Episode Summary
In this episode, Russel Dubree sits down with Hillary Applegate, founder of Digital HQ, a modern marketing and communications agency built around flexible work. Hillary shares her journey from Silicon Valley upbringing to running a remote-first agency, and the surprising lessons she learned when she stepped away from her business for the first time.
Episode Highlights
- How stepping away helped Hillary see her agency more clearly, and why everything felt “smaller” when she returned
- The mindset shift required to trust your team and release control
- The cultural and operational benefits of embracing flexible work
- How motherhood reshaped Hillary’s leadership philosophy
Agency Info
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Company: Digital HQ
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Guest: Hillary Applegate
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Year Started: 2020
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Employees: 11-25
Letting it go into the world took a lot of energy, but when I came back, I realized the things I’d been so worried about weren’t nearly as big.
Hillary Applegate
Distance Creates Clarity
Hillary describes returning from her leave and realizing that the problems that once felt heavy simply weren’t. Stepping away gave her a new vantage point, revealing what mattered and what was noise. You can’t always fix operational strain by working harder. Sometimes clarity requires distance.
Letting the Team Stand on Its Own
Before her leave, Hillary felt the familiar pressure many agency founders feel: if she wasn’t present, the business might falter. Watching the team operate without her became proof of their capability. Trust is a leadership skill, not a personality trait. Your business becomes more resilient when you relinquish the instinct to be everywhere.
Flexible Work as an Operating Model
Digital HQ was built on the idea that great people deserve autonomy. Hillary explains why remote-first structures not only attract incredible talent but also foster stronger output. When people have control over how they work, they bring more energy and focus to what they do.
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