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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.
Timeline Summary
[0:44] – Christina welcomes Tommy back and introduces the Case Files format built around real client scenarios
[1:46] – Tommy's background across financial analyst, controller, VP of finance, and CFO roles
[2:33] – Why Profit First is about changing how owners think, not just bank accounts
[3:13] – What Tommy loves most about training new CFOs and learning from their varied backgrounds
[5:02] – Why the team model protects clients when a CFO takes vacation or leave
[6:26] – The standardized dashboard and shared notes that let any CFO step in seamlessly
[7:14] – Getting personal: Tommy's family, four children, three grandchildren, and monthly dinners
[7:36] – His volunteering and an upcoming mission trip to Peru to build houses
[9:14] – The client who raved about Tommy to David Richter at a conference
[11:29] – Why client success depends on the client doing the homework and buying in
[12:37] – The starting point: unreliable books, debt, and taxes filed late with penalties
[13:05] – Building debt schedules, implementing Profit First, and transitioning to Simple CFO bookkeeping
[13:53] – Quarterly expense and vendor analysis to check every dollar for profitability
[15:01] – The real transformation: decisions made with confidence instead of anxiety
[17:52] – Why the best time to bring on a CFO was yesterday, and the second best is now
[19:16] – How a trusted CFO catches a bookkeeper who isn't actually doing the work
[22:36] – The big surprise: a flipping business that lost money for two years while rentals carried it
[24:27] – Building deal-level KPIs to vet ARV, budget, timelines, and contractors before buying
[24:52] – How project overruns in cost and time were quietly killing margins through carry costs
[25:34] – The work-in-progress dashboard with flags that trigger proactive action
[26:25] – Turning three years of flip losses into a year-to-date profit for 2026
5 Key Takeaways
Links & Resources
Enjoyed This Episode?
If Tommy's story about a flipping business quietly losing money for two years made you wonder what your own segment reports would reveal, that's worth a closer look. Share this episode with a real estate investor who's never separated their flips from their rentals on paper, and follow the show and leave a rating and review so more investors can find these Case Files.
Kirby Atwell runs Living Off Rentals and has coached nearly 400 students to build cash-flowing short term rental portfolios over the past five years, alongside his own 43-property portfolio. A profit-first practitioner who lives on a farm with his family, he applies the system to how he buys properties, not just how he manages the cash.
This episode breaks down Kirby's unusual 1% net rule, why the highest-cash-flowing property beats the prettiest one, and how small multi-unit properties in secondary markets outperform luxury cabins. If you want to build a short term rental portfolio or squeeze more profit out of the one you have, this conversation is packed with tactical detail.
Timeline Summary
[1:24] – Kirby returns to the show with nearly 400 students coached over five years of short term rental teaching
[2:18] – Why he'd rather buy the highest cash flowing rental than the prettiest one
[3:03] – The 500 million Airbnb bookings most investors overlook beyond the luxury vacation cabin
[4:21] – A real deal breakdown: a $234,000 two unit in Sioux Falls netting around $2,500 a month
[5:32] – How the same property performs as a long term rental and why that matters as a backup
[6:09] – Why all 43 of his properties could convert to long term tomorrow and still cash flow
[7:38] – Kirby's 1% net rule and how it differs from the standard 1% gross rule for long term rentals
[9:03] – Netting 1% of purchase price after every expense including maintenance set asides
[10:39] – What his accounts looked like before Profit First when he had over $1 million and no clarity
[11:42] – Using the free spreadsheet and the caps versus taps distinction every first and fifteenth
[13:20] – His actual percentages across an active income LLC and a rental property entity
[15:20] – How Profit First clarity coincided with outsourcing the day to day of the business
[16:24] – Going from a stretch goal of 30 properties to listing his 43rd while working less
[16:50] – Growing organically into four full time Philippines-based team members instead of a property manager
[19:18] – The typical first goal for students: 10 to 15 thousand a month to escape a full time job
[24:49] – The fastest Profit First move for an owner drowning in their own properties
5 Key Takeaways
Links & Resources
Enjoyed This Episode?
If Kirby's 1% net rule made you rethink every short term rental deal you've looked at, don't keep buying the pretty cabin that loses money. Share this episode with an investor who's killing themselves cleaning their own properties, and follow the show and leave a rating and review so more real estate investors can build portfolios that actually pay them.
David Richter, author of Profit First for Real Estate Investing and founder of Simple CFO, walks through how to onboard a fractional CFO the right way so the relationship pays off from day one. He explains what makes a CFO relationship different from working with a bookkeeper or CPA and what both sides need to bring to the table.
This solo episode covers the prep work that gets you clarity faster, why every relevant person on your finance team belongs in the process, and how being honest about your money mindset shapes the whole engagement. If you're about to bring on a CFO or thinking about it, this one shows you exactly what to prepare and what to expect.
Timeline Summary
[0:26] – David sets up the episode on how to make your CFO relationship the best right off the bat
[0:44] – The difference between onboarding well and just showing up unprepared
[1:08] – Why total honesty during onboarding matters more with a CFO than any other money person
[1:26] – How a CFO relationship differs from a bookkeeper's transactions or a CPA's tax focus
[1:47] – The reluctant spouse problem and why all relevant people need to be on the early calls
[2:24] – Book recommendation on money mindset from Morgan Housel for anyone struggling with it
[2:59] – Accounting for the Numberphobic for owners intimidated by balance sheets and P&Ls
[3:16] – Doing the groundwork yourself so less foundation has to be laid during onboarding
[3:38] – Bring your existing bookkeeper and CPA into the process to make the handoff seamless
[4:16] – You're the orchestra conductor, so connect the right people to the right systems
[4:32] – Why owners avoid looking at finances most when money is tightest
[4:54] – Telling your CFO how you actually feel about money instead of hiding it
[5:10] – What the CFO should be doing: prepping you, starting where you are, asking good questions
[5:47] – Why the relationship has to be two sided, a yin and yang, not one person pouring in
[6:05] – Facing hard things, building reserves, and putting systems in place for better decisions
5 Key Takeaways
Links & Resources
Enjoyed This Episode?
If this gave you a clear picture of what to prepare before your first CFO call, put it to work before you sit down with anyone. Share this episode with a business owner who's been avoiding their finances, and follow the show and leave a rating and review so more real estate investors can build the kind of money relationship that actually keeps them in control.
Caylee Robles is a retired CPA turned Florida real estate agent who spent five years earning her accounting credentials at the University of Wisconsin before walking away from Deloitte to chase real estate. After six months without a paycheck, a $90,000 wholesaling run, and two years of raiding her own tax account, she built a Profit First system that now pays her a salary every 1st and 15th and could carry her through six months of zero income.
David Richter and Caylee dig into why agents stay trapped in feast or famine, why she deliberately chose the lower risk agent path over investing, and the exact account structure that let her double three years of income in a single year. If you're a real estate agent or investor whose commissions land straight in your personal checking account, this episode is your wake-up call.
Timeline Summary
[0:33] – David sets up the episode: thinking like a business owner and building systems that keep more of your money
[1:15] – Caylee shares her backstory: decided at age eight to become an accountant, earned her CPA at the University of Wisconsin
[2:39] – Within a month at her first accounting job she knew she hated it, searching real estate jobs every night during busy season
[3:43] – Where her "do hard things" wiring came from: two parents in sales who worked 25 years before the payoff
[6:07] – The three year transition out of accounting: Deloitte auditing, a real estate internship, and an Austin transfer that closed the door
[7:42] – Underwriting $1 million plus luxury leased homes across the Caribbean, Mexico, and South Florida
[8:08] – Joining New Western at the end of 2022: "you eat what you kill," 75 to 80 hour weeks, and two months with no income
[9:39] – Six months without making a dollar, then $90,000 in three months wholesaling with her partner
[10:10] – Setting up her LLC and Profit First accounts on Relay before the money ever showed up
[11:49] – The two year struggle: pulling from her tax account to pay personal credit cards during the lean stretch
[13:38] – The 2025 turning point: repeat client business and splits big enough that she never touches her owner's distribution account
[16:38] – Her S corp structure: salary every 1st and 15th, SEP IRA contributions, and distributions on top
[17:19] – In 2025 she doubled what she made in the three prior years combined, and 2026 has already matched it
[21:25] – Why agent risk beats investor risk: her downside is time, while investors she works with have $300,000 on the line
[23:21] – Diversifying beyond real estate: 401k, SEP IRA, joint investments, and a 3% interest rate home that becomes a rental
[29:59] – Her one move to make this week: set it up as a business with an LLC and dedicated business accounts
5 Key Takeaways
Links & Resources
Enjoyed This Episode?
If Caylee's story of going from raiding her tax account to a self-paying salary every two weeks hit close to home, don't keep it to yourself. Share this episode with an agent or investor whose commissions are still landing in their personal checking account. Then follow the show and leave a rating and review so more real estate professionals can find Profit First.
David Richter, author of Profit First for Real Estate Investing and founder of Simple CFO, makes a blunt case in this solo episode: if you don't have a real reserve strategy, you don't have a real business. He walks through why most investors drain their accounts chasing the next deal and what that costs them a decade in.
This episode reframes cash reserves as a growth tool rather than money sitting idle, covering how lenders view financial stability, why you should grow from reserves instead of revenue, and how one Profit First implementation gave a business owner six months of reserves for the first time in his life. If you're closing deals but living deal to deal, this one is for you.
Timeline Summary
[0:26] – The opening claim that a business without a reserve strategy isn't a real business
[0:48] – Why real estate investors resist reserves and prefer every dollar out in deals
[1:09] – Draining accounts for deals may scale you fast but won't build something that lasts
[1:46] – Reserves as fire prevention instead of endless firefighting in your business
[2:11] – The mastermind line that convicted David: if you're always fighting fires, you're the arsonist
[2:35] – Without systems and people, you're constantly behind the eight ball on cash decisions
[2:54] – The three questions you can't answer without a system: reinvest, pay yourself, or taxes
[3:12] – Living deal to deal instead of paycheck to paycheck and what that does over ten years
[3:29] – Why Profit First is fundamentally a reserve strategy for knowing where every dollar goes
[4:05] – What lenders actually want to see and why zeroed out accounts kill your credibility
[4:22] – Becoming the fire preventer instead of the firefighter through a clear cash system
[4:43] – You took the chance on yourself, so the business should give you financial freedom
[5:12] – Grow from your reserves, not from your revenue, and stop recycling the top line
[5:33] – Where to find Profit First and the real estate investing edition David wrote
[5:49] – A business owner who implemented one teaching and built six months of reserves
[6:07] – Reserves as both financial peace of mind and a tool for profitable growth
5 Key Takeaways
Links & Resources
Enjoyed This Episode?
If the line about being the arsonist in your own business landed a little too close to home, that's the wake up call. Share this episode with an investor who's still draining their accounts for every deal, and follow the show and leave a rating and review so more real estate investors can build reserves that actually protect them.
Zach Richards is a private lender and co-founder of REI Capital Guys, who made his first private loan in July 2020 using $100,000 of his own savings while still working a software job. He now runs a lending fund with his business partner, doing loans across the country while living rurally in New England, keeping bees, and volunteering with mountain search and rescue.
This episode covers how to break into private lending, how lenders structure deals differently than banks, and how to put idle capital in your Profit First tax and reserve accounts to work. If you have money sitting on the sidelines in a savings account, an old 401(k), or an IRA and you want it working harder, this conversation is for you.
Timeline Summary
[1:43] – Zach's background and why private lending appealed more than managing tenants
[2:28] – The nightmare tenant in his duplex that soured him on rentals for good
[3:10] – Three to four months of books, attorneys, and local meetups before ever lending a dollar
[3:37] – His first deal in July 2020, a $100,000 loan to an experienced flipper that paid back in six months
[4:44] – Why a good attorney on your loan documents is the difference between safety and disaster
[5:29] – Zach admits the $100,000 was the bulk of his savings and how he talked himself into it
[6:31] – How private lenders beat banks on speed by lending against the asset, not your tax returns
[6:52] – His actual terms: 80% of purchase, 100% of repairs, up to 65% to 70% of ARV
[7:43] – Why relationships matter so much that repeat borrowers get a yes over text
[8:46] – The mental shift from a stable W2 paycheck to lumpy business owner cash flow
[10:38] – The software engineer who had to force himself to build relationships instead of hiding in numbers
[11:37] – Why he and his partner merged two separate lending companies to launch a fund
[13:17] – The partnership secret: a disagreement is usually a different route to the same goal
[18:17] – Whether you should move Profit First tax and reserve money out of low-yield bank accounts
[19:13] – The liquidity rule: don't buy property with tax money, but shorter-term lending can work
[21:04] – Why a borrower with a Profit First system looks more organized and more likely to execute
[22:17] – What he's seeing in the market with properties sitting 30 to 45 days instead of selling overnight
[24:08] – When to get into private lending and how to lend from a self-directed IRA or HELOC
5 Key Takeaways
Links & Resources
Enjoyed This Episode?
If Zach's story about turning $100,000 in savings into a private lending fund got you thinking about the money sitting idle in your own accounts, don't let it keep collecting dust. Share this episode with an investor who's been curious about getting on the lending side of the table, and follow the show and leave a rating and review so more real estate investors can find these conversations.
David Richter of Simple CFO has talked with thousands of entrepreneurs about their finances, and he keeps running into seven-figure real estate businesses operating with no QuickBooks file, no spreadsheet, and no numbers at all. In this solo episode he lays out what real-time financial reporting actually looks like and why stale numbers wreck your decisions.
If your books close 30 or 60 days late, you're steering your business by gut feeling instead of data. This episode covers how fast your reporting should really be, the red flags that tell you your bookkeeper doesn't know real estate, and the specific things every investor should be checking on the balance sheet, P&L, and cash flow statement.
Timeline Summary
[0:26] – The core premise: if your reporting is 30 days old, your decisions are 30 days wrong
[0:53] – A real client story of numbers arriving 60 days late and being wrong when they did
[1:31] – Seven-figure businesses running with no QuickBooks, no spreadsheet, not even numbers on a napkin
[2:12] – What good reporting actually is: it helps you make a decision
[3:04] – Why entrepreneurs lose sleep at night, and it's not because they're losing money
[3:48] – The realistic reporting timeline: weekly or bi-weekly, monthly at the absolute latest
[4:08] – Internal bookkeepers should deliver in 1 to 5 days, third parties in 5 to 15, never over 30
[4:32] – Red flag number one: your bookkeeper doesn't understand the real estate industry
[5:17] – Red flag number two: as the owner, you don't know what to look for
[5:36] – Balance sheet basics: negative asset or liability accounts are always a warning sign
[6:22] – Why an in-progress fix and flip on your P&L instead of the balance sheet is a red flag
[7:00] – Red flag number three: not tracking your actual cash movement
[7:22] – Breaking down the cash flow statement and its three activity categories
[7:42] – The gap between a $50,000 P&L profit and a $5,000 bank balance
[8:42] – Gut feeling can get you to seven figures in revenue but won't let you keep it
[9:39] – Why Profit First works as a simplified cash flow statement that names every dollar
5 Key Takeaways
Links & Resources
Enjoyed This Episode?
If David's rundown of balance sheet red flags made you want to pull up your own books right now, that's the point. Share this episode with an investor who's still running on gut feeling, and if it gave you a new perspective on your numbers, follow the show and leave a rating and review so more real estate investors can stop guessing and start deciding.
David Richter and Christina Gutierrez, co-hosts of the Profit First for Real Estate Investors podcast and business partners at Simple CFO, break down why the "cash is king" mantra fails so many real estate investors. Between them they've coached hundreds of investors and business owners who make good money yet still feel broke.
This episode challenges conventional financial wisdom head-on: cash isn't king, and neither is cash flow. It's cash flow management that actually builds wealth, and this conversation is for any real estate investor or business owner who closes deals but never sees money left at the end of the month.
Timeline Summary
[1:19] – David and Christina open the episode and tee up their controversial take that goes against standard financial wisdom
[1:45] – The core argument: cash is not king, cash flow is not king, cash flow management is what actually matters
[2:05] – Why investors with rental cash flow can still feel broke and "good broke" on paper
[2:53] – Christina reframes Profit First as a cash management tool, not accounting
[3:12] – The real danger of "cash is king" is letting your cash control you by dipping in whenever you want
[3:47] – David's realization: without a system, cash controls you no matter how much you have in the bank
[5:15] – Comparing the Cashflow 101 game by Robert Kiyosaki to escaping the financial rat race
[6:09] – Christina on teaching money lessons to their kids and the "Bank of Daddy" habit
[7:36] – Parkinson's Law and the toothpaste effect: spending expands to fill available cash
[9:15] – Why controlling your money is a learnable skill, not something you're born knowing
[10:01] – The difference between cash management thinking and knowing where numbers sit on a statement
[11:20] – Demystifying the CFO title and reframing it as a "chief financial partner"
[13:36] – The hospital analogy: bookkeeper as nurse, CPA as surgeon, CFO as private doctor
[14:30] – Why Simple CFO built tiered levels so fractional CFO help is attainable at any size
[15:04] – Bad money habits at six figures only get magnified at seven figures
[19:39] – Final case study: a client who paid down debt and got systems in place to stay out of trouble
5 Key Takeaways
Links & Resources
Enjoyed This Episode?
If David and Christina's take on why "cash is king" keeps investors stuck hit home, you're not alone. Share this episode with a fellow investor who's closing deals but still wondering where all the money went, and if you're serious about keeping more of your profit, follow the show and leave a rating and review so more real estate investors can find it.
David Richter of Simple CFO breaks down one of the most practical questions real estate investors avoid: how to actually pay yourself first instead of paying everyone else and their mother. Drawing on the Profit First formula, he walks through the exact system for setting owner's pay when your income is unpredictable.
This solo episode swaps the broken "sales minus expenses equals profit" model for the wealth formula and shows you how to build an owner's comp account that pays you consistently. If you're a real estate investor closing deals but feeling guilty about taking money out and wondering where all the cash went, this one is for you.
Timeline Summary
[0:26] – David opens with the hard truth that your business might be paying everyone except the person who built it
[0:47] – Why the standard "sales minus expenses equals profit" formula keeps owners stuck in a rat race
[1:40] – Waking up a decade into your business asking where all the money went
[2:03] – The Profit First wealth formula flipped: sales minus profit equals expenses
[2:23] – Why so many owners feel guilty taking money out of their own business
[2:40] – Breaking down the three required components: sales, profit, and expenses in the right order
[3:17] – The pay-yourself-first principle from Rich Dad Poor Dad and Robert Kiyosaki
[3:36] – Lessons from The Richest Man in Babylon and The 7 Habits on putting first things first
[3:57] – What margin actually means and why it's your financial safety buffer
[4:32] – The simplest first step: open a separate owner's comp bank account today
[5:02] – A real example of splitting $10,000 in income into consistent owner's pay
[5:21] – Why the "black hole" single bank account keeps you from ever getting paid
[6:15] – Building personal stability so the entrepreneurial roller coaster doesn't shake you
[6:40] – Why an owner's comp account matters most when a spouse or family depends on you
[7:05] – Finding your two key numbers: what you need and what you want
[9:11] – Advice for W2 earners: build 6 to 12 months of reserves before making the jump
5 Key Takeaways
Links & Resources
• Simple CFO — https://simplecfo.com
Enjoyed This Episode?
If David's owner's comp account idea got you rethinking how you pay yourself, don't keep it to yourself. Share this episode with a fellow investor who's paying everyone but themselves, and if it gave you a new perspective, follow the show and leave a rating and review so more real estate investors can build real financial clarity.
In this Simple CFO Case Files episode, we go inside the actual client work with Chris Savor, a Simple CFO who's been with the team since April 2022 and manages some of the firm's largest client relationships. Rather than talk about the methodology in the abstract, this conversation pulls back the curtain on how a CFO actually diagnoses a real estate business, cleans up the books, and turns a cash-negative operator into a profitable one. Chris walks through his "battle plan" approach, the short-medium-long framing he uses in the first 60 days, and why financial clarity is the single biggest result he delivers.
The heart of the episode is two client transformations. One is a large operator with 65 properties and a thousand doors who'd been cash-flow negative for eight months because of misconfigured allocations, fixed to cash-positive inside the first 30 days. The other is a flipper who went from 20 flips a year making nothing to 200 flips and paying himself $600,000 annually, with a real reserve position and a tax strategy that wiped out three years of tax bills. It's a grounded, practical look at what a dedicated financial partner actually changes in a real estate business.
Timeline Highlights
[0:00] Intro to the Simple CFO Case Files series and what makes it different
[0:23] Host welcomes Chris Savor and his background as a CFO since April 2022
[2:01] Chris on who he works with: flippers, multifamily, short- and long-term rentals
[2:55] The single biggest result Chris delivers: financial clarity for lost owners
[4:29] The battle plan call and getting real about the good, the bad, and the ugly
[5:35] Short, medium, and long phases all wrapped into the first 60 days
[6:01] What separates Simple CFO from a typical accountant: a genuine personal partnership
[8:41] Laying the financial foundation, cleaning up books, and rolling out Profit First
[10:32] Case one: a 65-property, thousand-door operator cash-negative for eight months
[11:01] Finding misconfigured allocations on day 28 and clawing back overspending
[12:24] Getting the operator cash-positive and onto a salary for the first time
[12:45] Why the Profit First book alone isn't enough without a specialist implementing it
[14:26] Inside the CFO dashboard: profit-on-the-shelf and the 13-week rolling cash view
[16:41] How automated, daily-updated sheets replace manual QuickBooks report pulling
[16:57] Using the forecast every meeting to close the gap to a net-profit goal
[19:52] Case two: a flipper who had no idea whether he was making money
[20:34] The first three moves: cleanup, real estate–specific books, and mapping the money
[21:05] From 20 flips a year making nothing to 200 flips and real profit
[22:12] Building reserves from 1% up to 6%+ and getting the owner onto a real paycheck
[23:22] Using a tax strategy with land easements and bonus depreciation to erase three years of tax
[24:22] The full transformation recap: from lost and unpaid to $600K a year
[26:09] Chris's words of wisdom: you're not alone, it can be fixed, don't go at it solo
Key Takeaways
Links & Resources
Closing
Chris's clients prove the same thing over and over: you're not alone, and it can be fixed. The operators who win are the ones willing to roll up their sleeves and fight the battle alongside a partner who actually knows the terrain. If you're staring at deposits and withdrawals with no idea whether you're making money, that's exactly the problem Simple CFO exists to solve. If you're ready to bring clarity and structure to your business finances, visit profitrei.com to apply for a free financial discovery call with the team.
From the publisher's feed
Real estate investors work hard, make great money, and still feel broke, but it’s not your fault. Without a simple system, cash slips through the cracks and every next deal feels like a lifeline…
That’s why David Richter, author of Profit First for Real Estate Investors with a foreword by Profit First founder Mike Michalowicz, created this podcast to reveal how real investors flipped the script and started paying themselves first. Each episode shares honest stories from investors who used Profit First to eliminate stress, build stability, and reclaim their lives.
If you’re ready to stop surviving and start thriving, this is where your financial clarity begins.

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