Wolf in Raven’s Clothing: Interview with Jon Henshaw Part 2

30 Minute Read | Digital Transformation

As you might have been able to tell from Part 1 of my chat with Jon Henshaw, we had A LOT to talk about. Apart from just two friends catching up, we talked about the early days of SEO and in particular, his original SaaSy start up, Raven Tools. The SEO landscape was very different in 2007 and Jon was the first to use cloud-based services in the creation of SEO tools, which seems crazy because of how dependent we are on it these days. We also talked about his background in psychology helped him with empathy – something that is underused in our industry, which is better known for manipulation. It was a great chat!

And it looks as though he enjoyed our previous encounter too…

Now, in part 2 of our mammoth interview, we talk about everyone’s favourite link building and also about what it was like to sell his original baby, Raven Tools – then start up his current venture, Coywolf.

Specifically, I get answers to the following burning questions:

So if you want some bang-on link building tips, or you’re just curious to know Jon is up to these days and what’s next for him as well, now’s the time to get stuck in…

Do you think link building is still relevant today?

Jon: Yes, but I think it is different than it was before. Today, so many of those outreach emails are just atrocious. But I can tell you, when we were still an agency, well over a decade ago, I wasn’t doing it that way. I was doing what I described earlier, which is getting digital empathy, getting to know who the heck I was even talking to.

In fact, I can give you a great example…

We had a client in the finance area, who did types of financing that are not thought that highly of. The best sites for this client were finance sites and finance blogs, and consumer-related type stuff. And that’s where we wanted to get links and mentions.

I already knew that if I told them straight off what I was promoting, particularly in one of those stupid emails I’m telling you about, I’d never hear from them. It would be 100% rejection rate. Knowing that, and knowing the mindset of these bloggers, I knew that I had to approach it in a different way.

Empathy is trying to understand how the other person feels in a certain situation. Well, how do you do that? You put yourself in the situation. It’s just that simple. So, if I were somebody running this finance blog, how would I feel if I received this type of thing?

Then you start asking yourself, “What would I respond well to?” The thing I would respond well to would be 1) not that, and 2) money. But then a lot of people jump to, “Oh, if I offer money with that, they’ll take that.” But no, that’s not what you would respond well to. You wouldn’t respond well to that plus money, but you would respond well to money tied to something that is more doable.

And so what I would do is I would reach out to them, and instead of going after the thing I wanted, I went after the thing they wanted. And what they wanted was just kind of straight-up legit sponsorship or advertising, something that is aboveboard. They started writing maybe out of altruistic reasons, but they also wanted to make some money off a blog. That’s kind of what a lot of people do.


So I would say, “Hey, I would love to just run an ad,” or “do some sort of sponsorship, or sponsor email newsletter,” you know, “and commit to three months.” And by the way, my response rate was huge.

Woj: That’s great.

Jon: And so two things will happen. One would be through running those ads on that site, I would find out if that was even a good target site. Because it’s not just getting a link from a site. It’s also finding out if anybody even goes there and whether they even click on these links. That’s pretty important. And then the other thing is, I would be establishing a relationship with the site.

If I were just sending those stupid emails, I don’t have any relationship because they’re never gonna reply to me. But because I went and communicated with them and gave them something I knew that they would want through my digital empathy… (I like this now!) then I was able to actually communicate with them. I was able to establish a relationship over months because we’re corresponding and I’m paying them and we’re doing some display advertising or setting up something new with their email newsletter.

And so now there’s this rapport. So, a few months go by and I find out that people click on these ads. So that’s worth my time and worth the money for our client. So I know that they have my target audience, and then I go, “Hey, do you think there’ll be any editorial opportunity where I could write something?” “I definitely would wanna link to my client, but I could write it for free.” And it became a very casual conversation about this. And they would say yes, or no.

It took longer to get there, but I was able to get through. And I can almost guarantee you that my success rate using that method, and effectiveness for my client, in the long run, would easily smash what cannot be that successful a method, sending those one-off, spammy, automated outreach messages.

Woj: I like your method because it enables you to test things through the advertising. Did you do that purely via email or did you pick up a phone and call?

Jon: Email.

I hate phone. I don’t wanna talk to anybody on the phone. It’s, like, the worst thing I can think of.

Woj: Interesting.

Jon: I like electronic communication. I think people more and more prefer electronic messaging. I know I do, and I know that more and more people seem to share that sentiment than they have in previous years.

Woj: Yeah. It’s interesting, though, because email automation and message marketing is so saturated now… how is it even effective? It just makes me think of things like Instagram, where you’ve got the influencer and brands now, I guess they’re using influencers to promote their products. But there’s push back in the community between what’s a realistic shot and what’s a fabricated shot. Whereas in the early days, you could get away with showing consumers Kim Kardashian holding a handbag and the brand paid her. But now, people know when it’s a fake shot or they’re being sold to. It’s kind of like the link building emails.

Jon: You can’t send link building emails anymore with you holding a handbag. It just doesn’t make any sense!

Woj: Yeah. It should come with some sort of warning label. Do not add handbag to email. Reminds me of this warning for a hat I saw. There were three stick figures. The first one showed the hat on the guy’s butt. It said, “No, incorrecto.” The next stick figure had it on his foot. “No, incorrecto.” The last one was on his head. “Si, correcto.” So anyway, just in case you don’t know how to wear a hat.


How to wear a hat

Jon: Right, those are good instructions.

What’s one of the craziest things that you remember, during the time you were running Raven Tools?

Jon: Oh, there’s so many stories of craziness… I was at Raven for 13 years or something like that. So we’ve had some interesting years. I think a story that most people are aware of is when we had to get rid of the rank tracking. That was extraordinary in my life. When we did that, we lost half of our business in two months or something. It was crazy. We regained it. In fact, we ended up getting more customers than ever because of the site auditor that I built. So that was good.

What was the process of selling Raven Tools like?

Jon: It was interesting because it was my first time ever. Everything else had always been a giant failure. I never expected to sell this. It’s pretty funny. Because we had built a lifestyle business; I’d never, in my mind, had the objective of, “Let’s get this to a place where it could sell and be amazing.” That’s a very different way to run a business. Ours was more about: we care about the people (our employees), we care about the culture, we wanna have fun, you know, we just wanna enjoy going to work. We don’t wanna be under the ridiculous pressure of owing banks and VCs, as if the whole reason why this exists is so we could sell it. That was never, ever the idea.


But when it came to it, my business partner, Scott, and I we were just ready to move on. We got to a point where it had been a long time. It had been a bit of a roller coaster. Really good stuff, really bad stuff, just all over the place. And we were ready for something new. Unfortunately, because we built it as a lifestyle business, we were tied to it. We were chained financially, to the business. And so even when we were ready to do something different, we couldn’t. So there’s that aspect of it.

And then there’s the other aspect of it, that you need to have your stuff in order and straightened out, in order to properly sell a business. Well, I’ve never sold a business before. I’ve never tried to even prepare a business to be sold before. So that was very eye-opening. I mean, just the amount of things we had to have in place, the agreements, all the stuff. Because the company that bought us were approaching it from either the perspective of building a real business, going public or selling it. I mean, it wasn’t going to be a lifestyle business anymore; it was going to be a business business.

Woj: They gotta do the due diligence process.

Jon: Yeah, so the due diligence was super eye-opening. It was a lot of work for Scott and myself to get our acts together, because of all the stuff that was required to make it a sound purchase, for the purchaser. We had digital copies here, we had paper copies over there. It wasn’t organised in a way that was like, “Here’s your box of stuff. This is everything you need,” you know, “let’s sign the paper.”

So, it took a while for us to find all those things. It would have saved us huge headaches and time, if we had organised things better. And what I learned from that is, that’s how you have to approach any business that you do.

Even if you see your business as a lifestyle, you’ve still got to have all your due diligence in order because you never know what the future is going to hold. You never know if you’re gonna wanna sell something or get tired of it – whatever it might be.

So I have taken a very similar approach to the stuff I’m doing with Coywolf. Even if Coywolf is what I would call, “a company of one.”

There’s a guy named Paul Jarvis, who wrote a book called ‘Company of One,’ which I encourage people to go out and read. It’s awesome. I’m very much a company of one. I have a full-time job. I love my full-time job. This is just something I do in my own spare time. But at the same time, it is a real business and I do want it to become something bigger sometime in the future.

That’s one of the things I learned from this process of selling Raven. Right now, there’s a thing I’ve always wanted to build and I needed a software developer to build it. So I made sure that I had the proper contracting agreement in place, which is exactly what would be needed if 10 years from today, what I’m building right now ends up being awesome, and a lot of people like it and use it and it ends up making a lot of money, and then I decide to sell it; I’ll already have that thing in place.

That’s the biggest thing I’ve learned is being able to keep things in order. That’s one of the things I’m working on for the Coywolf Pro membership I’m putting together… I’m putting together an article about how you need to structure everything. These are all the things that you’ll be asked for when you sell a company. And you need to have all these things organised like this in order to do that. With the idea that whoever reads it will have that as a blueprint for how they can organise their stuff, so they can one day do that if they need to.

Woj: That’s really cool. Like, a due diligence checklist.

Jon: Exactly. It’s not new, it’s just new to us. You know what I mean? The only reason why I’m gonna put this together is because otherwise, nobody’s ever gonna see it until they have to see it. And by then, it’s too late, like it was for Scott and me. I mean, it wasn’t too late but it was too late in that like, “Oh, my goodness, we have so much work to do now, to get all the things together.”

What would you do differently if you had to do a second time around? Would it be that preparedness?

Jon: I’m doing that a little bit right now. I’m in a position that a lot of people are in, which is they have entrepreneurial aspirations and they also have the realities of life – which is you still have to make a living and pay your bills and have health care.

So this whole concept of “company of one” really resonates with me, this idea of not growing for the sake of growth. Not thinking that the only way to measure success is by how many people you’ve hired. Or that you have to do something a certain way, because that’s what people said. It’s funny, I love this digital empathy thing – going back to that, it’s more about doing what you wanna do. What do you think that other people want to experience? And doing it in a way that’s manageable in your life.

I would like to think that, if I were to do it all over again… let’s say Coywolf was the only thing I’m doing, I would like to think that I would continue to do Coywolf the way I’m doing it now, just more. If I were a full-time entrepreneur, I would still approach it as a company of one. I would still be very wary of trying to have it grow in the traditional idea of how a company should grow. And instead, I get to decide what matters to me, not what everybody says should matter to me. I set my own goals and what is meaningful to me.

And, you know, one of the things that Paul Jarvis talks about in this book is that, oftentimes, you can actually make more money for yourself by approaching it that way, than assuming that you have to delegate and have all these employees and do all these things. You can end up actually happier by doing a little less.


You can actually pare it down and make double what you would have made if you had triple the revenue. Because the amount of cost, time, effort, and legal, and everything else that’s involved, ends up eating your time. And you don’t make as much money. You can still have employees, and you can still do certain services, and still run it as a company of one.

One of the things he talks about is, a company of one doesn’t have to be a company of one. In fact, you can be a company of one within a giant company. It is a mindset and how you approach business. And of course, not every company will allow you to be a company of one in that sense. But I think you have to figure out what you want to do with your time and ultimately what your goals are. And it may end up being that in order for you to achieve whatever those things are, you have to painfully shut off people and services.


If you can pare it down to just the things you wanna do but you do those so fucking well, people are still willing to use you even though you don’t do the whole package. You might even be able to do those things for other agencies that do provide the whole package, but they’re really outsourcing to you. And you’re getting paid plenty to do it. You see what I’m saying?

Woj: Yeah.

Jon: So if you want to do technical SEO, and maybe a handful of other things, and you wanna do it in a certain way that doesn’t require you to always have to be there in person or being managing other human beings, you can achieve it. And it’s possible to achieve it in a way that you’re making more than you’re making now. That’s the concept.

So, what is a coy wolf?

Jon: Coy wolf was an interesting one to pick for a name. And believe me, I thought about, “Are people gonna misinterpret coy in front of wolf? Like, “Weak wolf.” Because that’s not what it is. In North America, we have a hybrid coyote and wolf species, which is called a coy wolf. They are a little smaller than wolves, a little bigger than coyotes. And they’re incredibly smart. And they adapt to their environment amazingly well.

You can find them living in suburbia, and they will thrive because they’re so clever. And I love that. I love the whole idea of that animal and how it could relate to our industry and Google and Internet, and all that stuff. Because, as you are very well aware, this stuff is changing every day. It’s crazy. Especially if you do SEO, it just changes every day.

Woj: Oh, yeah.

Jon: The most successful people out there are ones that can adapt quickly. So, for me, Coywolf was sort of the perfect embodiment of that; it’s this thing that can adapt and do it in a way that no matter what happens around them, they can still thrive. So that’s where that comes from. And obviously, it’s another animal just like Raven.

Raven Tools logo

Woj: Trying to start a zoo or something?

Jon: Right, I’m trying to start a zoo of apps! That comes from the O’Reilly books. So the reason why I picked Raven was because I loved those books. They’re the ones that have programming languages and things like that. And they always have an animal.

Woj: Oh, with the white cover?

Jon: Yeah, they have a Emu, they have a snake, whatever. I’ve always loved that because the animal’s always associated with the language, with the context. And so I wanted to have that for my company because it’s the memory thing. With Raven, when that was started, SEO was still considered kind of a dark art at the time. So I loved the reference, that was like Edgar Allan Poe, and it just had this darkness to it. But at the same time, ravens are considered the smartest birds on the planet. And they use tools and such. So there’s this tie in, this fit of the characteristic of the bird, and also, how SEO is hard and how people saw it. It was a really good fit back then.

O'Reilly books
(image source: ars technica)

Woj: I always thought it was something to do with Edgar Allan Poe.

Jon: It was the same sentiment.

Woj: I saw it as the raven sort of perched up, you know, sort of looking over the SEO community.

Jon: Darker, but smarter, very clever. So, that theme carries on into Coywolf, where I wanted to do another animal, a short named animal, something that would be memorable. From a purely marketing standpoint, I really liked the idea of a dog. Simply because it is in the nature of a huge majority of the population to immediately identify with dogs.

I wanted the visual brand to be something that people would immediately connect with. I wanted it to be something that they would want to wear, just like with the original Raven logo.

Woj: It’s a very cool logo.

Coywolf logo
(image source: Coywolf)

Jon: Thank you. I had an amazing designer do it, and we spent a lot of time getting to that particular design. So I’m glad you like it. So I think that combined with the characteristics of the coy wolf that I just described, and the fact that hardly anybody’s ever used it, was very helpful.

What’s the intention behind Coywolf?

Jon: I would say that the driving force behind it is my curiosity. I have never-ending curiosity.

That’s why I love our industry so much, because of the fact it changes so much. I love to experiment. I like to try new things because that’s how you discover things.

I am not and have never been the type of person who likes to read other people’s books of how I’m supposed to live my life or run my business. I’ve never been that person… Which has contributed to a lot of failure in my life. But it’s also contributed to…

Woj: Success.

Jon: …to success. I mean, you get a little bit of both, sometimes more than the other. But that’s my personality. And I want to try things that I haven’t tried before, and I don’t think other people have tried before. I want to try things that other people say you shouldn’t do, but they haven’t given me a good reason to not do them.

I think that too many people follow the mould of other people, and the structure that has been handed to them and they think that’s the only way. They might even passionately defend how they’re doing something because that’s the way you’re supposed to do it in this book they’ve read. And I think that’s a very poor reason to be passionate about something.

I think you should have passion about something because it works for you. You should be passionate about something because you’ve tested it and tried it for yourself. But you shouldn’t be passionate about something because you’re actually defending some other person who calls themselves an expert. There’s no fun in life if you’re just following somebody else’s way of doing it. I conform plenty, but I’m not a conformist when it comes to entrepreneurism and how I want to do things.

Woj: This explains why I haven’t joined a cult.

Jon: Why you haven’t joined a cult?

Woj: Yeah.

Jon: Right. If I was more of a conformist, any given cult, I’d be like…

Woj: Sign me up.

Jon: Exactly. I think that if you spent any time poking around the stuff I’m doing with Coywolf, you would see that everything I just said is true. Because for some people that have been in the industry for a while, if you were to see what I’m doing you would think I’m completely insane.


I’ll give you some examples.

I love the new top-level domains. I’m just in love with them. I want to experiment with them, I just wanna do different things with them. One of the things I’ve never seen anybody do is build a site and a brand with multiple top-level domains focused on different areas. I’ve never seen anybody do it. It might be being done, but I haven’t seen anybody dumb enough or crazy enough to do it. So I’m gonna do it.

And so if you were to go to any of the Coywolf sites, it looks like this. The nav has something that says pro, it says news, it says community, it will soon say reviews, it will soon say app. And you click on them and you go to that section of the site. Except you’re actually going to a different site. You’re actually going to a different domain. So when you click on pro, you go to coywolf.pro. When you go to news, you go to coywolf.news. When you go to community to go to coywolf.community. And then it’ll be coywolf.reviews. And then it will be coywolf.app, which will be the app that I have, that I’m making right now.

Showing top level domain options for Coywolf

I love that concept because it’s so ridiculous. But because of the flexibility and freedom that gives me, from one perspective, I can have one of the sites go down but the rest still work; it’s not all one system. So I like that. I like it because since the app will be built off of Coywolf.app, technically, it’s its own system. And if for whatever reason I ever want to sell that or do something else with it, that just moves over, and it doesn’t affect any other part of this whole site that people have come to know.

It’s kind of fun to build more than one property because typically, you’re dependent on one domain. Well, in this case, I’m actually independently building up multiple properties all at the same time. And it’s not spammy, because they’re all connected to the same company and they’re related. It’s not like you’re doing some crazy cross-linking. No, this is legitimately a service. And it happens to be that each of these specific things lives on their own domain with their own code base.

Coywolf Pro

I’m sure somebody’s gonna be like, “Oh, yeah, well, I know Mr. Smith who’s done it.” But I’ve never seen it. And so it’s an experiment. The same is true with the app I’m building. Again, I think one of the reasons why the app I wanna build doesn’t exist is because nobody thinks it’s a good idea. In fact, the people who are part of Coywolf might not think it’s a good idea that I’m building this. But dang it, I’m gonna build it anyways, because I want it.

There isn’t a contact relationship manager that exists today on the market that works the way I want it to work, that functions and has certain flexibilities that I want. So I’m gonna build my own. I’m starting with a card dev server, which is crazy. But that’s gonna store all my contact information. Nobody’s ever built a web app that leverages features of card dev, going beyond what we think of when we think of card dev; one that can actually be used for the status of contacts, to tag a contact, etc. So I wanna make that for myself and for others. But the other part of that is, I want something that works with my existing tools. I’m tired of having to have yet another web app that I have to pull in. I wanna be able to open up it on my Mac and have all that info there.

And I want it to integrate with my calendar. I want this really simple thing with just the fundamentals of contact relationship management. I don’t want something that automatically sends out crappy emails to people.

I want something that works the way I do outreach. And the way I do outreach is I go to the Twitter account, and I interact with them as a human being. I email them personally and write a message to them. But what would be nice would be this CRM over here that’s very simple, that does a few things that gets me to that point. That doesn’t exist and I’m gonna make it, and…

Woj: That’s cool. Well, let me know if you need a beta tester.

Jon: Absolutely.

Woj: We’re looking for a CRM at the moment. There is nothing that’s fantastic or phenomenal out there in the market currently.

Jon: I hate everything. I think Highrise is at the top of my list in terms of minimalist design and something that fits how I like to interact. But it has all this stuff I can’t get rid of in the interface. It has what they call “case”. Everything has to do with money and that’s not the type of outreach I wanna do. I want something that is easily fully customised for me and not overwhelming in regards to interface.

What’s in store for you for the next five years? And how are you going to achieve these goals?

Jon: Well, assuming I’m still alive… I might be hit by bus, or fall off an airplane. Wouldn’t it be weird if I fell out of an airplane, survived the fall but then got hit by a bus?

Woj: That would be intense.

Jon: o I have no clue is the first part of the answer. The place I’m at right now is I’m incredibly appreciative of my day job. I am 46 going on 47. And I’ve had many different types of jobs. And I know how hard it is to find a place where you enjoy the people you work with because you respect them and you like them. And you enjoy what you do. It’s gold if you can find it. I feel like that right now. I really can’t speak more highly about where I’m at, and what I do for my full-time job.

I just really enjoy what I do. I learn stuff all the time that’s new. I get to work on sites I’d never get to work on usually, with huge, crazy traffic. I work with super talented developers and editors and writers. So I have a great time there. Right now, I’m almost into year two, and I see myself continuing to be there for a while. But I also really wanna grow Coywolf too in my spare time. And I love writing. And I like building things. So it’s possible that within the next five years, Coywolf becomes big enough that that’s where I choose to spend more of my time. But I think a lot would have to change for me to wanna switch my current situation.

My hobby is doing the same thing I do at my job, as my hobby. It’s always been that way. Like, I love doing what I do. I love working here. And I love building sites. I love writing. I love doing all these things. And so, when I have my free time, and I’m not spending time with my family, it is extremely enjoyable for me to work on the Coywolf stuff.


Actually, it’s a very sane, rational decision for where I’m at in life right now. I live in the U.S. I need good health care for my family and my children. And the company I’m with is a kick-ass company that has great benefits. And I get a salary that makes me happy, happy enough. It’s not like what I had at Raven as an owner, but you know, it’s enough.

So I feel fairly compensated. I don’t hate getting up in the morning and doing my work. I don’t hate interacting with my colleagues. 90% of people are probably like, “I kind of hate getting up. I kind of hate working with most of the people I work with. And I don’t really love what I do.”

And things could change at any moment. But when you get in a place that’s good like that, I think that the best move is to be aware of it, and appreciate it, and hold on to it.

Woj: I think you hit the nail on the head. Appreciation is where it’s at. I think the community really appreciates you and your work and everything you’ve done over the years in the SEO space. So thanks a lot for your time. I really appreciate having a chat with you. Where can people find you online and connect with you to find out more or read some of your content?

Jon: So I mainly hang out at 4chan.

Woj: Excellent. What’s the handle?

Jon: I have no idea, man. I’ve never even used it.

Woj: Excellent.

If you enjoyed this interview, be sure to read part 1 (if you haven’t already) and follow Jon on Twitter @henshaw. Now, go ahead and check out some of our other interviews:

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