching a yearly sales goal in 30 days during the 2020 lockdown.
  • 00:10:18 — Facing Imposter Syndrome: Dealing with burnout and learning that company processes were the missing link.
  • 00:14:30 — The RedTag Doctor: Why a “diagnostic” approach beats a “prescriptive” one every time.
  • 00:16:01 — Hills, Valleys, & Ceilings: Knowing when your business has hit a plateau and needs a new map.
  • 00:17:23 — Leave Ordinary Behind: Challenging the democratized creative market with bold AI solutions.

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Are you currently hitting a ceiling in your business? Sometimes you have to leave the ordinary path to find the one that scales. Let us know your biggest “Unknown” in the comments below.

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