Feb. 12, 2026

How to Scale Your Business in 2026: 5 Lessons from an Innovation Co-Pilot Chris Cushing

How to Scale Your Business in 2026: 5 Lessons from an Innovation Co-Pilot Chris Cushing
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How to Scale Your Business in 2026: 5 Lessons from an Innovation Co-Pilot Chris Cushing
How to Scale Your Business in 2026: 5 Lessons from an Innovation Co-Pilot Chris Cushing

In this episode, Air Force veteran and "innovation co-pilot" Chris Cushing explains how creative entrepreneurs can scale their businesses by transitioning from basic delegation to high-level operational management. She shares actionable strategies for overcoming the "control trap," utilizing tools like Loom for seamless training, and implementing the systems necessary to see around business corners before they become obstacles.

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Are you drowning in daily tasks and losing sight of your creative vision? In this episode of The Creative Entrepreneur, we sit down with Chris Cushing, an Air Force veteran and the founder of VA Victory. Known as the "innovation co-pilot" to high-level executives, Chris shares how she helps entrepreneurs see around corners and regain control of their time.

From her roots in basic training to managing complex operations for Creative Con, Chris discusses the vital transition from "hiring a VA" to bringing on an Online Operations Business Manager (OBM). If you’ve ever struggled with the "entrepreneurial bottleneck"—the inability to let go of control—this episode is your roadmap to scaling without the burnout.

Key Takeaways & "Jules Rules" for Success

  • The Power of the Loom Video: Stop repeating instructions. Use Loom to record your screen, show exactly how a task is done, and build a library of SOPs (Standard Operating Procedures) for your team.

  • The 24-Hour Rule: Timely communication is a non-negotiable for success. If you can’t reply immediately, an "Out of Office" message is essential to maintain professional integrity.

  • Under-Promise, Over-Deliver: Build trust by setting realistic expectations and then exceeding them.

  • Stop the Inconsistency: The biggest mistake entrepreneurs make is being unwilling to change outdated systems because it's "their baby."

  • Trial Tasks: When hiring, give a small paid task with a hard deadline to see how a candidate operates under pressure before signing a long-term contract.

Episode Highlights

  • [00:00] Meet Chris Cushing: The veteran behind the "DAM system" and Air Force veteran.

  • [04:15] Military Discipline in Business: How the Air Force shaped Chris’s leadership and organizational skills.

  • [08:40] From VA to OBM: Why your $25/hour VA might actually be an Online Operations Manager.

  • [12:30] The "Time-Suck" List: A practical exercise to identify which tasks you need to delegate first.

  • [15:50] Jules Rules – Entrepreneurial Pet Peeves: * Lack of substance (the "all talk, no website" syndrome).

    • Being late to Zoom calls.

    • Poor follow-up at networking events.

  • [22:15] Managing the Managers: When you’re too busy "babysitting" your team, it’s time for an OBM.

Connect with Chris Cushing


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