“Strategic advice” is a very open-ended term, but when we use it, we have a specific meaning in mind. We think of our role in relatively simple terms: Our job is to listen to each of our clients, understand the unique nature of their challenges and aspirations, and then deliver effective and creative solutions that help them achieve their goals. The listening component of our work is very important; we can only do good work for clients if we truly devote ourselves to understanding their subjective perspective as well as their objective circumstances. In many cases, the solution we deliver to a client may be a straightforward answer to a clear request. For example, if an institution asks us for a well-managed small-cap equity strategy with a documented track record, we can provide that. But in other cases, our clients face complex challenges for which there are no universally applicable solutions. It is here where the concept of strategic advice becomes truly essential, so we can help clients with complicated scenarios to develop strategies tailored specifically to their situation. This publication highlights a particular situation when this sort of approach can add value. Many of our clients have a large proportion of their wealth concentrated in a single asset—perhaps in a large block of a publicly traded company, a sizable interest in a private business or some other asset. Often these have been successful investments over time—hence, they have grown in value far beyond their cost basis. At some point, many of these clients face a similar dilemma: Holding that asset may create meaningful risk, but selling it would create a meaningful tax event. While these situations may appear similar on the surface, each client’s circumstances and perspectives are distinct. Their situations involve variations in the attributes of the asset being examined, the client’s tax scenario, family dynamics, emotional attachment to the asset in question and many other factors. Our goal with each client is to address their challenges holistically—from a strategic advisory perspective. We seek to draw on diverse expertise from around the firm and choose the approach that best addresses the risks and opportunities that are most important to each specific client. Oftentimes, this means executing on a range of ideas. A client may wish to retain some exposure to a holding as part of a family wealth transfer plan (perhaps using Grantor Retained Annuity Trusts [GRAT] or other trust mechanisms), while also reducing risk (by selling, hedging or gifting to charity) as well as mitigating taxes through various means. A comprehensive strategy using multiple techniques can help to accomplish a variety of goals at once. This publication seeks to summarize the nature of the challenges presented by these scenarios and offer a snapshot of the various solutions we use to deliver results to clients. Along the way, we also hope we can offer a window into how this concept of strategic advice serves as the foundation of our client relationships. Any accounting, business or tax advice contained in this communication, including attachments and enclosures, is not intended as a thorough, in-depth analysis of specific issues, nor a substitute for a formal opinion, nor is it sufficient to avoid tax-related penalties. The views expressed are those of the author and Brown Advisory as of the date referenced and are subject to change at any time based on market or other conditions. These views are not intended to be and should not be relied upon as investment advice and are not intended to be a forecast of future events or a guarantee of future results. Past performance is not a guarantee of future performance and you may not get back the amount invested. The information provided in this material is not intended to be and should not be considered to be a recommendation or suggestion to engage in or refrain from a particular course of action or to make or hold a particular investment or pursue a particular investment strategy, including whether or not to buy, sell, or hold any of the securities mentioned. It should not be assumed that investments in such securities have been or will be profitable. To the extent specific securities are mentioned, they have been selected by the author on an objective basis to illustrate views expressed in the commentary and do not represent all of the securities purchased, sold or recommended for advisory clients. The information contained herein has been prepared from sources believed reliable but is not guaranteed by us as to its timeliness or accuracy, and is not a complete summary or statement of all available data. This piece is intended solely for our clients and prospective clients, is for informational purposes only, and is not individually tailored for or directed to any particular client or prospective client.