#153: The KEY To Building Your Own Brand With Tony Whatley Founder of 365 Driven
4 Nov 2025 · 51 min
Podcast episode (#153) hosted by Heather Monahan featuring Tony Whatley (founder of 365 Driven). Tony recounts his trajectory from a working-class upbringing and a mechanical engineering/corporate career in oil & gas to building multiple high-traffic automotive communities (ls1tech.com, PerformanceTrucks.net), selling them (exit in 2007), and later pivoting after a near-fatal 2015 racing accident to launch 365 Driven (2017), write the book Side Hustle Millionaire, and teach entrepreneurs about mindset, personal branding, marketing, and persistence. Key specifics: first side business started in 2001; sold those companies in 2007; managed projects worth $100–200M in corporate roles; had a severe racing crash in late 2015 that catalyzed his shift; launched 365 Driven in 2017; maintains a website at 365Driven.com and an online business that once earned about $100,000/year.
Questions this episode answers
365Driven.com
Side Hustle Millionaire
2001
2007
Late 2015
Chapters
I had to become the right person to carry that book. The book itself, the knowledge itself was something I had for 20 years in my mind through trials and tribulations and experience. But I had to become the right person to carry that book. And I think that's where most authors fail, is because they can write the book because they got the experience and the know how, but they don't ever become that right person to carry that book. And that's the thing that's missing from almost anything with podcasts or books is how do you build that personal brand? How do you gain that courage to do that?
Come on this journey with me each week when you join me, we are going to chase down our goals, overcome adversity and set you up for a better tomorrow.
I'm ready for my close up.
Hi and welcome back. I'm so excited for you to meet my guest today, Tony Watley. He's a best selling author of the side Hustle Millionaires. His book which went number one on Amazon immediately as soon as it hit. But this book isn't just fiction, it's based on Tony's actual story. Tony once led a successful corporate career for over 25 years. Sounds like someone I know, but that is less interesting than the side business that he created which generated millions in profit. As an active entrepreneur himself, he still owns a few businesses, but his real passion is teaching entrepreneurs how to start, scale and sell their businesses within his podcast and consulting brand, 365 Driven. Tony, thank you so much for making time to be here today.
Hey Heather, thank you for this opportunity. It's been a long time. I've been waiting to catch up with you. I've been enjoying your content as well. And here we are today and I can't wait to give some value to your audience.
Well, Tony, let's first of all, I love your story because I love that we both started in that corporate America hustle and finally found a way out. Will you give us a little bit of background and in what happened for you?
Yeah, for me growing up, I grew up lower middle class here in the Houston area. My parents are both hard working parents. My mom worked in the public schools as a cafeteria worker. My dad was a U.S. marine Vietnam vet. And after that he got out and worked in the chemical refineries. So we didn't grow up with a lot of money. And we always hear about, I know you're going to hear about this and agree with it. Hey, you got to go be a doctor, a lawyer or an engineer if you Want to make six figures. So that was always the goal. I was actually the first person in both of my family sides to go to the university. I had to put myself through school by working labor as a welder and a pipe fitter and waiting tables at restaurants and things like that. And that's just who I was. So when I started to get into the corporate, I spent seven years in school, working full time, going to school at night. I was sleep deprived, depressed, and really the college years were terrible for me just because I was just not had bad relationships. I was broke all the time. I was stressed out. Actually had more gray hair in college than I do now. And I don't dye my hair, which is kind of weird. But stress does that. Sleep deprivation does that. Bad diet, 99 cent double cheeseburgers do that to you, right? And I just was really intent on pursuing my corporate career as a mechanical engineering degree. And I got into the oil and gas industry here in Houston, which is the capital of that industry. And I just wanted to climb. I just wanted to climb. And I was a very aggressive type climber because I'd already been working in the refineries on the tools. So I understood a lot about this stuff when I finally got to my degree. So, you know, we're comparing to people that graduated, you know, 21. I was graduating at 27, 28 years old, but I had a lot of field experience and so I was ready to climb a lot faster. And I got tired of telling people telling me to wait my turn and you're too young to be a manager and all these things are always trying to hold you back. And you're looking at the people that have the nicer office or the nicer cubicle than you do. And you're trying to assess, like, how long is it going to be before they get out of that seat and I can actually move into that seat. And you're looking at like five, six years on average to get to each level. And I was like, I don't know if I want to wait that long. So I actually started my first business in 2001 because I have a passion for cars. I said, man, if I'm going to teach myself some things, I'm going to go build a little business and learn how to do things in accounting and marketing and make some decisions and take some risks because I had bills paid, you know, with the engineering job. And so I started a online community for racing cars called ls1tech.com and that grew into the largest of its kind on The Internet. We had over 300,000 registered members and General Motors performance cars. So my sponsors, my advertisers were like Cadillac and Chevrolet and Pontiac and things like that. And we took that same business model and I built Performance Trucks.net, which grew to 280,000 registered members for the racing truck guys. So I was able to duplicate that twice. And I sold those companies in 2007, which went for millions of dollars, which is kind of the basis of that book you just mentioned, Side Hustle Millionaire. So, in a period of six years, able to start as a side business and grow those and scale those and exit those. But I was always driven also with the career, Heather, because you and I, we had that career. We had that drive. You were a C suite. You know exactly what it takes to navigate through that. And it was very easy for me because I had that confidence. Another subject, you're an expert on that. I knew that I always carried that parachute around with me that I could deploy at any time because nobody at any job was going to abuse me. I was definitely the hardest worker and putting out the actual results. But I had a lot to do with the confidence I was getting externally from those office settings. And that's what I did. I also had my mom's voice on my shoulder the whole time about the corporate career. Like, don't waste your degree. Do these things. And honestly, I'm a competitive person. I'm sure you are as well. And we just want to see how far we could go. We just want to see. Just curiosity. Right. So that all changed in 2015.
So what was that moment that really.
Changed it for you for 2015? We were always. We're already going through a oil and gas industry decline. I've already been through three of those downturns in that industry. It seems that cyclical. It comes around every seven to eight years. We started to do layoffs. I was managing projects worth 100 to 200 million dollars and had international projects. I was working out of Africa and France and England and just doing a lot of international travel. I was rarely anywhere around. Like, it literally got to be. My friends thought I was an international spy or something because I was never around. And sometimes I'm off the grid because they don't have Internet in Africa in some places. Right. So you start thinking about that, and I see the decline. I started to see the corporate people start to take advantage of some of their employees and also do some really kind of unethical things in the management ranks where I was at that Level where I was having to make those decisions and put my name on those all of a sudden, and we're starting to lay people off because they're older and they're making too much money and it's starting to get into ageism. And I didn't agree with that because I didn't experience that because prior to age 40, and I think you'll agree with this, it's pretty easy to find a job replacement when you get laid off because you're really at that point where you have a lot of experience and you're probably undercompensated. So you're like, hey, cool, like if I get laid off, you know, three or four months, I'll have another job, no big deal. But when you start to get in your 40s and you're making multiple six figures and people are starting to lay you off because you make multiple six figures, no matter how good you are, you're a financial asset thing that they just like to push out the door. And I started to see that. And I know this is highly illegal, but those conversations do go on at that HR level, just not in writing. And I was like, you know, I don't know if I could be in this part of this conversation anymore. And so I was already kind of in that negative decline of that. But then I actually had a car accident racing cars late in 2015. And the thing is, I was racing 1,000 horsepower Dodge Viper trying to set a national record and a quarter mile drag strip. And everything was going well until the top of third gear about 130 miles per hour or something in the rear suspension broke and the rear wheel is essentially steering the car instead of the front wheels. And so I grazed the right side wall. And then as I started thinking that the worst was over, I started to slow down and I came back off of that wall. And then the car went hard left and now I'm aiming at the other wall in the left lane. It's concrete wall. And I'm at 130 miles per hour doing quick mental calculations that I got bad odds at surviving this. And in that moment I even said to myself, well, here I go. I remember that as clear as day. I just remember saying that, well, here I go. And here's the weird thing about that, Heather, is that going through that, it felt like an eternity when I was approaching that wall. But the weirdest thing is that I felt an overwhelming sense of peacefulness. You would think there'd be fear or some kind of screaming or just something like you see on the movies, but it's not like that. I just felt an overwhelming sense of peacefulness and warmth and it was literally let Jesus take the wheel type moment for me. And I remember hitting the impact and the airbags deployed and the cabin filled with the white powdery smoke. And it's really dark at the end of the track and the lights are flickering and off. I could hear the entire car coming to pieces and glass breaking and carbon fiber and aluminum just ripped apart. The wheels are coming off the cars. And I just remember surviving the impact and thinking to myself, stay awake, stay awake. Because I didn't know if I was injured or not. I just knew that most people die from the fire, not the impact, because all the fluids spill out and everything's flammable. And I just remember, just, hey, when this car comes to a rest, I need to get out of the car. I just need to stay awake. Just stay awake. And it felt like it was sliding forever and finally came to a rest. I had to pry that door open because it got smashed in on that side of the car. And I just got out of the car and I took my helmet off and I'm looking at the wreckage. There's literally wheels off the car, every single panel. This, this car is destroyed. It's smashed into the front up to the windshield. And I could hear the ambulance coming. I hear people sprinting up the track to see what happened. I hear four wheelers approaching and. And they put me in the back of the ambulance and I'm sitting there looking at this wreckage of this car and the paramedics inspecting me and asking me questions to see if I was. Had a concussion or not. And I was answering everything really clearly. And then at the end of her inspection, she goes, can I tell you something unusual? And I was like, oh, great. Like, here goes. Like, what's she going to tell me? My leg is backwards? I got a rib poking out my back? Like, I'm thinking the worst, right? Because it'd been calm up to that point. And she just said, no, it's, it's remarkably calm. You're very calm. I've answered all these questions. You're really calm. Your heart rate isn't elevated, you don't have the adrenaline shakes, you don't have the shortness of breath, you don't have the cold sweats. Like, you're just calm. And I said, I am calm. It was just as calm as when I was approaching that wall. I felt, felt it. I just felt calm. And I was looking at the Wreckage. And later on I started to realize, like, what was I thinking in that moment? Because I got asked so many times and it was a series of questions, pretty logical questions. I was looking at the wreckage thinking, why am I still here? I could have died right there. Why am I still here? And then the next question logically from that is, well, if I would have died, how would I been remembered? And then you start to think about people that you've known that have passed away in recent or maybe in the same situation. How were they remembered? How did that compare and was that enough? And for me it would have been rich guy, nice guy, cool cars, you know, gone too soon, right? And I said, does that really sit well with me? Like, do I want to be remembered as rich guy with cool cars, nice guy, successful? It felt really superficial. I felt like as someone who's a high achiever, that someone has always pushed themselves to do more. I felt like, kind of like the neon sign you see blinking over my shoulder, I felt like that it was a glaring neon response that that's very superficial and you didn't try hard enough. Like there was more that you could have done. And so that's what I went on that mission. I was like, I needed to go do something to create impact. And I know that's a big buzzword nowadays, but that was really what was going through my mind. How am I going to go make impact in this world? And I went and I left that career and I didn't go back to it. And people thought I was crazy. Like, how do you giving up 20 something years of experience and you know, and all multiple six figure income, you got other people that'll hire you as a junior level executive at smaller supplier companies and stuff. And I said, I said I'm not interested in that because I didn't know what the impact meant to me. I just knew that I needed to do more than go work at a corporate job and waste all my hours and my time and my dedication and talents in some company that didn't care about their people anymore. Industry that didn't care about their people anymore. So that's what I did. And really I just kind of left and didn't do that. I just kind of left.
Tony, that's a big leap. Obviously, thank goodness that you are okay. And the whole experience is just so surreal to hear what you went through. You know, I got fired, that's why I left. But agreed with everything you said. When, when you reach a certain level, you see that things are going on. It's just not right. And it's hard to sit and just watch that and collect a paycheck and be a part of something like that. Couldn't agree more. However, didn't you struggle with, even though you had had this near death experience that wait, am I really going to just stop working here and take a risk going off into the unknown? How am I going to pay my bills? How am I going to move forward?
At the time, I did have an online business that was making about $100,000 a year and that's something I'd had for 15 years. So I know that was pretty stable and I knew that that would at least cover my bills. And also I'd put myself in a financial situation where I didn't have to work for a while and that's fine. I had to put in a lot of work, exited the companies, had different investments going on. So I positioned myself into that. But I didn't think I was ever going to leave and go with that. I was really intent on being the CEO of these major oil and gas companies. And I know that's within my capabilities. It was just a matter of time and execution to achieve that. But it just didn't sit well with me. Because even if I had made an executive role at those companies, would that really have created this maximum impact that I had within my potential capability of doing? And the answer is no. I may have impacted the shareholders and the dividends paid out and landing some large contracts and things like that and big numbers. I mean, it's. That was my entire career and I understand all that kind of stuff. I love the numbers game and I love the game of business. But it just, I think, what is the impact? What does that really mean to me? And does that mean I need to go create a non profit or go on a philanthropy mission or just something like what does that even mean right when you hear that? It's a really deep question. And most people unfortunately don't understand what their purpose is or anything like that. When you ask them, most people say, oh, I just want to take care of my family. And you know, that sounds very honorable. But the problem is that that answer is so common that it gets repeated back and forth by people who aspire to be average, that don't really want to confront what their true potential is.
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Just want to take care of my family. And it sounds great. And you're supposed to stop the conversation right there. When you challenge somebody about the purpose and they give that, that's a wild card. But when you ask someone like me or ask someone like you, Heather, like what is your purpose? And they say family, I don't say that. I say, no, that's your duty. Taking care of your family is your duty. That's not your purpose. Your purpose is a lot bigger than your immediate family. You may not think it is, but, you know, may not believe that it is, but it is a lot bigger than your family. So to me, family's always been duty. So what is my purpose? What is it bigger? How am I going to go achieve that? And I said, well, it took me the next two years. I launched 365 driven in 2017. But the next two years I was kind of on that soul searching mission and I was taking some consulting gigs and doing that and running my business to make the bills paid. And I was experimenting and I started to think about how am I going to impact the most amount of people as possible. And it all goes back to my childhood. And even the clues leading up through my entire career is I was the kid that when my mom would go grocery shopping when I was a kid, I would run to the magazine racks and she would go shopping and I would read my car magazines because that's what I was into. And then I didn't have any money. So I started noticing in the quarter mile these other magazines talking about money, fortune, entrepreneur, success, like Forbes. I said, well, maybe if I read fewer of these car magazines and read some of those I'll figure out how to make money. I'm 12 years old. Think about how weird this sounds now. So I got a subscription to a couple of those magazines with my car magazines, and I would read those cover to cover. And I didn't understand what I was reading, but I just knew that maybe I could unlock some knowledge about that kind of stuff that I learned. And so maybe within a year, I started realizing what they were talking about. I started putting the terminology in order. And, okay, I kind of get what that means, But I was a kid, you know, and I didn't understand all the details of it, but I was the kid that was knocking on doors, washing cars, mowing yards, walking dogs, whatever I could to make money, because that's how I paid for my skateboards and video games and BMX bikes, because I didn't have allowance, right? And so I said, I've always been fascinated with cars and business, and I always think of business as, like, a game, and there's rules and scores and all these different things. I said, well, maybe that's what my purpose really is. I'm going to go impact, I used to say thousands of people because I didn't believe in millions, but now I say millions. But my purpose now is to go impact the generational legacy of millions of people by teaching them confidence and business principles. Because that's what got me the lifestyle that I have, the cars that I had. And so everybody knew about that stuff. So let me teach them how to get their own. And that's what it became. And I'll tell you, even then, I hesitated getting into the personal development space because you and I know there's a bunch of frauds and things out there, and people are selling stuff they've never achieved themselves. And I had a really private life, and I was really insecure about things, and I hid from the cameras and I had stage frights and all these things that I had to get over. But I didn't even want to get into that space because I didn't want to be lumped into the same group as those people. Like most of them, there's a lot of good ones out there. We know that now. But from the outside, it's probably 75% are kind of like you're skeptical, and the rest of them, you're like, okay, they're good.
Tony, that's such a massive shift over just those couple of years from 2015 to 2017 for you. Tell me how when you finally understood the purpose that you wanted to live out in your Life and this passion and commitment you had to helping others. What were some of those first steps that you took to get the company365 up and running?
This is one that I think most of your listeners will relate with. We all have a book inside of us. We all have a book. We always think about, hey, I want to write this book. And I had this book in my mind for about five years on how to start businesses and help people that were early level entrepreneurs. And over the past 20 years as a business owner, I've helped some of my staff members build seven, eight and nine figure businesses for over 20 years. And they were always telling me, tony, you should be teaching this. But I had a bunch of convenient excuses. I just said, I'm busy or I've got businesses or I've got a family, I've got this career. And really it was just avoiding making myself public. Right. I had a very kind of comfortable private life, excelling in entrepreneurship and corporate at the same time. But I didn't have to be on stage and I didn't have to be on camera and I could do it all in the background and it was fine because I had those insecurities. I grew up half Japanese and a largely country town in Texas and I experienced racism a kid. I have skin issues where I'm covered with vitiligo, so I'm covered with white spots. So people used to make fun of those things when I was a kid. So I understood that I didn't like being in front of the camera. I knew and I just said, well, shit, if I'm going to make a impact, I kind of need to get over that. I need to figure out what I need to do to get my message out there. So I really started admitting this recently about the book. Probably in the last three months, after three years it's been out that it was the most cowardly way for me to get what was in my mind out to the masses because it didn't require me to be on camera or recorded voice, which I didn't like at that time. Or you know, having to put myself out there. Said, man, if I could just write this book, maybe I can be one of those famous authors that nobody recognizes. And then at least what was, at least what's inside my mind will be out there. And if it does good, great. If it does bad, nobody will care because that's just the way it is. Right? So here's the crazy thing about the Heather because you laughed and it's so true because we all kind of process this. Right? We think the book is the. The gateway. And it is. It could be. It could be the key that unlocks doors that we don't even see, that we don't even know exist. And that's what happened for me. But I'm writing this book, and I hired an editor that's helped other people that become successful writers, and he's giving me feedback, and he's reading these chapters each time I finish a chapter. And he's like, man, early chapters. This is going to be a good book at Canardill. Cool, thanks. And I'm still going probably chapter four. He's like, man, this is going to be a really good book. I think this one's going to launch really well. And they're probably going to want to interview. You're probably going to be on podcasts or the radio or TV or. I'm like, oh, crap. There's that thing I was hiding from. It's coming back to confront me again. So I was like, man, I can't keep hiding from this fear of doing that. Let me get past that. Let me solve that. So I do what most people do. I go on Google and I said, how do you get over stage fright? Or how do you get better on camera? And they say, hey, join toastmasters. Hire a speaking coach, hire a video coach, whatever those things are. And so, okay, I'm just going to go do it. I'm just going to hold my nose. I'm just going to go do it. I know it's uncomfortable, but I realized halfway through writing my book, this is in late 2017, is that I had to become the right person to carry that book. The book itself, the knowledge itself, was something I had for 20 years in my mind through trials and tribulations and experience. But I had to become the right person to carry that book. And I think that's where most authors fail, is because they can write the book because they got the experience and they know how, but they don't ever become that right person to carry that book, to be the biggest cheerleader of that book and to campaign that book and to spread the gospel of that book. And that's the thing that's missing from almost anything with podcasts or books, is how do you build that personal brand? How do you gain that courage to do that?
Yeah, that's the hard work, right? And I totally relate to what you were just saying there. I remember hating hearing my voice at first. You know, the first time that I heard myself as a guest on a Podcast. I remember the first time I saw a video of me speaking, you know, at a large event. I cringe when I watched myself. So I totally relate to you, and I think a lot of people do. But the key, for me, anyways, was even though I didn't like it, even though I didn't think I was good, even though I didn't like my voice, I just kept going. And over time, you start to, quote, unquote, find your voice or whatever, you know, make less mistakes or show up as that real version of you. And it's. To me, it's been really that key of stepping into the unfamiliar, stepping into the uncomfortable, even when you don't like it, even when you don't like how you sound and just keep showing up. Was that sort of the same way, how it panned out for you?
It was a terrible, terrible startup, just like you said. Because here's the thing. In our minds, we think we're going to be better than we are. And even when you're recording those first videos, you feel like, oh, that was a good one. And then you go watch the replay, you're like, oh, God, this is terrible. But to give you a perspective of how much I did not enjoy this, I was doing this consulting gig. So sometimes I had a tie on, I looked nice, and I said, okay, when I get back to the car, I'm just going to do a video every day on my phone. I'll just put it on the little dash holder, and I have a message maybe I wanted to talk about, because I listen to podcasts, read a lot of books, so I always have a lot of ideas. And I said, okay, I'm just going to do a video. And here's how scared I was. I would sit in a parking lot, and if somebody walked by, like, two rows over, not even near my car, and I thought that maybe they could see me, I would just turn the camera off because I didn't feel confident enough to do those videos. I was that scared about doing that. I felt weird about it. Right? That's also with men, especially when guys do selfies and videos. Other alpha dudes kind of make fun of guys like that. They're like, oh, look at that. They're acting like a teenage girl. You know, and initially, when you're in that group, you're kind of like, yeah, they're acting like teenage girls selfies. Like, no, no man does that. And you start to realize that the people that are making impact, the people that you truly admire, like we talked about before, Fired up. One of my mentors is Ed Mylett. Those guys are as alpha and jacked as it gets. Highly successful. What are they doing? They're doing selfies. So you start to have this weird mix of people trying to lead you the wrong way because they're uncomfortable with it, equally uncomfortable with it. They don't have the courage to do it. But the people that you admire making real impact are doing the exact things that you're trying to be afraid of. So it was really awkward to do those original videos. And I said, you know what? I'm going to push myself because, yeah, you can go to Toastmasters and it's one meeting a week and you can raise your hand and you might get two to three minutes in front of the room once a week. I said, well, I'm learning all this stuff, but I have no stage to stand on, so why don't I just start practicing the things I'm learning from public speaking and just put it in the video? And that's what I did. So the first year, the 2017-18, I did a video every single day on social media. No matter how bad it is, I'll do 10 takes and I would just pick the best one. And eventually I got to do them where I could just do them one take, and I got confidence. But it's just repetition. And you're not going to be able to skip this. If you're listening to this or watching this, you're not going to be able to skip that. You only get better from repetitions.
Oh, so, so true. And I wish I had understood, understood that more. You know, earlier on, it took me finally getting some positive feedback from people that, you know, read the book or whatever or heard the podcast and said, wow, you know, great voice. And I'd say, really? Really? You think so? It was so eye opening for me because when you're showing up as yourself every single day, you're not noticing that you're getting better, you're not noticing that you're standing up a little bit more confidently, that you're sharing things you wouldn't have been able to before. So sometimes it does take those people outside of your innermost circle to tap you and say, you know what, that you're really getting good. And then it's so exciting when you hear that.
It reminds me of a story. This is a good one that people relate to because I actually. The previous corporate job, right, it had been two years after that on LinkedIn, where you and I like to hang out a lot. Somebody Saw my videos, one of my former colleagues, and he reached out to me, hey, man, I'm enjoying your videos, and you got a good message. And he's like. So he said, man, I don't think I could ever do that. Scary. Like, how do you, how do you get the confidence to get on camera? That's. I don't, I don't think I could ever do that. And this guy's pretty confident, pretty successful for himself. And. And so I had to put that in perspective. So this is really going to help people. I said, hey, Brian, do you still have the same boss that we worked with? Is she still there? Yeah, yeah, she's still here. It's like, so if she were to walk up to your desk at 8:00 in the morning, first thing in the morning, said, hey, Brian, take out your phone and if you do this one minute video, you can go home for the rest of the day, would you do it? And he thought about it and goes, yeah, I guess I would. I was like, so you're saying you would do a video if it was your job description and you could have the rest of the day off? And he's like, yeah, I guess I would. I was like, doing videos is part of my job description now. Like, I don't do them because I love to do it and I have to do it. And I feel like doing it because successful people are not driven by motivation, we're driven by results. And if I'm redefining who I am and that's part of the roles and responsibilities I need to do, guess what? I'm going to do it.
That's so good. Yeah. And I love that you gave him that analogy because once you put a carrot out there, we're all willing to, at least when it makes sense to us, we're willing to step into that fear and take on the unknown. So what are some of the principles that you teach through the book and through all of your teachings that you really feel like impact people the most?
The first two chapters of that book are actually on mindset. It's about getting over the excuses that people commonly have about starting their first business. They say things like, I got no time, I have no money, I have kids, I don't have enough experience, I don't have education. Like all the. I mean, I basically made a list of all the common objections and I gave really detailed responses for each of those. So, yeah, getting over that is the hard part because everybody's got excuses. But you start to realize that for every excuse that you have, there's a million people that had the exact same situation as you that became successful because they were able to push those excuses away. The thing that we hang around with, the people that volley back and forth, the excuses, they're the ones that keep you at that level. Right. And when people ask me, well, when did you start your business? How was your Life like? Actually, 2000 was my lowest point in my life. And that was when I had a failed relationship with my son's mother. He was less than 1 years old. We were broke because I got laid off a year before that. So we were living off of credit cards and racked up about $40,000 in credit card debt. I was paying for her apartment, my apartment. I was waiting tables. When I finally got another job that paid less, My previous job, I was still waiting tables for the next two years while I was starting this company with a newborn son. Bad relationship, depressed, broke. I mean, I was so broke that I mistakenly picked an apartment that was off of a tollway. And there was times I couldn't even drive anywhere unless it was going to work to get that paycheck on that Friday, because I knew that I didn't have enough change to go anywhere. Like to go hang out with my friends. I would just stay home. So I've been there before and I realized that that's not the life that I wanted to have. And I still started a business and the business was because I needed to be focused on something that was positive and I needed an outlet and I could get books and learn and teach myself how to do Photoshop and create websites and photography and things that graphic design. I was just kind of interested. I've always been an artistic type, creative person. So I just taught myself new skills when I had the time to do that. And I practiced those things. And soon enough I was building websites for different companies and getting paid to do that, and I didn't have to wait tables anymore.
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So you realize like if you're not where you want to be, ask yourself in this moment, what are you willing to do to get out of that? You know, what are you willing to do? Are you worried about what people are going to think about you guys? I had an engineering degree, I had an Engineering job. I was still waiting table seven nights a week. Sometimes the people at the engineering job would see me at the restaurant, ask why I was there because I had a higher salary than them. And I said, well, because I'm not where I want to be right now. This is a way for me to make extra money to put away to do things that I want to do so I can achieve what I want to achieve. So I've never been worried about what other people think about what I needed to go do.
What are some of the keys? Once you get people down this path, they've got the mindset, right, that they're willing to start the business, try and test different things to see what can make them some money. What are some of the directions that you give them once they're getting up and running to grow.
I'd say that the most things that people fail at is because we leave a job, we leave a corporate job or a career that is based on our skill sets or a knowledge base that we have. So maybe you're a programmer or you're an engineer, or you're an attorney. Whatever your skill and your knowledge is, you think, like, I'm really good at this, or maybe you're compensated enough to prove that you are good at that. But then you think, I'm going to go start a business based on that same kind of skill set or knowledge base. And we already know that 50% of businesses fail within the year 2 and 20% fail in the year 1. And the reason why is because they don't understand the business process. They don't invest the same level of attention into understanding how to manage businesses. They don't understand cash flow and accounting, they don't understand marketing, they don't understand salesmanship. Thinking about it, if you're an engineer and you've never done anything in selling, you've never been a waiter before, you never worked retail, never had to sell. That's a skill that you learn over time. Like, you don't get new waiters that have never been a waiter, that are like killing it the first week. It takes them a few months, and then they're killing it like they had to go learn that skill. So I think that a lot of times people overvalue their skillset from their corporate career, or they overvalue the knowledge base that they have, and they greatly undervalue the marketing, the financials, the business management thing. So I always think about that when people come to me and they go, hey, I'm. I'm the best Mechanic in town. I want to open up my own performance shop. I'm so good. I'm super good. I say, hey, how are you going to do the marketing? I don't know. Okay, how much startup capital do you need? I don't know. How much are your overhead costs going to be? I don't know. Like they don't understand that there's a whole aspect of business management. I'm not saying this to scare people, I'm saying this to prepare people. Because you need to go start reading those business books and understand marketing. To me, the number one skill most people fail at is the marketing aspect because they think that if I build this amazing product or this service, all these people are going to start showing up. If I build this website, all these people are going to start buying stuff off of it. But they don't understand the marketing and how hard that is and how much time it takes to build that momentum and the confidence to go do that. So I think marketing to me is number one. That's the biggest failure.
Yeah. And we live in a world right now where it's really hard to be heard because there's so much messaging out there. How were you able to break through with your companies?
Early on I was very fortunate from being in the entrepreneurship space and building brands and large brands at that, that I was just able to take the same knowledge, the skill sets that I have and apply it to what I'm doing today. So I mean, literally that's what I help my clients because they come to me and they have a skill set or a knowledge base but they don't understand the business aspects. So we teach them really simple stuff initially like the profit first system. It's a great book. If you guys go read that about the financial accounting and putting money in different little accounts to make sure you're managing your cash flow for your business. Because that's the other thing is most people starve themselves on cash flow. They can't float their bills anymore and they're having to take in new work to pay for the old work. So they kind of starve their company and go out of business. That's one of the biggest reasons people go out so little. Things like that and understanding, okay, how do I do social media? What is personal branding even? What does that mean? What is an avatar? What is a customer avatar? So these are all new terminologies for people who are just getting into business. So the book itself is really a hand holding thing. That's how do I take the ideas that are Rattling around in my skull about business. Everybody gives themselves too much credit for their. Their ideas, the water cooler ideas, or they're at the lunch table going, oh, man, I'm going to start a business. This isn't this. And whoever it's at the table that's got the most ideas, it's kind of got the clout. But none of them ever make any action or take any action to go do those things. It's like, what does it even matter? So you got to realize that millions of people die around this world every single day with great ideas. But if they never did anything, what is it worth? They take these great ideas to the grave. They could have had the idea that would have made them a billionaire or changed the entire face of this world, but they went to bed and they just didn't do things the next day. They didn't go achieve or push themselves to go try those ideas or at least try to do anything. And that's unfortunate. So I want to make sure we get the ideas. I teach people how to evaluate those ideas against each other. Maybe you got three or four ideas and they think they're all great. Well, I did real simple calculations to figure out which ones give you the best odds of success. And then I always tell people, go all in. And when I say go all in, I mean, if you're not going to go 12 months minimum all in on something, then you shouldn't even start because that's one. It's an indicator that is important to you. Maybe there's some purpose baked into that. But also, are you consistent and disciplined enough to be able to get the results? Because you and I both know, Heather, that most people quit in about two to three months. We see this on social media all the time, you and I. We have this content always coming out. And you see these people that hit the. Hit the content scene like, really hard, they're putting out some good stuff. You're like, who's this newcomer? They're doing really awesome. And three months go by and they disappear. It's like, wow, did they go out of business? Are they okay? I hope everything's all right. You just kind of thinking the worst. We never think the positive when someone disappears, right? And then you see them six months later, like, oh, guys, that old thing I did, it didn't work out so well. And I got this new thing and I got this new business card and I needed you guys to do this. And I got this new show and they're always, like, trying to reinvent themselves, like Every six months. And we all have neighbors like that, or every time you see them at the mailbox or giving some other business cards or trying to get rich quick. And it doesn't work that way. Like, to me, like, when you first announce something different from your norm, like, hey, I'm going to go on a fitness journey. I'm going to start a business. Like, something that's outside of your wheelhouse, that's I'm normal. Your initial audience, your family and your close friends, they'll give you the golf clap. And they're like, yeah, you got this. Let's go. And so you give it a little fake boost of confidence because you go, wow, maybe this isn't going to be so bad. Look at all the support that I'm seeing. This is amazing. I didn't think anybody would support me when I said I was going to start a business and leave my job. And all these people are saying, cool. And about two weeks into it, nobody's saying that anymore. They're not saying that anymore. And you're like, wow, is my content sucking? Are the videos terrible? Am I doing this wrong? Am I good enough to do what I'm doing? And I'm sure that you went through this, too. It's probably resonating with you a little bit. So six months in, it's still kind of ghost town. And you're like, man, I think I'm just going to quit. Maybe I need to go back and get another job or maybe I need to start another business. And that's where missed people just kind of change their mind. They kind of pivot. They kind of lose that momentum. But here's the thing. I've started enough companies and failed enough times that I realized that if I can just outlast people, that that is a strategic advantage. And I know that if I can just make it 8 months, 9 months, 12 months, that now I'm only competing against 20% of the people that stayed in it. The 80% quit too soon. And we always think about that. We think about, like, three feet from gold when you're digging. Like, you quit and you could have made it a little bit more and you would have got there. That is so true. We see the pareto principle, the 80, 20 rule. Like, you know, the 80% will try really hard, but 20% will get the results. So I know that if I could just outlast people, and based on my 20 years of business, it's about 12 months. If you could just make it to that month of showing up every single day 365 driven my brand. Literally. You could show up every day and put some kind of a little bit of work in there to get towards your goal. You just outlast people. And here's the weird thing about that, because you and I are both experiencing this in a big way now, is that once you make it past that 12 month mark, people start to comment again. And like your posts, they're saying, wow, Heather, she's so dedicated. She shows up every day even when people don't like her post. There she is, she's making the content that's admirable. Like, that's some discipline right there. Like, she's really into this. They start to see that you're taking it serious. Eighteen months in, they're starting to tag their friends. Hey, you got to come here. Heather and Tony's what they're saying, you got to come check this out. This video they made reminded me of you or our situation. And you're like, cool. Two years in, you're starting to get tagged around the Internet by people you've never met before. And it's really strange to see that. And people are sending you letters like, man, you changed my life. You really impacted my life. Thank you for writing that book. Thank you for that video you put out. It really hit me at the right time. That's two years in. I'm in the year four now. So you start to see that where people are inviting bigger stages. And I've been on hundreds of podcasts and I've been on tv. I signed a TV deal that's going to film later this year. So understand that these are the things that take time, but you got to show up every single day and put some level of effort into every day.
Such a great point. And it's the hardest in the beginning, as you mentioned. Obviously the majority of businesses are going to fill in that first year or two years. But that's the commitment, like you said, make the commitment that you're not going to give up when you don't get that positive feedback, when you aren't seeing the results that. Because that's when you get through that window those first two years, which you really articulated well, that's when you start getting the amazing feedback. That for me, that's the reason why I don't give up now. Right? Because everyone has challenges, everyone has different problems they're going to face in business and in life. But when you're getting those DMs saying, you know, you helped me so much, I hope you know the impact you had, that's really that purpose driven work, that's more than just the paycheck that you say, I can't leave now because of these people. But you've got to get to that point and it's getting through that first hurdle which is the hardest. But you just got to commit and just be relentless in your pursuit for it.
Tell the truth. Were there times that you felt like you should quit?
Of course. Even during the pandemic there's been so many. Right? Because listen, for anyone who has gone into the entrepreneurial space and then a global pandemic hits, you're saying, these are the times I wish I worked for a large company and I was just collecting my weekly paycheck, no additional stress, you know, other than just working virtually. No, I'm saying to myself, why is it that I went out now? Why of all times am I out as an entrepreneur trying to figure out everything in the darkness, having no idea what I'm going to do. Why is it now that I'm on my own? So yeah, I've really struggled with that a ton. I think anybody has, you know.
But now we're looking back after that past year. I wouldn't want any, any other way. Because here's the thing, I always think about this. It's like when people are hesitant to leave their corporate job, it's because they believe that they're in a certainty situation. They think that that certain paycheck and it's guaranteed and it's steady income, you know, things that our parents programmed us with, go get that 40 hours, work 40 years and then die. Right? It's, you think that you have the certainty, you think that it's predictable. But the thing is, is that during the COVID the pandemic, we completely saw the opposite of that because it was a matter of your local government saying you're non essential, whether you like it or not, whether you're doing something good or not. To me, I think everybody's essential because if you're paying for your food, of your family and your shelter, you're essential. Unfortunately, government and politicians don't always agree with that. So we got to see people that had to leave and lose their job against their will. Right? And to me that shows that there's a lot of of uncertainty and higher risk. Because if you owned your own business in that situation, maybe they say, hey, you're non essential. You guys need to shut down your business. Well, you know what, you can look across your team and go, hey, what skill Sets do you have? What tools do we have? What apps do we have? Do we have a way to get paid? Do we understand marketing? Do we have enough money in the bank reserve to go do something? Well, let's pivot, let's regroup. Let's do something that's essential in this moment, and we have the option to go do that. You may struggle for a couple of weeks to figure out all that routine and the process, but you know what? You're not unemployed because you have the control if you're going to really shut your doors down or not. Whereas an employee, they could be like, hey, I know you've been here 30 years, but you got to go and realize when you work for somebody else, your employment is only one decision away from not existing anymore. And most of the time that's not even your decision.
And it's so true. The certainty that you're going to have, the only certainty you're going to have is a certainty within you, not outside of you. I definitely used to sign up for and believe everything you just explained. As long as I'm in corporate America and I perform and overachieve, I'm always certainly going to have a job and certainly get paid well. That's not real. And, you know, your company can be bought out tomorrow, technology can ship, your industry can decline, and suddenly there's layoffs and cuts. Not that has anything to do with you. However, you can be left out in the cold versus what you just explained, which is when you do own the business, when you are the owner, you are going to swing it and reinvent and change and test and try and keep going. And the good news is, that's when you really start finding that certainty within to say, okay, I was able to survive during a global pandemic. I'm sure this is going to get easier. I'm sure it's going to get better. And I'll keep finding ways. So I thank you for sharing that. It's so true.
My clients and myself, we had record financial year last year, given the pandemics going on. Because when you start realizing that there's a lot of uncertainty and a lot of fear that's going on out there, people are looking for beacons of light to give them some positive hope and give them some steps to get out of that and keep them encouraged and keep them motivated to push forward. So, you know, we see a lot of people that were in the influencer space that kind of just disappeared, which is really weird. Like, in a time that people needed them Most, they kind of just disappeared. And people are gonna remember that. And people, hey, you were a big thing that I followed. And then you disappeared. You canceled all your events. Like, what's going on with that? Like, they needed you in that moment. They're looking for true leaders to step up. And so the people that went double down and went harder and actually started to help other people and just push even harder. We're getting all the rewards from that now because people saw what our true character is and tragedy in times of turmoil. Right? So, yeah, I love what you said there.
Well, Tony, anyone who's listening right now is at least, least going to explore the idea of starting a side hustle on some level now that they know they are not certain or if they are already starting a side hustle and they want to scale it. How can everybody find you? How can they find the book?
Yeah, easiest way I keep it real simple, just one location. My website is 365Driven.com so365Driven.com and from there you'll find my book. It's called Side Hustle Millionaire. If you want to go look, it's up on Amazon. And I'm very active on Instagram and Clubhouse and Facebook and LinkedIn. So everything's in that one website. So, yeah, I appreciate it if you guys check it out. And also my podcast is called 365 Driven. You can look it up if you're listening to this.
Well, Tony, thank you so much for the work you're doing. Thank you for stepping into the unknown, into the fear, and showing up as that confident version of you as a leader, because you're helping so many people find that certainty for themselves.
Well, Heather, thank you for this opportunity and I love your energy and what you're doing out there in the world. You're really creating an impact yourself. And I can't wait to have you on my show in a couple weeks. But thank you for this connection.
Thank you. And for everybody listening. Keep creating your confidence. We will see you next week. I decided to change that dynamic. I couldn't be more excited for what you're going to hear. 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.
Come on this journey with me.
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