Category: Equity & Tax
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Long-Short Direct Indexing: A Sophisticated Path Out of a Concentrated Tech Position
If you have spent years at a successful technology company, there is a good chance that a large share of your net worth now sits in a single stock. Over the past few years, a powerful approach has moved from institutional trading desks into the wealth management mainstream: tax-aware long-short investing, also called long-short direct…
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Borrowing From the Market: Box Spreads for Mortgages, Margin, and Concentrated Stock
Used correctly, a box spread lets you borrow at a fixed rate set not by a bank but by the options market, a rate that typically sits close to the risk-free rate and well below what a mortgage or a margin desk would charge.
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The Luxury Airbnb Write-Off: How High Earners Offset Their Salary With a Short-Term Rental
Buy the right luxury property, rent it out on Airbnb or a similar platform, and under a specific and well-established set of rules, the paper losses it generates in the first year can offset your salary, your practice income, or your business income directly.
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How to Actually Write Off a Private Jet (Legally)
If you own a successful business and your income has reached a certain level, you have probably heard some version of this pitch: buy a private jet, deduct the entire purchase price against your income, and let the tax savings pay for a meaningful share of the aircraft. In 2025 the law changed in a…
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The Tax Mistakes Aesthetic Practitioners Make When Their Income Takes Off
Aesthetics is one of the few corners of healthcare where a clinician’s income can climb faster than almost anyone predicted. The result is a predictable set of expensive mistakes. Here are the ones we see most often, and what to do about them.
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The High-Earner’s Roth Problem: Backdoor and Mega-Backdoor Strategies for Physicians
Roth accounts are among the most valuable tools in a long-term financial plan. Money grows tax-free, qualified withdrawals are tax-free, and unlike traditional retirement accounts, Roth IRAs are not subject to required minimum distributions during the owner’s lifetime. For a physician who expects to be in a high tax bracket for decades and well into…
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SpaceX (SPCX) Shareholders: Tax & Wealth Strategies for the Post-IPO Window
From the staggered lock-up tranches in SpaceX’s S-1 to exchange funds, loss harvesting, CRTs, and GRATs – a practical field guide for concentrated SPCX holders.
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The Loan-Out Decision: When Actors, Writers, and Directors Should Incorporate
In entertainment, a quiet piece of tax structure can make a meaningful difference in what a working professional keeps. It is the loan-out company, an entity through which actors, writers, directors, and other creatives provide their services. Instead of being hired directly by a studio, network, or production, the talent is employed by their own…
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W-2, 1099, or S-Corp? Tax-Efficient Structuring for Locum and Moonlighting Income
Modern medical and dental careers are rarely a single W-2 job for life. Many physicians and dentists earn income from several sources at once: an employed position, locum tenens assignments, moonlighting shifts, telehealth work, consulting, expert witness fees, or a side practice. Each of those income streams can be structured in different ways, and the…
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Maxing the After-Tax 401(k): The Mega-Backdoor Roth at Big Tech
Many technology employees diligently max out their 401(k) each year and assume they have done all the tax-advantaged saving available to them. For employees at companies with the right plan features, that assumption leaves one of the most valuable opportunities in the entire tax code untouched. It is called the mega-backdoor Roth, and at large…