Riddell said some of the homeless people he's met know how to cope with the cold.
"It's still no excuse," he added. "No one should have to live out on the streets, no matter how used to the cold they are."
Riddell believes his journey will encourage others to help those in need.
"Judging from the responses I've gotten online, this project has already been successful," he said.
On Sunday Jan. 2, Riddell's blog had 980 followers. Five days later, more than 2,000 people were tracking his journey online. Since he started the project, about 20,000 people have visited his website.
Riddell is "surprised and overwhelmed" with how much support and attention he's gotten online -- especially when those people have volunteered to help his cause.
One day Riddell met Joshua and Elizabeth, a young homeless couple sleeping on top of a trestle, about 500 yards from a Marriott hotel in the city. Two days later he learned the structure the two called home was to be torn down.
Riddell posted a Facebook status asking his followers if they could help the couple. Within 30 minutes, he received a text from a woman willing to donate money to put the two in a hotel for the night.
"It's just crazy," he said. "It's amazing that I'm reaching so many people, and it's amazing that they are so willing to help."
ABCNews.com contributor Meg Wagner is a member of the ABC News on Campus bureau at the University of Florida.