Risk Runners Presents

Tax Playbook

US Tax Code strategies — taught not in accounting offices but through audits, heists, courtrooms, and kitchen-table conversations.

Internal Revenue Code • 12 Strategies • Real Savings
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The tax code is 6,000 pages. About 1,000 are ways to reduce your tax.

Most people only see the pages that compute their bill. Tax Playbook teaches the other pages — the ones Congress wrote specifically to incentivize saving, investing, building businesses, and giving to charity. Each screenplay drops a real IRC section into a dramatic scenario: an IRS audit, a CPA heist-planning session, or a Tax Court true crime.

The strategies are real. The math is real. The characters just make it memorable.

Twelve strategies. Twelve stories. All legal.

The Twelve Strategies

Click any card to read the full 10-page screenplay.

IRC Section 1031
The Real Estate Shuffle
A slick CPA explains how to defer capital gains taxes indefinitely by swapping investment properties — turning one duplex into a portfolio without ever writing the IRS a check.
10 PAGES Read →
IRC Section 170
The Philanthropist's Vault
A financial advisor reveals how to donate appreciated stock to a DAF — getting a full deduction at market value while avoiding capital gains, then granting to charities over decades on your own timeline.
10 PAGES Read →
IRC Section 408A
The Income Ceiling Bypass
A savvy financial planner shows a high-earning couple how to contribute to a Roth IRA despite being over the income limit — using a perfectly legal two-step conversion that Congress has known about for decades.
10 PAGES Read →
IRC Sections 1361–1379
The Self-Employment Tax Escape
A freelancer making $200K learns how electing S-Corp status splits her income into salary and distributions — saving $15,000+ per year in self-employment taxes while staying perfectly legal.
10 PAGES Read →
IRC Section 199A
The Pass-Through Bonus
A tax strategist explains how pass-through business owners get a free 20% deduction on qualified business income — effectively reducing their top rate from 37% to 29.6% — and the tricks to stay under the income thresholds.
10 PAGES Read →
IRC Section 1091
The Portfolio Prune
A wealth manager teaches a panicking client how to turn market losses into tax savings by strategically selling, booking the loss, and immediately buying a similar (but not identical) investment — all while navigating the wash sale rule.
10 PAGES Read →
IRC Section 168 (MACRS)
The Building Breakdown
A real estate investor learns how a cost segregation study reclassifies parts of a building into faster depreciation categories — turning a 27.5-year deduction into massive Year 1 write-offs through bonus depreciation.
10 PAGES Read →
IRC Section 223
The Triple Tax-Free Account
A benefits coordinator reveals the HSA as the only account in the tax code with triple tax advantages — tax-deductible contributions, tax-free growth, AND tax-free withdrawals — making it more powerful than a Roth IRA for healthcare expenses.
10 PAGES Read →
IRC Section 1400Z-2
The Capital Gains Vanishing Act
An investor with a massive capital gain discovers how Qualified Opportunity Zones let her defer the gain, and potentially eliminate taxes on ALL future appreciation — by investing in designated economically distressed communities.
10 PAGES Read →
IRC Section 280A(g)
The Home Rental Loophole
A business owner discovers she can rent her own home to her own business for meetings — tax-free income to her, deductible expense to the business — using a provision originally written for homeowners near the Masters Tournament.
10 PAGES Read →
IRC Section 664
The Annuity Factory
A couple with a $3M concentrated stock position learns how a CRT lets them diversify without paying capital gains, receive a lifetime income stream, get an immediate charitable deduction, and benefit their favorite nonprofit at death.
10 PAGES Read →
IRC Section 179
The Equipment Write-Off
A small business owner facing a monster tax bill discovers she can deduct the FULL cost of business equipment and vehicles in Year One — including the infamous 'G-Wagon loophole' — turning a tax liability into a capital investment.
10 PAGES Read →