First off, your message is a bit confusing to me. He cashed out $1,100 from which you received 25%, or $275. Where does the remaining $1,725 come from, rakeback? If so, did he pay you 25% of his rakeback or 100% of it? Either way does not make much sense, and funding your playing through rakeback is not the sign of a winning player that you should stake. It seems more realistic that he lost $900 playing poker and found another way to pay you back the $2k, thus saving embarrassment and financial guilt (even though the agreement was that you would risk a 100% loss). Just a guess.

Edit: I noticed that a few other posters responded with the preceding question. It’s obviously an important factor to understand.

On another note, you earned 0% on your investment over an unknown period of time. There are plenty of low risk bonds, funds, etc, that you can invest in for >0% return.

And finally, why would your friend need staking if he is a winning player? It sounds to me, from the facts given, that he is a troubled gambler playing outside of his limits. Stay away.

-Andrew