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

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:

The AI Payoff

• Goal: Double revenue without increasing headcount through operating leverage
• For every dollar of revenue, add less than a dollar in costs
• Labor = 40%+ of professional services revenue - AI can dramatically reduce this

When to Automate (4 Criteria)

1. Set rules: Repeatable with predictable steps
2. Templatized: Existing framework used regularly
3. Jam session: Comfortable iterating with AI, human in loop
4. Room to play: Low stakes, internal-only

MIT Study Reality Check

• 95% of AI initiatives not hitting P&L (no ROI)
• 5% succeeding = backend operations only
• Problem: AI tools not learning/adapting over time
• Greatest gains outside client delivery (big opportunity gap)

Keystone Document Solution

• AI like "entry-level intern" with no continuity between sessions
• Create central doc (Keystone): how you communicate, frameworks, past successful work
• Makes AI consistent across any tool
• Example: Proposal generation 3-5 minutes vs. 1-2+ hours

Three Types of AI

1. Embedded: Built into systems (QuickBooks AI creates monthly summaries)
2. Generative: Creates content (blogs, SOPs) - training matters
3. Agentic: Autonomous, full tasks without human (87% time savings possible)

Business Model Shift

• Time & materials breaks with AI efficiency
• If 10-hour task takes 1 hour with AI, can't charge hourly anymore
• Must shift to fixed-price/value-based models

Critical Implementation

• ChatGPT Teams minimum for data privacy (not used for training)
• Weekly AI meetings: everyone brings solved problem
• Junior staff often lead - they expect AI as standard
• Start with: repetitive, low-hanging fruit, unenjoyable tasks

Watch Outs

• IP concerns: Unclear how data managed in LLMs, market tools vs. in-house risk
• Hallucinations: Makes up facts, adds incorrectly - always need human checkpoint
• Copyright: No clear rules yet on AI-assisted work ownership
• Companies building in-house AI fail 2x more often

The Bigger Picture

• AI replaces productivity (not just augments like PCs/smartphones)
• May see first billionaire solo company within generation
• Enterprise worried about AI-enabled startups eroding share
• Golden age for small businesses if played right
• Knowledge ≠ execution - AI can't replace human judgment/trust yet

Notable Quotes

• Rob: "Could you double revenue without increasing headcount? Yes, with AI."
• Caitlin: "95% of AI initiatives aren't hitting P&L."

Resources:

1. Deploy AI to improve your business, free your time, gain margins. Keystone Workshop - dates available in Q4.

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:

Profit vs. Sales

• "Sales is vanity, profit is sanity"
• Case study: $8M revenue, $1M debt, lost everything in pandemic
• Can scale revenue and still be broke; scale profits and never be broke
• Profit = freedom to reinvest or take distributions

Hidden Margin Killers

• Scope creep eating into margins
• Discounts in shaky economy
• Overstaffing/poor utilization
• Underpricing without SOPs/documentation
• Solution: Map delivery, cut non-value work

Three Pricing Models

1. Cost-Plus: Cost + margin = price (risk: high costs price you out, may not match perceived value)
2. Competitive/Market: Match market rates (risk: may not be profitable at market price)
3. Value-Based: Price on quantifiable value delivered (growing trend, requires outcomes focus)

When to Use Each Pricing Type

• Time & Materials: New/bespoke services, haven't done 10-50+ times, prevents eating surprise costs
• Fixed Fee: Only when predictable cadence, clear scope, supreme confidence in delivery at margin
  • Warning: One client lost $1M ($500K bid + $500K to complete) jumping to fixed fee too early

Time Tracking Essentials

• Time = inventory for professional services
• Can't manage margins/valuation without it
• Start simple: book time against jobs daily
• IoT timer device helpful for Gen Z/Alpha teams
• Review multiple times per week, not just monthly
• Update clients at 50%/80% milestones, not just month-end (avoids surprise bills)

Understanding True Value

• London Underground lesson: Problem wasn't late trains, it was not knowing when next train arrives
• The Mom Test: Don't ask "would you buy this?" (people lie). Ask "when did you last buy X? How much? What for?" (real data)
• Van Westendorp Method: 4 questions on price tolerance (too cheap, too expensive, + 2 middle) = pricing window

Value Stack Framework

• List all ways you create value
• Quantify each (target 3:1, 5:1, 10:1 value vs. fees)
• Show your work - explain why valid
• Price complaints = "not getting enough value for what I'm paying"

Outcomes-Based Pricing

• Use outcomes (plural), not single metric
• Define constraints upfront
• Don't wait longer than quarter to get paid
• Include qualitative measures (surveys, assessments)
• Run experiments to identify measurable outcomes

Critical Metrics

• Revenue per employee: $200K baseline, can reach $500K-$1M with AI
• EBITDA: What investors use for exit valuation
• AR aging: Delayed payments signal client satisfaction issues or financial trouble
• Keep books on accrual basis (not cash)

Process = Premium Pricing

• Study showed: Consistent clean delivery = customers pay 2-3x more vs. same outcome in poor process
• Clear, repeatable process = better pricing, margins, and client happiness

Notable Quotes

• Rob: "Time is inventory - can't manage without tracking it."
• Rob: "Price complaints mean 'not getting enough value for what I'm paying.'"
• Caitlin: "Consistent clean delivery = customers willing to pay 2-3x more."

Resources Mentioned:

• Finance for Founders (pricing chapter)
• Timeular Device
• Business Model Canvas (Strategyzer)
• The Mom Test (interview methodology)
• Van Westendorp Pricing Method
• Margin benchmarks

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:

Spotting Bandwidth Bottlenecks

• Obvious signs: Missed deadlines, quality issues, constant firefighting
• Subtle "energy leaks": Team disengagement, people stepping back, energy drops
• Catch energy issues before they impact client deliverables

Hiring Economics: Fractional vs. Full-Time

• Before hiring, check: Cash flow positive? Stable pipeline? Profit margin and runway?
• The math: If fractionals billing halftime at 3x hourly rate, full-time likely costs less
• Utilization targets: 75-80% for junior staff, max 85% (accounting for PTO)
• Bring in-house when: Core client-facing roles, IP development, culture representation needed
• Keep 1099 when: Behind-scenes work, specific deliverables, works independently

Cash Management Essentials

• Burn rate formula: (Cost of Revenue + Operating Expenses) ÷ 6 months = monthly burn
• Get line of credit at founding (best time to borrow: when you don't need it)
• Set your "squeal point" - how many months before making changes
• Without accountability, easy to think you're "one month away" indefinitely

Letting Go of Wrong People

• Case study: Employee with good delivery but high resistance, taking 10 hours/week of founder time
• Key question: "If those 10 hours could generate $1M in sales, is keeping them worth it?"
• Why founders struggle: Loyalty to early supporters, family/friends, falling in love with potential vs. outcomes
• The cost: Resentment builds, relationships damaged irreparably
• Solution: Present trade-offs clearly, let them opt in/out of new direction

Metrics & Accountability

• Define success upfront with clear measures
• Microsoft Education Competencies: Framework defining beginner to advanced performance by skill
• Pick 5 organizational + 3-5 role-specific competencies
• Professional services: 60% how people experience work, 40% outcomes

Building the Right Number Two

• Founder roles: Develop business, develop talent. That's it.
• COO role: Trains run on time, ensures delivery, has tough conversations with founder
• Must be truly empowered - no undermining their decisions
• Find complement to your strengths, not clone
• Long-term: COO often becomes CEO for premium exit

The Emotional Journey

• Founders operate in vacuums, need advisors who understand risk-taking
• Mastermind communities and experienced fractionals provide benchmarks
• No founder with great exit did it alone

Assessment Tools

• FinSight (Fintelligent): Financial data + recommendations, ~2 weeks
• VIP Audit (COO Pilots): Values/vision + team interviews + 30-60-90 plan, ~2 weeks, podcast listener rate

Notable Quotes

• Caitlin: "Energy leaks - you can see it as much in the output as in your people."
• Caitlin: "Founders confuse 'I'm busy' with 'I can afford someone.'"
• Caitlin: "If those 10 hours could generate a million dollar sale, would keeping this person be worth it?"
• Rob: "Founders have two roles: develop new business, develop talent. COO: trains run on time."

Resources Mentioned:

• FinSight Tool (Fintelligent) - Financial assessment
• Altitude 90™ Audit (COO Pilots) - Org health check and 30/60/90 roadmap to relieve pressure - Mention the podcast for $1,000 off
• Microsoft Education Competencies - Performance framework, example of Dealing with Ambiguity

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:

The CFO-COO Partnership

• Finance and operations are highly aligned in founder support work
• Issues often start in one area (messy books) and reveal needs in the other (operational improvements)
• Both hosts have served 200+ founders collectively, generating significant value ($20M+ for Caitlin's clients, $200-300M+ in exit value for Rob's clients)

Common Founder Challenges ("New Level, New Devil")

• Heroic effort syndrome: Working 60-80 hour weeks leading to burnout
• Fear of delegation: Either wrong people in seats or mental barriers to letting go
• Infrastructure issues: From brittle systems to shiny object syndrome
• Decision paralysis: Getting stuck at the whiteboard with too many options

Building Trust with Founders

• Communication through process: Keeping founders informed via notifications and regular updates
• Active listening: Asking open-ended questions rather than prescriptive solutions
• Understanding founder values: Aligning processes and team selection with core motivations
• Transparency: "Candor with kindness and challenging with intent"

The Scaling Challenge

• Founders must transition from "grit alone" to strategic delegation
• 80-90% execution by others is better than 100% founder execution at unsustainable hours
• A-players need empowerment to do their jobs effectively
• "Seagull management" (swooping in uninvited) kills team motivation

Key Metrics and Outcomes

• For Operations: Improved utilization rates, higher margins, better client retention
• For Finance: Clean books, clear metrics, path to exit valuation
• Rule of 40: Combination of growth rate and EBITDA percentage
• Valuation focus: EBITDA multiples and enterprise value optimization

Notable Quotes

• Caitlin: "You won't scale if you don't [delegate]. There's no path to being a scale by being a superhero."
• Rob: "100% of founders say 'I wish I'd done this sooner' after letting go and getting help."
• Caitlin: "New level, new devil" - each growth stage brings new challenges

Client Engagement Process

Both hosts emphasize:

• Audit-first approach: Understanding current state before recommending changes
• Custom 30-60-90 day plans: Tailored to specific business needs and opportunities
• Team interviews: Getting 360-degree feedback to build buy-in
• Quick wins: Demonstrating value within 30 days or less

This podcast is produced by Could Be Pretty Cool, an Atlanta-based media company amplifying creative voices through storytelling, strategy, and sound.

Coming September & October 2025

In this kickoff, Caitlin Ferguson (Founder of COOPilots.io) and Rob Ripp (Founder of Fintelligent & author of Finance for Founders) set the stage for a podcast built for founders who are scaling beyond grit alone.

You’ll hear what brought us together, why we’re passionate about guiding founders through the messy middle, and what to expect in upcoming episodes. Think real stories (names changed) from the trenches and practical tips you can use right away.

This isn’t another dry business lecture. We want you to feel like you're sitting down with two trusted peers over coffee. We’ll cover:

• How finance and operations fuel growth (and exits)

• Common mistakes founders make between $1M–$10M in revenue

• What “clean numbers” and “repeatable systems” really look like

• Why scaling without the stress is not only possible, but essential

If you’ve ever thought: “We’re growing, but I still feel stuck in the weeds" then this podcast is for you.

Subscribe here for updates and notifications when new episodes are released.