The Grit, the Decision,
and the Steps to
Becoming a CEO
Ep. 118 with Brad Crowell
“‘Being it’ starts with a decision.”
Get to know your co-host, Brad Crowell on this week’s special solo episode as Brad recounts his journey through music, working in the tech world, and his experiences with start up companies that has led him to be a CEO.
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In this episode you will learn about:
- Speak it while you do it
- The mindset shift for a new role
- There is a time to put your head down and work
- Give yourself a timeline, evaluate, and readjust
- Being it starts with a decision
Welcome to the Be It Till You See It podcast where we talk about taking messy action, knowing that perfect is boring. I’m Lesley Logan, Pilates instructor and fitness business coach. I’ve trained thousands of people around the world and the number one thing I see stopping people from achieving anything is self doubt. My friends, action brings clarity and it’s the antidote to fear. Each week, my guests will bring Bold, Executable, Intrinsic and Targeted steps that you can use to put yourself first and Be It Till You See It. It’s a practice, not a perfect. Let’s get started.
Hey everybody, Brad here, doing my first solo episode on the Be It Till You See It podcast. Stepping in for Lesley today and I’m really excited to be here. Been thinking a lot about how I have been ‘being it’ in my life.
I just want to share a little bit of backstory with you on my path to becoming a CEO, and all of the messy action that I took to get here. And I just want to qualify that and say, here is relative because I still feel like I’m growing and learning. And, you know, I haven’t had all the mile markers in my head that that’s self doubt, right? That justify me calling me CEO. It’s weird to say, “Yeah, I’m the CEO.” It sometimes it doesn’t feel right still. So anyway, I’m very excited to think back through this stuff. It’s fun to reminisce. I lived in LA for a really long time. And while I was in LA, I was doing music. And basically, the goal was to become super famous, tour the world with my band, and be doing the the music thing for the rest of my life. That’s all I wanted to do. Since I don’t know I guess, middle school, high school, I thought that’d be pretty cool. After being a super famous soccer star, was not physically possible for me, because I was a tiny little kid, the band thing seemed to make sense. Plus, I fit in and I loved it. And I’m good at that stuff. So when I got to LA, in order to get paid, I ended up working for a startup company. And you’ve probably heard me mentioned that before. And I won’t really go into the specifics of that. But it was a great opportunity for me to meet people, to learn a little bit about like how you work in a company, because I’ve never done that I’ve only worked for like retail, or in restaurants before that. And I hadn’t like been in a corporate environment before. And it wasn’t really corporate, it was very startup, you know, style. And basically, the whole idea was tech, social networking stuff. And that company failed after two years and that was devastating. Really, really, really devastating. I had a lot of trust in the people who are leading the team, and we had a great team. And we ultimately spent two years making a lot of really cool little things that never really took off. And that was a shame. But from that I learned, I learned a lot about hard work and, you know, being on time and all those kinds of things. I got hired into another company. And that company was cool. I had a chance to run a blog. And the blog was actually being handled by a bunch of interns. So I brought in a bunch of interns to do the writing. And I had basically to teach them, I was the first time really truly leading a team. And we had all these different bloggers all over the country. And then basically, that company fired me (Brad laughs) after like a year and change, right. The CEO will took some very dramatic measures. He let go the entire marketing team, including the blog department, and they went like 100% the advertising route and they just cut out any organic reach, any social anything, they let go of me and two other people that we were all working together. And that was, I kind of saw the writing on the wall. So it wasn’t really as devastating when that happened. But that company was very corporate, right. The people I worked for what used to run major companies, big companies, you know, they, they had very corporate expectations, I learned all that kind of stuff from them. And, and then I actually basically didn’t work for like a solid year. And I spent my time working one night a week at a restaurant and living, living very, very frugally.
But dedicating all of my time towards music. Every single day, I was working on music, and it was probably, even though I had no money at all, it was one of my favorite times, because I was living with some friends. And I was also working diligently on music, that’s when I started touring, and being very intentional towards growing that. And then I got a phone call, after a solid year of basically putting myself in debt, I got a phone call from some of the people I used to work with. And they hired me to work on another project. And that was great, because it, actually, I was really hesitant to go back and work for a startup company, because I loved what I was doing, even though it was making no money. But it was complicated. And I got a dog and I decided I needed to actually get paid consistently. So that was the first time I worked for the company that I then spent the bulk of my career at. And that was a startup company. That was more of like a startup house, we had a lot of projects going all the time. And I will spare you the details of that. Because we had so many projects over the years that worked for them for six years, six years, seven years, something like that. And along the way, there was a larger company there was like, I think 80 people, and I was kind of part of different teams, and shifted through to do different roles. And then at the end of it, by the end of it, I was the general manager, and my job was really to poke my head into the different projects and make sure that they weren’t, you know, losing too much money. I jokingly like to say, but really just it was about how can I help out, you know, with all of the crazy random experiences of different hats I’ve worn over the years at this point. So like, at this point, it was probably like, almost 10 years in startup companies, right? And from account management, from marketing to being the middleman internally between the CEO and design and dev are so many different roles. And but that company was the first time that I actually, there was a shift in my thinking in that company. Because it was the first time I thought to myself like, “Hmm, that’s not how I would do it.” And that was a surprising thought to me. Because before it was like, well, someone’s telling me what to do, and I’m just gonna go do my job. And it was it was the first time I thought like, “Huh, if I had the bank role that these guys have, I would do things differently.” And this is how I would do them. And I really started to analyze how to to get, how I would have done things differently, and why would I have done things differently. And, you know, I used to say someone gave me a million dollars, I would know exactly what to do with it. And that was that was an interesting turning point, I think and that’s kind of what really led me down this path of being my own boss. Now, I never thought I’d be a CEO because that wasn’t even on the radar just knew that I would leave, eventually I would work for myself, I would have my own company. And I would do something, right. And ultimately, that decision came when I had a really challenging transition internally. When I project that worked on for a number of years, actually sold to another company and I was expecting to transition with the company to this new ownership and and I ended up instead staying at the company I was with and that was I had a really hard time with that because for six months to a year I was like working diligently to get the company ready to sell. And I knew I was gonna go run the company over there be second, you know, I was I wasn’t gonna be the CEO, I was gonna be the COO and that’s not how it ended up happening. And that was really really really difficult but that’s really what made me realize I need to, I need to move out on my own. I need to do my own thing.
And when I finally did that, the the first thing I did I had started while I was working for the, for that company. I had a friend of mine of a longtime friend of mine had started a web development company. And I was always very nerdy with websites, I’ve been doing them for the bands that I was in and my friends, and just like constantly fascinated by WordPress and technology stuff. And so I ended up joining his company that he had started. And he and I became partners. And it was a lot of fun. We worked together on nights and weekends for many years. And and that was kind of always happening in the background, because I was doing my job during the day. And then at night, I would noodle around on websites, or I would do some sales calls and emails and whatever. And we were building websites. So when I left the role, the job that I was in, it became the obvious first step was, let’s, let’s work together more closely. Let’s see if we can grow this thing. Let’s see if we can make this thing make enough money to pay both of us. Instead of just like a side income, it was like how can we make this a primary income. And it was, at the same time that I had a couple of other friends had approached me to do some other things. And one of them asked me if I wanted to help do product development on a small company. And so I said, “Sure.” And then a third friend and I had been doing live streaming for a company that are for a TV show that we’ve been working on. So I ended up leaving that role and immediately starting three companies at the same time, or growing one company that had already been started and then starting two other companies as well. And so I was very split. And then in the meantime, I was also helping Lesley at night. And it was a it was a crazy couple of years, where two two solid years where ultimately, I really, I was able to pay my bills, and like, you know, get enough money to eat, and stuff like that. But it was not actually a real growing opportunities were they weren’t like actually turning into what we had all hoped they would turning into. And that was that was really frustrating was really a shame because I was actually working with my friends who I love dearly. All three of them were some of my closest friends and, you know, at the time and and, and then became this like realization that like, “Something isn’t working here,” we’re spinning our wheels, we’re not actually growing. And it’s not like that putting food on the table, let alone becoming a company where we could like grow a team and build a team. And at that time was when a, Lesley joined a Mastermind group with a power couple, Chris and Laurie Harder. And she told me she really really, really, really, really wanted me to come join. And I was very hesitant to do to do so because it was expensive. And I was very I didn’t have I didn’t have any extra cash. And so my money mindset was not helping any any of my businesses and it certainly wasn’t helping me grow and but she convinced me to do it anyway. And I’m so glad I did because I was paired up with a coach, a one on one coach. And he basically told me like, “Hey, man, all this stuff you’re doing with these three companies, you should stop. And you should, you should actually throw, throw in all, you know, throw your weight in behind Lesley, and you should work with her.” And I I, that was so appealing to me. But I was really really worried about burdening her her budding company with my salary, you know, because I knew I had to make X amount of dollars per month. And I also been in so many positions where I’ve seen too much strain, financial strain on a company out of the gate actually crushed the company and nothing happened. And I was really really worried that if I let go of these the side incomes that I had that weren’t growing the way that we had all hoped that suddenly I would also, I could also sink what she had been working on and coach basically said, “You know, you’re gonna make enough money, you just have to do it.” And it took me a little bit to make the decision. But as soon as I made the decision, I started slowing down the work when those three companies, one of them I was able to step away from very quickly, another one we had a bunch of gigs still that we had to complete, and then the last one took literally a year to actually shut down and extricate and all this stuff because it was it was pretty complicated. And the but I’d started putting my operational experience in behind Lesley and really what working on her websites and changing the way that the flow in the company had worked and the the switch to CEO didn’t actually happen right away. I was ops, she was the owner of the company, it was her company she started, right. So she was the CEO by I guess, default, I don’t know, it was a small team, it was us. And like two other people. And so there’s four of us. And I don’t know, the concept of CEO wasn’t really a thing.
And also, I was very, you know, happy with her, making the decisions and doing what she was doing. And I would just execute, because execution is kind of like my sweet spot. It’s where I feel comfortable. It’s my, where all my strengths are. And the operational execution side of things, is, it’s home for me, right. And funny enough, though, that wasn’t where I, I saw myself, in my own mind, even though that was where my strengths were, are, are, and what I’m good at, in my head, I was like, “You know, what, I see myself making the decisions and, you know, leading the team and building relationships with other companies.” And, you know, and being that that role, and Lesley had also basically said, like, “I hate being in meetings. I hate doing all this stuff. I don’t want to make these kinds of decisions. I’m a visionary. I want to conceptualize what the product is, and then bring it to the team.” And, you know, we they can build a to build that stuff. And we had been, we didn’t come to that realization, quickly or easily, we were working with another coach, Kareen Walsh, and she had said, you know, she had put us through a couple of exercises. And after the exercises were over. She she started laughing when she was looking at what we had drawn out, and what how he described ourselves, and she said, “You two are in the wrong roles.” And we said, “Well, what does that mean?” She said, “Well, he’s the CEO, and you’re the you’re the Chief Product Officer, you know, you’re the visionary or whatever.” And suddenly, it was like, “oh, duh, that totally makes sense.” And, you know, so when we got home, we, you know, nothing formally changed, except for, we just started calling ourselves a different things. But I think mentally, it really did change. You know, it put me in a position to think like, “Wow, I if I’m going to be the boss, you know, what does that mean? How do I show up?” And it really did shift my mindset on being more present, and, you know, connecting with the team and thinking like a leader and learning a lot about that kind of stuff. And, you know, so, so, that’s kind of the path that took, I took, I guess, to become CEO, and, you know, obviously, there’s a lot of, it wasn’t linear by any means. It wasn’t like, “Okay, and then I wrote, climbed the corporate ladder, and now I’m the boss.” And I, I have a feeling that it’s never linear, it’s very rarely rarely, that you start at the bottom and you you become the boss. You know, so I don’t know that it’s necessarily replicable. However, looking at that, and thinking, what are the messy action? Like, what are the steps I took? How was I ‘being it’ while that was happening? You know, I think that’s kind of something that can be replicable, replicated by, you know, it’s something that you can take away from my experiences, and, you know, the things that the things that I was doing to be it when I was, you know, before I even started in tech, when I was in the band, you know, I saw myself touring, I saw myself recording for others, writing being in a band. And even though I, you know, I had no money and no, like, you know, I had a little bit of a network when I moved to Los Angeles because of my school, but I would go out all the time, and I would meet people, and I would intentionally, I would introduce myself as, “Oh, yeah, I’m a musician. I’m a bass player. I am a singer. I’m a writer.” You know, and I was, I was speaking it, while doing it, even though I wasn’t making a money doing it, but that’s what I was out there to do. Right. And when I got into startup company, you know, the, the first thing that these guys asked me was like, “You know, have you ever done marketing?” And I was like, “Hell yeah, I’ve done marketing.” You know, I’ve marketed myself and my bands since I was a teenager to get people to show up to a club and me play show for them. Right? And they, they were like, “Yeah, okay, that’s,” you know, but like, in a corporate environment, I had never done that before, you know, so this was new to me, but I was like, “I know how to do this, I’m gonna figure it out.”
And, you know, so then I, when I got into those companies, though, wasn’t anybody telling me, this is how you become an account manager, there was no real training, because in a startup company, you’re kind of making it up as you go along. You know, so I would go read blogs and books. You know, when I stepped into the role of COO of a skin and haircare brand. The first thing I did for like, weeks was like, “What does the COO do? How does the COO operate?” You know, and I would then just start to make decisions and implement that stuff, as it was, as you know, we were all working together. And even though I, I did feel like I’m just a, I’m just an operations guy on COO, you know, stepping into that role, you, it’s the same thing, as I was talking about what being a CEO. When I stepped in the role of CEO, it changes the way you show up for yourself, right. And that I think, is important, you know, there’s like, I think, over the years, I’ve seen moments in my life, where, where I know, okay, from this point forward, at least for a short window, it’s, it’s crunch time, or it’s go time, right, like, it’s time to buckled down and really kick ass, and it’s going to be three solid months of like, you know, intense work, and then I’m going to have a breather. And those kinds of moments are real, they really shape you, because you are making a real decision that you wake up with, and you go and you do the thing. And then you know, you get the chance, at the end of that, that window of time to look back and go, did I do what I needed to do. And when you, when you do that, it really does have a, like, a lifelong effect on you in a way that gives you that confidence, suddenly, you are you know, you can do it. Right. You know that, if you need to, when you need to, you can buckle down and get it done whatever it might be. And that could be you know, opening a Pilates studio, or it could be raising a kid, I mean, maybe you have an 18 year sprint, you know, for that, and I don’t envy any of you doing that. But it could be you know, getting a puppy and learning how to train a dog, you know, it could take 6 to 12 months of consistency to in order to you know, get the dog where they are listening to you whatever. It could be training a new person on your team or, or hiring a teacher. And you have to like show them the ropes and “Okay, for the next two months. I’m gonna like every day diligently work with this person.” And when you’re done that, even though you never called yourself a trainer before, now you you’ve been doing it, you’re you’ve been being it until afterwards. Now you’re you are it and you see yourself as that and you go, “Yeah, I did that. I know how to do that now.” You know, so, you know, I am grateful for you listening, if you’re still with me here. And I want to encourage each and every one of you that it really does start with a like ‘being it’ starts with a decision. Right? It’s the decision to go do the thing, even if you don’t know what it is or how you know what it ultimately is going to become. Or if it’s or if you don’t know exactly what you’re doing, just making the decision that you’re going to go figure it out is going to change. You know, and give yourself a window, tell yourself like, “Alright, I’m gonna figure this out over the next two months.” And, you know, be diligent with it. And then after those two months are over, you know, did it work, yay or nay? You know, when I when I started those companies, with my friends, it became obvious after like, a year and a half, two years that they weren’t growing the way we needed them to grow, to pay all of our bills. And for any number of reasons, there was a lot of reasons behind that. But it was like, okay, I it was our I felt, even though it’s hard to separate myself from my closest friends. And it became there was an obvious, “Okay, I had given myself the window, and then I evaluated at the end of it, and it was time to make a decision.” And that decision in those cases, unfortunately, was to move on. Right? Where some other times it might be that, “Okay, this is going well. Let’s double down or let’s hire a team or let’s, you know, like, find another partner” or I don’t know, whatever take you on the road. You know and so,
Anyway, I want you to to think about setting yourself a timeline and then going after it for that timeline and then afterwards evaluating. Right? Because I think that is going to help you be it till you see it. So let me know, how you are going to use this this tip, these tips in your life. I’m really, I really want to know your story. I want to know, you know how this is going to impact your story in your life. You can DM, DM us at the pod at @be_it_pod on IG. So, thanks so much for listening. Bye for now.
That’s all I’ve got for this episode of the Be It Till You See It podcast. One thing that would help both myself and future listeners is for you to rate this show and leave a review. And, follow or subscribe for free wherever you listen to podcasts. Also, make sure to introduce yourself over on IG at the @be_it_pod on Instagram. I would love to know more about you. Share this episode with whoever you think needs to hear it. Help us help others to BE IT TILL YOU SEE IT. Have an awesome day!
‘Be It Till You See It’ is a production of ‘As The Crows Fly Media’.
It’s written, produced, filmed and recorded by your host, Lesley Logan and me, Brad Crowell. Our Associate Producer is Amanda Frattarelli.
Kevin Perez at Disenyo handles all of our audio editing.
Our theme music is by Ali at APEX Production Music. And our branding by designer and artist, Gianfranco Cioffi.
Special thanks to our designer Jaira Mandal for creating all of our visuals (which you can’t see because this is a podcast) and our digital producer, Jay Pedroso for editing all video each week so you can.
And to Angelina Herico for transcribing each of our episodes so you can find them on our website. And, finally to Meridith Crowell for keeping us all on point and on time.
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