A couple weeks ago I sent a card to Carlton Fisk for a signature.
The card is important to me. You may remember from my TTM tutorial that it is important NOT to send a card you would miss.
However, in the case of Mr. Fisk, he is willing to sign TTM for a specific fee and I decided to take a risk.
I sent a letter of request, a donation to his charity, my 1973 Topps Carlton Fisk (which includes his statistics from the Pittsfield Red Sox who played in my hometown), a Staedtler Lumocolor blue pen, and a SASE. I sent this in a bubble mailer.
In my letter of request, I noted that I included the pen for his convenience and did not need it back. My hope was that he would, in fact, use the pen I included because it is a pen I like for autographs.
Across the board, it was a success. Mr. Fisk signed the card in the Staedtler Lumocolor blue pen I sent him. The approximate time from me sending to me receiving was 2.5 weeks.