For investors implementing a Deferred Sales Trust (DST), the sale of appreciated assets and deferral of capital gains tax represents just the beginning of the journey. The critical next step—how trust assets are invested—will ultimately determine whether your DST generates sustainable income throughout your retirement. Establishing a comprehensive Investment Policy Statement (IPS) provides the essential […]

When establishing a Deferred Sales Trust (DST), one of the most consequential decisions you’ll face involves determining how much flexibility versus restriction to build into your trust structure. This fundamental choice affects everything from investment options and payment adjustability to potential IRS scrutiny and long-term security. Understanding the spectrum of DST structures—from highly restricted to […]

For investors considering a Deferred Sales Trust (DST) as part of their retirement strategy, understanding the precise mechanics of implementation is crucial. While the concept may seem straightforward—selling an appreciated asset to a trust in exchange for future payments—the actual execution involves a carefully orchestrated sequence of legal, financial, and administrative steps. This comprehensive guide […]

Most investors familiar with Deferred Sales Trusts (DSTs) recognize their power for deferring capital gains tax when selling appreciated assets. However, sophisticated retirement planners understand that DSTs offer solutions to numerous other tax challenges that retirees commonly face. From reducing Net Investment Income Tax exposure to mitigating Required Minimum Distribution impacts, these additional tax advantages […]

Choosing the right trustee for your Deferred Sales Trust (DST) might be the most critical decision in your retirement income planning process. This professional will manage millions of dollars of your hard-earned wealth, ensure tax compliance, and ultimately determine whether your retirement income flows as planned for decades to come. Yet many investors spend more […]

When planning for retirement income while managing significant appreciated assets, sophisticated investors often consider trust structures that offer tax advantages. Two powerful options—Deferred Sales Trusts (DSTs) and Charitable Remainder Trusts (CRTs)—provide compelling benefits, yet serve different financial objectives. Understanding the key differences and similarities between these vehicles is crucial for optimizing your retirement income strategy. […]

For retirees selling appreciated assets, the tax implications can dramatically impact long-term financial security. A Deferred Sales Trust (DST) offers a powerful tax deferral strategy, but understanding exactly how payments are taxed throughout retirement is crucial for effective planning. This comprehensive guide provides a year-by-year breakdown of DST tax treatment, allowing you to visualize precisely […]

After dedicating years—often decades—to building a successful business, many entrepreneurs face a critical challenge: how to convert the substantial equity trapped in their company into reliable, sustainable income for retirement. This transition represents one of the most significant financial events in a business owner’s life, with far-reaching implications for their future security and lifestyle. Converting […]

Market volatility has become the new normal for investors. From pandemic disruptions to inflation concerns and geopolitical tensions, recent years have demonstrated how quickly investment landscapes can shift. For retirees and those approaching retirement, these fluctuations present a serious challenge: How do you create reliable income when traditional investment vehicles seem increasingly unpredictable? This is […]