We help sophisticated investors, business owners, and the tax professionals who advise them deploy specialized, tax-advantaged investment strategies — coordinated across the full financial picture.
Business strategy affects taxes. Tax strategy affects investments. Investment decisions affect retirement and legacy. Yet most advisors work in isolation. Thornwood was built differently — aligning specialized strategies so each decision strengthens the whole plan.
Each strategy addresses a distinct planning challenge — from offsetting ordinary income to deferring capital gains on the sale of a highly appreciated asset.
Direct participation in domestic energy development, where intangible drilling costs can deliver a significant ordinary-income deduction in the year of investment.
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Defer capital gains on investment real estate by exchanging into institutional-grade, professionally managed Delaware Statutory Trust properties.
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Mid-sized businesses can formalize self-insurance through a captive — managing real risk while strategically deferring taxes on underwriting profits.
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Selling a business, property, or concentrated position? Defer capital gains and convert proceeds into a flexible installment income stream.
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Reinvest eligible capital gains into Qualified Opportunity Funds to defer, reduce, and — with a long enough hold — potentially eliminate future gains.
Explore strategyA short conversation helps us match the appropriate tax-advantaged structure to your goals, timeline, and risk profile.
Speak with an advisor*Figures reflect the operating history of Thornwood's strategic partners and program sponsors, not Thornwood Investments directly. Past performance is not indicative of future results.
Traditional financial advice happens in silos — but the most important decisions touch taxes, investments, and risk all at once. Thornwood brings those conversations together.
Each strategy is delivered through partners who focus exclusively on their discipline — energy, real estate, captives, or trusts — not generalists dabbling across the board.
We align tax, investment, and risk planning so a single decision — selling a property, exiting a business — is optimized across every dimension at once.
Sophisticated strategies demand rigor. Every structure is grounded in the relevant tax code, documented properly, and supported by professional administration.
Entrepreneurs planning to grow, protect, and eventually transition their companies — and to manage the tax impact of a sale or exit.
Accountants and preparers who want access to expanded planning tools and a collaborative partner to serve their highest-value clients.
Investors with appreciated assets, concentrated positions, or large realized gains seeking a coordinated, tax-aware strategy.
Whether you're facing a large gain, exploring ordinary-income offsets, or advising clients who deserve more — a short conversation is the right first step.
