
Most people with a full-time job, 14-hour shifts, and zero business experience don't start a brand — Jesse did, and he's closing in on half a million dollars a year to prove it.
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A
Hey, founder fam. I want to talk to you about something super exciting. We're officially partnered with Omnisend, the email marketing and SMS platform built specifically for e commerce founders. We've been recommending Omnisend to founder students for a while now because it just works. Whether you're launching your first store or you're scaling to seven figures, it really helps you automate your marketing and get real results. Did you know, on average, OMNISEND customers make $68 for every $1 they spend, which is an insanely good return. And because you're part of the founder community, you get 50% off your first three months with the code. Founder50. Just head to omnisend.com founder without the e to get started. All right, now let's jump back into the show. Welcome to Little Empires, brought to you by the team at Founder at Founder. Our mission is to support the next generation of ECOM founders. And so while you may know us for interviewing some of the world's most successful entrepreneurs, this series is a little different. Little Empires shines a spotlight on the builders inside our own founder community. The entrepreneurs who are in the trenches, taking action, learning and building their businesses in real time. These aren't overnight success stories. These are real journeys, real lessons, and real founders creating their own little empires one step at a time. This podcast is proudly produced by the founder team to give our students a platform to share their experiences, wins, challenges, and honest realities of building a business from the ground up. Now, let's dive into today's episode. So, Jesse, thank you so much for taking the time, man. Excited to speak with you, dude. It's been a while.
B
Yeah, man, I'm excited to be here.
A
Little bit of context for everyone. I met Jesse on a Contiki tour. I know a lot of our community are based globally, especially in the United States, so you wouldn't probably know what a Contiki tour is, but I did one of those when I was 23, and it's like a bus full of young people and you can only join, you can only go on it if you're under 35. And I went through a big breakup and I needed a change in scenery, so I decided to do a Contiki tour around South America. Now, I just. I just made the. The quota and I was really embarrassed, so I didn't tell anyone my true age. But I. I could only do the tour if I turned 36 while I was on the tour. And it just. All the numbers lined up. So I ended up meeting Jesse on this Tour around South America. We went to Peru, Argentina and also Brazil. And it was a pretty life changing trip for me. And along the way we got to know each other. At first I didn't really want to talk about who, who, like founder or, or really what I did for work. And then we were, we were stuck in civil unrest and you took a selfie. Do you remember that selfie that you took of us, man?
B
Was that. I do think I recall that. I think it was at the karaoke bar right when we were in Puna.
A
Yeah, yeah, yeah, yeah. And you're like, man, let me tag you. And you're like, oh, dude. I'm like, man, you don't want to tag me. And then you're like, who the hell are you? What do you do? And then long story short, you know, we went our separate ways after the tour and I find out that you signed up to founder, you signed up to our coaching program, and you launch Wolf Work where we helped you. But you've, you've. You're building this incredible brand. And you know, I was really excited to hear that. I don't know the exact numbers, but you were in the bracket of doing over $250,000 a year with this brand. Corre.
B
Yep, yep. Last year we took total 450.
A
There you go. $450,000, like incredible. And you started the brand what, two years ago?
B
Yeah. Yep.
A
Okay. And you're still working in your day job, still doing fifo. So we want to talk about the real stuff. Right? So, man, first and foremost, congratulations on all of your success thus far. I'm just so proud that we were able to play just a such a tiny fraction of helping you and supporting you building this brand. But tell us, how'd you come up with the idea?
B
You know, I've been mining for 16 years and I've always struggled with the gear that we get given. It's just not suitable for the environment that we're working in. So I just went on a journey one day to solve my own problem. Going right back to that fateful night in Pune. I always wanted to do something that I could, you know, sink my creativity in and really try and build something from nothing. And that's kind of what blew my mind that night. It was just like all the planets have aligned. Like, this is exactly what I've been looking for. Like I wanted to do something, I just needed to kick up the ass to do it. And you know that that's not as vertical started. So it was like I often Think about it, it's like, it's crazy how the world works sometimes, but I didn't have the idea at that time. But, you know, the, the seed was planted in my head. I knew if I wanted to do something, this is the avenue that I was going to use to do it. So it was just a matter of time before the idea came into my mind. Then straight away I knew what I needed to do to get the thing going and that was where I looked up. Founder.
A
So you had the idea for the product and you know, wolf work, where you create really durable workwear, that's your strong point of difference and you want to scratch your own itch. How did you know it would sell?
B
Yeah. Working in the industry for so long and working with so many different people, I know for a fact that everyone has the same issue that I did. And with the mining industry and heavy industries in particular being so large in Australia, it was just a matter of developing the product and putting it in front of people's faces. And I knew that if it was good enough and it solved the problem that I wanted to solve for myself, history would be made just like that.
A
Did you speak to anybody before you said, yeah, no, this is something I want to do, or like, how did you validate it? Or you just knew, you just knew. Like, you had so much conviction. You're like, yep, this is, this is the thing.
B
No, I definitely leverage the, the feedback of the guys that I was working with at the time I started, you know, doing behind the scenes stuff like doing the product planning, talking to manufacturers, getting samples. And I, when I was ordering the samples, I made sure I had enough to give to the other guys that I work with as well. So I'd go to work and take all these samples and just give them to the guys and say, look, wear these, thrash them, tell me what you think. And it was great because I, you know, I was working right beside the guys that I was needing to get feedback off. So it was like right then and there, perfect.
A
And what were they saying?
B
This is like how stripped back it was. I was only doing it for, like, for us at that workplace then and there. I didn't even have any, any intention of, you know, making a brand or a business out of at that stage. And with the feedback they were giving me, they're like, nah, man, you got, you need to, you need to sell this. So, yeah, that's what this was like. All right. Yep. All right, guess we're going to do that then.
A
And you join the coaching Program. You work with Natasha, one of our coaches. And in your first 12 weeks of launch, I think you made $10,000. Is that correct about that, right?
B
Yeah, about that. So it feels like a long time ago now. So.
A
Yeah, so it's a couple years ago now.
B
Yeah.
A
And I'm curious, how did you get your first sale? Tell me about that first sale. Was it friends and family? Was it people you knew? Was it. Did you post it on Facebook or Instagram? Like, how'd you get your first sales?
B
I created quite a, well, I'd say a large following. I think it was like maybe 4,000 followers or something on, on Instagram while I was building up the product and building up the business. So I already had the brand at that stage and yeah, managed to get a gathering following about 4,000 people. So I thought that I was onto a winner. You know, like people are really interested in this and this is all getting exciting. I can't wait for the product to land. And then, yeah, we launched and it took three days for the first sale to come through and I was like, ah, damn it. It just goes like if you think you, you got all your ducks in a row but you, you just don't know until you first go away. So I do believe that my first one or two sales were, yeah, just, just sympathy, sympathy sales from family. But yeah, it's just a matter of getting the right ads in front of the right people and speaking the right language and then it just started to trickle in from there.
A
Now when it comes to the designs, the product, the manufacturing process, can you talk us through that a little more? Because that comes up like it's quite intimidating, you know, going to China. Did you go there? Did you meet your manufacturers before you started? Did you use Alibaba? Talk us through that part.
B
The product development is actually the part of the business that I enjoy the most. And easy. I did all of my products investigation and got found on manufacturers on Alibaba. So the way I do it is I'd simply just trawl through all the stuff they've got on there and kind of find a product that looked similar to what I wanted and then made sure that they were able to make changes and you know, iterate the product that manipulate it the way I wanted it. So yeah, I just find a product and use, you know, say they had a picture of a pair of pants on their website and I say this is what I want. These are the changes I want to make and the start process from there. Get them to make a Sample and then get it sent to me, test it, change what I need to change and then just keep iterating like that until I'm happy with it. And then push play on a bulk order.
A
And what was that bulk order? Can you talk us through the numbers if that's okay?
B
I think we launched with like six products and one of them I definitely over ordered on. But that's all right, you know, you live and learn. But like I thought with the validation that I had from my 4,000 followers, you know, that I was onto a winner and I'd definitely be able to sell a thousand of those things. And then when it came to selling them, no one wanted to buy them. So I made the mistake of not doing the correct amount of validation there. Still learning that one now, to be honest, it's still, it's hard because you think you're only making decisions based off the feedback that you have and the information you have at that time. That's it, that's all you can do. Make the best decision you can.
A
Yeah. So when it comes to the manufacturing process, roughly how much did you put towards bringing your business to life on the kind of the stock side, do you think? If you could give an estimate, launch wise?
B
Probably around 40. 40 to 50,000.
A
Yep.
B
But like I overdone it big time. The lessons came thick and fast early on in the process for sure.
A
Yeah. Now, yeah, that is a lot of stock, man.
B
Yeah, I was, I was fortunate enough that I was, you know, I had a, had a job that was, that I was able to afford to do that. I definitely don't recommend anyone else to do them. Make the mistakes that I do. Like, yeah, really negotiate for those MOQs because you're in love with the product and you think it's the best in the world, but doesn't mean anyone's going to want it. So yeah, startups as small as possible.
A
You did, over time move the stock though. It wasn't all doom and gloom. But you, I guess you got a bit of a wake up call where oftentimes people think followers equals dollars. And this is coming from, you know, like we have millions of followers on Instagram for founder. And don't get wrong, we make millions of dollars, but probably not as much as people would think. And look, it's an incredibly powerful channel, right? Incredibly, incredibly powerful channel for the brand. But you know, I think that is a, is a common thing. People think followers equals dollars and it's not always the case. So how did you get the first 4,000 followers, because that's quite large in a, in a short amount of time. What did you do?
B
So going back to the reason why I created the brand is because I had a problem that I wanted to fix. When I wanted to create a following for my brand, I just share content that I wanted to watch. So what I was using Instagram for at the time is just going on there and watching people make mistakes and making absolute idiots of themselves. That's what I found entertaining. So I just. Any, any video that I found entertaining that was, you know, related to work or to heavy industries or whatever, and it would involve like fails or people just doing funny things, I'll just reshare it. And that's all I'd done every day was just reshare like funny videos and just build up a following like that. So I, the, basically the, the page started off as entertainment, people making idiots of themselves. It was, you know, easy, easy to create a photo like that. But that's an audience of people that have come to see entertainment. They're not interested in buying my products. So this is where I went wrong. You see all these, all those 4,000 people wanted to see people making idiots themselves and all they saw was me making it either myself, trying to sell them clothes.
A
Yeah, I see. So you launched it would have been mid 2023 sub. 2 1/2 years ago, right?
B
Yeah, about that.
A
Yep. Okay, man.
B
Time flows.
A
So it's been, yeah, so it's been probably about 30 months, give or take. Yep. So you're growing the brand now what it. Let's, let's talk about kind of your first year. How did you manage it while doing fly and fry out and, and you know, like you look at your website now, it's, it's really solid, man. Like, you know, as you shared to me with me offline, you know, paid advertising is a big part of your strategy to get growth. And you know, you're, you're, you're closing in on half a million and I'm sure soon, eventually it'll be a million dollar a year business like you are on the pathway. If you keep doing what you're doing, you will get there, which is a pretty incredible feat. Right? Like only a small amount of people can build a million dollar a year business. Like I think it's under 1%. So you will get there and I, I'm actually confident you'll probably get there in the next one year, maybe or less.
B
That's the goal. I want to be there in the next year.
A
Yeah. So talk Us through that first year and managing, growing a business where you have not that much traction. You're trying to build a brand that nobody's heard of and you're trying to work in a job that like you said, you, you know, you paid pretty well in, you know, doing flying and flying out work. So, so talk us through that. Like how did you manage it? What kind of hours is required?
B
Yeah, that was a really, really hard year, man. Like I wouldn't change a thing, but it was, it was a struggle. Like I was doing 14 hour days at work and then, you know, waking up an hour early and then staying up an hour later each night. So there were some really long days trying to, and you got to fit sleeping and eating and all that kind of stuff into that as well. So while I was at work, the days were ridiculously long. That's what I wanted. I wanted the challenge. And that's the thing. Waking up every day having a challenge and being able to grow something from nothing is one of the awesomest feelings in the world. So that is what keep keeps you energized.
A
And what sort of things would you do if you've only got one to two hours a day? Like what? Where, like talk me through that because I think that's important. So you went through our six month coaching program and we, you know, helped you grow it and then talk me through, like what were you doing right within your one to two hours a
B
day I'd learn and then whatever I learned in that hour or whatever I'd implement straight away while it was fresh in my mind. So you know, I worked with my way through the modules on, on founder and you know, do a module, learn what I need to learn and then go implement whatever I learned straight away into the website, into, you know, setting up whatever straight away, just do it. And it's just almost like I found the Founder platform was just like a giant checklist. You just start at the start and just work your way through it.
A
When it came to, I guess, moving that first round of stock and MOQs, how long did that take you, man, before you had to place a new batch of orders?
B
Some of the products were more popular than others. And usual Murphy's Law, the ones that you have the least amount of are the ones you the most popular. So it wasn't, wasn't too long. More lessons that came thick and fast is, you know, I had no data of what sizes were going to be popular, what colors were going to be popular, all that. So it was, I was Just flying blind. And yeah, I learned pretty quickly what, what, what sizes I needed, what colors I needed, all the ones that I didn't have. Funnily enough, you just got to iterate as you go. And one, one thing that I have told myself a lot is don't be afraid to make mistakes, especially at the start. Because this, the mistakes you make at the start are usually when they're the most to make. If you make the same mistake further down the track, it uses you a lot more money involved. So fail fast. And it's, you know, it's not a failure if it's, if you learn from the mistake. It's only a failure if you make a mistake multiple times.
A
Yep, I agree. And it's money in the bank. All these lessons.
B
Absolutely.
A
And sometimes, sometimes like people can tell you, but it doesn't hit and learn. You don't learn as hard as you do actually feeling the pain.
B
So if you feel the pain in your wallet, then you learn, you learn pretty quick.
A
Yeah, exactly. So to tell me like along this journey, what has been some of like the greatest learnings or the most painful things? So you talked about that not having much time, having one to two hours a day, working 14 hour days and juggling while trying to grow this business. What were some really painful things, some really big challenges of trying to grow this brand or things where you've like, you've learned big time?
B
Definitely the thing that I've struggled with the most and still hurts the most is when I disappoint my, my customers. Whether that be, you know, through a folding product or we've missed the mark on a delivery or basically if I've upset one of my customers, that's the thing that hurts me the most. You really get attached and you get a kick out of doing positive things for people. And as, as soon as you know that back script flips, flips for whatever reason it can, most of the time it's out of your control anyway. It still hurts a lot. And I've gotten a lot better at accepting things that are out of my control. But it still hurts, man. I did a real kick out of making people happy. And as soon as it's shoes on the other foot, it's like, ah, yeah,
A
it, I know exactly what you're talking about. I take reputation incredibly seriously and I'm the same as founder, right. Like if, if somebody shared a really poor experience, it hurts man, it hurts big time.
B
It's an opportunity to grow there and learn. So you got to take the silver linings with everything.
A
Yeah, I agree. So you're not a fashion designer, but you said you really enjoy that part. So do you design, do you design the. Or do you outsource that? Or how do you work out how to design the year?
B
I'm the furthest thing from a fashion designer. You can probably get polo shirts and, and rugby shorts year round pretty much, mate. So I don't do any, any design. I just. The thing that I'm looking for is function and comfort. So if it doesn't need to be there, it's gone. And if it's. If it's there, it needs to serve a purpose. That's. That's as far as my designing goes, mate.
A
So this is how you're differentiating in the marketplace, Function and comfort.
B
Yep. And then like having a bit of a different voice and a different personality as well is a big thing because especially when it comes to B2B and all these other big workwear brands, they're also boring and sterile. So I think having a bit of, a bit of attitude and a lot of personality in your brand makes you stack these stick out pretty quick.
A
So big channel for you is pay advertising on the direct to consumer side. But you also have a B2B arm as well, right?
B
Yeah, we just really started leaning into that in the last year. We do supply a couple of little mining companies and the small medium tier mining companies for all of their employees get, which is great for the income and then the turnover, but then also great for gathering feedback and iterating the products to be even better as well. Because you know, you've got all those people on the floor that, that are basically testing your product for you and
A
you do customization and personalization.
B
Yep. Can do, Yep. We can do like logos and stuff. So.
A
But you would have to place that with your manufacturer first up, right?
B
Yeah, like for, for bulk orders, for orders over X amount. Then we do it at the manufacturer level, which is the most convenient and the most cost effective. But for small outfits, we've got a few options that we can use for local embroidery as well.
A
Okay, so you've got the B2B happening and then you've got. And you're leaning into. And then you've got the direct to consumer side. And you said a big part of what is also growing the brand is paid advertising. So talk me through that. Because you said it took you three days to get your first customer and you think it was a sympathy one. Um, but then eventually start to get ads working. So talk me through that. And you start to get messaging working or, or content and creative working. Talk me through that because I think that's really valuable to people because a lot of brands start out this way. That's why I'm so passionate about this particular show. Little Empires is we're speaking to people in our community that are in the trenches actually doing it. And yes, we have these incredible stories of founders that have exceptional success, like they build a hundred million dollar business in six years or whatever. But these are the real grassroots stories as well, because we want to tell those stories as well. Talk me through. Because it is, it is, it, it is, it is common. Like we do hear this.
B
Yeah. So big part of it early in the piece is I didn't have, I didn't have the info that I needed to make good decisions. So as time goes on, you just pick up more and more and then you start thinking, you know, you start to understand the metrics and you start an ad and it just goes berserk. And you're like, okay, that one seemed to work all right, now let's make a different, make a different iteration of it and try it over here. A different product. So you just listen, listen to yourself and figure out what works and what doesn't. And probably the biggest return that we've got lately is just changing from static ads to UGC ads. We made a massive push into ugc probably around October last year, we started pushing UGC ads a lot more. And game changer right there. Going from static ads, mannequin shots of pictures of clothes is not very interesting. But having someone filming themselves and talking through the product and the way it fits is exactly what everyone here and wanted to see. And it's, it was just like straight away, overnight difference.
A
That's awesome. And in that first few months, even to do like, I think it was, yeah, 12 grand or 15 grand or whatever the number was in that first few months. What adds or what was the first ad that worked where you're just like, oh, okay, now I can keep growing this.
B
Back then, just the fact that it was making sales was classed as, as working, wasn't doing it profitably, but it was, you know, people were buying, buying stuff because of it. So that was working in my books.
A
Yeah, there you go.
B
Okay, going back now. And if I, if I knew, I knew now I was like, ah, that's not working at all. That's, you know, when you start thinking about, you know, CPAs and ROAS and cost per each and all that and it's like, man, I would have been more miles off the track. The fact that, you know, I had had some conversions coming in, it's like, yes. Yeah.
A
Wow. Okay, there you go. So when it comes to traction, then at what stage did you really feel like, okay, I see how I can get this into a business where I can go full time. Now you haven't gone full time yet, but at what point were you just like, yep, you know what, I can see it.
B
But I think from day one, I knew that I had something and I knew from day one that this is going to be a long term thing to pull off. But I was confident and I was prepared to put in the work. So, yeah, day one, man, I knew that it was something I wanted to do and it was going to work. I just needed to execute it. Regardless of how long that took.
A
I respect that. Dude. When I started Found a Man, you know, I didn't have any form. Like, if you look at a racehorse, I had no form whatsoever to, you know, build a business in any, any capacity, let alone one that is doing well.
B
And if that's a form of. I was, I was a donkey.
A
Yeah, me too. Me too. And I always knew, though, deep inside of me, man, like somewhere inside of me, I always knew that even then I didn't have form. Even though I was doing work in my 9 to 5 job that I didn't particularly enjoy. And it was. I didn't feel like it was me and I didn't feel like I wasn't excited about it. And the work didn't really get me out of bed excited. I always knew deep down that I could be and do so much more. There was something inside of me. It was like this subconscious thing inside of me. And it sounds like you have that too. Like, don't get me wrong, you love flying fly at work. It is a part of it you're passionate about. But it sounds like deep down there was something inside of you that was like, you know what? I can build something of my own. I can do this.
B
Yeah, I was. You know, I've been in the industry for a long time, so I'd kind of reached my glass ceiling and I needed something new to sink my teeth into. And, man, I've done that for sure.
A
So you said you guys are doing, you know, last year, you're probably averaging at the moment, 30, $40,000 a month on average. You're not in the position yet to go full time. When do you think you will feel comfortable to go all in, leave your job and this is Your full time gig.
B
To be honest, I probably could step away and go full time in it within the next year or two. But to achieve the target, so I want to achieve, I think I need to help carry on working two jobs and at the moment it's fine. I'm managing it and getting by. I'm starting to now bring people into the business as well that can help me. So it makes it a lot easier being able to delegate things and then while working two jobs.
A
So I'm really curious here because most people at your stage probably would have gone full time by now. So talk me through like what are the ambitious goals and then I'd love to unpack like the support you have as well right now.
B
Yeah. So I. Everyone's got a, a number in their mind that they want to achieve before they call themselves a success. That number for me is quite high and on our current trajectory I need to be working two jobs for another two or three years to be able to reach that number. That is where I won't have to downgrade my lifestyle to, to, to go back to being full back into one one. Rog.
A
Got you. I understand. So, so to maintain your lifestyle. This is, this is really cool. Like thank you for being so open, honest and transparent dude. Because people don't talk about this stuff. Right. So if we wind back a second, you've got your goals, big trajectory you want to hit. So you're currently reinvesting basically every dollar that you're, you're getting from the business back into the business and eventually you want to get to a point where you can draw a really healthy salary and income from it when it comes to reinvestment. Now you're starting to delegate. Talk me through. What roles do you have in the business where you're getting leverage?
B
Yeah, I've got an agency helping with my Facebook ads. They were running my Google Ads as well, but I've since taken that back over. They do my email marketing and ads so I've got a lot more knowledge and the fast paced nature of meta so they're handling that for me at the moment. I do intend to bring that back in house in the next year or two I'd say. But I'm still going through the journey myself of learning more in that space. It's great that I can learn off them and then as well as do training on the side that I can compare with what they're doing and also with working fly and fly out. I am offline for 12 to 14 hours at a time. Which is with the business getting to the size it is now, it's not good to have all those people waiting in your inbox that need to have their stuff sorted out. So I've actually just this week taken on a full time V8 which has been an absolute game changer straight away. Just being able to focus my energy into things that move the needle in the business and not have to worry about processing exchanges and size of this and small level customer service stuff. Being able to delegate that is freed up so much time for me to focus on the good stuff.
A
Yeah, no, I remember hiring my first video as game changing. Right. That's awesome. How exciting.
B
On the social media side too. Sorry, I've got one of my best friends, his partner is helping me with the social media as well. So basically make me humiliating myself on the, on the social networks is all. There's all her nice work. So, yeah. So I've got three different avenues getting outside of help at the moment which is, yeah, all the parts that need to be continued but I can't do at a continued capacity. So.
A
So, dude, look, we have to work towards wrapping up. This has been incredible interview. So much fun. It's just cool to interview someone that I know. I've met you before, we've hung out, we've drank beers together and it's so cool to see, it's so cool to see your success the, you know, these. These years later and just play such a small part in it. So a couple last questions. One, what was the biggest thing you took from working with us at Founder and engaging in our coaching program? And then two, what's next? What are you most excited about to get to? You know, you said you want to get to a million plus. What do you think? What do you think that thing is that's going to help you get there?
B
Yeah, well, the first one, the thing I took away the most from the mentorship was just having someone in your corner that was there that you can bounce ideas off. I didn't have any experience in anything to do with E commerce, like not a single thing right from day one. So there was a lot, a lot of things that I was indecisive about and just had absolutely no idea and just being able to talk to Tash about it and just be open and vulnerable like I don't know what I'm talking about, but this is what I'm thinking and just being, having, being able to have something to talk about like that in your corner and at all times just having the knowledge Right there. It helped a lot. And I can guarantee I wouldn't both wouldn't be what it is today if I didn't have that right at the start. Because you know when, when it's all new and fresh, the amount of thoughts that's going around your head that you need to get out and if you don't have anyone to talk to, then that's where they stay and don't do anything about it. So it's almost a good way to be accountable as well. I'll still go back to the founder of Modules now and just get refreshes and that. So it's awesome. Well, number two, I just want to carry on growing up the way it is, carry on making people happy. That's the main thing. I get a kick out of it if other people are getting a kick out of it. And it's a different way of bringing value, value to people's lives. So bring it on.
A
Well, man, look, congratulations on all of your success thus far. And yeah, it's been awesome to see and hear and get the latest update on how you're going. So the. Dude, you're killing it. And I know if you keep at this trajectory, you'll be there and your goals, no time. So well done, dude. You've earned it.
B
Thanks, doc. Appreciate it, buddy.
A
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Episode 646: How Jesse Built A $450K/Year Brand Whilst Still Working in the Mines
Date: April 1, 2026
Guest: Jesse (Founder of Wolf Workwear)
Host: Nathan Chan
In this episode, Nathan Chan speaks with Jesse, founder of Wolf Workwear, about his journey from being a FIFO (fly-in-fly-out) mine worker to launching a workwear brand generating $450,000/year—all while keeping his demanding day job. The conversation covers the reality of building a business from scratch, overcoming challenges of time and resource constraints, and actionable lessons on validation, marketing, and growth. This “Little Empires” series episode spotlights real founders in the trenches, detailing Jesse's hands-on approach, painful mistakes, and hard-won breakthroughs.
On Validation:
“I'd go to work and take all these samples and just give them to the guys and say, look, wear these, thrash them, tell me what you think.”
— Jesse (06:01)
On Social Media Reality:
“All those 4,000 people wanted to see people making idiots of themselves and all they saw was me making it either myself, trying to sell them clothes.”
— Jesse (12:44)
On Overorder Regret:
“I thought… I’d definitely be able to sell a thousand of those things. And then when it came to selling them, no one wanted to buy them.”
— Jesse (09:34)
On Time Management:
“I was doing 14 hour days at work… waking up an hour early and then staying up an hour later each night.”
— Jesse (14:19)
On Customer Disappointment:
“If I've upset one of my customers, that’s the thing that hurts me the most… you get a kick out of making people happy. And as soon as it’s shoes on the other foot, it’s like, ah.”
— Jesse (17:37)
On Brand Differentiation:
“Having a bit of attitude and a lot of personality in your brand makes you stand out pretty quick.”
— Jesse (19:14)
On UGC Advertising Breakthrough:
“Going from static ads, mannequin shots… to [UGC] overnight difference.”
— Jesse (22:27)
On Support:
“Just having someone in your corner… I can guarantee Wolf Work wouldn’t be what it is today if I didn’t have that right at the start.”
— Jesse (29:14)
Jesse’s story is a hands-on blueprint for resourceful entrepreneurs managing side hustles alongside demanding day jobs. He demonstrates the critical importance of customer feedback, iterative learning, effective time management, and being unafraid to make mistakes early to set up for long-term success. The pivot to UGC ads, the double-edged sword of social media, and the real emotional journey of entrepreneurship are unpacked with refreshing honesty, offering actionable takeaways for anyone building their own “little empire.”