When Should You Start Tax Planning?
Tax strategy works when designed before income is earned. Sam Prentice's rule: plan in Q1 for the following year. Q4 is late but still captures most of the value.
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Sam's Insights
Thoughts on wealth, happiness, and living a life of purpose.
Creative Tax Strategies Beyond Buying an Airbnb
Three legally distinct categories of tax reduction exist, and rental real estate is one tool in one of them. Sam Prentice explains entity restructuring, oil and gas IDCs, and tax credits.
Read article →What Does a Wealth Architect Actually Do?
What a wealth architect does across taxes, entities, and asset protection, and how the role differs from a financial advisor or CPA.
Read article →How to Choose a Tax Strategist
What separates a tax strategist from a return preparer, which credentials matter, and the questions to ask before hiring one.
Read article →How to Set Up a Holding Company to Protect IP From Lawsuits
Separating intellectual property from operating risk: the holding structure, the license-back, arm's-length royalties under Section 482, and where the attorney takes over.
Read article →How to Offset W-2 Income After the 461(l) Loss Limit
Hit the excess business loss cap? What happens to the disallowed loss, how the NOL carryover and the 80 percent limit work, and the timing moves that keep large losses useful.
Read article →How Founders Can Reduce Taxes When Selling a Company
Exit tax planning for founders: the QSBS exclusion and its 2025 changes, the Section 1045 rollover, installment sales, and why the clock starts years before the letter of intent.
Read article →How to Reduce Capital Gains Taxes
The legal tools that lower a capital gains bill: holding periods and the 0/15/20 brackets, tax-loss harvesting, 1031 exchanges, QSBS, installment sales, opportunity funds, and charitable trusts.
Read article →How to Offset W-2 Income With Business Losses
The legal ways high earners offset wages with business losses: short-term rentals, real estate professional status, cost segregation, oil and gas, and the Section 461(l) cap.
Read article →The Enlightenment Portfolio: Where Investing Meets Spirituality and Silicon Valley
I've been watching something strange happen at the intersection of three worlds that aren't supposed to touch. Investing. Spirituality. Technology.
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