Ask Amanda About Marketing – Episode 28: From the Ground Up

Who here has wondered what goes into starting a successful site from the ground up?

raising hands

I spoke with digital entrepreneur Dan Wesley, founder of and chief evangelist at, about what it takes to take a site idea and turn it into a full-time gig.

Dan talks about:

  • His journey from nuclear medicine to entrepreneurship
  • How to continue learning and acquiring industry knowledge
  • Why content development is a necessary part of your marketing strategy
  • How changing the title of an article can transform your content

Enjoy! I’ll leave you with this quote about content:

“It was going to be extremely tough for us to establish authority and credibility if we weren’t a source for something.” – Dan Wesley

Mentioned/Related Links:

, Ask Amanda About Marketing – Episode 28: From the Ground Up

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Full Transcript:

Amanda Milligan: Welcome to Ask Amanda About Marketing, a podcast in which I, Amanda, or occasionally a special guest, answer your questions about inbound marketing. Straightforward, right? If you want to submit a question, email me at [email protected]. I’d love to hear from you. Let’s get right to it.

On today’s episode, I am pleased to be joined by Dan Wesley, who is the founder of Credit and is also working on a variety of other projects including being one of the evangelists for Welcome to the show, Dan.

Dan Wesley: Hey, great! Amanda, it’s nice to meet you and to be here.

AM: I’m excited to have you. So in this episode, we’re going to talk a lot about some of the sites that he’s built from the ground up and I’m really interested to get your perspective on how you were able to develop like growth and marketing strategies along the way.

To kick things off, can you talk about just your overall career background like, you know, the generality of what you’ve accomplished so far?

DW: Yeah sure thing. So, you know, my background is definitely a unique mix of medical science and business, which fortunately has helped me to train me to see things a little bit differently and at the same time, a little bit interestingly. So, you know, I’m a blue ocean, non-linear thinker.

With credit loan, I was certainly inspired by those “make money while you sleep” commercials. This is a 2003 late-night TV and you know, just knowing that, having a really stable nice job…I think that’s, you know, where “side hustle” came in, right? It was just, you know, there’s some intangible ability here in a virtual world to create value and also, possibly just some side money. That’s all I was inspired by. Little did I know that an entrepreneurial spirit was calling me. I’m in my mid-20s. No kids. I kind of felt it was now or never in terms of risk-taking, you know, like I said—nonlinear thinker. I live in the abstract.

So, you know, a great job, a nine to five. You know, it just didn’t fit in my personality. My mom is a real estate agent and, gosh, did it for 30 years and she used to have this very flexible schedule. And obviously performance-driven, right? You either sell the house or you don’t and I love that. So I think you know mom’s genes definitely were inspiring. I was so interested by that “side hustle” of organic search.

Google, I think, started in 1995, you know, we’re eight years into when I kick things off, you know still very much in its, you know, it’s in its infancy. Honestly, where else in the world could you kind of be the ultimate underdog and compete with a limited amount of resources and mitigate that with hustle. That was what really drove me to it.

AM: So when you were starting these different projects back in 2003, how did you know? Like, at what moment did you think, I have something here? When did things start to click where I’m putting the work in and I’m starting to really see a payoff?

DW: It was a long process, but I could tell you the moment and then I’ll work my way backward. So I’m walking to the Tampa Bay Buccaneers football game and it’s just me and my wife and it was a pretty long walk as we had rather nosebleed seats at the time. So I’m walking and my mind’s going about, you know, what I did the night before and I hit me like a ton of bricks. It was this level of like peace and conviction.

The whole, like, 1 and a 1/2 mile walk up, telling her about the whole thing like, oh my gosh, I just realized the opportunity sizes here. And she’s kind of looking at me like, let it go, we’re gonna go watch football. That was that moment and I want to say it was like 2006, you know about three years into this moon-lighting but honestly really after that conviction moment, things didn’t really take off until 2008. It was still another two years to where I knew I had something here, but I wasn’t willing to take the next the next step.

AM: And then you end up, you know, getting like an eight-figure payout for Creditloan, right? Like that went wildly successful.

DW: Yeah, I hit the—you know, I say 2008—that’s where that proverbial fork in the road happened and I started making more money with this the side hustle than I was making with my paycheck and you know, I love both worlds. I love the security of the nine-to-five. It’s the structure, right? The health insurance, the routine. But, I got to that fork in the road. It was April 2008 and I said I gotta see if there’s something here. Otherwise, I’ll regret it, for the rest of my life.

So, two months after I quit my job, we find out we’re pregnant.

AM: Wow.

DW: And it’s like whoa, okay, more pressure now this is a good thing, back’s against the wall. Four months later, we obviously had the Great Recession. I was selling all of my leads at the time through Citi, who we know basically needed a half-trillion dollar bailout. I—again, I did want to go back [to] working at the hospital. I just had this mentality of, I’m not going back. I’m not failing and that fear of failure still drives me today.

AM: I love hearing kind of like the backgrounds of how people end up in marketing and, you know, building websites because I feel like nine times out of ten, nobody started doing that. Everybody I know you know at Fractl that I’ve met had started doing something else and then something called to them about this industry and getting into this kind of work. So that’s why I appreciate you talking about that background. I feel like a lot of people are in your shoes or want to do what you did. So I think this will be a really valuable conversation.

So in those early years, like you said, you had that epiphany of a moment and then it wasn’t until 2008 when you really started to see that pay off. What—and this is a big question—what were some of your primary strategies at that time to really get the traction you needed for Creditloan to succeed?

DW: You know, I think a lot of it was the knowledge base. I knew I needed to basically just never stop learning and if I committed to that, I always knew, I’m gonna find out if I truly love this or not. There’s going to be potentially this threshold or inertia that I will hit. I just never ran into it. I kept wanting to learn more. Then the more I learned, the more I applied, the more success I had.

There was just this really intrinsic compounding that I never expected but the thirst for information was so key because I started this with a $5,000 tax return. Essentially, it was no investment, all bootstrapped. Again, I just knew if I could out-hustle the bigger organizations that there was that potential here.

AM: So from a marketing perspective or from a growth perspective, what were some of the things that have you started doing and then as you were gathering all this information—because I imagine it was a whole new world for you, right? You’re diving into this and you’re like there’s a lot that goes into this, you know, just consuming information. So, what did you not expect to be so important or to be so pivotal to that growth early on, that ended up really being a major component of what you were doing?

DW: I think underestimating certainly the amount of time that’s involved. Just knowing that Google was evolving at the time as well as the revenue streams, the traffic streams—all tied to Google search. Google evolved with algorithms; so did I. Staying progressive was pretty key but somewhat misunderstood. I could tell you I had very good days and I had very bad days of losing all your organic rankings because of an update and the revenue—I mean, it was that binary. It was gone, and like, whoa what just happened.

Then, on the flip side, seeing a huge update and I lift and tripling revenue for the day. Yeah, that was the key. One thing that I think was a disadvantage but certainly had me work harder was you know—2003, there wasn’t the Neil Patel’s of the world. There wasn’t the maturity of information. It’s certainly content shock now but you didn’t really have those—my conversations were with Rand Fishkin on Just going back and forth in a private message.

It was so limited that you didn’t really understand. So, there were so few guys, Eric Wards, God bless him, he just passed away not too long ago. But you know, you had some folks that you could lean on but I think that’s one reason it took so long. You kind of underestimate what you need to get done. And you know, you’re not Google. You’re just trying to emulate them.

AM: Yes, try to keep up with what they’re doing, which I find so fascinating about this industry in general and I explain it to people. The entire industry can literally change overnight if Google decided to do something. It’s hard for people to really grasp I think.

DW: It’s very true.

AM: So like you said there weren’t as many resources, as many kinds of leaders who you can get this information from then. People have access to that kind of thing now. So based on what you learned then, what advice would you give to people now who are starting something from scratch, who have access to that information? What would you tell them to do to increase your chances of success?

DW: Yeah, I think information can be that double-edged sword because if you’re just starting out, you may not know who Neil Patel is and whether he is that authority. I never went to conferences and they were going on back then. I didn’t want to be influenced by other people. I think it was resistance. I didn’t want to cloud my thinking. I had a certain way that I wanted to approach things. Again, information is already limited as it as it is but you know in hindsight, that that could have gone either way.

So climbing through the information I think is going to be very difficult for somebody that’s just starting out. I look at Google, and somewhat of a nonlinear analogy here would be if you type in “auto insurance” in Google. Let’s just say you don’t see Geico and State Farm and some of these other brands. You start questioning the credibility of the search engine. If you’re looking for information—how to do SEO, how to do these certain things—you look at Google, you know what they’re objectively ranking. That’s a great start.

I mean, I’m not saying, hey number one and it’s Neil Patel that you just you know, go all in and trust it. But, I think you have to have a composite approach. Take what Neil says, take what you think, take what Brian Dean says, Gary Halbert. You’ve got to take a composite approach.

Another thing too is, what are you trying to accomplish? To me, there’s always an index relative to what you’re trying to accomplish. Competitors, right? You know, if you want to be Nerdwallet, what’s Nerdwallet doing? You know, where are you? I think the composite competitive analysis—at the end of the day—it’s in a long-winded fashion, it’s an equation.

AM: So, Dan, you’re a client of ours and my question—we’ve been doing content marketing for you—is how has content marketing played a role and when did that really step up to be part of your strategy?

DW: Yeah, I think what we were missing from our brands was really the data-driven original research. Things that were originating from our voice, per se. Being able to really take this market data and these studies and package them, whether it was a juxtaposition to something in the news cycle or what have you. It was an angle that we weren’t exploring so it’s going to be extremely tough for us to establish authority and credibility if we weren’t a source for something.

That’s been, I think, the biggest benefit because you got to check the box. You gotta create these articles and other forms of “Best in Class” content, but the best you can do is be topically comprehensive. That kind of stuff is not “link-worthy.” People are not going to link to the Wells Fargo Cash Visa review, right? But you gotta check the box. You gotta find a different arc to tell that story.

At the end of the day, if you want to rank for Wells Fargo Cash Visa, you’ve got to have that piece of content on your site, right? So the market data is what allows us to gain the links and the credibility. Therefore, really intrinsically, as you know, the quota of all is: as the tide rises, all the boats in the harbor rise. That’s what helps us unlock it, is the market side.

AM: When did you come to that realization? Like you said, you were doing a lot of competitive research, you want to be the Nerdwallet—was it seeing other brands doing that kind of work or like what was the spark? Like, we need multiple types of content in order to succeed here.

DW: Yeah, you know, given Google’s 200 ranking factors, I knew they were [about] simplification that yes, there’s a lot of things that are conditioning the algorithm; but at the end of the day, [with] so many websites—so many nefarious players as well, Google had to have this threshold of trust—this proverbial whitelist I call it.

And who are the people on that whitelist, right? You know Forbes, CNN, potentially Nerdwallet, right? So what were those guys doing? They were creating these stories that were just incredible, works of art I call them. What I noticed the pattern was—they didn’t have a linear connection between things that they wanted to rank for that had bottom funnel commercial value. There wasn’t this causation between the two, so here they are creating tangential studies about average debt in America in 2017 and then ranking for credit cards. It was really seeing those guys and how they were building their brands that sparked it for me.

AM: It’s funny because you used the same word we do, which is the tangential content phrase. It’s hard sometimes to explain how content that’s not completely tied to your brand message can be so beneficial to what you’re trying to accomplish, especially if you’re really trying to diversify your backlink portfolio and are really just get your name out there in general. It could be so effective.

DW: Listen, in the office this week, I’m having a healthy discussion about average grade level, you know, and one of our guys is—he’s dug in and he’s saying, look, it’s a 12-13-14 grade level writing and I said, yeah, that’s intentional. We want to attract that eighth-grade level that’s for usability, readability, all those things.

At the same time, when you add these high-fidelity data-driven articles, it’s—one, we know we want to attract a new audience; two—it’s a signal to Google. It’s saying wow, there’s some Academia happening here that they’re gonna, I think refactor the algorithm for your site differently.

So that was a funny conversation because I said, hey man, 6 months ago, we weren’t even fighting over average grade level. 12 months ago, we weren’t doing this. I’m like, we have come a long way to spend one-hour debate average grade level. So that’s not a bad place to be.

AM: Right, and that I think what you were saying before about building authority is key there. Because yeah, there’s so many types of content created. It’s good content nothing wrong with it, but when it comes to those signals to Google where it’s like, we created this and this is something we really know about etcetera, it can really go a long way.

DW: To me, that’s the name of the game—it’s trust and authority. I don’t know what that threshold is for when you start ranking faster, but we know it happens. We know the lag time between creating a competitive article that you’re targeting a certain keyword. I mean, it’ll go from it taking, say, two years to rank to sometimes two months. It’s really this compounding effect, which it’s really hard to explain it at times to folks.

AM: Yeah it can be. So over the course of the last decade or so and you’re building all this out, how do you come up with your—this is also a very big question so however you want to answer it if there’s a particular piece you want to dive into—but what do you like? What inspires you? How do you come up with ideas? Like what’s your process? You say you’re a non-linear thinker. How would you have this nebulous task in front of you? How do you tackle it? What is your first step?

DW: It definitely requires definitely some creative ability because you think of topics like I mentioned Wells Fargo Cash Visa. Finance, in general, is boring but at the same time, I also feel because it’s boring, nobody’s been able to figure out how to make it interesting. So trying to find just these arcs within a narrative.

A good example of like that that Wells Fargo we did a Citibank review and it started with just at the title level we said, “How Citi Became a Hundred and Ninety Billion Dollar Company” instead of the normal title [which] would have been “Citibank Review.” So what that did was—for the creative direction and the liberty for the writers was they started from there. They said, okay, well, how am I going to build this arc to one ninety and a hundred ninety billion dollar market cap.

We saw that just changed everything from the writing. So, that’s not even four months old. I mean, I’m still learning things. I wish I learned that 15 years ago. But again, you never stop learning and looking for ways to, build those lateral connections. And again, it’s not easy. I mean, lots of brainstorming and then trying to restitch it, you know in a linear way. It’s definitely a challenge.

AM: Do you have similar approaches now when it comes to trying to learn everything? Are there certain resources you return to or certain things you look at?

DW: I think it’s tough to know as much as I wanted to make that portion prescriptive, I always find it’s impossible to try to scale it and or emulate. You know it when you see it, I think that’s something that—you know, you see an awesome story on Business Insider or what have you. Whether it’s tied to the news cycle or timely, we had a piece—the most viral piece we ever did—and this was I think back in, gosh, 2008, was how the average American spends their paycheck. So the ubiquity, the relativity to the consumer and this was the days. The minute we put it on, it blew up.

To this day. It still attracts backlinks. We still refresh it. It is still a traffic monster because you know, everybody gets a paycheck, right? Just that seeing what everybody’s spending money on, I don’t know. It’s creating a piece with the optimal level of dissonance, right, pairing to uncommon things or something that’s just unbelievably believable. I think that if you can scale that, that would be super, super valuable.

AM: I like that phrase unbelievably believable, I’ve never heard that before.

DW: Yeah, it’s just these intersections of just dissonance. Again you have so much content out there. Attention span—you know, eight seconds now. Device fragmentation. It’s hard to keep somebody captive. So you gotta create something that’s going to get their attention in a way that I think invokes that Curiosity Loop, right?

AM: And it’s so true what you said like everybody gets a paycheck. So everybody can relate because we’ve seen that. If people can’t see themselves in the content you’re creating, they just don’t, I mean, they’re not going to care. They’re just going to move on. It’s like making sure that they can see while they’re reading it like, oh, like I fit into this somehow. This has been like, at the forefront of our minds.

DW: You know, that’s what’s with as well as I think about that domain as the ultimate versatility, right? The reason I bought it—I had my second conviction moment in terms of a future opportunity that was 10 times stronger than I ever had with Creditloan and it was because you know, essentially the sediment in the ubiquity of a quote.

Could I ever find a way to dovetail that to upper funnel content? In some of the examples I’ve tried, I just haven’t had a lot of time to spend on it—this one quote will make you think twice about having life insurance, right? You’re building a story. It’s a form of almost thought leadership to where—can you conceivably get somebody from the top of the funnel to the bottom of the funnel in one article, right?

We all know consumers buy on emotion and not logic so it’s been a really interesting project. Like I said, get a quote on anything, right? Auto insurance, personal loans, home security. I mean, we could be Geico, ADT, SolarCity, Angie’s List, all in one site and kind of truncated that here internally as we could be the Amazon of lead generation. Big opportunity, but you got to build a ground floor too, so very important.

AM: I mean it’s a fascinating idea and it seems like an overwhelming amount to plan. So when you’re going for that—like, I love that concept to take somebody from the top of the funnel to the bottom in the same piece. I feel like that’s such a rare thing. When you’re generating content in all these different verticals, what do you prioritize?

DW: Well, I think we definitely do not deviate from the Creditloan playbook, you know, the idea is we could create very similar, let’s say auto insurance data-driven studies, a review of Geico—the ability to just make sure we do that well is the primary focus.

The one quote life insurance, those are a kind of our venture place. You know, that’s our R&D. Can we figure out how to how to do both? Because I think what’s missing from honestly, it’s just the brand awareness. Once you get that brand awareness, look how playful the brands become, right? Geico: camels to cavemen. It’s because you know them for insurance.

Imagine having that same level of awareness. I’ll just take a tenth of it for now. Imagine it has that same level of awareness and then our ability to play with the sediment of a quote and how it makes you feel, it would be unlimited. So that was an epiphany for me. You can’t be both, there’s brand confusion. If you’re too heavy trying to push this agenda with the one quote life insurance. So take those shots when you can, but stick to what clearly has worked on Creditloan.

AM: Yeah, I love that perspective. Brand awareness is such a hard thing to measure and yet it’s so important. It’s a harder thing to put numbers to. I’ve never heard it described that way where it’s like, over time, you’re able to expand your possibilities so much more. People know who you are.

DW: Yeah. It’s you selling it. They’re selling experiences, right? Coca-Cola. They’re trying to sell you an experience. GoPro, they’re selling the benefits. That’s a key component of just psychology of sales and behavioral economics. I mean, when you go into Home Depot and you’re looking for essentially a drill bit, you know, say 2, 2 and quarter inch you don’t really want to drill bit. You want a two and a quarter inch hole.

That’s what you really want, you know so fast-tracking with ad copy and design and really thinking of the end state for the consumer. Don’t sell the specs; sell the benefits of this. Again, yeah, that’s like two years ago. Those are epiphanies, right? You never stop learning.
AM: I think that’s a perfect note to end on actually thank you so much for being on the show. It was really insightful to kind of see into your perspective as you were developing these sites and having those experiences. And yeah, thank you for being here.

DW: Awesome. Yeah. Thanks for having me.

AM: Thanks again for listening. If you enjoyed this episode, click subscribe. Don’t leave me with the realization that I’m talking to no one and please rate and review on iTunes so I can keep making this podcast better and your lives easier. Take care.

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