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Helping People Sleep Better One Beanie Sleeper at a Time

By Sleepably


There are a lot of people doing a lot of interesting things in the world of sleep, but you might not get to hear their stories.

In this blog, we get to know these people with big hearts, big ideas, and big goals, and find out what drives them to help others sleep better. If you’re looking for interesting and inspiring stories, you’ve come to the right place.

Today we’re connecting with Ben Wolff, creator of a new product called the Beanie Sleeper. A hospital stay prompted Ben to create something to help himself sleep, but his journey led him to help a group of people who truly need an extra dose of healthy rest. Here’s Ben’s story.

What was your background prior to creating the Beanie Sleeper?

I grew up in Los Angeles and I went to college for acting. I moved to New York City in 1999 and haven’t looked back.

While I decided that acting was just not for me, I decided to use my skills as a fashion stylist to venture out on my own. Re-Dress was my first endeavor as an entrepreneur. I really loved it and had a bit of success. I found a niche with business executives and their spouses. It was really moving along until about 2008 when the economy fell apart and I lost all but two clients.

About a year after that, I decided to start another business. This one was called FasterPants. I created the FasterPants Outfit Recommendation Engine. In a nutshell, men’s clothing goes in and perfectly matched three- and four-piece outfits come out. I learned a heck of a lot from that venture.

Where did the idea for the Beanie Sleeper originate?

Who plans to get sick and go into the hospital? Not me for sure. I don’t know if you’ve ever been in a hospital, but when you’re there, you have doctors, nurses — everybody’s trying to take care of you.

And I guess the worst part about being there was not sleeping. It’s always bright in the room. Somebody’s always coming in. They leave the door open, the hallway lights are on. My first four nights, five nights there, I was exhausted every day because I wasn’t sleeping.

It was October 2019 and I remembered I came in with a winter beanie. What I hated about using a regular beanie that way was that it was really hot, the fabric laid directly on my eyes, and there was so much fabric on the sides and back that sleeping on my side was very difficult.

That really was the idea behind it that if I’m ever in that situation, I wanted to be able to sleep. And I just took that idea because I’ve started things before, and I used all of that knowledge to create Beanie Sleeper.

What were your next steps after you had the idea?

I’ve never actually made a product with my hands, fabric and sewing and all that. But after my experience in the hospital, I just really wanted to make something that I could use and I would like if ever I was in that situation again. And that’s what Beanie Sleeper was all about. 

So I started working on it about the first week of November 2019, literally buying all the things I might need from Amazon. I bought traditional winter beanies because I knew I was going to be cutting them up and I knew that was the basic shape. I bought velcro, and I bought a needle and thread. I looked at YouTube to help me learn how to sew. I mean, I didn’t know how to sew, so I was learning the basics. 

I kind of came up with a working prototype and was very fortunate that one of my dearest friends is a fashion designer. He very graciously stepped up to help.

Will you describe the Beanie Sleeper and some of its distinguishing features?

At its core, Beanie Sleeper is a specially designed cotton head-wrap with a built-in contoured sleep mask. But it’s so much more than that.

The built-in contoured sleep mask is so the fabric won’t lay directly on your eyes. The shape of the hat is designed to have less fabric on the sides and back so it’s more comfortable for sleeping on your side or back.

Lastly, no overheating. It has moisture-wicking 100% cotton fabric along with a single fabric layer, and the mesh inner lining on the dome of the hat allows heat to escape while keeping you warm and cozy.

Have you always been interested in sleep, or did the Beanie Sleeper lead you to it?

So what happened is I started sending these out to friends of mine to see how they would use it. And I would get like, “I love this during the weekend when I want to sleep in,” or, “I use it when I want to take a nap.” 

So I’m getting all this feedback and one of my friends had a really bad migraine and he also had a Beanie Sleeper. And I said, “Don’t think I’m a jerk, but would you mind wearing this while you have your migraine to let me know if it helps you?” And it did.

So that’s when I started reaching out to blogs on migraines, on sleep, on these other things, because, you know, I think this could help. It’s a drug-free way to sleep anywhere and sleep naturally and not rely on your melatonin or rely on your prescription drugs like Ambien, which I absolutely hate.

So that’s really what led me to sleep. It wasn’t a smooth transition because of the pandemic, but it was inevitable because of how I designed this and what I designed it for.

How did you get involved with helping cancer patients with your product?

So here’s where it gets interesting. March 15th, the day before lockdown in New York, I really thought Beanie Sleeper was going to be a sleep, travel, and college product. That’s where I thought I was going to be leading the charge.

Then March 16th happened. Lockdown in New York City. In an instant, travel was gone, colleges were gone, and sleep became impossible because nobody in the big box stores would take my call.

I needed to pivot and I needed to do it fast. Back when I first tried to sell Beanie Sleeper, it was on Etsy. I was researching how people were finding the Beanie Sleeper and the term Chemo Beanie popped up. I had no idea what this was. So through my research, I found out that this term referred to a kind of head-wrap that people going through chemotherapy would wear to cover their heads due to hair loss. Then I took a chance and sent an email to mastectomyshop.com.

I told my story and asked if they could try the Beanie Sleeper. The email I got back from her was amazing and unexpected. Beth, the owner, wrote, “I wish this was around when my daughter was in the hospital.”

So I started this part of the journey with renewed energy because now I just wasn’t selling a beanie, I was selling something that would help people in their most vulnerable state. 

So I started this part of the journey with renewed energy because now I just wasn’t selling a beanie, I was selling something that would help people in their most vulnerable state.

Ben Wolff

I always wanted to get back to sleep, but I also want to be good at what I do. And I really wanted to help out this community. Actually, Lemons of Love and I have been trying to work out a way to work together. They work with a lot of gift baskets for chemo patients. So I’m going to be working with them now, and I’m very happy about that.

I was talking to Jill (from Lemons of Love) and she was actually on her way to a cancer center in Wisconsin where she’s bringing about 70 chemo packages. And these are important because it tells somebody that you’re cared for by somebody who knows. So they know what should be in there, like lotion and things to make that taste go away.

I’ll tell you this: I truly believe you can make money and do good. I’m a big believer in that. The likes of Tom’s shoes, the Kind Bar, and there are many, many of those types of stories. I mentioned that I wasn’t really seeking out the cancer community. It kind of found me and I found a lot of meaning in that.

Where did your entrepreneurial spirit come from?

So my dad passed away about four years ago, but my dad was really the first entrepreneur I ever met. At age 50, he and my mom took a second mortgage and he started his own distributing company. My dad was in sales forever, but he knew he could do it better. And so he actually did. He started his own beauty distributing company in the San Fernando Valley.

That was really interesting, is it became more than just selling to beauty salons. He actually found a niche within that of used furniture — used sinks and chairs and furniture for people who wanted to build new salons but didn’t have money for new furniture. My dad found that niche and that’s what he did. And that became really successful, but he tired of it. My mom ended up taking that over and my dad became a real estate agent. He didn’t like that. So he became a loan broker. He didn’t like that. 

He actually found another niche of these businesses of carwashes and mini-marts. And my dad became that guy that you go to if you want to get a loan for your mini-mart or carwash. So my dad was my inspiration for that. He passed away four years ago, so he’s no longer there. But I still will always know what he’s done.

What are the next steps for you and Beanie Sleeper?

My immediate goal is to sell Beanie Sleepers because if I can do that, I can do my other things. I love that I’m going to be working with Lemons of Love. I love that you’re doing an interview with me sight unseen. You’ve never worn a Beanie Sleeper but you were moved by the story and the product. So that’s super important to me, because if you tell people about me on your blog, they’re going to hopefully go to my website or even contact me to say what’s happening or what’s going on, which is totally great.

So that’s really short term. I mean, yeah, I’d like to be a great brand. I’d like to add on to Beanie Sleeper in some capacity like other products. Absolutely. But right now I’m a big believer in small wins and doing things step-by-step.

How to get your own Beanie Sleeper

Interested in trying the Beanie Sleeper, or know someone who could use one?

Visit Ben’s newly launched Beanie Sleeper website to learn more about the Beanie Sleeper and choose the color that suits you best.

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