119 - What Should I Do When I Have Large Unrealized Gains in a Concentrated Stock Holding?

Scott and James discuss what you should do when you have large unrealized gains in a concentrated stock holding. Listener Question 1. My wife and I have been blessed with good fortune through our ESPP and RSU programs across 4 different employers. Having always been a buy-and-hold investor, these companies now have significant unrealized capital gains and represent almost 50% of portfolio value and a strong dividend cash flow that could provide income during a job loss. We live in CA and are in top tax brackets and would like to effectively diversify without loosing over 50% to taxes. 2. I currently have around 4,500 shares of AAPL. This makes up about 54% of my total stocks. I have 2,200 shares in my investment (non-retirement) account which makes up 100% of this total. I want to reallocate some of the AAPL, but it will have serious tax implications especially with my investment account. What do you recommend? Planning Points Discussed Retirement Planning Utilizing Time Efficiently Capital Appreciation Purchasing Power Other issues (IRAs, Inflation, Financial Goals, etc.) Timestamps: 1:30 - Introduction 3:27 - First Listener Question  5:05 - Individual Stock Example 6:58 - Investing v. Gambling 9:05- Taxes 9:43 - Cost Basis 12:15 - Stock Option Tax Planning 14:22 - Peace of Mind & Tax Strategy 17:55 - Lowest Cost Basis v. Highest Cost Basis 19:00 - Charitable Giving Strategy 21:55 - Second Listener Question 23:00 - Retirement Account Tax Benefits  24:53 - Aligning Your Financial Goals   LET'S CONNECT! James Facebook LinkedIn Website Scott Facebook Twitter Website ENJOY THE SHOW? Don’t miss an episode, subscribe via iTunes, Stitcher, Spotify, or Google Play. Leave us a review on iTunes. Have a money question you want us to answer? Submit one her