<prompt> Human: My elderly, retired father has a 30-year-old Vanguard retirement fund not IRA made up of many highly diversified mutual funds. It is currently valued at approx. USD 800,000. He was just a lowly blue-collar American worker who was smart about setting aside a portion of his monthly income for over 3 decades.He was originally planning on letting me inherit the fund after his death which might not be for a long time; he is now in his 70s but very healthy. However, now he is considering withdrawing about half 400K to start up a post-retirement small business. I think its a great idea for him, but he is petrified about the tax issue, and wont do it if he has to pay too much in taxes.What are all his options to pay the least amount of taxes?  <response>: However, now he is considering withdrawing about half 400K to start up a post-retirement small business. I think its a great idea for him, but he is petrified about the tax issue, and wont do it if he has to pay too much in taxes.I am not going to get into whether this makes sense or not the small business so lets ignore it for now. What are all his options to pay the least amount of taxes?1. You should seek professional tax advice from a CPA and not strangers on the internet. Especially with the potential tax implications involved based on capital gains for 30 years. I dont know the basis, I dont know the gains, I dont know where you dad lives state taxes, if any and I dont know his current tax bracketinfo.2. Consider borrowing against the account so you dont have to sell off a position. If you choose to talk to a CPA, I would discuss this option. -To the posters in the thread, OP isnt asking for advice on the small business and whether OPs dad should do it. Obviously there is risk involved with the small business especially for someone that age. In addition, does anyone know what the small business is and what is the actual risk involved. Certanly not based on the OP.-OP is asking for tax advice. The real answer should be to seek tax advice from a professional. 