Idea Man

Before I mention this idea I want to preface it by stating that it is probably not legal…. not sure. Anyway, I used to have a stock purchase plan at a company I worked at and it seemed like a good deal if you had money to invest from your paycheck. The way ours worked was you can take up to ‘x’ amount of your check (I think up to 15%) and have it put aside for the stock purchase plan. At the end of 6 months you get to buy company stocks at 15% of what the price was/is, either at the beginning of the 6 month period or at the end, which ever was lower. If you had say $1000 bucks put aside and the company stock was $5 a share at the beginning of the period and it was $8 at the end of the 6 month period, you would get it for $4.15 a share (that is 85% of $5 a share). That is around 241 shares (and I think we had to pay a small fee for the transaction… can’t remember). You can then sell the 241 shares at $10 a pop and it would be worth $2410 dollars…. that is one heck of a return! Even if the stock tanked I think you could still get the %15 profit.
I got to thinking, I work for a non profit so I do not have the ability to get into a stock purchase plan. There are also people within companies that do not take advantage of their stock purchase plans because they live paycheck to paycheck. What if you could enter into a contract with an employee of a privately held company to pay them what they would have taken out of their pay (plus a little extra) so they can max out their stock purchase plan and at the end of the 6 months they agree to flip the shares and give you the profit? I would think tax prep for the person working at the company would be an issue because they have to claim the earnings, you would have to compensate for that. Also, I bet the company wouldn’t be too thrilled about it either, they have better things to do than manage money for investors who use their employees as investing mules. Maybe non profits could get together and have someone run a mutual or hedge fund and offer that like a stock purchase program? Maybe it would be incentive for people to work there since the pay is usually a considerable amount less than in the private sector?