Hey Nick, tell me more about how you did it.
I tied a lilne between both rear posts, put a loop in the middle, and then attached a full-length ski-rope to the middle.
Did you head into the wind when you deployed your wakeboarder, then fall off and reach to pull him up?
Tell me the specifics!
When I did this as a kid with my dad (using a small surf board), we tied off like you and used about 30 feet of rope with a handle on it. When we came about (for the initial take off), I jumped off the Hobie, onto the surfboard, slid to the rear of the board and my dad gradually fell off until the line was taught and he was sure I was moving, then he sheeted in and we took off. I think I was about 130 lbs then. I made it onto my knees and tried getting on my feet, but the wind was not steady and I kept over compensating and falling.
After a day or two, we made straps for the surfboard that were big enough to lock your knees into, and just used the board that way. Lots of fun, but typically, pretty sore legs afterward.