She generated $20M throughout her career (here’s how!)

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Caitlin is an embedded operations specialist, business strategist, and founder who has helped over 100 founders scale their businesses. Previously, she grew and exited her own business while generating over $20 million in value for her clients. Her work at various companies ranged from operational optimization to strategic growth planning to AI implementation frameworks. She is also a founder of her own consulting practice at coopilots.io, a business that provides embedded operations support for scaling companies.

What you'll learn:

1. How to break the "whiteboard paralysis" that keeps founders stuck in planning mode instead of testing ideas

2. Why situational leadership frameworks help founders delegate effectively without losing control

3. The specific methodology behind "decision journaling" to build confidence in high-stakes choices

4. How to create a "Keystone document" that makes AI 10x more effective for business operations

5. Why reframing sales as problem-solving eliminates the "icky" feeling around business development

6. The two critical mistakes that prevent 90% of founders from successfully scaling their businesses

7. How to design operational workflows around individual energy patterns and zone of genius

8. Why 2024-2025 represents a golden age for founders despite market volatility and AI disruption

Some takeaways:

The "No Battle Plan Survives Contact" Principle: Founders get trapped perfecting ideas at the whiteboard that never survive real-world testing. Ferguson literally kicks founders away from planning and forces customer conversations. In her experience with 100+ founders, the initial concept never becomes the final profitable version—market fit only emerges through customer iterations.

The Delegation Paradox for Scaling: At 3-5 employees, founders hit their biggest bottleneck: letting go. Ferguson advocates against "founder mode," arguing it creates expensive hobbies that burn out leaders. She conducts energy audits to identify what founders love versus what drains them, then delegates everything outside their zone of genius.

Decision Journaling for Founder Confidence: Ferguson's three-part framework combats decision replay loops: document the decision, record context and expected outcome, then close the notebook until results emerge. This builds pattern recognition while reducing analysis paralysis from making decisions on limited information.

The Keystone Document Revolution: Instead of constantly re-coaching AI tools, Ferguson creates comprehensive business context documents with company values, problem-solving frameworks, and client examples. This platform-agnostic approach delivers consistent AI outputs while maintaining team uniformity across tools.

Sales as Service, Not Transaction: Ferguson transforms sales anxiety by reframing it as problem-solving. Her mentor's question—"Do you genuinely believe you can help people?"—shifted her focus from self-promotion to service, making sales feel like doing favors rather than extracting value.

The AI Implementation Sweet Spot: While founders fear expensive technical lifts, Ferguson demonstrates immediate wins with simple frameworks. Her system analyzes sales calls, assesses client fit, and generates proposals in 5-10 minutes—eliminating hours of manual work without requiring technical skills.

The Mom Test for Real Customer Insights: Ask about past behaviors, not future intentions. Instead of "Would you buy my cookbook?" ask "When did you last buy a cookbook and what did you spend?" This reveals actual buying patterns and prevents false product-market fit signals.

Community-Driven Business Transitions: Ferguson's pivot to independent consulting came through community pressure to claim her $20 million client impact. External validation helped overcome the barrier of attributing wins to clients rather than acknowledging her own contribution.

The Golden Age Contrarian View: Despite market volatility and AI fears, Ferguson sees 2024-2025 as exceptional for founders. Like internet adoption, major innovations create more jobs than they eliminate. First-mover AI advantages offer unprecedented opportunities for adaptive entrepreneurs.

Links:

Where to find Caitlin

• Linkedin: https://www.linkedin.com/in/ceoferguson/

• Website: https://www.coopilots.io/

• Podcast: https://groundsforgrowth.podbean.com/

Where to find Milly

• Linkedin: https://www.linkedin.com/in/milly-tamati/

• Website: http://www.millytamati.com/

Generalist World resources:

• Podcast on Spotify:

• Podcast on Apple:

• Podcast on YouTube: https://youtu.be/Ciq7MVz_hzY

• The Generalist Quiz: https://www.generalistquiz.com/

• The AI fluency Quiz: https://www.aiskillsquiz.com/

• Essays: https://www.generalistcareer.com/

• Upcoming events: https://lu.ma/generalist.events

• Positioning Guidebook: https://www.generalist.world/positioning

🙏 Special thanks to our podcast producer James McKinven! (get in touch for all your podcast needs, he’s really great!)