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Balancing an active-duty military career with building a nationwide real estate business requires ruthless systems, automation, and elite decision-making frameworks. In this episode, Marcus Crigler sits down with Marine Corps veteran Keith Gillespie to discuss how he scaled a multi-state real estate operation while being deployed 13 times overseas.
Keith breaks down the OODA Loop (Observe, Orient, Decide, Act), a military framework that eliminates analysis paralysis and accelerates entrepreneurial problem-solving. You will also learn why paying for 57 different mentors shortcuts his learning curve, how to properly vet a business coach based on how well they diagnose your constraints, and why investing heavily in customer support is the ultimate key to a successful B2B or coaching business.
Listen and enjoy the show!
You’ll Learn How To:
What You’ll Learn in This Episode:
(4:05) Why military veterans thrive in real estate through fast information processing
(13:21) Breaking down the OODA Loop, by knowing how to observe, orient, decide, and act without freezing up
(22:42) Why paying 57 different coaches saved him years of trial and error
(26:07) Why customer support and client experience are the ultimate pillars of a successful business
(27:43) How to find the right mentor by studying what they have done rather than what they are doing now
(6:51) The power of beginning with the end in mind and tracking your P&L on a weekly basis
Who This Episode Is For:
Why You Should Listen:
If an active-duty Marine can build a real estate business across 34 states while working just one hour a day on deployment, anyone can build a systemized company with the right frameworks. This episode delivers masterclass insights on decision-making, speed of execution, and the true value of investing in high-level mentorship.
Connect with Keith Gillespie:
Connect with Marcus Crigler:
Failing to implement a proactive tax strategy before your business begins generating massive revenue guarantees that you will overpay the IRS by hundreds of thousands of dollars. In this episode, Marcus Crigler and Kaden Hackney break down their foundational "Entrepreneur Tax Strategies", the exact entry-level system they use to shelter income and build wealth for real estate investors before advancing to high-level tax planning.
Kaden details the multi-layered filter required to correctly set S-Corp compensation, explaining how your W-2 wage directly dictates your ability to max out Solo 401(k) contributions and unlock the 20% Qualified Business Income (QBI) deduction. You will also learn the IRS-compliant rules for hiring your children, how to utilize the Augusta Rule to rent your home to your business tax-free, and why paying state taxes through your S-Corp bypasses the $10,000 federal deduction cap.
You’ll Learn How To:
What You’ll Learn in This Episode:
(5:51) Why waiting until you are making millions to implement a tax strategy destroys your wealth
(12:25) The S-Corp Compensation Filters (Balancing compliance, retirement accounts, and QBI)
(15:23) How your S-Corp wages dictate your Qualified Business Income (QBI) deduction limit
(19:41) The IRS rules and documentation required to legally hire your children and avoid tax fraud
(23:44) How to shift $16,100 of income to your child tax-free and fund their Roth IRA
(26:04) Utilizing the Augusta Rule, home office deductions, and Pass-Through Entity (PTE) tax elections
Who This Episode Is For:
Why You Should Listen:
Paying $380,000 in taxes because you did not know the rules is a completely avoidable wealth killer. This episode provides the exact foundational tax strategies required to keep your cash flow in your pocket, optimize your S-Corp structure, and lay the groundwork for massive, tax-sheltered wealth building.
Connect with Marcus Crigler & Kaden Hackney:
Many real estate investors have accumulated massive equity through recent property appreciation, only to find their actual monthly cash flow wiped out by skyrocketing taxes, doubling insurance premiums, and unpredictable maintenance costs. Being rich on paper does not pay the bills when your rental portfolio barely breaks even, and traditionally, selling the properties meant triggering massive capital gains taxes.
Marcus Crigler sits down with Wood Speed, a multi-generational real estate entrepreneur and the head of the Rental Conversion Program at Colonial Funding. Wood details exactly how landlords can transition from fixing toilets to acting as the bank by seller financing their underperforming rental properties. He explains how to underwrite borrowers to Non-QM standards to ensure your note is a sellable asset, how to increase your return on equity from 4% up to 10%, and how to maintain liquidity by either selling your note on the secondary market or using it as collateral for a line of credit.
You’ll Learn How To:
What You’ll Learn in This Episode:
(4:02) Wood’s multi-generational history of pivoting from traditional landlording to seller financing
(8:44) Why massive property appreciation is destroying landlord cash flow through hidden taxes and insurance
(13:37) How to sell an encumbered property without triggering Due-on-Sale clauses
(17:48) Why a 10% yield on a seller-financed note beats a 4% cap rate on a rental
(23:00) Why the Mortgage Credit Availability Index drop created prime seller-finance buyers
(29:29) How to create liquidity without selling the property by borrowing against your newly created mortgage notes
Who This Episode Is For:
Why You Should Listen:
If your rental portfolio looks great on a balance sheet but generates zero actual cash flow after taxes and maintenance, this episode offers a proven exit strategy. You will learn how to turn dead equity into a consistent, passive 10% yield by acting as the bank, entirely eliminating the headaches of property management while maintaining your liquidity.
Connect with Wood Speed:
Connect with Marcus Crigler:
Many real estate entrepreneurs celebrate record top-line revenue, only to find less cash left in their bank account at the end of the month. Scaling transaction volume without financial discipline inevitably leads to ballooning overhead, unchecked marketing waste, and compressed profit margins.
In this episode of Strength in Numbers, Marcus Crigler and co-host Kaden Hackney introduce the "NOI Rhythm", a proven operational framework designed to protect and grow your Net Operating Income (NOI) percentage as your business expands. They break company expenses into three distinct buckets, Marketing & Advertising, General & Administrative (G&A), and Human Capital, and assign each a specific review cadence.
You will learn how to evaluate monthly marketing spend by channel to reallocate dollars toward winning campaigns, how to conduct quarterly vendor audits to eliminate software bloat and renegotiate pricing, and why Q4 is the critical window to align employee compensation with company financial targets.
You’ll Learn How To:
What You’ll Learn in This Episode:
(2:21) The Profit Dilemma and why scaling top-line revenue often leads to shrinking take-home cash
(7:34) Organizing business overhead into three core buckets (Marketing, G&A, and Human Capital)
(11:05) The Monthly Rhythm and evaluating marketing spend trends and cost-per-channel metrics
(15:37) The Quarterly Rhythm and auditing vendor lists, scrubbing subscriptions, and renegotiating contractor fees
(18:43) The Annual Rhythm and restructuring team compensation plans and establishing Q4 budgets
(24:10) Why scheduling non-negotiable financial reviews separates true entrepreneurs from gamblers
Who This Episode Is For:
Why You Should Listen:
Scaling deal volume without an operational financial rhythm is a fast track to working harder for less profit. This episode provides an actionable roadmap to actively control expenses, maintain lean overhead, and maximize your retained wealth across every stage of business growth.
Connect with Marcus Crigler:
While most real estate investors are exclusively focused on acquiring more doors, savvy entrepreneurs are discovering that buying boring businesses can offer higher margins, less competition, and massive tax benefits. In this episode of Strength in Numbers, Marcus Crigler sits down with Jon Ostenson, founder of FranBridge Consulting, to unpack why non-food franchising is becoming the ultimate bolt-on strategy for real estate operators.
Jon explains why he strictly avoids saturated markets like food and cleaning, and instead focuses on highly fragmented, needs-based industries like insulation, dumpsters, and septic services. You will learn how to leverage the "ROBS" program to buy a business entirely with your retirement account (tax-free), how to utilize SBA loans to fund 90% of your startup costs, and why Section 179 depreciation on massive equipment fleets allows some investors to effectively launch their franchise for free.
You’ll Learn How To:
What You’ll Learn in This Episode:
(0:00) Beginning of today’s episode
(3:20) Why franchising offers a built-in tech stack, marketing system, and mastermind of existing owners
(4:33) Why real estate investors should avoid food franchises and buy boring businesses like dumpsters or septic services
(9:50) How to step back from day-to-day operations by hiring a strong operator
(10:45) Typical franchise costs and how to leverage SBA loans for 80% to 90% of the initial capital
(13:54) How a $200,000 investment can generate a 75% annual return
(15:44) How Section 179 depreciation on massive equipment fleets can effectively fund your entire franchise down payment
(18:28) How to use the ROBS program to fund 85% of your business purchase using your existing retirement account
Who This Episode Is For:
Why You Should Listen:
Buying an existing independent business often takes years of searching and extreme due diligence. This episode reveals how partnering with a proven, non-food franchise allows you to instantly step into a fragmented market, apply professional white-collar management to a blue-collar industry, and utilize aggressive tax depreciation to accelerate your wealth.
Connect with Jon Ostenson:
Connect with Marcus Crigler:
Is it really worth paying 5% to 10% of your rental income to a property management company, or should you just manage your portfolio yourself? In this episode of Strength in Numbers, Marcus Crigler sits down with Kelly Stanaway, co-president of Fertig and Gordon, a firm managing over 1,500 properties in one of the most heavily regulated markets in the country, Los Angeles County. Kelly details her journey of taking over her family's property management business during the chaos of COVID-19, losing her accounting staff, and being forced to learn the granular financial operations that her father had previously ignored.
Kelly pulls back the curtain on how a successful property management firm actually turns a profit, and it isn’t just from management fees. She explains why bringing maintenance in-house generates nearly twice the income of standard management fees and why creating cafeteria-style service options allows owners to stay involved without getting overwhelmed. You will learn the critical difference between asset management and property management, the hidden value of outsourcing habitability issues in tenant-friendly states, and why knowing your laws and your numbers is the ultimate key to surviving real estate regulations.
You’ll Learn How To:
What You’ll Learn in This Episode:
(0:00) Beginning of today’s episode
(2:20) How Kelly inherited and eventually bought out her family's property management business in LA County
(3:34) Why syndicators with Limited Partners (LPs) must control both asset management and property management
(6:51) The danger of being a CEO who ignores the day-to-day accounting numbers of their business
(9:51) Why property management is two completely different businesses (serving people and reconciling accounting)
(12:13) How to stop treating property management like a dime-a-dozen business and start charging for your value
(15:53) Why bringing maintenance services in-house generates almost twice the income of standard management fees
(18:55) The hidden cost of strict local regulations (e.g., HVAC temperature mandates, balcony inspections, and rent control)
(20:55) Navigating rent collection and commercial delinquencies during the COVID-19 moratoriums
(23:40) How to offer cafeteria-style property management for hands-on owners who only need partial support
(26:10) Why paying a 5% to 10% management fee is worth avoiding a multi-million dollar tenant lawsuit
Who This Episode Is For:
Why You Should Listen:
Property management is notoriously viewed as a dime-a-dozen industry, leading many operators to race to the bottom on pricing. This episode provides a masterclass on how to actually build a highly profitable property management business by knowing your numbers, insourcing maintenance, and providing unmatched value through regulatory expertise.
Connect with Kelly Stanaway:
Connect with Marcus Crigler:
When managed correctly, debt is one of the most powerful tools for accelerating real estate wealth. When mishandled, it acts as an anchor that will capsize everything you've built. In this episode of Strength in Numbers, Marcus Crigler demystifies the polarizing topic of debt, explaining exactly when you should leverage it and when it becomes a toxic liability.
Marcus introduces the Debt Matrix, a clear framework for categorizing your liabilities into productive, unproductive, necessary, and lifestyle buckets. You'll learn the difference between good debt (debt that pays for itself) and bad debt (debt that drains your net worth), and why even necessary personal debt like your mortgage or car loan is technically stunting your financial growth.
Listen and enjoy the show!
You’ll Learn How To:
What You’ll Learn in This Episode:
(0:00) Why you should never take out debt to fund lifestyle purchases like a Rolex
(0:39) Why debt is like a knife and a tool that creates opportunity but can quickly ruin you
(1:45) The exact definition of Good Debt (and why it must be tied to income generation)
(2:20) Why your personal mortgage and auto loans are technically Bad Debt
(3:11) The Four Categories of Investing (Productive, Unproductive, Necessary, and Lifestyle)
(4:39) Using HELOCs or home equity to fund high-risk stock trades
(5:45) Why determining whether to stay lean or scale large requires custom forecasting and KPIs
Who This Episode Is For:
Why You Should Listen:
Debt is the ultimate financial multiplier, it multiplies both your wins and your losses. If you are operating without a clear philosophy on when and why you take on debt, you are relying on luck rather than strategy. This episode provides a grounded, math-based framework to help you analyze every liability on your balance sheet so you can intentionally build long-term wealth without taking on unnecessary risk.
Connect with Marcus Crigler:
It is easy to get trapped in a cycle of funding a luxury lifestyle before you actually have the wealth to support it. In this episode of Strength in Numbers, Marcus Crigler introduces the Investment Matrix, a powerful framework to help you categorize your assets and stop lifestyle creep from eroding your net worth.
Marcus breaks down the difference between productive investments (assets intended to create more assets) and unproductive investments (assets intended to create more lifestyle). You will learn why most people get stuck funding their daily lives and skip straight to funding their luxury lifestyle, completely bypassing the crucial wealth-building phase.
You’ll Learn How To:
What You’ll Learn in This Episode:
(0:00) Why you must earn your lifestyle through wealth building rather than taking a detour to it first
(2:30) The definition of productive vs. unproductive investments
(3:20) The definition of necessary vs. unnecessary investments
(4:30) Examples of productive and necessary investments (401ks, real estate, and businesses)
(5:35) Why your cars, houses, and cash reserves are classified as unproductive but necessary
(6:55) The danger of parking your money in unproductive and unnecessary lifestyle assets like Rolexes and vacation homes
(9:55) Why tracking your wealth every single quarter spurs action and drives financial change
Who This Episode Is For:
Why You Should Listen:
If you stay on the unproductive and unnecessary side of the investment matrix, you are doomed to a life of constantly striving for wealth but never achieving it. This episode provides the exact mental and financial tools required to stabilize your living expenses, focus on wealth-generating assets, and ultimately earn the lifestyle you desire.
Connect with Marcus Crigler:
Many real estate investors treat their rental portfolios as set-it-and-forget-it investments, only to realize years later that their properties are draining cash rather than building wealth. In this episode of Strength in Numbers, Marcus Crigler breaks down the essential wealth-building fundamentals that most operators completely overlook.
From cultivating deep lending relationships and mastering the mechanics of debt to avoiding the trap of "asset-class hopping," Marcus shares insights gathered from managing the backend financials of hundreds of high-performing real estate businesses. You'll also discover how to actively manage a supposedly "passive" portfolio using a quarterly Real Estate Owned (REO) schedule to maximize your true return on equity.
You’ll Learn How To:
What You’ll Learn in This Episode:
(0:00) Why chasing whatever asset class is "hot" destroys long-term wealth
(0:53) Lessons from reviewing the backend financials of hundreds of real estate portfolios
(1:42) The relationship game: Why lender networking is a mandatory operational requirement
(2:36) Studying debt: Why understanding interest structures, swap rates, and bridge loans matters
(3:35) The asset class trap: Why real estate is a broad category, not a single asset class
(4:57) The real reason every investor must learn how to raise private capital
(5:46) The oxymoron of wealth: Why passive portfolios must be actively managed
(6:34) How an REO (Real Estate Owned) schedule reveals your true return on equity
(7:53) Dialing in conversion metrics and fundamentals when the market shifts
Who This Episode Is For:
Why You Should Listen:
Passive real estate investing does not mean passive management. If you don't understand the debt instruments you sign or monitor how your equity is performing across every property you own, your assets will quietly turn into liabilities. This episode provides the exact financial playbook needed to analyze your holdings, optimize your lending, and build real estate wealth with intention.
Connect with Marcus Crigler:
Are you still running your real estate business out of a single LLC or Sole Proprietorship? Have you started throwing rental properties into your flipping S-Corp to save on paperwork? If so, you are laying a foundation that could trigger hundreds of thousands of dollars in irreversible tax penalties.
In this episode of Strength in Numbers, Marcus Crigler and Kaden Hackney reveal the devastating entity structure mistakes that consistently blow up real estate investors' tax bills. They break down the Optimized Entity Structure, explaining exactly when a wholesaling business should switch to an S-Corp, the lethal danger of holding long-term rentals in an S-Corp, and why simple legal maneuvers to achieve anonymity can accidentally trigger massive tax events.
Listen and enjoy the show!
You’ll Learn How To:
What You’ll Learn in This Episode:
(0:00) How a simple LLC structure maneuver cost an investor hundreds of thousands in taxes
(5:50) The IRS deadlines you must know for fixing your entity structure before year-end
(8:59) Why moving properties between entities for legal protection often triggers massive, irreversible tax bills
(13:27) Why operating as a Sole Proprietorship forces you to pay a 15% self-employment penalty
(17:19) When exactly you should elect S-Corp status (the $50k to $100k rule)
(18:27) How to correctly funnel your income using W-2 wages and K-1 distributions to dodge self-employment tax
(19:22) Why holding rentals in your active flipping entity gets you slapped with Dealer Status and ruins your 1031 exchanges
(21:13) Why your real estate losses get trapped and cash-out refinances become taxable
(25:32) How an IRS clerical error saved an investor with $10 Million in an S-Corp from absolute disaster
Who This Episode Is For:
Why You Should Listen:
Entity structure is the foundation of all real estate wealth. If your foundation is cracked, no advanced tax strategy will save you. If you are buying, selling, or holding real estate in an entity structure you chose by default, you are likely overpaying in taxes or setting a trap that will lock up your equity. By listening to this episode, you will learn how to structure your active and passive businesses exactly like the wealthy do.
Connect with Marcus Crigler:
From the publisher's feed
Strength in Numbers with Marcus Crigler is the #1 podcast for real estate entrepreneurs who make good money but struggle with cash flow, tax planning, and building real wealth. If you're tired of…

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