Should I Sell a Stock with a Large Taxable Gain? (Part 3)

Have you acquired stock over time and seen it significantly rise in value over time? What should you do? Let it ride? Or should you sell, pay taxes, and reinvest in a more diversified fashion? Let’s consider some transition strategies to mitigate the tax bit to become more diversified. Continue reading

Should I Sell a Stock with a Large Taxable Gain? (Part 2)

Have you acquired stock over time and seen it significantly rise in value over time? Now you have large, embedded capital gains and a more concentrated portfolio. Should you sell, pay taxes, and reinvest in a more diversified portfolio, or let it ride? Continue reading

How Early Retirees Can Get A BIG Health Insurance Tax Credit

Many early retirees find they must utilize Affordable Care Act (ACA or Obamacare) policies to bridge the gap from employer-provided health insurance to Medicare at age 65. ACA policies are expensive but even affluent families may be able to obtain … Continue reading

Ep 85: What’s a “Conservative” Investor To Do These Days?

Having reasonable assumptions for investment returns is critically important for many reasons. These assumptions will impact your retirement plan, investment allocation, and your peace of mind. Hear Kevin review discuss a recent letter written to his clients about the three broad categories of investments. Continue reading

Should I Sell a Stock with a Large Taxable Gain? (Part 1)

Have you acquired stock over time and seen it significantly rise in value over time? Perhaps you simply bought and held, were gifted shares, or accumulated company stock through grants or options. Now you have a more concentrated portfolio. What should you do? Let it ride? Or should you sell, pay taxes, and reinvest? Continue reading