About twenty iPods.

Walkers, a snack company, was running a contest where you could enter a draw every ten minutes, 24 hours a day, to win an iPod. They also had a website where you could get an entry code without buying anything. I was one of the few people to have unlimited texts and a phone controllable by Bluetooth at the time, so I ran a script to just spam the free entry codes. Somehow they never cottoned on.

When the internet was still young I entered an online drawing to win a vacation on a travel website. I never really thought much of it. One day I decided to answer the phone even though we got lots of telemarketers. The woman was from the travel company and said I’d won a rafting trip in CO and that this had been their third and final attempt to reach me. It was totally legit, they paid for the flight, rafting trip and rental car. Due to low river levels the trip was moved to the San Juan river in UT though. It was an awesome trip. We even paid some extra to keep the rental car longer to add some extra sightseeing days to the trip.

I won some stuff in a church raffle when I was a teenager. Nothing remarkable - i think a suitcase.

I also won some sex toys from a charity raffle for repro rights, but some past partner took them. Not sure who, but I don’t have them anymore.

Thinking about it for the first time now, it is funny how those are two very different contexts.

I was a volunteer working at the first LinuxCon in 2009, I worked in the expo hall and at the end of the first day one of the booths had a raffle to win an android G1 developer phone and I ended up winning.

The best part was, by winning the phone instead of having to buy it through t–mobile I was able to keep my service without having to pay for adding data and it was a couple years before I had to actually start paying for data.

I already won the lottery. Born in the US of A baby!