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April 20, 2023

How Portland Leather Goods Scaled a 9-Figure DTC Bag Brand with Curtis Matsko — EP 022

Episode 22
Curtis Matsko

Listen on:


Adam Robinson: Welcome to Ten Years In The Making. This episode, I've been hounding this guy for literally five months. It's Curtis Matsko. He is the founder and CEO of Portland Leather Goods. So, tell me how hard you're killing it so everyone who's listening to this right now will keep listening.

Curtis Matsko: Okay.

Adam Robinson: Give me just like what I heard.

Curtis Matsko: Okay. I will give you that but I've heard your podcast is amazing. You almost seemed a little bit nervous there as you're introducing me. Let me tell you in one minute about how we are killing it. Portland Leather Goods is killing it. It's from a garage to we're going to make about 2.1 million bags this year. We're 120 million plus our new, which is our new shoe company, which went from 0 to 10 million in less than eight months. It's still amazing. We're growing as fast as we can make the bags, really. We've hit a niche in the market that people are just obsessed about our product, which is pretty nice.

Adam Robinson: I mean, unbelievable. I want to dig into that but the first thing I want to dig into I didn't know your origin story until you told my wife, Helen, at the after-party at The Triple Whale event. It's f*cking bananas. Can you just like share where Portland Leather Goods came from, please?

Curtis Matsko: I can. I've never really put this on a podcast before. The truth is I'm a true entrepreneur. I truly believe that class clowns are the perfect entrepreneurs. And I was the class clown, I was class personality. I was all of those things. And the reason that I believe that is because we seek attention, which is perfect for Internet marketing. You have to have attention. We're disruptive, which is what it is. You're cheerful and you don't like authority. And that's been me my entire life. I'm not going to go out and get a job. I'm going to create my own company. So, I created a couple of companies. They did very, very well. And then I went through a period of deciding that it was a little bit too much fun to drink and play around than to do anything. So, about ten-and-a-half years ago, which is perfect for your podcast, where the name is absolutely perfect, I completely stopped drinking. I met a wonderful young lady and just took it easy. Just try not to take over the world, which is my natural tendency. And we got in a little fight one time and I said, “Quit your job and I will start up a company selling things on the Internet and we’ll make $100 million.”

And she said, “What? That sounds crazy. That's not possible.” And I'm like, “I'm actually good at this. I've just been kicked back doing a lot of yoga lately,” and I'm like, “Just quit your job and trust me.” She said, “What do I have to do?” And I said, “I will promise things to people. You just have to make sure they actually get done. I will say, I am going to email Adam, ‘Adam I'm always going to forget to email you.’ I am going to do this. I'm always going, ‘I'm not going to do that.’” And then I walked into a little store, bought a piece of leather, and went home, spent about two weeks designing a little leather journal, and I walked upstairs and showed it to my girlfriend and said, “This thing is genius. This is amazing.” And we started selling it, went on to Etsy, and within a year became a top ten all-time seller, literally broke Etsy. Moved. Started making everything in Portland, hiring just 80, 90 people to make all the products that were needed for us.

Adam Robinson: And this was only the journal first?

Curtis Matsko: We started on the journal because it's something I wanted.

Adam Robinson: What store did you walk into to buy a piece of leather? What does that even mean?

Curtis Matsko: There's that store called Oregon Leather Goods or Oregon Leather actually and they just sell like old scraps of leather. And I literally just didn't know what to buy. So, I bought one. I actually went home and then came back the next day and said, “Well, that one sucked. Is there anyone that knows anything about this?” And they gave me the owner's daughter and she explained about leather to me and I went home and I made this refillable journal. It's because what I realized is there was a place in the market that no one had. Because if you literally go to buy something that's leather, you can go online and you don't really know if it's leather or not, especially like a refillable journal. And I realized that everything that was valuable if you watch Indiana Jones, all the secrets are always in a little leather journal. And if you read The Lord of the Rings, Bilbo put everything in the leather journal and you go to a store and you couldn't find it. And I'm like, “This is genius. I'm going to build a company on a leather journal,” and my cousin, who is an incredibly brilliant, wealthy guy, said, “This is a stupid idea.”

And that challenge right there pissed me off so bad that I went onto Etsy and the joke was all I ever wanted was a $500 day. All I ever wanted was a $1,000 day. All I ever wanted was a $10,000 day. All I ever wanted was $100,000 day. And they just started building up and adding up. We created up this leather-making company and you had to learn everything. We had to learn how to design, how to make, how to teach people how to stitch, have the quality, what the leather was. And pretty soon we just couldn't get enough leather. And when the pandemic started, which was big because we've grown real fast, real big, real fast, a gentleman named MacCoy Merkley, who have you've met, who is a marketing genius and one of my best employees said, "Books will be written about people who get scared and people who take the reins and take chances.” And I put on three masks, flew to Mexico, and was able to set up a little place that we called The Studio with the top artisans in Mexico. Because everyone had been laid off because of the pandemic but they wanted to work and everyone was scared. And within two years, we became the largest leather bag-making company in Mexico.

Adam Robinson: Unbelievable.

Curtis Matsko: And we just got the best people at the right time. People wanted our product. I think one of the keys to our success, I'm going to tell you this, I started this as a broke artist. You know, I was doing a lot of yoga, walking around, drinking green juice, reading books, sitting on the porch. And so, I didn't have a bunch of money to spend on stuff. I just didn't. And so, as we became more successful, everyone said, "You got to raise your price,” and I'm like, “No, I would never spend that much. I don't want to buy an $800 leather bag. I'm not going to buy a $1,000 bag. I think 100, 150, maybe 200 that’s the top. That's as high as I'm going.” And we stuck with that. And I think that that's one of the things that made us go viral because we get more people who buy from us because their friend told than off of Google or Google Shopping or Google Ads. It's the viralness of people loving the product. That's what's made us take off.

Adam Robinson: So, we're kind of the same way right now. And although you haven't started telling people yet, have you? Or have you about us?

Curtis Matsko: No, I have not. No, I have not. I will explain that, too, but I will today.

Adam Robinson: Yeah. So, I have this theory the way the world is all interconnected with the social media and stuff, it's like unless your product has that viral characteristic already, you're not going to be able to compete for ads with people who have it if that makes sense. Like, if you have the virality, you can use this machine to speed it up. If you don't have the virality yet, you are just going to waste a huge amount of money banging your head against the wall. That's my theory.

Curtis Matsko: You can in the short term. You can try and throw some money at the algorithm. You can try to figure it out. But the problem is it's easy for anybody to get 100,000 people to their site every month, right? It's 3,000 people a day. Because you're only searching for a very small amount of people. But as you spread out, everything gets more expensive. All the ad buys get more expensive, your employees get more expensive, the distribution gets more expensive, everything is more costly. The only way to even that out is to have the people that you've already sold go out and tell other people and continue to buy. That's your one advantage because building a big logistical-making company, it's expensive to do and it's more expensive with online advertising in order to do that. Your only advantages are those people and I've said this and you've heard me say this, we started as a maker company, and the first year I thought I was amazing. I'd go down and I'd be in the garage and I'd make a journal and I'd say, “Look, I'm a genius.”

But our people are so much more interesting than I am. We read the stories of the hundreds of thousands of people every day, and it blows my mind. There's the story about the woman that I love so much that lost her job. They let her go and she went home that day and said, “I'm going to buy a nice leather bag,” and her sister said, “Why are you buying a nice leather bag?” And she said, “When I get a new job, I'm going to proudly wear this bag. This is my mindset of what I'm going to do.” A week later, she got her dream job, twice as much money, went to her job, bought a bag for her sister, and gave it to her as a present and said, “This bag is magical. It's going to change your life.” So, those are the folks who become the heroes and they tell everybody. And we are shocked. We are literally shocked at the hundreds of thousands of people that are just obsessive about our products because people forgot what leather smells like, right? They buy our bags and they put their face in that thing and said, "This is that smell, that real leather smell,” which they love so much.

Adam Robinson: So, I want to ask you about two things. I've heard you talk about product and community so far.

Curtis Matsko: Yes.

Adam Robinson: In Europe, I've heard you talk about marketing a lot. So, what am I trying to say? Are those like your three biggest business pillars? So, it sounds like I'm going to just put this up and take it section by section. Number one, do you have any like, how do you make a product that’s unbelievable when you don't know anything about it? You said it like you now have a bag that people are obsessed over. What? Like, I can do that? You know what I mean?

Curtis Matsko: I've got the answer to that. Now, number one, I am a marketing guy. We had a moment one time. We're out to eat with my girlfriend at a Mexican restaurant. This gentleman came up. He was talking to me and my girlfriend, and he’s showing me his leather wallet. And after he talked about it for like 5 minutes, then he walked off and I said, “Why is he talking to me about his wallet?” And my girlfriend said, “You own a leather goods company, dummy.” And I'm like, “Oh, I thought I owned a marketing company. I forgot.” Well, that's number one is we're marketing. Number two is I am the youngest of four boys. Now, if you are the youngest of four boys, you know that you're always seeking attention. You're always seeking approval. I literally am shocked when someone doesn't buy a product. I am someone of those people that I literally focus on every single detail. And when we started, we actually went out, we do a couple of art festivals to see what people thought and people would walk in. It's not like I was surprised when someone bought. If someone came in, I said, “How do I get every single person where the quality is so good, what it does is so good?”

So, I obsess about the products. So, when you have the market and you have the product and they're both clicking, that other side really takes care of itself. If you go to some of these big marketing seminars, you talk to an expert, they'll keep saying people first, people first, people first. You can hear everyone kind of go, “Yeah, yeah, I understand that but it's not real,” it's real that you need to give them the value and what they want. It has to be there. It's got to be so good that they have to tell somebody else about it. Now, I'm going to tell you a little bit of it. We really lucked into it because I wanted this product until I made it. Those first couple, we set a formula, and once that formula was set, every time we spent so much time on the product and the price to make sure that people, when they get it, they're just going to want to explode on that. But we're a marketing company, but you have to do everything.

Adam Robinson: So, what does it mean, we're a marketing company?

Curtis Matsko: What it really means? That's a good question. You know MacCoy.

Adam Robinson: I mean, I know the guy. Yeah, MacCoy. I get it but I guess what I'm trying to say is, could you stick a - and I heard a rumor that you might be doing this. Could you stick a watch into that machine and have it work the same way?

Curtis Matsko: Could we design watches and put it into our marketing machine and our customer service and our ability? Yes. It's very possible that someone like me could design watches. It's very possible that we could do clothing. It's very possible we could do anything. We could put that into anything. And I think that what it is, we have a lot of people in our company, Adam, and there are three brains that really are the marketing side. And what it ends up being is marketing is not doing what you think everyone else is doing. It's doing something different than everyone else is doing. And you have to be fighting that every day. So, every night I'm sitting in my house, I get a call from MacCoy and we literally talked for 2 hours and we just talk out these big ideas to give ourselves the energy that when we go in, our employees are going to start deconstructing, “Is that really a good idea? Is that really a smart idea?” You literally have to be so strong in your opinions on the marketing side that you can't let the day-to-day people take you away from that. We need to do something that doesn't appear like it's working, but we know in our heart it is and then all of a sudden, three months later, it takes off and everyone else was ready to jump ship.

So, when you have a company, you're going to have naysayers in your own company. You're going to have wonderful people, smart, brilliant people that do what their job saying, “I don't think that's a good idea.” And you have to, as the CEO and as the Head of Marketing like I am, and as MacCoy is say, "We have confidence, we are unflinchingly optimistic, and we are unjustifiably confident and we literally just say it's going to work.” And guess what? So far it has. I had a friend call me up and said, "You know, if this company didn't work, could you do this again?” and I said, “This is my third company. Of course, I could do this again.”

Adam Robinson: Do other companies resemble it? Like, were they both marketing companies?

Curtis Matsko: Yeah, they were marketing, but they didn't have a physical product. This is the exciting thing because they were more of like, what you always go on the YouTube and see some reels and say, “Oh, you can sell something and there's no product and it’s delivered. It's a software company,” which is amazing, but this is a physical product that we have to find the materials and logistics and make it, the quality control and put it on, ship it and ship it to the people and do returns. And it's vast but it's incredible. When you see the numbers, it's become pretty awesome. But MacCoy said something recently. Somebody said, “Can you tell me your sales projections for this year?” And he said, “Go to the production people.” They’re like, “Well, no, we don't want to know the sales projection.” He says, “Go to production, whatever they produce, I'll sell.” Which is true. We're out of almost everything, right? Like as fast as we can make it, we can sell that. And that's a really fun situation. I know it seems overly confident but we've done it again and again, week after week, month after month, year after year. We've doubled, we tripled every single year.

And the things we have coming up this next year are beyond exciting. And for everybody who's made it this far in this podcast, your company and’s software is literally mind-blowing in what we've done. So, I'm going to interview you for a second. No. Nope. I see you pausing to tell me something. I want to tell you a story. I heard you speak in Austin. You talked for one minute and everyone else was talking. No one was paying attention. I heard what you said and I literally raised my hand and said, “Are you profanity, F-ing kidding me? Is that really what your software does?” And you said, “Yes.” And I turned and walked to the back of the room and my marketing expert, MacCoy was back there and he said, "Don't worry, I'm already doing the math on this thing.” And we literally went back to Portland and we just call it, in our company we call it The Austin Software.

Adam Robinson: The Austin Software.

Curtis Matsko: The Austin Software. We met you in Austin, you live in Austin, Retention’s in Austin, and we said, "We're not even going to tell you guys what this does. It is absolutely exploding our company. It is exploding our company. It is unbelievable.” In five, six years, we gained 700,000 emails. We've gained 1.1, 1.2 in the last 3 to 4 months, and the return on that is unbelievable. It's for every dollar we spend, I think we bring $29, $33 back. We're just like, “Give me more product because we can market it to anybody at this point.” It’s that good.

Adam Robinson: Did you have any hesitation whatsoever? You don't seem like a hesitant guy.

Curtis Matsko: I think I told you that day I don't live in fear.

Adam Robinson: Yeah.

Curtis Matsko: No, I had no hesitation. I literally had no hesitation. I knew we could figure it out. There's amazing, great companies that are doing it that are figuring it out. There's always challenges. There's always hurdles. Now, there really wasn't with this. With working with you, Adam, and with your people, I just gave it to Matt and you've met Matt many times and he contacted people, made a few things, got it, set it up, and I said, “Hey, show me what we're doing.” And every week he sends me a little update and I just smile and say, “We need another $10 million worth of product right now.” And literally, I really do that. I'm just like, “Oh my gosh. Do you understand what we have right now and how we can do this?” It literally makes us excited. I call MacCoy up sometimes and I'm like, "This Austin software like we've got to do it now. We've got to go. We've got to start a new company. We've got to do that. We can use this software to do anything.” And anyone who's not doing it, I mean, you know it, go to Retention, just they’re just being silly. They're just living in fear and you don't get to get $150 million, $200 million a year company by living in fear. It doesn't happen.

Adam Robinson: I agree.

Curtis Matsko: I think that one of the things that and my COO, Anna Gaines, you've never met Anna, but she is just brilliant. She's wonderful. She's kind and she's smart. I used to say, “I don't care about money. I love the game of figuring this pattern out and what it is. It's the game.” She said, “You can't say that. You can't say money is not important to your employees.” Then I'm like, "But it's not.” If I was always freaked out about money, I wouldn't be able to make the steps that I do to grow the company. You would always be frustrated. You'd always be overthinking these things. You go by a gut feeling, or at least I do, on when it works. I think I told my people sometimes I can view a few numbers in marketing, just a few. And it's like The Matrix. You know how when you see that they look at the computers, it's just those things dripping down and they look at that and like, “Look, Jimi's running up the stairs.” I can see one or two numbers and say, “No, you don't get it. This product, not this one, will excel. This is the right price. We need to go all in on that.” And guess what? My numbers usually work out because I've gotten this down good enough with just instincts and patterns and lack of fear in order to grow it, which is fun.

Adam Robinson: So, like, your mindset is very unique. I think you realize that.

Curtis Matsko: I'm told that almost every day of my life. Yeah.

Adam Robinson: It seems like a key component to your mindset is you don't live in fear. I've had people tell me that recently too, so I'm like sort of. I hadn't really identified it. I'm actually making a TV show right now. Did I tell you this? It’s called Million Dollar Challenge. So, I'm making a - the first three are coming out March 20th. It's a ten-minute 44-episode docu-series chronicling the path or the failure to a unicorn this year. And I'm defining unicorn as 250% revenue growth with whatever. We clear at least $20 million in free cash flow, 50 million top line. That software business is a unicorn. So, I literally hired this woman and this videographer to like show, run, and direct basically what it's like to be in the middle of this as a guy like you or myself because it's not just that. It's like the world thinks about you differently after this. So, it's like watching it all happen, like chronicling it week by week. And this woman, as I'm sure, well, it's probably more obvious with you but she's just like she's like, "Nothing's blocking you.” She's like, "You don't have any perception of like any type of fear.” I'm like, "Yeah, I don't know. I just see it so clearly.”

Like, I know what's going to happen. Everybody that I work with, I show them the spreadsheet of how it's going to work, you know? And so, they all believe and they just make it happen. So, yeah, I think that your mindset, it's definitely no fear. It's definitely you're geared to get attention, right? It's like you default to just like bringing attention. I like to phrase it as like you create a mosquito light. It attracts negative with mosquitoes, but it just attracts energy that beams out that attracts people with varying degrees of similar energy to you that can sort of radiate it out also. And I definitely like see that in you.

Curtis Matsko: There's no doubt about that. I spent a winter in a Zen monastery with eight Buddhist monks and me and 16 hours a day of noble silence and reading Calvin and Hobbes every morning and trying to make the monks laugh after I could talk. I gained such insight into what's called state awareness. You can try to tell somebody what it's like after you've been meditating 8 hours a day for a winter but they don't understand it until they get into that state. And then things just become clear. You just see it. You can't think your way to it. You have to be your way to it. In being an entrepreneur, in building these companies, as you're feeling right now, you're just seeing all of those barriers that you thought were there just fall away. They just drift away and you're like, “Wait a second, all this is possible.” I have been able to attract literally the best people in the world and I know that because if I could spend time with I could choose 12 people. I would choose ten of those people would be people that I work with every day. Literally, do anything that they do in their life, I would rather be with them to get coffee, them at their friend's wedding, them on vacation, working, going through good times and bad times.

We had a party at my house here in Mexico. By a party I just mean about 14 of us having some dinner and everyone's having just a good time and laughing. And there was one person who didn't work for us and he called me aside and he said, “Do you know how lucky you are to have these amazing people?” And I said, “Luck? I spent the last six years finding them.” I've literally walked around and said, “Wow, that is an amazing person. I want them to be part of my life.” The people who are running my company did not get hired to do the things they are. We didn't say, “I need the COO, I need the person that does this, I need the logistics person.” I hired an amazing person and said, "What do you think you could fit in?” And they worked their way and all of a sudden they magically became a great CFO. They magically became a great COO. They magically became a great creative director. And guess what? Awesome people can do that. Crappy people, it's just they're never going to get there. And it truly is about attracting the right people. And I am the biggest believer in the world that life's awesome.

You probably had this yourself recently. I probably have 20 people this year call me up and say, “Can I come talk to you? Can you teach me how to do this? Can you tell me how to do this?” And most of them know, I'm going to be honest with you, know. Most of them just didn't like their job and they said, “I don't like my boss, so I think I need to start my own company.” I'm like, "Come on, that's not what we're talking about.” I'm talking about life is much more simple than they make it. It really is. You're seeing now, as I talk to you, what I saw you last time in Austin, you said things that you didn't say at the time before and you're like, “I'm seeing it now.” I just see it. All these things fell away and it's so much more simple than I thought. I got the right people in my life. I made a few simple decisions. I did the right things each day and each week, and all of a sudden, you're just growing exponentially and everyone else thinks it's frickin magic.

Adam Robinson: I mean, it's just this and another thing that I think which has probably been in your mindset longer than mine, the shift of anything's possible, right? It really has happened to me recently, and it's the coolest thing. Question, do you know who Rick Rubin is?

Curtis Matsko: Yeah.

Adam Robinson: So, he just wrote this book called The Creative Way.

Curtis Matsko: The Creative Way. Genius

Adam Robinson: Did you read it?

Curtis Matsko: Yeah.

Adam Robinson: So, I'm wondering if you feel the same way I did about it. I was reading it and I was like, “I've never heard my approach to business captured this clearly in any of the business books I've ever read.” Because he's like, talking about things like harnessing energy and transferring them, basically, it's like dealing in emotion. And I think like once you get a product that's as good as yours is or as good as mine is, like, if you can nail this thing where you're doing what an artist does and you're like harnessing this energy from the universe and you're transmitting it to the people you work with who are then transmitting it to your customers and partners and through the ads and everything else. It's like the better you get at that game and amplifying that energy like that is the mosquito light, in my opinion. Everything becomes electric.

Curtis Matsko: It's so true. If people haven't read the book, they haven’t listened to the audiobook then listen to the audiobook, watch some of the YouTube videos of that interviews with him. And the two things that really jumped out about his energy were, number one, when he basically says, “I don't make things for people. I don't make things so the audience will like it.” I make something that's great and I throw it out there in the world and guess what? People eat it up because people don't know what they want. They only know what they've been given in the past. And if you're going to do something different, you have to go for greatness, not repetition of something else. And he has a certain way of energy and really the thing that I know because I've worked with creatives for 25 years is the ability to say, "That's very average. Don't you think we should take a little more time and really do something a little bit better and not just kick things out in the world that are average?” Let’s just do something that we all feel is more important, just deeper to us. Put it out in the world and guess what? People attract to it. They grab it and that energy is amazing.

I have spent the last ten years of my life attracting some of the best people in what I call magical ways, where I just bump into somebody and they said, “I literally took a left because I thought there was something down here. I walked down. I saw you in those funny glasses. I walked up and we talked for a while,” and they like gave me a hug and said, “We're going to be best friends.” Right? And those people are still in my life. I have that happen to me. It's not that I'm a loud person going out and jumping up and trying to get attention. You've seen me in a big group of people where I'm just sitting there not talking. Right? But people will come up and when I talk to them as people and tell them ideas and help them out, they sure seem to be attracted to it. And when you can get employees to do that and business partners and consultants and just everybody in your life, it just becomes fun and easy. When people always say, “How are you doing?” I say, “I live a pretty good life.” Most people would kind of like to live what I live as being surrounded by amazing people, doing amazing things.

Adam Robinson: Yeah. I love that. I'm reflecting back at Geek Out when you were giving me the quick spiel about how in your opinion there's like three different people that you need in your business life to make sure you're not f*cked. Do you remember that?

Curtis Matsko: Say that one more time. I’m sorry.

Adam Robinson: So, we were at Geek Out in the bar.

Curtis Matsko: Yep.

Adam Robinson: And we just started chatting and you're like, “There's three different people you need in your business life to make sure everything goes smoothly.”

Curtis Matsko: Yep.

Adam Robinson: Who are they? Can you give us that real quick?

Curtis Matsko: Well, if it's what I thought…

Adam Robinson: It’s always sales, legal, the people.

Curtis Matsko: There you go. What you need is someone to bring the people in to buy the product. That's the market. How do you get the attention? How do you get the message out there? You need somebody who literally knows marketing, right? You have to deliver a product, whatever that product is, whether it's a physical product, a software product, whatever that is, you have to have those people ready to deliver that. And then you have to have somebody to keep you out of jail. They've literally got to sign the contracts, pay the leases, pay the bills, do all of the little things that you need to do and… Hold on one sec. I'm at my home. Okay. So, the three people that you need, Adam, are number one, you got to have somebody who can sell your product. They got to go out there in the world. They got to find the people and they've got to display what that marketing is to bring people into your product. Number two, you have to have somebody who can deliver the product. That's really important, the customer service, the deliverability. And then you have to have someone who does the legal and does the payroll and does the human resources and runs that. Those three people have to be superstars.

Literally, if you've got those three, you've got a company. If you got two, you better find someone else to do one of those things because any great company has that person who can get the attention and make the sales, they have somebody who can make sure the product's there, and then that day-to-day disciplined person that you know is going to make sure that the lights are on and that the people are treated well and that everything is done the right way.

Adam Robinson: So, I'm guessing that you don't really identify with that last camp, but the first two you have your nose in. Product and sales, is that right?

Curtis Matsko: Oh, it's another MacCoy thing. No, I haven't paid a bill in years. I don't even know where my checkbook or my credit cards are. It's not because of the bunch of money. It's just because it's not where my brain goes. I don't do that. I have amazing people to do that. I actually used to have a business partner. His name was Scotty. Had a big Internet company, run with him, and it's pretty big. We did some good stuff and people said, "When are you going to start your new company?” I said, "When I find another Scotty,” because he did all the basics, the day-to-day stuff, and I did all the marketing, the dreaming. And I met a young lady named Anna and within one day I said…

Adam Robinson: She was a Scotty.

Curtis Matsko: She's the Scotty. She's the new Scotty. And she is anybody in our company that meets her, she's quiet, she's competent, she sits and listens and everyone says, “Wow. She's the company.” She is everything that holds it all together even though I'm the marketing and I do things that her brain could never do. So, she makes sure all of that, the deliverability of the product and she works to do all of those things. But something that we do is a little bit different. I met you at Geek Out and I was sitting out one time talking to a couple of people and we decided that what's different in my company compared to many of the other people that were there, all of these million or $2 million companies and they're trying to figure out how to make it go big, and what we realized the difference was, was this. These were people who were given a product that said, "Here's a coffee mug. Sell a million of these coffee mugs. Here's a microphone. Sell this microphone.” My brain thinks, "How do I create a product to give to somebody that's going to make $100 million?”

So, because I do the marketing myself, I want to make it easier by having a great product and being the CEO, I'm able to go out and actually develop and choose and find those. I made the first journals in our company. I really did. And after about the first week, I got a couple of people who said, “No, you're not allowed to make them anymore.” I'm like, “What? I'm really good at this.” Like, “No, you're really not. You're great at the idea but we can find people to do that better.” And as you go in your company, you just keep moving up higher and higher and getting great people to do what you used to do. Last year our big saying was what got us here will not get us there.

Adam Robinson: That's the saying, believe it or not. I think that has to be saying if you're growing as fast.

Curtis Matsko: It has to because you're always so far ahead of that curve.

Adam Robinson: It's just awareness, you know? That's amazing. So, how do you split your time? Like, Portland versus Mexico. Let's talk about that. Are you near your factories right now? Is this just kind of like a vacation place? Yeah. So, answer that first.

Curtis Matsko: So, what they don't know on this podcast is I'm looking at you. You're sitting there in Austin in your nice shirt there, and I'm sitting here with tropical greenery behind me. I live in a place called León, Mexico. And when Americans think of Mexico, they think of Cancun and Tulum and Cabo and Vallarta, right? Because the Americans go to the beaches. I'm inland. I'm in a place called León, Mexico, and it's the fifth largest city in Mexico. Mexico's the 14th largest economy in the world. It's a city of 2 million people. It's an industrial city and I absolutely love it. My factories are here. My friends are here. The people that I meet with and I have day-to-day are the nicest, most kind, most amazing, smart people in the world. So, I bought a house down here just to be near to the factories that make our product because it's so important that we do that right. And I literally divide my time back. I buy a one-way ticket, and then when I'm needed back in Portland, I run to the airport and fly back to Portland. And then when I'm needed down here, I come back down here.

But I was flying down here and I was sitting next to a Nike executive who was flying into Mexico City and he said Mexico to him feels like what we think of America in the 50s, right? Little bit slower. People are nicer to each other. Families are a little more important. Now, I'm a good Portland liberal, okay, but I still love that people respect and care for other people. I love the fact that these people down here, you not only meet them, you meet their family. You meet their parents, you know all of this. And I love it down here. I love the people. So, I go back and forth. When they need me for marketing, I fly back and I have those meetings. When I'm needed down here, I'm down here.

Adam Robinson: How frequently do you fly back and forth?

Curtis Matsko: Ten, twelve times a year.

Adam Robinson: Okay. That's nice.

Curtis Matsko: Yeah, it's really nice. Not right now. It's snowing in Portland. They told me yesterday that it's snowing in Portland.

Adam Robinson: Is it unsafe in any way? Are people like you getting killed or kidnaped or whatever?

Curtis Matsko: I'm not. I remember this when I was studying in college. I was studying political science and they said, “Do you want to know why you always hear about murders in the Middle East? It's because that's where all the journalists are. They’re all stationed in the Middle East. And when something happens, they tell you about it. It's not in a small town in Illinois or a small town in Florida or a place in Czechoslovakia where the same things happen.” So, you might be talking that there were, it was cited in the paper the last couple of days that there was four people that were abducted near the border. We're not near the border. We're 5 hours from Mexico City. We're in safe neighborhoods. I walk around. I have amazing friends. I love Mexico. I love the people here. And I love Portland. I mean, I love the United States but you really get to live the best of both worlds when you're here. And you're going to come down and visit me one of these times, right?

Adam Robinson: I think we're going to come down for all of August. I'm not asking to stay at your house for an entire month, but we would love to hang with you for some of that time.

Curtis Matsko: So, for your audience who just knows your voice and the picture of you with your great graphics for Ten Years In The Making, I was able to meet your wife and she's fantastic.

Adam Robinson: Oh, she’s so wonderful.

Curtis Matsko: Oh, man. She is awesome. And so, I asked you to come down and hang out down in Mexico, which was not true. I was really asking your wife to bring you along as she comes down to visit that's down here in Mexico.

Adam Robinson: Bring her a little dog, too.

Curtis Matsko: We have two little dogs that are right over there right now. Absolutely. They were given to us six years ago by someone who was having some things going on with their life and they’re everything in the world to me right now. I love that.

Adam Robinson: She's a little chewiny. Chihuahuas are nice.

Curtis Matsko: So, tell me about this Ten Years In The Making. Tell me about the podcast, how it's going.

Adam Robinson: Okay. So, I mean, I think it's going pretty well. One thing that I think that I've been critiqued on and I was trying to lean into some of this during this interview was people are more tactical than they should be but that's just the nature of people. Like, if you watch YouTube or whatever, there's always these prescriptions. And actually, the Rick Rubin book, he talks about this stuff. Like, the formulas don't work but inspiration from someone else's journey can be incredibly valuable. Beautiful. It's a beautiful thing but I'm still trying to like, and I didn't do a great job at it but I'm trying to like, like with your mindset, I think it's very unique. I tried to sort of reiterate things that I think are unique about it, that you have no fear, you think anything's possible, that you have this sort of energy that is like attracts people or whatever. So, anyway, I'm trying to get better at podcasting. The reason that I'm podcasting is because we hadn't actually had this conversation of why am I doing this founder brand crap.

So, I view what I'm doing right now is a land grab. There is nobody selling into this ecosystem, anything like what we're doing. Little guys are popping up right now. I need to build out an agency partnership thing and get to a critical mass where basically above 60% of a market like your dollar goes three times farther than everyone else's. That's sort of the rule of thumb. So, Klaviyo is way above that. I think we can get there. We have a head start. When you look at the world and it's like, well, how are people communicating these days? How are ads being served? Whatever. It's all social media and people are on social media to connect with people and not companies, for the most part, unless the company profile is run like a personal page. I mean, I think your community effort is a close substitute. You know, maybe it will do something. Founder brand will do something a little bit different, but your people want to hear your story, man. It's just like you don't think they do, but they do, and interviewing these really interesting people. Like, I'm not doing the distribution right, I know that, but I'm getting there. I'm coming up, getting better at it.

But like having a podcast and if people listen to you every week interview interesting people and they hear you're articulate and intelligent and talking about interesting stuff, like they feel like they get to know you and then they'll buy anything from you. So, that's sort of the idea. It's like the 1,000 true fans idea but kind of like magnified is the reason that I'm doing all this stuff and it's benefiting me in these ways. It's like people are lining up like I've had the CMO at one of these big Shopify apps literally just text me and say, “I want to work for you.” The very senior partnerships people, “I'm done with this place. I want to work for you.” It's all happening at the same time but building this authority for myself in this way it plays off the brands increasing in brand heat as well.

Curtis Matsko: You know, when I advise a lot of people who are ready to make a decision, they always want to make sure there's something on the other side like, "If I start this company or if I do this expansion or if I try this, are you sure it's going to work out?” because they're in fear. You never know what is out there until you go through the door and you walk down the street a little bit, right? You don't know what's around the corner. You have to walk down to the end and you actually have to walk around the corner. And they want a formula. They want assurance. And what you're doing is saying, "Hey, I deal with people every day, amazing people that are saying amazing things.” Right now, you have the feeling that I have where things have slowed down like they say in football when the quarterback says, "The game has slowed down. It's making sense,” and you're like, "Okay. I've got this right now,” and you're ready to step out there. And if you're anything like me, I was talking to a public relations company and they're like, “Are you doing anything interesting we could talk to your people about?” And I'm like, “If you lived in my life for one day, like eight things this morning like, I had eight conversations this morning that people would love to have had insight into what those are.”

So, actually, yesterday I hired a crew of people who are actually going to be doing photographers and video, and they're just going to come around as I am doing meetings as I’m meeting with people, as we're out to dinner, as we're flying around the country and around the world and just picking up some of those things that we do because as I mentioned, it's not for me. I know it. I've done this and I've got where it's at. But it does two things. Number one, it reinforces what I'm doing in my own mind when I teach it to somebody else and they learn it. And there is nothing like when you say one thing, you don't even know what you said. If I talk to somebody for 60 minutes, they'll come back to me a couple of months later to say, "What you said really meant a lot.” I don't know. What did I say?

Adam Robinson: Right. Exactly.

Curtis Matsko: And they'll have one line. They say, "You said this. That led me to do this and that led me to do this.” I'm like, “Oh, I didn't know that was the line. I just told them how I feel and how I see things that day.” And magically, if they're in the right place in their life, they'll take the steps and it will actually slow the game down, things will get easier, they'll be more successful, hurdles will fall away, and all of a sudden they'll be in a new area of their life that they literally could not have imagined to. They tried to build up these formulas of how to get there and formulas do not work. Formulas do not work. You've done this before where we've been to the Geek Outs or we've been to a Triple Whale event or we've been to something and people come up and say, “Could you tell me the secret of marketing?” No. It's a mixture. It's the feel. It's the experience. It's the judgments. It's how do you make that decision and where you at when you say yes to this and no to this.

Adam Robinson: That’s amazing. So, this is opening doors for me that I didn't even know existed which is making me want to go harder. And I think one of the things this guy, Jon Cronstedt, who I interviewed, articulated it really well. So, his view is that community and culture are the only two moats that exist in the world. Somebody could rip your bags off in some fashion, like just the materials of them. Nobody's going to get the energy of working inside of Portland Leather Goods. So, I think something that, well, this is what he said. He's like, he got me started on this, actually. This is why I had him on the podcast. I didn't start it for six or nine months after I heard him say it but he scaled Kajabi from 6 million to 100 million and they did like secondary in $2 billion evaluation. He was the CEO. And he got asked on stage, they said, "If somebody were about to do what you did, what would you do?” He's like, "There's no question. I would start writing on LinkedIn about what it's like to work at your company.” So, when he's on my podcast, I ask him about that.

He's like, “Look, here's what I think. If you're to watch Yellowstone for those three seasons, you have a very good idea of what it's like to be a cowboy on Dutton Ranch, right? You just f*cking know. It's not because James Dutton or whatever wrote his mission vision values on the wall and was sort of like holding you to your OKRs. You know what it's like to work there.” He's like, "This stuff, this content creation that you're doing, and how your values come through in what you say to people on your podcast, for instance, and how you report what you're doing and how you're growing your business, people opt into that. And when they opt into that, they're much more engaged. They feel much more purpose and they just want to make more of themselves.” So, I think that you will, depending on how broadly you go out with it like you're going to amplify this energy that you're putting out in your own company and people are going to show up at your door and be like, “I have to be part of this.” That's what I think you can come with it. I mean, I'm sure the reason you didn't want to do it is the same reason I don't want to do it.

I don't want to be f*cking famous. It’s the last thing I want to be. Like, I would love to be sitting down there in Mexico right now, just whatever. But like, the reality of it is what's going to make Portland Leather Goods a billion-dollar company is getting even better people to show up and scale the thing. And I think the fast track to that is you showing this magic that you've created.

Curtis Matsko: You are 1,000% correct but it's that mix of when I talk to other people and you have to teach your own employees how to view things differently, right? Not to be like every other company that is stagnant where it’s not going to work or is going to go out of business. They think that's how a business should run because they don't know. And you have to teach your people every day. And I find out the more I explain how things are naturally can be done better, more optimistically, more quickly, I see it myself even better, and it makes it easier for me to explain it the next time and the next time. And now more people have that vision, so you grow even faster and even more. I love the talking about it and teaching people, and I know that sounds a little bit didactic like that I'm teaching people, but I truly have done things that you have to go through to learn what it is. So, in a way, they are learning whether I'm teaching them or not, they're learning. It's a little bit selfish and it's amazing. And I have thought myself, “Wouldn't it be nice if Thomas Edison had a film crew around him 24 hours a day when he really thought of some of those damn inventions and it's not like what we thought it was?”

Like, really all of the great people in history is just like, hey, what if they had an iPhone and had somebody shooting them and saying, “Hey, today I came up with this idea. That one didn't work, but this one did,” or, “This is how I feel today and this is what it was.” We don't have that. It's only come about in the last ten years that people are saying, “Hey, here's what I've done,” and most of them is not legit. They're just people talking out the rear, right? Some of them like you, it's legit. You've worked with people, you've seen people, your friends around you are being successful, your company is growing, you're being successful, and you can say one or two things that literally could change somebody's life. I believe that wholeheartedly. And how do I know that? Because I'm a long-term recovering alcoholic and I've done it where I've actually said something that I didn't know what it was and somebody came up to me years later and said, "That changed my life.” And I had no idea what they were talking about, but they literally came up to me and said, “You saved me. That was the speech. When you talked, I listened and made different decisions and now I have a family. And now I have this and it's changed.”

You don't know what it is. So, I feel it sometimes when I think maybe I should get a little bit more of this content out there, just so a few people can see and do that feeling and you get to meet awesome people. The better content you create and the more awesome people you meet, like meeting you and meeting a lot of folks, they're amazing. It's fun hanging around really smart, really successful, really awesome people. Is that true?

Adam Robinson: I mean, it's all I want to do. That's just how I want to live, right?

Curtis Matsko: There's probably so many CEOs or entrepreneurs or people who run companies, whether it's three people or 500 people, and they spend all their time talking down to their employees, saying, "Here's what we need to do,” and preaching on down to their employees. When you have to break out of that mindset and talk to other people who are doing things in other industries so that you can see your own life a little more clearly. I'm a big believer in that. And so, yeah, you're the inspiration. You say, “Hey, Curtis, I'm going to set up the podcast.” I'm like, “Ah, whatever.”

Adam Robinson: It was kind of time to draw to a close, anyway. I don't even know where we were but I'm happy that you're doing that. And I think I would be shocked if it's any different than what I said, which was kind of like, “I don't know what I'm going to get out of this, but I'm going to try it,” and then you start doing it and you're like, “Wow, this is totally worth it.”

Curtis Matsko: Yeah. That's totally the way that I see it. The hardest thing is actually trying to describe to people who are going to be helping me do it why we're doing it. I know that it's an unknown out there that's going to come together but we're like, “Why are we doing this? What's the point? What's the message?” And I'm like, “Well, the message is to do something, be authentic. Say what you know and put your energy out there and see what happens.”

Adam Robinson: I mean, it will resonate very profoundly with some people.

Curtis Matsko: Okay. So, it's worked out with how many podcasts have you done? How many interviews have you done?

Adam Robinson: Yeah. I don't know. Probably like 20 now. They get produced at one per week and I think I got a backlog of like five or something. So, yeah, around 20.

Curtis Matsko: Well, that's fantastic.

Adam Robinson: Yeah. Episode 16 hit yesterday, so yeah, probably 20, a little over 20. By the way, there's this other thing which I'm sure you agree with. It's like if I get energy from it, I will do more of it. If it takes energy from me, I'm never doing it again kind of thing. Like, I actually get a lot of energy from these conversations because you just uncover so much. It's like everybody that I'm interviewing on this, they're unbelievable human beings. You know, they've just done things that no one else could dream of. So, kind of getting inside these people's heads is just so inspiring to me.

Curtis Matsko: My assistant, Marianna, is over here and she's just nodding in her head yes as you're saying some of these things because she literally gets to deal with me on a day-to-day. And at 8:30, the big door opens up and she walks in and say hi and then I say, “What are we doing today?” And it is nonstop interesting great people, a million decisions. Why would you give this up? Why would you not want to do this more and more and more?

Adam Robinson: That's the scary thing about selling, right? Who would we be? I don't even know.

Curtis Matsko: Yeah. Well, I would literally just try to duplicate what I just already said, right?

Adam Robinson: Exactly. Yeah, totally.

Curtis Matsko: So, why would I ever do something like that? When the game is the game, when it's not about money, it's about the community and growing the people and having the links and the connections, it's not only easy that it's fun. And I've got to tell you, the hardest day of my week is Sunday morning when there's no football on and I wake up and say, “Oh sh*t, I have another day before I get to go back to work.”

Adam Robinson: That's a lucky position to be in. I feel the same way.

Curtis Matsko: And then I was like, I tried to talk to my wonderful partner and think, "Okay. I’ll be about business. What else can we talk about?” But it's so exciting to me and she's wonderful that way. This morning I said, “Hey, I've got this great new book. I think I need to write a book.” She's like, “Oh, really? Do you want to tell me about it?” And I talked to her for about 5 minutes and I looked and she was on her phone. I said, “Did you hear a word I said?” And she said, “Nope, but you seem like you want to talk about it.”

Adam Robinson: I love that. I love that. So, to wrap this up, I always ask people if you could put one thing on a billboard, what would it be?

Curtis Matsko: You know, that's an odd thing because, first, the billboards never be more than six words.

Adam Robinson: Right.

Curtis Matsko: And it's something that I - it's just the word, just literally kindness. The word kindness has jumped in when I saw a big billboard and I saw the font and I saw the big word and I saw the colors on it and, you know, as the CEO and as someone who is working hard and building your company, that sometimes you'll see something and other people aren't on the same page, but you know that you need to help them get on the right page. Because of my energy and because of my passion, I have to remember who I am and take a deep breath and help just be really, really kind. We're starting to send out catalogs and they're just blowing the doors off. They’re just blowing the doors off. People just love our product, and they designed a catalog and it was the best thing I've ever seen. And they designed one the next week for a follow-up and it was the worst thing I've ever seen. And how do you say, "This one’s amazing and this one needs to, you need to redo all that work,” in a kind way? And that's one thing is how you work with your employees and everything.

But the other thing is when you go out in the world and you're just authentic and you're kind, it's crazy how things just work out for you. And when you don't do that, then you're carrying your own problems around and spreading them around the world. So, I've met you a number of times and you're authentic and you're kind. And if you think about it, all the best people in your life have those same qualities. They're authentic and they're kind. And that sure makes our life a little bit better.

Adam Robinson: I love that. Curtis, thank you very much.

Curtis Matsko: Okay. Well, thank you. I appreciate it. And I'll see you when you come on down to Mexico this summer.

Adam Robinson: Yeah.


Just over a decade ago, Curtis Matsko told his wife, “Quit your job and I will start up a company selling things on the Internet and we’ll make $100 million.

Today, that proclamation has manifested into reality, with Curtis’s Portland Leather Goods growing from a garage operation to a $120M+ business on pace to make more than 2 million bags in 2023.

In this episode, Curtis tells the story of how he went from a lofty idea to a concrete success story in just over a decade, including tips on people, product and process.

You’ll also hear Curtis share the principles of success he believes transfer to any company, how taking a people-first approach can lead to an obsessive customer base, and the lessons from being a class clown that good marketers can learn from.

Key Takeaways with Curtis Matsko

  • How Curtis grew Portland Leather Goods from zero to making more than 2M bags in a year.
  • How to harness the importance of referrals to go viral.
  • Using customer stories to demonstrate the value of your product.
  • What does it mean to be a "marketing company?"
  • The emotion entrepreneurs need to avoid to hit 9 figures a year.
  • Attracting the right employees based on human qualities — not resumes.
  • Using Rick Rubin's philosophy to avoid mediocrity and create greatness.
  • The three people you need to make sure your business runs smoothly.
  • What is the value of building a founder brand in public?
  • Why taking formulas from an existing business doesn't work — and what to do instead.
  • Why founders need to have conversations with peers in different industries.
  • How authenticity and kindness can indirectly solve problems.

Curtis Matsko | Portland Leather Goods: From Garage to $100M Company

Curtis Matsko Inspiring Quotes

  • Marketing is not doing what you think everyone else is doing. It's doing something different than everyone else is doing.” – Curtis Matsko
  • If I was always freaked out about money, I wouldn't be able to make the steps that I do to grow the company.” – Curtis Matsko
  • Any great company has that person who can get the attention and make the sales, they have somebody who can make sure the product's there, and then that day-to-day disciplined person that you know is going to make sure that the lights are on and that the people are treated well and that everything is done the right way.” – Curtis Matsko
  • When you go out in the world and you're just authentic and you're kind, it's crazy how things just work out for you. And when you don't do that, then you're carrying your own problems around and spreading them around the world.” – Curtis Matsko
  • “Class clowns are the perfect entrepreneurs.” – Curtis Matsko
  • “You don't get to get a $150 million, $200 million a year company by living in fear. It doesn't happen.” – Curtis Matsko
  • “If you're going to do something different, you have to go for greatness — not repetition of something else.” – Curtis Matsko
  • “Formulas don't work but inspiration from someone else's journey can be incredibly valuable.” – Curtis Matsko


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