Key Questions


Managing your wealth goes beyond tactics and strategies. Tactics and strategies are table stakes (i.e. it’s a given!). True wealth is about understanding the impacts on your family, your career, and ultimately, your values. Our experience has been that the most successful outcomes are when you integrate your values, your family, and your career in your decisions.


Get smart with your stock! The decision to sell your stock, or keep your stock, often revolves around the tax impact of an exercise or sale.  Though the tax impact is important, our viewpoint is that the tax should not drive the decision to exercise or sell.  In fact, we believe in an alternative decision-making process:

  • What is the measured risk of the current stock holding? Even if the stock has some upside, what could you be giving up (e.g. fulfilling another, more immediate short-term goal) by holding onto the stock? The performance return of the stock is important, but understanding at what expense (i.e. the risk) is just as, if not more, important in evaluating the stock.
  • What alternatives do you have with the stock? By selling your stock, can you achieve a financial goal? If you hold onto the stock, are there ways to protect the stock (e.g. margin, hedging, etc.)? Understanding the pros and cons of the various alternatives is important.
  • Oftentimes, it won’t be just one strategy, but a combination of various strategies. Only until understanding the measured risk and the alternatives, then can you definitively evaluate the tax impact of a decision, and create a plan on how to mitigate any projected taxes.


Just because you can, doesn’t mean you should! The simplest tax management techniques are usually the best, and should be pursued first.  We cannot overstate this enough.  We often come across highly complex (e.g. lots of moving parts with extra costs associated with them), or highly risky (e.g. high audit risk) strategies or “tactics” (often marketed as a “tax loophole” or “tax haven”) in an effort to save on taxes.  

There are lots of different kinds of taxes that require different approaches, whether it’s how to deal with capital gains taxes, ordinary income taxes (from salary, and wage compensation), estate taxes, or even esoteric rules specific to company stock (e.g. 83(b) election, QSBS rollovers, etc.).  With proper planning, some of these taxes can be optional.
Remember that the simplest tax management techniques are usually the best, and should be pursued first.  They are fastest, cheapest, have the least regulatory constraint, and often, the least audit exposure.  


Accelerate your timeline! Even more important than the question of “Do I have enough?” is “When is enough, for you?” Rather than a tax tactic or investment strategy, the real discussion is likely more of a philosophical one, centered around your values and what is truly most important to you.

  • “Can I take a sabbatical, or ‘retire early’?” 
  • “Can I now pursue my second dream career?” 
  • “Can I spend more time with my family?”
  • “Can I leave a legacy to the charities and causes that are dear to my heart?”
Engaging in an intentional process can help clarify your true values, and define what is truly important to you, and what kind of lasting legacy you would like to provide to your family, your children, and your community. Our work typically goes beyond the tactics and strategies of sophisticated investment management or financial planning, but rather life and career planning. 


Take our Assessment at no-cost to determine how to best manage your company stock, reduce your taxes, or determine if you have enough.

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