Play It Smart

Georg Dauterman came to managed IT from the other side of the desk. A history degree, a quarter-life crisis, a Mac repair bench, then years running IT inside publishing houses and a Havas ad agency. In 2004 he quit, with a three-month-old at home, and joined Valiant Technology: a Mac-heavy managed service provider (MSP) for creative agencies in New York and Los Angeles, built when everyone else sold Windows and called it a day.

We get into how a creative-only practice actually runs. Every engineer gets a Mac and Parallels and a 90-to-180-day onboarding. Freelancers work in isolated environments priced so agencies can grow and shrink. The buying moment is not a breach, it is the day an agency hires a chief operating officer (COO) who reads the master service agreement (MSA) and realizes there is no HR, no finance, no IT. And after a year of outbound experiments that did not yield, the pipeline runs on referrals, Google reviews, in-person networking and his own podcast.

What we cover:

- Running Valiant on the Entrepreneurial Operating System (EOS), with the integrator seat split across two people
- Core values you can live with, and why "cheer" made the list
- A history degree, a Mac repair bench, and an education inside a Havas agency
- Quitting in 2004 with a newborn at home to join a non-cash-flowing business
- Block hours and hands-on work before the remote monitoring and management (RMM) tool existed
- The RMM-plus-cloud inflection that created the MSP industry, and why AI feels the same
- A Service Leadership peer group as his master's degree in business
- Cross-training every engineer, Mac and Windows both
- The unmanaged Macs sitting in your clients' boardrooms
- Due diligence questionnaires (DDQs), MSAs and the trust chain that makes agencies buy
- Employees and freelancers as two separate user classes
- Referrals, Google reviews and a podcast instead of a thousand dials
- The quarterly committee that decides the product stack
- Managed Model Context Protocol (MCP) servers for under $2,000 a month

Georg Dauterman: https://www.linkedin.com/in/georg-dauterman/
Valiant Technology: https://thevaliantway.com
The Creative Stack podcast: https://podcast.thevaliantway.com

What is Play It Smart?

Play It Smart is the show where Alexej Pikovsky sits down with MSP operators and business owners and takes apart how they actually do it: winning clients, pricing, staying lean, using AI, and building toward an exit worth having. Season 2 is dedicated to MSP operators. Past guests include Rand Fishkin of Moz and SparkToro and the founders of Chili Piper, Flowchat and 3DLOOK.