エピソード

  • 18 – International Tax Planning: Myths vs. Reality

    18 – International Tax Planning: Myths vs. Reality
    2026/07/15
    Offshore does not mean illegal — but ignorance can produce catastrophic penalties. Professor Jack Ledger demystifies the three pillars of U.S. international tax compliance: FBAR reporting, Controlled Foreign Corporation rules including Subpart F and GILTI, and FATCA's global information exchange network. He then explains what legitimate international planning actually looks like — treaty optimization, residency planning, and compliant jurisdictional structuring — and what the IRS's Streamlined Disclosure program offers for those who need to come current.
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    11 分
  • 17 – Strategic Debt for Tax Efficiency

    17 – Strategic Debt for Tax Efficiency
    2026/07/08
    Debt is not a liability — it is a strategic instrument for accessing capital without triggering taxes. Professor Jack Ledger explains how sophisticated families borrow against portfolios, real estate, and businesses to fund acquisitions, lifestyle, and growth without selling appreciated assets and recognizing taxable gains. This episode covers investment interest deductibility, the Section 163(j) business interest limitation, and the risk management disciplines that make leverage a tool rather than a threat.
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    10 分
  • Tax-Efficient Investing

    Tax-Efficient Investing
    2026/06/24
    Tax-efficient investing is not about picking better securities — it's about engineering a portfolio so that each asset class sits in its most tax-favorable account, losses are harvested continuously throughout the year rather than as a year-end afterthought, and fund selection minimizes the tax drag created by high-turnover strategies. Asset location alone can add approximately 0.48% in expected annual return; systematic tax-loss harvesting generates additional savings that compound significantly over decades. This episode covers all three foundational disciplines — asset location, tax-loss harvesting, and low-turnover fund selection — and explains how sophisticated families integrate these practices with their entity structures, trust planning, and liquidity events into a unified portfolio architecture reviewed annually.
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    8 分
  • Tax-Efficient Investing: Part 2

    Tax-Efficient Investing: Part 2
    2026/06/24
    Investment returns are not what you earn — they are what you keep after taxes. In this episode, Professor Jack Ledger breaks down the three pillars of tax-efficient portfolio management: asset location, the rate differential between short- and long-term capital gains, and disciplined tax-loss harvesting. From placing income-producing assets inside retirement accounts to leveraging bonus depreciation through private investments, this episode provides the framework for engineering after-tax returns rather than simply chasing gross performance.
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    10 分
  • Tax Planning for Business Exits

    Tax Planning for Business Exits
    2026/06/17
    Business exits without advance planning routinely result in federal and state capital gains taxes, depreciation recapture, and estate taxes consuming 30–50% of sale proceeds. The four primary tools that change that outcome — ESOPs with Section 1042 deferral, installment sales, trust and family planning, and charitable remainder trusts — each require years of structural lead time to implement. With 79% of business owners planning to exit within a decade but fewer than 20% holding a written exit plan, this episode is designed to close that gap before the window closes. The owners who protect the most wealth model their scenarios long before a transaction appears on the horizon — and build their structures while they still have time to execute.
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    8 分
  • Captive Insurance Companies

    Captive Insurance Companies
    2026/06/10
    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 分
  • Opportunity Zones & Capital Gains Deferral

    Opportunity Zones & Capital Gains Deferral
    2026/06/03
    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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    8 分
  • Qualified Small Business Stock (QSBS)

    Qualified Small Business Stock (QSBS)
    2026/05/27
    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 分