Sean Castrina — Founder of The Weekend MBA
28 Jan 2026 · 44 min
Interview (podcast) with Sean Castrina (founder of Weekend MBA, serial entrepreneur) hosted by Bill Gallagher. Sean recounts his entrepreneurial origin (started Waxmaster Mobile Detailing after a corporate job change), explains his repeatable formula for building service businesses (find a high‑demand local problem, make an audacious differentiating promise, partner with skilled operators, scale by adding complementary service divisions), and shares common startup mistakes (confusing passion with market validation, hiring friends/family, hubris). He emphasizes people strategy: always‑be‑interviewing, hiring "unicorn" partners who are leaders, experts and rainmakers, guaranteeing pay or profit share to recruit talent, and simple culture rules ("do the right thing as if it were your house").
Chapters
Are you thinking about how to grow your business with near and offshore staffing, but you're also wanting to make sure that it's reliable, cost effective and really well done? I think docsa talent is the way to go. Here's why. They don't just fill your jobs. They bring integrity, top talent and a people first approach that's hard to find. I've known the people at Doxa talent for over 20 years now and I say that you can count on them. I have talent to Doxa Talent and you won't be disappointed. Go to doxatant.com Bill G. Again, that's doxatant.com Bill g. One more time. Docsatalent.com Bill G. Check it out today. There it is again. Hey everyone, we're live and we're talking today about a couple of things that entrepreneurs forget in their journey. We get distracted by so many things. What are the kind of core things that you need to do, whether you're a startup or as most of our folks are scale ups, Everybody. My name is Bill Gallagher, Scaling Coach, host of the Scaling Up Business podcast. Our show comes to you every week with stories from experts, entrepreneurs and others about all the things that they've learned in growing a company, the secrets to beating the odds and being one of the success stories. All our shows and more now for five years. Hundreds and hundreds of shows now@scalingcoach.com or wherever. You're getting this right now, whether it be YouTube, iTunes, Spotify, etc, Stitcher, Facebook, LinkedIn. We've got it for you. Video and audio every week. Scalingcoach.com all right, so we're joined now by Sean Castrina. Sean Castrina is a podcast host and an all around rock star. He's founder of Weekend mba. He's a serial entrepreneur. He's done a whole bunch of companies and he tries to launch a new venture every year. So he's going to share some of his story with us and some, I think really great essential principles that sometimes we forget in the process of running our businesses and working to grow. Sean, welcome to the show.
That's great to be on the show, Bill. Thank you.
Where are you today?
I'm in Charlottesville, Virginia. Right near University of Virginia. Oh, lovely.
Yeah, we were there nearby there. I was in Charlottesville, what, two, three weeks ago. Wanda at Keswick Hall.
Yes. Yeah, yeah, it's great down there. That's a lovely place.
Yeah. So anyway, I'm, I'm excited to have you on. I think it'd be great if you said to folks a little bit more about your entrepreneurial story. I think you have a great story about working for others, getting a degree, and then seeing that maybe there was a better way for you. Yeah.
Share that. There you go. Okay. So I came out of college. I was Division 1 college athlete and took a job for free wrestling. Division one college. And so I took a job coming out of college to work for free for 90 days. I just figured I'd skip all the rungs on the ladder. So I went to a big organization and said, instead of coming in for, you know, a very low wage, I said, I'll just work for you for free. Fairly confident that I would earn my way there. And I. And I did. You know, the guy I work for actually lives a few miles from me, and. And his son was a business partner of mine. And this is, you know, 30 years later. So had my dream job. I was in graduate school, and the head of the organization ahead of this person that I'm friends with resigned and, you know, retired. And there was a change in leadership. And I remember going into an office and hearing these words. This is where your whole life changes when you hear this. We're going in a different direction. You never want to hear that just for anybody out there. We're going in a different direction. Different direction. Yeah, we're going in a different direction. That is a code for we just gave you the middle finger. So I. Life kind of literally slowed down in that 32nd period there. But I have a strategic mind, and I just kind of figured, okay, all right, well, there is no such thing as job security. I knew that right there, and I just was like, okay, I'll get a job temporarily, but. And I never. Prior to that second, I'd never thought about owning my own company. That's the funny thing. Like, I figured, you know, I'd be a type of person to work my way up the ladder and be a CEO or something like that. I just had that kind of personality. Competitive athlete, you know, I'm just gonna. Okay, here's the top. Here I am. Okay, how do I get there? That's just kind of how my brain. How my brain works. And. And I was fine with that. But then when this happened, you know, I had to go in a different direction and did. I went. Started selling insurance, life insurance. Next to selling drugs, selling insurance is actually really profitable for me. I understand. It's the first time I ever saw, like, really crazy expensive cars and crazy expensive lifestyles in my one year. I. I remember going to lunch with the one guy that I worked with, and he had lost, like, $250,000, like, gambling. And I'm like, like, but he's worth millions. And I'm like, well, gosh, you know, I'm just thinking that, I guess you're so rich, it doesn't matter. He goes, don't ever kid yourself. $250,000 hurts no matter who you are. But it's the first time I really met really crazy wealthy people selling insurance. And I was in a sales meeting, and this is how my entrepreneurship journey happened. And what I'm getting ready to tell you is kind of what's made them last 30 years. So I'm sitting in this sales meeting, and I'm seeing all these really nice cars out in the parking lot. And mine, which was not that nice. It was a long meeting. And I'm like, you know, what if just one of them brain farts if I could get somebody to come to this parking lot and clean my car while I'm in this meeting? Because when I get out of it, I. I really need to go find a car wash and get it cleaned. Yeah. And right there, you know, this idea hits me. What if I could get, like, a van and they could put water in it? Now, this. This is 30 years now, but 30 years ago, that was not. Like, nobody was doing that. And so I started a company called Waxmaster Mobile Detailing. And this is why it's unique. I can care less about car wash, car cleaning a car. I've never cleaned a car since then. I never cleaned a car then. I never cleaned a car since then. It was not a sexy business, wasn't even a business I liked, but it was a business that I knew would make money, I knew would work, because I knew everybody in that sales meeting agreed with me. They'd pay to get their car clean. So I started that company. I did a 50, 50 split. At the end of every week, I create up the marketing I had. You know, when you called, you spoke with a SEC person, and they just lined it up, you know, inside, outside. Do you want both? Is it a, you know, an SUV or is it a car? You know, four different pitches, and I made $30,000 without having to do anything. And I knew then that was the. You know, the bright light came on, like, okay, I like companies that involve human beings. I still do. I don't like any business that competes with Amazon software. AI, you know, I. Doesn't interest me. It's not my skill set. So I like. It involves a Human being because, you know, Amazon can't do that. AI can't do that, Software can't do that. None of them can do what a human being can do. It's taking out a, you know, a dent in your bumper. And I started that network and I've rinsed and repeated that formula for over 30 years and own millions and millions of dollars in home service companies using that same formula. It doesn't need to be sexy. I started a handyman company a few years after that. It's an eight figure company, you know, and that just went into more and more and more. Now I own a huge digital marketing company. Same concept. A human being can't quite do what we do. We actually meet with local business owners, go over their reports every month and show them, hey, this is what we did. We had the human element to it. But the point is, you know, other than digital marketing company, none of them were sexy companies. None of them were businesses I was passionate about. Could care less. I'd sell toilet seats if I thought it was a good market and I could make money because it'll pay for all the things I am passionate about. Playing golf, being generous, being philanthropic. We get it backwards. I think we feel like it's the business has to be our passion. Well, okay, I'm passionate about golf. I have no idea how I'd make money doing it. What does it mean? I buy a driving range or I buy a top golf in Charlottesville, Virginia of a city of 60,000. It doesn't make sense if you think about it.
What doesn't make sense?
You have to start a business that you're passionate about. If you really think. I had this conversation with John Tesh on his podcast and he and I went round and round for 10 minutes and finally gave up. And he goes, you're right. My first business that went out of business was a running store. Yes, I loved running and I went out of business because there wasn't a big enough market for it. And I was just.
Well, I think that, like, I hear two things consistently. One is if you're passionate about something, then you probably will pour your heart and soul into it. Like you're willing to work really hard. Right. But on the flip side is you might not be very objective about the business opportunity, which is what I think you're speaking to.
Exactly. My point is this is that I'm passionate about all these other things. Well, to do all these other things, I need freedom and I need to make a pretty good living. You can get it in reverse in other words, I'm passionate about. I love the fact I play golf this morning, I'll play tennis, and what other thing? All these things. But if my business doesn't do well, I can't do any of these things. So I, I just think that you have. You have to be careful. I've, like, I talk about a Bermuda Triangle of starting businesses and ideas. We get these ideas and what we tend. See, our tendency is to find something we're super passionate about. And I'm just saying, are you willing to run it through the same beta test that you would do any business plan or startup? The tendency is when you're passionate about it, you bypass that. The only beta test you have is, I like it. I'm passionate about it, assuming there is a market waiting for it. When you're the only objective, you don't run it through the objective test is my point. Yeah.
What are the other parts of your Bermuda Triangle there?
Yeah. The second one is you hire friends and family. You know, your first critical hires. They are critical. Show me. Bill Gates hired Steve Ballmer. Okay, there you go. You know, Steve Jobs hires Tim Cook. And you can kind of go down the line, Mark Zuckerberg hired Sharon Sandberg. No family and friends in these early hires. But we do, we do that well. They don't confront us. They're grateful to have a job. And you start off with just tremendous mediocrity because you don't do the hire that moves the needle.
Yeah. If you hire the thing closest at hand. Well, I think it's interesting is you start out. You start out, and we've talked about this with a few past guests, being interested in seeing a problem worth solving, and that's a really useful thing. An awful lot of entrepreneurs start off with something that they like to do, can do an area they're interested in. Right. And they try to turn that into a business.
But.
But they can lose some objectivity, is what I hear you saying there, which is, I think, really a valid, valid point.
Or you get caught being the technician because you're so in love with it that you're, you know, you're the baker and now you're the lead baker. You have a bakery and you're the lead baker, and I. It doesn't allow you to be the. The entrepreneurial addict that can keep starting new businesses and new businesses. Example, I've never once ever heard Jeff Bezos talk about his passionate love for books, yet he started Amazon. I've never have anybody in any interview ever heard Jeff Bezos say the number one product that I love since the day I was books, I sat and read books. No, it was the number one sku. It had the biggest product. There's more product, you know, different products and books than any other single product line. So if you can kind of get that, all the rest will fall easily. You know, if you can figure out how to sell every book that's possibly out there, that's the, you know, that was kind of the beta model to be able to do everything they're doing today. But I've never heard him talk about his passionate love of books. But that was Amazon.
Yeah. So you start, you figure out very early on, find a problem, fall in love with the problem, and figure out how to solve that problem without doing it yourself.
Yeah, Never, never do it myself. And here's a key point, Ma, Ma. You got to have a massive market. Unless you're selling, you know, yachts, you know, airplanes, you generally need a very demanding market. So I, I like to find something where there's a problem that's, you know, that I can solve my business can solve it where there's a tremendous demand for it within the area I live. Okay, example, you know, I wouldn't have a surf shop in Charlottesville. You know, you got to use some common sense here. And I find that people in their businesses, they don't go into it objectively again, they take an idea, they're passionate about it, they run with it, they have no idea whether to work. They just like it. Number two is they hire family and friends. And the third biggest problem why businesses fail is they're a schmuck. You can't fix stupid. You can't fix lazy. You can't fix undisciplined. You can't fix unlikable. Only Steve Jobs got away with being an a hole. The only one, Only one, you know, had just a personality that, you know, didn't gel. He got fired. Okay? I mean, they got rid of them and then brought him back a decade later. I mean, he generally, you have to have certain qualities as an entrepreneur to be successful as an entrepreneur. I mean, we sometimes forget that, you know, half of them do fail and 90% fail by the, by the 10th year. It's a hard business.
You know, it's interesting, a lot of people who work for Steve Jobs, including some I know say, you know, Steve had, was demanding, was not the easiest person to hang with, but he demanded the best of you. And the abrasiveness you knew was calling for a better you. And Better work. And, and so they, they took it. And I think there's something there to that. Like, you know, that Elon Musk is extraordinarily innovative and yet he seems kind of like an. Oftentimes a jerk too. Puts his foot in his mouth and.
Says and there's no. I think with, with an epic a hole. Yeah. I say with genius typically comes with it. But I'd say to you, listen to me, when you're Elon Musk, you can be that. I mean if you're in that outlier, you know, you earn the right. I would say Nick Saban is probably that way. Okay. To be fair, I got a lot of the highest echelon they are because they're so maniacally focused.
Manding focused. Yeah.
Right. But I don't think we get through that. Our first startup is business. You know, we've got to earn that right.
We've been talking about things that really work. I'm curious stories or examples of things that you screwed up. I know you, you like to tell.
Podcast is limited. Right. Length. We're gonna do the 24 hour marathon here. Audience. So let's line up. Get a pillow. The biggest thing I failed in is hubris. When you start starting businesses, you feel like you can. Anything you do will work. And, and I, and I took a business that I knew nothing about and it wasn't even a problem. I started a retail business. So stupid. And it went under within three years. And, and I had, there was nothing about it that I should have touched. It wasn't like it didn't solve a problem. It was just kind of like I just thought I could. Yeah, I just thought I could make money with it. To me it was like it looked too easy. If something looks too easy, there's a reason it's not. And so, you know, and I lost a lot of money and I learned that, that it had no synergy with anything. I had no synergy with my existing companies. It didn't fall in that model of human beings and service oriented. It didn't fit anything. But oh, I could make it work. You know, I see like an opening store in like the mall of ours. Like they had an open. Oh, like I'm going to just throw a business in there. I mean that's a great location. I'll make it work. Yeah. Didn't work. Yeah.
I think a lot. There's something there. For a lot of us who at one point or another have had an idea and there's definitely different classes of entrepreneurs, they're ideation founder types who are brainstorming ideas all the time and often script their companies because they've thrown too many ideas in them. Right?
Yeah. No, I mean I try to be really focused on one thing at a time, you know, business wise for my company. One clear objective. We try to add one revenue stream a year. I, I define that as anything a quarter of a million dollars or more. Anything under that is just a part of the way we do business. I don't consider it that, but I try to add something, build something went in our company, add a division, add a new business, but some something that brings a quarter of a million of revenue.
So when you look back at the car wash business, car detailing, you did car washing, detailing, everything, it was auto.
Detailing, just pure auto detailing.
So did you figure out if there was any competition? Did you compare what it cost to get someone to do it versus what you could charge for it? That kind of thing.
Stuff. And that's why I wrote my book the World's Greatest Business Plan. Because your business plan doesn't have to be rocket science, but everything you mentioned you do need. Who was our competition at the time? No one. Car washes. Okay. Nobody was bringing water to your house. Okay. Or to that. So that's why it was so good. Pricing, you know, just. We figured a little under a hundred dollars. There was some people doing detailing at shops at the time, but nobody came to you. So we kind of kept our model just a touch less than theirs, but we would make it a little more convenient. They were about 129. We were 99. This was like 30 years ago. Which was actually really good money. I think you have to do all the above. You got to know your competition is. You got to know what your value proposition is. Ours was we were going to come to you, which gave us a unique advantage because we weren't wasting time picking up your car, driving it somewhere, you know, because sometimes you'd go pick it up, bring it to your shop, clean it and then drive it back. There's liability in there and all that. So we felt like we had something really unique. And that same model I've used in every business since then, you know, I give a great piece of, you know, something you can take for what it's worth here. Audience, if you want to figure out how to set up a company, this is kind of what I do. Find the one promise that if you could make and deliver on that your competition isn't that is so good, people would chase you down for your Business. Think about Domino's Pizza. At one point, it was bringing you a hot pizza in under 30 minutes. Extraordinary value proposition. It literally separated them from every pizza delivery place. That one sentence, that was a very audacious promise to be able to get you pizza that was kind of hot within 30 minutes. I mean, they drive through your neighbor's backyard to get it to you. Don't get me wrong. But the point is it worked and it separated them from everybody. You got to have a promise that so separates you from your competition. Then you got to figure out how to deliver on. That's the hard part. But that, that's what should be in your brain when you're looking to start a business. Like, people would chase us down. Amazon, if we could get, literally, if we could get you everything within 24 hours. Walmart, if we could create a store within, you know, air, you know, not big cities that have everything at a fairly affordable thing. I mean, you can look at all the, all the great businesses. That's what they did, every one of them. Southwest Airlines, you know, what if we could create, you know, low, you know, lower end flights, you know, how could we do it? That's exactly what they did. You can go, you know, Microsoft. What if we could create an operating system that, you know, boom, back then you had to type in like all the codes and stuff to do a computer. Remember, like the Commodore computers and stuff and they created Windows, you know, all the great ones find the one thing that's so good that if they pull it off, people would chase them down for their business. Warby Parker, with, you know, how they did glass, you know, buying glasses online, you can keep going down the line. The ones that did it. That's the secret. That one, that one audacious promise that you can deliver.
Solving a problem or finding a problem, figuring out how to solve it. Right? That's, that's the, the crux.
Solving it in a unique, in a way that's better than everybody. I mean, there's problems out there, but everybody's solving them kind of the same way. You got to find a unique way of solving it. At the end of the day, you got a, you know, competitive advantage. Why, why should I do business with you as opposed to them? You always got to answer that question. That's why I like this one promise concept that I've always talked about. Because if I line you up next to your competition, what's your promise compared to theirs? Like Zappos, one year warranty, I read, I remember that years ago. I'M like, that's got to be impossible. But they must have did the math and realized that, heck, you know, after like two months, people don't send things back anyway. But they have a one year warranty where they don't care. That's at the time when you're doing clothing and shoes, when you don't order things online because you're afraid it isn't going to fit. And they're like, no, you got a year. That was so ridiculous. Yeah, that's probably why, you know, I want them for a billion.
It really is about differentiators. I was very loyal for years to Nordstrom and they would go over the top, fix things and take care of things for me. And one time the cleaners lost a pair of pants to one of my suits. And back when I wore suits. So I, I go in and I'm like, hey, I love this suit. And the cleaners lost the pants and they've looked high and low and they can't find them anywhere. And I've given up. And is there any way that you could reorder the pant for this suit?
Absolutely.
And they, and they said, oh, we'll take care of it right now. And they went out, they found that same suit and in the same size, they go, here you go, here are the pants off this one. And then they sent it back to the manufacturer and to replace the pants. And so they just gave it to me on the spot and they said, hey, they'll go do the alterations for you over there and you'll be ready to go in a couple of days or whatever it was with the suit. And I'm like, oh my God, it cost me nothing. They fixed my problem. It wasn't their problem. They didn't create the problem, but they just created a super, super loyal customer. Now, as a person who sold to Nordstrom for decades, being on the other side of that also has trade offs.
No, but you're right about nor, you're 100 Nordstrom. I mean, I've heard that story too. I heard where a lady one time brought tire tires back to them. Yeah, yeah, yeah. And they took it, you know, so, but, but they are amazing. And, and they happened.
But it's a good story.
It is a great story. But I will say that's my first going into a Nordstrom. I will never forget. Really quick. So I remember going up in Annapolis, Maryland, I went up the escalator to the men's section. I literally said, this is the way heaven will look. There'll Be an escalator and you're going to end up in a Nordstrom men's. Somebody was playing a piano. It was like, this is like shopping nirvana.
Yeah, yeah, yeah, yeah. So in your day, like today where I live, there's at least a dozen mobile detailing, auto detailing things. Right. It's really common. I know other people have scaled them to corporate office parks thing and I think it's probably evolved where you are. Can you share some other examples of either your companies or the ones that you've worked with and now that did something different? I'd love to put a few more of those because I know you've got plenty.
Well, that, that company was Waxmaster mobile detailing. I did sell it, but they did clean my cars like three weeks ago. So they're still around. So it's still a durable business model. Yeah. Okay. I started a handyman company. Everybody's like, well, what's that? I just. Again, let's think simple here. I'm living in a very nice housing development. I own a magazine in 21 cities. I'm making a very, very good living. Like 30 years old. I cannot get anybody to do any work in my dining. I want to convert it into an office. And it's hard to get your mojo when you got a chandelier over your head. Couldn't get anybody to do it. I'm asking people in my neighborhood. I'm asking at the pool, the tennis courts, like, anybody know a great handyman? No. Okay. I launched it, Advantage Handyman, our fourth week in business. We had 55 phone calls that week for business. 55 phone calls. I knew then I did the holy grail. Within three years, we're doing over a million dollars a year. A million dollars a year in a town of 60,000. That's crazy. Number Mr. Handyman came to Charlottesville. I put them out. They left within a year. That's how dominating of a stranglehold we had here. Case Handyman sent them packing. Sent Mr. Handyman packing. Sent Case Handyman packing. These are huge franchises. I do super bowl ads, World series ads. There's no comparison in the stranghold. We did it, but then we just kept adding. We did Handyman, then we added, you know, roofing, siding. We're getting ready to do solar. We have a, you know, a large scale additions. We've done custom homes. We, you know, we have a kitchen division, a bathroom division. Like nine different divisions within. You just kept rinsing and repeating you're doing different services. Yeah. Now we have, you know, we Own an entire corner of a street. You know, it's huge. Now the idea of a problem. So four, four or five years ago, about five years ago, obviously digital marketing becomes huge. You know, everybody's kind of doing it different. I'm, I and I'm old school, so I'm typically was postcards and val packs and TV and radio. So I didn't understand this at all. And my competitors that, you know, work their way in and all these little niches, that's all they were doing. And I didn't understand. I know, well, I better figure this out. And so I tried using people all around the country. You know, you kind of, you know, Google a company, you never knew who they were, you know, they'd send you these little spreadsheets that you never understood. So eventually my radio station, because all the local people wanted to start selling digital marketing. So everybody was trying to pitch me because I had a big advertising budget and I'm a whale if you could nail me. So they come in. I'll never forget this was in November four years ago. I'm meeting with the radio station, they bring in all their bigwigs and they're pitching me. I'm doing digital marketing with them and I'll share with your audience how you can always find an opportunity. I'm listening to it. The quietest person in the room of theirs was the smartest guy in the room. And everybody gave me their business cards. At the end, I threw away all their cards and kept this guy's card. He was the least impressive of their group, the way they were acting, but I knew he was the smartest. And I called him the next day and I said, james, listen, I will hire you guys, do all my digital marketing. We'll use a generous budget. But this is what I want. I don't want you to email me any spreadsheets or all this little reports because I don't understand any of them. Agree to come to my office once a month for 15 minutes and tell me what the hell I spent my money on. Is it working or is it not? What do we need to change that isn't working if it's not just 15 minutes? The old George Bush staff meeting. And I said, and oh, by the way, you're going to come work for me or you and I are going to start a company. I said that at the end of the end of it. So he starts doing my digital marketing. That's in November that year, May of that year. I said to him, I said, hey, James, you ever Been to Disney World, you and your family. Because now he's got little kids. No, we haven't been yet, but we'd love to go. I go, great, let me pay for it. I'm going to send your family to Disney World. He goes, well, why would you do that? I said, remember what I told you six months ago? You're going to come work for me or you're going to be my business partner and this is my down payment. I had no idea what we were going to do then. You guys can Google this gig. Strategic. That's one of our companies. Get started. Marketing is one of our companies. Two years later, we launch them. Okay, they're seven figure companies. They're incredible. But it's. I had a need I didn't understand. Digital marketing. Okay. I found this I knew James was good at. That's the same formula I use. I don't know anything about home improvements. I have a plastic toolbox upstairs. I couldn't tell you the difference between two screwdrivers, but I'm doing millions of dollars in construction. I know how businesses operate. I partner in every single one of my businesses. I have a partner, kitchens. I have the best kitchen designer in Virginia. I have an interior designer, New York Institute of Art, doing my bathrooms. I have an engineer. I have. I. I have partners in every single one of my business. Just like I did with the detailing company. I did a 5050 split with the guy who could actually do the detail. I've been doing this now for 30 years, and it's made me millions and millions and millions of dollars.
Well, even that. Pretty good thing, right? You said to a guy who does detailing, listen, I'm going to give you business, but I'm going to keep half of it. Right? So you've got to be pretty compelling as it is because not everybody takes that deal.
No, exactly. But you got to bring the value proposition. He's good at. You're good at detailing, Great. I said, but I bet you sit home in the winter and you starve and you got to try to go out and do estimates. You're never going to have to go do any of that again. We're going to take care of every. We're going to keep you nonstop busy. You don't ever have to look at a car again. All you do is show up, clean it, and on Fridays you get paid. Same thing. I did the handyman. I did that same pitch to the handyman. You're never going to have to do this again. We'll generate more work than you could ever have to do. You're never going to be sitting home in the winter, starved again. Every construction guy is afraid to sit home in the winter. That's their Achilles heel. And I knew that. And I tell, that's the pitch I use when I interviewed everybody. You'll never sit home without work. I tell, listen to me. My superpower is marketing. You know, I'm a young, aggressive guy. And they believed it. You know, you kind of give that impression that you're probably good at it. And I did, and I backed it up. That's why we did super bowl ads and World Series ads and all that. Yeah, you got to bring a value proposition to it. James would have never partnered with me, but listen to this offer I made him. I told him first because his wife was a stay at home mom. I said, you need to get a raise from your company. You are. I'm like, you are their digital marketing company. I'm like, do you have a non compete. He goes, no. I go, oh, big mistake. We're getting ready to. We're getting ready to make some fun with that. So I showed him what to do, and he went and asked for a raise. And they turned him down. Kept turning him down. This is like December. I said, listen, we're starting a company January 1st. I said, how much money do you make? Told me what he made. I said, I'll guarantee your paycheck for the next year. We're gonna, we're gonna launch this business in the next 10 days. We did. We made. I only had to pay his paycheck. He's probably listening to this. Eventually. I only had the guarantee, his paycheck for one month. I knew he was a superstar. I knew we'd make money fast. And I remember saying to him, I said, james, don't ever get mad at me when I'm making profit sharing because I knew you were a superstar. I said in that meeting, there's a lot of people in that meeting, you know? You know what I mean? And I knew you were a superstar, and I sent you to Disney World telling you I was a superstar. So please don't ever get upset when I make a lot of money because I made a bet on you and I. And, and he always says, no. He goes, I'll never feel bad because I would have never did it had you not given me that one year guarantee. He said, you. He goes, that was, you know, my, my wife would have never let me go quit my job and start a business.
Right?
So you got to find something that's compelling. I mean, yeah, people are not going to do it if you don't know.
That's a really good approach and being really straight about it. And out in the open is good too. I remember hiring some guys for another company years ago and they started to figure out how much money the company was making. I'm like, yeah, but wait a minute. I said, what do you want to get paid? How do you want to work? I let you name everything. And now we're taking risk and working in a way that you didn't want to work and we're trading on that difference. And that's actually worth a lot to people. But it's not a way that you want to work. So chill out and enjoy your work. You got to name your price terms, everything.
And some people will never, I mean, I've had people I partner with and they never quite get it. And you're, you're an SOB and you're this and you're that. I'm like, you're taking advantage. Yeah, you're taking advantage of it. No, the fact is I saw, I saw the opportunity. I took all the risk. Yeah. You know, and occasionally you're going to have that, you know, one in one in 10 situations.
So you're pointing to something here that I think is really useful and that's the whole people side of things. So, and attracting and, and engaging, retaining talent, expertise and then, and then leadership. Right. Because you don't have the expertise in these and yet you're running multiple businesses with, I'm sure, multiple people in them from the numbers and the, and the things you're throwing around. So what is it that you've learned about attracting, retaining the core talent and the leadership talent? Talk to us about that.
Well, you nailed it. In other words, I'm always interviewing, I'm always looking for talent and I'm looking for it everywhere. It has nothing to do with an interview. I look forward on the golf course, I look forward if I'm playing tennis, I look forward at my kids sporting events. I'm always looking for. These are the qualities, number one, they have an expertise in something that I see as a potential monetization. I see there's money there. Okay, so that's it. They have an expertise. Number two is they're a leader. You can't scale anything without a leader. And I can't lead all these businesses day to day. I got to set the overall culture and vision and make some big decisions. But I can't manage, you know, digital marketing company Day in and day out. So they've got to be a leader. Third got to be a salesman, got to be a rainmaker. They got to have that gift of communicating that how and everybody does it in a different style. Like James is very to the facts, very detailed and all that. And I have a little bit more of an energy style. But it, there are a lot of ways to get it done. They got to be a rainmaker because if not you got to hire a rainmaker. So then you got two big hires that are too expensive right from the get go. So you gotta, they gotta be the number one salesperson. They gotta be the leader. I mean you gotta hire a unicorn.
So you're talking with, you found a problem and you're, you're hiring key talent and then you're doing something to change the way they work. But that initial hire in your business is a little bit more of a unicorn.
They gotta have three things. They gotta be a leader, they gotta have an expertise and they gotta be able to sell. That's. They got to have those three things. I found anything less than that, they don't move the needle enough. I ought to just make them employees. I mean I'm going to give you, you know, these are partner, right? This is a person that's going to be have 50% stake whether it's equity and or profit sharing. I'm looking for people. Another super quick story and how it just, I see it. I interview a supervisor. This was five years ago. Never forget it. Super talented. But I'm interviewing. He's a UVA graduate, he's a construction guy, he's clean cut, he wants to be a handyman. I'm like wait, this is insane. I go, I don't know where he was like a history major or something. I'm like stop. I have something better for you, you know. I said, you want to make 850 a week? I said let's do this next interview at my house. So he comes to my house, I hit him with the, you know, hit the garage door opener, the amg, the BMW, you know, blah blah, blah. And we go in the foyer, the 20 foot ceilings. And I go, I want you to be a partner in my company. Why don't you run my entire handyman division? And, and I said, you're going to make a lot more money. I said, I'll guarantee you this $850 a week you want. I said, but I'm going to be, I'd be stealing from you to give you this. Listen, his last Paycheck. He makes way over a quarter of a million dollars a year. His paychecks are so big every week I won't even let my CPA show me the numbers. I get a payroll report, I make her blackout his. I don't even want to see it because I'd make my head beat against the desk. I joke, but I do. I won't look at it because he makes so much money. He's making well over a quarter of a million dollars a year. Every Christmas party, his wife comes up, gives me a kiss on the cheek and whispers in my ear thank you so much. Well, I could have hired him for $850. If he'd have made 1200, he'd have killed for me. He makes over a quarter of a million a year. When you interview people, you've got to see potential in them that they don't even see themselves. He never saw that in him. I'm going through the interview, I'm like, you're articulate. You got that little bounce in your step. You have energy, you have expertise, you got a degree, you're well spoken, you're organized. I'm like oh my gosh, what I can do with you is scary. And we did.
And so then how do you grow the companies after that? What's the people side from there out? I mean who's doing the recruiting of the people?
How are you building all my partners, I teach them how to do you know the superpower of always be interviewing. That's what I tell my partners. Always be interviewing. You can always hire if you meet a superstar. There's always room on the roster. So we're always interviewing.
Golden rule it is.
There's always room on the, there's always room on the roster. So I teach them, you know, it's over a two to your two to three year period. I teach them kind of what I do and but enough to get them up and going. But they run the day to day and I, you know, I like smart people too. I talked about sales, but smart is just not even a non negotiable. Like we wouldn't even be sitting down talking if I didn't think they were bright. The bright people can, can handle, they have great capacity. Smart people can just do many things at once. People that just aren't very bright. We've met them. Come to my family reunion. Okay, we've met them, but they're just not overly bright. Super likable, not overly bright. I like bright, just pretty bright.
Your so and, and then what's the role or value culture in your companies? Are they all the same? Are they similar? Are there a couple of common rules that you have? Are they each really unique and different?
This is going to, like, upset everybody. I think culture is the most overblown thing right now.
Definitely will upset our audience, but go ahead.
Okay. Challenge your thing. Number one, is that 90% of your people want to come to work, get paid, and go home. To be honest with you, they want to work in a company that's honest and fair and durable, sustainable. But I think we just try to make this so holistic, you know what I mean? Work is. It's only a third of their day when they go home. It's not their job as an employee to think about your company or even care about your company. They're a parent, husband, a wife. And I think we ask too much of people, like, it's this all in whatever. You know, what I ask my employees to do. Our culture is very simple. When you're on a job site, make the decision that you would make if it was your house. That's our overriding culture. If you're wondering how to do something, if it was your house, you would. How would you do it? Don't ever take a shortcut. Number two is all my guys. I don't use subcontractors, so they all get paid by the hour. Why? Because I don't want them to ever rush. So I create a culture in how I run my business. But I don't need to wave 100 flags, though.
That's like, you know, do it like it's your house.
Great fundamentals, but I don't believe in the never ending. Yeah, you know, I gotta wave my culture flag. They know what I'll fire them for, and they know what I'll give them a raise for. I mean, I communicated from the very first interview. I don't want you to ever. You never have to rush. I pay you by the hour. Do you realize if it takes you longer, you get time and a half? So don't ever rush on a job or take a shortcut, because I'm going to tell you what I told you right here at this. I've never asked you to rush on a job, number one. Number two is if you're making a decision, make the decision that you would do if it was your home. If you can't reach any of us and you have to make the call, the call is, what would you do at your house? And I hope you do the thing that was right So I instill that from the beginning. But I don't wave like never ending Kumbaya moments. I think we're get. I, I get, you know, I have a big cop podcast too and everybody's a cultural, a culture expert now. I'd love to bring them into my company. Yeah. Because they would get, you know, my guys would be giving them the middle finger. You know, culture, it rolls out of the ownership, it rolls out of the theme.
Maybe doesn't have games and tokens and things like that, but, but you have a culture, right? Right, A culture.
You do. And I always say this, do the.
Right thing and like that kind of thing. That's you do.
I'm being funny about it, but the problem is what I have with startups. Startups start with culture. Sounds great in theory. Make money. Because if you can't pay anybody, you're not going to have a company to have culture with.
That's the basic.
But they do, they all start with the Kumbaya, you know. No, be profitable. Then you'll have credibility and you'll get the culture. The culture is going to resonate from the ownership and the partners anyway, good or bad. If you're a thief, a liar, you're going to hire people probably very similar to you are going to. They're going to adopt your behavior. If they see you treating clients good and they see you fair and they read your contracts and you know, you're not saying, hey man, why don't you add this, try to jack this up, drag this out. You know, they know when you're, when you're shyster.
I think there's some super nuggets in here. Let me recap. Before I do that, let me remind everyone we bring our show to you every week. All the shows and more@scalingcoach.com if you want to drop us an email, send A note to scalingcoach.com info scalingcoach.com is the email to send to. So easy to remember, right? We've been yammering at you forever and ever and ever. Things I heard here, like, don't forget, fall in love with the problem. Not something that you're passionate about. Be passionate about a problem and it doesn't have to be anything that you have any expertise in. Then get great at people, attracting, finding, developing talent. But don't get silly with things. Remember the basics. You're providing differentiated value. Do something and unique and compelling. Right. In a town without any mobile detailing. Provide detailing. If there's a bunch of nice cars sitting outside office parks or fix. Be a handyman who fix home like basic service business delivering value for money, doing it better than or doing something that nobody else does right. Don't get silly about the whole thing like really obvious basic things I think is really useful. Fall in love with those problems. Get good at the people. Those are the things that I mostly heard. If you want more information, you want to listen to the show like all that seancastrina.com we'll put it in the crawl here, we'll put it in the show. Notes be all over the place. SeanCastrina.com is where to get more also easy to remember. Sean, thank you so much for joining us on the show today. Sharing a little bit of your wisdom.
And experience or I stirred up the pot. But hey, I wish everybody great on.
Their entrepreneurial journey so there's lots of gold in there. Thanks again everyone for joining us. We'll talk to you again next time. Big thanks to Vern Harnish, author and creator of the Scaling Up Framework, the Rockefeller Habits and the folks at podfly Productions who get our show out every week. And Aada Mitchell there in the background getting our guests lined up. Show ready, show distributed, all that more. Talk to you again next time everyone. Keep scaling up. Bye bye now. Are you ready to turn your goals into daily wins? You should check out our Scoreboard software powered by Align. It's the official software for Scaling up With Scoreboard. You'll get an AI driven coach for priorities and KPIs and and it'll help keep your team focused on what matters most. With Align, you can track your goals in real time and you'll even see results on the go. With their mobile app. You can rest easy knowing that Align has world class onboarding and support to set your team up for success. This is really more than just software, it's what I actually use to manage growth in our Scaling up client teams. Unlock clarity and results with Scoreboard by Aligned. To try it now go to aligntoday.com Bill G One more time aligntoday.com Bill G that's aligntoday.com Bill G Check it out and try it now.




