If an owner has 50% of the company, and the remaining 50% is spoken for by friends and family, is it possible for the owner to "voluntarily" give some of his equity back to the company (at no charge) so that it can be used to raise more money? For example, he says he's willing to reduce his ownership to 40% so that 10% can be used to raise more money. If he's receiving zero dollars personally, would there be any personal or company tax implications?
The 50% founder shuold currently have an equal number of shares to the 50% "friends and family". If the goal is to reduce the 50% founder's equity to 40% while keeping the "friends and family" block at 50% then you would need to issues shres to the friends and family block as you issue them to the investors.
At Time Zero
This means the founder has 50% equity (10,000/20,000). If you want to reduce the founder's equity by 10% you need to increase the number of outstanding shared accordingly: 10,000/.4 = 25,000 shares. 2500 of those new shares will go to the new investor and 2500 will go to the friends/family.
Once Investment is acquired
Now your equity split is 40%, 50%, 10%.