Case Studies
Featured Product
Tailwind Fund
User Profile
Tech Executive (Illustrative)
Published
The Concentrated Tech Position.
An illustrative profile. How a tech executive could turn 15 years of stock comp into tax-deferred yield with an aviation upside.
$800K
Modeled Investment
6%
Target Yield
12%
Aviation Redemption
Deferred
Tax on Entry & Exit
Case Study
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The Concentrated Tech Position.
The Concentrated Tech Position.
"I've invested years of my career into the companies in this portfolio. It was emotional to think about selling out of those positions, and once the tax picture came into view I was more comfortable just keeping the concentration."
Maya Chen
Partner at a Legendary VC Firm
After a decade at Meta and five years at Google, Maya (an illustrative profile) has built significant wealth almost entirely through equity compensation and reinvestment. Her RSUs have compounded across two of the most consequential technology runs of the last generation. She has meaningful liquidity, more shares continuing to vest, and a portfolio heavily concentrated in two names in the same sector. She is not looking to take more risk. She is looking to take less, while finally generating income from assets that have only ever grown.
Challenge
Maya's financial picture is one that wealth advisors increasingly encounter: a high-earning executive with a net worth built almost entirely in tech. The portfolio is concentrated, the income is variable, and the predictable yield is effectively zero. Every year, more shares vest. Every year, the concentration deepens. She has thought about diversifying for years but selling means recognizing a gain that has compounded for over a decade, a tax event that has kept her anchored to positions she would otherwise have moved.
She also has a milestone coming. A milestone trip on her 40th birthday, something more than commercial, had been on the list for years. But she has never flown private and has no interest in committing to a fractional program or paying charter rates for a one-time experience. She wanted a path that made financial sense, not just a splurge.
Solution
Maya's advisor introduced her to Craft's Tailwind Fund, a yield-focused vehicle that uses the same tax-deferred exchange-fund mechanism as the Glidepath Fund but is structured specifically for investors seeking predictable, tax-deferred income. The principal remains fully invested throughout. What the fund distributes is a quarterly yield coupon, and how that coupon is treated is where the Tailwind structure becomes uniquely flexible.
Tailwind investors make a choice each quarter. By default, the 6% targeted coupon is reinvested into the fund and remains tax-deferred; principal compounds and the gain clock stays paused. Alternatively, the investor can elect to take the coupon as cash, in which case it is treated as taxable income, or redirect it toward Craft aviation access at 12%, effectively doubling the coupon's purchasing power when applied to flight. Principal is never touched.
Tax-deferred diversification out of concentrated tech equity
Maya contributes $800K of appreciated Meta and Google stock directly into the Tailwind Fund using Craft's tax-deferred exchange-fund mechanism. No sale. No capital gains recognized at entry. The concentrated positions are exchanged into a diversified fund, her principal stays fully invested, and the gain clock pauses.
6% targeted coupon, reinvested and tax-deferred by default
Each quarter, the targeted 6% coupon is reinvested into the fund. While reinvested, the coupon remains tax-deferred and continues to compound alongside principal. Taken as cash, the same coupon would be treated as taxable income at distribution, so by leaving it in the fund Maya keeps both the principal and the coupon working tax-efficiently.
One quarter, redirected to aviation at 2× the value
For her 40th birthday, Maya elects, for one quarter, to redirect her coupon to Craft aviation access. The 6% coupon converts to 12% in flight credit, doubling its purchasing power. Principal is never touched. The remaining quarters continue to reinvest tax-deferred as usual.
Impact
Maya diversifies out of more than a decade of concentrated tech equity without triggering a taxable event. Her $800K principal remains fully invested and growing. Her quarterly coupon, targeted at 6%, reinvests on a tax-deferred basis by default, delivering compounding she never had from her equity portfolio. And in the one quarter she elects to fly, the same coupon goes twice as far applied to aviation as it would have taken as cash. Each new vesting event becomes a potential Tailwind contribution rather than a deepening concentration problem.
Portfolio Impact
Metric | Prior Portfolio | With Craft |
|---|---|---|
Capital in concentrated tech equity | $800K, 2 names, no yield | $800K, diversified, fully invested |
Yield treatment (default) | None | Reinvested, tax-deferred at 6% target |
Tax event to reallocate | Full capital gains recognized | Deferred via exchange fund |
Optional aviation redemption | Not available | 12% in-kind, one quarter elected |
Net portfolio position | Growth only, no income, no diversification | Tax-deferred compounding + aviation option |
Illustrative. Maya Chen is a composite profile created for the purpose of explaining Tailwind Fund mechanics. The Tailwind Fund is launching Q3 2026. No client has yet entered the fund or realized the outcomes depicted. Target yield (6%) and aviation redemption multiple (12%) reflect the fund's published structure as of March 2026 and are not guarantees.
Tax treatment. Coupons reinvested into the fund are tax-deferred while principal remains in the fund. Coupons taken as cash are treated as taxable income at the investor's applicable rate. Aviation-redemption coupons are governed by the fund's published in-kind distribution mechanics. Investors should consult their tax advisor for treatment specific to their situation.