Reallocating from stock-heavy portfolio

Thanks to everyone for this very informative and helpful thread! Due to luck and smart relatives, my current portfolio is very tech stock-heavy; I’d like to transition a lot of these into index funds to reduce risk/volatility and make things easier to manage. I’m 37 years old. Current portfolio (total value is low 7 figures): * Stocks/Equities: 71.07% (90% US; 10% international) * Apple: 45.77% * Microsoft: 2.91% * Oracle: 4.69% * Equity ETFs (from robo-advisor account): 15.52% * Equity Mutual Funds: 2.18% * Bond ETFs (from robo-advisor account): 3.42% * Cash (almost all in money market funds or HYSA): 25.52% Here is the allocation across my current accounts: * Schwab – Robo-Advisor (taxable): 7.49% * Schwab – Trad Brokerage: 7.12% * Schwab – Roth IRA: 12.79% * Schwab – Trad IRA: 0.10% * Merrill Taxable Brokerage: 57.34% * Capital One (checking, HYSA): 15.17% I know my cash allocation is very high, so would like to invest a lot of it. To inform my next steps, I’d appreciate thoughts on the following: * How to best approach portfolio allocation/fund selection, given that the individual stocks I currently hold are already heavily represented in US market index funds * Tips or strategies for transitioning from current stocks to index funds, considering that almost the entire value of my stocks are unrealized LT gains. I’m expecting to have low income this year, so I could leverage that to sell some of these stocks. * For funds that may be used in next 5 years, any other suggested places to park these apart from money market funds and HYSA? * Thinking of moving my Merrill portfolio to Schwab or Fidelity. Any thoughts or pros/cons of either?