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Business Leadership (Part 1) with Guest, Ryan Deiss [Podcast]

Episode 70: In part 1 of this very special interview, Michael and Kathryn chat with Ryan Deiss, founder and CEO of DigitalMarketer.com. Discover how Ryan maintains a healthy balance of work, life, family, and entrepreneurship, all while growing a profitable business and maintaining a positive company culture.

Ryan Deiss speaking

In This Episode You Will...

  • Discover the origin of Ryan's company, Digital Marketer.
  • Find out how Provision plays a key role in how Ryan grows his business.
  • Learn why complacency can be a success killer.
  • Find out what all healthy company cultures have in common.
"If you don't try anything new, you are rarely going to look foolish... but you also aren't going to get better, you aren't going to improve. – Ryan Deiss

Take the Leadership Blindspot Quiz

References:

  1. Traffic & Conversion Summit
  2. Digital Marketer

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Michael:        Hello and welcome to the HaBO Village Podcast. I'm Michael Redman-


Kathryn:
      And I'm Kathryn Redman-


Michael:
      And this is a podcast all about helping business leaders like you build passion and provision companies with a holistic perspective so that you have more profit and more joy and ultimately you get to create a greater contribution. Today we have Ryan Deiss who we're pretty excited about having. Ryan is a friend of ours, but Ryan is also the owner, Co-Founder of Digital Marketer, a large marketing company that does training and certifications for digital marketers and the digital marketing world. And he has done an amazing amount of stuff out there. His list is super long and I'm not going to read it all.


Kathryn:
      He's super important.


Michael:
      And the cool thing we like about Ryan, on top of his sense of humor and that I feel tall around him and I don't feel tall around anybody, is that Ryan is really, really famous in a really narrow niche and none of you will know who Ryan is except for the fact that we talk about him periodically and we talk about the value journey. And for those of you that listen and are familiar with that, Ryan's the one that created that. So Ryan, welcome. Thank you for showing up.


Ryan: 
           Yes, thank you for telling everybody that I'm short. I want to make sure that in a media such as audio, where I can literally be any height, I want everybody to picture in their mind the reality of it. So thank you for that. I don't want to get big headed.


Michael:
      Well, you know, that's very important because I am vertically challenged amongst most of my friends. So hey, really brief, so that the folks that listen to our podcast, I mean what you've got here is a bunch of folks that are small business owners. They're somewhere between five, usually, employees to 50 and we've got some folks that are up to 100, 150, so they're not huge companies. These folks are folks that really want to grow their companies, but they want to enjoy it. They want to make sure that it impacts the rest of their life in a healthy way. And then that the things that are important outside of the grind at work and running their companies is healthy and whole. And one of the reasons I like spending time with you and I wanted to interview you is because that has been a trend that I've seen in your life where your marriage, your kids, and everything is a priority to you. So as we talk about that, that's the folks you're talking to today.


Ryan:
             Great. Yeah, those are my peoples. Love it.


Michael:
      So when did you start Digital Marketer?


Ryan:
           Digital Marketer, gosh, it's a complicated... So Digital Marketer, the company itself, has been around for seven years, but I've been... Really Digital Marketer was started out of an event that we did called Traffic and Conversion Summit, which I know you've been to. So Traffic and Conversion Summit, largest digital marketing conference in North America. That was actually started about 10 years ago. But even prior to that, I was creating trainings on how to do different aspects of marketing. Anytime I would learn something new, I would do a training on it. And that was... And I would sell it out offered. It both forced me to learn and to document stuff. It created the seed capital to launch some other ventures. So as you know, we're in a lot of businesses in addition to Digital Marketer. I've majority minority in some cases, interest ownership and a number of other businesses and a number of different verticals.


Ryan:
           And that's what I've always done. I've always started companies and I've always taught what I did. And so if you were to ask the AG in Texas, like when was it started? It was seven years ago, but really I would say Digital Marketers kind of always been around. I've always taught. I've always shared. I've always believed in once you learn something, share that knowledge with other people. But the formation of the company really started on the third day of the third Traffic and Conversion Summit. I remember looking out in a room full of about 800 people going, "This might be a thing. I should probably treat this like a business." So it's like I bet a lot of the listeners, you know, and it kind of-


Michael:
      Yeah, I was just thinking that.


Ryan:
             You lined up in a business. It's like an accidental entrepreneur, right?


Michael:
      Yeah, you don't actually... A lot of people don't plan to start a company. They're doing something and it's like, "Maybe this has got some legs, let's try this." And then all of a sudden some things happen and you take a left turn that you didn't know you were going to take.


Ryan:
             Right. And I think that was exactly what happened here. And that's why I can't pinpoint, it's not like, "Oh, I'm in my dorm room with my Stanford and my roommate has figured out in this thing and we went and got funding and got into Ycombinator." And like, no, it wasn't any of that. It's just you wake up and you're like, "I guess I'm in this business now."


Michael:
      Well and for those of you listening, Traffic and Conversion is an annual conference that has been held in San Diego and this next year, Digital Marketers is branching out around the world with this conference, which is really exciting.


Michael:
      And it probably is important to say that we've been involved with Digital Marketer in their partner program for several years now. And we-


Kathryn:
      Yeah, we were trying to pinpoint exactly how long. Do you remember when you started the partner program? Because we were beta guinea pigs.


Ryan:
              Yeah, I mean and the partner program went through a couple of different iterations similarly. And I think hopefully, we're among friends. So people will appreciate the fact that sometimes you try something and it doesn't quite work, so you have to go and try something else. So when... I believe you all joined three or four years ago, and that was actually on the second iteration, the second beta. So you were actually the second round of guinea pigs. The first round of guinea pigs, we just killed all of them. They didn't make it.


Ryan:
             And so, no, they're actually some of our most ardent supporters as well. But yeah. So, I mean that was, when we kind of went back and made it more about as you said, the customer value journey less about the email marketing machine. Part of that is all centered around email marketing. We made it more holistic, more about marketing as a whole and that was when you all got in.


Michael:
      Yeah. Well, and we were pre-markets coming into the company.


Ryan:
             Yeah. So that was definitely-


Michael:
      He was still [crosstalk 00:05:45].


Ryan:
             Yeah, so four years ago then. Because he's been around for three.


Michael:
      So what I was trying to say is, Traffic and Conversion now, the last one we had what about 8,000 there?


Ryan:
             Yeah about 8,000 if you count all the sponsors and things like that. It was just under 8,000. It was around 7,400.


Michael:
      So imagine being in San Diego at one of the conference halls. We've got 8,000 people-ish. And it's a big event that lasts for three days. It is a great time. There's a lot of speakers, a lot of things that are really fun. And one of the things you shared this last year, because you were talking about it a few minutes ago, was Traffic and Conversion. When it started early, you shared a story from the stage about how glad you were you kept with it because you didn't enjoy being on the stage and you didn't really want to do that. Perry kind of pushed you into it the way you made it sound.


Ryan:
             Yeah, no I totally-


Michael:
      Perry being a business partner of Ryan's.


Ryan:
             Yeah. No I don't like... So in my experience, I've worked with a number of different entrepreneurs. I've known a lot of entrepreneurs. And there are some entrepreneurs who get into business because they really want to be a celebrity. And so they start their own company in part so that they can run a company or they... Whether it's a celebrity amongst their group, like they're empire builders and they want to have a team who is out there. They want to deliver these amazing speeches.


Ryan:
            And there's other people who they start a business out of their own ideas. So maybe it starts as a consultant and then they get into the guru type of space. I didn't want any of that. I just wanted the money. I just wanted to make enough money to provide a living for myself and to provide a great lifestyle for my family. So for me, it was always business was a means to an end. And that's what I can appreciate what you're doing here when you're talking about approaching business more holistically as an aspect of your life. I've known a lot of people who they define themselves, their identity is really centered around the business that they founded. I think that can be very, very dangerous. It also for me, just isn't why I wanted, because I don't enjoy being out there in front.


Ryan:
           I can fake extroversion. I am willing to get out, yeah, and speak in front of thousands of people. The largest group I spoke in front of was about 35,000 people. I will do it and I think that's another thing that's important. I will do stuff because I need to do it. I'll do it because it's the right thing to do for the company. Even if I don't want to. And there's a lot of people that are like, "Oh, you need to build a business that... That way when you start a business, you don't have to work for anybody else ever again. You'll just have the life that you want. That's not how it works at all.


Kathryn:
      Not at all.


Ryan:
             We just have to do everything. Yes. I'm glad that I stuck with it because I think had I been unwilling to do that, we wouldn't have grown. I think there's a lot of people who don't do the things that they should do because they're unwilling to do it and I was always willing to do the hard work.


Michael:
      Okay, so let's talk about that for a second. Leadership development. As leaders, it's been said that we go through, what is it, 10 to 12 transitions in our adult lifetime. So those transitions are places where we're growing. What got me here, won't get me there. So I've got to go through those phases and a lot of leaders don't actually end well because they don't make the transitions. When you made that comment about having to learn to, for the sake of the company, go on stage and do those types of things, you must have at some point went, "I don't want to do this," and been tempted to go, "Screw it. I want to turn around and go the other way." Because you have a determination, you're going to do it, but how did you push through that


Ryan:
            Fear. If I'm being totally honest, I was very, very, very afraid of continuing to do the same thing. I think one things that drives me is this constant fear that everything that I'm doing is just all of a sudden going to stop working. And I know it's fairly irrational, but I always feel like if I stay in one place for too long, if I don't grow, if we don't get better, if I don't improve, then I'm going to lose and somebody else is going to come along. And look, business isn't that binary? I know that. But what I also know is if you stop growing, if you lose that drive, if you lose that hunger, if you lose that paranoia, and somebody with that drive, with that hunger, with that paranoia is going to come along and they're going to do a better job than you serving the customer. And you're going to lose because you've gotten complacent.


Ryan:
           Complacency, I think next to running out of cash. There's a lot of businesses that fail because they just don't figure it out in time. They just don't. They don't quite get the messaging and the product and the positioning quite right before they run out of cash. That's the thing. As long as you've got cash, as long as you have fuel, you can keep trying and trying and trying and trying. Businesses fail, the number one reason is they run out of cash before they figure it out. Lots of people are successful in business because they worked the first time and other people, it took a lot of tries, took a lot of at bats and then finally it worked. That's the biggest killer. But I think once you have a successful business, the second biggest killer, and the biggest killer of successful businesses, is complacency.


Ryan:
           So for me, and I think complacency, a lot of people are driven by mastery. A lot of people are driven by, again, just a machiavellian pursuit of, "I just want to destroy, destroy, destroy, and win, win, win." I'm not either of those things. I think I'm primarily motivated by paranoia. I don't want somebody to come up from behind and take me down. So that's why I do the things I don't want to do.


Kathryn:
      So for you-


Michael:
      That's good.


Kathryn:
      It seems like I heard you say doing Traffic and Conversion again and again and again, were you feeling like somehow that was going to put you in a rut that that... You didn't want to do the same thing over and over again? Is that part of what you struggled with?


Ryan:
           I never want to do the same thing over and over again. And a lot of times that's foolish and a lot of what that comes down to actually is just getting bored.


Ryan:
           So I will get bored with things that are working. And I think this is another aspect of entrepreneurs. We all suffer from some degree of entrepreneurial ADHD. I was bit bopping off to the next bright shiny object. And when really what you need to do is you need to double down on that thing that's working. So the desire to keep trying something new again, oftentimes, and with Traffic and Conversions Summit, we've changed up the format, we've grown, but we've really tried to keep the promise the same. We've tried to keep the deliverables the same. We've shifted a little bit as the market has shifted. So early on, Traffic and Conversion Summit primarily served founders, entrepreneurs. They were the ones who were given this whole crazy internet thing a try.


Ryan:
           You think about 10 years ago. 10 years ago, Facebook wasn't really even a thing 10 years ago. The iPhone, it was there, but it wasn't this idea of mobile. We didn't have that. You basically kind of had Google adwords. So 10 years ago, digital marketing was so new that most of your bigger marketers, they were still... They hadn't really jumped into this yet. It was the people like me, the people like you, we had to use this. It was the best media for us. Other ones were too expensive. Too entrenched. So early on, that was who we served. What we found as the market changed is that now we have professional marketers coming out. We have agencies that are coming out to learn. We have companies sending their marketing teams.


Ryan:
           And I remember it was about four or five years ago, I stood on the stage at Traffic and Conversion Summit, I said, "Raise your hand if you're a business owner." Tons of hands went up. I said, "Great. My hope is that next year, none of you are in this room. My hope is that next year, you send your people. Now I hope you come, I hope you buy a ticket, but I hope you sit at the bar. I hope that you're, just during networking, not just sitting the bar getting drunk." I guess you can do that. No, I was like, "I hope you're here networking and talking, and having a good time, but you need to start sending your people." So we began, at that point, you know we changed up that from a single track event to a multi-track event because we realized that different people were coming and we need to allow them to choose their own adventures. So much of the change was driven by changes in the marketplace and that desire to want to serve that audience. More so than that... The change wasn't driven as much out of fear.


Ryan:
                     I'll change just because I'm bored with it. I really have to hold that back.


Kathryn:
      Yeah, makes sense.


Michael:
      So I think it's important just to note for our listeners, that as much as we're focusing in this conversation that we have been talking about T&C, T&C has happened once a year and that is not the bread and butter day to day work that DM does. DM does regular trainings, courses online, and now has, in this last year, year and a half, has a great studio classroom that they're doing regular workshops. Monthly things that you can become part of their membership and anything else.


Kathryn:
      Where I will be on Friday hanging out with you all day, Ryan.


Ryan:
           I know, it's going to be fun.


Michael:
      It's going to be so fun.


Kathryn:
      It's going to be great.


Michael:
      So T&C is really, for me, as I look at it, it seems like a barometer of how well the rest of the company has gone and how it's kept you busy. Now I want to shift a little bit here and pivot because as you've become quite well known and quite famous within the marketing community, I love the comment we had at a conference, we were at HubSpot two years ago, three years ago, having lunch. And one of the things you said you loved is you could walk out in the crowds and nobody knew who you were. So we were all sitting out there by the quad, by the trucks, and the four of us were having lunch, and you weren't being bugged.


Kathryn:
      Yeah, that was a good moment.


Michael:
      But in other places, you get mobbed, and there's this idea of you being really successful and you have a very busy business. It's obvious, we said before, you have multiple businesses. You're super busy. How do you maintain balance with your family, your marriage, your kids? Because you're really engaged with your kids and you're really engaged with your wife. What does that look like?


Ryan:
           I guess coming back to what you said about the whole being famous to pickup thing. That's... The internet is what has allowed for that. It is now possible to be incredibly famous to an incredibly tiny sliver of humanity. And that's really cool because it allows for a lot of people to make an income and to make an impact in ways that simply weren't possible before.


Michael:
      Well, and let me interrupt. The reason I bring this up, and because your head has not gotten it overinflated. You don't have big head syndrome from my perspective. As somebody who knows you and spends time with you. And that's one of the things that I think has been pretty amazing is it hasn't gone to your head and you've been able to keep balance in your life. So I just wanted to say that because that's my perspective of you.


Ryan:          
Yeah. Well thank you. I mean, I wouldn't want to be known as an arrogant prick. So it's good to know that that's not my brand. I will tell you, there's a couple of things that help out with that. One is I have a wonderful wife who loves me very much and calls me on my BS. So there are times when I might think that I am getting pretty cool and she'll remind me that like, "Hey, you're still that same person. I know who you are." And I've got four kids and they don't care. I've still gotta be dad to them. So I think they keep me grounded for sure. And also, we're always trying new stuff. And anytime you try something new, I don't care how many successes you've had in the past, you would think that you would bring all of this success with you to the next round and you just don't. Like every time you try something new, it's hard over in the same way, it's hard.


Ryan:
           And you find out that you make the same mistakes that you made before and areas that you should've learned, you just didn't. Stuff that you thought would work that was new, your instincts were wrong. So I'm also just continually humbled from a business perspective. So I think it would be very, very, very easy to get delusional and to be become very narcissistic. And I've seen this with a lot of people that I know. If you surround yourself with sycophants and you don't do anything new. So if you surround yourself with people who they're incentivized to tell you how great you are and to reinforce your general greatness and awesomeness, then you can get very, very delusional. You're also not going to get better. You're not going to improve. Also, if you don't try anything new, then you're rarely going to look foolish.


Ryan:
           But again, you're also not going to get better. You're not going to improve. So these people wind up in an effort to never look foolish in an effort to play the status game. What they wind up doing is actually locking in their own demise. Because if you don't have people around you making you better, if you're not constantly trying something new, then every day you become a little bit less relevant.


Kathryn:
      Yeah. I love that concept of people around you, keeping you humble. Because that's a really powerful statement. I mean, we just have to be reminded that at the end of the day, we're just who we are. And the press is great, but it's not the definition of who we are. It never is.


Michael:
      Yeah. Well, and having your business partner as your wife, that keeps you humble at some level.


Ryan: 
         Yeah, well I saw that in the intro. She was already giving you hell fumbling a word or two.


Michael:
      When we're live on stage, it's even worse.


Ryan:
           Yeah. Oh, I'm sure. You either are playing... People are either playing the status game or they're playing the freedom game. And I've always been more interested in the freedom game.


Michael:
      Elaborate a little bit more on that.


Ryan:
           I mean status, you want to be known as the person who is on top. You think about politics. And the downside to the status game is it is binary in that there are winners and there are losers. So if I'm playing a status game, then to win, I have to be higher than you. If I'm playing a freedom game and what I really want is autonomy, but actually I want to be the dumbest person in the room, I want to be the least important person in the room. Now you need to structure it such that in spite of all of those things, you still get the money.


Ryan: 
         You still own the asset. But that's what building a great company is all about. That's what building a lasting company and a great team is all about. Is eventually, over time, if you can convince enough people who are smarter than you, not overall, but smarter than you in a couple of areas, you get a team of these people who all independently are better than you at specific things, then guess what? Why do you need to make a decision anymore? Now you've just bought yourself freedom on autonomy. It also means that you've got to share the glory, which from a status perspective, oh that might sting a little bit. I think I'm helped in this regard in that I am a shyer introvert.


Michael:
      Yeah. Well, okay, so that's a great pivot towards building a culture. How many people roughly do you think you have working in the office there now?


Ryan: 
         So the digital marketing office I'm in right now, it's just under 60. Total company wide across all of ours, it's a couple hundred.


Michael:
      Okay, so when you're talking about creating culture and managing that, because that doesn't manage itself. It doesn't happen overnight and you can create a toxic culture or you can create a great culture. What are some of the top couple of things that you would recommend to folks as they're growing from those smaller, less than 20, less than 12 people through into the next couple of phases of managing that culture and making sure that you're staying on top of that, that it doesn't go sour.


Ryan:
           Yeah, so you can think about what culture is. Culture, at the end of the day, is shared beliefs. It's shared values and it's also shared narrative. It's shared stories. So that's what defines a culture. And cultures exist throughout the world, but they all share those same characteristics.


Ryan:
           You can't have shared leaps without generally... You can't have a culture without everybody generally agreeing on how old a universe works. If we fundamentally disagree with how the universe works and our place in it, we're probably not going to bond particularly well. And you see like microcosms of this at sporting events. So you go out to a sporting event and then there's... If you're rooting for the same team, the person sitting next to you can be a total stranger. But in that moment, you both believe in the same thing to be fundamentally true. And that's that your team should win and the other team should lose. And you're behaving the same way. You're cheering at the same time. You're singing the same songs. And doing the same stuff. You're telling stories about, "Oh do you remember two years ago when this happened? And oh that guy that was almost as good as like 10 years..."


Ryan:
           So what do you have in that moment? You have shared values. You have shared beliefs. You have this shared narrative. And now all of a sudden, you could be best friends of this person and you don't even know what their name is. So I think at a company level, first of all, you do have to decide what is it that we believe to be true? What is it fundamentally that we believe to be true? And what I heard at the start of, even this show, you made it very clear at the outset what you believe to be true about business, the way that business should work. It should be more holistic. It should be something that's impactful. I heard that. And as long as your message is shared regularly, then you can begin to align.


Ryan:
             That's correct, right?


Michael:
      Yeah, no you hit it. No.


Kathryn:
      You're good.


Michael:
      You're making me feel good because you're actually getting the message we're communicating.


Ryan:
            Yeah, no, but that's it, right? That comes back around to the last part. But first of all, you have to have it. You've got to believe in something. And I know for me at Digital Marketer, people come up to me like, "So what's our mission? What are we trying to do?" It's like, "Man, it's just to make payroll." And that's what I wanted to say.


Kathryn:
      Amen brother.


Ryan:
             And that's what I've wanted to say. And that's fine. You get into Maslow's hierarchy of needs and at some point it's just like, "I need to eat food and then we'll worry about all the other stuff." But right now I'm starving to death. And so there's an aspect of that. In the beginning, it's the travel mode, but if you want to grow, if you want to build a culture, assuming... Until you're actually running a company, it's probably premature to think about culture. You're not necessarily thinking about... If you're, I guess trudging out into the wild west, you're just trying to not die. You're not thinking like, "Oh, let's come up with a system of government." It's like, "No, we're leaving tomorrow. If we stick here too long, somebody's going to shoot us. So we got to go." And that's how the early days in business are. But once you've got that foundation there, you start thinking about consciously saying, "Why did I do this?" And there was going to be something that triggered it.


Ryan:
           But hopefully it was more than, "I just wanted to personally get rich." Because I can tell you if that's your reason and you don't find a greater one, not only are you going to have a very difficult time attracting people to your organization. If you do, they're going to eventually leave because what they see is that you're all about benefiting yourself and not them, and there's going to be misalignment at some point. But you're also going to get bored. You're also going to become demotivated. So you've got to figure that out. What do we fundamentally believe to be true about the universe and our place? That's one of the first culture questions you've got to answer.


Kathryn:
      So we want to thank you for joining us today. We're going to cut this interview off because there's just a lot that was shared and we value your time. So we want to make sure that we don't go too long. So we're going to air the second part of this interview next week so we hope you'll join us. It's been so much fun talking to Ryan and he's got a lot of great things to say. And continue to add, and so tune in next week for the rest of the story.