How do you turn a cold email into a $30M+ global engine?

Caleb Gilbertson, Founder and CEO of Imprint Engine, joins Jeremy Parker to share the high-stakes story of building one of the promotional product industry’s most tech-forward global agencies. From a small Minneapolis apartment to $150M+ in lifetime revenue, Caleb’s journey is a masterclass in scaling with speed and intent.

In this episode, Caleb pulls back the curtain on the ”Uber Era”—the wild years where a single client made up 90% of their revenue—and how they successfully navigated the ”concentration trap” to become a diversified global powerhouse with offices in Dublin, India, and Australia.

Key Takeaways:

• The Uber Effect: What it’s really like to hitch your wagon to the fastest-growing startup in history and the hard lessons learned when it came time to diversify.

• The ”Janitor” Leadership Style: Why Caleb’s Slack title is ”Janitor” and how empathetic leadership drives a high-performing global culture.

• Shipping Global vs. Being Global: The logistical reality of building truly integrated teams across three continents and why local presence is the ultimate enterprise differentiator.

• The AI Frontier: How Caleb’s tech and design background led to the creation of Merch AI and how he is using automation to reduce friction, not add complexity.

• The Power of Delegation: Moving from ”apartment-style” micromanagement to hiring people smarter than yourself to reach the $100M milestone.

Whether you’re a distributor looking to expand your footprint or a founder trying to survive a period of hyper-growth, Caleb’s insights on consistency and “trusting the process” are essential for any entrepreneur in the swag space.

#promotionalproducts #entrepreneurship #globalbusiness #leadership #swagtech #imprintengine