Hosts: Caitlin Ferguson (COOPilots.io) and Rob Ripp (Fintelligent, Author of Finance for Founders)
are a COO-CFO duo discussing supporting founders through growth challenges.

This episode covers:

Main Discussion Points

Valley of Death & Financial Stress

• Scaling = spending money with uncertain payoff, 18 months later founder only one not making money
• Success key: Test/track/measure deliberately - 3-month experiments, clear objectives, hold accountable
• Know: funding source, what you'll give up, what payoff looks like
• If asking business to produce more than capable (lifestyle > capacity) = crisis

What Nobody Talks About

• 70% entrepreneurs have mental health effects (likely higher)
• 50% businesses fail in 5 years, only 4% reach $1M
• Warning signs: fewer distributions, attitude shifts, A-players leave first
• Founders cover errors with debt until insolvent
• If you think you're spiraling, you are - get help

Hard Conversations

• Rob: Provide founders with trade-offs and consequences, in lieu of instructing outright
• Present burn rate, runway (6-12 months), options
• If can't be candid, relationship won't work
• Caitlin's hardest: Founder's leadership style was problem (team energy gone)
• Requires candor with empathy

The Hidden Burden

• Company thriving but founder shouldering unsustainable load
• Self-check: Long silences when you speak? People shifting uncomfortably?
• Must give up something emotional to scale, not just time/money
• Know it's handled through reporting even when you let go

Ship It, Don't Perfect It

• Reality: 100+ founders - whiteboard version never wins in market
• Rule: If comfortable showing best friend but not public - ship it
• Need market data, not perfection

Decision Tools

• Decision matrix: Ask "what makes this a good decision?" before choosing
• Decision journaling: Write decision, context, expected outcome → review later → confirm instincts or spot blind spots

Choosing the Right Partner

• Chemistry critical: Fractionals = part-time + remote. If need daily meetings/physical presence = wrong fit
• Find complement: Overlap in what energizes (shared foundation) but they own what drains you
• Stage matters: Too much daily flux = fractional flatfooted. Sometimes need accountant not CFO
• Industry expertise essential (professional services ≠ SaaS ≠ construction)

When to Transition

• Scale out: $15-20M = afford full-time CFO/COO
• Entry floor: Business changes Monday to Friday = fractional won't succeed
• Embedded junior + fractional senior = preserves context when fractional exits

Growth Stages

• 0-$2M: Survival, gut feel, grit
• $2M-$10M: Need process, max 5-7 direct reports, culture takes over
• $10M+: Must have financial + operational systems or big problems

Notable Quotes

• Rob: "If you think you're spiraling, you probably are."
• Caitlin: "Whiteboard version never wins in market - ship it."
• Caitlin: "Decision journaling confirms instincts or spots blind spots."

Resources: Decision Journal Template Mastermind communities - Entrepreneurs Organization / EO & Collective 54 / C54