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  • September 21, 2023 21 min read

    The Daily Mastermind


    George Wright III:  Welcome back to The Daily Mastermind, George Wright III with your daily dose of inspiration, motivation, and education.  We are getting ready to drop some massive value for you today.  I am excited because we're here with Rob Kessler, who is by far one of the most diversified guys I've talked to in a while.  Rob is an inventor, a businessman, 20 years in sales, multiple industries.  He's the inventor of the Million Dollar Collar and now another shirt line goTIELESS.  He's had all kind of history which we are going to get into and I'm really excited to have you here Rob.  Welcome to the Podcast.

    Rob Kessler: Thank you, thanks so much, good to see you.

    George:  It was great because we were able to talk before we got going and we just have so many things but one of the things I noticed is that you're just super passionate about what you do.  I think a lot of people feel stuck in where they are at but they don't follow enough of their passions.  Let's go back a little bit here.  Can you give us a little bit of entry into the entrepreneurial world?  Were you 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.

    Rob:  My Dad started a business when I was 2 or 3 years old and by the time I got to be 7 or 8 he would give me my allowance which was $5 a week and then lunch money for the week on Sunday night.  He would do it for me, my brother, and my sister.  He would say if you want to be an idiot and spend all of your money on Monday and Tuesday you're going to starve on Wednesday, Thursday, Friday.  Oddly at 10, 11 years old I'm getting this financial schooling and trying to be responsible pretty early.  I was fortunate to have my Dad do that and at the same time I was cutting grasses.  I feel like I got this entrepreneurial thing from him, that's how it started. 

    Then one of my first jobs in high school was at a little soccer/volleyball store and the guy day one handed me a key  to the store, gave me the code to the alarm and said you're part of the team this is your business too.  It just made me feel at 17 years old that I had some ownership in this business and it was cool.  I started doing inventory, ordering and I was doing a little bit of accounting and sales.  I would go up at night and tear the whole store apart and remodel and re-lay everything out.  It was whatever you wanted to do, a cool environment.

    George:  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.... most of our listeners have an owner mentality because that is what they want to pursue.  You had a job, but did you have that owner mentality or did that situation set you up for that?

    Rob:  I guess looking back I did because I did the lawn cutting and because I got an allowance from Dad I only got $5 to cut his lawn and all the neighbors gave me $15, I was like you're last.

    George:  No special favors for Dad.

    Rob:  I literally kid you not at 12 years old I would be…… stop adjusting your collar

    George:  We're going to talk about that in a second.  Keep going.

    Rob:  At 13, I was walking with the lawn mower and I was basically on a dead end street. I thought someone is going to drive by and see me cutting this grass so good that they are going to hire me to do their grass.  I had this in my mind as I was pushing the lawn mower at 13 years old.

    George:  That's a great point.  I am going to put a pin in that for a second because I talk all the time with people about it doesn't matter if you have a job, you have a business, whether you're actually doing what you believe you're going to end up doing... How you do anything is how you do everything.  If you're mowing a lawn and you're 17 years old or I don't care if you're not where you want to be and you're 40 years old and you're still on a job.  How you have that mentality of doing anything and everything is going to determine your trajectory.  I think that's probably, and I think you would agree what taking that on the path is having that owner mentality, yeah? 

    Rob: I can't remember who said that I think that was Wilt Chamberlain but “provide more service than anyone ever expects and you'll get more back.”  I can't remember what the quote was but it always felt like that resonated with me even long before I heard the quote.

    George:  I find so many people that say I hate my job, because I want to do something else and they don't realize it is not cut and dry, it's how you are as an individual.  Let's transition into something, you made a comment and I actually brought it up early.  This is a comment in full disclosure that I brought up myself. 

    I always wear dress shirts a lot of times. Lately you see me in a t-shirt and a hat whereas most of you know most of my career suits.  I wear dress shirts untucked right now and stuff but this idea of the collar always drove me crazy because I like collar stays and then the lapel on the shirt always wrinkles up and I can starch the crap out of it and it still does it.

    I ran across Rob and he created this company Million Dollar Collar and it seems like the most amazing thing and sometimes the most obvious things are the most incredible things.  Tell us the story behind Million Dollar Collar, what's the deal there, how did it come about?

    Rob:  Basically dress shirts to me were always the go to when I wanted to look good. My now wife when we were dating we were going out to the bars. She looks incredible.  I can't go out in a t-shirt so I put on a dress shirt.  I hated always wearing ties. I think it was probably from my car salesmen days and they forced me to wear one.  You unbutton a couple of buttons and then it was always sagging and drooping especially if you put a jacket on. 

    We got married, I got married on the beach in Jamaica totally casual, fit in the sand.  My brand new freshly pressed shirt is a crumbled mess in 30 minutes, it was starched, it was ironed it was perfect.  All day long in this humid Jamaican air, I'm just yanking at my collar to get the front to sit up, you could see my tank top underneath, and it just looked terrible.  I came home from the wedding, and after looking at all the photos I think this is a problem, I searched all over the internet and everything was some sort of collar stay.  I love Wurkin’ Stiffs, which are the magnets that help bring the collar in, but it doesn't keep it up.

    The front of the shirt where the buttons and the holes are is called the placket and that is the part that has no structure because dress shirts were designed to be buttoned all the way up and worn with a tie so they never had to have that structure in there. I took the idea of a collar stay. I made it 9 inches long and put it down the front of the shirt where the buttons and the holes are and that's Million Dollar Collar.  We call it a placket stay.  It's exactly like a collar stay except it is for the placket. It is sewn into your shirt, you can take all of your shirts. I know a lot of people out there have really nice shirts.  I personally have done a custom guys $700 dress shirt and I've also done $11 H&M throwaway shirts. 

    It is really for every dress shirt, every collared shirt, because there is just no structure in the front.  If you like that clean business casual look we call it the perfect V.  The tie used to be what drew the attention up to your face and you don't wear a tie if you have this lumpy, clumpy placket is just as distracting.  It's one of those fine details that you don't really notice until you notice. Then when you notice you can't not notice. 

    George: Let me comment a couple of things on this and then I want to go to the next evolution of what you're doing.  I want to draw some attention here, first of all I say it all the time success leaves clues.  All of us are dealing with problems every day that affect our life.  Here he had a problem and he identified a solution, which obviously was not an easy process which we can talk about.  Success leaves clues, the problem was and we all face it. If you're an entrepreneur, if you're a businessman, if you ever dress sharp as you should if you ever want to be successful.  A lot of these big entrepreneurs know where t-shirts is because they don't care and they don't need to care. Let me tell you, how you look, dress for success, there's something to it. 

    The second thing is how you look and feel will determine your attitude, your energy and everything.  Rob you hit it right on, we know if you want to look and feel good you're going to dress nice and if you're sloppy... even if you think you have this killer shirt on but it looks sloppy people are going to judge.  Whether you like it or not people are going to judge and I think your appearance will make a massive difference.  So here is something that hits a niche and a need for you but also… that is one of the success secrets: scratch your own itch and something you're passionate about.  I really love that, it probably wasn't simple, I would like you to touch for a second on you cut something out and put something in a shirt and you were good to go or was this like revisions, investments and time?  How long did it take you, I am just curious to evolve the Million Dollar Collar?  And was there a big break at some point or did you just go out and hustle?

    Rob:  From the inception point of our wedding, I came home, the very first was a piece of cardboard, which I knew wasn't going to be a permanent solution but I just wanted to see if a little bit of structure made a difference. I showed it to my new bride and she said, "oh my God I finally get what you've been bitching about all these years trying to get this straight." Obviously, cardboard is not going to work so I went through the house, I had these flexible cutting boards, I had mini blinds, zip ties, and milk cartons.  I tried all those plastics and then I would wash it, dry a shirt, and then I would send it to the dry cleaner and it would completely melt all over the shirt. I ruined 100 shirts trying to figure this out and learned they flash press your shirt at 450 degrees when you send a shirt to the dry cleaners. It's insane heat and even the high temperature plastics start to fail at 275 so that wasn't even going to be close enough.

    I never wanted to invent and sell this $2 product to ruin your $200 or $300 shirt and have to be buying $300 shirts for every $2 product I sold.  I kept working and grinding the patterns, if you look at the different styles, it changed insanely.  There are just a ton of different styles and so I finally ended up hooking up with a plastics company we developed this material.  It's super lightweight, it's rigid enough to hold up the collar but still soft enough to be sewn through.  It just takes a couple of stitches right here where the collar band and the placket meet.  The beauty is that every dress shirt is made the same. There are always 2 layers.  The reason why I have it inside of the shirt is if you look at my placket you can see the inside and you can see the outside.  If you remember in the 90's when girls had the clear bra strap they weren't very clear, they weren't very hidden so with the millions of patterns out there it's literally the second easiest tailoring or alteration that can be done behind replacing a button. 

    We're in 650 dry cleaners and tailors and they all say it's super easy to do.  It is this weird extra step where you order from me and then go drop off your shirts and get it sewn in put once it's in it will last the life of the shirt.  You will never have to think about it again, it's always there and you always look incredible.

    George:  I will say ironically it actually... On one hand, my first thought was oh you have to do a little bit of work but then the logical thing I thought of was God I don't want to go buy 50 new shirts so it's actually cool because I have already invested in shirts, you can do that.  I really loved that.  Listen, guys, I want to point out something else, a lot of you entrepreneurs and business owners and people who are trying new things you dabble, you don't go deep and you don't do what it takes. 

    You heard him mention things like they flash press at 450 degrees and these things will fail at 275 and he tried this and cardboard and blinds.  Listen if you are going to do anything if it's worth doing well it's worth doing and it takes persistence time and commitment.  Everybody listens to the success stories I don't want to brush over the fact that you had to go really deep to know what they press when they press, what kind of materials, how it works, what to do with it, and then to think through self-alteration versus the next evolution that we'll talk about.  That is just a testament for individuals to realize that the key to it was that you were interested and passionate about it. 

    There are a lot of good ideas out there but if you find one tied to your interest and passion you will be able to be consistent, persistent, and go deep.  Dabbling will never make you money long-term, it requires persistence.  You were selling while you were evolving right? You just didn't evolve it till you thought it was perfect and then went out and installed one version?

    Rob:  No. I did not want to ruin anybody's shirt so I did not sell any until I knew that the material wouldn't fail.  Thinking from an entrepreneur's mind I wanted them to be shorter, the material is made in rolls and they are die-cut out.  These are my die-cuts right here.  I'm thinking if they are shorter, I can get more in a roll and it costs less.  Then you would put it on and it would do the Travolta 70's

    George:  Because they were so long or too short?

    Rob:  Now they are about 8 1/2 inches long which will get you past this third button and then because they overlap it just gives you this really nice clean look.

    George:  So that version you have, that's the same version nothing changed on it? It's the main deal?

    Rob:  I have changed the die-cutting process slightly. It's adjusted very minutely.  Overall the whole thing is the same.

    George:  It also flows with the shirt that's beautiful.  So you noticed a need and now you've expanded into your own shirt line.  What's the reason you decided to diversify? Was there a point and time you felt that you had gone deep enough with the Million Dollar Collar that you wanted to expand or did you need it or did you need to fill that need so you expanded?  What was the reason behind it and what did you end up doing?

    Rob:  We went originally on day one when I got the patent and in October of 2015 and in January of 2016 I was in New York with my partner making presentations to all the biggest brands.  We were talking about licensing this and getting it in the shirts and they said it sounds like a good idea but we don't even know if our customer cares that much.  I said, okay we'll sell it directly to consumers and so we started selling this on our website. We got a few YouTube fashion influencers to do reviews on the product.  As time was going on I kept hearing this is a pain to install. I don't want to take the extra step, I don't know how to sew.

    Okay how do I make it easier for our customers to try this out.  I went and started buying wholesale because I had a screen-printing and embroidery business. At one point I knew I could buy shirts at wholesale.  I got a Calvin Klein account and a bunch of brand shirts that you know.  I said okay if you don't want to go through that process why not buy a Tommy Hilfiger shirt that you know and love. You know what size you are so I won't have to deal with returns and exchanges.  I bought them, sewed my product in and then sold these done shirts so you can try it if this is the way you want to go. 

    Then we started doing all these dry cleaning trade shows and got into a bunch of dry cleaners. So we have a VIP service which you can mail in 5 to 15 shirts and we'll sew it in, fold them up and send them all back to you so we have that service.  To me, I always think how can I make it as easy as possible for someone to try my product.

    George:  You were solving the needs along the way with your primary product. I really love that.  I also think sometimes a lot of entrepreneurs have shiny objects and they say I can do this, I can do this but I like how it evolved and went towards a natural evolution and obviously that leads you to the point of just creating your own branded shirt.  For a lot of you if you've been online, watched shark tank, watched any kind of shirt companies.  A lot of shirt companies come out, it sounds like you created from what I can see, a real kick ass shirt.  Tell us what you went through to create that, goTIELESS, and why that brand? What did you decide to do that?

    Rob: We're buying all these shirts, we're selling them, what we're paying wholesale to buy a Calvin Klein shirt we can certainly make our own shirts for less and so we originally in 2014 when this was all coming out we did a KICKSTARTER.  We were going to do our own shirt, it wasn't going to be this universal aftermarket upgrade.  KICKSTARTER did not get funded but unequivocally the people who were willing to give us money said why are you trying to compete with all the other brands and why can't I upgrade the shirts I already own?  In 2014 even before the product came out we pivoted because we were going to be a shirt company and it went to Million Dollar Collar the technology. 

    After years and years trying to license this to all these brands and not getting anywhere and hearing the most ridiculous excuses on the planet.  We decided to just make our own shirt with the technology and prove that the technology is enough to differentiate us as a brand.  We tried making them in LA and they just were not that great a shirt.  We did two rounds of shirts that way and then COVID hit and he reset a little bit.  Went to find the #1 best selling dress shirt in America took that as our base model, we upgraded the fabric. 

    So this is a bamboo stretch, wrinkle-resistant, really amazing fabric, that's obviously got Million Dollar Collar.  It also has convertible cuffs so if you want to throw on cufflinks the button holes are there.  We started with three colors we're ordering in a fourth color right now. We've already reordered twice in less than the first year, it's moving along really nice. 

    It was not only to get the attention of other brands but also for manufacturers. I'm making a thousand shirts at a crack. When I'm making 5, or 10 or 20 thousand shirts at a crack, the manufacturer is going to pay attention to that and possibly talk to his customers.  It opens up licensing the technology.  Getting in front of people that I want to sell the product to that will further sell the product down the road.  It's all about getting the technology in front of people.

    George:  I like how you said that and that was going to be my follow up question. Sometimes people struggle with identifying their target audience.  Even though your real target end user audience was the person wearing the shirt you originally went B to B.  You wanted to find those outlets that were going to take it to the individual. You decided I better prove the concept out by going straight to the individuals but you never gave up on trying to also find that niche that would take you there.  What percentage of your business is made up of the original Million Dollar Collar versus the bi products of sending it in we'll do it for you, we have shirts, we have labeled shirts you can use? Is the Million Dollar Collar the concept that pushes all that or is that still the staple of revenue for your company?

    Rob:  It is still a staple. We are in the top .1% of fashion products sold on Amazon and so the website doesn't do a lot of traffic but Amazon we sell tons, it's huge on a daily basis. Million Dollar Collar is my core product.  As a businessman, Million Dollar Collar is a separate silo from goTIELESS, they are separate.   At some point we could grow goTIELESS… My medium term goal is to get to 1000 shirts a day.  If we get to 1000 shirts a day and have a 20 Million Dollar company then we can say if someone wants to take that and blow that up. If you go to our website, it says the Home of Business Casual.  What I want that resource to be is you can go there and say I have an event coming up.  You can get a nice dark pair of jeans, belt, shoes, jacket, and shirt.  You would be able to dress from head to toe with goTIELESS.  This whole lifestyle that you'd be able to do. 

    We're starting with three shirts and then we'll grow that out. We'll still have the Million Dollar Collar technology as licensing.  I should be in Mexico City, Columbia, Brazil, and Shenzhen in the next 6 months talking to different factories.  It's starting to land, there's just so many brands out there you can just grab this and throw it in your shirts and you have those premium versions of your standard shirts.  We've never been trying to say that every shirt should have this, add it to your core business and then people can get an extra 20X or 30X return on their investment by adding Million Dollar Collar.

    George:  I tell you, especially in fashion this all boils down to people wanting to look good, feel good, and make a lot of money.  Let's take a second and I want to go back to, is there a point along the way where you hit some road blocks where you just didn't know it was going to happen?  Or have you had some major setbacks?  I want to highlight to individuals that people get on with guys like you and I and they think it's easy and I'm here to tell you it's not.  It's a grind every day, I don't feel like getting out of bed in the morning, and I don't feel like working out for a lot of days.  Was there a point and time or a particular story of wall that you had to hit or even just a lesson learned from a big failure that you could share with the group?

    Rob:  Yeah, look I got taken for $150,000 within the first 3 years of the company.  We hooked up with... You know I'm getting this brand. I've got to have good PR so I hired these two girls to do PR and they tried to get 12 or 13 or 15 thousand bucks out of us  which I got all back because I paid on credit card so that was pretty easy.  The next company was $4000 a month for 6 months and they got us one article and there was $30K that was gone and then I was able to grow this company organically on Amazon with our influencers and stuff and I hit $20,000 a month within 18 months pretty quick.  Okay I'm doing some revenue I need to go hire somebody. 

    Everyone that we hired to try and plug and play with this product I went from $20K a month to $11K a month. It took me a year and a half to recover from that because I don't know what this Amazon guy did but he totally screwed up everything.  I paid him $1500 in ads and I lost $9,000 a month for the next 18 months.  Those are the days I'm in bed thinking what am I doing with my life.  Fortunately, I have an insanely supportive wife, Linda Kessler, she would be on a high with her career.  She's a badass stunt woman, if you want a whole another conversation we can talk about that.  She'd be on a high and tell me, “take a day to relax, you're doing the right thing” and she was super supportive.

    George:  I think there's lessons to be learned. I think sometimes people listen at the surface and they really don't think through and see the clues in success.  We all want things to happen quick and fast.  We underestimate the long term activities and we overestimate the short term, we really want success so we try to bring it in.  There's nothing like grassroots, hard work, organic growth.  Down the road you're so busy trying to shoot elephants that down the road you are going to wish you had laid the foundation on which.  I know you were constantly doing.

    People need to realize that don't just do all or nothing you have to do all of the above.  I do think you have done a phenomenal job of that and it's a testament of idea and the American Dream and making something out of nothing. 

    Not only is it possible it takes hard work, investment, takes some losses and failures and successes but I also like that you said you have a support network.   Whether you guys just have a partner in life or you have partners, surround yourself with positive people that can give you that uplift.  Let me ask you this, do you have any particular advice that you like to give new or ongoing entrepreneurs especially in the current market place?  Is there anything you would like to leave as a piece of advice for people who are listening to this, listening to you in general?

    Rob:  On those days when you're in bed wondering what you're doing with your life, take a minute to think about why you're doing it? If you're just doing it for money it's easy to just throw in the towel.  In the middle of all of this my wife and I moved to LA, on the way out we got the call that the patent was approved on our 10 day move out to Los Angeles.  We wanted to be in an area that was super vibrant and there's business and connections and all these people.  We're out in LA, we own 2 commercial buildings back in Wisconsin where we are from, we ended up selling those and bought a 50 foot yacht and started a charter business and made a million dollars on that.  Her parents have owned boats her whole life. They said are you guys out of your mind?  Sell real estate to buy a boat!   It turned out because we loved boating, we loved being out there, providing this high level of service.  We had Beyoncé, Pauly Shore and Ron White we had all these celebrities and athletes.  Positioned ourselves like no other boat that was doing charters that we actually grew really quick.  We sold it about a year ago but we had this boat that we couldn't afford otherwise but people... We never went a month without a charter in 4 years.

    It was this incredible thing, we were super passionate about it.  One of the great things that came from that was it forced me away from my desk, if I don't have something I will just bang away on the computer and I am not inspired.  When I was sitting at the helm and I'm just thinking while all these people were having fun.  I would be out of my day to day routine and it allowed me to let my mind wander and that's where I would come up with different ideas and how to market the brand, how to get into these dry cleaners or how to push it into different directions.  This really good side thing came up, not only did we make a bunch of money and have some fun, it helped me grow as a business person because it got me away from my normal routine.

    George:  Yeah, it's another great example of things you are passionate about not just can become opportunities and success but they can also drive your inspiration.  It's hard to be inspired when you're grinding.  It's not hard to be inspired when you're grinding on something you're passionate about.  I find that over and over and that's why my business has always taken me in the direction of fitness and nutrition and investing and things like that.

    A couple of things real quick, you mentioned before we got going here that you could over a discount code to people who are here.  I know they're thinking I want to get some of those, I want to get some shirts.  Give us the website or the best way for them to go check out the products. I want people to do that because I not only think they will affect them not only in the way they feel but also how they perform.  Give us the website and then how can they contact you?  What's the best way for them to get a hold of you or see you?

    Rob:  Actually we're in a little bit of a transition. Million Dollar Collar is our B to B site because we're really leaning in to licensing and getting it in some brands. is our B to C site.  If you go to site use DM15 you'll get 15% off.  By the way the shirts are only $69.99.  I want to hit them at $40-$45 because I want to sell them.  Most of these brands are $125, $175 not everyone can afford that.  My whole thing is I just want to get this on as many people as possible.  A billion shirts a year are sold in the U.S. a year I've always known I have a huge market so with my technology or just getting into the dress shirt game.

    George:  Guys I've checked them out.  They're not designed to be inexpensive shirts, he just wants to hit that price point.  They are high quality, high looking, I definitely would recommend it.  I plan on taking advantage and getting some as well. Rob now I know why you go by Captain Rob Kessler because you're also a charter boat pilot, captain.  Where are you on social media?  Where is the best place for people to find you?

    Rob:  Probably LinkedIn I don't really... I watch social media but I don’t really post. My Instagram has no activity…

    George:  I'll put a link in the shoe notes to your LinkedIn and the website as well.  I really appreciate having you on. I know we're going to be doing some follow ups.  Stay tuned because there is some stuff we're going to tie him into with CEO magazine and Inspire Tours and our Academy.  More to come on that but once again thank you so much for being here.

    Rob:  Absolutely, I appreciate it, it's been a lot of fun.  You guys have a staff you want to look good without a tie. We have great bulk pricing too!