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SIMPLE CFO

CASE FILES

SIMPLE CFO CASE FILES PODCAST

Episodes

  • Christina Gutierrez talks with CFO Michael Hansen

Business Debt vs Personal Debt: Why the Difference Matters

August 26, 2026

In this CFO Case Files episode, Christina Gutierrez sits down with CFO Michael Hansen, one of the earliest team members who joined right as David Richter's book launched, when Simple CFO had just 13 or 14 clients. Based in Oregon and deeply operations-focused, Michael brings a perspective most finance people don't: the conviction that most money problems are actually operational problems showing up in the bank account.

Michael walks through a real client turnaround, a husband-and-wife team running a school rather than a real estate business, and how he led with trust, tackled the shame around their debt, and separated business debt from personal debt before ever touching the financials. He and Christina dig into why operations that never scale with revenue create leaks, why expense analysis is the most emotionally charged conversation, and why he focuses on daily and weekly cash before cleaning the books. If you want to see how a CFO actually thinks, this one delivers.

  • Christina Gutierrez talks with Tommy Robinson

The Flipping Business That Lost Money for Two Years Without Knowing

August 5, 2026

In this Simple CFO Case Files episode, Christina Gutierrez sits down with CFO and CFO trainer Tommy Robinson, who brings over 20 years of real estate finance experience as a former financial analyst, controller, and VP of finance. Tommy breaks down two real client turnarounds from inside the business.

He walks through a client who came in with unreliable books, significant debt, and late tax filings, and how the team rebuilt her financials into clean, project-level reporting she can trust. He also shares a flipping and rental operator who discovered their flipping business had quietly lost money for two years while the rentals carried it. If you want to see what a fractional CFO actually does day to day, this one delivers.

  • Featured Posts

Stop Living Deal to Deal

Many real estate investors live deal to deal without realizing it. They generate plenty of revenue, but never build lasting financial security.That is not financial freedom. It is a stressful cycle th... ...more

Cash Flow ,Profit

September 03, 20267 min read

Stop Living Deal to Deal

How to Build a CFO Relationship That Actually Improves Your Business

You can hire the smartest financial expert in the world. You can give them access to every report you have. But if you hide your concerns, skip meetings, or leave key decision-makers out of the conver... ...more

cfo

August 26, 20267 min read

How to Build a CFO Relationship That Actually Improves Your Business

If You Don’t Have a Reserve Strategy, You Don’t Have a Stable Real Estate Business

Money hit the bank account. Bills got paid. You funded the next property, covered payroll, and handled a few expenses that had been waiting. Then you looked at the account... And most of the money was... ...more

Cash Flow ,Profit First Budgeting &Profit

August 19, 20267 min read

If You Don’t Have a Reserve Strategy, You Don’t Have a Stable Real Estate Business

If Your Financial Reports Are 30 Days Behind, Your Decisions Are 30 Days Wrong

Many real estate investors are making major decisions with old, inaccurate, or incomplete financial reports. Some do not receive their reports until 30 or 60 days after the month ends. Others have rep... ...more

Cash Flow ,Budgeting Profit &Bookkeeping

August 12, 20267 min read

If Your Financial Reports Are 30 Days Behind, Your Decisions Are 30 Days Wrong

Stop Building Everyone Else's Wealth First

You closed another deal. The rent checks came in. The rehab sold. The wholesale assignment funded. So where did all the money go? If you're like most real estate investors, you already know the answer... ...more

Cash Flow ,Budgeting Profit &Owner Pay

August 05, 20267 min read

Stop Building Everyone Else's Wealth First

Profit Isn't an Accident

No matter how good you are, you can't see through walls. The investors who thrive aren't the ones who avoid surprises. They planned for them before they ever made an offer. That's why building enough ... ...more

cfo ,Cash Flow Budgeting &Profit

July 29, 20267 min read

Profit Isn't an Accident
  • Christina Gutierrez talks with David Richter

Why Making a Million Means Nothing If You Kept Nothing

July 1, 2026

In this Simple CFO Case Files episode, David Richter and his business partner Christina Gutierrez kick off a new recurring series recorded right after their weekly EOS same page meeting. They pull back the curtain on how they run Simple CFO using Gino Wickman's Traction and EOS system, and why the visionary and integrator partnership has been the engine behind the business.

The heart of the conversation is one recurring phrase they hear from real estate investors who walk through their door: "I wish I would have known this." David and Christina break down why so many owners stay stuck asking CFO level questions of bookkeepers and CPAs who can't answer them, what a fractional CFO actually does that's different, and how to become a master of your money without ever becoming a master of accounting. If you're flipping houses or holding rentals and you can't say what you actually kept last year, this episode points you toward the clarity you've been missing.

  • Christina Gutierrez talks with CFO Tony Castronovo

The MCA Trap That Was Costing One Business $30,000 a Month

June 24, 2026

Tony Castronovo is a Simple CFO fractional CFO who has worked with nearly 50 clients across real estate investing and small business ownership. In this second appearance on the show, Tony joins host Christina Gutierrez to walk through a string of five-star client reviews and unpack the real stories behind them — the financial messes, the predatory debt, the overleveraged portfolios, and the moments when a third-party lens changed everything for a business owner.

This episode is a case study deep dive. From a three-pronged real estate and hard money operation that needed entity restructuring to a fiber construction company bleeding $7,000 a week to MCA lenders to a multifamily investor with a highly leveraged portfolio that needed property-by-property triage, Tony breaks down exactly how Simple CFO approaches each situation, why the CFO relationship only works when clients show up ready to collaborate, and what separates a bookkeeper from a financial partner who actually moves your business forward.

  • Christina Gutierrez talks with David Richter

The Apprenticeship Model That Replaces Coaches, Mentors, and Expensive Mistakes

June 17, 2026

What if the entrepreneurial principles you spent your 20s and 30s learning the hard way — accountability, financial literacy, win-win thinking — could be baked into your kids' education from the very beginning? David Richter shares the story of how a conversation at a real estate investor mastermind led his family to discover Acton Academy, a nontraditional school with an entrepreneurial framework so aligned with how he runs his business that they eventually moved across the country to enroll their daughter.

This episode isn't a sponsored segment — it's a genuine recommendation from someone who watched his six-year-old come home and propose a win-win negotiation without ever being taught the term. From peer accountability contracts and level-based progression to real-world apprenticeships and early financial literacy, David breaks down what makes Acton different and why the principles behind it translate directly to how successful investors build teams, hire by core values, and think about the next generation.

  • Christina Gutierrez talks with Pete Richter

The Financial Clarity You Think You Have Isn't Real

June 10, 2026

What happens when a father believes so much in what his son built that he becomes a paying client — not a cheerleader, not a silent supporter, but someone who put his own business on the line to test whether the system actually works? That's the story of Pete Richter: property management veteran, former client of Simple CFO, and now a fractional team member helping the company he once hired. Host Christina Gutierrez sits down with Pete for a conversation that's part case file, part origin story, and completely worth your time.

Pete ran a property management firm with roughly 300 doors, was in the early stages of a fix-and-flip operation, and had the same problem most real estate business owners have — the financials were technically being tracked, but nothing was clean, nothing was separated, and nobody could tell with confidence whether the business was actually making money. David Richter, founder of Simple CFO and Pete's son, stepped in as both a son and a service provider. What followed was a transformation in financial clarity, accountability, and business operations — and eventually, a role on the team for the man who saw David's potential before anyone else did.

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