Drew Ackerman 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, CBS Sunday Morning, and Nova. 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. His childhood inspires Drew’s stories on the show 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.

I want to put my best foot forward to help people fall asleep. Early on, there were things I had no idea would be problematic for listeners, like snakes and spiders, because I was oblivious.

I consider the listeners a part of the production team because they give me feedback about what doesn’t work. We just had an episode, I think it was called “The not singing song of friendship.” But I wound up taking “not” out of the title because I’ve gotten feedback in the past about anything negative, even a negative word, might cause people to just avoid the episode altogether. Money, food for some people can be a challenge, politics, heights. I try to steer around anything that’s archetypally disturbing, and sometimes what turns people off can be just a single word. 

I’m afraid to say this out loud, but right now I almost have too many ideas. Episode ideas can pop up out of my control. But if I’m paying enough attention, I can grab them.

Something to remember, especially for people new at podcasting, is your show will grow into itself over time. I know mine did. I was trying to figure it out as I was making it.

Sometimes, when I make the show, I feel like I’m pulling teeth. Other times, I feel like I’m skiing down a slope.

I work on the show mostly at the last minute. My experience has been when I’ve finished an episode ahead of schedule, that’s when I make mistakes. I don’t know if that’s a self-destructive tendency or what. 

When listeners expressed interest in a live, in-person version of the show, I was scared to do it. Which was the same thing that kept me from starting the podcast sooner. After I did a couple live shows at conferences, it was like, okay, maybe I could try to do this on my own and figure out how to get more comfortable with it.

I’ve thought a lot about the idea of value for value. I was afraid of listeners being mad or pushing back. But I was at a point where I had a full-time job and I was putting out three episodes a week. I was just like, “How am I gonna keep doing this?”

With my show, I’m kind of thinking about it from a service mentality. If you’re using this as a service, what do you want out of the service? And is there some way I can provide that?

I convinced myself, out of fear, that I might be able to get 10% of my audience to support me at $1 per month.

Again, listener feedback really helped during this process. Two separate listeners I had gotten to know were like, “Is that really what you think your show is worth? Don’t you work on it a ton? You’re really only asking for $1?” And someone was like, “Are you sure this isn’t your self-esteem or your fear of getting in the way of things? Are you doing what’s best for you and the podcast?” That was so helpful to get that honest feedback. Subscription services and crowdfunding helped turn the show from a hobby into a full-time gig.

Sleep with Me recently crossed the 10-year mark and 1,220 or so episodes. It’s wild to say that.