As a child actress, she made films and commercials from age eight onwards. From 2002 to 2006, she appeared in the TV sitcom
Still Standing as middle sister Lauren Miller. Olstead was presented with the Young Artist Award for Best Performance in a TV Series (Comedy) - Supporting Young Actress for
Still Standing in 2002. She also had a small part in the 2004 film
13 Going on 30. She co-starred in the ABC Family series
The Secret Life of the American Teenager, about fifteen-year-old Amy Juergens's struggle through her unexpected pregnancy and how it affected her peers. Olstead played the character Madison Cooperstein, one of Amy's best friends. In 2004, Olstead released a self-titled album of
jazz songs and
pop standards for
Warner Bros. Records to good reviews. Since her previous releases had limited distribution, this album was considered her official debut. She subsequently performed in Berlin during the
Live 8 concert on July 2, 2005. Olstead also recorded with trumpeter
Chris Botti on his 2005 album
To Love Again: The Duets and appeared on the 2006 DVD
Chris Botti Live with Orchestra and Special Guests. Her singing style is influenced by jazz vocalists
Ella Fitzgerald and
Sarah Vaughan. Reportedly, her musical talent was discovered by composer
David Foster, who produced her 2004 album. She later performed with him on
The Oprah Winfrey Show. '' at
Comic-Con in 2015 A follow-up album entitled
Skylark, also produced by Foster, was originally announced for release in 2005, but it was subsequently pushed back several times, with release dates in the summer of 2006 and early 2007 being mentioned on online retailers such as
Amazon.com. It was then scheduled for a June 2008 release, but was delayed once again. It was finally released on January 27, 2009, nearly four years after it was originally announced. Olstead later starred as Kaitlan in the 2013 supernatural thriller
The Midnight Game and as Jess Felton in the 2014
technology-themed thriller film
Unfriended. On November 30, 2020, she announced that she was launching an
OnlyFans page. Her introductory subscription fee was set at $9.99 per month. She was the
Penthouse Pet of the Month in January 2023 and the 2024
Penthouse Pet of the Year. Since April 12, 2023 she is an associate marriage and family therapist specializing in
sex therapy. She is a sex therapist for the
adult industry mental health support network
Pineapple Support. ==Personal life==