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TMBA588: Getting Comfortable With Failure

When it comes to entrepreneurship, failure is often more educational than winning first time.

Many of the greatest business stories start with failure because it’s the learning process that often ultimately leads to success.

Today’s guest describes himself as “an expert at failure”.

Sean Markey started his career as a special education teacher and spent the better part of a decade bouncing between jobs and going into debt, all the while trying to find a way to earn a living online and to buy himself the freedom he craved.

Despite several high-profile failures, Sean managed to hone his skills at SEO and started creating and building successful websites that earn affiliate income.

He recently sold one of those for what he described as “life-changing money”.

Sean joins us this week to discuss some of his greatest failures, how he was able to parlay them into skills that ultimately led to success, and why trying things out and often messing them up is such an important part of the entrepreneurial journey.

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Do you have ideas for things you’d like Dan and Ian to discuss on future episodes?

Our producer Jane would love to hear from you at [email protected] or leave us a voice message using the record button below.

Dan: Happy Thursday morning, I am a bit late on this one, I was just finishing an email to all of the companies on Dynamite Jobs platform, letting them know about a new service offering we’re trying out this week over there. If you want to see the emails, we sort of distilled all our different product offerings, there’s a lot going on, you can just head over to Dynamite Jobs dot com, click register, and toss your company up on the system, and then you’ll get the email. And if you sell services, there’s some benefits potentially as well because we’re starting to promote the services of listeners on that platform.

So a lot is going on. What I want to talk about today is understanding. I had this conversation I was like, I don’t think it’s necessarily true, but it was interesting to me. So here’s basically how it went down. I had had this reason or rationale as to why I, you know, made a pretty sizable investment in Bitcoin a few years ago. And I was pretty public about it on the pod and like, in my social circles and stuff, and encouraging people like – if you come to go to a party, you want other people to join the party. And so, I find myself in these conversations a lot. And I felt like I made my case, again, to a friend. And what he said to me was, ‘Well, you know, the thing is, I just don’t really feel like I understand Bitcoin’. And, when we were talking on the phone, I said, ‘Totally reasonable’. And when we got off the phone, and I was kind of walking around, I thought to myself, ‘Wait a second here, what do you mean, understand?’ I don’t know what he meant – he could have meant that the underlying technology, being a part of the community, ‘I don’t feel comfortable/understand’ could be a fill in for so many things. And that’s what I want to focus on on today’s episode is – this need to understand things is a very strong driver in us. This is important when it comes to entrepreneurship. Because not only is the drive to understand, you know, before we take action so strong in us, but you can choose your battles with understanding. You’re not willing to hold Bitcoin because you don’t understand the tech? Like, do you understand how the stock market works? If you run your business on software, do you understand how that software works? Well, what do you understand about it? Well, that it is useful? Well, in the case of investment, if you demand to understand every company you invest in, maybe you’ll miss the thing that would be more profitable to understand, which is simply this: will somebody pay me more for it in the future? There are so many things about our companies that we’ve owned for years that we don’t understand, yet we own them, and sometimes they go up and to the right quite dramatically.

That’s a very, very long way of saying that when so many of us get involved in entrepreneurship we can’t predict, we can’t even visualise the thing that is going to get us the success that we want, the business, the product, the strategy. But we understand the process of entrepreneurship, which is tinkering, you have to tinker, you have to own, and you have to ship while protecting your downside, you know, keeping your personal expenses low. Again, this is a process that we understand by listening to stories like you’re going to hear today. We don’t need to understand the critical thing that so many people would point to, which is like, ‘Well, how are you going to make the money?’ Just a little parable about the power of essentially choosing your battles and how important that is because the reality is so much of what we do in our economic lives, we simply do not understand.

With that I want to introduce today’s story. Something that appealed to me so much. Today’s guest email to me said. ‘I put in my 10,000 hours at failing and became an expert’. This email came from someone I have known for a long time, Sean Markey has been a member of our computer community, the Dynamite Circle, since the very, very early days. And I’ve been able to see bits and pieces of the journey he’s been on. But until this interview, I hadn’t fully realised everything he’s done and achieved, and how he finally arrived at the freedom he craved.

Sean: Just seeing that money hit my account was insane. I grew up pretty poor. I had $55,000 worth of student loan debt that I just assumed I would have when I was 70, plus all the credit card debt, it was crazy to see that much money hit my account, It was a huge thing.

Dan: So in Sean’s case that that freedom involves being able to live in a small town just outside of Moab in Utah, a place he loves, with his wife, and his small menagerie of animals, some of which will make guest appearances maybe on the pod today. I just want to point out because we often talk about entrepreneurship as this opportunity to freewill around the globe, especially on this show, but I know for a huge percentage of the listeners of this show the more important element of location independence is that freedom to earn a quality living and wealth in a place that’s your place.

So we’re gonna get into all that, how Sean managed to do this, basically, by combining a bunch of different skill sets he’s built over the years – building authority sites, SEO and, in part, acquiring used domains. But we also get into why choosing the type of business that’s right for you has been so key for Sean, and why he thinks he failed badly at that for a long time. We’ll touch on the crucial importance of the people you choose to be around, why entrepreneurship is inevitably messy, scrappy, and difficult to understand and so much more. And, as you’ll hear, Sean is super humble about all this stuff. Absolutely enjoyed this conversation. So let’s jump right in.

I started out by asking Sean to outline his business as of today, and stand by for some standby for some insights about how it’s been affected by the latest dreaded Google algorithm update.

Sean: So in the past couple years, since 2019, I have built and sold about $750,000 worth of affiliate websites. And that’s not including, you know, the money made while running them, like the ongoing affiliate income.

Dan: Do you have a team?

Sean: I have currently a writer that I work with full time, and someone that occasionally helps me with stuff like posting content to WordPress. I used to have a much bigger team but Google’s December 2020 update just murdered all of my site’s traffic, organic traffic, which was, you know, 90% of how people found the site. And I had to let a lot of the team go,

Dan: Can you tell us about that day?

Sean: It was great. I woke up. And the first thing I do, laying in bed before the update, check clicky analytics, and see how things are looking in the morning, which is like the opposite of what everyone tells you – you should wake up nice and then breakfast and workout. But no, that’s, that’s not what you do when you’re running. Or when I’m running like six affiliate sites that all depend on getting traffic, it’s like, ‘Alright, what kind of day am I gonna have?’ And that day traffic was down like 40 or 50%. I was like, ‘Damn, okay, this is gonna be bad’. So at first it was okay. Like, you know, I was down like 40 50% core algorithm update, okay, that happens like, like, that’s kind of what you’re signing up for, if you are investing heavily in SEO, and getting most of your traffic from organic. We’ll, you know, build back, it’s happened before it’ll happen again, it’s not that big of a deal. But then, a few days later, traffic was down another 50%. And then like a day or two later, it was down – I think, in total, it got knocked 90%, the big moneymaker site lost 90% of the traffic in the space of a week.

Dann: My understanding, like having lived through these kinds of cycles a few times is that there are Google algorithm updates that will target a tactic that you’re using and say, ‘Okay, we’re gonna, you know, knock you a little bit’. And then there’s, like, algorithm updates that, like, basically cancel your website. Like, we don’t want this kind of website, it sounds like the latter as what affected your business?

Sean: Yeah. My own research and experience shows that the thing this update targeted was specifically affiliate content, it’s almost like, Google’s algorithm was saying, if you’re gonna, you know, personify it, ‘Hey, just inserting yourself between the user and their purchase is not a huge value add’. Sites that were leaning too much on the ‘best x’ kind of content, you know, like, ‘best supplement’ or ‘best x for y’ kind of keyword construction are the ones that, from what I seen, lost 80% 90% of organic traffic?

Dan: How do you respond to that emotionally when, basically, your business just melts away in one day?

Sean: For me, it’s like, okay, losing 40 or 50% of your traffic in a day or two, it’s like, you know, curse words, and I’m just going to take the day off and mope. But then we’ll get back to it and, you know, figure it out and, and keep going forward. But when it’s when it’s getting like, 75% 85%, 95% I guess I found it funny. It’s just like, wow, Google hates my site, and the site is done. What am I you know, what am I going to do now? Because it’s not running this site anymore. Because it’s dead.

Dan: If you start googling around for, ‘How to make money online’ and stuff, the authority site, the affiliate business model is one that pops up quite often. And, you know, people start to say, ‘Oh, you know, could I start a website called, you know, best, you know, electric racing bicycles dot com’ and like start writing reviews of all these electric racing bicycles, and they’re really cool products and then you know, linking out and stuff. What’s enabled you to make that work where for so many, they can’t seem to get something like that off the ground.

Sean: Sometimes it’s just luck, which is not a helpful answer. But sometimes Google, Google’s algorithm really likes a website. And sometimes it doesn’t. And I think that’s something a lot of people have talked about. Some of these SEO, people will start five different websites on the same topic, and two of them a really take off and start getting a bunch of traffic, and three of them will never get going, and maybe you can make those work with a lot of work. I don’t know, that’s a kind of a terrible answer. It’s only partially the answer ..

Dan: It’s weird because you’re an SEO expert, yet you’re telling me it’s a mystery.

Sean: Yeah, Google, I’m sure, doesn’t want anyone really figuring out a game their algorithm, like, it’s just like this, you know, this super long battle, like they make an update, you have to test things and see what actually moves the needle. Sometimes they’ll take down some really big popular blog network or PBN, private blog network, or something. And, and it’s just to kind of put some fear into people, in my opinion, and others agree, and it’s a little bit, it’s kind of tinfoil hat thing, but once they, they kind of put it out there, like, oh, like your, your site can get, like, wiped out of the index, if you do X, word spreads, and a lot of people stop doing x. But anyways, that’s only partially the answer. The other part of that answer is – I got really good at a couple things within SEO. You can be really good at building links, and just constantly churning out links, and that can drive your site’s towards success, or you can get really, really good at something else like writing really in depth optimised content, which is where I kind of excel. This is getting really into the weeds, but finding domains that are expiring and building a site on a domain that already has links and age, because it used to be a site, it used to be a business, for whatever reason, someone let it die, expire, went to auction, you know, it still has five or 600 links going to it, that’s a really, that’s a really valuable pickup.

Dan: Now we’re gonna get into that last technique Sean talks about a bit later in the episode because helping entrepreneurs identify and purchase expired domains is the focus of his new startup Juice Market dot com, great domain, in which he’s a partner with his former employer Smash Digital’s Travis Jamison, who’s been on the show many times, a TMBA old timer. But one thing I noted when we were having this conversation, as someone familiar with SEO, I did it pretty seriously myself back in the late aughts, around the time this show had just started. And, to me, it seems like it’s pretty much the same game and that was kind of fascinating to me. Whether we’re talking about creating private blog networks – and we’ll link to some episodes about private blog networks, if you’re not familiar with them – creating detailed long form content, building links, all this kind of stuff that Sean mentioned earlier in a lot of ways, very similar to what we were doing 15 years ago.

Sean: I think the game is fairly the same. The main thing that’s changed is these core algorithm updates. These things happen several times a year and they really shake the board up in the SERPs, the search engine result pages. In the past, you know, you had like a Penguin or Panda like this huge, unexpected update, and it wasn’t as common.

Dan: The first thing I’m pulling out of this as a principal is like, back in 2012, when Panda hit us, it was pretty clear, like, what it was optimising for, and we adjusted for that and sort of gradually got back traffic. But nowadays, you’re saying these cuts are more profound, and they’re and they’re harder to understand.

Sean: I think that’s true. The core of SEO is the same, where you write good content, build links, whatever your risk tolerance is, you should definitely know that going in.

Dan: When you mentioned risk tolerance. You mean, there are ways that the aforementioned private blog networks, which are basically a bunch of bullshit websites that link to your site, which are, in theory, more risky to get links from than say running a PR campaign where local newspapers link to you.

Sean: Right, if you don’t know what you’re doing, and you don’t have a high risk tolerance, you shouldn’t do things like that. However, it’ll take you much longer to rank. And, at least, as I’ve seen on some sites, you can still just sort of be collateral damage in an algorithm update, even if you did all the right things. Putting all your eggs in the SEO basket is a strategy that comes with a lot of risk, a lot of reward, but also a lot of risk.

Dan: Has the fact that programmes like Amazon affiliate, you get a lot more reward linking to Amazon than like, you know, stuff back in the early aughts. Has that changed this sort of authority site business model at all? The fact that you know, Amazon’s making it easier for you guys to make more money?

Sean: They make it easy to get into the game, which saturates the market. So now you have a bunch of people going after the same tiny slice of a keyword or a niche.

Dan: Including people like ‘Business Insider’, you find yourself on ‘Business Insider’ reading about the top 10 best K-cup coffee makers or whatever, and you’re like, how am I here?

Sean: Yeah, I think Amazon is long term, a really terrible partner to promote their products because they, in the end, they don’t need you, you need them. They have cut the affiliate percentage that they pay on a bunch of products, I think twice now. And the last time was in April 2020. For instance, I was in the home and garden niche, and I earned 8% on all the products I recommended. And then they changed it almost overnight. They changed it to 3%. And, in some other countries, I’ve heard they’re doing things where like, you only make money on the product you recommend not everything that someone puts into the cart, which was, in the past, a trade off for their terrible, low percentages, you know, you make it up on volume, but like that that’s changing over time.

Dan: Now, there’s obviously SEO for established businesses but I kind of want to talk about SEO as a lifestyle just for a hot minute. I’m thinking about maybe like that 20% of the audience who has a job, and is thinking like, ‘Oh, this is kind of interesting, like I’m a little bit analytical, I know what good content is, you know, I studied English in university’, or whatever. How long might it take someone to earn a living online, say $5, 000 or $6,000 a month in profit, running affiliate sites? How would that process unfold?

Sean: Well I can give my own personal experience. I think I started with the ‘make money online’ SEO stuff in 2011, maybe in 2010/2011. And I wasn’t really able to quit my job and do a full time until 2019. And I did nothing but build sites, and try stuff and fail that the whole time. So I would caution people against thinking it’s easy, and you can just sort of jump in and do it. I spent around eight years just throwing shit at the wall and breaking plates and making a mess. And finally, it paid off. That wouldn’t have happened without a couple of really important things, one of which was my wife has a super stable job, and wasn’t always pleased about supporting me, at times when I didn’t really make a lot of money. But I wouldn’t have been able to take the same path without that, you know. So that’s something people don’t talk about it a lot. But I had a lot of structure and support outside of trying this.

Dan: I’m glad you brought that up, by the way, because it’s a very, very common story in the entrepreneurial community that you have a business partnership in your home. And a lot of men are unwilling to bring up the fact that their wives are part of the partnership. So I really appreciate that. That’s really cool of you to mention that. I mean, it must have felt great to be able to go to her and show her the success that you achieved.

Sean: Yeah, that was a whole thing. I went to college to be a special ed teacher, essentially. And I worked as a teacher for three years from 2010 to 2013.Making more money than my wife was never – I think it’s a stupid thing to be obsessed with personally – but like it was never thing I cared about, you know, like, I didn’t get into teaching for the money, for sure.

Dan: I want to go back to the very beginning. But first off, I want to talk a little bit about your podcast pitch. One of the things you said that you thought it would be interesting for you to come on the show was that you’re socially awkward. I don’t know, that’s not really my impression of you having spent time with you?

Sean: I don’t put myself out there. A lot. You know, I’ll never do video. I’ll never speak on stage at any kind of event.

Dan: Why won’t you talk on stage? It would be so amazing to see a breakdown of your authority site process.

Sean: Social anxiety. On stage I’m awkward, and I mess up my words. And I constantly think about how I look, it’s just a mess.

Dan: Why would you do this then?

Sean: There’s a big editing process, honestly. No one’s looking at me, just weird, obsessive things that I guess a lot of, you know, maybe some people deal with a little bit of that here and there. But I deal with like, a lot of that when I’m doing stuff socially. So being behind the mic, with no camera, a robust editing process. I feel a lot more comfortable.

Dan: I sort of see it as a virtue people who don’t want to share. I guess maybe it’s just like, the trend nowadays is everybody’s sharing everything and wanting to put their face on everything. And it’s kind of cool that you can quietly, you know, make a living on the internet. It’s still a thing I’d rather be anonymous and rich.

Sean: For sure. I spent a large portion of my life writing, writing fiction, writing music, songs. That’s mostly how I’ll interact with the world.

Dan: What was it then that inspired you to want to be a special education teacher?

Sean: I wish I had a nice story, like, ‘Oh, I was blah, blah, blah. And I was super inspired’. But honestly, like, I don’t. But what it came down to is – I was certified to teach Elementary Ed and then I was certified to teach special ed at any age. The reason I got into that is because when I was 20/21, still living at home, and still pretending I was going to make it being in a band and playing music, I was sort of faced with the reality that okay, maybe that’s not actually going to happen. And so I thought, ‘Well, I’ll be a teacher. And I’ll get three months off each year plus holidays and stuff, that way I can pursue my passion projects’. By the way, that is not how that works. No, you’ll be grading, you’ll be planning, you’ll be renewing your license and going to meetings and conferences. Don’t become a teacher for the time off, because you won’t have any.

I ended up getting super lucky, It was a school for teenage boys who had just a lot going on with addiction or traumas. And they needed therapy, they had therapy sessions two or three times a week, maybe. It didn’t come with a lot of requirements to like, work really late, or take on a couple of clubs after school. We started school at like 8.30am or 9am. I got out every day at like 3pm. And every Friday was off. It was super lucky. And so I could spend way more time than the average person with a nine to five working on business stuff afterward.

Dan: You’re paying the rent, you have a job you get out at three every day, extensively. You could, you know, put together some ripping tracks and you know, get some gigs on Friday and Saturday night and continue to work on your band. Why this switch to start to think about business?

Sean: I think at the time my wife was experimenting with a super small business, some kind of yoga thing, setting up her first WordPress site, it seemed like such a complicated thing. And it’s like, why are you doing all this work? And then I tried it myself. And it was kind of fun and, and I guess I saw it initially as a path to getting out of the nine to five, the nine to three. And once I started going down that road, I think it satisfied a similar itch to creating music or to creative writing – you’re building something from nothing. That really kind of hooked me and drew me in. I’m really bad at scaling a business. And putting processes in place. I take really stupid risks, they mostly have paid off or have eventually paid off. All the sites that I’ve sold, all the affiliate sites that I’ve sold, have been the lowest of low hanging fruit is what I went after. And I loved building it from zero to one, seeing those sales go through, building the brand, giving it a voice and an identity, but ‘Okay, we can optimise clicks’, any thing like that, not interested, like, ‘Just take my site, you do it, I don’t want to do that’. I like the act of creating and building something but don’t like the running of things. And once I figured that out, I got a lot more success.

Dan: Do you remember the first dollar that you made online?

Sean: Yes, so back in the day, Neville Medhora, he had a copywriting course. I got like one or two, you know, gigs from that. Then the first consistent money I made was, I set myself up on Fiverr. And this is like, you know, early mid 2011. And I offered to make logos for people, And I did that for a while and I got like a level 2 seller or whatever. It wasn’t great money. And it wasn’t great work. But it was really it was like, ‘Okay, like, there’s something here’. Then I got into building my own sites with my own terrible logos on them. I don’t remember how but stumbled across SEO, as an idea. I guess, like everyone else does, like, ‘Okay, I built this site, but nothing’s happening, what I do now?’ And going to the ‘Warrior Forum’ back in the day and buying really terrible products to kind of see what other people are doing. That’s how I kind of made the switch to SEO, and for whatever reason, that’s kind of what stuck, that’s where I kind of settled in.

Dan: You mentioned that then in 2014, you do like this common next mini step, which is, you know, you petri dish, your own ideas, you need to traffic to a little site. This, to me, is like a very common entrepreneurial journey. Because you’re trying to go from zero to one. And then you kind of look up from your sandbox, and you realise that your zero to one journey is really valuable to like bigger operations that have been asleep at this wheel for whatever reason. And then you basically start a services business saying, ‘Okay, well, my site makes 400 bucks a month, but the reality is if I applied my strategy to like your business, you’re going to be making an extra, like 40,000 bucks a month or whatever’. It sounds like that’s what you did in 2014 or something similar.

Sean: Basically I got fired. Long story, from the teaching job in 2013, I was kind of crushed. I was like, ‘Oh, man, this was a cool job’. It wasn’t a cool job in other ways. That’s why I got fired. And my wife’s like, ‘You don’t have to get another teaching job, you like marketing, go get a marketing job’. I was like, ‘Oh yeah that’s actually a super smart idea.’ But I had just watched, or just paid for a Glen Allsopp from ViperChill course. And going through that course was enough to get me a junior SEO job at a local Salt Lake City marketing agency.

Dan: Wow.

Sean: Yeah, it got me through the interview. And then. what I ended up doing there, it wasn’t a great gig – PBNs were all the rage in 2013.

Dan: So private blog networks.

Sean: Yes, I was the assembly line for building these horrible websites like, this guy, I don’t know how he was finding the domains. Maybe he bought into a service. But like, you know, every week, he would deliver a bunch of domains, and I’d instal WordPress, and I would put a little logo on it. And I would, you know, I would take some content and spin it.

Dan: How do you go from that to then start in your own agency?

Sean: Because I’m stupid. And I thought, ‘Oh, I can sell this’. Back in 2014 getting your own pbn wasn’t as easy as it became. A lot of people didn’t know where to get domains, and how to tell if it was a decent domain, and then how to best link to your sites. So I figured I could offer this service that I, you know, got very good at doing, just because I did it all day, to other people. And I think I put a DC offer up, and I charged $2,500 for a 10-site PBN, sometime in 2014. And two people took me up on it. And I was like, ‘Whoa, I just made $5,000. I’m a genius. I will start my own agency’. That’s not how that works. There’s so much more in running an agency than just being like, ‘Oh, I got a service to offer’. I think I made like $80,000 running my agency and like expenses were at least $80,000 like paying out other people, buying domains. So I guess I learned a lot, but I was not successful.

Dan: That must be kind of a big bummer. Because it’s right there in your hands. I mean, you got $80,000 in revenue.

Sean: Yeah, I think one of the main things was I had no experience and so I wasn’t a very confident salesperson. It’s like, ‘Oh, we can only pay you $300 for this’. ‘Okay, yeah, $300, cool. Let’s do it’. And then it would cost me five times that, just in my time, to try and deliver that not to mention, you know, getting content from other people or whatever. It wasn’t a great year 2014 and into 2015.

Dan: So you have this tough year where you’re spending more money than you’re making, you’re busy, you’re working hard, and you’re losing money. And then you write to say that a year later, Travis Jamison, who has been on the show many, many times hired you to run his agency.

Sean: Yep.

Dan: Did you tell them that you were losing money on your agency?

Sean: What happened was – so at the end of 2014, I was super broke, like, just no money. Like wasn’t, wasn’t pulling my weight in the household at all. I ended up getting a job at the library in Moab, near where I moved. And I was the children’s library assistant or something I don’t know, remember, it was like a kind of a part time gig. But it was all I could come up with. But at some point in 2015 Travis posted something in the Dynamite Circle looking for, kind of an assistant to help with marketing stuff on ‘Supremacy SEO’, which was his site at the time. And I applied. He knew that I knew SEO, even if I was terrible at running an SEO business.

Dan: I’m just trying to imagine you being in this online forum full of people that are doing stuff online, and you’re working on a children’s library, what’s the set of emotions around that?

Sean: I’m super glad you guys had much more relaxed standards back in the day, I definitely would not have gotten in if I had applied with what it would take now. It was motivating to see these people.

Dan: To be clear, you joined the DC so early that I was probably the person who looked at your entry submission. And I was probably at the time thinking, ‘Oh my gosh, this guy Sean wants to pay me money’ because you joined when it started.

Sean: 2012.

Dan: Alright, so you slide into the DC, you’re hanging out in there, but actually you work in a public library.

Sean: At first I was teaching but, yes, eventually I did my own agency, failed super hard, had to take a job at the local library, watching the children’s library room shelving books and stuff. It was cool. I’m thankful for it. It definitely got me a little bit of money when I needed it. It was it was motivating to see the stuff people were doing in the DC, the success they were having. A little discouraging, but mostly motivating like, ‘Man, all these people have found a way to make money. At the very least, I’m a creative person, I graduated from college, I know how to put the work in, it’s gonna happen, I can do it’.

Dan: So you’re working at the library you apply to be Travis Jamison’s assistant?

Sean: Marketing assistant or something I think it was. The only thing I ended up doing was writing a weekly blog post on Supremacy SEO ‘This week in SEO’, it was called. I was there for, I don’t even remember, maybe, 20 weeks ish. And then the guy that was running Supremacy at the time went to work on another one of Travis’s businesses, and they had an opening, and it was just kind of an easy, convenient thing to move me from the guy who writes about SEO to the guy who helps helps run the business that I was familiar with.

Dan: Part of the reason I’m so in love with what you’re laying out here is like, this is the progression, typically, you noodle around, you can take that initial skill set of SEO, and writing and creativity. And you can parlay it as selling services, which I say on the pod all the time, like a very hard way to make a living is to run a services business, because you have to be really good at business. But another way to parlay that skill set is to build relationships around it, and then to get a good job that you learn from. And sounds like that’s what happened here.

Sean: Absolutely. I got good at SEO sales because I did a million of them for Supremacy. It was a great business, it had a strong word of mouth, and we would just get lots of people contacting us, I’d get on the phone with them. And it was a lot easier to sell something that wasn’t my own. I can see the results of the people that sign up for the service. It was easy to slip into, ‘Hey, you need this and we have it. And this is why you should sign up with us’.

Dan: It sounds like you ran Supremacy basically from 2015 to 2018, which is now Smash Digital. Why did you quit?

Sean: I don’t know the exact reason but I kind of got it into my head, as I said before, I’m really interested in the creative side of things and doing SEO for people, I guess, wasn’t scratching that itch. And so I started looking for a place that might, and I kind of settled on ‘Siege Media’, it’s a content marketing agency that uses really good content with really strong visual components, and outreach to build links. I saw that they were hiring for a remote position. And I thought, ‘Hey, maybe really digging into content marketing, and just being more creative would be more fulfilling’, or would lead me to the next part of my life, whatever that is. And so I applied for a job there.

Dan: How’d it go?

Sean: (Laughs) They paid for me to travel out to San Diego, that’s where their office was in early January of 2019. And, with the exception of the library gig, the last time I worked in an office setting was in early 2014. I was super excited. I get to the office on Monday morning or whatever day I started. And I was going to do an orientation there. I got to the office. My memory is they had the heater blasting because, you know, ‘Californians’, and I was so uncomfortable, so hot. And I was there for like three minutes and I said ‘I’ll be right back’. And I walked out of the building back to the apartment I was staying in, grabbed the portable fan and walked back to Siege, plugged it in at my desk and just pointed it out my face. I felt so awkward. so uncool. And they had us go to the conference room to do some training. I took the fan with me. The other thing, I haven’t really talked about this, but I have super bad ADHD. And I didn’t realise how much it impacted me until I wasn’t in my home office that I set up in a way that that works for me, So working in this open office setting with ADHD and not taking Adderall or anything, it was a nightmare. It was like early indicators that maybe this wasn’t a good move.

Dan: I’ve been in that situation where you kind of know you’re in the wrong room. And that’s a very shitty feeling. Because you often did a lot to get there. You kind of build up the expectations of the people who hired you, your family, like everybody knows, this is what you’re doing. And then you start to realise like, you don’t want to be there. That’s a bad feeling.

Sean: It was bad. I came home. I, you know, was a remote worker. We had meetings all the time. I had super tight deadlines. At Supremacy with Travis, it was super chill. It was like, ‘This is what you need to do. Get it done’. No micromanaging. And I thought, ‘Gosh, I left this awesome job to try and grow as a person or, you know, expand my, my skill set or whatever. And, wow, this is a huge mistake’. I think I quit after like two weeks.

Dan: You said ‘I really can’t emphasise enough how much I failed at things from 2011 to 2019’.

Sean: I became an expert.

Dan: Well you did become an expert because soon after you quit you had your first big hit. Can you tell us about what happened there? What was the transition?

Sean: I did a bunch of work before I quit Siege to drum up some consulting projects because basically my wife supported me from 2013/14 until I started working with Travis. That was a long time and it sucked and that’s not what she wanted to be doing with her life and it’s not what I wanted either. I didn’t want to have to rely on her to pay all the bills, put all the food on the table. So I had to put together something in order to quit. Maybe this was early February, I finally got enough commitments together to start providing some SEO service to people.

Dan: Just to flag up your journey here, just another milestone is being able to drum up a book of business, in relatively short order. That’s an entrepreneurial level unlocked, you’re making it sound like, you just went and did it. Well, actually, that’s five years of experience, and relationships and stuff, that lead up to that ability of that kind of if you keep pressing and you keep failing, you unlock these different abilities. And one of them is. ‘Well, I can just go make a living’. And that’s kind of a cool level to get to, because it, it derisks the process, if you get if you push through to that level.

Sean: That’s a good point, that’s one reason why I felt good doing it. I grew as an entrepreneur, I was the guy that worked at Supremacy and rand Supremacy. I knew how things worked, I was pretty confident I could make something happen.

Dan: So you put together the book of business, but I want to get to this moment where you have your kind of first entrepreneurial rocket ship.

Sean: This whole time. One of the reasons that doing PBNs really connected with me is it’s almost like building a mini brand, buying a domain, the domain could be anything. Unfortunately, you’re sticking like this really low quality PBN site on it. But I was always really kind of obsessed with domain names. I just loved the potential of what could be an amazing brand. And so this whole time, I worked at Supremacy, I spent most of my money buying domains for myself. One day, I’ll sell it, whatever, buying expired domains with juice, like, I’ll build this out.

Dan: There are brokers that send out these little newsletters and you felt like an insider by shopping every morning, “Oh, ‘aluminium can recyclerhq dot com’ is for sale”, or whatever.

Sean: Right, it’s like, ‘Oh, I could start an aluminium recycling business. I never even imagined that, but I totally could, this is a great domain’. So I really also started to get interested in the cannabis space in around 2016/17. It just seemed like such a cool new, not at all mature market, with so much potential. So a lot of the domains I bought were related to cannabis. So long story short. In 2017, I bought a domain name for around 200 bucks, and just kind of messed around and built some info content or whatever. But, in late 2018, I put up ‘a best CBD oil page’. And it did not do much of anything. But, by the very end of 2018, beginning of 2019 it started to rank kind of well. I remember making $1,000 in January of 2019 when I started at ‘Siege Media’ and I was like, ‘Wow $1,000, that’s like a million dollars’.

Dan: Because it’s $1,000 and I earned it while I was sleeping.

Sean: Yeah, right. In early 2019, I started really messing around with expired domains, and using a ‘301 redirect’ to acquire one site from another.

Dan: Ok, so we’re gonna have to describe how that works because this is a classic … I mean, Travis Jamison came on the podcast in like 2012, to talk about his ‘301 redirect strategy’.

Sean: So you have a site, let’s say, it’s about teeth whitening. So you have a bunch of content about that. And then you have another site, that is also about teeth whitening, One starts doing better than the other in this example. And so you take all the content that you built out and all the links that you built to site two, and you’re going to move all the content over or combine it or whatever with site one. You redirect it, you tell Google and all the other visitors to your site that, ‘Hey, this page now lives at site one dot com slash best teeth whitening’. And then you do that for each individual URL, you 301 redirect, that’s the kind of redirect it is, it’s a permanent redirect to this other site. So now, every page on your first, your original site, or the site you’re keeping has the link authority and the content and whatever, from the second site. So it’s a way to really bump up the authority of your original site.

Dan: And so an aggressive SEO might hang around on GoDaddy, or on these newsletters or on your new business and say, ‘Well, I’m going to buy up a bunch of expired domains that were pretty well respected sites, but people are giving them up for whatever reason, and I’m going 301 those sites to my money making site’.

Sean: Yeah, there’s definitely tactics that work better than just straight 301-ing out of the box. You want to build a site, you want to have that site have its own identity and its own rankings. It’s way more powerful to do that. I don’t want to say I stumbled into it, but I tried to build out this second site about CBD, and it just wasn’t getting that much traction. And I thought, well, I’ve heard about this 301 stuff, I’ll do that. And I did it poorly, I think I talked with Matthew Barby, he works at HubSpot now, on the ‘Traffic Think Tank’ Slack group, it’s an SEO group, I highly recommend that. He gave me a couple pointers because he’s done this kind of thing before. That was the first thing. The second thing that made this work, that wasn’t a 301 redirect. But I remember listening to the ‘Authority Hackers’ podcast and they were talking about how Google loves fresher content. So taking a post, making some changes, updating it to make it more relevant to this newer to the newer date, and then hitting update was something that would help you rank better. I took this post that I had had for several months, and I changed the date. And then I think I added like one or two products on the post and hit update. That’s it but it changed everything.

Dan: I’m looking at numbers here. $30K and then $50K in April, $80K for May. You’re on a rocket ship. You had an $80K month, you didn’t have any expenses associated with that: $80,000, that’s like somebody just dropped a Mercedes into your driveway in one month.That’s crazy. I love it.

Sean: I still can’t believe sometimes the site was making like $1500 a day, on some days. That’s insane amounts of money.

Dan: So you’re in the middle of the desert looking at your computer screen thinking, ‘What?’ It must have been amazing.

Sean: It was an amazing year. I stopped doing any other consulting work, I stopped doing anything. I didn’t have to do that much. The site had whatever authority Google liked at the time. It was in between updates, so nothing was going on there. And it was just ranking in the top three, sometimes number one, sometimes number two or three for this insane, lucrative keyword.

Dan: I want to flag up a couple things. The first is that this is the next achievement unlocked in an entrepreneurial journey, which is you became an expert. And there’s a lot of experts out there. But now you’re an expert, who’s applying expertise to assets that you own. And so now you can have asymmetric returns where you can’t when you’re selling your expertise directly?

Sean: Absolutely.

Dan: What did you do with the money? You’re selling your time for years, and now all of a sudden, you have more money than you know what to do with? Must be insane.

Sean: It was for sure. The first thing I did was paid off all my credit card debt of which I had a lot because I was just taking risks.

Dan: How much?

Sean: Probably around $15,000

Dan: $15,000 spent on domains?

Sean: Yeah, it’s not a tonne. Domains, marketing courses, buying links. It’s not the most money anyone’s ever been in debt on credit cards, but it was absolutely the most money I could be in debt, because they were all maxed out for years.

Dan: Well it sounds like you did a lot of what folks on the journey do is, they say, ‘Hey, you got to spend money to make money. And so I should take this course and experiment with some links. And you know, I should run a little PPC campaign’. And it kind of runs away from you after a while and you realise, you know, that for some reason that money is not returning money.

Sean: For sure.

Dan: Why did you sell this website?

Sean: I honestly didn’t plan on it, it was a huge moneymaker. But in May, this broker reached out and said, ‘Hey, like, I’m a legit broker, I have a client that wants to buy this website, would you sell?’

Dan: Just for reference, this is May 2019 when this affiliate site just delivered $80,000 into your personal bank account.

Sean: Well, at this point, it was on track to make $80K in affiliate revenue. This broker was like, ‘My client wants to buy this website, are you interested in selling?’ And I was like, ‘Yeah, I guess I’d be interested in talking for sure’. We got on the phone, and they came back after we chatted, with an offer that I cannot talk about, because of NDAs. And I talked to a couple other people – this is the value of a network you know? I dialled Travis up who has sold and bought multiple businesses himself, and I was like, ‘Should I sell, what do you think?’ And he said, ‘I absolutely think you should sell’. It was definitely for a life changing amount of money. And I was like, ‘Alright, let’s do it’.

Dan: What does it feel like to receive life changing money?

Sean: It felt life changing, man. Uust seeing that money hit my account was insane. I grew up pretty poor. I had $55,000 worth of student loan debt that I just assumed I would have when I was 70. That’s a lot of money, plus all the credit card debt, But yeah, it was crazy to see that much money hit my account, it was a huge thing.

Dan: How did you acquire the CBD site that you eventually 301-ed, how did you identify that asset to bring into your portfolio and then how did you ultimately pay for it?

Sean: I paid for it with credit card debt. It actually wasn’t that expensive, which is crazy. I saw this name was expiring. I use a tool called DomCop dot com. But there’s a couple other tools out there like SpamZilla. And what it does is it just lists all the domains that are expiring in the next 10 days. And it runs them through the Moz or Ahrefs or whatever.

Dan: So it judges their quality in terms of their SEO value.

Sean: Yeah, it says, ‘This domain is expiring, it has 50 referring domains. This one has 317’, or whatever. So you can go through and look for these expiring domains that have some juice already and I found one that was …This is actually a crazy story, just how I ended up with this life changing domain that I didn’t know, at the time. I saw it was expiring, I bid on it in a GoDaddy auction and got up to like $750. And that was too much for me, that was too big of a risk, I just couldn’t pay that much. So I lost the auction. What ended up happening was the person who won didn’t pay for it. And I could kind of see that it was still in this ‘pending status’ and did not have a home. And I kept trying to contact GoDaddy and say, ‘Give it to me, I will pay for it, give me this name’. But they just kept saying, ‘Oh, there’s nothing we can do. This process has to play itself out’. And so I watched it every day to see what was happening with it. And finally, it dropped from the registrar. I put in a bid at a couple different places that specialise in catching names that are dropping – meaning it’s put back in the general pool, and these people pour a lot of resources into trying to win you that name and they make money because if 10 other people want it, and they win it, then it goes to an auction again. And you have to win it, and they just keep all the money. And so I was like, ‘Oh, please’. So I watched this name, it took about two months, and I constantly watched this name, I really wanted it. And finally it dropped.

Dan: But it sounds like you had an instinct that this thing was going to be important to your business.

Sean: Yes, because it used to be a CBD site. And I was trying to build a CBD site. Links are great, but relevant links are really great. And having a site be about the same thing it used to be about is the best of all possible combinations. So I really wanted this name. I put in a bid everywhere I could, just to make sure that if there’s a big company that specialises in this, I had a bid and with them to try and get it and no one else put in a bid and I got it for 70 bucks. That’s kind of the unbelievable part of the story, just the amount of stuff that I ended up having to line up to get from A to B is, looking back, it’s just kind of mind blowing. But yeah, I ended up getting this name for 70 bucks. And I built out a site and eventually 301-ed on it.

Dan: What’s it like doing business now after you have a success under your hat?I know you’ve started a newsletter where you have people paying you 1000 bucks a month to write about expired domains, your passion, one of your passions. You started building out more sites. You’re partnering with Travis on a joint venture. So you’ve gone from employee to partner. It sounds like you’re a different type of entrepreneur now.

Sean: It’s awesome. I get to work on what when I want. I don’t have a job, I’m not accountable to anybody. I am super grateful for it. It’s where I wanted to be. And it’s kind of where I needed to be. I’ve been fired from almost everywhere I’ve worked. I’m a dreamer. I spend all day thinking about other things. And now I can just do all the other things I would be dreaming about if I were having a job somewhere,

Dan: You mentioned that you’ve listened to this podcast since the early day is like along the whole journey. It sounds like you had a strong belief that you would sort of get to where you’re at from day one. Which is remarkable given how much time has transpired.

Sean: Yeah, especially in the early days of failing and failing and failing and failing. It helps to hear like, you know, people coming on this podcast talking about their journey, or, you know, people on Mixergy talking about their journey, hearing about their failures or the things that trip them up hearing about their success and just being like, ‘Yes, I will do this, some day’, and just not stopping trying.

Dan: What’s the advice that you wanted to hear? Can you attempt to give advice to people seeking to have similar results as you?

Sean: I guess, given all my experience, my advice would be one to have a strong support network, whatever that means, whether it’s your family, your spouse, your friends, people you are in business with. That has gotten me so much – from my wife to working with Travis. Being upfront and up close and seeing what happens, that was super instructive. Just building out your network organically, and having a strong support structure in place. The other thing I’ll say, for me at least, I really started to experience success once I figured out what I actually wanted to do and embraced that. In my own head, I’m more of a creative person who likes the creative process. And so once I really focused in on that, that’s when I found success, instead of saying, ‘Oh, man, I bet I can make a bunch of money running an agency’. Getting comfortable with failure was something that was very helpful on my own journey. Maybe it didn’t start this way. But like, just saying, ‘Okay, I’m gonna do this thing. And if it fails, it fails’. And I’m gonna, hopefully learn something and take that away and bring that to the next thing and just, you know, keep stacking failure and keep stacking the things you learn from that failure. I really believe if you just keep trying eventually something will hit, it has to. Especially if you grow with each thing, and you learn and you implement that. I think that’s important.

Dan: A big shout out to my guy Sean Markey. You can check him out on Twitter at Sean Markey. He also has a blog at Rank Theory dot com. And then there’s of course Juice Market dot com. It’s a new marketplace for expired domains. It’s got a great design, really cool branding and solving a problem in the marketplace. Expect really good things from Juice Market dot com. That’s it. Remember, we got a Q&A episode coming up, feel free to drop us some questions. And if you want to hear some on the ground, real time updates on what’s happening with our services at Dynamite Jobs, remember you can sign up your company with a free account over there. That’s it for now. We’ll be back at the same time, same place next Thursday morning. See you then.

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