Creating Confidence with Heather Monahan - Confidence Classic: Bet on Yourself and Build Wealth Fast with Sean Castrina

Episode Date: July 15, 2025

Think a steady paycheck is the “safe” path? Think again. In this episode, I sit down with author and serial entrepreneur Sean Castrina to talk about what it really takes to create financial freedom, move through fear, and build the life you actually want. Sean shares how he launched more than 20 companies over the past two decades, the power of partnerships, and why taking bold action is always the better bet. I also share how I got scrappy in the early days of my speaking career and why confidence must come before the payoff. Tune in to flip the script on risk and take back control of your success. In This Episode You Will Learn Why most people never launch their dream business. Sean’s top strategy for building a business fast. How to make smart business moves without waiting for funding or “the right time”. The skill that separates successful entrepreneurs from everyone else. How to avoid the ‘Bermuda Triangle’ of startup mistakes that sink businesses. Resources + Links Get Sean’s book “The Eight Unbreakable Rules For Business Start-up Success“ HERE! Listen to Sean’s Podcast HERE! Sign up for a one-dollar-per-month trial period at shopify.com/monahan Download the CFO’s Guide to AI and Machine Learning at NetSuite.com/MONAHAN. Want to do more and spend less like Uber, 8x8, and Databricks Mosaic? Take a free test drive of OCI at oracle.com/MONAHAN. Get 10% off your first Mitopure order at timeline.com/CONFIDENCE. Get 15% off your first order when you use code CONFIDENCE15 at checkout at jennikayne.com. Call my digital clone at 201-897-2553!  Visit heathermonahan.com Sign up for my mailing list: heathermonahan.com/mailing-list/  Overcome Your Villains is Available NOW! Order here: https://overcomeyourvillains.com  If you haven't yet, get my first book Confidence Creator Follow Heather on Instagram & LinkedIn Sean on Instagram & Website

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If you want to make necessary changes in the modern business world, pick up a copy of the HR Renaissance today. I found that there's things that people listen to. I call them there's like six myths, six lies that keep people from starting a business. One is that they think they got to have this ton of capital. I've never put in more than $20,000 in a startup yet, never. And I like 10,000 because I started at a micro level. I just want to get a pulse.

I want two things. I want to have proof of concept. I want to have proof that I can deliver the service or create the product, whatever the case may be. And then I want proof of traction that I have a wanting audience. I don't go all in. I don't quit my job until I have those two things. Man, I am hesitant. Come on this journey with me. Each week when you join me, you're going to chase down our goals, overcome adversity and set you up for a better tomorrow. That's a no-seeker.

I'm ready for my close-up. Tell me, have you been enjoying these new bonus confidence classics episodes we've been dropping on you every week? We've literally hundreds of episodes for you to listen to. So these bonuses are a great way to help you find the ones you may have already missed. I hope you love this one as much as I do.

Hi and welcome back. I'm so grateful that you are here. This has been the craziest week. It's just been all over the place so I've got to break it down for you a little bit and get you up to speed in what is going on. So this week I had a really busy week because it was the largest virtual speaker event that I was part of so far this year. I was super excited about Damon John was one of the keynote speakers along with yours truly the billionaire CEO from IT Cosmetics, Jamie Lima was on, Pete Vargas, some really big, powerful speakers that I was so grateful to be in the lineup with.

So it's sort of funny, I remember, I guess probably two years ago, I started like the quote unquote speaker career, right? And at first I wanted to get agents, and then I got agents and nothing. So then I was like, okay, forget this, I'm gonna go pitch myself. And I just started pitching myself everywhere and anywhere

and taking whatever I could get. And it definitely started slowly. I was not any less of a speaker then because I had spoken for 20 plus years in corporate America. I have a lot of experience doing it. I really love doing it and I'm really good at it. So it was frustrating to know when you're really good at something, you have a ton of experience behind it, but you're not connecting

and you see other freaking people doing well that aren't as good at it as you. That's sort of, I mean that probably sounds crappy, but I'm just calling it the way I see it. Two years ago, I was really freaking frustrated, okay? I would go to events or attend something and see a speaker and think to myself, oh my gosh, that person is not that great and know that person was getting paid a lot of money and I wasn't and it was just that grind for really a couple years. And then a year ago in September, I was part of the hyper growth conference thanks to a really good friend of mine, shout out to Scott McGregor,

who helped get me that opportunity. He pitched me because he knew the people throwing the event. He luckily highlighted me and then they said they wanted to hire me. So that was a really big moment because I was interviewing Sarah Blakely live on stage in front of thousands of people and it went amazing. It was such a great event and we we did a great job. So those kind of momentum opportunities where you're going to the next

level, you're finally taking a bigger stage, you're finally getting paid more, you're finally showing up in a lineup with some much bigger, you know, top shelf names. That's when I thought, okay, this is where it's going to blow up. And then next I had my Ted X talk and I killed it. And I thought, oh my gosh, momentum, it's picking up, it's picking up. And it really was starting to pick up. And then the pandemic hit and I was getting booked for a lot of events and engagements for good money through my different, a couple of different agents that represent me.

So I felt like after those two years of really just grinding it, it was finally starting to click. for good money through a couple of different agents that represent me. So I felt like after those two years of really just grinding it, it was finally starting to click. And then the pandemic hit and it just completely stopped everything. A year ago this month, I gave my TEDx talk and it's just so crazy that this year

halted everything until about a month and a half, maybe a month into the pandemic, I was asked if I would be hired for a virtual speech. And at first I thought, I don't know if I can do a virtual speech. How can I bring the energy and connection and power that I'm able to bring in a live stage when I can see people and now not being able to see,

I didn't know if I could do it because I see some instructors in spin can do it amazing in person, not so great on the zoom. And I just wondered, you know, how do you know what that intangible is and if you got it or not. So I offered a money back guarantee for my first job as a virtual speaker because I didn't want to leave anyone unhappy. And it went great. And then I started getting more virtual

speeches. And so it's been building back, but it's been much slower than what was happening before. I had kind of hit that tipping point a year ago at this time, and it really started clicking. So again, now I'm sort of starting over. But this event this week that I was a part of was the biggest one yet. And it was amazing to get the opportunity to work side by side with so many phenomenal class A top tier speakers. So when you start seeing yourself at that next level and other people see you you know on that roster with people at that next level you become that next level and that's that was a really powerful moment for me this week. However like

anything when it rains it pours I had three different speaking engagements this week I had that huge potential board of director meeting this week with another company, and I had my regular coaching clients, and then I'm getting really close to my HarperCollins leadership deadline. I have to have the book done in and completed by the end of November, which is, you know, I mean, what are we, six weeks away?

Five weeks away, it's pressure time. So then I've got, my son is, you know, working from home with Zoom school. And I swear anything and everything that could go wrong did. My toilet broke, I needed to call the plumber. My tire is flat now on my car. I mean, there are so many random things. It's just the universe, I guess,

testing me to make sure that I'm super strong. So there you go. So one of the things that I guess, testing me to make sure that I'm super strong. So there you go. So one of the things that I do, and it's so funny because when I used to travel a lot, it was logistically harder, right, because you couldn't get to see your kid or you couldn't get to this place or that place because you were on an airplane. So in some ways, even though this week was so crazy, it's still easier than, you know, flying on three different planes in one week and staying in different hotels and trying to figure out the logistics of what place studio am I supposed to be at.

So in some ways, even though it's crazy and painful being home, it is it's manageable. And that's sort of the way that I approach this week. But I did get super stressed out and I told my son to listen. This week it is my hell week and I need to knock it out of the park so really give me your best effort that you can to help support mommy in this week and then by Friday we'll be back to normal and it'll all be good and so he's a great wingman and helper and definitely helped me with that but you have to ask for what you want right and communicate with people it's critical. So I prepped and practiced,

and I trust myself that words will come to me. And I really focus on, I had a short speech, the first one was 30 minute. And so I focused on two different stories and a bridge to connect the two stories, because people love stories. And in that bridge is really the teaching of what I was imparting on people.

And the first one went amazing. It was all women. It was a network marketing company and it went fantastic and I was super excited. These ladies were posting so much on social media after and that's the cool thing about social media now. Even when you're remote, people can support you and give you a shout out and you can see it in real time. So that's so cool. And I get to see what resonates with them. So a lot of them picked one moment from the speech that they really liked and, you know, I write that stuff down in a Word doc to remind me for my next speech. So then the next day was my huge day.

I was the second keynote speaker of the day out of 10. This was Dame and John was closing the day out and you know, oh, this is something I forgot to tell you. So the day before was the first day of the virtual event. I was not speaking on the big event that day. I was speaking the second day and the third day. And on the first day, I wanted to log in because I like to familiarize myself with any venue or, you know, when I gave my TEDx talk, I went to the venue two weeks ahead of time. I want to see where where I'm gonna be so I can picture it. I wanna, you know, figure out if there's gonna be any glitches.

Well, wouldn't you know there were glitches in that first day of the big, big event, which was not my day I was on, but I had my technology test run through that day with the team as well as I was trying to log on as a viewer just to get a sense of how it worked because I knew this company had a proprietary platform that they had created you know because everyone's trying to find ways to innovate and make virtual more engaging and better and more impactful which I

cheer on and get however I have to tell you that first day I could not log in it just wouldn't work so I was getting really nervous that if I can not log in. It just wouldn't work. So I was getting really nervous that if I can't log in, what if no one can log in and now what if no one shows up and then what if damn I can't log in and I'm supposed to be on live coming live from my apartment. And so I was freaking out about the technology issues because that was so out of my control. So I was messaging the team saying, guys, this is not working. And anyway, they got me a link that I could essentially view the speakers,

but it was just a mess. And it was super stressful on the team, I could tell, because obviously I wasn't the only person messaging them. They were getting messages. I mean, there was thousands of people attending this event. So it was a little stressful for everyone. I wake up the next morning and I see an email from the team that went out to all attendees saying, here is a Zoom link, we're moving the platform to Zoom.

And I was so happy to see that, not for them, because obviously they, I'm sure, spent a ton of money on the proprietary platform trying to innovate, but for me, I've done plenty of virtual speeches now on Zoom, so I'm really comfortable with the platform. I know once I saw Zoom, oh, okay, I'm good. Done, you know, 20 or 30 of these in the past couple of months. This is my kind of jam. I'm not going to have a technology problem. And we didn't, and it went amazing. And I was so, so excited and so grateful. And this was the first time I stood up while giving a virtual speech. And it was so, so excited and so grateful. And this was the first time I stood up while giving a virtual speech.

And it was funny, last week I DMed Ed Mylett, who I love, who's been on the show and who's a huge speaker and such a great guy. I sent him a DM and said, Ed, I'm thinking I should stop sitting while I'm doing my virtual speeches because I'm beginning to think I would never sit in real life if I was on a stage. So why am I doing it at my

living room table? Why wouldn't I stand and potentially I can get more energy and get people more fired up?" And he said, absolutely, I'm doing the same thing now. He said a couple weeks ago I started, you know, making that same move. So once I heard that he was doing it as well, I knew that, you know, my instinct was correct. And so I did my first standing speech and I killed it. It went so well, super happy, got great feedback, which I wanna make the point, feedback is so important. And the head of the event sent me the nicest thank you note

and such positive feedback. And it really meant the world to me. You know, I will run through walls for people that support me. And these guys were just amazing to work with. Yes, we had some glitches and some challenges, but in the end, whenever their next event is, whatever they can pay me, I'll be there and signing on and can't wait to support them

because they were so kind and so thoughtful with thanking me and the feedback that they gave. So please make sure to thank and appreciate the people in your life. It makes such a big deal, such a big difference. So, my gosh, to make a long story longer, I'm like, when does this weekend? So then the next day I had the potential

board of director meeting where I was nervous because I haven't been meeting with people in person unless I'm really close to them, you know, to know, I guess, how well they take care of themselves, socially distance, etc. So I was really stressed out. I also they hadn't told me if I had the board position or not. And it was just stressful. Anyhow, I went to the meeting, the meeting went amazing. The founder is such a great guy, so interesting, super smart. And it was this fantastic meeting, and I got it. And I was pitching myself five years ago for my first board seat and never got it.

And so finally, this is one of my bucket list things that I knew I could add tremendous value. I knew I had the potential, and finally, it came to fruition five years later. So I'm super, super excited about that. So I did not look at my phone the entire meeting, of course, out of respect for everyone there. Wouldn't, you know, I get home and I have a meeting

with one of my clients, I have a plumber coming, and then that afternoon from two to five, I was doing another speaking event for the huge virtual lineup that I had just done the day prior. Now it was their women's day and they wanted me to speak again for them. Well, I look at my phone and there's all these text messages

from the head of the event saying, we need you right now. You need to log in right now. And I had missed it because I was at this really big meeting and I wasn't scheduled to speak for hours. But obviously something bad had happened. I could tell the sense of urgency and tone and the messages was not good.

So I don't know if someone canceled or didn't show or had a technology problem or who knows what it was. But I just responded back, sure. And I canceled the plumber, canceled the other meeting, asked my son to be really quiet in his bedroom and turned the computer on. And then I text back, is this a Q&A or do you want me to give a speech? And he writes back, just give a speech. And I thought, okay, don't forget, I had just given a speech to this audience the day before.

So I knew there would be some, I couldn't talk about the same things I had talked about the day prior. So in my mind, I'm thinking, Heather, what story do you want to go to? And just jumped in my mind was a story of when I gave one of my first big, real authentic speeches, which was at City Year Miami charity a few years ago. And I was going to talk about how that day I learned it's so important to shine your light and be proud of who you are and tell those hard truths. Because when you do, you're serving others and inspiring others.

And it's your duty, you know, to do that, not say, oh I'm too humble to tell people about this. No, you need to tell people because you're gonna inspire them for growth and opportunity in their life. Okay, so that's what I came up with. I'm in basically like a virtual green room with another woman who was gonna introduce me. She was another head of this event and now I knew her from the day prior, right? So she and I look at each other on Zoom and we just start laughing because I knew something was going on. They didn't have time to tell me, obviously, but I was jumping in to help out, didn't know exactly what was happening. I had not been on the virtual event all day because I was at this meeting. So I was so in

the dark on what was happening. She saw my face. I saw hers. And we just bust out laughing. And then she was in the chat thread saying to the tech team, can someone tell us how many minutes we have? And they said none going live now. And she said, do we know what we're doing? So no one really who knows what was going on. But it all of a sudden just said live. So you knew you're up and running live.

Thousands of people are seeing you. And it's just me running and cancelinglling the plum, or cancelling this. It was just so funny. But it was great because she was really conversational. I trusted her because I had worked with her one day prior. And she started just asking me questions. And anyway, I didn't do the City Year speech or talk or anything about that. It ended up being much more conversational and we just kind of were winging it. And I thought it was super valuable, but I was really proud of me and her.

We just both stepped into this window of complete uncertainty and went with it and it worked out great. So you just never know what tomorrow may bring. Just be ready to wing it. Okay. So I'm excited for you to meet my next guest, Sean Castrinha, and he's a serial entrepreneur, having started more than 20 companies over the last 20

years and still seeks to launch a new venture annually. He's an investor, teacher, and highly sought after speaker who communicates with humor and a bluntness that engages and captures his audience. He's the author of eight unbreakable rules for business startup success, the greatest entrepreneur in the world and world's greatest business plan. Can't wait for you to meet Sean. Hang tight. We will be right back. And we are back with Sean Castrinha. Thank you for being here, Sean.

Great to be on the podcast. So it's so funny. I always feel like a person on an island and that I was fired from this high profile job when everyone thought I had it going on and that was my catapult to becoming an entrepreneur. But I found out that you actually might be in that same boat with me. Yeah, I mean, I never thought I'd be an entrepreneur. I always knew I'd have something on the side making me money. I do know you needed something extra.

So, I mean, that was quickly cemented in my brain, but I had the dream job. I was in graduate school, one class away from a master's, brand-new house, newly married within that timeframe. I think we were pregnant with our first child, if I am correct. And yeah, went in one day, there was a leadership change and boom, I was out.

And like, this was the one where my reputation was like a top 25 company within the field that I wanted to get in. I mean, this was like blue chip of blue chip and then boom, gone. So how did you bounce back from that? Cause I personally know how painful that punch in the gut is.

Yeah, I mean, you go through, first you're embarrassed, and then you go through, how do you tell everybody? And then you quickly decide, well, how am I going to pay my bills? You kind of go through that survival. And I know that's what I did. And it's just one of those where I did get the epiphany. I did get the aha. Literally, when I was being let go,

my brain was literally putting together that, you know, fight or flight. And it was like, this is never gonna happen again. Like, I'll be working for somebody short-term, but I'm getting my ducks in a row. I'm gonna dictate my career. But I'm never gonna, like, work really hard, do everything that I think's right,

and then one day not have it. dictate my career, that I'm never gonna like work really hard, do everything that I think's right, and then one day not have it. So smart, yet so hard to make that leap, and I hear from so many of my listeners that they want to make that leap. They're not happy, they're not in the dream job like you were, but they feel paralyzed to actually go for it. Yeah, I mean, I found that there's things that people listen to. I call them there's like six myths, six lies that keep people from starting a business. One is that they think they got to have this ton of capital. I've never started, I've started more than 20 companies and I have, you know, businesses

are, you know, seven figures, one that close to eight. I've never put in more than $20,000 in a startup yet. Never. And I like 10,000 because I started at a micro level. I just want to get a pulse. I want two things. I want to have proof of concept. I want to have proof that I can deliver the service or create the product, whatever the

case may be. And then I want proof of traction that I have a wanting audience. I don't go all in. I don't quit my job until I have those two things, man, I am hesitant. So I think, again, the myths that keep people from doing it is they think they need to have this ton of capital. And second thing, they think they need to quit their day job and I've never quit a job, I just worked another one.

So most entrepreneurs work 100 hours a week in the first five years anyway. So work 40 on your business, 40 at your real job, it's 80, there's gonna be a sacrifice. I don't know why you would quit your day job. To me, it puts way too much financial stress on you. You got your personal financial stress and then you have the business's financial stress

and that's like the perfect storm of bad things. So I like just stay at your job and then when you can get the company to produce 50% of your income, then you can have a jumping off point, but you gotta earn the right to quit your job. Isn't it difficult though, and I just hung up with one of my clients

that's in a very similar situation to what you're describing. She's in an existing company. She wants to launch her own, but she has so much trepidation around promoting this business and trying, you know, a client acquisition strategy that's out on social media or in advertising, because if her current company gets onto the idea that maybe she's going to be leaving, maybe they fire her and that's keeping her stuck.

Yeah, I had somebody in a very similar situation that I partnered with. I mean, clearly if you're doing something that directly aligns with what you're currently doing for another company, you gotta leave. Cause that's a con, I don't know if, do you have a no compete agreement, but typically something like that.

Once you start going after clients, they're gonna find out and it's not gonna end well. So how did you do it when you had that financial pressure on you? You had been fired, you didn't plan for it, how did you pivot so fast? You know the survival thing, you know the number one quality that great entrepreneurs all have is they're great salespeople. They just have that. You need to have it if you're not, but almost every lead entrepreneur has that pitch man personality. They may partner with

somebody quieter who's more detailed but they generally have that. So I went and sold insurance and I made a ton of money. It was you know I joke you know I mean it's I made silly money I just didn't like the business it was ucky but making money it was very you know it was easy to make money in it so it served its purpose for a short season made money and then I started my own companies and the rest is history. So how do you figure out who those people are, which startup idea you want to move forward with?

Who are the people you want to partner and work with? I mean, typically, businesses come from one of these ideas. You either solve a problem that you personally experienced, you listen to so many business, tax resolution or timeshare, Tommy John underwear, you can keep going, my pillow. It always starts with a story. So normally you're going to solve a problem. Number two is you might meet a want. It's just a simple want or meet a need. Like a need is example, a transportation or a restaurant. You know, you have a need for, you know, that's like a diner.

You have a need for food. Then you have the next level. I talk about wants. A BMW is a want. A Sandals vacation is a want. So you know, you have businesses that fulfill needs and wants. And then finally, you entertain. If you can entertain, if you can get cameras on you, you have a following, whatever the case may be,

you're gonna make money. Kim Kardashian all the way down the line. So there are the four ways that you typically are gonna make money as an entrepreneur. And solving a problem, meeting a need, satisfying a want, they're the three that typically create 90% of your businesses, probably more than that, 99%. So is it that people don't know

to start a business around these principles? Why do so many of these startups fail? Oh, they do what I call the Bermuda Triangle of entrepreneurs and why, if you look at this three quadrants, first thing is that the founding entrepreneur doesn't allow their startup idea to be exposed to criticism.

It's in their head, even when they pitch it to you, when they share with you, they go, oh, this idea is so great. And they get into it. And what do you say to them? No, it stinks. It's bad. I can't imagine anybody would want that. I've never even thought about that business, or I would never pay for that.

So they pitch it in such a way that they don't really open up to criticism. They don't test it. They don't run a business plan. They don't beta test it to see, OK, is there other people that really want it? Are people willing to pay that kind of price? Example, I had a friend. This is just insanity. Within the last six weeks, he's been doing one line of business for 35 years, where he

has made millions of dollars. And he basically, they buy him out and they gave him a six month, you know, which Macaulay is when they get ready and they give you six months. Lord knows I never had that. Severance package. Yeah, it's six months, Severance package. I didn't have that. And then he brought me like this Tupperware bowl of granola bars that his wife had just made.

He goes, I'm going to turn this into a business. Tasty. They're incredible. Not only did they not really taste that good, but I'm like, I can think of 10 places I could get protein bars from. But he was so insanely passionate. And I literally walked him down my driveway and I said, listen, you're not gonna like what I'm gonna tell you. Go get a job in what you've been doing for 35 years.

If you wanna make this a hobby, that's fine. But this is not a business right now. How did he receive that hard advice? Oh, anybody who knows me is like, probably not that surprised by my frankness, but I'm like, no, I said, you're gonna put unnecessary stress on your family. Your family is used to you making A, B, C, and D. I said to me, this is a side something. This is something you need to do

at a small scale. Sell it at a county fair. Sell it via social media. You got to get it tested. Sell it to maybe sports teams in the area. See if they like it. You got to get some proof of concept here. This is not an all in business, but that's what people do. So that's like the big mistake is founders do not expose their ideas to criticism. And that's really, really bad. The second thing is, is that, you know,

they don't understand marketing at any level. They think they're going to be like a word of mouth business. And simply put, they have no real strategy to acquire customers day in and day out. They leave that they just assume customers are going to show up. And then the final thing I find that they do the other kiss it, you know, just does them in. They hire family and friends. Bad staffing, you know, I got Uncle Billy working a front desk.

Everybody loves Uncle Billy. Uncle Billy is a moron. You know, his guts Uncle Billy working the front desk. Everybody loves Uncle Billy. Uncle Billy is a moron, you know? His guts hanging over the thing, you know? He's got three buttons down on his shirt with his hair, you know, his chest hair hanging out. You can't tell him that because that's how he looks at family reunions and he's not gonna change when he comes to sell in your carpet store.

You know, whatever the case may be. You know, you got a staff. You got a staff to win. I always say a big vision with a bad team is a nightmare. Why is taking might appear important to you? Let me tell you why it's important to me. I feel so much stronger in my workouts. I'm recovering quicker than before I took it. I have more energy. I want to proactively preserve my health,

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Go to Shopify.com slash Monahan. Shopify.com slash Monahan. I asked you to try to find your passion. So I have some, some of the people that I work with had that word of mouth strategy, which is essentially they've done nothing other than sell their product or service and business just organically came to them until the pandemic hit. And when the pandemic hit, people weren't, you know, buying off want anymore. And suddenly these pipelines of potential customers dried up. How could you insulate or prepare someone for something like this insane pandemic?

And how do you advise them to pivot quickly? Well, I have somebody, you know, a very well-known person who is in the expert space and where, you know, everybody's selling a course or something of that nature. Let's just kind of leave it at that. And he was in $100,000 mastermind groups and all of that. So everything he sold was within his network.

Well, that completely dried up. See, to me, that's just a bad business model to start with. Anything that is so singular, like it has one way in, I don't like that. See, to me, it's not a durable business model. I want to know that there's five ways customers can buy from me. When I find something that works, let's say I run a radio ad and it works, traditional. That's great. I don't just stop with radio. Now I want to find a TV ad that works. Then I want to find a digital ad that works. Then I want to find something else

that works. I want many hooks at work. People, they get one and they just get satisfied. And I do a doomsday scenario every year between Christmas and January 1 on what would put my companies out of business. And I look at every scenario that could happen. Nobody could plan for a pandemic, obviously. But I was never dependent. I never had all my profit in one area of my business. No one form of advertising was producing exponentially more than the other. I really had very diversified marketing.

And when the pandemic came, we took a little hit, but we didn't get absolutely decimated. And with the marketing, are you just testing and testing and evaluating the data? I spreadsheet everything. There is no other way to know. I spent money that I thought for sure would work and didn't work, and then I've done stuff

that well outperformed anything I could ever imagine. And I know what moves the needle. I can pull the levers any day I want to tinker with marketing because I study it, I keep track of it. I could, you know, we chart everything and you have to. I always say you got to know your numbers. You know, you got to know your accounting numbers, your P and L, your profit margins, your labor costs, your expense costs, how much it costs to operate every single day that your doors are open. You got to know all those numbers. Who's your

target customer? How are you attracted to them? What attracts them the best? I joke, it's like having a baseball card. You know, like when you're a little kid, you love baseball cards. You knew all the stats of your favorite players. That's the way a business owner has to be. Gotta know their numbers. And so few really are.

It's shocking to me how many business owners, entrepreneurs I'll speak to, and they're not even aware where their actuals versus their goals are for the year, you know what their net profit is. It's quite shocking. I get a spreadsheet every single day at 430 in the afternoon. Just so I'm not making this up, I'm literally putting this on the screen to show you that I'm not here.

This is my staff. I get something like this at the end of every single day showing you every line every company everything there's like Massive spreadsheet what all those call I get that every single day between 4 30 and 5 p.m So I know what my companies are doing every single day And when the goal for that is just to ensure that some specific number column isn't jumping out to you that there's a trend exactly That's all I'm looking for is a bad trend a good trend or a bad trend as a leader I need to see problems before everybody else does.

It doesn't hurt to have a little bit of a radar detector. What are some of the pivots that you've been implementing for your many businesses during the pandemic? Is there a theme or some go-to standards that you have? The theme is that you better have repeat customers. That's number one, because you're gonna dig down and if you have a lot of customers, they're gonna come back.

And you might have to pivot and alter what you're doing. You gotta stop thinking about what it is you sold pre-pandemic. You gotta think about who's your target customer and what else you could sell them. That's the pivot. The problem is most businesses don't manage their money well. I found that people that don't handle

their personal finances well, don't manage their money well. I found that people that don't handle their personal finance as well, don't handle business money well. So the same people that's business struggles struggle, have been struggling with personal finances their whole life too. That makes a lot of sense. Bad habits carry over. Yeah. In other words, if in your personal finances, if you're used to creating a

reserve account, you probably do that in your business account. Now, obviously if you own a restaurant, disregard everything I'm saying. If you own a gym, I mean, some things, clearly I'm aware that Armageddon hit, and I don't wanna downplay that. But other than that, your business has to be resilient. You have to have client concentration.

You can't have one or two clients paying all your bills because if you lose one of them, you're done. You can't have one or two clients paying all your bills because if you lose one of them, you're done. You can't have like one line of services providing such a huge amount of your profit. Every year, you got to kind of figure out a way to kind of diversify that a little bit, expand it, offer a niche off of it. Whatever it is, you can't, you know, we're old enough to know crap happens. Good business ideas seem good, but about every five years, an idea that you thought was really good

is no longer around. I mean, Blockbuster Video looked like a really good idea for a long time. Circuit City seemed like a pretty good idea. And we can go all the way down, businesses that look good, taxi business looked good until it wasn't. You know, hotels look really good until Airbnb

In other words, you have to say to yourself what can happen because in this day and age, you know innovation happens much faster Well, that's what you're describing is essentially the need to constantly every day innovate and poke holes in your business model Absolutely, you have to know that your survival is promised to no one. So you have to constantly, you know, you got to build a moat around your business. And that means you want to have more demand for what you have than you can provide. You literally need to have like something

that is very demanded, you know, and that requires great marketing, it requires a true competitive advantage. There needs to be a very obvious reason why people are buying your product and or service. If yours isn't, then you're going to be out of business. You don't have that unique selling position. I mean, business is really, really simple. It's extremely simple.

You create something that another person wants, that you can sell to them, and the margin is profitable to offer it. But the day you can't make enough profit to offer it, where it stays intriguing, you pay your bills, you're out of business, where they stop wanting what you want, or you can no longer sell it to them, I mean, businesses go out of business for the most simplest reasons. You know, barring litigation, they go out of business because you don't sell enough of your products or services to stay in business. I mean, that's it. JCPenney, Circuit City, go all the way down the line, Blockbuster Video.

Not enough demand for what they previously had a demand for, and then they close their doors. So we're living in this world where so many people, it's so popular, talk about mindset these days and having the right mindset and how that is what will make you successful in business or as an entrepreneur. I love that you don't believe that mindset

is the only thing that drives success. I mean, listen to me, I'm a mindset guy to a per, I mean, I was a division one athlete, but I could wake up every day and do affirmations till I'm blue in my face and I would love to sing the national anthem. I don't have the talent to sing the national anthem. I could want to be a great golfer and I could lay there and visualize the perfect swing all day long

But I think I might need to take lessons. Mindset is fine, but mindset without talent is kind of a waste of time. So, I mean mindset is great to take something you already have a proficiency in and maximizing. It's like Jack Nichols, a great golfer said, hey, I never hit a golf shot that I didn't first see in my mind. Well, that's great. That's great mindset. That's great visualization.

Now, it didn't hurt that he had probably won the best golf swings to ever happen in his peak. So yeah, that probably took him to the next level over his competition, but there was a great deal of talent. Tiger Woods has got incredible confidence, but that self-confidence is through endless that he started swinging a golf club at age two. He had three amateur championships. I mean, in other words, it's great, but I think it has to be tied to talent and hard

work. It's the octane. It's the power booster, but you still got to have a car with an engine and a steering wheel. And it's great. And I do think it's hard to achieve at a tremendous level with a bad mindset. So I do think mindset is if you're negative and you have no self-confidence, yeah, I don't think you're going to be successful.

I think it's really an uphill battle. You're going to stumble into it. Let me guess. You'd rather get a root canal than shop for car insurance. Yeah, you're not alone. It's a total headache. Quotes all over the place, confusing coverage, spam calls from companies you've never heard of. You'd think it was designed to be that frustrating. It doesn't have to be. Jerry does car insurance shopping differently, and it's not just another comparison site. It's comprehensive car insurance app that does the legwork for you, start to finish. Jerry simplifies things by handling the entire insurance shopping process in one place.

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Not all drivers find savings. Confidence created. I asked you to try to find your passion. You know, so interesting, early in my business career, I asked you to try to find your passion. You know, so interesting, early in my business career, in my 20s, I was given a great opportunity as an equity partner to run a group of radio stations. I had the talent, I had the ability, I had the skill set. My mindset wasn't right back then.

I wasn't aware of mindset, the impact of mindset. I wasn't confident. I was doubting myself all of the time. And it was a massively uphill battle. It was much harder than it had to be. Let me just say, I think mindset is the difference maker. But I do think you have to have, you gotta have a great work ethic. You gotta have a proficiency in something.

I mean, I think that's critical, but I'm a visualization guy. I was an athlete. It works. There's no question visualization works. There's no question visualization works. There's no question affirmations work, again, tied to an area where you have some level of giftedness. It works.

I believe the law of attraction is as sure as I believe in the law of gravity. So I absolutely believe it works. But all of that works best in an area of competency. The example, think about this for a second. Okay, we've got law of attraction or affirmations or all those, but if I am ignorant enough to say, okay, I wanna be a basketball player, I'm five foot eight. You know what I'm saying?

I mean, that's a highly unrealistic. I think, you know, the universe is allowed to say, okay, please, I really wanna give you what you want, but let's try again. Or I think the universe is able to say, you know what, you are gifted, but sadly you don't know what you're gifted in yet. So let's find what you're gifted in

and then let's focus on this stuff. I mean, sometimes the most important thing is getting a client or a person to find out their area of giftedness. I love mindset and I do all the traditional things because they all work. But I find that mindset works in my area of giftedness. Some of those moments to discover your gift come hard won,

like you getting up on a stage at a comedy show. You know, I have one of those personalities where I really, I'm one of them, like me or don't like me, I could give a fat fly and rip on the same way, you know, all the time. But my friends are like, Sean, you're very, I do observational humor. I don't even try to be funny.

Like I can sit in an amusement park and just make observation of people just walking by and you will cry laughing. So my friends are like, hey, you need to do standup comedy. And I said, well, I'm not gonna do it in my town. It's kind of like too small. I said, I would do it in a major city.

So like, if I'm gonna do this, I want it to be like worth my time. I really wanna, if I'm gonna get embarrassed this, I want it to be like worth my time. I really want to, if I'm going to get embarrassed, I want to do it at a grand level. So yeah, so I did, I went to a clash of the comics in a major city where they do it like once a month and you've got to sign up. There's like a waiting list and you sign up and then you do five minute routines. And I ended up being a finalist. So it was funny. I did it once as on a bet, But you know, I think as an entrepreneur, you got to have that self-confidence. I mean, you pitch your business for investors.

It's not much different. Yeah, but it's about taking that leap, like putting yourself out there. And the more you take that leap, the more stages you jump on or comedy contests or whatever it may be, the more you really get to trust yourself. Self-confidence. There is a quote, Donald Trump. Whether you like him or you don't like him, I'm not getting into that debate. That's a moot point. But he made a comment in the mid-1980s.

I'll never forget it. It was on, I believe it was like the Phil Donahue show, and somebody from the audience said, you are so cocky. You're so arrogant. And he said, ma'am, show me a man with no confidence, and I'll show you a loser every time. Wow.

I remembered it. I mean, I was like a teenager then, like 15. And I remember 35 years later and I remember it. Ma'am, show me a man with no confidence and I'll show you a loser every time. Wow. It really is the difference maker though. I mean, there's no doubt it's that intangible

that when you have it, people are buying what you're selling, people are trusting you and they want to join whatever your initiative is. Yeah, you know, typically you're the, you know, the lead person. If you don't absolutely buy into what you're doing, nobody's going to join you. And I've had people join my startups and I asked them, you know, I couldn't pay the most money, you know, why? And they go, I could tell you were going to succeed. They're like, I knew it was going to be successful.

You had that personality. I absolutely knew this is something I needed to be a part of. That's got to be one of the most meaningful things, developing a startup and starting to bring people on and then seeing the company succeed and seeing them gain this value. That must be amazing. No it is. I have a big, you a big Christmas party every year. And I joke when I'm driving there with my wife,

this is my favorite time of the year with anything to do with my team. And I say, what blows me away is the amount of money that people in this room make. And this is traditional. This isn't multi-level marketing. I'm not criticizing all of them, but I mean, I have brick and mortar,

real life businesses, customers, payroll, the whole nine yards. And I have countless partners that make significant six figure incomes that had never made anything close to that in their life. And then they partnered with me and, you know, they're now they're making more money than they've ever made in their life.

They have flexible schedules. They're doing something in their true area of giftedness because I make sure they stay in their area giftedness. So yeah, that is the most rewarding thing is when you create wealth for other people. How do you help them find their area of their gift? How do you help them identify that and get in that right role?

I mean, the key is that generally they are good at something. Okay, I don't bring on a partner unless I think, normally though they have an expertise. That's typically what I find. They understand an industry really well, better than I do. I understand there's potential to make money, but I don't necessarily understand the industry per se. So I partner with people that understand industries. Now what I look at is, do they have an incredible work ethic? Are they honest? Can I trust them with the checkbook? Do they really want to have a better

life? So I look at the intangibles. I like people that are crazy smart. You can't hide stupid. You can't fix lazy. So there are certain things I look at. And when I find that, then I bring them in as a partner. Typically what I bring to the table that they don't see in themselves is I know that they could lead and they've yet to have the opportunity to lead. So what I do is I bring them on early and have to work with them maybe on the leadership

side, but they have the talent, but they've had it in like an employee role somewhere. And so I got to get them to kind of come over to getting paid based on what you, you know, what you produce. And make that leap, but they've got to trust you to make the leap, I'm sure. Yeah, yeah. And typically I bankroll it to the point where I'll match a percentage of their salary. I'll normally like, I like to create a little bit of pain because I want them to make a sacrifice and I want them to have to do well.

But yeah, they have to believe in it. That's for sure. So Sean, where can everybody find you? How can they get a hold of your podcast and more of your business tips? Yeah, great. I always give away a free book on my website, SeanCastrino.com. I think right now we got my first book, the eight unbreakable rules for business startup success. That's free on there.

You can get that. And then my podcast is the 10 minute entrepreneur podcast. I typically interview business founders. I interview more founders, any other podcasts on the planet, period. So that does extremely well. 10 minute entrepreneur podcast and go to my personal website.

You can get a free book and you can always find me on Instagram. Sean, thank you so much for your time today. I know you are a busy man running many companies, so it means the world. No, thank you so much for having me on the podcast. All right. Hold tight. We'll be right back. I hope you love meeting Sean as much as I loved getting the chance to interview him so much knowledge and definitely taught me some things

that I had never thought about. So I'm only gonna do one question today because I talked so much in the beginning of this show that I don't wanna drive you nuts. So here's a DM I received on LinkedIn today. Hey Heather, two quick questions for you. Do you manage your own social media or do you have someone do it for you?

Do you make use of a social media management program for social media and which one is it that you use? So this is an interesting question. And first of all, I believe in testing things. So I'm always trying different tools. I use Hootsuite to schedule. I use Canva to create graphics. I test different programs all the time.

I use Shield Analytics on LinkedIn to analyze performance on my content. I use Iconosquare on Instagram. I am always challenging myself to learn and grow. And the way that I do that is by talking to different people to see what works for them, but also just researching things online and just giving it a shot, right? You know, some things work well. Shield for me with LinkedIn is amazing.

Iconosquare for Instagram is amazing. But then, for example, this week, I'll tell you, I was so flipping busy. I don't think I used any of my tools this week. I probably posted, I mean, 20% as much as I usually do. So there's an ebb and flow for me in that, listen, I have someone who manages my social media for sure. She's amazing and love her.

And she knows me well enough and I trust her enough that she can just go and post daily for me and it'll all be fine. However, my social media does best when I'm posting because it's me, right? So I definitely challenge myself to post every day, but then there's weeks like this week that it just, it's not going to happen. It's not feasible and I've got to cut certain things out. So I just really did not manage social at all. She took it and I'm sure it's going to be just fine, but it won't be as strong as the

days where I have time on the fly to post different things. So number one, social media for me was an investment in myself that I made four years ago when I was still in corporate America. And I share that with you because I don't want people to think that I do this on my own and I just started doing it last week, right? This is four years in, which is a sizable amount of time. Four years is a lot. And back then Instagram and Facebook were so much easier to grow. They're so hard to grow now. I have like zero growth in the past year on both of those platforms, but LinkedIn for me is exploding. It's so organic and easy to reach people. Definitely go all in on LinkedIn if you

haven't. I say this all the time, but definitely do it. And Gary Vee is the one that told me a year ago that I needed to post more frequently on LinkedIn 10 to 15 times a day. That's my goal. I definitely don't always hit it, but frequency is really important. Once you develop an audience, but it all starts with four years ago, I started posting once a day. And back then I wasn't being my real authentic self

because I still worked in corporate America. I was seeing everything through the lens of is the GC gonna come after me? Is the CFO gonna be pissed I talked about this? So I was super vanilla, no haters. I would do posts like the top three ways to ask for a raise in Q4. Really basic stuff. Where today I might just post, I posted a picture or a video of me working out this morning saying, listen, this week was a grind for me and I really didn't work out much and didn't take care of myself because I had to kill it in these speeches and attend these meetings and whatever, whatever.

But today I'm back at the workout. I'm back reinvesting in me. It's a completely different kind of post that four years ago I wouldn't have done. So I guess my point is, yes, I think you need to invest in yourself. Yes, I think you should hire someone if you can to make sure you're consistent with social media. But then yes, you need to show up on top of that and you need to bring your unique fire to the marketplace and who you really are,

because no one will ever be able to do as great a job being you as you will, but definitely make the investment. And as far as tools go, they are coming fast and furious. It's super important to keep testing new things, checking out new things and continue to innovate for yourself. The only way you're gonna know is if you try.

So I will leave it at that, and I can't wait to see you next week. So please, if you can, rate and review the show. It helps so, so much. And if you post, please tag me. I will always repost. I appreciate your support more than you know. Can't wait to catch you next week.

I'm gonna make a run over again. I decided to change that dynamic. I feel like that last time. I couldn't be more excited to pour out what you're gonna fear, start learning and growing. Inevitably something will happen. No one succeeds alone. You don't stop and look around once in a while.

You could miss it. I'm on this journey with me.