Nov 13, 2026 · 1h 7m
Ryan Drumheller turns toxic IT experience into a golf venture
From Firewalls to Fairways: Ryan Drumheller on Toxic Workplaces, Leadership and Golf
The conversation connects career reinvention, humane leadership, and AI disruption to the difficult decision of when to leave a damaging workplace.
- 1Career reinvention can begin with returning to school, building expertise, and pursuing a new direction after burnout.
- 2AI can amplify capable IT teams, but human judgment remains essential for security, strategy, and evaluating results.
- 3Dogleg Digital aims to replace golf’s fragmented technology landscape with a more connected ecosystem for players and businesses.
Don't miss
Drumheller explains how recognizing persistent dread, anger, declining energy, and a fading sense of self can signal that it is time to leave a toxic job.
The brief
Ryan Drumheller recounts starting college at 29, building a career through degrees and more than 170 certifications, then moving from IT leadership toward golf entrepreneurship.
His account of toxic workplaces centers on a practical leadership test: communicate honestly, protect people, and recognize when staying means losing energy, values, or a sense of self.
Drumheller argues that AI is a force multiplier, not a substitute for expertise; people still must direct systems, assess outputs, and protect security.
Golf became both recovery and a new business direction, inspiring From Firewalls to Fairways and Dogleg Digital, which seeks to connect courses, vendors, instructors, facilities, and golfers.
The episode’s clearest lesson is that setbacks do not settle a career: like a bad round, the next decision can still change its direction.
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