<prompt> Human: Throwaway as I dont want all my friends to know my financial situation.My situation: 28 years old making 82k base salary, plus anywhere from 0-22k annual bonus has varied quite a bit but never less than 5k plus about 40k in RSUs restricted stock units per year which vest over 4 years. I have zero debt apart from my mortgage owe 240k on a house worth 350k. Roth IRA worth about 12k, 401k worth about 50k annual contributions around 11k. Emergency fund is dialed in to support me for 9 months if anything were to happen to my employment.The majority of my net worth is tied up in company stock publicly traded company. In addition to the annual stock grants I also have 3 of my income going to employee stock purchase I buy at a 15-25 discount - have to hold it for a minimum of 6 months. So all said and done I have about 160k worth of company stock that is either vested able to sell or I own outright from stock purchase plan - this is mine whether or not I leave the company. Plus I cash flow an additional 40-50k per year as my RSUs vest total unvested shares worth about 200k vesting gradually over the next 4 years. Obviously this is a very large percentage of my net worth tied up in one place.I feel like everyone is going to tell me to sell a large portion of my shares and invest in more diversified assets but hear me out:a Selling a lot of these will result in significant capital gains taxesb Company is stable and our stock price performance has been incredible since I started 4 years ago. I started buyingacquiring shares at 30share and now were trading at 225. Based on fundamentals we are still slightly undervalued compared to other companies in our industry. Also as a company insider I feel like I have a better overall understanding of the company and our business than the average investor.c Im young and have a high risk tolerance. I have no need for this money right now so why not let it ride?Thoughts? Am I nuts?  <response>: Doesnt matter about the taxes. Sell, diversify, and reduce your risk.Get as much stock as you can at a discount, but sell it as soon as you can. 