Episodes

  • Captive Insurance Companies

    Captive Insurance Companies
    Jun 3 2026
    A captive insurance company is owned and controlled by the business it insures, allowing the parent to deduct premium payments as ordinary business expenses while underwriting profits accumulate inside the captive on a tax-advantaged basis. Under Section 831(b), small captives pay tax only on investment income — not premiums — up to a statutory threshold of $2.85M for 2025. But captive insurance is a risk management tool first and a tax tool second: structures built in reverse draw IRS scrutiny and lose in court. This episode covers what genuine compliance looks like, how recent Tax Court decisions and 2025 IRS regulations define the line between legitimate and abusive structures, and what documentation and actuarial standards are non-negotiable.
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    7 mins
  • Opportunity Zones & Capital Gains Deferral

    Opportunity Zones & Capital Gains Deferral
    Jun 3 2026
    Opportunity Zones allow investors who realize capital gains to reinvest those gains into a Qualified Opportunity Fund within 180 days, deferring the original tax liability and eliminating all federal gains on appreciation inside the fund after a 10-year hold. Made permanent by the One Big Beautiful Bill Act in July 2025, the program now includes 3,309 newly designated rural opportunity zones offering a 30% basis step-up — triple the standard rate. This episode walks through the holding period mechanics, the 2026 recognition deadline that many early investors are navigating now, and how sophisticated families are evaluating fund quality, liquidity tolerance, and tax timeline coordination to capture the full benefit.
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    7 mins
  • Qualified Small Business Stock (QSBS)

    Qualified Small Business Stock (QSBS)
    May 27 2026
    Section 1202 of the tax code allows eligible founders and early investors to exclude up to $15 million in capital gains from a business exit — entirely tax-free at the federal level. But the exclusion requires a C corporation structure established before the investment, and the window to qualify closes long before most owners think about selling. Updated by the One Big Beautiful Bill Act in July 2025, the exclusion cap increased and the holding period shortened for newer issuances. This episode breaks down who qualifies, how stacking exclusions across trusts and family members can multiply the benefit, and what deliberate structure at formation means for the owners who get this right.
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    7 mins
  • Section 199A (QBI) Explained

    Section 199A (QBI) Explained
    May 20 2026
    This episode breaks down one of the most valuable and misunderstood provisions in the tax code: the Section 199A Qualified Business Income deduction. It covers the basic mechanics — up to 20% off qualifying pass-through income — then walks through the layered restrictions that apply above income thresholds, including the SSTB phase-out rules and the W-2 wage and qualified property limitation. Four concrete strategies high-income owners use to preserve eligibility are laid out: optimizing W-2 compensation in S-corps, investing in qualified depreciable property, using retirement plan contributions to pull income below phase-out thresholds, and restructuring entities to isolate non-SSTB revenue streams. The episode closes with an urgency note: Section 199A is currently scheduled to expire after 2025, making proactive planning especially time-sensitive.
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    10 mins
  • Retirement Plans as Tax Weapons

    Retirement Plans as Tax Weapons
    May 13 2026
    This episode reframes retirement plans as active tax management tools, not passive savings accounts. It walks through the plan hierarchy from Solo 401(k)s to cash balance plans, explaining how stacking the two can allow a business owner to defer $200,000 to $300,000 or more annually — reducing taxable income dollar-for-dollar at their top marginal rate. The tax math is covered in precise terms: at a 37% federal rate, a $300,000 contribution translates to $111,000 in immediate federal tax savings, with further compounding benefits from tax-deferred growth. The episode also addresses what makes these plans succeed or fail in practice — including actuarial requirements, multi-year funding commitments, and the income stability needed to sustain a defined benefit plan — illustrated through a case where a multi-partner firm sheltered over $1.2 million annually across its partnership.
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    10 mins
  • Income Timing & Expense Acceleration

    Income Timing & Expense Acceleration
    May 6 2026
    This episode breaks down how the tax code's time-based structure creates a powerful planning opportunity for business owners. Four core strategies are covered: deferring income into the next tax year using cash-basis accounting rules, accelerating deductions through the IRS 12-month prepaid expense rule, spreading capital gains across multiple years via installment sales under IRC Section 453, and timing year-end equipment purchases to capture Section 179 and bonus depreciation. A real-world case illustrates how a professional services firm reduced its tax bill by over $120,000 without changing a single dollar of its underlying economics — simply by shifting the timing of recognition. The episode closes with a key prerequisite: forward-looking tax modeling is required to use any of these strategies effectively, because the window closes on December 31.
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    9 mins
  • R&D Tax Credits for Non-Tech Businesses

    R&D Tax Credits for Non-Tech Businesses
    Apr 29 2026
    R&D tax credits under IRC Section 41 are widely misunderstood as a benefit reserved for Silicon Valley or pharmaceutical giants, but the legal standard is far broader. This episode breaks down the four-part test that determines eligibility — permitted purpose, technological principles, process of experimentation, and technical uncertainty — and shows how those criteria apply to everyday activities in construction, architecture, engineering, and manufacturing. Listeners learn which expenses qualify (wages, supplies, and contract research), how the credit is calculated, and a key provision that allows qualifying small businesses to offset payroll taxes directly rather than waiting on income tax liability. The episode closes with a clear action step: identify improvement projects from the last three years, document the technical uncertainty involved, and get a specialist review — because the work is often already done, and the credit simply requires the right documentation to claim it.
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    10 mins
  • Depreciation & Cost Segregation

    Depreciation & Cost Segregation
    Apr 22 2026
    This episode unpacks one of the most underutilized tools in the tax code: strategic depreciation. Host walks through how Section 179 and bonus depreciation work for equipment, how cost segregation studies reclassify commercial real estate components onto faster depreciation schedules (with real dollar examples), and how business owners who also hold real estate can qualify as real estate professionals to use paper losses against active income. The episode also covers look-back studies — a way to recover depreciation missed in prior years with no amended returns — and closes with a concrete action step to audit your own asset list.
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    10 mins