Share your insights or perspective on the financial matter presented in the input.

When does it make sense for the money paid for equity to go to the corporation?
If the check is written as a check to BigCo, it is less clear how Jack can compensate himself for the equity sale. It is as if the equity was owned by the corporation, not by Jack. This is correct.  If the check is written to BigCo, then it is BigCo issuing new shares.  Jack doesn't compensate himself for the equity sale, as he didn't sell anything.  The company traded shares for money which it uses for expansion.  In the long term, the capital gain from expansion may exceed the value of a $200,000 no-interest loan to the company.   If the value of the company before investing $250,000 is $1 million, then the value after investing is $1.25 million.  So $250,000 is 20% of the value of the company.  BigCo should not give the buyer 25% of BigCo but only 20% in that example.  If it does give 25%, the buyer is getting a $312,500 stake for only $250,000.   With the other example, Jack sells 25% of the company for $250,000 from his personal shares.  This doesn't change the assessed value of the company, just Jack's stake.  Jack then loans the company $200,000.  This also doesn't change the assessed value of the company (at least in theory).  It gains $200,000 but has an offsetting debt of $200,000.  In net, that's no change.  Assets and liabilities balance the same.   So if you know that the assessed value of the company is $1 million and that the buyer is paying $250,000 for a 25% stake at that same valuation, then you know that the check is being written to Jack.  If the check is written to BigCo, then one or more of those numbers is incorrect.   The buyer could be getting a 20% stake.  The new value of the company after the investment is $1.25 million.   Or paying $333,333.33.  The new value of the company after the investment is $1,333,333.33.   Or BigCo could only be worth $750,000 before the investment.  The new value of the company after the investment is $1 million.   Or Jack is getting screwed, selling $312,500 in stock (25%) for only $250,000.  Jack's shares drop from being worth $1 million to only $937,500.  The value of the company is $1.25 million.   Or some combination of smaller changes that balances.