Brian: You're damn right, I am.

John: Yes. Brian is a serial entrepreneur based in Boulder, Colorado. He's the founder and CEO of Rainmaker Digital, the behind Copyblogger, Studio Press, Rainmaker FM, and the Rainmaker Platform. Brian, take a minute, fill in some gaps from that intro, and give us just a little glimpse into your personal life.

Brian: Wow, I'm not sure we want to go there, but most people know me as the guy who started Copyblogger, which we found was about this thing called Content Marketing – so, something I'd be doing since 1998.

John: Thanks Joe.

Brian: Yeah, exactly. Thanks Joe, for twisting my arm in adopting that terminology, but it's a $44 billion dollar industry now, so he may have been on to something.

John: Absolutely. Joe Paluzzi was actually just on the show last week – so, Friday edition. If you missed it go check out Joe Paluzzi's most recent episode. We really crush Content Marketing. Brian, why Boulder? Let's here some personal stuff.

Brian: Yeah. So, I spent about 40 years of my life in Texas, after being born in California. I lived in Austin, which I enjoyed. It's a town that's really grown and changed. And then, after the dot.com crash, things got really shaky in Austin for a while, so we had to move temporarily to Dallas, which I'm not the biggest fan of. So, two kids and ten years later, I'm like, “Why are we in Dallas?” We were spending summers in Colorado because of the heat. The older I get, the less I can tolerate the heat. So, finally we just said, “We love Colorado, so why don't we live here?” And, that's really the decision.

John: Yeah, and you were really tired of not paying state taxes, too.

Brian: Well, it's funny. You have to do the math because if you don't own property in Texas it's a great deal, but if you own a house, the property Taxes will almost equal the state income tax.

John: Wow.

Brian: So, I really kind of broke even on it.

John: Interesting.

Brian: And, they've got a great, big mountain range, which they don't have in Texas.

John: Right. Well, that's why I'm a renter, Fire Nation. Brian, there is a lot of stuff we're going to get into today, but first and foremost, Fire Nation – my audience, my listeners – are made of entrepreneurs; small business owners; people who are about to take the leap; who have just taken the leap, and are looking to build viable businesses from the ground up. How do you currently generate revenue with your business?

Brian: So, the easiest way to describe us is: We're in the tools and training business for online publishers and marketers. So, that mean software. The Rainmaker Platform is our SAS service that basically gives you all of the tools you need to build the right kind of website, and do the right kind of marketing automation, and all of that kind of good stuff. That's our newest and fastest growing thing. We're also in Wordpress Hosting, for the do-it-yourselfers out there. Obviously, Studio Press is the genesis design framework for Wordpress – and a whole bunch of pretty designs and themes that you can add to that.

Then we have training programs like Authority. Our newest thing is called Digital Commerce Institute, which is all about really what we do to make $12 million bucks a year, which is sell digital products and services.

John: Wow. One thing that I saw you do fairly recently was jump in a big way into the podcasting world. Can you talk about that a little bit?

Brian: It's all you, man. It's all you.

John: Oh, come on.

Brian: I cannot keep up with you. I won't even try, but I really enjoyed podcasting. And, here's an interesting story that I like to tell as a cautionary tale of not playing to your strengths, or conversely playing to you strengths. But, in 2005 – remember the old days of when podcasting really first started – before I started Copyblogger. I'm a writer more than I'm anything else, but I actually considered started a podcast in 2005 instead of Copyblogger. Now, how bad would that have gone?

John: Horribly.

Brian: I mean, ten years later, I would have made it.

John: Yeah. I will say that the evolution of podcasting is definitely different from that of a blog, and just websites in general. So, you took the right route, my friend. And, with podcasting, better late than never. You are on board. You are crushing it on a lot of different levels, and I'm seeing some really cool things. I'm taking notes, too. There's some really good stuff. Definitely check out what he has going on, Fire Nation.

Brian, I want to talk first and foremost about a moment in your journey. Now, you've had your ups; you've had your downs. You've had your Dallases, and you've had your Boulders. Share with Fire Nation what you consider your worst entrepreneurial moment to date. And, Brian, really take us there. Take us to that moment in time, and tell us that story.

Brian: That's a tough one because if you've been doing this for 17 years, you rack up some bad moments, I would imagine. Even though I would say that over all it's been good. I've started nine businesses. Eight of them have succeeded. So, that's not too bad. But, surprisingly, the one failure, which was the first one, is not my worst moment because I learned more from that. I became an entrepreneur because of that. So, I can't call that the worst moment.

I think the worst moment for me was in 2005. I was running two virtual real estate brokerages. It's an old world kind of business, but it was completely innovative. It was just websites. There was no brick and mortar. And, this was my first true, real entrepreneurial success, where I'm leveraging the talents of others, and trying to manage people, and had really innovative marketing, and all of this good stuff. But, I was a terrible manager. Have you ever read the book The E-Myth, by Michael Berber?

John: Oh, yeah.

Brian: Working in your business as a technician instead of on your business – that was me. I couldn't delegate. I didn't understand why people didn't see what I saw that was so obvious. They were always kind of getting hung up on things. It's such a common story, it's almost ridiculous. But, I don't know anyone who hasn't gone through this phase where you succeed yourself to death. And, I was really, really unhappy, and ended up getting out of those businesses. I tried to sell to my partners. It feel through. I really went into Copyblogger pretty much broke because of that.

But, I was just so fed up. I also had a near death experience from a snowboarding accident. So, after that I actually had brain surgery, and when I woke up I was fine. Everything was good. But, it's like my mind changed. It was, “I'm never doing anything that makes me unhappy again. I'm never doing anything where I'm not playing to my strengths, and I'm never doing anything just for money.” So, if I go in a different direction here, and I end up making less money, but I can support my family, and get by, and be happy, then that's good enough.

But, you know what happened? My worst moment lead to exponentially greater success. So, my advice for people is, “If it doesn't feel good, stop doing it.” Because the thing – the direction you need to go in may be the thing that really just launches your success to a whole new level.

John: It's kind of weird to say, but it is sad for some people that they're not going to have some kind of life-changing, you know, near death experience moment – because for so many people, Brian, that's what it takes for them to wake up.

Brian: It does for me. I had such a hard head that I had to slam it into the side of a mountain, I guess.

[Crosstalk]

Brian: But, it worked. Yeah. And, that's a big thing about the podcast you mentioned that I'm doing now. It's called Unemployable, and it's for similar people to your audience in that this is the greatest thing in the world. Even though it's hard. It's not always glamorous. We work 80 hours a week not to work 40 hours for someone else – what ever the case may be.

John: Right.

Brian: But, I'm in love with the entrepreneurial lifestyle. It's what gets you out of bed in the morning, and that's why I try to share these experiences with people because I don't want you to have to get knocked upside the head in order to see the truth.

John: Right. And, that's why I love starting EO Fire with my guest's worst entrepreneurial moment because sometimes that is the back-slap that my listeners need so they don't have to experience it themselves. They can experience it through this interview and say, “Hey, I don't want to be 80 years old, looking back on my life and saying, “Why didn't I do anything that I enjoy; that I was passionate about; that I was excited about; that I woke up saying, 'This is going to be a good day.'?” Why? So, I love that for all those reasons, Brian.

And, you really got into the E-Myth revisited, and I think that's a book, Fire Nation – if you haven't read that for a while – go back, pull that off the shelf, dust it off, and give it a look. It's so important to realize that just because –

Brian: It's still relevant.

John: It is still relevant today. Just because you love baking bread, don't run off and go make a bakery. That is a totally different lifestyle than actually baking bread. This is the type of thing that you need to realize and identify: Who are you in your business? And, adjust accordingly.

So, Brian, let's do a little bit of a shift here because you are a storyteller extraordinaire, and you've just given us a gem. Now I'm looking for an Ah-ha moment; an epiphany; a light bulb that went off in some point in your journey. You've had a ton of these moments, but just like the unemployable audience, you know – Fire Nation – you know us. We're looking for a story of one of these moments that you've had that you really just took and ran with that we can relate to. So, take us to a moment of one of these Ah-ha moments that you had, and tell us that story.

Brian: Yeah. And, this is what I call the Virtue of Cluelessness. Because, again, 17 years later people will look at what we've accomplished, and where we're at, and they won't realize where I started was probably worse off than everyone listening right now as far as understanding anything about business, or starting companies, or anything like that. So, let me take you back to 1998.

I graduated Law School in 1994. I knew in the third year of Law School that I didn't want to do it, and yet, of course I had students loans. I put myself through Law School, so I got a great job; big law firm; private office; assistant – you know – the whole life. I hated it. I hated it. But, I had bill to pay. So, but four years – 1994 to 1998. Coincidentally 1994 is the year that the commercial web really broke out with the browser making it easier for normal, non-technical people to experience the internet.

So, every night after an unhappy day of long hours of work, I'm staring at this boxy old Compact computer screen, and just saying, “This is amazing. You can reach people all over the world.” And, it's a very different time, obviously. Even in 1998 there was a lot of dot.com mania, but there weren't blogs that told you how to do everything, and there weren't courses, and podcasts, and conferences. There's almost too much now. But, compared to then there was nothing.

So, there were people who were trying various things, and you just kind of had to observe. And, sometimes you made friends with people, and you shared tips and stuff like that, but I had never taken a business class; never read a marketing book; but I was so fed up that in 1998 I quit to write on the internet. Now, try to explain that one to your mom. Even today that sounds crazy. But, that's what I was doing. People like Chris Perillo and others were publishing e-zines – basically content by email. This was before blogs caught on, and I was like, “I can do that.”

Every ex-attorney or current attorney thinks that they're going to write the next great American novel. I mean. We all think we can write. I had some talent for it, and got out there. I quit my job. I just figured it was one of those moments like, “If I have to end up bartending in Austin, then so be it. I'm not going to be miserable, right?” I've had a lot of those moments, you might have noticed.

John: Right.

Brian: So, I got out there, and I created e-zines, and people signed up for them, and I build audiences. All of this stuff we tell marketers they have to do now, I just wanted to do. I'm very transparent about the fact that my own aptitude; my own personality led me to do what we now call content marketing. So, I built audiences, and all of this stuff, and made no money. I think I made $4.32 from some Amazon ads in the year, because I didn't know what I was doing. And, my Ah-ha moment – Mr. Seth Godin, Permission Marketing in 1999 – a book I still recommend people read.

John: It's still relevant.

Brian: People talk about internet time, but all of the fundamentals are right there in that book. It's very simple, and email is still the thing. I know you're really working hard on building up the email presence in your company, and of course, that's smart. But, really what Seth said, and Seth off-line was a brilliant and hard-nosed direct marketing guy. And, that doesn't jive as well with his Buddha on the mountaintop personality that he has now. He's a very, very sharp guy. But, what he got was that the internet was a direct marketing medium, but not like junk mail, in that you don't buy a list of addresses based on demographics, or what ever the case may be, and then spew out a bunch of stuff, and hope it's profitable.

Online was different in that you needed permission. You needed someone to say, “Yes. I'm raising my hand. I want you to contact me.” And, of course, that makes all the difference in the world between unsolicited or interruption marketing – as he talked about – and someone who expects to hear from you. And, the real Ah-ha moment for me was, “Yes, you need something to sell other than advertising.” And, of course, in my mind, I was like, well, content makes money from advertising. And, 17 years later we see what a mess the world of online advertising is. The banner ad was one of the worst ideas ever.

John: Ever.

Brian: But, there's an upside. Podcast sponsorships are doing well. Why? Because there's an analogous thing that's always worked called Direct Response Radio Advertising. It's funny how what's old is new. But, I benefited by not understanding marketing at all, and therefore I had nothing to unlearn. So, the first marketing book I ever read was Permission Marketing, which is odd considering that many people kind of look to me to learn this stuff. But, at that point I then went back. I said, “Oh. Okay. So, this is form of Direct Marketing.” So, I went back and studied Copy Writing; Direct Marketing; Advertising dating back to the 1920's, except I understood the context of the new internet.

And, there are a lot more talented people who were really good in those fields off-line who struggled coming to the internet because they could not shake the way it had been done, and that's what I call the Virtue of Cluelessness. I had nothing to unlearn.

John: The phrase that you said that I really want to circle back on, and make sure that – Fire Nation – you absorb, “What we tell people they have to do now, I wanted to do.” What I loved about that Brian is that you wanted to be doing this stuff. You had passion, excitement. You were into it. And, Fire Nation, check your pulse. Are you doing stuff that you want to do, or are you doing stuff because you're being told you have to do it? If it's the latter – not good. You really want to be in that prior camp. You want to want to be doing that thing.

Brian: Yeah. And, that was the moment where I realized I thought I wanted to be a writer, and then eventually I realized that I was an entrepreneur who could write. And, that turned out to be a blessing, again, in this whole new world of media over marketing, or content and value before the sale. So, yeah, like I said, I admit wholeheartedly that I got lucky based on my own temperament. But, to a certain degree, I agree exactly with what you say. And, yet, for example, you do this incredible podcast. You are a content creator, and you started it just by being the consummate host. Now people, including me, look to you as an authority. And, you did it by showing up day after day, literally, day after day. I'm still amazed at you.

John: 1,164 days, including today.

Brian: But, what a great example is that, you know? The people out there saying, “Well, I'm not an expert; nobody knows me.” Guess what? When I started Copyblogger, I had not one relationship in the industry. No one knew me. It was just as deadly silent those first three months like it is for everyone.

John: Yeah.

Brian: You have to show up.

John: Crazy. Brian, what is your biggest weakness as an entrepreneur?

Brian: Historically, it's been delegation, and that goes back to my lowest moment back in 2002 to 2005. Then, I shifted to a model where I only did what I was good at, instead of trying to wear all of the hats, and do everything. I do strategy. I create content. I do marketing. Those are the things I'm really good at, and that has evolved as I became a CEO. Then, once we had an organization that's now 60 people, and I have a team of incredible content and marketing people who are literally like an extension of myself to where I don't have to do everything so hands-on.

And, yet, even though I narrowed what I did, I had trouble letting go of that aspect. All of our product websites – all of the copy was written by me, and still is. Is that a smart thing for a CEO to do? I don't know. But, I always do it because it helps me feel closer to the product; to the offer; to the audience; to our customer base. But, slowly, over the last couple of years, I let go more, and more, and more. And, it is a weakness because that feeling that you need control, and to be hands-on. I'm not really a micro-manager even; I'm just, “Look. Get out of the way. I'll do.” You have to let go of that to be an effective leader. It's been my top priority. I'm getting better. It's like a 12 Step program.

John: Well, the reality is, Brian, you can do it better that time, but it's the 100 times after that. If we had just taken the time to train, if we wanted to train, and then step back and say, “Okay. Now, you're off to the races. Now I'm not going to have to be there every single time. I can leverage my time. I can scale other parts of my business.” Speaking of that, what is the one thing that has you most fired about your business today?

Brian: Here's the quick story of how Rainmaker Digital came to be. Between 2007 and 2010, I launched four start-ups off of Copyblogger, and each one of them was with an individual partner. So, that was part of my plan, too. I'm good at this. I do audience marketing strategy content, and you do code, because I can't code. Or, you do design, or help me build this training course, or what ever the case may be. By the time we got to 2010, we wanted to do something bigger, except all of my partners had no economic incentive to speak to one another. I was the hub in the middle of these satellite companies, but there was no inner-connection.

So, we merged five companies together to form what was originally Copyblogger Media, and has now since been rebranded to Rainmaker Digital. And, the reason we did that was to build something bigger, and that is what is now known as The Rainmaker Platform. And, I'm completely excited about that. So, we soft-launched a pilot program in April of 2014. The official launch happened in September of 2014, and we were able to go from version 1.0 to 2.0 based on the feedback of our pilot group, which was pretty amazing.

So, it's about a year into it. It's not only our fastest product growing currently; it's our fastest growing ever. I feel really good about that. Can you imagine merging companies together; going on a mission; accumulating 60 employees when you swore you'd never have any again, and then crashing and burning? That would suck. So, I guess I'm just excited that it's working.

John: I'd have you back on EO Fire to talk about a new worst moment, I think, if that was the case. Now, Fire Nation, as you can tell, Brian is not going to stop dropping value bombs. So, the Lightening Round is coming. But, first, let's take a minute to thank our sponsors. Brian, are you prepared for the Lightening Round?

Brian: I'm as ready as I'm going to be, I guess.

John: What was holding you back from becoming an entrepreneur?

Brian: Honestly, the word did not even exist in my vocabulary when I was trying to get out of practicing law. And, it's weird because I translated myself in, “I want to be a writer, but I don't want to go to New York publishing. I don't want to go to Hollywood screenwriting. This internet thing allows me to do it without asking for permission.” Again, I think that comes back to the that unemployable thing. I had this fierce independent streak, and that is really what sent me on a journey that I didn't really even know where I was going. Does that sound odd?

But, again, like I said, when I realized I was an entrepreneur who could write as opposed to most writers, that was an epiphany to me, and it was really the beginning of this serial adventure that I've been on.

John: What is the best advice you've ever receive?

Brian: Stick to your guns. Stick to your convictions. Learn to say, “No,” so that you can selectively say, “Yes.” It's one of the hardest things in the world, but you know, as someone who had several – you know, obviously I launched a new start-up every year between 2007 and 2010 with a partner. Often those partners came to me and pitched me. What people don't realize is I said, “No,” 98 other times, for the three times I said, “Yes.”

John: What's a personal habit that contributes to your success?

Brian: Relentless thinking. I do give this advice to people all of the time because I think the stereotype or the image of the entrepreneur is you wake up in the morning, and it's go, go, go. Meeting; phone call; this; that; the other, and by the time you get to the end of the day it's a blur. You're not even sure what you got done. And, that's a problem. And, that's why people work their asses off, and don't achieve anything – because there are only so many things that are really, truly important, and the rest of the stuff will just eat your day.

So, at the beginning of each day I set what has to get done. This is the big thing. This is the thing that pushes everything forward. Do that first. And, then, trust me, the rest of the day will take care of itself.

John: Share an internet resource like Evernotes with Fire Nation.

Brian: Man, it is Evernote. I am not a big gadget or shiny – you know, I don't go chase the newest thing, and try this, and try that – because I find that by the time that I've figured out how to use it, I've just eaten all of the productivity gains I was going to get from it. It took me a while to adopt Evernote, but now that I've figured out how to make it work for me, as everything from to-do, to archiving interesting information, categorizing things pursuant to, “Okay, this is a podcast topic. This is something from my newsletter Further. This interesting. I need to share this with the team at Rainmaker Digital.” I don't know how I'd make it without it now.

I'm sorry I couldn't come up with something that wasn't your own example, but that is my go-to tool.

John: Brian, we talked about Permission Marketing and E-Myth, but if you could just recommend one book for our listeners, what would it be, and why?

Brian: It usually is Permission Marketing just because it is so foundationally important. I'm a voracious reader though, so then it becomes very difficult to then say, “Okay, what's the next most important book?” I think if you don't want to take Permission Marketing as my answer, I would just say become a reader to the extent that you can possibly fit it in. I know not everyone likes to read, and I think that's why a lot of people are into audio content. Audio books work, too. But, the more ideas you fit in your head – and, I'm not just talking about reading business books, or books about entrepreneurism, or what ever – read a book about bee keeping.

That may be an extreme example, but all of your best ideas will come at the intersection of something that seems completely unrelated, and then what you do day to day – your expertise. Henry Ford visited a meatpacking plant in Chicago and came up with the idea for the assembly line for cars, which was amazingly innovative, but not to the meatpacking guys. They'd been doing it for years. So, it seemingly has nothing to do with what you're doing. I'm a big advocate. Take time out. Watch movies. Read trashy novels. I don't care what it is, but you will get your best ideas from when you think you're screwing off.

John: Well, Fire Nation, Brian is right. I know that you love audio, so I did team up with Audible, and if you haven't already, you can get any amazing audiobook for free at eofirebook.com. Brian, this is the last question, but it's a doozey. Imagine you woke up tomorrow morning in a brand new world, identical to earth, but you knew no one. You still have all the experience and knowledge you currently have. Your food and shelter is taken care of, but all you have is a laptop and $500.00. What would you do in the next seven days?

Brian: I would basically do what I did in January of 2006: Build a site out of a domain that was aimed to educate a certain type of person, with a certain type of knowledge or benefits of knowledge, if you will. I'd start writing. I'd make sure I created a process by which it became – you know – everything I've learned about building an audience, which generally means building an email list – I would put that into practice on the site, and then $500.00 isn't a ton of money for advertising, so I might just have to do the hustle like I did back then, which is reach out to people who don't know you, and just keep plugging after it.

I don't think it would be much different, but the only thing that might hold me back is the fact that John Lee Dumas put me on this weird parallel planet earth, and I lost everything and had to start over. Thanks dude.

John: No, problem. And, hey, nothing wrong with doing the hustle. Fire Nation. Brian, good stuff. Hey, Fire Nation, you're the average of the five people that you spend the most time with, and you have been hanging out with BC, and JLD today. So, make sure you keep up the heat. And, Brian, let's end on fire, so share a parting piece of guidance – the best way that we can connect with you, and then we'll say good-bye.

Brian: Yeah, I have to tell you. I've gone through a long journey myself, and part of it was just desperately hating my job, and I know a lot of you may feel that way. It's probably smarter to start something on the side than to just quit. If you're like me, and you love pressure, then who am I to tell you, “No.”? I remember when I went from that first kind of freelance, solo law practice, which was my first success to my first business that had nothing to do with law, which was real estate. And, I chose it because it was lucrative, because what I knew about online marketing made it like shooting fish in a barrel, and I had something to prove.

I had to prove that I could start a business that was completely different from what I had been trained in; where I came from, right? It's one of those personal quest things. Sometimes we have to do that as people, and as entrepreneurs. But, if I could have done it over, I would have stuck to my guns and followed more of my passion at that point – because I had no passion for real estate. If you're doing something just for money, or because you want to prove something to you dad, or what ever the case may be, you're being externally driven instead of internally driven.

And I'm telling you, the thing that lasts is intrinsic or internal motivation. The stuff you do; the stuff you get up in the morning to do just to do it – if you can get that way as an entrepreneur – and, most later-stage entrepreneurs are this way – it's never about the money anymore. They money is just a way to keep score. So, that's my best advice. Do it from the heart. I'm not saying that every little hobby or passion you have is going to turn into a lucrative business, but if you work at it you'll find the intersection between what excites you, and what pays the bills.

John: And, what's the best way to connect with you?

Brian: Well, we do have this new podcast. You can go over to unemployable.com, and sign up over there, or you can find it on iTunes. But, if you're really just kind of getting started – and maybe you listened to the show with Joe Paluzzi about Content Marketing – in addition to his site, you can go to Copyblogger. We have an entire library of free ebooks that you can register for, and get started – you know, the foundational learning. If you are a listener, and I suspect you are, you can head over to our podcast network, which is called Rainmaker.fm.

So, that's a good place to get started. Those are our three informational sources where it doesn't matter if you ever buy anything. All of it is there for your taking.

John: Now, unemployable.com – how long ago did you buy that domain.

Brian: I bought it in the spring.

John: What?

Brian: So, I came up with the idea of the show last December when we were planning out the podcast network, and all I could get was unemployable.fm, which I figured, “That's fine.” But, then I saw someone was sitting on unemployable.com, so you know, I sent out the feeler; pretended like I was completely clueless, and got it for less than you might think. I think because I'm using the term ironically, and the person who owned it was probably holding it literally, it wouldn't be as profitable site as perhaps it might be with me.

John: That's awesome. Love it. Well, Fire Nation, head over to eofire.com. Type 'Brian' in the search bar. His show's page will pop up with everything that we've been talking about today, with links to all of the stuff. You definitely want to check out his podcast at unemployable.com. Give it a listen. And, Brian, thank you brother, for sharing your journey with Fire Nation today. For that, we salute you, and we'll catch you on the flip side.

Brian: Thanks, man. I appreciate it.