Who we serve
Executives and many long-tenured employees commonly accumulate large single-stock positions through years of equity grants, discounted purchase plans, and acquisitions that convert one holding into a larger one. The position is usually held at a low cost basis, which makes selling expensive and postponement tempting. Meanwhile the same company pays your salary, so the exposure is doubled.
What this complicates
People compare the tax bill of selling against zero. The real comparison is against the risk of holding — and single stocks have historically had a meaningfully wider range of long-term outcomes than a diversified portfolio, including permanent loss.
A bad year for the company can mean a smaller bonus, a layoff, and a portfolio drawdown arriving together. Diversifying is partly about not having your worst year happen all at once.
Why us
We work with executives of tech and defense employers across Colorado Springs, where this situation comes up often.
If you are nearby, you can come in and sit down with us. If you are not, we meet by phone or video call. Either way, when something changes, you reach someone who knows you.
Questions
There is rarely a fast way that is also a good way. Staging sales across tax years, using long-term rates, harvesting offsetting losses, and selling into low-income years usually costs far less than one large sale. Sometimes charitable strategies can help with the most appreciated lots.
Usually no. The purchase discount is valuable, and turning it down to avoid concentration gives up a known benefit to avoid an uncertain risk. The fix is to have a comprehensive long-term financial plan.
It all depends on your unique financial situation. Often right at vest, because the shares are taxed as income at that point anyway — holding them afterward is a fresh decision to buy that stock at that price, and most people would not make that decision deliberately.
If you give to charity anyway, donating appreciated shares rather than cash is usually more tax efficient — you avoid the gain and may deduct the value. A donor-advised fund lets you take the deduction in a high-income year and give it out over time.
Related
This is the window where the decisions are still reversible and the numbers are finally real.
A pension you elect once. Accounts inherited through decades of mergers. A savings plan with room most employers do not offer. All of it worth more if you know what you are actually holding.
One year, one large number, and the rest of your life to fund from it. The planning window around the sale is short and usually valuable.
Thirty minutes to see where your income will come from. If we are not the right fit, we will tell you.
