Ep.43- Robert Kessler: Stop Doing It The Way It's Always Been Done

This is the You Winning Life Podcast, your number one source for mastering a positive existence.

Each episode, we'll be interviewing exceptional people, giving you empowering insights, and guiding you to extraordinary outcomes.

Learn from specialists in the worlds of integrative and natural wellness, spirituality, psychology, and entrepreneurship so you too can be winning life. Now here's your host, licensed marriage and family therapist, certified neuro-emotional technique practitioner, practitioner and certified entrepreneur coach, Jason Wasser.

Hey everybody, welcome back to the You Winning Life podcast. Today I'm with Rob Kessler. He's the inventor and co-founder of the Million Dollar Collar, which is a relatively simple solution to fix what he has dubbed placitis, placatitis, excuse me, which is the sinking, wrinkling, and folding of the placket of a casually worn shirt, right? We all see this. I see it all the time on TV, like these million-dollar suits, like on the show Suits, and like they're like folded over and like things aren't staying. But before that, before he built this million-dollar business. He had a screen printing company, an embroidery company that he started out of his home, built to a million dollars in revenue before selling it, and now he has his hands in a bunch of other things including diamonds and the real estate market and auto sales. You're also a captain at this point, right?

Yes, yep.

Yeah, so he's got, right, he's got this thing going on with boating. So Rob, first of all, thank you so much for joining us. I'm really excited to be spending this time with you.

Yeah, absolutely. Me too. Love talking to you, Jason.

Thank you, thank you. So, before we get into all of the little strategies, I would love for people to kind of get a little bit of your backstory, who you are, where you come from, and how did you decide that like this world of entrepreneurship was kind of like your calling?

Okay, so I was born in Detroit, Michigan. My mom and dad left really early when I was, I was maybe 1 when we decided to leave. Dad decided that he just didn't like where his life was going in Detroit and needed to totally reset. So he started driving and found an uncle in Milwaukee, Wisconsin, and just kind of hunkered down there. And he was looking for a job and looking for a job, couldn't find one. Finally walked into a jewelry store and said, "Give me 30 days. If you don't love me, I'll walk away." And after 30 days, the guy fired his brother-in-law and hired my dad full-time. He knew nothing about diamonds, nothing about jewelry. I mean, his first customer was like, "Let me see this ruby." ruby, and he pulled out an emerald. Let me see the ruby. Here's a sapphire. Like, no, the red one, dummy. But he just knew how to work with people and relationships and ended up leaving that store after 10 months and opening his own store. And 40 years later, he just retired. And it was 7 locations and I don't know, 150-some employees. So pretty amazing empire that he built. And so, grew up in Milwaukee, Wisconsin. I worked with him at the later years of my college and then after the real estate crash in '08 when I was in real estate, he had a longtime employee that was retiring. So he said, "Hey, you know what? Your industry's down. I got a position to fill." So I came back and worked for a couple more years and then went off on my own. I had my own screen printing business, was going. I was doing that in the basement after my full day of working at the jewelry store. I think we were so similar that we just butt heads a lot because he could see the younger version of himself in me, I think, which probably frustrated the hell out of him. So yeah, I went and did the screen printing business for another couple years out of my basement, and then I met my wife who was in corporate America. Well, not really corporate America, but she was more of a corporate job. She's really into fitness, so she started doing fitness stuff on the side. And after about a year and a half together, we decided that she was gonna quit that big-time job. We bought a big 6,000-square-foot building. She opened a gym. I moved my screen printing business out of the basement finally. And we rocked and rolled. So we did that for a few years. And then about 5 years ago, we sold everything we had, the business, everything, and moved out to California and started over.

Wow, so multiple things going on there that I want to kind of pick apart.

I didn't get to the cars that I sold. I didn't get too much into the real estate.

So one of the things I love off the bat is like you're the creativity of the dabbler, the creativity of the person who takes all these risks in different areas. And I'm a big fan, right? I'm a marriage and family therapist, and I'm actually third-generation family business owner that I didn't go into the family business. So, but now I work with my family business as a consultant and a coach on the outside instead of being there on the nitty-gritty day-to-day like I would with other businesses. So there's a lot I would love to pick apart about that, right? So you were already doing this stuff in high school. You were kind of led into this path in a way that informed a lot of your future decisions. When did you know that business is for me? I find that people kind of have their calling in a way, and there's sometimes that intergenerational pressure. Of like, I'm just gonna go into the family business versus like, how did you know that this was like your thing and like you wanted it, whether it was diamonds or real estate or silk printing? Because I know the backstory that you didn't share is that you were trying to get something printed and you couldn't find a good enough deal, so you ended up doing it yourself.

Yeah, you know, I always, from a young age, I learned, you know, if you can't afford to pay someone to do it, you better learn how to do it yourself. And I think I was kind of a terror too, so I would break shit around the house. And so I would have to go back and like fix it before I got in trouble. So I learned how to like tinker and fix things. I got really, really lucky in high school. I got hired at a little soccer and volleyball store. And from day one, I was given all of the confidence, all of the support. And so, I, from that moment that I walked in, I felt like a business owner. I mean, I'm 17 years old and this guy's like, here's the key to the store, here's the combination. Find your place. And within a couple of years, I ended up doing the bookkeeping and some of the marketing stuff. Every 8 or 9 months, I'd get an itch and I would go in at 8 o'clock after the store closed, pull everything off the walls, repaint, reorganize the whole store with some friends over when you had all the energy in the world until 4 or 5 in the morning, sleep for a couple hours and get up and go back to school. So I got that feeling that it was my business, even though I was 17 years old, 18 years old. I've got my dad who's been in business for himself. I have aunts and uncles that all have successful businesses. So it just kind of felt like the right thing. When I went back to work for my dad in like 2008, 2009, 2010, we finally kind of decided that our personal relationship was more important than me being an employee. So I knew for sure at that point that I couldn't work for anybody else, but I had a pretty good inkling that that wasn't a good fit. And actually now my dad is, uh, involved in two of my companies. He's an investor and, uh, on the day-to-day stuff. So, uh, it's really cool that we've come full circle and now that it's not his baby and it's my baby, I think the dynamic changed a little bit. So that helps.

Yeah. I want to, I want to go back for a moment because you know, there's something that's already standing out to me about what you said, which is I took this extra effort, I took this extra initiative, I took these extra steps to go and do these things, to paint, to decide I want to go do bookkeeping, right? That you found your place, but the person who was running the business allowed you permission to do that.

Yeah, it was amazing.

Right? First of all, mad props to that person, right? Because usually it's the Colonel's secret recipe and I'm not going to share it with anybody and it's mine and you just work for me and I'm not going to trust you and I'm not going to empower you because God forbid you can learn the secrets and then move on and do your own thing. But that's like, I think, the beauty about true entrepreneurship. Is that if you empower— and a true leader is empowering and finding the tools and the skills in the person in front of you and helping raise them up, right? Raising a leader. So, I'm a big, big fan of that. So, it's really cool that you had that experience. Do you think if you didn't have that, you would be where you are now? I mean, I know, like you said, from your dad's inspiration and the stuff you're doing with your family, but what credit do you give to that type of experience mentally or psychologically about empowering yourself to learn new trades or new tricks or new tools or new skills that maybe you wouldn't have gotten?

You know, it's always hard to know how life would have been without, but, you know, I always go back to that story, so it had to have a huge impact on my life. I mean, you know, I did like, you know, I'm from Milwaukee, so we have Summerfest, so big huge music festival, and then that— those grounds are used. So I would serve pizza, you know, that was like the 16-year-old job. But when I'm 16 and I'm a soccer player and I work at a soccer store and I'm making $8 an hour and I've given my heart and soul to it. When I ended up going to college, my first 2 years, I would go to work in the morning for like 2 hours, drive over to class, go to like a class or 2, go back to work for maybe 2 or 3 hours, go back to another class or 2, and then go back to work and close the store. And there was nothing more than I just wanted to do it. It didn't matter. I almost quit college after 2 years because I thought, I'm making $14 grand a year, I'm living the high life, you know, partying every night and working all day and going to school and the school is just getting in the way. But I ended up finishing up and being the first person in my family to graduate college. So—

Congrats.

You know, I, yeah, I mean that, so his name was Tim Snyder, he was the owner and he ended up unfortunately dying very, very young and very abruptly. I was actually on the phone with him 20 minutes before it happened. And it just was a pretty brutal time losing him because he was a mentor and a friend, and he gave me all the, all the inspira— all the confidence in the world to be what I wanted to be. So yeah, he— I give him all the credit.

It's such a powerful concept, this idea of mentorship, and I talk about that a lot where, you know, we can look back at different stages in our lives and see in addition to our family, who positively and negatively crafted our success, right?

Yeah, I mean, he was just one of those people. There was like, I think, 600 or 700 people came to his funeral, and he's from small Port Washington, Wisconsin. So he was just one of those people that you met him, he made you feel like you're amazing, and, uh, you just never forgot him. You know, he had nicknames, he knew people everywhere, and he just was the most genuine guy. What's really funny though is he ended up leaving, selling that company to his partner, the soccer volleyball store, and going to work for my dad. My dad was mentoring him. So he left to go work for my dad. And when he left, he said, when he came to work for my dad, he did almost the same thing that my dad did. He said, "I don't care what you do. I don't care if you even pay me, but I'm coming to work for you. And at some point you'll find a position for me." And He ended up becoming like this liaison between all the salespeople and trying to get them to the next level and literally created a position for himself within my dad's company. And my dad looked at me one day and said, "He is going to be the next guy to take over this company. He is the epitome of what you need." And I always just try to follow his lead and do what I could for him.

Yeah. So do you believe based on your experiences that like business ownership, successful business ownership or successful entrepreneurship ownership is either in someone's DNA or it can be something that's completely like learned from scratch or somewhere in the middle? Like, what would be your theory?

I think a lot of people, you know, want to do it and some people do it to a decent level, but I think there's a misconception of what you need to be to be an owner. You know, you always see that image of the boss versus a leader and the leaders are the ones that build those monster companies that have, A bunch of high school and college kids working until 3:00 in the morning because they want to for $8 an hour, that's a leader. The leaders are the ones that really separate themselves and their companies. I think as an entrepreneur, that's one of the hardest things to do, like you said before, is turning over those reins and putting your faith into somebody. You think that you can do it the best, but I've got a bunch of people that— think about a great electrician or a great plumber. They're terrible business people. They're like, "Oh, I'm just gonna go do it on my own." It's like, "I'll be there at noon," and then they show up at 3 o'clock the next day. It's like, you're a great plumber and all, but you need to get somebody to do your business side. So, it's not for everybody.

Exactly. Well, that's why I'm a big fan of the E-Myth paradigm, right? The entrepreneur, manager, technician, and knowing what your skill set is, and being honest with yourself, right? A lot of, my introduction to the entrepreneur world has really only been like full-on entrepreneurship has only been like the last 3 years. And I've done all these different conferences and I've done the Tony Robbins and the Grant Cardone stuff. I see your 10X flag in the back, right? Uh, Grant's like, you know, from where I, where I grew up, his office is like 4 minutes away from where I grew up. Um, his now office, not his former California office.

Yeah, right.

Um, so, and I have friends who are very close to them. I know people who've worked for them, right? But you know, but you see the people in some of those circles and we're like, oh, they're just trying— there's no relationship. Relationship with a lot of these things. I feel like you just defined the epitome of a beautiful entrepreneur leadership-based relationship that is not only being successful as a business, but is also successful around crafting people. It sounds like that's what you really benefited and have mastered.

Yeah. I can't remember what book it was. It might have been Good to Great, but he talks about all the people on the bus and just, you know, you may have the a great person, they just may be in the wrong seat. And, um, yeah, finding people's talents and letting them explore where their passion is— I mean, you're going to get so much more out of somebody if they can do what they actually want to do instead of forcing them to do something, right? So yeah, I mean, Tony Robbins, Grant. Um, my dad actually was about 11 years into his business and ready to hand it over because it wasn't growing at all, and he went to see Tony Robbins and it changed his whole life. I mean, he went— he grew Double digits, like 50% a year for 10 straight years. I mean, it was just game-changing. I think he was in that turmoil where he didn't know what he was going to do. He literally was— went to the competitor down the street, was going to hand him the pink slip to the business because he was so frustrated and hadn't grown it at all. Tony got him to think outside the box and think about how to look at things differently. He was in that turmoil, so it really resonated with him. My dad sent me to Tony as well, so I did the Walk of Fire, but it was a college present. I was working for my dad. I was just about to leave Milwaukee to move and open up a store for him. I'm 22, 23 years old, making a pretty good living, $40,000 or $50,000 a year selling in my family business. I had 2 cars and a motorcycle. I'm like, I have no turmoil. He didn't really resonate at that time. But I go back and when, like even right now, I mean, I go back and I'm reading Unlimited Power and Awaken the Giant. I'm just rereading and—

The classics.

Getting that stuff back in. And I think those are good resources to go to even if you can't have a conversation. So my dream in life is to be able to get my dad and Tony in a room because there's not a lot I can give my dad at this point. He can get whatever he wants, but to get him back to the guy that changed his entire life and my life and my brother's life and my sister's lives, um, I mean, it would be the best gift in the world.

So, well, it sounds like with Artie, your creative mind, that you're definitely gonna find a way. Because sometimes it has to do just with the ask of who knows, right? Putting it out to your social network. Who, right, who knows who's got an immediate connection with Tony that can pull this off for 15 minutes from, you know, help me pull this off for 15 minutes?

I got a couple people. I'm just like easing my way into it. So be bold, my man.

Man, people. I did that for Howard Behar from Starbucks. I saw his book, It's Not About the Coffee, and he's the former international president under Howard Schultz. I just literally took a blind shot and directly emailed him and mentioned some people that I'm friendly with from that business entrepreneur world that I know he's connected to. Within 15 minutes, I got a response back saying, "Yeah, I'd love to be on your podcast." This is the guy who literally brought Frappuccinos to the market. And built every single store outside of North America. And he was the North American— you know, retired as the North American president of Starbucks. But like, this is like, you know, the second in charge of, you know, under Howard Schultz. And it was amazing. And it was just like, all I had to do was ask, right? So I don't know, I'm just getting— we're just becoming friends, but like, I'm gonna, I'm gonna challenge you. I'm like, I'm gonna hold you accountable to making this happen for your dad.

I'm gonna work on it. Good.

So let's take it a little bit forward, which is going back into your— you seem like a guy who finds, who sees a problem, and then if no one else is doing it, like you said, you're gonna go do it yourself. And this shirt thing, this Guy's Dress Shirt Placketitis thing, first of all, great branding, great marketing, because, right, what the heck, like thousands of prototypes, Lots of money spent, right? In a way, it's kind of like the Sarah Blakely style of doing, right? Because it's a very similar, right?

Yeah. Story. I'll be compared to her any day. I'll take that.

And yeah, right. And I'm in Jessie's, um, her husband's Build Your Life Resume community, and that's an amazing, amazing community of people who are doing some incredible stuff. Um, why didn't you give up? Like, after, after shirt 1,000 or 2,000, like, like after this amount of time, like, what made you not stop?

Well, I'm one of those bullheaded, annoying people that I think once I get a goal in my head and that I'm gonna do something, I'll get focused on doing that. I mean, we have a— I have a 5,000-piece puzzle of the New York skyline pre-9/11 hanging on the wall, and people always see it and they're like, oh my god, that's a puzzle! But it was like, I was determined to do it. And so I— and, you know, all that blue piece after piece after piece, it's blue. And now I'm working on a 13,000 1000-piece puzzle of the Sistine Chapel, God's creation of man. But I just— I'm really focused, you know. The idea came up after looking at my wedding photos. I had a brand new freshly pressed shirt on. It was less than 30 minutes after taking off the hanger. It was before I said I do, and it was just a crumbled mess, and I hated the way that it looked. So, uh, after coming home from our Jamaican wedding, I started Google searching. There was nothing out there. Everything was some kind of collar stay or magnetic collar stay or some piece of scaffolding that goes under the—

it just—

that's not the problem. The problem was down in this part of the shirt. And so there was nothing out there. We did a patent search. My wife was insanely supportive from day one, and it wasn't out there. And so I just— that was my goal. I knew I was going to bring this thing to market and do it. So I slowly tested every plastic I could find on the market. I thought I'd have a winner, and then I'd send it to the dry cleaner and Sure enough, it would melt right to the shirt and it's just like, oh God, no. I ruined an awful lot of shirts figuring it out, but thank God I have a lot of friends who wear dress shirts that had been worn out. I just kept testing and testing and testing and been selling for a little over 4 years now. Now we've launched our own dress shirt. We can license the technology, so we're talking to all the big brands to get them to just put it into their shirts. And while they're dragging their feet, not wanting to change the 100-year-old design of a dress shirt, we decided let's just make our own shirt. And that's going, even in these times, which is really crazy, we're selling really, really, really well. So, yeah, I know where I wanna go. It's trying to find the key and unlock the combination. So, the only people that don't make it are the ones that give up.

And it's so applicable to what's going on right now. With this era of the pandemic of pivot and how fast and how quick is each industry going to change. What you said, the 100-year-old way that it's been done no longer exists as of a month ago, a month and a half ago, right? And I had within 24 hours, I had to pivot my whole private practice from being in person to, right, to being online. And as we were talking before this call, where my lease is up in a month and a half. And I'm like, I don't know, do I just like close down my office and go fully online? And what will that allow me to do? And is there a risk of losing people? And when— if things get better in 6 months, are people gonna now be like, well, where's your office? I don't know, right? There's so many different things that we have to pivot to the new rules, which are you get to make up your own rules. And I really do appreciate about what you're saying is that while they're dragging their feet, I'm going to reinvent the game. And I'm going to do something that they're not providing.

Yeah. It's funny, I always hear the feedback, "Well, I don't know if my customer has this problem." Well then, why am I selling my product to your customers if they don't have the problem? Yeah.

Or they don't even know because they didn't even think outside of the box enough for it to be aware of being a problem because we are so stuck in a logical way. We have our sequences in our brain, right, neurologically. You probably know this from the marketing side. We only see things based on the neurological paradigm. We're never going to think and solve a problem or choose something differently outside of that construct.

Well, I think there's that corporate pressure of, "I got to this role. I'm going to fly just under the radar so that I can keep my job and not step outside." Fortunately, we're actually working. We were contacted in October, it's April now, by the company of the dress shirt I was wearing on the day of my wedding. And so who was who we wanted all along, they contacted us. And so we've been negotiating with them, we've been talking, and then all of a sudden all kinds of stuff came up. But I think most people are just afraid to make a change. I think a lot of people in corporate America are, like I said, I think they're stuck in this, I want to keep my job and I don't want to step too far outside the bounds. But you're right, you can't do things the way that they've always been done. I mean, the biggest company PVH, who has Calvin Klein and Van Heusen and all these. They came out while I'm coming out with a technology for the 90% of dress shirts that are worn without a tie. They came out with a stretch collar. Great, nobody's wearing a tie, who cares how much— why do you need a stretch collar when nobody's wearing a tie? But you're not buttoning it all the way up anyway, right? So, you know, I look at them as the oil tanker that, you know, or the Titanic that needs to take a long time to turn, where we can pivot. And so You mentioned pivoting, and we've probably pivoted the company 4 or 5 times already just because, you know, that's where the customer's feedback is. We did a Kickstarter in 2014 before we even launched the company, and we didn't get funded, but people unequivocally said, "Why are you trying to make your own shirt?" We were going to do our own shirt at that point. They said, "Why not license the technology, and why can't I upgrade the shirts I already own?" And we're like, "Oh my God, yeah, you already know." what fits, what fabric you like, why not make it? So, the whole design changed when I thought I had it. It all changed and I had to come up with a universal design that fits into every single shirt, which is what we have now. So, you have to be able to listen. I think there's a lot of entrepreneurs, if you watch Shark Tank, you'll see these guys get so stubborn and like, "No, no, no, this is the way we're gonna do it." And it's like, that's not what the market's telling you, that's not what the numbers are telling you. You have to listen.

Or the experts are telling them, right? And I love seeing that they'll the 4% more. Can you do 5% less for $20,000? Like, you're making— if you're making, right, zero of zero— 50% of something is always better than 0% of nothing.

Yep.

Right? And again, I think—

yeah, you know, we've talked about Shark Tank and these things, and then, you know, we can— we get investor, uh, reach out a lot on both of our companies. And, you know, obviously we'd love to be on Shark Tank for the exposure and, and working with one of those guys that has the connections. But, you know, we keep talking about having, you know, 50% of a grape or, you know, 10% of a watermelon. So it's a lot different, you know, thought process of where you can go with some cash and some connections.

It's a long thing and it's a big difference. And I know that like this is the mentality that like one of my mentors, one of my coaches, Rick Sappiau, is a billionaire capital venture capitalist. And his whole first primary starting point is the fire, so to speak, kill Superman, Superwoman, right? You think you're going to do it alone. If you're not going to hire the right experts, if you're not going to consult with the right experts, if you don't find the right accountants and the right attorneys and the right business people and the right marketing people, you can't do it right. You're never going to grow to the potential success that— For me, it's a little bit different, right, because I have associates that are working under me. I have another therapist and a chiropractor. And a nutritionist, but I still have to empower them to get the right clients and have to help them market and stuff like that. But once they're seeing a client, it's money that's coming into my pocket without having to do anything. And my job is, if it was a different rate previous to the pandemic, it was just how can I get that to scale with how many people, right? But at the end of the day, I still have to see a client in order for my money to come in at the higher value. And there's a way that I have to figure out, like, as a business owner, Well, I would rather be working with 5 people like you on retainer for the course of the year than seeing 30 people a week and basically make the same equivalency of what that is, especially when it's a higher value for me as well, right? It's much more enjoyable. So, like, this is a time for everybody in business to, like, really think about, like, who have I always really been wanting to serve and what are the problems I really want to help solve? Not because the economy forced me into doing X, Y, and Z and I had to settle there. Or I'm afraid of making a riff because I want to keep my job.

Yeah, you know, and I love what Grant says. Grant Cardone's big on, you know, the rich people are good at buying time. And so for every person that you have under you that can do, and if you can accept, you have to accept 70% or 65% of what you can put out. If you can accept that, you can create time. And that's the one thing that money can't buy. You know, so finding the right team and getting them in place, it's funny because, you know, like I said, I, I, if I couldn't afford someone to do it, I had to learn how to do it myself. But you can only do so many skills. And while we're trying to scale this business, fortunately I have a business partner that is the opposite of me and is really good at a lot of the technical and the graphic stuff. But even at that, it's like, look, we need to hire people that know the email follow-up system inside and out so they can build that and we don't lose people out of the system. It's time to get those pieces in place so that we can really start to create time because you get a good email follow-up system, that's like having another employee. So spend $5,000 or $10,000, get it dialed in and not think about it again. What do you think about that, Rick?

Because for a lot of people, it's kind of like, I can put that money in my pocket so I can pay my bills. It's the short-term versus long-term, right? That people were very short-sighted. Yes, obviously people have to pay their bills, but where did you find for you where it's kind of like, okay, I'm going to sacrifice a little bit more of income in order to bring this person onto my team?

I think I listened to enough people that said that you have to sacrifice. I like Gary Vee as well, but I always knew that it was going to take sacrifice. I think I learned a lot originally from my dad. He would be the last one to get paid. And while he's building this business, we ate a lot of beanies and weenies, as he called it, because you know that there's, in the long term, it's gonna work out. I often tell my wife, and it's, I have a much bigger goal for life than most people, so it sounds crazy, but I say, I'm not doing this so that you can plan a trip with your friends in 6 months and say, all right, we're gonna do this. I'm doing this so you can call a girlfriend, 3 girlfriends and say, "We're leaving right now. Pack your stuff. We're going and I've taken care of it. Let's go have a good time." That's what I'm working for. That, to me, requires a different level of sacrifice than, "I want to go put a Porsche in my driveway. I can make 2 grand a month to make that car payment. That's easy." But the life that I want to build, that her and I both want to build, takes a lot more and a lot more sacrifice. Jason Wasser: Thinking on the long term of it, I mean, I'm 7 years in, so I'm maybe 3 years away from my overnight success, you know? So yeah, right.

And it is, right, it is that 10, 20, 30, 40-year overnight success.

And I mean, yeah, I mean, it's, it's a long-term, long-term goal. And so putting myself in the back seat for a little bit while we make it, you know, while we get by, then that's what it has to be. I mean, look at this, is my home office, which is also the shipping center, which is also the sewing center. That's respectable, right?

It's It's the idea of you do have— because I see this all the time. And as I referenced before, I grew up in South Florida and my own— I was a scholarship kid and I wasn't a great student, but I grew up around kids who were at 16 years old getting Range Rovers for their first car. And I'm like, oh my God, I had a rabbi pay for me to go to private school, to go to a Jewish local private school because the public school I went to wasn't really good at all. I went to a magnet program in an inner city school and I had to leave that program. So I was the scholarship kid. In the middle class, right, in an upper middle class scenario. And I just saw my relationship to money was all around, if you have a lot of it, you're a dick, right? And you're from the Midwest, so you have a— right, so Midwest is a very different mentality. Like the people— and I know that because I was born in Scranton, Pennsylvania, and I know like there's people there who are incredibly wealthy, but they're driving a Toyota Camry.

Jason Wasser: Yeah. Milwaukee is super conservative. There's no Ferrari dealerships in Milwaukee. There's no Lambo dealerships, but there is a lot of money. I ended up in high school in Shorewood, Wisconsin, which is on the east side, right on Lake Michigan. I had friends that live in what today are $5 million mansions on the lake that, yeah, they were driving all those cars. Nicolet High School is right there and Whitefish Bay High School. I knew kids with Porsche Hummers and it was my mom and my sister and I in a 2-bedroom duplex. My parents were divorced and so I went to live with my mom and my sister. My sister and I shared a bedroom. We're 5 years apart and I'm in high school. It was weird seeing it up close like that, but I think it gives you perspective. I mean, I live in LA now. The abundance that is here, it's either going to inspire you or it's going to crush you. And to me, it inspires me. When I see a McLaren or a Lambo or something, I'm like, yep, that's cool. They're doing it.

They're doing it.

They've got it already. So I'm a little bit jealous and I'm a little bit irritated that I don't have it yet, but I know I'll get there. And I just love it. I love being around it. And as long as you don't let it consume you, I think you can let it fuel you, and it can be a good thing.

I truly believe that the entrepreneurship process, as a therapist, is a, is a path to self-awareness and personal development. And right now, I'm not just talking about like the Tony Robbins stuff, like, because it's not necessarily always about business with Tony, or, you know, and Grant is— Grant is an interesting mix of stuff, and he was one of the first people I got turned on to. When I started down this road a bunch of years ago. But I really do, like, psychologically, like, when you're talking about LA, for example, I remember the first time I went out to LA, um, it was the second time I was out there for a wedding, for a friend's wedding, but I was, that was in the Valley, so very different vibe than actually being in the city, being in, in Hollywood Hills and staying literally up at someone's house in the Hollywood, you know, literally right under the Hollywood sign. Um, and then coming home one day when I was out traveling and sightseeing that the cast of Jag was over for dinner if you remember that show, right? Oh yeah, because they were produced— the person's house I was staying at was a producer in Hollywood. Um, and walking around realizing like, I don't think I'm good-looking enough to be in the city. That was my mentality at 24 years old, like, I'm not good-looking enough. Forget about the money, I'm not good-looking enough to be here in the city. And then now going back multiple times over many years to see other friends and whatever, I'm like, okay, I get it now. Like, I see it through a very different lens. But I think a lot of that came from me realizing my value as a therapist and as a business coach and as an alternative medicine practitioner and as a speaker, that the value doesn't always equate to that house or that car, but what can I bring to help someone else? What problems am I helping solve? Right? And a lot of your businesses have been about solving a problem. But I also realized that, like, I've become a healthier human being because of this journey.

Yeah, I mean, you know, you said before, I think, the people around you that had money were dicks. And it's like, I think that I've seen the money brings out who you really are. I mean, if you're a good person at your soul, you know, you're going to be a good person with $10,000 in the bank or $10 million in the bank. And it's funny watching— I've seen people go through this arc and it's like, you know, from $0 to $100,000, they're still them. And all of a sudden they hit like $200,000, $250,000, $500,000, and they get this ego like this, like they are just the best thing ever. And then once they get past that, like half a million dollars a year, kind of like, okay, well, now they start hanging out with people that have are bigger than them, and then they're like, gets maybe put back in their place a little bit. Then, you know, I even watched it through my dad went through that phase, and it was just like, okay, well, you know. But then he hit this other cycle, and it was just like, man, he's just the most chill, you know. A bunch of kids, he's got 7 grandkids now, and it's like, you know what, if something breaks, it breaks. It's just stuff, we can always replace it. But when I was as those kids' age, yeah, hell or high water, if something broke, you're deep, deep trouble. That's the journey, right?

That's the unpackaging of it all. And I, um, I've spent time with Dr. Ivan Misner, who's the founder of BNI, the networking— the international networking group, um, over the last couple years, um, and I've had some really nice one-on-one conversations with him. But I remember like when I saw him, um, when I saw him a few months ago, um, at my business program in Dallas, um, he said that he has been invited to Richard Branson's private island, uh, Necker Island, multiple times, right? And he's like me? Like, who the hell am I? Like, just like, you know, like, he, he knows me and he spent time with my son and he asked me questions. And then we went on this other private tour of another island he's buying. And like, he like, I was one of the 5 people, like me. And I'm like, this is Dr. Meisner. Like, if like anywhere in America you go, someone's going to try to get you to come to a BNI networking group, right? That's like a thing. And it's a great program. And it's a brilliant thing. And he, the guy is one of the nicest gentleman I've ever met and great storyteller. But even him, who has over a million members in his business all over the world, he'll still be like, "You see value in me?" Yeah, I mean, it's—

I think being humble is a much better way to go. And yeah, you can, you know, you can pick who you associate yourself with, so.

You have to proactively choose. And I'm a big fan, and the people who know me pretty well, especially when I'm giving my workshops and classes, I'm like, "You're always going to hear me go back to one thing: core values, core values, core values, core values." And if you tell me your core values, I'll tell you what you should be expecting in your life. And if you're not living by that, then I can tell you why all your chaos is in your life. So whether you're a couple, you're an individual, you're a young professional, you're one of my businesses that I'm coaching, I can't help you unless I know your core values. And I can tell you why you're out of alignment, because you're probably either A, not aware of them, or you're not living in alignment with them. So, that's where we need to do the work first. And bringing that into the next few minutes that we have together, I'm really curious about the dynamics of a husband and wife entrepreneur dynamic. And I know you guys own one business together, and I know there's multiple things that are going on that she's involved with and you're involved with, and there is some overlap. What has been some of the pros and what have been some of the cons of being husband and wife, both being entrepreneurs in your own right, but also bringing that home and maybe even, you know, on the business that you collaborate on together?

It's been funny. You know, I got into real estate when I was like 23 years old, maybe, and I would see these husband and wife couple teams, and I looked at that, I was like, What? You work all day together, you wake up in the morning together, you have lunch together, you go to bed together, you eat dinner, like what? And when I met my wife, we clicked unbelievably from minute one. And once we bought that building, we literally— her gym was on one side, my screen printing business on the other, and there was an office that divided them. And we sat 10 feet apart and did that for 3 years. And it was amazing. I mean, in those 3 years, we probably did 10 years worth of, you know, a normal couple's relationship. And, you know, there's definitely hard times of, you know, she has ideas or I have ideas and communication sometimes breaks down. But at the end of the day, you know, I know I've got someone that's got my back. She knows that she's got someone that's got her back. We've been able to work things out. We have a boat business together. We have a yacht charter business. So I'm a 50-ton master captain, which I've gotten since we've been here in LA. And, you know, I, I'm like the— I, you know, I captain and I kind of oversee the stuff, but she is so detail-oriented. So it's really a good balance between she takes care of the stuff that I don't like to do and I take care of the stuff that that she doesn't do. So, you know, when she's not doing that, she's a Hollywood stuntwoman and she's incredible and a super badass. And, you know, we just try to make the most of what we have. But, you know, when you spend this much time together, there's always gonna be, you know, headbutting and problems. So it's, I heard something and I'm not the best at working at it, but I'm working towards it. Somebody once said to me, if it won't matter in 5 years, don't waste 5 minutes. And, you know, when you're in the heat of a battle over something stupid, you know, sometimes it's hard to think about that. But if you can keep that in the back of your head when things are going down and just get over stuff quicker, it'll make all the difference in the world.

100%. It's so funny because I had my last call, uh, my last session before you and I jumped on this call was about those dynamics in a couple that's a family business and the amount of time, effort, and energy they're spending on things that are completely superfluous. And not only superfluous, but they don't have any control over. And I'm like, how is that building your— A, your relationship, and B, putting dollars in your bank account by spending time on what's going on in the world? And like, but, but, but, but, you know, but I gotta, but I gotta put my voice out there. Is that putting those— you came to me for two things, help your relationship, help your business. Is that towards it or against it, right? Simple. And how much time, effort, and energy have you put into whatever that issue is that you could have then, right, over the last week, how many hours? Oh, whatever, half hour, an hour, two hours. Okay. So that two hours towards your business, what would that have done for you? It's really just a simple pivot when you get, you know, our brain goes into that fight or flight when we get to when our heart rate goes up on something. We're automatically in reptilian brain, which is fight or flight, which is that old self-sabotage, what we would call self-sabotage intellectually or psychologically. And you can't solve a problem from that place. No. Right? And so our job, right, you as a business owner and working with your wife, and my job as a therapist and a coach is, right, how do we strategically, proactively, because we're all in a fight or flight right now with what's going on in the world.

Jason Wasser: Oh, yeah. I think it was Seven Habits of Highly Effective People, but it's the stuff you can control and the stuff you can't. That really, really resonated with me. My mom worries about stuff that she can't control sometimes. You always have people around you that do. To me, it's become an obvious observation. It's like, look, you can't do anything about it, so what can you do? Where can you spend your energy? But when you're in that mode and you think it's happening to you, it's hard to take a step back and say, "Look, I can't control that, but I can control this." And I don't know, maybe being a problem solver, that comes a little bit easier to me. But yeah, you just can't spend— it's so exhausting to spend energy on stuff you can't do anything about. Yeah.

Where does self-care come in for you and for her on this? What's that process as? You're running multiple businesses, you're a married couple. You have other stuff going on. What's the process and journey of self-care for you guys that's been working?

We do therapy. I think I relate it to having a coach or a mentor in business. She's been riding horses since she's 8 years old and she still rides. She rides 2 days a week and she has a trainer. So, it's like, "Look, you've been riding for your whole life basically and you still have a trainer because you want to constantly improve." And like you just said, sometimes you can't see what's right in front of your face. And so recently, we had our therapist said, "What did you do early on that you guys don't do anymore?" And I was like, "You know what? When we lived in Milwaukee, we had a huge kitchen in our little duplex. It was just like an open kitchen." And so we made dinner together like every night. And when we moved to LA and paid like 5 times more than we were paying in our mortgage It had a teeny tiny kitchen, we couldn't both fit in it. And so for 4 years, we didn't make dinner together. And so all of a sudden, she's like, "Well, do that. You go shop, you guys decide together, you go shop, and then you make it together." And so we started doing that. And it's like stuff that is outside of— both being entrepreneurs, we always want to talk about business. What happened in my business? What's happening here? What's going on here? And in that sense, It's so not emotional. So for us making dinner together and we start reminiscing about when we met and trips we've taken and things we've done, it's just kind of changed the foundation and helped rebuild that. And that's been awesome.

So it's become a date night of sorts. Yeah.

I mean, we can't go out anyway. So, you know, we typically, you know, make dinner at home because, you know, we moved to LA thinking that, knowing that there was opportunity here. And so— Coming from Milwaukee and we sold my business and our house and everything we had, we knew we had to kind of take it easy because if you leave the house out here, you're spending $150 or $200 real quick, especially for the couple. So we just don't do that. And it's another thing that we sacrifice because we want to get to a further point. So it's better for us to have the cash in the bank. We make dinner. Then we can meet people out. But yeah, I mean, making dinner is— it's been great. It's been like a little date thing, and it's cool. You just gotta do what you can do with what you can do.

So is there one thing that if you can maybe like sum it up— and I kind of call this like my On One Foot moment— of if you can distill everything down in a shareable kind of like if the people out there can do this, or if they learn this, or they apply this in their life, this will make things so much radically easier and more meaningful or more successful for them that you feel like really is like the distillation of everything to this point that you've accomplished?

Yeah, I mean, know where you're going. That certainly helps. I mean, begin with the end in mind, as Stephen Covey says. If you don't know where you're going, any path will get you there. My wife and I really hit on when we first met of what we wanted out of life. Coming from super conservative Wisconsin, she's from Green Bay, even smaller than Milwaukee, we knew we wanted to do stuff that the people around us weren't really talking about. We connected on that level. And when we're battling over dumb stuff, it's because we've forgotten where we're going. And so when we can divert back to, look, this is what we want to do, this is where we want to go, we want to travel, we want to do this, that, whatever. I think knowing where you're going is certainly a guiding light, I think.

Yeah, and having those conversations and not being afraid to have those conversations.

It's not always easy.

No, right? But, but I think— but that's like in the business mindset, like we have to have these conversations or something's going to fall through the cracks, and we don't want that to happen on that, right, on the financial side. But it's also interesting that people don't apply that. Also, it sounds like you guys are applying it, which is really cool, but a lot of people out there that I— that's why they end up in my office is because they don't have these conversations that you and your wife have been having. So I think that's really cool that the process that you have been doing in the self-care and the keep going and keep going and keep going and test segments. And I think it's amazing. I think it's amazing. So I really want to congratulate you and she on the successes that you guys are having.

Thank you. Yeah, well, you know, every day is a choice. You know, I wake up every morning, she wakes up every morning and said, "We're going to be married. We're going to figure out today and, you know, we'll do it again tomorrow." And that's how you get to, you know, be married for 50 years or 70 years. It's funny because she comes from, Her parents have been together for 40 or 45 years. My dad is twice divorced. My mom is divorced and remarried. She's seen that side and I've seen this side, and I don't ever want to get divorced. She's like, "Well, I don't really know what— I don't deal with that either." It's cool that we're on the same page as far as that, which means there isn't an out, there isn't an easy You go your way, I'll go my way. Let's break it down and figure out, you know, we got here, so let's get back to where we came from and, you know, get back on track of where we're going.

Yeah. So in other words, keep it simple, stick to the basics. Do lots of cooking.

Yes, I love that. Keep it simple, stupid.

Yeah, keep it simple, stupid, right? And do lots of cooking together. Do as many activities. Share. It is. It's the like. When you do business with someone, you're trying to do business with like-minded people who are trying to accomplish like-minded things, and that really does have to apply to your personal relationships as well, especially your most intimate relationships.

Yeah, absolutely.

So if people want to track you down, where can they find you? How can they reach out to you? I know you've been on a bunch of different podcasts and you're doing some really cool stuff, but what's the best way for people to, one, track you down if they have questions or they want to get involved in the business or become, you know, whatever it may be from the business side um, but also like social media and buying the products.

So, uh, I don't tend to do a lot of personal social media. Um, so I have a LinkedIn, I'm on there. My two companies are called Million Dollar Collar, that's the technology that I invented. Uh, and then our shirts are called Go Tieless, the first shirt designed to be worn without a tie, uh, with obviously with Million Dollar Collar already built in. Um, so I'm Rob at Million Dollar Collar or Rob at Go Tieless, uh, are my emails. And we have all the social medias, Go Tieless and Million Dollar Collar. So fairly active on Instagram, a little bit on Facebook for the businesses. And the boat business is Bella Boating. So if you're in LA or you wanna get out on the water and see some dolphins or whatever, we have a great boat for that. And yeah, that's it. My wife's a stuntwoman, so she's a, I guess that she's awesome. That's cool.

Is there anything that we might have seen her in?

She was a Skrull soldier in Captain Marvel, so that was probably the big blockbuster that she did. She doubled Taylor Swift in a music video. That was pretty incredible. We helped Beyoncé with a music video on our boat, so that was pretty insane. I, I love when people come on the boat. I'm like, Beyoncé sat right there. And so Yeah, we've done some cool stuff. She's done— she's had a pretty amazing career for only been in it 3 years. She's worked on, I don't know, 30 or 40 or 50 shows. So she's, she's set a goal and go after it kind of girl, and she, she definitely has epitomized that. She inspires me to, you know, go after and keep going and, you know, get up early and get my day going and, you know, provide her that life that I told her I would.

Beautiful. Well, I appreciate so much the time you've been able to share with us today. I know there was a lot that hopefully people are going to get from, from today's episode. And as always, if anybody has any questions, you have all the ways of reaching out to him to get to buy this product, right? If you're a guy, and even though we're working from home, you know, we still need to show up every once in a while to a meeting and in a really good shirt. So treat yourself to something new and, uh, and, and show up in a way differently than you have for the last 100 years. Like the way the other companies—

Yeah, yeah. If you like wearing dress shirts without a tie, we can upgrade the shirts you already own. So we're in 600 dry cleaners across the US right now. So you just drop your shirts off, have them install it, and costs about $10 a shirt. Once it's installed, it lasts a life and it will prevent the front of the shirt from collapsing. So it's a game changer. Just check out milliondollarcollar.com. And if, uh, We've got some other shirts, Calvin Klein's and Tommy Hilfiger and Kenneth Cole. We have shirts that we've bought that we've upgraded, so we have upgraded versions of those shirts. If you already know those brands, you can grab one of those. Then Go Tieless is cranking. I mean, it's really weird. I think with the lockdown situation, people are turning to e-commerce unlike ever before. I mean, there's a lot of people that have, in the last 60 days, have made their first e-commerce purchase ever. So there's a lot of business on e-commerce and our shirts are selling unbelievably well. So, couple of colors, I mean, we only have 3 colors right now. We just started bootstrapping and just launched that. So it's incredible that we're selling as well as we are with just 3 colors, but we've got another one in production and another 5 or 6 coming in a few months. So yeah, it's been wild.

Awesome. Well, congratulations again on the success and for sure what's going to be, as within, like you said, within the next 3 years to hit that massive goal that you've been doing that long marathon to get to?

We'll see, you know, inch forward every single day. That's it.

You got it. Thanks for listening to the You Winning Life Podcast.

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