Business Lunch Podcast Summary

Episode: The CFO Reality Check Every Entrepreneur Needs: Leading Through the Numbers
Host: Roland Frasier (with Ryan Deiss)
Date: December 11, 2025

Episode Overview

In this episode, Roland Frasier and co-host Ryan Deiss dive into a topic many entrepreneurs avoid: the reality of accounting, finance, and the critical relationship with your CFO. They pull back the curtain on common pitfalls founders encounter when interpreting financial reports, address how accounting can influence company culture and decision-making, and offer actionable advice for ensuring your finance team empowers — not hinders — your leadership.

Roland and Ryan share candid personal stories, memorable frustrations, and strategies for transforming accounting from a source of dread into a tool for growth and strategic clarity. They emphasize the importance of accurate, actionable reporting, understanding the limitations of accounting data, and not letting finance “wag the dog” of the business.

Key Discussion Points & Insights

1. Why Entrepreneurs Avoid Accounting (00:13–05:42)

• Roland’s Frustration with Accounting Reports:
  • Their companies received daily financial reports for over ten years that painted a consistently negative (and inaccurate) picture — ignoring expected income and only showing outflows.
  • Reports did not factor in recurring revenue, accounts receivable, or savings.
  • Roland shares:

    “Not only did it not include the income that was expected and historical, but it didn't tell me… what I could do about anything. So it was just basically an exercise in depression.” ([04:12])

  • Result: He started ignoring reports, which is unhealthy for leadership.

Notable Quote

“If we're looking at a horror show every single time you look at the email or the financials, then ultimately you're going to be negatively reinforced to the point where you just don’t.”
— Roland Frasier ([13:13])

2. The Mindset Disconnect: Optimism vs. Realism (05:42–09:54)

• Entrepreneurial Optimism: Ryan notes entrepreneurs are naturally positive and risk-tolerant, while accountants feel obligated to present "worst case" scenarios.

• Finance as Foil: The goal should be balance—not only optimism nor only doom and gloom.

  “If it's only doom and gloom, if it's only the worst possible version of the story, not only is it incredibly depressing… but it's also inaccurate.”
  — Ryan Deiss ([05:42])

• Responsibility: Business owners must partner with finance to produce numbers that are understandable, accurate, and actionable.

3. When Finance Becomes a Bottleneck (09:54–13:32)

• Avoiding Accountability:
  • Both admit to sidestepping unhelpful finance team members or systems, which is “lazy and irresponsible.”
  • Leadership must either support their team to level up or find replacements.
• Finance Intimidation:
  • Entrepreneurs often let finance people dictate the process, even if reports aren’t meaningful.
  • Ryan:

    “You, accounting finance person, need to figure out how to bridge the gap between what is and what I need. That is your job. And if you can't do it, you can't occupy this seat.” ([10:23])

• Team Alignment:
  • Members should prioritize the company/leadership team’s needs over personal or departmental preferences.

4. Creating Empowering Financial Reporting (13:32–17:35)

• Positive, Gamified Reporting:

  • Reports should incentivize leadership to look at them and drive improvements.
  • “It's empowering to know if you are in trouble. But if it's all the bad and none of the good… you will disincentivize yourself and your team to even look at the information.” — Roland Frasier ([13:32])

• Quarterly Review & Purging Data/Meetings:

  • Assess reports and meetings for continued usefulness; cut what’s no longer helpful.
  • “If you find you miss it, add it back. More times than not, you will never miss it.”
    — Ryan Deiss ([16:52])

5. Upgrading to Professional Accounting (18:10–23:23)

• Shifting from Cash to Accrual Accounting:
  • In preparing for a potential business exit, they hired a CFO, FP&A expert, and Controller.
  • While expensive, this level of reporting is crucial for increased business valuation.
  • Side effect: Side-by-side comparisons of cash vs. accrual statements led to panic (“down 70% in profit”) — but the reality was simple accounting differences.

Notable Quotes

“The important thing is… be sure that you’re looking apples to apples.”
— Roland Frasier ([21:32])

• Recommendation:
  • If shifting accounting methods, recalculate previous years using the new method to create comparability.

6. The Impact of Accounting Assumptions & Contract Structure (23:23–31:12)

• Revenue Recognition Nuances:
  • Accrual accounting changes when and how revenue is counted, especially for long-term services.
  • Smart contract structuring can allow for more timely revenue recognition — dramatically impacting apparent profitability.
• Challenging Accountants’ “Musts”:
  • Roland discusses reworking contract terms to allow 85% current revenue recognition vs. only 15%, massively affecting cash flow and apparent profit.

  “When your accountant or finance team comes and says we’ve got to do it this way, think about the business case for it.” ([29:57])

  • Don’t default to accountant’s preferences—ask why and push for solutions that serve the business.

7. Evaluating Financial Reports — Asking the Right Questions (31:12–39:00)

• Dig Deeper, Line by Line:

  • If presented with alarming financials, review large discrepancies item by item with your team to understand root causes.
  • Establish whether differences are due to methodology, timing, or actual underperformance.

• Business Case vs. Legal Necessity:

  • Ask: Is this “required by law/GAAP/tax authorities,” or simply preferred by accounting? If the former, comply; if the latter, weigh the business need.
  • “There’s a massive, massive gap between ‘this is something you absolutely, positively have to do’ and ‘this is something you probably should do’. And that gap is called what’s the business case?” — Ryan Deiss ([32:40])

• Open-Book Management Cautions:

  • Most owners don’t fully understand finance, so don’t expect employees to; avoid creating panic through poorly interpreted numbers.

8. Cash Flow — The Underappreciated Metric (37:51–41:30)

• Three “Books” to Monitor:

  • GAAP/accrual, tax accounting, and actual cash flow all present different realities—know and monitor each appropriately.

  “When you want to see can I pay my bills as they come due from the cash that I will have available, that's when that cash flow statement is really, really critical.” — Roland Frasier ([38:06])

• Company Structure Implications:

  • Profits can shift between entities for legitimate business reasons; understand these moves and ensure clarity at the consolidated level.

9. Final Advice & Mental Models (41:30–43:21)

• Keep Asking “What Would Have to Be True?”

  • Challenge the black-and-white thinking of some finance professionals—seeking alternatives can yield better business outcomes.
  • “What would have to be true for that to be different in this way that I want things to be?”
    — Roland Frasier ([42:26])

• Ownership and Agency:

  • No matter your financial sophistication, keep asking questions, seek second opinions, and don’t defer all authority to accounting.

  “If you're not satisfied with the answers you’re getting, keep asking questions… Don’t just settle for somebody telling you something that doesn't make sense to you. You're smarter than you think you are.”
  — Ryan Deiss ([41:30])

Memorable Moments & Quotes With Timestamps

• On Unhelpful Financial Reports:

  “So it was nothing but depressing... it was basically an exercise in depression.”
  — Roland Frasier ([03:43])

• On the Need for Balance:

  “If it’s only doom and gloom… not only is it depressing… it’s inaccurate.”
  — Ryan Deiss ([05:42])

• On Taking Ownership:

  “You, accounting finance person, need to figure out how to bridge the gap between what is and what I need. That is your job.”
  — Ryan Deiss ([10:23])

• On Data Overload:

  “More data is not necessarily a good thing. And if you're getting data that's causing you to take bad actions… there's a problem with the report.”
  — Ryan Deiss ([15:16])

• On Comparing Apples to Oranges:

  “Be sure that you’re looking apples to apples when you go through something like this...”
  — Roland Frasier ([21:32])

• On Creating Business Cases:

  “That gap is called what's the business case? And it is your job as the CEO, as the business owner. You don't have to know all the answers, but you need to say this is the business case that we're looking to achieve.”
  — Ryan Deiss ([32:40])

• On Open-Book Management:

  “Most owners themselves don't understand their finances well enough themselves, and yet they somehow have to educate with confidence their entire team…”
  — Ryan Deiss ([34:12])

Key Takeaways

• Don’t let accounting dictate business direction without challenge and understanding.
• Financial reports must be actionable, accurate, and not solely negative.
• Educate yourself — challenge your finance team, and focus on business goals.
• Understand differences between cash, tax, and accrual accounting.
• Regularly review which reports and data are useful, and purge what isn’t.
• When shifting methods (e.g., cash to accrual), create comparable historical data for apples-to-apples review.
• Leverage the “What would have to be true?” question to break out of limiting finance assumptions.

Timestamps of Important Segments

• [00:13] — Why Discuss Accounting? (Framing the episode)
• [03:43] — Impact of Negative-Only Reporting
• [05:42] — The Mindset Disconnect: Entrepreneurs vs. Accountants
• [10:23] — Pushing Back on Unhelpful Finance Norms
• [13:13]/[13:32] — Empowering Financial Information
• [16:25] — Eliminating Unnecessary Reports
• [18:10] — Transitioning from Cash to Accrual & Upgrading the Finance Team
• [21:32] — Apples-to-Apples: Comparing Accounting Methodologies
• [29:36] — Strategic Revenue Recognition
• [32:40] — “What's the Business Case?” Decision-Making
• [38:06] — Importance of the Statement of Cash Flows
• [41:30] — Closing Advice: Agency, Inquisitiveness, and “What would have to be true?”

This summary captures the essence, actionable advice, and candid tone of Roland Frasier and Ryan Deiss, providing both context and granular insight for business owners navigating the world of finance.