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Grounds for Growth: Coffee with the C-Suite

Grounds for Growth: Coffee with the C-Suite

By: Grounds for Growth
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Grounds for Growth

Real Laughs. Real Lessons. For Founders Who Want to Scale Without the Stress.

Hosted by Caitlin Ferguson (Founder of COOPilots.io & Experienced COO) and Rob Ripp (Founder of Fintelligent, Author of Finance for Founders, & Experienced CFO), Grounds for Growth is the candid coffee chat every founder wishes they had.

Between them, Rob and Caitlin bring 40+ years of experience, 200+ founders served, and $200M+ in exits supported. Each episode blends stories from the trenches with actionable frameworks that founders can use right away.

Topics range from:
☕ AI & automation (and what actually moves the P&L)
☕ Profitability & pricing (no more scaling revenue while staying broke)
☕ Building the right team at the right stage
☕ Preparing your company for exit — even if you’re not selling yet
☕ The founder bottleneck (and how to get out of your own way)

It’s equal parts wisdom and laughter: you’ll hear war stories of financial disasters, messy ops, surprising wins — and walk away with tools to avoid the mistakes most founders make.

Copyright 2025 All rights reserved. Economics Leadership Management & Leadership
Episodes
  • Episode 3: Right Team at the Right Time

    Episode 3: Right Team at the Right Time
    Oct 14 2025

    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
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    42 mins
  • Episode 2: The Ugly Truth About Your Numbers and Operations

    Episode 2: The Ugly Truth About Your Numbers and Operations
    Oct 7 2025
    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 Bank Loan Crisis: Founder's bank called a loan worth hundreds of thousands of dollars due to messy booksBalance sheets had negative numbers and didn't balanceRoot cause: Bookkeeper attempting CFO-level work (wrong person in wrong role)Rob's team cleaned up books in 30 days and recapitalized the debtKey lesson: Don't make your bookkeeper your CFO - completely different skill sets The Four-Page P&L Problem: Charts of accounts with 400+ line items (one nonprofit example: separate account for "bicycle purchases")Founders create new accounts for every transaction typeSolution: Organize by things you can control and measure, not every transaction variationExample: Combine all state payroll taxes into one parent category instead of 20-30 separate accounts Understanding Financial Roles (Critical Distinctions) Bookkeeper: Follows processes, keeps books, doesn't analyzeAccountant: Trained in GAAP, manages accrual-based books, makes journal entriesController: Chief Accounting Officer - ensures accurate statements, tells you what happened yesterday/todayCFO: Strategic advisor, tells you what's happening tomorrow, builds enterprise value, presents tradeoffs and options Investment Guidelines by Revenue Stage: Sub-$1M: $500-1,000/month for basic bookkeeping$1-2M+: $1,500-2,500/month for robust accounting servicesScaling companies: $7,500-10,000/month for virtual CFO ($250+/hour)Critical threshold: At $1-2M revenue targeting $5-10M, invest seriously in financial infrastructure The Shocking $200K Labor Cost Discovery Case Study Breakdown: Started with four-page P&L, founder thought 80% gross margin (actually 50-55%)Reality: 50% staff utilization + $200K/year on subcontractorsTranslation: Over $1M/year paying people not working on clients, plus $200K for outside helpSolution: Shifted subcontractor work to underutilized staffResult: Saved $200K immediately, nearly doubled owner's income The $800K Meeting Problem (Same Company): Spending $800,000/year on internal meetingsStaff using 15-20% of time (full day per week) in meetings, not client workCombined with PTO/holidays: Only 50-60% effective utilizationCore issue: Billables not generating enough revenue to cover overhead and profit Critical Metrics for Professional Services Must-Track Numbers: Labor costs as % of revenue: Should be ~50% (many are 67%+)Utilization rate: Target 75-85% (from 2,080 hours/year baseline minus PTO)Revenue per employee: Key indicator - growing this means more work with fewer peopleGross margin: Must know true cost of goods sold The Time Tracking Imperative: Caitlin won't take clients without hourly dataTime is inventory for professional servicesCan't value business for exit without knowing true marginsStandard: Use 2,080 hours/year (40 hrs/week × 52 weeks) as baseline Founder Mental Blocks Around Labor Costs Three Common Excuses for Not Cutting Staff: "Pipeline is coming" - Keeping people "at the ready" for deals that might close"Loyalty factor" - Can't fire brother-in-law/early team/friend "No benchmark" - Don't know what utilization/margins should be for industry/stage The Solution: Bring in industry benchmarks by company stageMap processes end-to-end to identify what actually drives client valueValidate with client interviewsEliminate non-value-adding activities (often significant time sinks) Process Optimization & AI Integration Value Delivery Mapping: Founders often lose sight of how they drive value for clientsMap entire process to identify wasted activitiesExample impact: Collapse 6-month engagements to 2 months by cutting unnecessary stepsBenefits: Faster time-to-value = more referrals + retained clients AI Opportunities: Document methodology, values, SOPs, frameworks into central prompting documentsMaintain brand consistency through AI-assisted workNew challenge: Restructuring roles between "senior work" (human) and "junior work" (AI-assisted)Result: Instant cash flow improvements within weeks Modern Financial Reporting What Reports Should Include: Financial statements (P&L, balance sheet, cash flow)Trend analyses (revenue, cash flow, profits)Historical comparisonsBudget vs. actual12-month forecastingKey performance metrics dashboard Red Flags Your Financials Need Help: P&L is 4+ pages longRelying on bank balances as success measureUsing 8+ spreadsheets to update books monthlyCan't state labor costs as % of revenueDon't know gross marginNot using accrual-based accountingEmailing financial statements (outdated) Notable Quotes Caitlin: "Time to value matters to clients. All you had to do was stop doing stuff that didn't matter."Rob: "Revenue per employee - if it's growing, you're getting more work done with less people."Rob: "Don't make your bookkeeper your CFO - very different skill sets." Resources Mentioned: Fintelligent.com -...
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    34 mins
  • Episode 1: New Level, New Devil (TM)

    Episode 1: New Level, New Devil (TM)
    Sep 29 2025

    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.
    Show More Show Less
    35 mins
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