How a podcaster leveled up his creative business with strategic hiring

Drew Ackerman’s bedtime story podcast, Sleep With Me, aims to “help grownups fall asleep in the deep dark night.” Whether listeners are pursuing a peaceful snooze, seeking relief from insomnia, or just enjoying a wind-down ritual, Drew — playing the role of “Dearest Scooter” as narrator — lulls folks into dreamland through “slow and meandering” tales, serial stories, and more. Today, the beloved podcast garners millions of monthly downloads.

It’s a smashing business success for a project that started as a hobby. And one that, since its launch in 2013, had largely been maintained by Drew alone.

The challenge: more growth than one person could manage

In 2016, the show hit a critical mass of listeners. Soon, it was winning awards and featured in Esquire and Fast Company. Drew brought the project to Patreon around that time, and his membership business took flight. The steady monetary support meant, among other things, that Drew could hire a production team, including an editor and transcriptionists. But when it came to the day-to-day business, Drew was still running it all.

As the show’s popularity increased, so did the pressure — not just to make great episodes for sleep-seekers, but to make sure the business was sustainable. Drew could only really maintain — not build — the business if he wanted to still carve out time to make a great podcast, which, as the business’s raison d’être, was essential.

Drew found himself facing what he calls a “relatable, though not necessarily reasonable,” fear. Even though his time was stretched thin and his bandwidth was dwindling, he worried that by letting go of something he’d long carried, he’d potentially rock the boat and somehow hurt the podcast. It felt like an existential question: “If I give up control, will everything fall apart?”

An extra set of hands could help carry some of the competing tasks that the business and show itself required, while giving Drew time back to invest in the relationship with his listeners and members, but it took time for him to really see it as the right next step. Day-to-day mechanics seemed safe to hand off, but what about the sort of nuanced decision-making and creative tasks that feed into Sleep With Me’s special sauce? Plus, hiring for something as personal as the podcast felt like something of an unknown. “I didn’t know if someone would be interested in that,” he shares. “I thought it might be easier to do it myself.”

The solution: hiring help to share the workload

There’s a saying that the things you love are like a butterfly, and if you hold them too tightly, you could crush them — a metaphor that influenced Drew’s decision about how to get his time back. “Knowing your weak points is a good thing,” he says. “When you’re looking to find someone to work with, it helps you find a fit.”

It was time to make space for someone to help run the business side of Sleep With Me.

Soon, he connected with an expert in membership business management for guidance. Together, they defined a new role — a page manager — and hired someone to help run the day-to-day operations. As a result, Drew was not only helping the world get some sleep; he was finally able to get some rest himself.

The outcome: business growth, community engagement, and a fresh perspective

Hiring help enabled Drew to redirect his time to the things that mattered most, confident the business and his members were well taken care of. Not only did the fear of breaking the business or damaging his relationship with fans not come to fruition, bringing on a team member actually had quite the opposite effect:

Fan engagement increased. Drew’s newfound availability to connect more deeply and regularly has, in turn, invited his audience to participate more. He says, “I’m getting more inbound [messages] and people giving their opinions.”

The community got a new means of interacting. Drew says that having help from someone “who has a point of view and can give me constructive feedback while looking to understand the audience” was a boon for strategic community-build efforts, which would have been out of reach when Drew was handling everything alone. With an experienced page manager handling the logistics, the Sleep With Me team could now provide and maintain a Discord server for its listeners. A popular addition, the server exceeded 600 members in the first two weeks after launch!

Drew had more time to focus on creativity and community. Letting go of worries and bringing on someone experienced to help keep the Sleep With Me machine humming along has taken a weight off Drew's shoulders. “Having some assistance with my focus has freed up my time to communicate with my patrons and meet them where they are,” he says. “Having help to clear up that headspace [makes me more available to create] the things that listeners and patrons enjoy.”

Plus, Drew was able to focus on outside projects to give back to his community. These projects include teaming up with The Midnight Mission, where he has helped start a newsletter highlighting their work to combat homelessness, assisted with fundraising, and shared the non-profit's progress with his members.

The takeaway? Let the butterfly fly.

Prior to hiring, Drew defaulted to staying up late to get things done or putting personal things aside instead of giving himself permission to ask for help.

“Every time I’d try to grow my Patreon by some percentage in the past, it had failed because I was crushing the butterfly in my hand instead of letting it fly,” he says. “[I’d been] more caught up in the fears and the mechanics than what I needed to do to achieve success.”

As Drew acknowledges, creative work and businesses are, in so many ways, “about the process.” Part of his process was to embrace hiring as a way to grow and make the business more sustainable, which led to stronger connections with the listeners who make his efforts all worthwhile. He says, “Asking for help and accepting help usually works."

Keep exploring the Creator Hub for more ideas on how to grow your creative business.