He's chronicling his journey on his blog, 30dayshomeless.wordpress.com. Riddell hopes that at least 1,000 of his followers will donate as much as they can afford to The New Family Tree ministry, a group that is building homes for children "aged out" of foster care who would otherwise become homeless.
And with a growing homeless population, he believes the time for action is now.
A new report released this week by the National Alliance to End Homelessness says homelessness in the U.S. increased three percent between 2008 and 2009.
Nan Roman, the group's president, said the issue of homelessness becomes especially pressing when the weather turns chilly.
"In a country like America, people are freezing to death on the streets? It's ridiculous," she said. "It shouldn't have to happen, not here."
According to Roman, there are two solutions. In the short term, emergency shelters are vital to get people in from the cold to save their lives. In the long term, lawmakers must work to lower housing costs so no one has to live without a home in winter or any other season, she said.
"This is a huge issue, and there's no one way to tackle it," Roman said. "But somehow we've got to work together to make sure that everyone has a place they can call home. We've got to look out for our neighbors."
Neil Donovan, executive director of the National Coalition for the Homeless, said cold weather is especially dangerous for homeless communities in normally moderate climates. Cities in the South and other locations with warmer weather may not know how to help those in need when cold weather strikes, he said.
"It's not as big of an issue in communities that are expecting cold winters," Donovan said. "They know it's going to be cold every year, and they know what to do when it does."
Donovan said he saw some shelters in the Washington, D.C. area become disorderly last year when record-breaking chills hit the city.
However, some shelters in warmer locations do have concrete plans in place when temperatures drop.
The Atlanta Mission, a shelter based in Atlanta, has operated smoothly despite the city's unusual snowy weather.
Jim Reese, president and CEO, said that when the temperature drops below 35 degrees, the mission's downtown men's shelter goes into an "overflow setting." Volunteers move tables in the shelter's cafeteria to make way for 100 cots, which are normally folded and kept in storage. With these extra beds, the shelter operates at about 125 percent capacity
"We have a set action plan for cold weather, and if we follow that, we tend to stay pretty organized," Reese said.
He also credits volunteer efforts for the success of the cold weather plan. The shelter's volunteers have pitched in extra time and effort during the past week because "they know how important getting everyone inside is," he said.
"We set up the cafeteria with cots and blankets in 15 minutes flat one day, just because everyone was so focused on the goal of getting people in from the cold," Reese said.
Riddell met one man who sleeps outside every night, despite the evening's temperatures. When Riddell asked him what he does when it snows, the man said, "he shovels a little bit."