With 22.3 miles left, Olds found herself in a breakaway and staring down a possible Olympic victory only five years after taking up the sport.
Then suddenly, the fickle fate of cycling grabbed her. She suffered a flat and fell off the blistering pace set by Russian Olga Zabelinskaya and top-ranked Marianne Vos of Holland.
Olds could barely hang on to keep up with the peloton, the main group of riders who chased the leaders through the rainy London streets on a cloud-filled Sunday afternoon. She finished seventh.
In the end, Zabelinskaya, Vos and Britain's Lizzie Armitstead rode away from the pack and all that was left was the question of who would take the gold medal. It would be Great Britain's first medal of the London Games.
Vos won gold in 3 hours, 35 minutes, 29 seconds, with Armitstead taking the silver in the same time. Zabelinskaya was two seconds back in third place.
Olds crossed in 3:35:56, the top finisher among four Americans.
"Bike racing has a lot of luck on its side," said U.S. rider Kristian Armstrong, who finished 35th. "It was particularly bad timing. First, there was the wheel change. Then it started dumping [rain]."
She added the Americans couldn't regroup after Olds' misfortune.
"It was very technical. We couldn't get past anyone. We couldn't see."
American Evelyn Stevens was 24th and Neben Amber placed 36th.
The 89-mile race longest in Olympic history started and finished on the expansive grounds of the Mall. The course cut through such fashionable London neighborhoods as Chelsea, Fulham and Kensington before doing a two-lap circuit of Bunker Hill.
Vos rolled to the starting line as one of the world's most versatile cyclists.
She had won a world championship in road racing, cyclo-cross and track. The 25-year-old even had an Olympic gold medal in points racing on the track.
The world's No. 1-ranked rider came to London with 14 victories, including the overall title at the Giro Femminile this month.
Olds' journey to the Olympics was not typical because it usually takes years to become a savvy road racer. She took up cycling when she moved to Gilroy with her family in 2007.
Olds graduated in 2003 from Roanoke College, where she was captain of the soccer team for two seasons. The cyclist landed in Gilroy when Sun Microsystems transferred her father to Silicon Valley. With a degree in health and human performance, Olds worked for medical clinics before focusing full time on cycling.
The 5-foot-2 rider started on the track, but when the International Olympic Committee eliminated one of her specialties, she switched to road racing in 2010.
It turned out Olds excelled in sprinting, which was perfect for the London course. She won the 2010 and '11 national title in the criterium after winning consecutive track titles in 2008 and '09.
"I know I'll be happy if it comes to a sprint," she told reporters before the race.
Olds had spent the winter in exile from her boyfriend to prepare for London. She lived most of the time in Girona, Spain, a hotbed for American cyclists. She performed so well in the spring racing season that U.S. coaches named her to the four-woman team that included veterans Armstrong and Neben.
"My body will be ready for the event," Olds told VeloNews.
But in London, it wasn't meant to be.