Catch Ben Wolff on the #PirateBroadcast™ - russjohns

Catch Ben Wolff on the #PirateBroadcast™

Welcome to the #piratebroadcast™: 

Sharing #interestingpeople doing #interestingthings. 

I love sharing what others are doing to create, add value, and help in their community. 

The approach people use and how they arrived at where they are today fascinates me. 

So… I invite them to become a PIRATE on the

Join LIVE or on the Replay
We live in a fantastic time when anyone with a smartphone and an internet connection can become a broadcaster of some kind.

The internet has opened up the opportunity for anyone willing to create Words, Images, Audio, & Video.

With technology today, you can create your own broadcast. YOU ARE THE MEDIA!

Historically, pirate broadcasting is a term used for any type of broadcasting without a broadcast license. With the internet, creating your own way of connecting has evolved.  

Join the next Pirate on your favorite Social Channel!

Join the conversation LIVE Monday - Friday at 7 AM Arizona Time
for the next #PirateBroadcast™

Listen to the Podcast

Read The Transcript

Audio digitally transcribed by Descript

Introduction: [00:00:00] Welcome to the #PirateBroadcast™, where we interview #interestingpeople doing #interestingthings. Where you can expand your connections, your community, #kindnessiscool and #smilesarefree. Let’s get this party started.

Russ Johns: [00:00:10] Unlocking the mystery of entrepreneurs and #interestingpeople doing #interestingthings. Love the idea that you're here, Ben, thank you so much for being here.

Ben Wolff: [00:00:23] Thank you.

Russ Johns: [00:00:23] Morning.

Ben Wolff: [00:00:24] Good morning.

Russ Johns: [00:00:26] I want to ask you, and one of the things that we're going to be talking about today is the Beanie Sleeper and how it came to be, the origin of the story. Many of you may not necessarily know Ben. So Ben is the founder, the creator, the instigator of the Beanie Sleeper that actually helped you solve a problem. And so you want to go back to the origin story?

Ben Wolff: [00:00:50] Yeah, of course. I think this is a really good thing because this is my third venture. I create things that I need and then I hope other people like it. So back in October of 2019, I was in the hospital for two weeks for medical problems. And during that time, the rooms were always cold.  People were coming in and out, which means doors were opening and  closing and light was coming on and off. And I think the one thing you really need when you're in a hospital is sleep, rest. And that was the last thing I got. And I was putting sheets over my head. I had a winter beanie with me because it was October and I put it on covering like my face up to here, but it was so hot because those things are not meant for that. And I hate eye masks because you get that impression that lasts for hours. I don't like it. So  towards the end, I came up with the idea of, I didn't know it was gonna be called beanie sleeper, but I knew I could do something better. And literally before I left, I found myself on Amazon ordering things, stuff, I've never made a product, but I knew the shape and I ordered like sewing kit and Velcro straps and this and that. I had no idea what I was doing...

Russ Johns: [00:02:06] but you had that seed.

Ben Wolff: [00:02:08] I had a seed because I was like, I should have had something that would have helped me sleep. And I didn't. So that's where the idea came from.

Russ Johns: [00:02:17] Before we started the show, we were talking about some of these things that I was laughing because you scratch your own itch a lot of times, and sometimes it takes off, sometimes it doesn't, but the idea itself is really what's important. And I mentioned  Big Magic by Elizabeth Gilbert, a book about this idea that ideas are out there all the time. And when it lands on you, you have this idea and you take ownership and you take off and you do something with that idea and it goes somewhere else. And then a few years later, you'd go back and you say, I had that idea two years ago. I can't believe somebody came up with it.

Ben Wolff: [00:02:55] True.

Russ Johns: [00:02:55] And it's just one of those things that we either have to do something with it or not. So once you did your prototypes, what was the process? Tell us about that.

Ben Wolff: [00:03:05] So basically I've never made a physical product in my life. I didn't even know what I was doing, but I was like, that doesn't really matter. Let me just get something done. And I got to say, I think that's like the cornerstone of entrepreneurship is the doing. Get something done. Don't talk too much. Just get it done. So that's what I did. And basically, the first three weeks of November, I built a really crude prototype and my next thing was, I need to search for somebody who can make this look pretty. So I moved to the next phase and I'll skip to this part. One of my best friends, Ed Sylvia, he's a fashion designer and the costume designer, and he understands that stuff, talking to him about how hard it is to find somebody and literally at the end of our phone call, he's like, I can do it. And I'm like, what? Cause he's busy, he's super busy. And this is like such a little, little project compared to what he does, but he says, I'll do it. And he's the one who helped me create, what is this? The beanie sleeper. I'm telling you it's good to have friends. It's good to have friends. So he did, he helped me create the first 10. And that was pretty much the middle of February 2020 is when I started to look on how I was going to sell this and I had all these ideas and then March 16th happened and we were locked down and everything changed.

Russ Johns: [00:04:29] Yeah. So what's the process for you now? Where are you at in the evolution?

Ben Wolff: [00:04:35] Sure. January and February, and pretty much up until June of that year, I started looking for factories because I started to get a lot of really people really liked it. So prior to March 16th, I was thinking, oh, travel, wear it on a plane, camping. It's going to be so fun. Wear it in your tent? And then, sleeping and naps. But then March 16th happened and nobody was traveling. Nobody was in college, just weird in the dorm. Nobody was really doing anything, even camping, nothing was going on. I had it up on Etsy. And the thing about Etsy that I like is they let you look at the keywords of how people are finding you. And something came up that I didn't expect. And I had no idea what it was, but it was called chemo beanies. And I was like, what? What's the chemo beanie? So I started doing some research. I put in chemo beanie, I got places like and other store. I'm trying to think of other stores like that online, where they sell these things for people going through chemotherapy or who lose their hair to wear. And I was like, what is that? And I was like, okay. So I started reaching out to places like I basically put an email together saying I created this product called Beanie Sleeper. And I told my story, which I normally don't recommend doing in an email because it's way too much information, but I didn't know how else to reach out and let people know that I understand this dilemma. And I got my email back from Beth. Her name is Beth and she's great. My email back from her was, wow, I wish my daughter would have had this when she was in the hospital and we were connected. And that's how I started to reach out into this chemo community, this cancer community of people who need things like this. And that really changed the trajectory of Beanie Sleeper.

Russ Johns: [00:06:31] Wow. So how did that change your growth potential? Direction of the design or anything did it...

Ben Wolff: [00:06:38] I'll tell you this.  It changed my growth potential in two ways, one, it changed my business and two, it changed me. So originally,  I was telling you off camera that my favorite book is Start with Why, simon Sinek's Start with Why. And my first why was because I needed it. Why am I doing this? I needed something. And I wanted to create that. And I wanted to manifest that. But the second why, which has now taken over the business is because, oh my cat, because...

Russ Johns: [00:07:08] it's not the first cat on camera here.

Ben Wolff: [00:07:10] He doesn't care. He just wants to be pet is because I found that this community would get a lot of use and it would help make them feel a little bit better. So I started really focusing in on that because chemotherapy does not wait if there is a pandemic and it doesn't wait if there's this or that, you're in it. You have to go through this. This is your life. So it was a community that I felt a connection with that I felt I could help in some small way. And that's what changed my trajectory to where now I will say about 98% of my customers are retailers in this space. I sell Beanie Sleeper wholesale for the most part. Of course you can buy it on my site. You can also buy at They're selling it, or you can buy it at mastectomy or you can walk into a fitting experience down in Florida. So there are places, you can even findit on Amazon. One of my other clients I met has an Amazon store and she put it there so you can find it all sorts of places. But the majority of my customers are in this space and I'm diving in.There 's another book I love called the Pumpkin Plan by Michael Michalowicz. I've read it. It's amazing. It's about how to be the biggest pumpkin in your patch and what you need to do that. And I want to be a big pumpkin in this patch and that's how I'm approaching it and yeah that's where the trajectory is right now.

Russ Johns: [00:08:41] I love the idea and I love the creative process and I love the idea and this isn't your first venture in being an entrepreneur and creating something. So what was the seed that planted your pumpkin first? What was the adventure in your life that changed your...

Ben Wolff: [00:08:59] Yeah, I'll tell you. My dad at age 50, decided to strike out on his own. My dad was in the beauty supply industry and he decided that at age 50, he was going to strike out on his own, start his own distributing company. And that was my first time ever really seeing an entrepreneur understanding the process of really putting it on the line. Really risking your retirement or risking your home or  just risking everything. And so it hit me back when I was in in retail at Hugo Boss that I understood how to put outfits together. I understood how to make something small into something big, how to really make looks. And that became redress and redress was about styling business executives. Cause that's what I was doing in the store. I was basically styling business exacts and I decided why can't I do this on my own? And I started that and I got my first clients by basically spamming real estate agents. Because at that time you could literally spam them. Now you can't. But at that time I was sending out emails, click until somebody called me. And that's how I got started there and then word of mouth. And that happened. And I was saying earlier that was great up until 2008, when the economy went to hell, sorry, went to heck. And all my clients were fired. But then that turned into Faster Pants, which is a software company I built. So Faster Pants was basically what I call an outfit recommendation engine, which took the principles of redress, which is how to put things together and created the software that you throw in disparate pieces of men's clothing, suits, shirts, sport coats, trousers, jeans, khakis, ties. This inventory goes in and perfectly matched outfits come out. So you click on a tie, every shirt and pant come out with that tie shown on a virtual mannequin, but this gets into a problem. I created something that I think is cool and nobody else did. So  it was a very expensive failure, but I learned a lot and that's how, so that was a $50,000 failure, but I created Beanie Sleeper and sold my first one for under $500. Yeah. So I learned a lot.

Russ Johns: [00:11:20] That's the bootstrap concept of just, okay, just create something, put it out there, test it and evaluate it. So how has it evolved since the first kind of concept.

Ben Wolff: [00:11:34] Yeah, I had my first I'm sorry for talking over. It's a voice lag thing. So I got my first factory order in, I ordered a thousand pieces. I got that in mid December and now I have sold today about 350 pieces. So I'm getting ready for my version 2.0. So that's already in the work. I'm getting samples made of that. It's going to be great. The colors are chosen. It's going to be really fabulous. I'm doing that.  I've been reaching out to like Ronald McDonald house to try and get something for the moms and dads. Who are having trouble sleeping because right there, they need to sleep whenever and wherever and beanie sleeper allows that because you could literally sleep with the lights on.

It doesn't really matter because it has a built-in sleep mask and it keeps your bed warm without overheating. So I really, again, down this track, I'm reaching out to cancer centers and people and places that do infusion therapies. So I'm still on track, but I've also been reaching out to travel because we're starting to travel again. So it's just listed on a travel magazine called Gold Nomad as one of the top things for the top pieces of gear for spring travel, whether you're camping or flying. So that was really exciting. So the trajectory I'm still on my path, I still walk. The primary thing is the chemotherapy, but, I'm also looking into travel and open markets. And I'm trying to find my way because  I want Beanie Sleeper to be my last job, or I really want to grow this as far as it can grow and then see what's happening.

Russ Johns: [00:13:14] I love that. I want to give a shout out to a couple of pirates here in the room. Good morning from Memphis, Tennessee, Sheila Chamberlain. Thank you for being here, Sheila. I love it. Also Wendy is in the room, always a supporter. Love you, Wendy. Thank you so much for being here. Welcome to the pirate posse, Ben, thank you so much. Trajectory change in 2020, Sheila says. And also she says there is some auto difficulty. I suspect she means audio difficulty. So we're live streaming technology, all of these things that go into it, it's one of those things that we have some control over, but not all control over. So I'm really curious. So the thing that, you know, as you go through this process and you go through this challenge, you as a bootstrapper, what have you learned personally, in your personal growth as an individual about patients and maybe some empathy or how to get through things, even when you're feeling overwhelmed or you're feeling burnout, or all of those emotions that entrepreneurs typically experience. What are some of the things that you've gone through? And how have you dealt with that as an entrepreneur?

Ben Wolff: [00:14:29] I'll start with the most recent one is that, although this is my third business, my third time as an entrepreneur, this is the the furthest I've ever been. So I liken it to this.  I've always reached here and I reached here with Beanie Sleeper, but I have the ability now because I have the need to go here. So I actually, because of that, I hired a business coach. Her name is Stephanie Ray. She calls herself the accountability evangelist and she is right. It's really amazing. So I'm in  her group, her cohort as she calls it. And it's been great because it's not like I built a business plan, but I have a business roadmap now, and I'm able to actually structure this. And this has been a great help because I think as entrepreneurs, we tend to go on what I need in the moment. I need this in the moment, cause we're wearing all these hats, but what this does is it allows me to do my top three of what I need to do and then work my way down the list weekly. And that's been really important on the business side. On the personal side, you talk about patience and I will say that's a big deal because especially in wholesale. The actual wins come weeks and months later of work, it's not like you go to my website,buy beanie sleeper. I instantly get money. You instantly get a Beanie Sleeper, right? It's not that at all. So it really is about patience. I read a lot. Start with Why, The Pumpkin Plan. I am such a big believer in knowledge of the power of vulnerability. Bernay Brown is huge. If you're an entrepreneur, great book to read a hundred percent. I believe in doing, I have two podcasts myself. One is more about Beanie Sleeper called Sleeping with Ben and it's on IG live and I do it on and it comes on to Spotify. I started another podcast with a dear friend of mine. We're both part of No More Mr. Nice Guy, if you know about that book. Again, growth. So we have a podcast called Nice Guy Deep Dive. We take those issues and just go deeper with them. And I think I could talk all day about this kind of stuff, but I feel like growing as a person helps me grow in a business and vice versa. I just feel it allows me more open to things, more vulnerable, so to speak. And yeah, that's what's been going on.

Russ Johns: [00:16:51] So what brings you joy? What do you do for release or self care?

Ben Wolff: [00:16:55] That's an awesome question because I will say this, I just started to learn tennis. Yeah, I've never done it, but I always wanted to, and I just started with tennis lessons and I'm having such a good time. It's funny. I was texting my best friend on Saturday saying I think this is a perfect day and I was describing it because I'm in Astoria Park, I'm in New York City. So I'm in Astoria Park and it was gorgeous out, blue skies, about 65 degrees. I had my mask off because I'm fully vaccinated, I'm outdoors and I'm going to go play tennis. And I was like, I don't think it gets better than this. But I will tell you, in all honesty, in all my years as an entrepreneur, I can honestly say that this is the first time I was able to spend money on something I wanted to do that wasn't business related. Because I always felt guilty. Wow. That X amount of dollars could go towards this. And it's been very difficult to go, wait a minute, I'm different than my business. And tennis has nothing to do with Beanie Sleeper. Zero.

Russ Johns: [00:18:04] I think it's important. And the reason I bring it up is because I think it's critical for entrepreneurs to find something that is not business focused, that you can actually shift your mindset or shift your physical being into something else. And I think it's really critical for us to understand that there is life outside the business, because sometimes we get overwhelmed and we get incredibly focused. Sheri Lally knows that, absolutely true. Absolutely true. She's an entrepreneur from way back. She's created some amazing products.

Ben Wolff: [00:18:43] Awesome.

Russ Johns: [00:18:43] I just feel that it's important message to really get out there. And I love the idea that you're podcasting and sharing some of these things with the community. So what activity have you found that has been most productive in getting your word out? What is it that moves the needle for you in the business?

Ben Wolff: [00:19:04] Really I get most of my customers, my new accounts from emails, basically cold emails. I figured out I have a formula I use and that's how  I had gotten all of my customers through cold emails.

Russ Johns: [00:19:19] Just rolling up your sleeves and getting on the keyboard?

Ben Wolff: [00:19:21] Honestly, I'm talking to my coach today just saying it's very tedious. It's incredibly tedious, but I just have to keep my head down and keep moving because it will be to something. Because, and it's not something I'm making up, it's just, it's actually worked. So I'm taking what's worked and I'm just applying it to different levels of customer, the cancer centers, hospital gift shops things like this. And it's very tough, but I have to keep my head down and that's what I'm doing. That's been the most productive. So my podcast, Sleeping with Ben, I talk to interesting people about their lives. I want you on my podcast, but the whole premise isSleeping with Ben is I'm in my bed, I shoot it from my bedroom. I'm in my bed. I have my Beanie Sleeper on this and we're chatting. And by the way, this is the Beanie Sleeper and honestly we just chat about their lives and what they're doing in the world. And we do talk about sleep and I want to know what their sleep rituals are, but the majority of it is just fun. I love live. I love live. I only edit the beginning and end. Because sometimes there's dead space in both. I never ever edited in the middle. I don't because I want it all there. That's the fun part of live

Russ Johns: [00:20:37] I'm right there with you. I'm right there with you, Ben. I'm live. We're live on multiple channels.

Ben Wolff: [00:20:43] I love it.

Russ Johns: [00:20:44] Twitch, Twitter. Yeah, YouTube, Facebook, LinkedIn.

Ben Wolff: [00:20:49] I absolutely love it.

Russ Johns: [00:20:51] But that brings you joy as well, right?

Ben Wolff: [00:20:53] Oh, 100%. When I'm in it, I love it because I have a set of questions, but we hardly use them because we start talking about other stuff. And I find the other stuff because it comes naturally from my guests. I want to expand upon it. I don't have the need to go question number three. I never do that. I don't like to do that. I like the spontaneity. I like the authenticity I get. And it makes me more in the moment and authentic and I just think we become two people talking.

Russ Johns: [00:21:25] And that's the beauty of what we can do now. Right now in this world, we're so able to connect, have a conversation. It's not the same as being across the table. Where you're doing something face to face. However, it's the next best thing. And sometimes it's the only way we can connect. I don't have any trips planned in New York in the next few months. I suspect, that's okay that we can have this conversation here and help you shine the light on your product and some of the things that you're doing to help people out in the community that need help. That's the beauty of what this is.

Ben Wolff: [00:22:01] I really believe, I love what you're saying. I really believe you can have a business and do good. You can make money and do good. Start with something that matters, the story of Tom shoes. Great book. Do the kind thing. Daniel Lubetsky, the story of the kind bar, great book. It is possible. I get people who want me to donate Beanie Sleepers and  I want to donate so bad, but I can't, I'm a small business. I just don't have the capital, but I want to and I try and I do things if I can, but I can't yet, which is really what it is. I can't yet, but I will say this though, something has been a real big blessing for me is meetup. because I belong to meetups all over the country. And I've gone to several Meetups in Canada and in the UK, I've met amazing people in Peoria, Illinois. I have a new mentor, Ross Miller. He's amazing. I have a meetup I go to out of Seattle. That's amazing. I have met such amazing entrepreneurs and people who are... oh my gosh, the Rochester Open Coffee Club in Rochester, New York. Amazing people who are willing to give. If I can say anything to new entrepreneurs, there are people who want to help you. And for no other reason than they want to help. No other reason. I mentor very new entrepreneurs for no reason other than I love it. And I love where they're going. And I love watching where they're going and helping. That's it.

Russ Johns: [00:23:27] Watching the excitement of somebody or something, creating something from nothing is amazing.

Ben Wolff: [00:23:32] A hundred percent. It's amazing. It's a true gift. And you want to talk about joy. That brings me so much joy. I almost feel selfish doing it because I know, I just know I'm getting so much out of it and I'm just hoping they get something out of it.

Russ Johns: [00:23:47] Oh, I do too. And often, it evolves into a relationship that lasts for years.

Ben Wolff: [00:23:55] Yeah.  A hundred percent, right. It's really fun.

Russ Johns: [00:23:57] Sarathy says, hi Russ and Ben. Angie says, good morning, everyone, pirates. Sneaking in the last minute. Love it, Angie, thank you so much.  I love the support of the community and with anything, Ben, there is a community around it. You build a community and you'll always be able to reach out, get some feedback, email people and get some answers. Introductions. Build relationships. We're living in an amazing time and being able to live stream.

Ben Wolff: [00:24:29] A hundred percent.

Russ Johns: [00:24:30] We've got out there. And that's what I really am passionate about is helping people get to the point where they can do this. And so that's my mission.

Ben Wolff: [00:24:38] Thank you. You have no idea how much I appreciate this experience and talking with you. I think you're fabulous and I do want you on my own podcast. We'll figure that out. I know I'm totally recruiting you. Yeah, you'll have to wear your Beanie Sleeper. I'll get one to you.

Russ Johns: [00:24:53] Perfect. I have spent many nights in the hospital over time. I've damaged about every part of my body at some point in my life and required many hospital stays. So I would love that and I've traveled a lot. It would be wonderful, but It's really, in fact, it reminds me when I was a kid, I used to collect hats. And I had one of the old white sailor hats, that I would fold down and I could put it over my eyes like that. Ben, it's been a total pleasure and an enjoying moment in the day and it sets the tone, gets thingsgoing right and awesome. Appreciate you being here.

Ben Wolff: [00:25:32] Thank you so much. I appreciate it.

Russ Johns: [00:25:34] So how do you like people getting a hold of you?

Ben Wolff: [00:25:37] The best way is to Instagram or Facebook at Beanie Sleeper. That's really the best way to get me. Or you can always go to my site, There's a form if you need to email me, but the best way is Instagram at Beanie Sleeper.

Russ Johns: [00:25:50] Perfect. Thank you everyone for being here. Love the fact that you're here. And if you have anyone in your network or your connection that could create some value out of the Beanie Sleeper and what Ben's doing, please share it out, send it off to someone that needs to know about it, or can help understand and appreciate the support and the benefit of being here as a pirate. Because you know why. #kindnessiscool, #smilesarefree and you #enjoythe day.

Ben Wolff: [00:26:25] Thank you so much. I appreciate it. Bye everybody.

Exit: [00:26:29] Thank you for joining the #PirateBroadcast™. If you found this content valuable, please like, comment and share it across your social media channels. I would love the opportunity to help others grow in their business. The #PirateSyndicate™ is a platform where you show up, we produce the show. It's that easy. If you want to be seen, be heard and be talked about, join the #PirateSyndicate™ today.

Join the next #PirateBroadcast™ on your favorite social media channel.

Share, Like, and Connect