The Million Dollar Collar Story with Rob Kessler TB

Rob Kessler’s Million Dollar Collar Story

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Welcome back to the Daily Mastermind, George Wright III with your daily dose of inspiration, motivation, and education. And we are getting ready to drop some massive value for you today. I'm excited because we're here with Rob Kessler, who is, by far, one of the most diversified guys I've talked to in the last little while.

Rob's an inventor, a businessman with 20 years in sales across multiple industries. He's the inventor of the Million Dollar Collar and now another shirt line, Go Tieless. He's got all kinds of history, which we're going to get into, and I'm really excited to have you here, Rob.

Thank you. Thanks so much. Good to see you.

Yeah, it was great because we were able to talk before we got going, and we've just got so many things to cover. One of the things I noticed is that you're just super passionate about what you do, which I think a lot of people feel stuck in where they’re at. They just don’t follow enough of their passions.

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Early Entrepreneurial Journey

So let’s go back a little bit here. Can you give us a little bit of an entry into the entrepreneurial world? Were you like six years old doing lemonade stands, or did you make a transition into entrepreneurship? Tell us a little bit of the backdrop. Let’s take a few minutes on that.

Yeah, no, my dad had started a business when I was, I think, two or three years old. By the time I got to be seven or eight, really weird, but he would give me my allowance, which was like five bucks a week, and then lunch money for the week on Sunday night.

He would do it for me, my brother, and my sister and be like, “Okay, if you want to be an idiot and spend all your money on Monday and Tuesday, you’re gonna starve on Wednesday, Thursday, Friday.” So oddly, at 10 or 11 years old, I was getting financial schooling and trying to be responsible with money pretty early.

So I was fortunate to have my dad do that. At the same time, I was cutting grass and just always had a— I don’t know, I just feel like I got this entrepreneur thing from him. That’s where that started. One of my first jobs in high school was at a little soccer and volleyball store. The guy, on day one, handed me a key to the store, gave me a code to the alarm, and said, “You’re part of the team. This is your business now too.”

He made me feel, at 17 years old, like I had some ownership in the business. It was cool because I started doing inventory, ordering, a little bit of accounting, and sales. I would go up at night, tear the whole store apart, and remodel and relay everything out. He was like, “Whatever you want to do, man.”

Wow. So you had an owner mentality. Was it because he started that, or did you develop that? There’s not a lot of people out there right now with an owner mentality. Obviously, most of our listeners have that mentality because that’s what they want to pursue. Did you have a job and an owner mentality, or did that situation set you up for it?

I guess, looking back, I did. I did the lawn cutting, and since I got an allowance from Dad, I only got $5 to cut his lawn, but all the neighbors paid me $10–$15. So I was like, “You’re last.”

No special favors from Dad for sure. Okay.

Yeah. At 12 or 13 years old, I was walking with the lawnmower, and I thought, “Somebody’s gonna drive by and see me cutting this grass so well that they’re going to hire me to do their grass.” That’s literally what I thought while pushing the lawnmower at 13 years old.

I’m gonna put a pin in that for a second because I talk all the time about how it doesn’t matter whether you have a job, a business, or if you’re doing something you don’t believe is your end game—how you do anything is how you do everything. Whether you’re mowing a lawn at 17 or stuck in a job at 40, how you approach anything determines your trajectory. Would you agree that having that owner mentality is what put you on this path?

Yeah. I can’t remember who said it, but there’s a quote about providing more service than anyone expects, and you’ll get more back. That always resonated with me long before I ever heard the quote. It was just always putting my best effort out there.

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The Birth of Million Dollar Collar

Let’s transition into something because you made a comment, and I actually brought it up earlier. This is a comment, guys, just in full disclosure, that I brought up myself. I always—when I’m not in a t-shirt and hat like today—I’m usually in dress shirts. Lately, I’ve been wearing them untucked, but this idea of the collar has always driven me crazy. I like collar stays, but the lapel on the shirt always wrinkles up. I can starch it all I want, and it still doesn’t look good.

So I ran across Rob, and he created this company, Million Dollar Collar. I want you to talk to us about how that happened. It’s such a cool story. Sometimes the most amazing and obvious ideas are the ones you look at and think, ‘Why didn’t I think of that?’ Tell us about Million Dollar Collar. How did it come about?

Basically, dress shirts, to me, were always the go-to when I wanted to look good. My now-wife and I, when we were dating, would go out to the bars. She’d look incredible, and I couldn’t go out in a t-shirt, so I’d put on a dress shirt. I hated wearing ties, probably because of my car salesman days when they forced me to wear one.

I’d unbutton a couple of buttons, but the shirt was always sagging and drooping, especially if I wore a jacket. Fast forward to our wedding—I got married on the beach in Jamaica, totally casual, feet in the sand. My brand-new, freshly pressed shirt was a crumbled mess within 30 minutes. It was starched, ironed, and perfect, but the humid Jamaican air ruined it. All day long, I was yanking at my collar, trying to get the front to sit up. You could see my tank top underneath—it just looked terrible.

I came home from the wedding, looked at all our photos, and said, “This is a problem.” I searched all over the internet, and everything was some kind of kitschy collar stay. I loved working stiffs, the magnets that bring the collar in, but they didn’t fix the front of the shirt where the buttons and holes are—the placket.

Dress shirts were designed to be buttoned all the way up and worn with a tie, so they didn’t need structure in the placket. I took the idea of a collar stay, made it nine inches long, and put it down the front of the shirt. That’s Million Dollar Collar. We call it a placket stay—it’s exactly like a collar stay but for the placket. It’s sewn into your shirts.

You can take all your shirts—I’ve done $700 custom shirts, and I’ve done $11 H&M throwaways. It’s for every dress shirt and collared shirt because there’s no structure in the front. If you like that clean business-casual look, we call it the perfect V. When you don’t wear a tie, a lumpy placket is distracting. It’s one of those fine details you don’t notice until you do, and then you can’t unsee it.

Let me comment on a couple of things. Guys, success leaves clues. We all face problems in our lives. Rob had a problem, identified a solution, and executed on it. Success leaves clues. The problem here is one we all deal with—looking sharp and professional. How you look and feel affects your energy, attitude, and performance. Rob, you hit it on the head. People judge you on how you look, whether you like it or not.

Your appearance matters, and this product hits a huge need. Also, you’re solving your own problem, which makes it easier to stay passionate. Let’s talk about the process. Did you just throw a prototype together, or was this years of revisions, investments, and hustle?

From the inception, it was a grind. After our wedding, I started with a piece of cardboard—just to see if a little structure made a difference. I showed it to my wife, and she said, “Oh my God, I finally get what you’ve been complaining about!” But obviously, cardboard wasn’t going to work.

I started experimenting with flexible cutting boards, mini blinds, milk cartons, zip ties—you name it. Then I’d wash, dry, and iron the shirts, and they’d fail. I ruined at least a hundred shirts trying to figure it out. Eventually, I learned that dry cleaners flash press shirts at 450 degrees. Most high-temperature plastics start to fail at 275 degrees, so I needed something better.

I worked with a plastics company and developed this proprietary material. It’s super lightweight and flexible but rigid enough to hold up the collar. It’s soft enough to be sewn through, which is key because it’s secured with stitches where the collar band meets the placket. Once it’s in, it lasts the life of the shirt.

Guys, hear that? He didn’t dabble—he went deep. He learned about temperatures, materials, and manufacturing processes. If you’re going to solve a problem, you’ve got to be persistent and committed. Dabbling doesn’t create success. You need to go deep, learn the nuances, and solve the problem fully. That’s inspiring, Rob.

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Challenges and Persistence

So, you went deep, but I have to ask: Did you face any major roadblocks while developing Million Dollar Collar? Or was it just smooth sailing?

It was far from smooth sailing. After developing the material and finalizing the design, I still had to figure out how to make it scalable. I had to think about the costs, the manufacturing process, and whether this would be viable for mass production.

Even with the product perfected, there was still the challenge of getting it out into the world. I didn’t want to ruin anyone’s shirt, so I didn’t sell a single unit until I knew the material would hold up under all conditions. That meant testing different lengths and shapes. Originally, I wanted the stays to be shorter—because shorter stays would be cheaper to manufacture and ship—but they didn’t work as well. They didn’t give the clean look I wanted. Eventually, we landed on the eight-and-a-half-inch design that overlaps and creates that perfect V.

So, it sounds like you spent a lot of time balancing functionality with costs. That’s not something many people think about when they see the final product. They don’t realize the amount of testing and revision that goes into creating something simple yet effective.

Exactly. Once we had the design, we started pitching it to other brands. We wanted to license the technology to get it into as many shirts as possible. But the response we got from the big brands was always the same: “Sounds interesting, but we don’t know if our customers care about this enough to justify adding it.” So, we decided to sell directly to consumers.

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Expansion and Diversification

And that’s when you started selling directly. But you didn’t stop there—you’ve since expanded into your own shirt line, Go Tieless. What prompted that move? Was it a natural evolution, or did you feel like you needed to create your own brand to prove the concept?

It was both. When we started selling Million Dollar Collar directly to consumers, we got a lot of feedback. The biggest challenge was the installation process. People loved the idea but didn’t want to take the extra step of finding a tailor to sew it into their shirts. So, we started offering pre-installed options. I bought wholesale dress shirts—brands like Calvin Klein and Tommy Hilfiger—and installed the stays myself. Then we sold them as finished products.

That helped solve the problem for some customers, but others kept saying, “Why don’t you just make your own shirts?” After hearing it enough times, we decided to do just that. We launched Go Tieless to create shirts specifically designed for the Million Dollar Collar. These shirts are made from bamboo stretch fabric, so they’re breathable, wrinkle-resistant, and super comfortable. We’ve also added features like convertible cuffs for cufflinks.

So, you basically turned customer feedback into a whole new product line. That’s impressive. But how has that shift impacted your business model? Are you still focused on licensing Million Dollar Collar to other brands, or is Go Tieless the primary focus now?

Million Dollar Collar is still the core of our business. It’s what got us here, and it’s what will keep driving us forward. But Go Tieless is our way of showing other brands what’s possible. It’s a proof of concept. If we can build a successful brand around this technology, it opens the door for licensing deals with other companies.

Our goal is to have Million Dollar Collar in as many shirts as possible, whether that’s through Go Tieless or partnerships with other brands. We’re already in talks with manufacturers in Mexico, Colombia, Brazil, and China, so the licensing side is starting to gain traction.

That’s a smart strategy—using your own brand to prove the value of your technology while still keeping the door open for partnerships.

So, with all these moving parts—Million Dollar Collar, Go Tieless, and licensing deals—it sounds like you’ve got a lot on your plate. How do you balance it all and keep moving forward?

It’s definitely a juggling act. But I’ve always been someone who thrives on progress. Even when things get tough, I just focus on the next step. It’s about setting small, achievable goals and building on them. That’s what keeps me going. And I’ve got an amazing support system—my wife has been my rock through this entire journey. She’s always believed in me, even on the days when I doubted myself.

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Lessons Learned and Advice for Entrepreneurs

You mentioned earlier that you’ve faced some major setbacks, like losing $150,000 in the early years. Looking back, what’s the biggest lesson you’ve learned from those experiences?

The biggest lesson is to trust your gut but also do your homework. A lot of the money I lost was from trusting people who didn’t deliver on their promises. I hired PR firms, marketing experts, and consultants who said they could take my business to the next level, but they didn’t understand my product or my vision. Now, I’m much more careful about who I work with. I make sure they align with my goals and actually understand what I’m trying to achieve.

That’s such an important point. A lot of entrepreneurs fall into the trap of thinking they need outside experts to succeed, but no one knows your business better than you. Any other advice for entrepreneurs who are just starting out?

Yes—don’t be afraid to start small. A lot of people think they need everything to be perfect before they launch, but that’s not true. You’ll learn so much just by getting out there and doing it. Also, be prepared for the grind. Success doesn’t happen overnight. It takes time, persistence, and a lot of hard work.

But most importantly, make sure you’re passionate about what you’re doing. If you’re just in it for the money, you’ll give up when things get tough. Passion is what keeps you going when nothing else will.

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Final Thoughts and How to Connect

Rob, this has been an incredible conversation. I know our listeners are going to take so much away from your story. Before we wrap up, can you share how people can connect with you and check out your products?

Absolutely! You can find us online at milliondollarcollar.com if you’re interested in the original product. For our shirts, visit gotieless.com—and don’t forget to use the discount code DMM15 for 15% off. If you’re on social media, you can follow us on LinkedIn, but I’m more of a behind-the-scenes guy, so I’m not super active there.

Thanks for sharing that. And I just want to say, it’s been amazing having you on the podcast. Your story is so inspiring, and I know it’s going to resonate with a lot of people.

Thank you so much for having me. It’s been a blast talking with you.

Alright, everyone, you know the drill. If you enjoyed this episode, share it with your friends, leave us a review, and don’t forget to subscribe to the podcast. And as always, remember: It’s never too late to start living the life you’re meant to live. We’ll see you next time on The Daily Mastermind. Have a great day!

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About Rob Kessler:

The inventor of Million Dollar Collar and the 1st Shirt Designed to be Worn Tieless

Rob Kessler is the inventor and co-founder of Million Dollar Collar & goTIELESS, a relatively simple solution to fix what his company dubs "Placketitis," the sinking, wrinkling, and folding of the placket of a casually worn dress shirt. goTIELESS is the first shirt designed to be worn TIELESS featuring Million Dollar Collar.

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Guest Resources:

Million Dollar Collar Website: https://milliondollarcollar.com/

Rob’s LinkedIn profile: https://www.linkedin.com/in/robkessleriii/

Million Dollar Collar at Instagram: https://www.instagram.com/milliondollarcollar/

Million Dollar Collar at Facebook: https://www.facebook.com/MillionDollarCollar/

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About George Wright III:

George Wright is a Proven, Successful Entrepreneur- and he knows how to inspire entrepreneurs, companies, and individuals to achieve Massive Results. With more than 20 years of Executive Management experience and 25 years of Direct Marketing and Sales experience, George is responsible for starting and building several successful multimillion-dollar companies. He started at a very young age to network and build his experience and knowledge of what it takes to become a driven and well-known entrepreneur. George built a multi-million-dollar seminar business, promoting some of the biggest stars and brands in the world. He has accelerated the success and cash flow in each of his ventures through his network of resources and results driven strategies. George is now dedicated to teaching and sharing his Prosperity Principles and Strategies to every Driven and Passionate Entrepreneur he meets. His mission is to Empower Entrepreneurs Globally to create Massive Change and LIVE their Ultimate Destiny.

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