Profit First for Real Estate Investors with David Richter

David Richter
  • 5.0 (114)
  • Investing
  • Updated Semiweekly

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 instead of a step toward freedom.  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.

  1. 2d ago

    Joey Hart: Losing $50K on Deal One & Coming Back to Win $100K

    Joey Hart spent 25 years in corporate America as an engineer, product manager, and salesman before going all in on real estate as a HomeVestors "We Buy Houses" franchisee in early 2025. What makes his story different is that he ran Profit First from deal number one, before he ever made a mistake he'd need it to catch. In this episode Joey is refreshingly candid about a first deal that lost him over $50,000, a later flip that netted him around $100,000, and how a purpose bigger than money kept him steady through both. He breaks down his multiple-exit-strategy underwriting, how his CFO pushes him on gross margin targets, and why an engineer's risk-averse mindset made Profit First feel like a system that saves you from yourself. If you're eyeing the jump from corporate to real estate, this one is for you. Timeline Summary [2:04] – Why Joey left a lucrative corporate sales career to buy a real estate franchise [2:43] – His winding path from engineer to product manager to sales to house flipping [3:30] – Discovering franchising as a way to accelerate his rental portfolio goal [4:20] – Going all in because he couldn't build the business alongside a W2 [5:09] – Whether he regrets the leap, and the freedom and impact that answer it [6:19] – The expensive first deal bought at a meetup with everything pre-arranged for him [7:23] – Holding that property 13 months with budget overruns and a market shift [8:07] – Reframing a small fortune lost as an accelerated real estate education [10:29] – His current underwriting: evaluating every property with multiple exit strategies [11:49] – How his CFO pushed him from the 70% rule to real gross margin targets [13:28] – The flip where staging and opening a pool netted him around $100,000 [14:50] – What working with a CFO who knows real estate actually looks like [15:42] – Being challenged to take a paycheck and stop hoarding the profit account [17:37] – Running Profit First from day one after learning it in HomeVestors training [18:41] – Why the alternative was being out of business or never paying himself [21:03] – Building a cash flow projection to decide whether he can buy a house right now [23:23] – Adjusting to unpredictable income after decades of steady corporate paychecks [24:50] – What he had to unlearn, and the corporate skills that transferred over [27:35] – His advice: know how to run a business, not just do real estate deals [28:39] – Why you need a purpose beyond money to survive the hard times 5 Key Takeaways Start Profit First From Day One — Joey never ran his business any other way. Implementing the system before his first deal meant that when a deal went south, his cash was already where it needed to be.Underwrite Multiple Exit Strategies — Every property gets evaluated as a wholesale, a light cosmetic flip, and a full retail flip. Knowing the value of each exit keeps one bad deal from trapping you.A CFO Sharpens Your Numbers — His CFO moved him off a generic 70% rule to real gross margin targets and floors. Accountability from someone who knows your financials changes how you buy.Keep Losses In Perspective — A $50,000 loss on deal one and a $100,000 win later are both just part of the beast. If Joey had quit after the loss, he'd never have reached the win.Purpose Carries You Through — Chasing money alone won't hold you up when a deal costs you $50,000. A deeper why is what lets you trust the direction and keep going through the hard times. Links & Resources HomeVestors (We Buy Houses) — https://www.homevestors.comSimple CFO — https://simplecfo.comProfit First for Real Estate Investing Free Workbooks — https://peiworkbook.comProfit First for Real Estate Investing by David Richter — https://profitfirstrei.com Enjoyed This Episode? If Joey's honesty about losing $50,000 on his first deal and coming back from it gave you the nerve to keep going, that's exactly the point. Share this episode with someone weighing the jump from a corporate job into real estate, and follow the show and leave a rating and review so more investors can hear stories like this one.

  2. 5d ago ·  Bonus

    Profit First Chat: How to Prepare for A Downturn in Real Estate Investing | Solocast E33

    David Richter of Simple CFO opens this solo episode with a hard truth: downturns don't kill businesses, unprepared owners do. Drawing on the memory of the 2008 real estate collapse, he lays out how to build a business that survives whatever comes, whether it's a market crash or a personal emergency. This episode is a practical playbook for lean times, covering the cash system that names every dollar, the quarterly expense analysis that trims fat before you're forced to, and how to manage debt and vendor rates before they choke your cash flow. If you want to prepare proactively instead of scrambling reactively, this one gives you the moves. Timeline Summary [0:25] – The opening premise: downturns don't kill businesses, unprepared owners do [0:58] – Why businesses that only work when the sun is shining get stress tested and break [1:25] – It's not just market crashes: a personal downturn like a hospital stay can end a business too [1:44] – Preparation as part of your operating system, not your only focus [2:07] – Move one: have a Profit First system that gives every dollar a name [2:38] – Move two: manage expenses and know every dollar going out the door [3:02] – The quarterly expense analysis and how to run it [3:18] – The PRU framework: mark each expense profitable, replaceable, or unnecessary [4:05] – Why you should trim the fat when times are good, not when you're forced to [4:39] – Being proactive versus reactive with cutting costs [5:00] – Managing debt, including converting short-term loans to long-term when a flip becomes a rental [5:25] – Reaching out to creditors and vendors to negotiate rates down [5:42] – Leaning into what actually makes the real money, not what you think makes it [6:04] – The fix-and-flip trap of squeezing a deal that would've been better wholesaled [6:42] – The goal in a downturn is to survive, and preparation is what lets you thrive 5 Key Takeaways Preparation Is The Real Protection — Downturns don't sink businesses on their own; unprepared owners do. Build survival into your system before you need it, not after.Give Every Dollar A Name — A Profit First cash system tells you what you make, spend, and keep. When you know where every dollar goes, you can weather a lean stretch far better.Run A Quarterly Expense Analysis — Print your expenses every quarter and mark each one profitable, replaceable, or unnecessary. Cutting the unnecessary before a crisis is discipline, not desperation.Trim The Fat When Times Are Good — Anyone can cut costs in a downturn out of necessity. The disciplined owner leans out the business proactively while the going is still good.Manage Debt Before It Chokes You — Debt quietly drains cash, especially short-term loans on properties that became rentals. Refinance to long-term money and negotiate rates with creditors and vendors. Links & Resources Simple CFO — https://simplecfo.comProfit First for Real Estate Investing by David Richter — https://profitfirstrei.comGet your FREE Profit First for REI Workbook: https://pfreiworkbook.com/ Enjoyed This Episode? If David's line about trimming the fat when times are good made you want to pull your expense report right now, that's the proactive move that separates survivors from scramblers. Share this episode with an investor who only prepares once trouble hits, and follow the show and leave a rating and review so more real estate investors can build businesses that last through any cycle.

    Profit First Chat: How to Prepare for A Downturn in Real Estate Investing | Solocast E33

  3. Aug 10

    Adam Whitney: The Cash Conversion Cycle That Quietly Wrecks Flippers

    Adam Whitney spent over 20 years in the Marine Corps in military intelligence before going all in on real estate, and he brings that operator discipline to how he thinks about money. Now a leader at Seven Figure Flipping, he's a hardcore Profit First fan who built his personal money habits long before he built his business ones. In this episode Adam gets refreshingly honest about the mistakes, the down months, and the psychology behind keeping what you make. He covers his journey from a $9,000 first-year military salary through Dave Ramsey's envelope system to Profit First, why cash flow management is the most underrated skill in business, and how the OODA loop from fighter-pilot dogfighting applies to financial decisions under pressure. If you make money but still feel broke, this is one to hear. Timeline Summary [1:49] – The Freedom Award at Seven Figure Flipping's mastermind that measures freedom, not revenue [2:56] – Why community leaders have a responsibility to encourage growth for the right reasons [4:18] – Adam's 20 plus years in the Marine Corps and the money lessons operator discipline taught him [5:32] – Making $9,000 his first year and $14,000 his second in the military [6:13] – Taking a $41,000 tax-free combat bonus and the expensive wedding and truck that followed [7:28] – The 2008 cross-country drive during peak gas prices that shifted his money mindset [7:55] – Dave Ramsey's Total Money Makeover and the envelope system as his first fundamentals [9:02] – Discovering the FIRE community in 2016 and saving 50% of his income [10:41] – Building personal financial habits first, then learning he needed business ones too [11:05] – Hitting $1 million in gross profit but barely filling his bank account [11:28] – His mentor Bill Allen's non-negotiable rule: you must take money out of your business [12:23] – The tough-love line: if you can't manage $100, you'll never manage a million [13:26] – Why Profit First is really psychological, not just a system of bank accounts [17:22] – Telling a newer investor not to ask about allocations until he brings in revenue [18:30] – Restructuring Seven Figure Flipping when the model's margins tightened [19:32] – Cash flow as a river you must watch coming in, sitting, and going out daily [20:21] – Having to cut personnel when acquisition costs crept too close to deal value [21:36] – Learning cash flow management by studying his mentor Bill Allen's numbers mind [25:01] – Applying the OODA loop and commander's intent to business decisions under pressure [30:13] – The biggest blind spot: not understanding the cash conversion cycle 5 Key Takeaways Build Personal Habits First — Adam mastered his personal finances through Dave Ramsey and the FIRE movement before he ever fixed his business money. The foundation makes the business system stick.Profit First Is Psychological — The bank accounts work, but the real shift is mindset. Making money come off the top first is hard until you start, then it becomes how you operate.Cash Flow Is A River, Not A Snapshot — Your bank balance today isn't the picture. You have to watch what's coming in, what's sitting, and what's going out every single day.You Must Force Yourself To Get Paid — Bill Allen's rule is non-negotiable: take money out of the business or you'll work for free for years. Most owners who walk in the door aren't paying themselves.Understand The Cash Conversion Cycle — It can take 200-plus days from spending on marketing to collecting on a flip. Owners who don't plan for that gap create their own instability by shutting off marketing. Links & Resources Seven Figure Flipping — https://7figureflipping.comSimple CFO — https://simplecfo.comProfit First for Real Estate Investing Free Workbooks — https://peiworkbook.comProfit First for Real Estate Investing by David Richter — https://profitfirstrei.com Enjoyed This Episode? If Adam's honesty about down months and working for free hit home, you're far from alone, and that's exactly the point. Share this episode with an investor who's making money but still feeling broke, and follow the show and leave a rating and review so more real estate investors can build the habits that actually keep the cash.

  4. Aug 7 ·  Bonus

    Profit First Chat: Leverage vs. Cash-Flow (Which Wins in Real Estate Investing) | Solocast E32

    David Richter of Simple CFO tackles one of the biggest debates in real estate investing in this solo episode: leverage versus cash flow. His blunt take is that leverage won't make you rich, but it can absolutely make you broke, and the difference comes down to whether you have a system. Using the metaphor of leverage as fire, he explains how borrowed money can either refine and build your business or burn it to the ground. He covers the paper millionaire trap, how over-leveraging turns into an accidental Ponzi scheme, and why cash reserves are what let you handle more leverage safely. If you use other people's money to do deals, this one is worth your time. Timeline Summary [0:26] – The core claim: leverage won't make you rich but it can certainly make you broke [0:45] – Leverage as a springboard to wealth and the Bible verse about the borrower being servant to the lender [1:10] – How private money lets you take down a deal you couldn't fund on your own [1:29] – Using leverage to create income versus using it to create wealth [1:52] – The paper millionaire with a million in equity and nothing in the bank [2:33] – Why cash wealthy doesn't mean hoarding money but being smart with every dollar [2:58] – Where each dollar goes: paying yourself, reserves, reinvesting, and expenses [3:17] – Why leverage is dangerous because you can scale yourself out of business [3:41] – The fire metaphor and David's childhood house fire versus a bonding campfire [4:12] – What happens when lender A's funds run out mid-project [4:35] – How going to lender B to finish project A becomes the makings of a Ponzi scheme [4:56] – Why a reserve account lets you cover overages without lighting your hair on fire [5:20] – Cash reserves as your greatest asset and the signal that you can responsibly handle more leverage 5 Key Takeaways Leverage Is A Tool, Not A Guarantee — Borrowed money can be a springboard to wealth or the thing that breaks you. It multiplies whatever system you already have, good or bad.Equity You Can't Eat Isn't Wealth — A paper millionaire with no cash in the bank isn't truly wealthy. Real wealth means being able to transfer it into the real world when you need it.Leverage Is Fire — Handled well, it refines and builds your business. Handled carelessly, it burns everything down. The difference is knowing how to play with it.Over-Leveraging Becomes A Ponzi Scheme — When lender A runs out and you borrow from lender B to finish the same project, you're funding old obligations with new money. That cycle ends businesses.Reserves Let You Handle More Leverage — A cash reserve covers project overages without a scramble, and it signals to lenders that you manage money responsibly and can safely take on more. Links & Resources Simple CFO — https://simplecfo.comGet a FREE Profit First for REI Workbook at: https://pfreiworkbook.com/ Enjoyed This Episode? If David's take on leverage as fire made you rethink how you're funding your next deal, don't wait until you're borrowing from lender B to cover lender A. Share this episode with an investor who's scaling fast without a system, and follow the show and leave a rating and review so more real estate investors can learn to use leverage without getting burned.

    Profit First Chat: Leverage vs. Cash-Flow (Which Wins in Real Estate Investing) | Solocast E32

  5. Aug 5 ·  Bonus

    CFO Case Files: The Flipping Business That Lost Money for Two Years Without Knowing | Tommy Robinson | E16

    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 Your Books Are Your Scorecard — Unreliable books mean inconsistent owner pay, missed tax deadlines, and blind decisions. Clean, timely reporting is the foundation everything else is built on.A CFO Is A Financial Partner, Not A Bookkeeper — Tommy frames the role as advisor to the owner's decision, giving data-backed guidance while the owner still makes the call.Trust But Verify Your Bookkeeper — A client flew blind for months because her bookkeeper claimed work was done that wasn't. A CFO reviewing the numbers is what surfaced the gap.Segment Reporting Reveals Hidden Losses — Running the P&L by class showed a profitable-looking business was actually losing money on flips for two years while rentals carried it.KPIs Catch Overruns Before They Kill Margins — Deal-level flags on work in progress, budget, and timeline let flippers act proactively on carry costs instead of discovering losses after the sale. Links & Resources Simple CFO — https://simplecfo.comProfit First for Real Estate Investing Free Workbooks — https://peiworkbook.comProfit First for Real Estate Investing by David Richter — https://profitfirstrei.com 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.

    CFO Case Files: The Flipping Business That Lost Money for Two Years Without Knowing | Tommy Robinson | E16

  6. Aug 3

    Kirby Atwell: The 1% Net Rule That Changes How You Buy Short Term Rentals

    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 Cash Flow Beats Curb Appeal — A $234,000 two unit in Sioux Falls nets $2,500 a month while a $700,000 luxury cabin grossing the same amount can lose money. Buy for profit, not looks.Use The 1% Net Rule — Instead of 1% gross like the long term standard, Kirby targets 1% of purchase price in net profit after every expense. Small multi-units in secondary markets make it possible.Profit First Starts At Purchase — The system isn't just for managing cash. Kirby applies it to his buying formula so a deal has to hit the net number before he ever underwrites it.Clarity Enables Hiring — With over $1 million in the bank and no idea what was profit, he couldn't grow. Seeing where every dollar was designated is what let him build a remote team and step out of the day to day.Ten Properties Can Free You — Four Sioux Falls style deals at $2,500 a month hits $10,000 monthly and buys back 40 plus hours a week. For most of his students, that's the real financial freedom goal. Links & Resources Living Off Rentals Web Class — https://livingoffrentals.com/startSimple CFO — https://simplecfo.comProfit First for Real Estate Investing by David Richter — https://profitfirstrei.comProfit First by Mike Michalowicz — https://mikemichalowicz.com/profit-first 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.

  7. Jul 31 ·  Bonus

    Profit First Chat: Signs That You Need a CFO (even if you think you don’t) In Your Business | Solocast E31

    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 Lead With Total Honesty — A CFO relationship works only if you share what you actually want and where you're struggling. Hiding your money mindset just slows down the results you came for.A CFO Is Not A Bookkeeper Or CPA — Bookkeepers handle transactions and CPAs handle taxes. A CFO focuses on how money affects you, how much you keep, and the mindsets holding you back.Get Everyone On The Call — If a spouse or partner shares the finances, they belong on the early calls too. A reluctant participant who checks out undermines the whole engagement.Do The Groundwork First — Reading up on Profit First, balance sheets, and money psychology before you start means less foundation to lay. You get to clarity and better decisions faster.Bring Your Whole Finance Team — You're the conductor, so introduce your existing bookkeeper and CPA to your new CFO. Connecting the right people and systems makes the handoff seamless. Links & Resources Simple CFO — https://simplecfo.comProfit First for Real Estate Investing by David Richter — https://profitfirstrei.comThe Psychology of Money by Morgan Housel — https://www.morganhousel.comThe Art of Spending Money by Morgan Housel — https://www.morganhousel.comAccounting for the Numberphobic by Dawn Fotopulos — https://www.harpercollinsleadership.com 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.

    Profit First Chat: Signs That You Need a CFO (even if you think you don’t) In Your Business | Solocast E31

  8. Jul 27

    Caylee Robles: How to Pay Yourself Consistently on Sporadic Real Estate Income

    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 Treat Yourself Like a Business Owner — Whether you're an agent or an investor, you're self-employed, and that means acting like it. An LLC, a business checking account, and dedicated tax and owner's pay accounts come before anything else.Set Up the System Before the Money Arrives — Caylee opened her Profit First accounts while she was broke, so when the $90K hit there was already a place for every dollar. The foundation matters more than the timing.Risk Your Time, Not Your Money — She left investing for the agent side on purpose. A canceled listing costs her hours, while an overleveraged flip can cost an investor six figures at inspection.Automation Removes the Willpower Problem — Money hits her Relay account and splits instantly: credit cards paid, SEP IRA funded, salary scheduled. She only touches the system when she overspends.A Buffer Buys You the Power of No — With six months of runway in the business, a slow summer doesn't create panic. Financial cushion is what turns "what do I need to do" into "what do I want to do next."Links & Resources Simple CFO — https://simplecfo.comFollow Caylee Robles on Instagram — https://instagram.com/thedailycayleeRelay business banking — https://relayfi.comProfit First by Mike MichalowiczEnjoyed 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.

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About

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 instead of a step toward freedom.  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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