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Tiffany Shlain | Money Tales Podcast Guest
Money Tales

The Value of Failing Young with Webby Awards Founder, Tiffany Shlain


Our Money Tales guest, Tiffany Shlain, knows a thing or two about success. She also believes a healthy dose of failure at a young age helped her in her future pursuits and successes. Tiffany graduated college with enough exuberant confidence to start a feature film … 40 locations, 100s of actors … and she totally failed. Tiffany ran out of money and the way she got out of debt was to work in technology, which was another passion of hers growing up. So, she went into debt and had too much pride to ask for help. She went through a really difficult time and fell into periods of depression. This experience grounded her in such humility that she can still taste today. This is just one of many stories Tiffany shares with us in her journey and how money has played a role.

Tiffany Shlain is an Emmy-nominated filmmaker, founder of the Webby Awards and author of the national best-selling book, 24/6: Giving up Screens One Day a Week to Get More Time, Creativity, and Connection, which recently won the Marshall McLuhan Outstanding Book Award. The book came out in paperback the week of October 19th. The Museum of Modern Art in New York premiered Tiffany’s one woman “Spoken Cinema” performance, Dear Human, in February 2020. She lectures and performs worldwide on the relationship between technology and humanity.

Tiffany has received over 80 awards and distinctions for her films and work, including selection for the Albert Einstein Foundation’s initiative Genius: 100 Visions for the Future, being on NPR’s list of Best Commencement Speeches, and being named by Newsweek as “one of the women shaping the 21st century. During quarantine, Tiffany has been writing weekly newsletters, giving online talks, working on a film for the election and is hosting a #ZoomChallahBake with special guests and people from all over the world. For information on her book, baking, films, lectures and her newsletter Breakfast @ Tiffany’s, visit and follow Tiffany on Twitter, Facebook and Instagram.

During our conversation, Tiffany talks about how meaningful it has been for her family to keep her deceased father’s home. This inspired today’s financial insight at the end of the interview where we cover considerations for when you want to keep a home in the family for future generations to enjoy.

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