She Built a $10M Marketing Empire By Rejecting 'Masculine' Business Rules

We spoke to Jess Chan in this week's episode of Moneywise.

Jess is the founder of Long Play, a marketing agency that achieved seven figures in revenue within its first year. She's a second-generation Canadian who grew up outside Toronto and transformed her business philosophy from chasing revenue to prioritizing profit and personal wellbeing.

Like all Moneywise episodes, Jess breaks down her net worth, income, portfolio, and monthly expenses and then I, your humble host, pick it all apart.

We also went deep on: how shifting from masculine to feminine leadership transformed her business, why revenue is just a vanity metric, and how she spends less money now but feels wealthier than ever.

Below you'll find my summary of the episode along with the entire transcript.

And by the way...this podcast, the concept of it came from Hampton, which is a private community of successful founders who get together regularly in small groups to talk about the truth behind their businesses, their wealth, and how they're actually spending their money. So if you're a CEO, founder, or business owner, check this out. New Moneywise episodes come out weekly.

Listen to this episode on:

• YouTube
• Spotify
• Apple Podcasts
• Amazon Music

The Numbers

• Net worth: Approximately $10 million ("around the eight figure down a little bit mark")
• Business revenue: Mid-seven figures annually with Long Play (marketing agency)
• Early freelancing income: $30-40K per month before starting Long Play
• Business journey:
  • Year 1: Hit seven figures in revenue but was "the least profitable ever"
  • Years 3-4: Rebuilt foundations, focused on profitability over revenue
  • Years 4-6: Business became sustainable, profitable, and personally fulfilling
• Monthly spending:
  • Previously: $10-15K monthly (personal assistant, chef, trainer, high rent)
  • Current: $5-6K monthly (more intentional spending, cooking at home)
• Investment strategy: Mostly autopilot ETFs managed by her parents' financial manager

Building a Business Beyond Revenue Ego

Jess Chan's entrepreneurial journey reveals a powerful evolution in how she measures success. In her first year of business, she was laser-focused on hitting seven figures in revenue. "To me, being a real entrepreneur meant seven figures in revenue. Like before that, it didn't really count in my mind," she explains.

This revenue-first mentality came with a heavy cost. Despite reaching her revenue target, Jess describes this period as "the least profitable ever" and "the most stressful year of my life." She was building what she now calls "a castle built on sand" – impressive from the outside but lacking solid foundations.

The turning point came in years three and four, when she shifted focus from external validation to internal health. "Year three and four was tearing all of it down to go back in and rebuild the foundations so that it was actually scalable, sustainable and profitable," Jess shares. This meant difficult decisions: "We went through a period of turned over the entire team, turned over half of our client list. It was a huge purge."

This transformation wasn't just about business metrics – it reflected a fundamental shift in how Jess defined success. "Revenue is just the number to strike your ego," she realized. The real journey was moving from revenue (a vanity metric) to profit (sustainability) to wealth (true abundance and contentment).

Feminine Leadership in a Masculine Business World

One of the most fascinating aspects of Jess's story is her evolution as a woman in business. "For the first few years, I think I was just being a man in business," she reflects, "I valued myself off the things that men are valued off of. I led the way that men lead."

This approach worked initially – she proved she could succeed in the traditional masculine business model. But it came at a cost to her authenticity and wellbeing. The breakthrough came when she began embracing feminine leadership qualities: "What are the things about being a woman that's uniquely powerful? I think women are really, really great at harmonizing. I think they're really beautiful at creating safety within a team."

Jess is careful to distinguish between gender and energy: "I always use the term masculine and feminine instead of men and women, because I think it's more about bringing in the energy of feminine leadership into entrepreneurship." This perspective resonated with host Harry Morton, who shared his own experience finding success by embracing his more introverted, emotionally sensitive leadership style.

The results speak for themselves. By leading with more feminine energy, Jess has created stronger client relationships, better team retention, and a more fulfilling work experience. "I think business and the world could use more of that," she concludes.

Redefining Wealth as Freedom to Create

For Jess Chan, true wealth isn't about numbers in a bank account – it's about the freedom to create. "Freedom to create is probably my core need as a human," she explains. "It is a freedom to create a business. It can be the freedom to create like a book... a team... a really healthy environment... a home, a family, an adventure."

This philosophy manifests in how she approaches both business and personal finance. Despite growing her net worth to approximately $10 million, Jess has actually reduced her monthly spending from $10-15K to $5-6K. Yet she describes her quality of life as having "gone up like 300%."

The shift came partly through her relationship with her partner, who showed her "a beautiful way of relating to money where he's just able to make so much with so little." Simple changes – like cooking at home instead of dining out and finding a more practical living situation – have increased her satisfaction while reducing expenses.

Perhaps most striking is how Jess has maintained her ambition while finding contentment: "For years ago, I thought I was scared. If I became content, I would stop becoming ambitious. But now I really believe contentment, ambition can coexist." She still aims to build "an eight nine figure business," but not at the expense of her wellbeing or authentic self.

This balanced approach contrasts with entrepreneurs who chase exits at all costs: "I've met so many entrepreneurs where they did it, like they got the $100 million exit... and they're like, I don't know who I am. I don't know how to be happy."

The Spiritual Side of Entrepreneurship

Throughout the conversation, Jess reveals how her entrepreneurial journey has been intertwined with personal growth and spiritual development. When asked about finding the confidence in her approach to money and happiness, she frames it not as being "right" but as offering "a really interesting perspective that I'm bringing to the table that other people should take the time to think for themselves and reflect on."

This humility belies a deep wisdom about the entrepreneurial path. Jess understands that beneath the surface-level goals of revenue and growth, there's usually something deeper driving founders: "My hunch is like, there was like, there's something to prove about yourself... I want to see what was inside of me, or it might be something to do with, hey, I want to have full autonomy over creating the life that I want."

The spiritual breakthrough for Jess came when she stopped seeing money as something to chase and instead viewed it as "fuel to continue doing more of what we want to do." This shift allowed her to separate business challenges from her sense of self-worth: "Now it's more of like, yeah, that's a business problem. But life is still good."

Perhaps most profound is her observation about the relationship between business success and personal transformation: "Once my relationship changes, the business has always succeeded more after that." In Jess's experience, inner work precedes outer results – a lesson many entrepreneurs learn too late.

Other Key Quotes

"I feel like I'm living a fuck you lifestyle in terms of contentment."

"Year one and two felt like we had proven out the value prop works. We know what we need to deliver, we know we need to go to market, and we're growing really quickly. Year three and four was tearing all of it down."

"Entrepreneurship is primarily male dominated, and that's not a bad thing, but that is what is known. That is what's easily recognized as strength. That's what's easily recognized as success."

"I've taken a lot of inner work, a lot of medicine. The biggest lesson I would say is to break free of that. It's less to do with the business and how much success the business is having and has everything to do with changing my relationship to the business and changing my relationship with money."

"My parents never actually broke six figures in household income until probably the last few years before retirement... Looking back, like having my perspective now of success and ambition and what a good life looks like... the abundance did not come from having a lot of money, but I never felt like we worried about money."

"I always had a really deep desire to create, and I don't know that I would have articulated that when I was younger, but the desire to just create and make things explore and adventure and just be curious about the world."

Links You Might Like

• Long Play - Jess Chan's marketing agency
  
  

Full Transcript

[00:00:00] Harry Morton: Jess Chan says revenue is just the number to strike your ego. But she didn't always think like that.

[00:00:05] Jess Chan: To me, being a real entrepreneur meant seven figures in revenue. Like before that, it didn't really count. Year three and four was tearing all of it down.

[00:00:14] Harry Morton: This moment flipped her thinking on money, happiness, and how entrepreneurship, whether we realize it or not, leans hard on masculine energy, often at the expense of the feminine, which has changed everything for her.

[00:00:25] Jess Chan: Once my relationship changes, the business has always succeeded more.

[00:00:29] Harry Morton: Sneak preview. She's worth about 10 million today, but she spends less than ever. I'm Harry Morton, and this is Moneywise, a podcast not about how to get rich, but about how to use your wealth to live a happy and fulfilling life, mostly by learning from the mistakes of others. This is a podcast made for the Hampton community, which is for successful founders currently on this exact journey. Check it out at Hampton. Com. So let's talk about that revenue chase because by that metric she was winning early.

[00:00:56] Jess Chan: Long play. It started off I was just freelancing for a little bit. That was, you know, before it was considered long play, but it was the early stages of it that was probably the peak cash flow personally, that I would have for a very, very long time. If anyone just wants to do entrepreneurship for the cash flow like this, don't start a whole, whole company. And so I was doing that for probably about 6 or 7 months.

[00:01:21] Harry Morton: And when you say cash flow, just, just give me like a ballpark. Like what were you earning back then? Do you think.

[00:01:25] Jess Chan: I was making about 30 to 40 grand a month by myself? This was when I was full time with Best Self and then also handling some clients myself as well. I think at the peak I probably had about five clients I was managing by myself, so I was doing as a full email, as a marketer, and then I think I had like a VA help here and there, so there's no real expenses.

[00:01:52] Harry Morton: Got it. And so then and then what was the what did the sort of graph look like after that? Up till now.

[00:01:57] Jess Chan: We got to seven figures in revenue within the first year of me going full time into long play. And at that point we had I had a team of probably about 5 to 6 people already. And that's also when we were the least profitable ever. And when we talk about external validation, I was in that entrepreneurship world so much. And to me, I'm like, I want to be a quote unquote real entrepreneur. And to me, being a real entrepreneur meant seven figures in revenue. Like before that it didn't really count in my mind. Yeah. And so that first year, everything was geared around, we just need to hit seven figures in revenue, whatever it takes. Obviously, I wasn't consciously like, hey, I want to lose money. But the priority was, let's get to revenue. If there's a client coming in, we can do it. Let's take it. Like if we can expand capacity, let's take it. We'll figure out the back end later. And that was probably the most stressful year of my life because I went from being a CMO. It was very cushy just because it was a good, stable company. I worked with a team for a while and had a few side clients. Was making good money too. I'm now completely on my own in my first business. I barely know how to do my own taxes because I was like 2223 at that time. So I'm like, I barely figured out, like life as an adult. Like, I just moved out for the first time.

[00:03:21] Harry Morton: There's a lot to say about this period in her life and why everything shifted. But I do want to give you the current numbers right away. So let's jump ahead in the timeline for just a moment.

[00:03:30] Jess Chan: So now we are about in the mid seven figures in revenue, insanely more profitable. The first year I had grown so quickly it felt like it was a castle built on sand. Second year was about the same thing too. We grew really, really quickly from a revenue standpoint and we started getting a little like a little bit more profitable, but it was still a lot of turnover internally from the team. There's a lot of culture things to put in place, like it was that early stage of like, let's just get bodies in to write some copy, do some design. But I had to hold everything. Like I was queuing everything. I was managing all the clients and so I was getting burned out. So by year two, I was in a place where I'm like, I am so exhausted, like, why did I do this? But also now I'm so committed that I can't shut it down. So I think I felt stuck again. I was really lucky that I found Rachel, my CEO and partner now at Long Play, so she came in about a year or two ish, and together we had started doing all the work to stabilize the company. And so I think year one and two felt like we had proven out like, you know, the value prop works.

[00:04:35] Jess Chan: We know what we need to deliver, we know we need to go to market, and we're growing really quickly. Year three and four was tearing all of it down to go back in and rebuild the foundations so that it was actually scalable, sustainable and profitable. We went through a period of turned over the entire team, turned over half of our client list. It was a huge purge. And so the company really had to shrink and get smaller. And that was really a period where I had to go through the process of letting go of external validation, letting go of external markers of success, and really looking internal like, is this healthy? Like, is this a healthy business? Am I healthy in the process of running this business? Do I get enough energy from this thing to want to do it for another ten years? Because that's probably where the money actually is to be made. Not sprinting as hard as fast as I can for a year and to hit these metrics and burning out. Um, so you're in three and four was a lot of, um, internal recalibration and then years like 4 or 5, six now, like, this is when it's gotten really good. Like now now I feel like I'm lucky I've gotten to the good part.

[00:05:41] Harry Morton: What is your net worth today?

[00:05:43] Jess Chan: I don't really do these, like, hard calculations, honestly. Um, I think it's probably around the the eight figure down a little bit, Mark. 10 million, give or take a little bit. Um, I think it really comes down to like, how do you want to value the business. The multiplier is there, which is why it's a little wishy washy.

[00:06:01] Harry Morton: So this is where Jesse is today. And in a bit, we'll get into how her personal spending and relationship with money have evolved. But first let's talk about ego. Because ego is a huge part of being an entrepreneur. And that's not a bad thing. I mean, it's kind of an insane thing to build a company from scratch. It takes a certain amount of ego to even believe you're the kind of person that could make that happen and get something off the ground in the first place. So, yeah, we naturally have big egos. But for Jess, shifting focus from revenue to profit wasn't about killing her ego. It was about finding balance with it. Here's how that played out.

[00:06:36] Jess Chan: There's definitely a lot of ego there. And ego can can be defined in so many different ways, right? Like I think sometimes the masculine form of ego and this is a very generalized term. So not necessarily just like the masculine form of ego can be much more about like I've accomplished these things like, look how successful I am, look how ambitious I am. Like, it's a marker of value to be seen in that. I think sometimes the feminine form of ego can be more about. Look, I can hold it all together. Look, I take care of everything. For me, it wasn't. Hey, I need someone to give me the trophy for how much revenue I've generated. But the pull for me and the external validation was one. I really need to prove it to myself. I think I'd come from a dark place where I'm like. I feel stuck in this career path I'd chosen. I think I'm capable of more. And I feel like there's something. There's a better life that I want. And I think there's more that I want to do. Am I just completely delusional? I don't know. And so I think that first year was meaning to prove to myself that no, like, I was right to bet on myself. Like, yes, there's all these things that are going wrong, but like I, I now know for myself that I can build a seven figure business, and that was enough confidence in myself to continue the journey versus I think for me, if I didn't do that, if I only got to, you know, if I just kept freelancing for another three years, I think that flame for me would have died and I would have gone down a different path.

[00:08:10] Harry Morton: And you mentioned the male female. I'm really interested. Like what? How had it being a woman founder shape the way that you went building your business?

[00:08:20] Jess Chan: Um, I don't know that it was a conscious decision. I mean, I think honestly, the last few years is probably when I felt safe enough through my personal relationship, but also through my own work of being a woman in business versus a woman trying to be a man in business. I think that's a really important differentiation where like, honestly, for the first few years, I think I was just being a man in business in the sense where I'm like, I valued myself off the things that men are valued off of. I led the way that men lead, which is you're coming in might be more confident, like you're kind of commanding the room. And so I don't know that I was truly a woman in business. And until the last two years when I learned drop in and say, what are the things about being a woman that's uniquely powerful? Like, I think women are really, really great at harmonizing. I think they're really beautiful at creating safety within a team. I think they're really beautiful at truly empathizing in a deep way and making everyone feel seen and understood. And how do we how do I take those traits of being a woman and apply them in a business setting? And how do I use that to create a unique experience for our clients? How do I use that to create a unique experience for our team? What kind of values do I want to set? But that didn't happen until the last, maybe two years. Before that, it was still masculine forms of success.

[00:09:43] Harry Morton: Yeah. That's awesome.

[00:09:44] Jackie: Can I can I jump in and ask a quick question there? Because I'm curious about how you feel looking back on that time when you prioritized the, like, masculine energy. Is that something that you, I guess, regret? Or is it more just like it makes you realize that you hadn't really found who you were as a leader yet you were relying on what was present in the space already.

[00:10:07] Jess Chan: I don't regret it. I think it was a part of my journey. And I think if I'm being honest, it's really hard to be a woman in business. I can do the masculine thing and like, exceed and succeed in the business world. And I think a lot of women have succeeded in the business world, but they've had to put on like the masculine armor or the masculine way of leading to succeed in that, because that's what's accepted and that's what's perceived as like strength and like, I think I needed to go through the journey of, wait, I can do it as a I can do as a man. I've made my mark. And now now that I've, like, built the structure, now that I'm confident what I'm able to accomplish, now that I know I can grind like I know I can, no, I can do the 16 hour days. I know I can hit all the revenue benchmarks, I know I can come in hot and, like, make a statement and like, do all those things. Now that I know that I've created my own space to soften and I think to be soft without the strength is not leadership either.

[00:11:08] Jess Chan: I think there's a misconception around feminine energy, which is like it's soft, it's fluffy, it's fairly, it's it's weak. Maybe it's like it's just there for the good times. But feminine leadership is so deeply strong. Like if we think about, like the grandmother of a house old, like there's a deep strength in, like, wisdom to that leadership. For me, I need you to go through the journey of learning how to be strong so that I could be soft, because I do think that we have to be honest that, like, entrepreneurship is primarily male dominated, and that's not a bad thing, but that is what is known. That is what's easily recognized as strength. That's what's easily recognized as success. And if we want to change that or do something different. There it is. It is difficult to introduce that space. And I think for me, I need to do it by like, I can play this game your way. Now that I've proven that now I'm going to play the game my way.

[00:12:06] Harry Morton: I don't want to say me as well, because I'm I don't even know. But I'm not a woman. But like all I can say is I can just relate to so much of what you said because, like, I'm not like a like I was not the captain of the rugby team at school. I was not like the frat boy. I was not the kind of I'm not like a super. I was raised by women. I'm not like super heavy, hardcore masculine because I figured you had to be that in order to succeed. And what I found is actually leaning into who I am, which is actually just more introverted and actually emotionally sensitive and things like that. Once I just kind of just go, cool, that's who I am. That's what I'm going to do. Suddenly everything starts slotting into place and it all makes sense. And actually, you can be a really good leader. And I can't pretend there's not the massive, testosterone fueled ego energy there as well. That's the chip on the shoulder part that wants to make shitloads of money. But anyway, I just think that's really, really interesting.

[00:12:52] Jess Chan: I actually think it brings up a really good point, which is I always use the term masculine and feminine instead of men and women, because I think it's more about bringing in the energy of feminine leadership into entrepreneurship. And I think business and the world could use more of that.

[00:13:09] Harry Morton: You know, the sort of ego led kind of growth or growth sake like, revenue chasing kind of mindset. Um, also like as a Brit who can kind of relate to the Canadian sensibility, at least in some sense, like we have a little bit in common. I feel like it feels that also feels that something like it feels like it's less of that kind of like ultra ambitious, ultra grow at all costs, ultra like, you know, uh, make loads of money and shout about it than US culture. And so like, I'm like, maybe the combo like female and Canadian.

[00:13:47] Jess Chan: And Asian like we didn't even talk about the Asian side of things, which is like its own type, like its own cultural like elements there. And so it's an interesting thing, like the rise of China. And I feel like us was in power for so long that like, we forgot that it's just one country with its own culture, with its own values, and it's not the way um, and now there's like the rise of China and just different, more things happening in the world that I feel like there's a there's an introduction of different ways to live and a different mindset.

[00:14:19] Harry Morton: What gives you the confidence that, like the way you feel about money and your attitude towards it and the fact that like more won't make you happier, essentially. Like, let's just boil it down to that kind of like basic statement. What gives you the confidence that you're right?

[00:14:31] Jess Chan: I love this question. Um.

[00:14:34] Harry Morton: I just like I think it's a douchey question to ask, but.

[00:14:37] Jess Chan: I, I wouldn't say I'm right. I think I have a really interesting perspective that I'm bringing to the table that other people should take the time to think for themselves and reflect on, to decide if it's right for them. And it's just an idea, like if we're talking about intellectual curiosity, it's like you as an individual, hey, you've been chasing this concept of exiting for $100 million and you think it's all going to be amazing afterwards. My challenge to you as a listener is like, do you have the courage to entertain this perspective that I'm bringing to the table for yourself? And do you have the courage to maybe realize that you were wrong?

[00:15:17] Harry Morton: So how did you come to to kind of reevaluate then the importance of, um, wealth versus profit?

[00:15:24] Jess Chan: I think there's there's revenue and there's profit and then there's wealth. I was also in an industry where no one talked about profit, which is kind of wild. Now, looking back, I've always been a very principles first person. Like my background is in math. Like where? Like we start from the base foundations and like build up from there. So that's just how my brain works. But in the industry that I like started my career and no one talked about profit. No one talked about a business model. No one talked about knowing your customer and solving a problem and servicing them. Which is to me, the core foundations of any business that you build. Everything was about revenue and growth and ads and marketing. I think I always felt like something feels off, but also this seems to be what everyone's caring about. And then I think the industry started shifting, but also myself as well, where I now experienced. Here's what it's like when you're just chasing revenue. You're always chasing after something and always hoping that there's a payday at the end of the day, because no one can live off of revenue like it is 100% of vanity metric. Um, profit is. It's what you can live after. There's there's some substance to that. And so that's when I realized I'm like, I've lived a life of living off of revenue, which is your burnt out. You're constantly chasing something.

[00:16:38] Jess Chan: You're trying to run off of fumes and convince yourself things are doing good. When you don't feel good and like the reality doesn't feel that way. But like everyone's saying that you're growing really fast. And so I'm like, I've lived the revenue lifestyle, but I'd really like to enjoy the profit lifestyle. And that's when I was like, there was substance, there was groundedness. There was like something to stand on. Like we could actually build from profit. Um, there was foundations. And so year 3 to 4 was about living from profit. And the last two years when I met, uh, Noel, my life partner is. That's when I think I've actually experienced wealth. And wealth is so different than than either of those two. Wealth is a sense of complete abundance and contentment and not needing anything more. Um, and that is probably when my relationship to money shifted, where I could see that instead of chasing money or trying to make money, it was more about how do I live a life in which I just wake up every day? I'm so excited. I love building things. I'm working with people that I love, and I'm just excited to create. And as long as I'm in that state. Money just comes into our lives as fuel to continue doing more of what we want to do. Um, and that's probably when my, my relationship with money itself shifted the most.

[00:18:06] Harry Morton: And how how is your business and your satisfaction around it all changed since that kind of shift?

[00:18:14] Jess Chan: It's been so much more peaceful. Um, I won't say that there aren't stressors like there's we're still business, so there's still those months where you're like, oh my God, what is happening? Um, and like, we've been through the tariffs, we've been through Covid, we've been through E-com has E-com has really taken a beating the last few years. And so there's just the emotions of running through that. But the shift has been I no longer feel like I am dying or everything is going down or my life is going down. When the business is like now, it becomes a, hey, this is a really stressful business problem and like, we should really solve for this, and this kind of sucks. Like, we'll get through it. We've gone through this before. Um, but, like, yeah, it's tough. Before it was oh my god. Like, is this the end? I'm like, I thought, I thought we had a good run. Oh my God, we're not gonna make it. I'm like, oh my God, did I do everything wrong? Did I fail? Like, did I set everything up incorrectly? Like, is this, you know, there was a sense of collapse that would happen. Now it's more of like, yeah, that's a business problem. But life is still good. Um, there's still a lot of other things that are succeeding at the same time. Um, there's a diversification of where I place my sense of, like, safety, where I place my sense of identity, where I place my sense of value. Um, so when when one thing is going wrong, it's not like everything in my life or my sense of self is collapsing, which I think is which I think is what a lot of entrepreneurs go through in that first year or two, which is what makes entrepreneurship so hard. It's never about the business problem. It's like every time your business goes up and down and it will because it's year one. Your sense of value and success in life also go up and down in that entire process, and that is what creates the suffering.

[00:20:04] Harry Morton: Yeah, I can't say that I'm free from that, from that feeling. But but it's hard. Yes, it is hard.

[00:20:12] Jess Chan: I've taken a lot of inner work, a lot of medicine. The biggest lesson I would say is to to break free of that. It's less to do with the business. Um, and how much success the business is having and has everything to do with changing my relationship to the business and changing my relationship with money. And once my relationship changes, the business has always succeeded. More after that.

[00:20:36] Harry Morton: Here's something really valuable in Jess's story. By getting caught up in the numbers game, she wasn't just running her business in an unsustainable way. She was also burying the part of herself that drove her to be an entrepreneur in the first place, which wasn't even the classic chip on the shoulder situation, by the way.

[00:20:52] Jess Chan: I grew up in a very nice, like suburban little town outside of Toronto called Markham. My parents had immigrated here since since high school, university kind of era. So I'm second gen and they did such an incredible job raising me. Like, I think when I look back, I really feel like I had the perfect childhood, um, in that, you know, I was surrounded by a lot of friends. So it was a really, really beautiful childhood. And also it was so abundant. And it was only looking back now as an adult, that I realized my parents never actually broke six figures in household income until probably the last few years before retirement, which was like 5 or 6 years ago. So looking back, like having my perspective now of success and ambition and what a good life looks like. And then looking back on how incredible that childhood felt, and now having the adult brain to reconcile that, like the abundance did not come from having a lot of money, but I never felt like we worried about money. I think it was one of the the most incredible things that my, my parents really accomplished in the life that they created.

[00:22:03] Harry Morton: So then where did the drive come from? If like you've got parents that are like providing a wonderful, comfortable environment for you. Like there's this kind of narrative that like, you know, that that that drive comes from like struggle, right? So I wonder, like, where did that kind of, like ambition come from for you?

[00:22:22] Jess Chan: Yeah, it's funny because this is actually a conversation I've had a lot with my mom. Um, and it brings up the question of nature versus nurture. I always had a really deep desire to create, and I don't know that I would I would have articulated that when I was younger, but the desire to just create and make things explore and adventure and just be curious about the world.

[00:22:42] Harry Morton: That drive could have taken you in a ton of different directions. So what attracted you to entrepreneurship?

[00:22:47] Jess Chan: Um, I mean, entrepreneurship, I think I really stumbled into, um. I was pretty, like, average kid. I wish I had those cool stories where I was like, I was always an entrepreneur at heart, and I always had my lemonade stand going. And when I was seven, and that definitely wasn't the case. I was just like a good, normal kid. The story in our home is that I was a very average kid in elementary school. I would join sports teams and get cut. I was like the bench kid. I would get 70s and everything. There was like nothing remarkable happening. And then when I graduated from grade eight, we went to Hong Kong to visit some family, and they were taking us on those tour buses and we had to buy these like ginseng pills. I don't know if I don't know if anyone knows about Asian tour buses, but they're basically giant affiliate programs. The most well-orchestrated ones, like affiliate program managers and Income have nothing on these Asian tour buses. But, um, we ended up with like $2,000 worth of these ginseng pills and their supplements. And so I was taking them throughout high school, and something. I just became smart like. I became athletic overnight. Like from from grade eight was average. And then grade nine. Suddenly I was like, I'm getting 90s and everything. I'm super competitive. I'm on like every sports team. So to this day, I still take those ginseng pills. Um, I will swear by them. I don't think there's any medicinal scientific background behind them, but amazing.

[00:24:05] Harry Morton: I'm immediately feeding my kids nothing but ginseng for the rest of their childhoods.

[00:24:09] Jess Chan: Yeah, we call them the smart pills at home.

[00:24:11] Harry Morton: Since reconnecting with a more feminine style of leadership and letting go of the need to prove herself through numbers, just as found she's not just better off financially, she's also honoring the part of herself that simply wants to create stuff. And the result of that is that her business, her life, it all feels more aligned, more satisfying.

[00:24:30] Jackie: Something I've been wondering about is like, um, I guess the impact that it has on your interactions with people to lean more into the feminine side of things because obviously, uh, the reason that you were even leaning into the, the masculine side of, of, of leadership and entrepreneurship is because it's like prevalent. So when you come into a space and you say, uh, actually I'm going to do things a little bit differently. Do you find that it's been harder to navigate or is it? I feel like it could go either way. It could be like harder to navigate because, you know, people are like, whoa, change. But then at the same time it's like, uh oh innovation or oh, that's different. So that's respectable. I'm wondering what kind of response you get.

[00:25:14] Jess Chan: That's a great question. Um, so I'm super lucky because my team is incredible and I found the right people like Rachel has always been so supportive. And also, she also embodies a lot of this as well. And so it was more about us just deepening in those values together. So it's actually been stronger for our team culture. And we've been able to attract and retain our team for years. And um, they, they really appreciate a lot of them have come from companies where they were like, just push, like working to the bone and we just value for output. And so, um, they, I feel really lucky that they appreciate this form of leadership that in this type of culture. Um, I think in terms of sales and clients and things like that, I think it has it's a really great question because I think it naturally attracts the right people and repels the right, the same people or different people who don't align. And so there has been there's probably been things that we lost out on because we didn't do the rah rah, like, hey, we're going to puff up our chest and like prove ourselves in those ways.

[00:26:22] Jess Chan: But at the same time, those people we have learned over the years are usually the ones that we struggle with or like create cultural problems when they come in as clients because there's a misalignment in how they interact with our team, or the types of results that they're expecting, what they want to see in business. And that's great because it actually helps us weed out the people that we naturally wouldn't have been able to work with for a long time anyway. But at the same time, it's attracted more of the right people, and it's also made those relationships so much more potent. We have vendors and partners that will stay with us for years that are like ride or die. And I don't think that we would have those relationships if we if we weren't leading from this space. And I wasn't leaning from the space and we didn't have this culture. Um, and I think we quote unquote profit a lot more from having a handful of those relationships than all the people we would attract from having all the right, right signals.

[00:27:23] Jackie: In terms of like, business, too. And like your satisfaction from being an entrepreneur. Is it more rewarding in that sense to like leaning into yourself and being able to work with the people who align better with you? Like, does it feel better and like less burnout?

[00:27:39] Jess Chan: Yeah. I mean, it feels so much better. Like I really do. Wait. Like I still have my. Obviously. Still my hard days. Still my days. Like, oh my God, what are we doing? But I feel like I can breathe and everything feels like. It's like I don't feel like I'm working. I don't feel like I'm being an entrepreneur. Like I feel like I'm just living my life. And we happen to have some businesses and they happen to be doing well. And I get to work with the people that I love and care about. Um, and I think it's like, it's exhausting to not be yourself. Like it's exhausting to have to, like, wake up each day and be like, I'm gonna put my, like, leadership, like armor on and, like, lead the charge and like, we're gonna go inspire people and then close some sales like that adrenaline rush energy. It was great for the first year. Like I loved it, but like, it's exhausting to do that for years. Um, and I think everyone deserves to just be themselves, just be themselves and like, have success come from that? How do you recommend ten out of ten Yelp review?

[00:28:36] Harry Morton: Yeah, yeah. Okay. I'm gonna call out something right now that you've probably already been thinking to yourself. We're unpacking why numbers shouldn't define success on a podcast that, let's be honest, kind of revolves around defining success by numbers. Also, it seems because transparency with money can be an excuse to brag, but it really is valuable. We believe that. Or we wouldn't have made this podcast and Jess believes it too.

[00:29:01] Jess Chan: Here's why I think transparency with money is important, because when we're not, we are leading other people down the wrong path. I think if someone has exited for 100 million and they're not honest about how their life feels like their expectations versus how it actually is now, the things that they struggled with were now selling an idea of what that finish line looks like that isn't necessarily honest and isn't necessarily real. And because we're selling that idea in that lifestyle, you're now. We now have more young entrepreneurs who are going to go down that same path expecting that same thing, because they were sold on this idea. Like my partner and I, we spend a lot of time talking about our intention with making money, like we know how much of it goes to family. We know how much of it goes to creating security. We know how much of it goes to like, we just want enjoy life and have fun. But the intention is really clear. Um, so I think the transparency is part of just being a good human and like, helping fellow humans and not selling an idea that might do other people harm or might be a little bit misleading or might hurt people. And like, I think we can always share that experience honestly. So other people can decide for themselves if that's the journey that they want to take.

[00:30:42] Harry Morton: What feels like real success to you today?

[00:30:45] Jess Chan: Freedom to create is probably my core need as a human. It is a freedom to create a business. It can be the freedom to create like a book, like I want to write a book one day. It's also the freedom to create a team. It's also the freedom to create a really healthy environment for freedom, to create a home, a family, an adventure. And as soon as I lose that freedom to create, then nothing else matters to me.

[00:31:08] Harry Morton: This whole business journey has run in parallel with her personal finance evolution, which I said, we're going to get to. And now we are. And by the way, if you've ever wondered what it's like inside of Hampton, which, by the way, is the private, highly vetted community of founders that creates this podcast. If you've ever wondered what it's like on the inside of that. This is exactly the topic that I talk about with my core group all of the time. So my core group is like a collection of people. There's like six of us. We meet every single month. In our case, it's online, but a bunch of these happen in person. But anyway, we build a bunch of trust with each other over time. I know them all incredibly well. Their their personal finance situation, their business situation, all kinds of personal details that, frankly, we don't normally share with many people. And that built trust means that I share everything about the way that I run the numbers inside of my company, what I pay myself, how I manage my personal finances, whether I should reinvest this amount into the business, whether I should invest this money in ETFs or whatever else.

[00:32:11] Harry Morton: You know, I workshop all of these things around my personal finance, and these are really tricky, sticky subjects that are really hard to talk about with people outside of the business world. Like, I can't talk to my family members about this stuff. They don't understand, and many of my friends don't have to manage a lot of this stuff either. And so having that community, that small group of people that I really know and trust very well to be able to share all this intimate details in my life and workshop ideas and solutions and to work through problems together is incredibly valuable. So if that sounds like something that's interesting to you, you should go and check it out. It's at Join Hampton. Com like I said, mine right now is virtual because I'm based in the UK. If you're in the US, there are a ton of like in-person, uh, core groups, and I can't speak of them highly enough. It's amazing if you want to go and check it out, join Hampton. So anyway, back to Jess and her personal finances.

[00:33:00] Jess Chan: Personally, I've never made more. Um. And kept more and also spent less, but felt more content. And it's very strange. And honestly, I have to credit most of this to my to my partner where he he's just shown me a different he has this beautiful way of relating to money where he's just able to make so much with so little. He's taught me how to spend, and I think learning how to use money as a resource is incredibly important. So in that way is like, you know, my personal income has gone up over the last few years, but by no means has it been. It's not like it's doubled. It's not like it's tripled. It's still, you know, in the six figure range. So it's a very comfortable, good, um, good income. But it's not like fuck you money. But I feel like I'm living a fuck you lifestyle in terms of contentment.

[00:33:59] Harry Morton: Tell me about your portfolio. How do you manage your money?

[00:34:03] Jess Chan: Um, it's pretty autopilot. Um, I, I'm in this because I love creating and building stuff, and so I really optimize the way I set everything up to allow me to focus all my time and energy on just building long play. So it's really just in like ETFs, um, that, that, um, that kind of run on autopilot and then have a like, like literally my parents finance manager from way back when, where I just started investing with when I was like 21. I'm like, he's just he's just accruing a little, little pile for like retirement or something like that for me. Um, but it's not honestly, it's not something that I think about on a weekly basis. It's maybe like twice a year.

[00:34:50] Harry Morton: Cool, awesome. That sounds relaxing. So, uh, tell me about your monthly spend, then. I'm interested to know, like, what your monthly spend was before, um, like, in the early years of of the business and where it's at today, because it feels like there's been a bit of a trajectory where you're, like, building up, like, you probably don't have that much access to money, and then the agency starts doing really well, and you're making more money but spending less. So I'm just, like, interested in that trajectory.

[00:35:17] Jess Chan: Yeah. No, I mean, you're spot on this trajectory. I'm trying to remember the numbers because it's like how it felt at that time. It's like it felt bigger at the time, but it could probably actually financially be small now based on where I'm at. So from a spending standpoint, I think when I first started the business, I was probably spending about like Five to 7KA month. Like, I wasn't saving a ton a ton. Um, I was also, like, really bought into the entrepreneurship lifestyle. Like, my time is money and like, I'm going to have a personal assistant and a chef and like, a personal trainer. Now I'm like, why is that valuable? Just like, just chill. Like, I just want to relax. I don't want to manage all these things to optimize my time so I can work more. So, um, at that time, it was like I was spending on those things. And then years three and four, I was also spending a good amount because, like going to restaurants a lot. I traveled a lot. Like during Covid, I was paying for both my apartment and I was like, out of the country because I didn't want to be stuck in everything. So I was always spending between like 10 to 15 K a month, maybe. And now in the last years, probably last year or two years, it's probably down to more like 5 to 6 K, maybe Okay. A month. Um, but, like, quality of life has probably gone up, like, like, 300%. Yeah.

[00:36:45] Harry Morton: Um, do you do any, any, any discretionary spending that's like different or interest? Like, are there particular things in life that you choose to spend more on?

[00:36:54] Jess Chan: Um, so, I mean, rent was actually a really big one that I overspent on for a few years. And with my partner now, he's like, yo, this is like, this makes no sense. Like just quality of life to like, how much we're spending, like, let's just. And so now we have this beautiful townhouse and a condo with all these amenities. And, um, so I brought our rent down by like 30%, um, which is probably the biggest chunk of money. And then it's a lot of honestly, it's more spending on like, family. Um, we eat at home a lot. Like, it's a beautiful experience cooking together versus, like, going out. So it's all these little things where we're now enjoying life more and spending probably 20 to 30% less on everything.

[00:37:37] Harry Morton: The other thing I wanted to reflect here is like I was that occurred to me while while you were talking is it's really, really interesting. The only other person that's that's just not bothered about the signaling that's really focused on, um, what do I need in my life to be happy? Am I there yet? And, and enjoying that and this kind of, you know, talking about abundance and so on. It's my friend Laura, Laura Roeder, um, who came on ages ago on the show. Uh, it's really interesting to me that it seemed the only people so far that have been comfortable, essentially just comfortable not saying, bro, I'm, I'm looking for the next zero. You know, I'm being like, reductive and I'm not I'm not trying to like, be rude, like disparaging to any of our previous guests here. It's just really, really interesting that it's only seemingly so far in the conversations. We've had women that are comfortable kind of speaking about money and business and success in that way. I so relate to so much of that. But there's still this thing in me that wants to go? Yes. And I want to reach for that next thing or I want to. Whatever. Whatever. Whatever. But like the kind of like caveat it with. But also I'm gonna go big. Do you know what I mean?

[00:38:46] Jess Chan: It it is interesting and I think like because I've, I've had this conversation with so many entrepreneurs and I think I always go back to like the first principles of why did we start this whole thing in the first place? Like, why? Why did we choose to be entrepreneurs? Um, because like, the truth is, most of us, if we're just playing the odds like most of us, could probably have had a higher paying cushier life working for someone else. Like whatever it takes for us to build a company, we could probably be making half $1 million salary just chillin. And so there's there's something underneath it. And so I'm always curious on like, why did we all start this? And my, my hunch is like, there was like, there's something to prove about yourself is like, hey, I wanted to see what was inside of me, or it might be something to do with, hey, I want to. I want to have full autonomy over creating the life that I want. And so I think all those questions usually lead back to, doesn't it all come down to how does life feel and who am I? I remember when I first started the entrepreneurship journey I promised. I made a promise to myself where I'm like, hey, I don't want to lose myself in this process. Like I've seen so many entrepreneurs get lost, even when I was like early on. And and so the hitting are big. I'm like, yeah, I'm like, we still want to build like an eight nine figure business and we'll still steer in that direction.

[00:40:14] Jess Chan: For years ago, I thought I was scared. If I became content, I would stop becoming ambitious. But now I really believe contentment, ambition can coexist. I think it's more about hey, aim big, but like, don't forget what really matters, which is who are you? And does life feel good? And if you're now sacrificing those two core things for the extra zero. That's when, you know, it might make sense to to take a step back, because I see so many entrepreneurs just it's like you did the thing and you just you collected all the signals. Like, now what I've seen, I've met so many entrepreneurs where they did it, like they got the $100 million exit. And then now I'm like, hey, how's life? Like, what are you up to? He's like, and they're like, I don't know who I am. I don't know how to be happy. I don't know what to do with all this money. Because in that whole process, I lost myself. And I don't even know what makes me happy anymore. So now that I have the 100 million, I don't know what to do with it. Now that all this time in freedom, I literally don't know what to do with it because I lost who I am. And it's not. Doesn't that defeat the purpose of getting the 100 million in the first place?

[00:41:19] Harry Morton: Jesse's all in on optimizing for life now and growing sustainably while being true to herself. If you want to be mega wealthy, though, according to Scott Galloway, that's not the way to do it. Listen to what he said here.