275: Jess Chan — Breaking Up with Your Toxic Business

All right. All right. Is your relationship with your business toxic? Is it time to get out? Step out the back, Jack. So we're going to talk all about that and more today. If you've been questioning whether or not it's right, we're going to look into that today. Great conversation coming up. Hi, everyone. My name is Bill Gallagher, Scaling Coach, host of the Scaling Up Business podcast. We have episodes and conversations like this. 3. Well, like this, not so often. Today's show special. No, we bring a show like this every Wednesday to you. We bring you a tip every Tuesday. So we've got shows for you every week. We've got hundreds of those and more wherever you get your content, your video, your podcast and all that. Or@scalingcoach.com our own website where you can get all the show notes, the downloads. So special offers, tools, that kind of thing from our guests and more. ScalingCoach.com is where to find that. So I'm joined now by Jess Chan. Jess, welcome to the show.

Thank you. So excited to be here.

So Jess has a marketing firm. Should talk a little bit more about that and her work and that kind of thing. And she's done. So the company's called Long Play. It's a full service email marketing agency. She's done some great work in that she's been featured in a lot of cooler new platforms that people are learning about. Digital DX3, Digital Growth Summit, Entrepreneur, Influencer, Hustle, Thought, Catalog. So arrange that. She's got some great stories. She's going to talk with us, but this core idea of knowing whether or not you and your business are right and she'll share some stories with us and like that. So welcome to the show.

Yeah, super excited to chat about this.

And Jess is in Mexico City right now, but originally and from. And based in Toronto.

Yes, yes. Canadian at heart.

It's a little easier maybe to live. I don't know about the COVID situation, but it's easier in terms of restrictions to be there in Mexico than it is in some other places.

A thousand person. Yeah, I mean it's, it's kind of. It's pretty open. Some masks are here and there, but nothing too crazy.

Well, this next week I'll be working with a couple groups in Toronto and I was just before I jumped on with you in a conversation with one of our leaders from one of our client companies in Toronto. So I've been like in Toronto land. Very connected to that.

Yeah. And the entrepreneur scene has been growing a lot over the last five years in Toronto earlier on there was, there was a lot fewer Canadian entrepreneurs on the scene.

So before we talk about some of the stories and things that led to this conversation, this topic, talk to us a little bit about how you got into email marketing and, and long play and give us some of your maybe a little your story that creates that background.

Yeah, I mean I think like most entrepreneurs, my story is the most non linear process of all time. My background was actually in actuarial science and economics so as far away from E commerce, marketing, creative as like physically possible.

And it's kind of right numbers, it.

Turns back around like life, like life does like the way weird skills that you thought were useless kind of come back around. So the, the quantum statistical analysis has actually been insanely useful for marketing now at this stage and like just business development. But wasn't really, wasn't really super excited about the prospect of sitting in an insurance company and just cranking out spreadsheets for the rest of my life. And this was kind of, this was in college and I kind of went down a little path of exploring a lot of different industries tried like UI ux, design, coding, development, all the different things. And kind of during that period as well was going through a pretty heavy period of like panic attacks, depression as well. So it was, it was an interesting time period of trying to figure out a career path and the sense of identity that comes with your career alongside this panic of like who am I? Where, what am I here for? It's all kind of meaningless. Like I think that that has been like a core element of kind of my career and business development growth and also kind of the core of, of this conversation as well going down that path. And then I remember I was, I think I was at a hackathon and I applied and I wanted to download a like productivity journal because I was like I need to get my life together and like figure out what's going on. And it was from this company called Best Self. And I was in college so I was like I can't afford like $35 for a journal. So I signed up for the email marketing newsletter and got a free PDF and two weeks later they had a job posting for marketing assistant. So I applied with zero qualifications, zero experience, but I remember writing like a five page portfolio on like here's how I would market the business knowing absolutely nothing about marketing or your business, but like here's how I would do it based on my research and ended up landing that marketing assistant position in my last year of college. So I was in that, in that job part time for I think eight or nine months. And then when I graduated they offered me the position of chief marketing officer of a multimillion dollar e commerce company. And I was like, this is the world's most unqualified promotion of all time, but we are going to figure out how to, how to do this. So that was kind of my first entry into just the world of e commerce and marketing in general. But in terms of email marketing, I remember one of the first projects they had me do was like hey, we should launch more of an email marketing newsletter for a company. And I remember still googling how to e commerce email marketing and that was kind of like the humble beginnings of what would eventually be long play, you know like three, four years later.

Nice story around what is unique or different about long play.

We are a complete full service email marketing agency. Most, most marketing agencies out there, especially in the e commerce space are full service. So for most companies, email marketing retention, like keeping your customer around, keeping your customers happy, getting that repeat purchase rate that's like a single line item. In most marketing agencies everyone's focused on acquisition. Everyone wants to talk about Facebook ads, everyone wants to talk about the sexiest like new marketing tactics and the hype and the tactics and methodologies that work. And for us, we're really focused specifically on the channel that's so built towards sending a personalized messaging to each individual customer depending on where they are, what they bought, their characteristics, their traits, what they've shown interest in. So we're really going all in on retention marketing, lifecycle marketing and extending your customers LTV and actually keeping your customers and turning them into raving fans. That's really, really what we see our work as. An email marketing is a perfect channel. It's actually. But our vision really goes beyond just email.

Cool. So there are some stories that form this that we talk to you about in preparing for the show and I'd love to hear some of them. We'll start off with something that I know a great deal about and that's a jewelry business. Talk to us about. Share that story with us.

Yeah, for sure. So and this story is really kind of a good case study, but it's really, I've seen this story hundreds of times in my very short time, even just in masterminds and kind of meeting entrepreneurs. But it's the process of someone who originally starts off a jewelry business with a true mission. They built a social enterprise. The mission is around how to empower people in third world countries to Support their families and actually have really great jobs and be able to be with their families while they're creating these products for this company. And it started off with such an organic, mission led, authentic place. And over the course of building a business, you start seeing that disconnect where we're human beings and we're going to have our own visions and goals and dreams. And for this entrepreneur, his dreams grew beyond what a jewelry business could possibly encapsulate. But your business is always going to be your business. And over time, we saw that disconnect between where his business could go and the cap of a business and how much it could possibly hold in terms of visions and dreams and ideals, and also what he could see his impact on the world being. And once you see that disconnect grow beyond a certain place, I see people going either in two directions. They usually get either very disconnected and they choose to either shut down the business or they just kind of farm it out, or they become that kind of that CEO, founder, owner, who is a little bit sporadic and comes in here and there, but it's not the way to truly lead a business because you're not fully present and you don't really care about the business anymore. And the other direction is you try to convolute the business into who you are now growing into as a person, forgetting that a business has its own goals, it has a business model, it has its own specific products, its own customer base. And you start getting this business model that becomes kind of a Frankenstein and the business itself loses a vision because your business is. You try to turn your business into a reflection of where you're going as an entrepreneur. And with this particular case, we saw that really break in a very aggressive way where the identity split was so severe that it became, it kind of went 180 very quickly, whereas I want to shut down the business completely. It was a multimillion dollar business, solid, very solid business, great team, a players, great customers. And he wanted to shut it down overnight. Thank goodness he had people who talked him out of that. But also he himself kind of went through this process of having that like psychological break, of having a disconnect from reality because he had been living in this like false Persona of I need to be the CEO and the founder of this jewelry business. And then while also trying to continue about living his life as well. And we saw kind of like a psychological, psychological break in him internally as well. And I think this was both the best, both the most heartbreaking reminder, but also very important reminder of, you know, as founders. Our business we started because it's an identity for us and we take a piece of us and try to like manifest it into this. This entity that can exist outside of us. But along the way, like, we forget that we need to redefine our relationship with it as it's going through the different stages of business growth. Because your business is going to be your life for the rest of the who you are. There's going to be more things you want to do, there's going to be more businesses you want to start, as most entrepreneurs do. And it's around how you redefine your relationship with your business as it grows and also as you grow.

Yeah, it's interesting. So what's the deal with the business today and what's his role in it?

So the business still running today, Revenue has definitely gone down a significant amount. You see kind of morale changes for the team as well with its key players really trying to hodgepodge it together. So for a little while he was completely out of the business for a few months, taking a sabbatical. And you could. And he had built a good enough business that his team could kind of keep it running without him. But they also couldn't undo the damage that was done over the last few. The previous few months where the vision was completely convoluted. All these initiatives were launched. There was a lot of wasted resources. Launching products had nothing to do with the business at all. And now it's kind of. It's kind of just a shell of like what it was before. Business wise. Still a fantastic business, but could have gone a lot farther with a very clear vision and him just kind of stepping out when needed and putting the right leadership in place to guide it where it could go for sure. So I think financially there was a massive hit there. And also, you know, seeing him run his business is like the light is gone from his eyes as well. Like you can kind of tell, you know, he's showing up, he's doing his job. Is it exciting to him? Is it? No. Is it probably actually draining for him at this point? It's like this thing that you built that was his baby that is now kind of an energy suck like that. I think that that is the most heartbreaking part to watch for sure.

Yeah, it's really interesting. I can relate very, very much to this. So my wife founded a jewelry company and then I worked with her as CEO of the company for nearly 11 years in growing the business. And she started the business because she liked to Shop. She had an aesthetic interest in things. It really started as an import company and evolved into a designer brand over time. But the point of the thing was to match an interest area, passion and interest, like some. Something that she cared and knew something about with a need to make some money. Right. Then the money she needed to make was enough to travel, enough to pay her rent, that kind of thing at that point in life. Right. As many years ago. Then that evolved later to support a higher lifestyle, a family, things like that. And one of the concerns that she always had was the, the impact of the product and the work and that kind of thing in the world. Well, it was clearly relevant and enjoyable for the people who bought it and wore the jewelry. They were very passionate made. It's very empowering, that kind of thing. But I've seen other people come into the industry and they were in it by accident or that kind of thing, and they like think, oh, it's. There's mining and metals and impacts and things like that and social injustice and they want to solve all of that. But the, the retail partners, the end customer, the. Where the, the person wearing the jewelry very often don't care a whole lot about those things. Some do to a little bit, but it's not really the driving thing. But you've got a mismatch of things that we're all passionate about. I hear a little bit of that one there where like they started it to address some social concerns. I don't know what the connection with jewelry was or wasn't, if they had a particular sense of design or that kind of thing. And then they get in this place where it's not necessarily working out the way they expected and their whole identity and everything is conflicted. Right?

Yeah. And I think the most heartbreaking part is that core reason why they started is still there. But in the process of building a business, so much more complexity gets added to it as well. Same thing with your wife, where she started it as a lifestyle business. What happens when you have a team of 50 and they need to be managed and there's finances and there's fundraising and all the stress. Is it really a lifestyle business anymore? And there's disconnect and like the core reason. And the passion might still be there and the impact element might still be there, but it gets buried in all the complexities and. And then you end up rejecting the entire business when really it's like if you just kind of redefined your role in it, redefined your relationship with it, you could find you could Remember why you loved it in the first place.

Or what you loved, right?

What part of it you loved. And it was. And this, I mean, this whole conversation and this topic really kind of started from my personal experience where originally like the, the goal was always just like, hey, I want to learn, I want to learn how to start a business. I have bigger dreams beyond this. I want to end up in the non profit space. But there's so many nuances in terms of running an organization that I would like to learn and kind of be a process and be in the process of. So for the first, you know, year, year and a half of long play, it was really just, I need to learn how to build a business. It was very selfishly rooted in like, proving my own potential to myself and seeing what I was made of. And hitting a million dollars was kind of that like, threshold of like, this is now a legitimate business and I'm a legitimate entrepreneur if you can hit a million dollars with like a proper team. So. And that was the driving force for a year and a half. And it kept me going. It was great. And there was never this question of like, is my business, is my relationship with my business toxic? Because there's no relationship. It was literally just, I'm going to give everything that I have into building this child up and like racing it until it can be a million dollars and have like a team of whatever size. And I found that as soon as we hit the million dollars and we had a team, I think of like 20, 25 at that point, because we're an agency, all that was gone. And then now is like the thing that kept me going. I hated, I hated every element of it. I'm like, I hate managing the team. I had done, like, I'm so bored of email marketing, so bored of this business, I just want to shut it down. I want to sell. Like, I just need to get rid of this thing. And it was because, like, I never kind of recalibrated along the way. And I managed a team of 25 the same way I was managing a team of five, which is like, what do you need? How do I help you? What do you need? And a million dollar business, it was like, what do you need? Like, what can I give but a million dollars? You can't manage it the same way as 100k. You don't have control over all the different factors, let alone at 10 million, let alone at 100 million. I've seen, seen entrepreneurs kind of hit that. It's the same journey over and over. Again, in terms of recalibrating and remembering, like when you, the start of a business is so different from running and growing the business that at each stage you kind of need to say like, what, what do I still love about this business? Like, what do I need to take out of it to serve me? And also what do I still want to work on? How do I, like, what is the relationship of the business in my life now? Because usually when we're starting a business, the business is everything. It's like a new relationship, right? You're like, God, your friends are so annoyed. But you keep talking about that guy you like and how great it is. It's like your friends are so annoyed that you keep talking about this business that you've just started and how great it is and your entire life revolves around this new idea. But as you continue growing at each of the stages, your business is probably going to be a smaller portion of your business of your life, especially as you start raising a family and having, and starting other businesses and like continuing about your career. So yeah, I mean my, the guy with the jewelry business, like, that's a really good, kind of like a really high water mark of like, this is how terrible it can get. But I think we all. I've seen it happen to so many entrepreneurs in little ways, even if it's just at a mastermind and someone stands up and they're like, I hate my business. I've been working on it for 25 years and I haven't taken a single vacation. I really hate this business and I don't know what to do. And that's so heartbreaking. And to me, because we all started out of this pure love and how does it turn into something that we hate and feel trapped by?

Yeah, it's really, it's, it's really interesting. It can happen lots of different ways. But thinking about what do you actually love and what do you need? And then redesigning things or changing your role or getting out of it or overhauling it, all of those things can make a difference. But I do think there's, there's, what do you love and care about in your life? There's what do you love and care about about your business? Do your customers love and care about? Why are the employees there? The why of everybody's work and having it, having things be aligned makes such a difference because when it goes off like you suffer, you do crap work, you neglect things, you set stuff up for failure. If, when things are out of alignment right when they're, when they're out of whack. Right? My. I remember my wife very clearly said, I just want to shut down the business. And I'm like. And it was because she didn't love the kinds of problems the business was facing at the time. She didn't want to work on those things. She wanted to work on other things. I'm like, oh, I like, those are interesting to me. I'll take that on. I'll work on that. So that's why I came in as CEO for a while, and we did. We had hundreds of silversmiths and multiple factories, and we had sold over $100 million worth of jewelry and hundreds and hundreds of stores and. And different channels and countries and things like that. And that was a big deal for a while. And. And then at another point, we are going through the next stage growth. She's like, yeah, you know what? I want to dismantle this whole thing. I want to take it apart. I want to go back to that piece that I really loved and figure out what that is. And it's going to take me a minute to do that. And that's actually when we did another pivot on the business again. And interesting things came out of that at each stage. Right. Thinking about that, redesigning it all, leaving no option as untouchable or. Or unrecognizable.

Right. And I love what you just brought up, like, the idea of, like, not leaving any option off the table and just having that space, like, again, redefine your relationship like it can. The whole point of starting a business is, like, free, pure autonomy. Pure freedom. You get to decide the track of your life and what your life looks like, and yet we kind of lose. Lose sight of that as entrepreneurs. And, like, we kind of get trapped by our own making and we forget that. It's like, you can do anything. You can do anything you want with this business. You could sell it, could keep it, you could bring in a CEO. You can do all of the things. But again, like you said, it comes back to, like, what do you actually want at your core? And I think. I think the idea that's always really fascinated me is, like, that the fact that us as entrepreneurs can stand up, you know, and say, like, I hate this business, and I really want to shut it down. And it's such a far cry from, like, why we started in the first place. And I just. For me, the process was so sped up, so we went from, you know, zero people on me just kind of piecing together a service to a team of 25 within, I think, about just under a year. So, like, that learning process in terms of, like, managing a team and, like, all the things that come with it, it's also my first business. It was like, it was kind of like from 0 to 100 really quick. And it was crazy to me because I remember sitting there going, like, I think I hate my business. And I just remember. I just remember thinking. I just remember being at Masterminds and thinking, seeing. Seeing entrepreneurs stand up and, like, that's crazy to me. I just want a business, let alone hating a business. Like, I just want a business. Like, that would be magical. Like, how do we get there? But the fact that as entrepreneurs, we can be trapped by our own making and, like, forget that we started this so that we can have freedom to decide what we want and create our own life and design our own life, I think that is the most intriguing and also heartbreaking part of the entrepreneurial journey to me.

I like the thing that you said there in the middle of it, that. That personal voice insight that you had. I think I hate my business. That's like a line from a Netflix series about an entrepreneur, right, who, like, goes one day, oh, my God, what have I created? But I think we all hit different points in our life. I can remember approach the age of 40 and having three businesses between my wife and I and kids and a house, and all these things that I had long said that I really wanted, and yet feeling trapped and miserable and all that. And in reality, a few months later, confronting being miserable, confronting feeling trapped, and then redesigning everything, I was now happy and lit up and engaged in something again. I still had all the same things, but the relationship, the way that I worked on it, was different. Had shifted in a number of months of engaging, roughly from a similar kind of an insight, like, nothing works here. Well, I'm miserable.

And I think that's the most important part that I think it's such a great call. Like, just having the courage to say, like, I think I hate my business. That itself is huge. Because then now you have a blank slate to be to, like, just redesign anything that you want. Whereas, like, for me, like, I was sitting in that space for, like, you know, three to six months going, like, I don't actually hate my business. Like, I just hate these. I'm like, no, I hate my business. Like, this is terrible. And went through the same process where I was, like, I explored selling it, I explored shutting it down. I explored, like, passing it off to a team, bringing a CEO, and, like, after that entire six month process, I now am exactly where I, where I was externally and nothing has changed externally. But I love it now. And all, all that, all it was was the internal shift of oh, these are the moves that we need to make internally so that I'm getting out of the things I don't love. But like, what do I still love? Like, oh, I do still have a vision. At some point I thought I had lost a vision for the business. I didn't care about it anymore. But once you have that space again to like we love, like suddenly the vision comes back and the direction comes back and like you're excited about it again. And I think, yeah, you bring up a great point sometimes that had nothing to do with really changing a lot externally. It has more to do with changing your mind and realizing like you're not trapped by your business.

So let me. We've done a lot of different shows on some related topics. Let me just point to some of those for our viewers and listeners. We've done a variety of shows on business and life purpose. We have done conversations about Gallup strengths, understanding and knowing what you love to do and what you don't love to do, where you have some potential, some talent themes to develop. We've also talked about love and loathe. One of the exercises we do to understand the places to lean into that might be related to those strengths and then things to give away, to delegate or to stop doing or to automate in your life. That's the love loath exercise. So there's a few things that we do with clients that we've covered in other shows before that I encourage you to go find and listen to. If you, if you haven't done that, talk to us. Share the story about the Accountant with the 30 year old business who was still doing things that she actually, I don't know. Yeah, that she was. Shouldn't have been doing anymore.

Yeah, for sure. So this was at. I was part of a few masterminds for a little while. This was at a mastermind. We were doing hot seats. And I still like so vividly remember this moment because you're supposed to go into the hot seat and give a specific business problem. Like, hey, I need to increase my performance in my design team by x percent. Or like we're having these cash flow issues. And she just like, I just hate my business. I'm miserable. I've been running this thing for 35 years. I have a team of like 15 people, but they're all useless. I do Everything myself, I've been taking a few. I haven't taken more than two days off in 25 years. I've never taken a weekend off for 25 years. I work, you know, 15 hour days and I've never taken a vacation. And I am so trapped by this thing. But I'm like, she's like, I need it to live my life. Like it's my cash flow. Everyone is useless. I have to check everything. And that was, that was. She just kind of stood up and she's like, this is my problem. We're like, okay, a lot to unpack here. That one was kind of a, almost, I guess a different type of problem than the story we were just talking about about the guy with the jeweler business that was more of a disconnect between the vision and the direction of the business and like his identity as a person and like his trajectory as an individual and like what he was really caring about. Now, you know, five, six years into starting the business, this one was slightly different. It was more of a. The business being like an all consuming thing in her life where her entire existence was to serve this business and she served the business versus the business serving her. Which is literally why we start businesses in the first place to some extent. And also building this cage of your own making where the more people you hire, the more people are useless and the more people your team needs to be handheld. So every single person you hire to offload work multiplies your actual workload. And she was absolutely miserable, but felt completely trapped because she couldn't shut it down because she still needed it from a financial standpoint, but also absolutely hated it and there was no way out. And that one has always really stuck out to me and also really came up in my, in my journey as I was kind of pulling out of my business as well. Because I think when we start, when we start businesses, we usually have some specific skill set that is a lot better than the average person. Which is why we were able, especially service based businesses where we're able to monetize it and market it. But by definition, because you are unique, that's why you can start the business. Which is why it's going to be very hard for someone, for you to hire anyone to just magically replicate what you do. And this really tied into this theme of how do you stay engaged in the business but detached. And I think that is the hardest balance to find. It's very easy to just be like, you know what, just don't give a crap anymore. I'M just backing off. If this thing burns down, so be it and whatever. And then there's also the other side, which is what she was doing. Like with micromanaging, everyone is useless. I need to like tighten the reins and I need to check everyone's work and everyone is terrible. I need to work every 15 hour days. But there's somewhere in between where it's, hey, I'm engaged. Like, how do I create a framework, how do I train and how do I build a team that's set up for success but also still stay detached? And hey, if a client's pissed off, great, we'll handle it. But I'm not going to let it ruin my weekend. Or hey, if a team member makes a mistake, we need to figure out where the mistake came from. But I'm not going to lose my mind over it at all. And having like the patience and also the space to let mistakes happen. And I think as entrepreneurs that is probably the hardest part, to just let go and watch it all fall apart, but in a leadership strategic way of like, hey, things are going to come up. What is the difference between leading versus micromanaging? And I think that's, that really came up as a really big practice around creating space between yourself as an entrepreneur and your business and your life.

So let me point to something I think behind what you're saying that I think a lot of our listeners are grappling with and that is I think people are trapped by, you spoke to it with this woman with the accounting business that she felt trapped by it, she needed the money for it. And I, I, there's a young person in my family, I'm watching go through a series of business now and they always keep enough cash reserve. They don't have big commitments in terms of rents, mortgages, family, things like that. So their freedom to shut something down, walk away and start try something else is really high. But I know lots and lots of people who bet everything on their business and set aside no money. Oh, I'm building the business right now. I'm like all invested. I'm, you know, and, and there's no room. And consequently they make bad decisions because they are in fact trapped, whether they recognize it or not. They don't have reserves for their rent, they don't have any other ideas. They've got pressure on a mortgage, on a spouse, on kids, on other kinds of commitments and they're boxed in. And, and they're not diverse in their things. And the thing is, if you could peel back from that a Little bit. So make your mistakes, be more flexible. When you're younger and you have fewer commitments, don't have everything into the business, keep some reserves, keep your day job for a while, work some things out, like give yourself a little more freedom. When I've come in to turn around a business or a product line or something like that, either as the person accountable or a coach to that one, one of the first things that we do is get some breathing room. So we slash off things that aren't working particularly well and we keep that gold bit. And then with that, we actually have some breathing room, some cash, some time, some things like that. We're not chasing things that don't work, that cost too much or whatever. We've just jettisoned those things. Now we're freed up and we can actually begin to think, is there something here that I care about, something here that has a future, something we can work on? And I think that's really key. And it's an area that we're not actually honest sometimes, even with ourself and. But very often not honest with the people around us. So maybe we confess to the person in the mirror while we're brushing our teeth or whatever, but we don't tell people how really like on the line we are with the pressure to make ends meet and to keep things going. Right. So there's no, there's no room to make any moves there for sure.

And I think especially early on in the business, and I know I for sure did this, which is you kind of justify it as I'm reinvesting the business. I'm reinvesting the business. And like yourself, yourself and your success in the business is one thing. So therefore it's okay. The businesses, I'll keep putting my time and effort and you know, delaying my salary into it. And I saw it as me not believing in myself if I was to take a salary out of the business, because that means I was taking out like cash to be able to grow this thing. And now it's that reframe of like I can believe in the business. I'm going to give my all on it. I can also protect myself personally and starting to separate the personal from the business side of things. And I think like, like you brought up, like most people just have the most stressful job in the world. They don't actually have an asset that they have built out. They just have. They can continue taking out pay. But as soon as you hit your business or you want to shut down, like there is no it's the same as quitting a job. You now no longer have any sort of cash reserve and you have no sort of like cash flow versus building an asset. The other difficulty I've seen even with people who have built a cash reserve from a financial standpoint, is they put all their eggs in one basket, identity wise. So even though like technically they could shut it down financially, their entire existence revolves around the fact that I'm the entrepreneur of a hundred million dollar business and I have this team and like this is my status symbol. And no matter even though you're like, you literally have like $10 million in the bank, you could shut it down right now like they physically cannot because then they would have no idea who they are. So I think it's about diversifying yourself financially and making sure you have those cash reserves, but also diversifying yourself identity wise as well, and realizing that like you are not your business and you are your own separate person.

Yeah, I watched one of my friends become very identified with his career and then have a career setback, get kicked out of the company and then attempt suicide because he was so tied to his identity and who he was. And another friend who didn't attempt suicide, but he became very depressed because the board, the investors, kicked him out of the company that he had founded. Now he walked out with millions of dollars in reserv, but he lost from being a very visible CEO. And for a long time he really struggled. He's in good place today. But for a long time he really struggled, fascinatingly enough, although it was deeply troubling for him at the time, less than a year later, scores and many, many people would see their companies evaporate overnight in the dot com bust that ensued. So in many respects he was super lucky to cash out and not to be left to holding the. Trying to hold that company together, which did in fact fail. So he was.

I mean the things that seem like setbacks are sometimes blessings.

Yeah, it's really interesting conversation. How much are you tied to it? Do you really know what you care about? Where are you at? So you've identified some moves and some steps and things like that. Share with us some of that that that you think are important.

Yeah, so I'd say like first off is kind of, you know, determining, like, hey, here are some signs you might need to break up with your business or you might have a toxic relationship with your business. I think the first one is the basics of like, do you actually still wake up excited in the morning? Do you wake up excited for Mondays? Are Is the best case scenario for your business still exciting to you? And I really lost that for a little while. It just seemed like more work. So are you still excited about the growth of it? Are you still excited about your day? Second one is, what are you getting from your business? Is it all given and no take? Is it, is it just you putting all of your energy, your effort, emotional, physical, mental into the business to hope it grows, but you're not getting anything out of it? Whether it's a sense of success, whether it's financial stability, whether it's, you know, a team, whatever, like whatever you, you should be getting out of your business and whatever you want and why you started the business in the first place. If you're really realizing it's all give and no take with your business, that's not looking so good. The third one is, do you feel a sense of, like, need to know every, every little corner of your business? Is there a micromanagement aspect to it as well, where you need to have this all encompassing knowledge of every single activity, every single person, every single decision in the business? Or is there some level of, like, disconnect, or is there some level of space between you and your business? I think the fourth one would be, you know, could you, could you still have a great life if you were no longer an entrepreneur or CEO? Is your entire identity of your business wrapped around who you are? And is the success of your business directly correlated to, like, your quality of life and who you are as a human being? And obviously those things are going to be correlated. Let's make sure there's some space between that as well. Fifth is, when you end the day. Do you feel success? Do you feel like you move the needle forward? Or do you just feel emotionally drained and like, oh, my God, we made it, we made it through another day, we're gonna do it all again tomorrow. Do you just feel like you're going to war every single day in a not good way? And obviously that's tied to being excited, waking up in the morning, six, which is probably a little bit more relevant for anxious, more anxious people. But, like, are you just waiting for a shoe to drop? Constantly, like, are you just waiting for, like, the cash flow to run out? You're waiting for, like, another person to quit. Are you waiting for something to go wrong? Constantly. You're just constantly on edge and like, constantly in survival mode with your business. And I did a seventh one, which I'd say the biggest one is, like, you're constantly telling yourself or constantly telling other People like, hey, it's bad right now, but like, when we hit 5 million, it'll be good. Or like, hey, it's not great, but like, when we hit 10 million, it'll be great. Or like, hey, when we do, when we hit the smile. So when we finally raise $100 million, it's gonna be great versus just loving it. Now, I think those are the big kind of the big seven bullet points that I would say that if a good number of these resonate with you or even if just one resonates with you, I think it's worth kind of sitting down and thinking about your relationship with your business and like, what. And taking the time to redesign it before it's all terrible. Before you just stand up and say, I hate my business. I need to figure out what to do. Like, now's the time to sit down and recalibrate.

Yeah. You know, I think there's something to appreciate along the way if you took on a new pursuit and you set a goal for yourself. I remember many years ago, I thought that it was time to transform my fitness. So I took on running a triathlon, my first one. And it seemed really audacious, and I was really excited, and it was very challenging. And then I started running, and running was really hard. And then I rode the bike, and I could only go so far and not very fast, and swimming was just really, really hard for me. Along the way, though, I started to appreciate different aspects of it.

It.

Right. Every run was hard because I was raising the level for a new thing. Every workout was hard. It brought a new challenge. But along the way, I started to realize, oh, I love my Sunday morning run. Oh, I love my Saturday bike rides. Oh, I love getting in the bay Monday evening. I had these things that I started to really like about it. Now, I didn't love the swims in the middle of winter, but I did love bragging about them I didn't love. Right. So, I mean, it's true. That's what I came up with. Figure out what it is you love about different things and how to transform it so that there's something to appreciate. Because if. If you're totally fixated on conquering a mountain, but you don't learn to learn to love mountain climbing, at some point along the way, you're going to quit that journey. Right. So there's something to appreciate. Like, wow, look, here I am at base camp. This is kind of cool. Like, here we're a place. Here I am at, you know, at this step and at the Next piece and there's something see and notice along the journey. If you can't figure out anything, then probably you have a problem for sure.

And I think you bring up a good point. Around like around like loving your, your Sunday morning runs where it, it sucks at some. Like it's really hard and you're exhausted and you're like, I kind of want to quit. But it's like a beautiful type of hard where you're still relishing in the pain. And I think it's about differentiating between different types of hard. There is, oh my God, it's so hard to grow this company but I'm still so exhilarated and we're so exhausted but in the happiest way possible. And that is a great type of hard. And there's nothing wrong with those 16 hour days and that is completely different from oh my God. I feel like I've given my life to this company and I can't back out now. So I just need to be a martyr to this thing and I have lost every part of my soul. Those are two totally different types of hard. And I think in entrepreneurship culture these days especially like we do glorify difficulty and we glorify the 16 hour days and the blood, sweat and tears and all those things are so important to growing a business. But it's also about differentiating. Like is it coming out of love or is it coming out of fear? And when you hate your business, it's really just like I'm going to keep putting in my blood, sweat and tears because I don't know who I am without this company or I can't live without this thing. And that, that's a different type of, that's a different type of grind.

Yes. I think it's totally different type of grind and different relationship to it. People get into this, oh yeah, I'm grinding mom, you know, doing my thing and I'm working so hard. It's really great. And, and alongside a long time we, we forget that it doesn't have to be like the, it could be a good kind of grind, something you're really proud of, something you're really digging on, or it could be something really, really miserable. There's so much good, fertile stuff for people to think about there. I want to give people some things to think, places to go and get more info and that kind of thing. We're gonna throw up a link to you and your company on the, on the website. Just Chen Ca of Long Play Brands. Super helpful, super fun conversation to get into today. I really appreciate you coming on and talking with us all about on it like that. I want us to give thanks to Lucy Summers behind the scenes, getting our show ready, queuing up the titles on the screen and that kind of thing. Promoting the show, preparing our guests and that kind of thing. Also to Vern Harnish, author and creator of the Scaling Up Framework, who brings that created the thing that that we've all used to go our businesses at this point point. Our audio for the show is produced and edited by Albert Burge at Poplight Productions. Our show notes get written up by Ein Kadina and proofread by Tim McGowan. I want to thank everyone for listening, for watching. We'll talk to you again next time. Thank you.