[stinkypantsman]

This entrepreneur may find that they are not in control of what happens. If they raise at a $100M valuation they are likely trading board seats to the preferred investors. If the preferred investors provide liquidity to the founder ("de-risking it") then they are aiming to align everyone (founder & investors) to aim for the $1B+ IPO outcome, not the PE-exit that the entrepreneur is wishing for. And if they are selling board seats in this round the founder may not be able to get authorization to sell.

Once you take VC money and ESPECIALLY if you sell board seats and sell your own options you are agreeing to go big.