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Business Leadership (Part 2) with Guest, Ryan Deiss [Podcast]

In part 2 of this very special interview, Michael and Kathryn talk with Ryan Deiss, founder and CEO of DigitalMarketer.com, about his experience with company culture, leadership development, and business growth. You'll also get to learn some quirky and fun facts about Ryan (like his favorite and least favorite sound).

Ryan Deiss giving presentation

In This Episode You Will...

  • Discover why celebrating core values can help maintain a healthy company culture.

  • Find out how Ryan decided to change his company's mission.

  • Learn how personal growth can affect company growth.

  • Get to know Ryan better through 10 fun and quirky questions.

"Every quarter, you need to fire a significant aspect of yourself.... Because when you are growing a company the biggest inhibitor, besides the market, is the leader." – Ryan Deiss

Take the Leadership Blindspot Quiz

References:

  1. Molly Pittman
  2. Patrick Lencioni
  3. Roy Williams
  4. Universal Studios

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Michael:
             Hi there, and welcome to the HaBO Village Podcast. I'm Michael Redman.


Kathryn:
             I'm Kathryn Redman.


Michael:
             And this podcast is dedicated to building Passion and Provision leaders and building Passionate and Provision companies that are full of more profit, and more joy, and come at it from a holistic perspective. Thank you for joining us today.


Michael:
             We're going to go into part two of an interview we did with Ryan Deiss. Ryan is CEO and co-founder of Digital Marketer.


Kathryn:
             And, if you didn't listen to last weeks, you should probably catch that one first, and then you'll get the whole story.


Michael:
             Because that's part one.


Kathryn:
             Because that's part one, and-


Michael:
             Or you're going to be just jumping into the middle of a conversation. So, without further ado, here is part two of our interview with Ryan Deiss.


Michael:
             Do you remember the transition point you went from I just want money? Because we were joking earlier about that to, I've got to make that decision and it's got to be more. So, I've got to come up with a story for our team? Do you remember that?


Ryan:
                 Absolutely. I mean, I remember Molly Pittman who she's now gone off and is doing her own thing and doing great work. But this was when... she started with us as an intern and, at this point she was, I believe, the director of marketing. So, she ascended pretty quickly in the company, which we were a small company and that's-


Michael:
             That happens.


Ryan:
                  It's easier to ascend in a smaller company. But doing a great job and also asking questions like, why are we doing this? What is our mission? Like she was the one that came and asked me that. And I knew, saying like well, we're doing this so that I can eat food and you can too. And, to do that, we need money. I knew that wasn't a good answer. Right?


Ryan:
                  And so, I said to her then, I said, look, I don't actually have a great answer for you. So, give me some time to think about it. And I thought, and I thought, and I couldn't. It's like, I can't come up with anything that doesn't sound cheesy or hokey.


Michael:
             Mm-hmm (affirmative).


Ryan:
                 And I remember getting an email from Graham English, who was one of our customers and a big kind of advocate of Digital marketer, the type of person who would actually invest in a training, and then go and do it and get results. So, yay. He sent me an email with a screenshot and he said, hey, I just wanted to thank you. This year, so far, my business has doubled, not once, but twice over last year. And it had screenshots. And I said, that's it. That's what we do. We help businesses double so that they can achieve whatever it is that they want to do with their life. We believe that if we can double the size of ten thousand businesses, that we will shift whole world economies, right? So, this is a big deal and it's good, meaningful work.


Ryan:
                 And when I saw that, it's like, help double my business. That's a big thing, and it got me emotionally invested. I felt good about it. So, when I shared that with the team, I saw it with them as well. So, that was kind of the process. I think asking yourself, we're all here, let's fast forward five years from today, right? And we're going to clink glasses because we're celebrating a major win. What is that thing that, if we invested five years, in the next five years, what's the thing, if we were celebrating, we can look back and go, yeah, yeah. That was worth it. And if it's just, oh now I've got a Lamborghini, you're a pretty shallow person.


Michael:
             But if you have a Tesla, you're not shallow at all.


Ryan:
                 Well, it's a great car. I do think that's the first thing. I think that's critical for companies. And then you get into values, right? Deciding like what do we believe? How do we behave here? And so, you've got to really get clear on that. Patrick Lencioni has got some phenomenal stuff on-


Michael:
             Right.


Kathryn:
             Yes he has.


Ryan:
                 Coming up with values. And, I mean, he's got his book, The Five Dysfunctions of a Team, which is great. The advantage goes into that. So, I'm not going to teach that whole process. But basically, you got to think, what are those core values that really define you as a company?


Michael:
             Totally.


Ryan:
                 And then, you also have to ask yourself, which of these values that define us do we actually want to keep around? So, one of the things, one of the values that we had, an unintentional value that we had at Digital Marketer, it was bunch of young guys, certainly younger men, we are all friends, we were very jokey with one another in the way that a lot of times young guys will joke with one other. Ragging on each other, giving each other a hard time. Not this inappropriate locker room kind of talk, but just we generally showed our affection for one another by making fun of the people. And that's not that uncommon with guys.


Kathryn:
             Right.


Ryan:
                 It's juvenile, it's immature. I'll admit it. But we found in the beginning our culture was like, yeah. That's what we do. Like we're going to rag on you. Like, if you mess up, we're going to point it out. We're going to celebrate failure.


Michael:
             Yeah.


Ryan:
                 And what we found though was that, as we began hiring more people that we didn't know, in particular as we began hiring more women, we realized that's probably inappropriate. Like I probably shouldn't rag on a female that I don't know that well or a male that I don't know that well in the same way that I'd rag on Richard Tinder, who I've known for a long time, right? And we're friends outside of work. Like that's just not appropriate.


Kathryn:
             Right.


Ryan:
                 So, what we wound up doing was continue to rag on the guys but not ragging on the girls. And what this created was, was this sort of bro culture. And the only way that you could actually get acknowledged as a female in this organization was if you acted like one of the guys. This is obviously a problem.


Kathryn:
             Yeah.


Ryan:
                   Right? Now, this was a value that we really liked the fact that we had this fun and kind of silly and immature type culture. What we found is that we can't carry that value with us to the next level. That value is going to hold us back.


Kathryn:
             Yep.


Ryan:
                   So, we need to replace this. This is something that's there, but you know what? We need to start acting like professionals a little bit. That doesn't mean we can't have fun, it's a balance. But we just need to start acting like professionals.


Michael:
             No, I like this. This is good.


Kathryn:
             That's really good, Ryan.


Ryan:
                   And it was hard, but I'll tell you, it was hard because we felt like we were losing a bit of ourselves. And we found it's like, you can still have a good time without excluding others from your good time. So, that was the whole thing. If it's something I would say in a lighthearted manner to somebody else, to somebody I don't know as well, then it's appropriate, then we're being professional, we're being lighthearted.


Ryan:
                   So, we have a very, very strong culture. Our culture is very self-deprecating. Like, if somebody messes up, they're going to be like, oh, I really kind of botched that. And that's an aspect of our culture, right? Do we celebrate failures? Yeah, we will because that's where the learnings happen. But one of the things we needed to add as a core value was celebrate the wins.


Kathryn:
             Yeah.


Ryan:
                   Because we need to counter balance this thing by adding more praise into this, because we are naturally critical. We are naturally sarcastic. That's not going to scale well. We have to balance that.


Ryan:
                   So, looking at your values and then saying, okay, this is who we are, but is it who we want to be? Is it who we need to be to go to that next level?


Michael:
             Yeah.


Ryan:
                   And then, finally it gets into the narrative, right? What are the stories that you tell? What's your origin story? How do you share that and communicate? Communicate to the point where you know you've almost communicated enough when you start to tell a story, you start to talk about your values, you start to talk about your mission, and you start to see the eye rolls.


Kathryn:
             Yeah.


Michael:
             Yeah.


Ryan:
                   They're like, oh, we've heard this before. When people are making fun of you for how often you talk about it, you've almost, almost communicated it enough.


Kathryn:
             And how hard is that for an entrepreneur who gets bored?


Ryan:
                   It's very, very difficult.


Kathryn:
             Very difficult.


Ryan:
                   Very difficult. Incredibly difficult. Because you do get bored with saying the same thing again. It gets repetitive, but you have to.


Kathryn:
             But you have to, yeah.


Ryan:
                   And we've found that, if we don't, that it goes away. And so, you need to teach it to new people.


Michael:
             Yeah.


Ryan:
                   You know what I mean? So, let's talk tactics, right? Tactically, you need some type of an onboarding program for new hires where you teach them this stuff, you teach them your process, whether it's video training, you bring people in classes and do live training. They need to be taught this in the same way that a parent would teach a child the way to behave in certain settings, right? They need to be taught these things.


Michael:
             Totally, yeah.


Ryan:
                   And they need to be reinforced at every single meeting. So, every week we'll celebrate a new highlight, a different core value, and we will call out and praise people who exhibited that core value over the previous week. Right? So, that's a way that we can kind of bring it up.


Kathryn:
             Yeah.


Ryan:
                   So, it's not easy to do, but you got to bake it in.


Kathryn:
             Yeah, that's good.


Michael:
             Okay. As we kind of pivot around, as I watch our time here, there's a couple of different things I want to do real quick. We're going to end, there's ten questions that I want to ask that actually come from, have you ever seen Inside the Actor's Studio?


Ryan:
                   Oh my gosh, I saw it like years ago.


Michael:
             Years ago, right?


Ryan:
                   Mostly my understanding of it is Will Ferrell's, how he did the SNL skit?


Michael:
             About it?


Ryan:
                   Where he pretended to be the guy.


Michael:
             Yeah, yeah, yeah. Okay. Well, at the end of all of that guy's interviews, he asked ten questions that he got from a famous French reporter called Bernard Pivot.


Kathryn:
             Spelled pivot, by the way.


Michael:
             Yeah, pivot.


Kathryn:
             Pivot, but it's Pivot.


Michael:
             I'm trying to ask people this morning, so does anybody here in the office pronounce anything, because I've just got pivot there. Mr. Pivot, who's this older guy now, he's like 89 years old and has eyebrows the size of small Chinchillas. But he's got these ten questions that he always asked. We're going to end on that. But, before we pivot to that, if you're talking to a leader, he or she has been in business ten years, they've got a nice thing going, they want to continue to grow, they want to grow past whatever level they're at. And they're saying, okay, what's like the best piece of leadership advice that you could share to that person? What would you think?


Ryan:
                   Well, I think you first have to say, do I have the capacity to grow? Let's say you want to grow ten times, right? And you have to ask yourself, within the business we have right now, do we have the capacity to grow that much?


Michael:
             Okay.


Ryan:
                   So, think about the market that you're serving, right? Could you go and get ten times more out of those people easily? If the answer is no, that's a challenge. Could you charge the people you have ten times more than you're charging right now and get all of them to do it? Oftentimes, the answer is no. So, just the idea of growth. There's going to need to be some growth on your part from a leadership perspective, but you also have to have the right strategy in place to make sure that you're playing a game that you can win.


Michael:
             Yeah.


Ryan:
                   And that's why I encourage people, look at your market, look at your audience. And either you need to take what you're doing right now and pivot it into a market that's ten times larger, or take what you're doing right now and figure out who would be willing to pay ten times more than what I'm charging for this same thing.


Kathryn:
             Mm-hmm (affirmative).


Ryan:
                   So, those are two questions to ask just that are going to derive growth. And it might be some combination thereof, but I would pick one of them as a strategy and go there.


Michael:
             That's good.


Ryan:
                   And ideally, you can do it without having to change your current market. The hardest thing in the world to do is to take a product into a new market. Far easier to continue to serve the same market with a higher value product.


Michael:
             Yeah.


Ryan:
                   So, that's going to be the first thing I'd say. When it comes to those broader, okay, how do you make sure that as this growth happens that you remain the person who continues to lead it? Every single, I mean, at least every quarter, you basically need to fire a significant aspect of yourself. So, at that level of growth, you've got to ask yourself, what am I doing that somebody could be doing better? Because, when you're a growing company, the biggest inhibitor, aside from just we don't have the market, like we don't have the right strategy.


Michael:
             Right.


Ryan:
                   Again, we talked about before, companies fail because they run out of money. Companies do it because they've got the wrong strategy. So, you've got to get the right strategy in place. But next to that, the thing that will prevent the growth of the company is the leader, it is the founder. And it's because a company will only expand to fill the capacity of its leader. In the same way that like projects expand to fill the time allotted, companies will only expand to fill the leadership capacity of that company's leader. And so, you're not going to just get better.


Michael:
             Yeah.


Ryan:
                   That's the bad news. Good news, bad news, I guess. You're not just magically going to get better. What you have... everything. What you have to do is continue to get better by focusing in and only doing the thing that you're actually good at. And it sounds cliche, right? It sounds trite. You've heard that like, oh, I need to focus.


Michael:
             Mm-hmm (affirmative).


Ryan:
                   But, in practical matters, what it looks like is examining quarterly, what am I doing that I probably shouldn't be doing anymore? And it usually looks like hiring or promoting somebody from within, and it looks like holding those people accountable. That's the other hard things.


Kathryn:
             Yeah.


Ryan:
                   Leaders will hire somebody, they'll put somebody in, and then they'll abdicate all responsibility for that.


Michael:
             Right.


Ryan:
                   You got to hold them accountable. And, if they're failing to do the job beyond the standards that you had put in place, they're failing in that job beyond the standards, they got to go and you've got to get somebody else in.


Michael:
             That's good. One of the things that we talk about around here, I heard Roy, you've all heard us talk about Roy Williams periodically. And Ryan is a friend of Roy's also, knows Roy way better than we do. But one of the things that Roy said that I remember years ago is, he goes, I like to work with leaders who have long shadows. That was the way he described it. And I thought... matter of fact, he actually was talking about clients that he would hire and fire because he didn't want to work with people who didn't have long shadows because he knew that, if they grew the company and they didn't have a long enough shadow, i.e. they weren't mature enough and growing, they wouldn't be able to handle the company and it would shrink again, on top of cause, wreak havoc everywhere.


Kathryn:
             Yeah.


Ryan:
                   Yes.


Michael:
             And I just really liked it when he said that. I thought that was cool.


Ryan:
                   Yeah. I think most business have the capacity to grow much larger than they are right now. They're limited by the capacity of the leader. And so, what you shouldn't be thinking is, well, how do I hire another CEO? If you're the leader, you're the leader. All right? For better or worse, you're in it. You own the company, you're fricking in it, right? So, this idea of like, oh, I'll hire a CEO and I'll just kind of go off and do... no, no, no. You're in charge. All right? You're in charge.


Ryan:
                   Hire for your inadequacies. So, hire executive people who still report to you so that you can maintain and hold on to that vision.


Michael:
             Yep.


Ryan:
                   You should only completely fire yourself from the company when you sell it.


Michael:
             Yeah, I like that. Good. You ready for the ten questions?


Ryan:
                   Let's do this.


Kathryn:
             Let's do it.


Michael:
             All right. Ready? One, what is your favorite word?


Ryan:
                   My favorite word is grace.


Michael:
             Oh.


Kathryn:
             That's a good word.


Ryan:
                   And I will tell you, and so obviously, I mean, there are reasons that I would say for obviously, I mean, I'm a practicing Christian and my faith is an important part. And so, grace from that perspective is meaningful. It also is a word that we use a lot at the company when we talk about extending grace to one another, giving one another the benefit of the doubt, right? And what that means is separating the way someone made you feel from the way they intended to make you feel. And so, we just use that a lot. Like, let's give some grace, let's give some grace. We've had a hard time. And I've seen it save a lot of relationships and create enough room and enough narrative for somebody to go up to somebody else in the company and go, you know what? It really pissed me off when you said that. And the will person go, gosh, I'm so sorry. I didn't mean it at all that way. And now we've got something. So, that's why for multiple reasons, I would say grace.


Kathryn:
             That's a good word.


Michael:
             Nice.


Kathryn:
             All right. What's your least favorite word?


Ryan:
                   I would say months. Anytime-


Michael:
             Months?


Kathryn:
             Months?


Ryan:
                   Anytime I hear something is going to take months, it pisses me off. So, I've told people here and they know me, my team knows me, if it's going to take months, I tell people all the time, I want hours, days, and weeks at most. Those are the units of measurement that you're allowed to give. I do not want to think in terms of months. We don't do things that take months. If it's months, then break it into something smaller.


Kathryn:
             That's awesome.


Michael:
             So, if it's going to take 35 weeks, you'd rather hear 35 weeks?


Ryan:
                   I'd rather hear 35 weeks.


Michael:
             I like that. Okay.


Ryan:
                   It works for pregnant women, it'll work for you.


Kathryn:
             Fair.


Michael:
             Okay, so the next question is, what turns you on? It doesn't have to be sexual.


Kathryn:
             Please look, don't let it be sexually.


Michael:
             Please don't let it be sexual.


Ryan:   
                I absolutely assumed it wasn't. Yeah, no. Learning something new. Anytime I can really get to dive in and I enjoy mastering. It doesn't have to be business-related. I just love being able to dive in and I enjoy being a student.


Kathryn:
             Nice.


Michael:
             All right.


Kathryn:
             All right, and conversely then, what turns you off besides months?


Ryan:
                   The having to do something that I don't want to do and I know it isn't actually helpful in the long run. So, I'm willing to do the things I don't want them to do if I know that they're going to scale and that they're going to help. But sometimes you got to do the things, I over committed, I feel obligated in some way, shape or form, and I know that it just... but I got to do it.


Kathryn:
             Yep.


Ryan:
                   And I'm bad at over-committing. I'm bad about saying, oh, you know what? I got that. And I've found that it robs me of energy and it robs other people of opportunity when I take on a task I shouldn't be doing. And it's not doing anyone a great service if I commit to something that I don't actually want to do, somebody else could be doing that instead.


Michael:
             No, that's good. And, in leadership, it's the first step towards burnout when you consistently do that.


Ryan:
                   Yeah.


Michael:
             And so, I think that's great. All right. What sound do you love?


Ryan:
                   I mean, I love the sound of walking in the door and hearing my kid's voices going, Daddy. That's probably the one that, especially after a long day, after a long trip, kind of win lose, just knowing that I'm walking in that door and I'm a hero to them, no matter what happened that day. That there's nothing that I could have done that would make them not be excited that I'm home. That's probably my favorite sound.


Kathryn:
             Nice.


Michael:
             It's pretty sweet. And enjoy it because these days will go by quicker than you think.


Ryan:
                   I know. I've seen it.


Michael:
             I know you say it, but it's amazing when they go away to college and all of a sudden you're like, nobody is here at the house to greet me. Even the dog doesn't want to come say hi to me.


Ryan:   
                Yeah. My oldest just turned 13, so I can see it. He's not running up anymore.


Michael:
             He's getting so tall. Yeah.


Ryan:
                   Yeah.


Michael:
             It was great seeing him at T&C too.


Ryan:
                   It was cool having him there, getting to share in that.


Michael:
             It was fun watching him watch his dad.


Kathryn:
             Yeah, definitely.


Michael:
             And the steaming poop. I loved watching his reaction to the steaming poop. That's for another conversation, for the rest of you who are listening. What sound do you hate?


Ryan:
                   I think the sound that I hate the most is silence. I don't do well if there's no sound at all. I know a lot of people do, but if I'm in a house by myself, despite the fact that I'm an introvert, I don't like being alone. Yeah. So, anytime I'm by myself, I want to go somewhere where there's at least some other noise. If there's silence, I don't do as well.


Michael:
             Yeah.


Kathryn:
             Interesting.


Michael:
             That's good. That's good.


Kathryn:
             All right. What's your favorite cuss word?


Ryan:
                   I don't think it's a cuss word per se, but I use the term chucklehead a lot to describe how I feel about someone or something. And I definitely intend it very negatively. So, that's the one that I go to regularly.


Kathryn:
             Chucklehead. All right. I like it.


Michael:
             Okay. What profession other than yours would you like to attempt?


Ryan:   
                I'd love to be a curator at a museum, art curation.


Michael:
             Really?


Ryan:
                   Yeah. I love art and art history. And I think that would be a tremendous amount of fun to be able to pull together different exhibitions and things like that.


Michael:
             Yeah. Based on our conversations before about art, I can see you doing that.


Kathryn:
             And what profession would you absolutely not want to do?


Ryan:
                   Professional football. Like, I mean, anything-


Kathryn:
             Well, you're under-sized, so.


Ryan:
                   Anything where you get hit or that it's painful in any way, shape, or form, hockey, UFC, like these professionals, I'm just like, that seems terrible. I don't want to get hit. I don't want to hit somebody else. I would feel bad. So, no. That's when I'm really like man, I don't like that.


Kathryn:
             Okay. No linebacker for Ryan Deiss. He is not doing it.


Ryan:
                   No, I don't want to get hit. It seems like it would hurt.


Kathryn:
             I hear you. I am all over that. I don't even like the pain I cause myself at the gym. So, I'm totally with you.


Michael:
             That's one of the reasons I played soccer. Soccer was less of a contact sport. Okay. So, the last question is, if heaven exists, we all have established that we all believe heaven exists, what would you like to hear God say when you arrive at the pearly gates?


Ryan:
                   Well done, good and faithful servant.


Michael:
             Come on.


Kathryn:
             That's a good Sunday school answer and a good answer.


Ryan:
   I mean, what more can you hope for, right?


Kathryn:
             Yeah.


Michael:
             That's what I want. I dream about that one. That's a good answer.


Kathryn:
             I want him to say, you did what I wanted you to do.


Ryan:
                   Yeah.


Kathryn:
             Well done.


Ryan:
                   Yeah.


Kathryn:
             Yeah. Good stuff.


Michael:
             All right. Is there anything else you'd like to add, Mr. Ryan Deiss, to this obscure conversation?


Ryan:
                   I would just, for people listening, if you're struggling and it's hard, it's supposed to be. If it ever gets really, really easy, just know that's not going to last. I think the natural state of the entrepreneur is one of just frustration to beating your head against the wall. And good news, bad news, it's never going to go away. You're never going to arrive. It's never going to be done. The zeros at the end get more abundant, but it's always just dealing with the same thing over and over again. It's a bit like Groundhog Day, and you can either be excited by that or frustrated by it. And, if you're excited by it, then you probably have found the right career. And, if you're not, then I would encourage you to go and play a role in somebody's business who is excited by that, because there's nothing wrong with that at all.


Kathryn:
             Yeah.


Michael:
             Good word.


Kathryn:
             Good word.


Michael:
             Hey, thanks for joining us today and making the time. I really appreciate it.


Ryan:
                   It was a pleasure. I look forward to seeing y'all in a couple days.


Kathryn:
             Okay. I have one last question.


Michael:
             Yeah, one last question.


Kathryn:
             Okay. One last question, what was your favorite part about Universal Studios with your son this last weekend?


Michael:
             Oh, yeah. She's been waiting to ask this.


Kathryn:
             I've been wanting to ask that question.


Ryan:
                   Yeah, I know. The Harry Potter ride is amazing.


Kathryn:
             Yeah?


Ryan:   
                It was so much better. Yeah, it was so good. We rode it five times.


Kathryn:
             Nice.


Ryan:
                   So, get the unlimited pass. Because there's like a hundred minute wait, and we just kept going back again, and again, and again. That's one thing, I hate lines. I hate them. I'm allergic to them. I will spend ungodly amounts of money to not have to stand in the line.


Kathryn:
             To pull the line.


Michael:
             Yeah. We will too.


Kathryn:
             Yep, I'm with you.


Michael:
             No, that's good to hear.


Ryan:
                   No. But get that unlimited pass.


Michael:
             Because I haven't talked to anybody who's actually ridden that ride.


Ryan:
                   It was one of the best rides. It's very good, really well done. Really, really well done. That and the Mummy Returns ride, also highly recommend it. And the back lot tour, go the VIP route. They actually let you get out of the tram and walk around the different things, so.


Kathryn:
             Oh.


Michael:
             Yeah, I saw you guys in that video walking by the plane, the crashed plane.


Ryan:   
                Yeah. That's from the set of War of the Worlds, Spielberg's film, War of the Worlds.


Michael:
             Yeah.


Ryan:
                   And it's just there and you get to walk around. If you're in the tram thing, you just drive by it and they point at stuff.


Kathryn:
             Wow.


Michael:
             Nice. All right.


Kathryn:
             Looked like a fun trip.


Michael:
             All right. Take care, brother. Thank you very much.


Kathryn:
             See you soon.


Ryan:
                   Thanks, y'all. See you soon.


Kathryn:
             Bye.


Michael:
             Bye.