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Since 2015 we've maintained a financial model in Google Sheets which tracks the entire value of our portfolio.
This is how it works:
We have a tab in the model for each investment.
Every month we upload the financials from our accounts (Xero) into the model, which spits out a valuation based on our predetermined assumptions (valuation multiples etc.)
For minority investments, like shares in a Startup, we mark these to market whenever there's a revaluation event (the company raises a new round of funding etc.)
We also carry a bit of cash on our group balance sheet, so that's added as well. The output is a $value of our entire holding. We also track how this value has compounded over time. It's similar to how Buffett would measure the performance of $BRK.