Drew Ackerman

Ask Win

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On Ask Win today (Tuesday, October 1, 2019), Best-Selling Author, Win C welcomes Drew Ackerman. Drew is the creator and host of Sleep With Me, the one-of-a-kind bedtime story podcast featured in The New York Times, The New Yorker, Buzzfeed, Mental Floss, and Dr. Oz. Born out of Drew's childhood insomnia, Sleep With Me was inspired by late-night comedy radio, which was the only thing that helped him fall asleep. Created in 2013, Sleep With Me combines the pain of insomnia with the relief of laughing and turns it into a unique storytelling podcast. Drew's stories on the show are inspired by his childhood as the oldest of six children and past jobs as a fuzzy dice and iron-on patch salesperson, fruit fly monitor for the State of California, and librarian for one of the largest jails in the country. Through Sleep With Me, Drew has dedicated himself to help those who feel alone in the deep dark night and just need someone to tell them a bedtime story. To learn more about Drew visit

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