Andy has been in the web design and interactive marketing space since January of 2000. In that time, he’s helped thousands of people do a better job getting results online. He’s a true evangelist for content marketing and ethical digital marketing.

Together with the team at Orbit Media, Andy has put out some of the best digital marketing advice available in hundreds of practical articles, including posts on virtually all of the top marketing websites. Then there’s the book, Content Chemistry, which is currently in its fifth edition.

Andy is also a regular speaker both locally and nationally. Not only is Andy a founder of Content Jam, Chicago’s largest content marketing conference, but he’s also a regular face on the national circuit. If you go to a content marketing conference, the one Chicagoan you’re most likely to hear is Andy Crestodina.


Looking to grow a real estate empire but don’t know where to start? Pick up a copy of Money, People, Deal by Stefan Aarnio for only $3.95 at

To get exclusive podcast listener only offers for the 100K Challenge (like a free hotel room for the event), email Devin Savage at

To learn more about the 100K Challenge visit


Stefan Aarnio: Ladies and gentlemen, welcome to the show Respect The Grind with Stefan Aarnio. This is the show where we interview people who’ve achieved mastery and freedom through discipline. We interview entrepreneurs, athletes, authors, artists, real estate investors, anyone who’s achieved mastery and examined what it took to get there. Today on the show, we have Andy Crestodina, he is well known for content marketing, SEO, and he is one of the leading speakers in the United States. We’re talking about content marketing and getting traffic to your websites. Andy, welcome to the show, Respect The Grind. Thank you so much for joining me.

Andy Crestodina: Awesome. Glad to be here.

Stefan Aarnio: Awesome, so Andy, you know, for the people at home who don’t know you very well, tell us in your own words who’s Andy and where’d you get started with all this stuff?

Andy Crestodina: Sure. I’m the guy who grew up here in the Midwest, outside of Chicago. Went to college in Iowa, here in the Midwest. I didn’t know what to do, I was kind of a slacker, ended up with a degree in Mandarin because it sounded hard and interesting, so I got a Chinese degree. Moved to China, lived in China for a year. It was good, it was fun. I decided I didn’t want to live in China, so I came back and took a crappy job in a bookstore. I worked at like a Barnes & Noble, and lived in mom’s basement.

Stefan Aarnio: Hey man, that’s what I used to do too.

Andy Crestodina: Yeah, you gotta start somewhere. Kept making lattes and living in mom’s basement. Didn’t know what I wanted to do, decided I didn’t want to live in China, so I went and moved to the Chicago suburbs. Basically had a day job, didn’t find it very interesting. Did really, really well, but wanted to do something creative. This was the late 90’s, wanted to combine art and science and creativity and technology, so quit that job, and in January of 2000 started building websites with my buddy, friend from high school, roommate from college, and basically just kept going.

Andy Crestodina: This is 18 years later, it’s a four and a half million dollar company with 36 people. We’ve done fifteen hundred web design projects over the years, but right after building the first few figured out I had to figure out search and analytics, back in the beginning when analytics was spelled with a lowercase ‘A’ because Google Analytics wasn’t out yet. Then about 11 years ago, started writing, publishing, combining search and social media, and marketing. Not long after that, started doing lots of live events, gradually got into creating videos, and I’ve done some Podcasting. Basically I’m 11 years now into that content path. I wrote a book and I’m a guy who gets out there and just teaches this stuff at conferences all over the world.

Stefan Aarnio: Wow, I love it. You know what I love about the story is the 18 year grind. This show is Respect The Grind, you went on the grind for 18 years, started in mom’s basement. Now, let me ask you this, Andy, out of all things, you had a background in language studying Mandarin, obviously if you’re studying Mandarin, you gotta study English as well to translate the two. Out of all things, why did you choose websites and content marketing and all that stuff? Why didn’t you become an author or a book publisher or something other … Why did you get enamored with the internet?

Andy Crestodina: Necessity? Well, originally it was the idea of using both halves of my brain at the same time. This is analytical and this is creative, and I’m gonna smush those together, and it just sounds hard and interesting and fun and challenging. I liked it from the beginning. I had no mortgage, and it was an easy thing to do at the time, but I also liked the hustle which you can probably appreciate, just the getting out there and making it happen and starting something new, the initiative that comes with it cause these were early 2000’s.

Andy Crestodina: I liked the people side of it because it’s a totally service driven industry which is people everywhere, now it’s called influential marketing, but the networking from the beginning. It just kind of hit every note for me, I’m well suited for it. It combines all the things I love, it’s creative, it’s technical and it’s service.

Stefan Aarnio: I love that. It certainly is a blend of disciplines. Now with the content game … content today is the new money, content is everything now. I took an English degree back in 2008, I graduated at University of Manitoba. I’m in Winnipeg, the Chicago of the North, man. English degree was totally useless back then. I got a job at a call center. I lived on my mom’s couch. I rode the bus. I had long hair. I was writing rock band songs, and writing lyrics, and poetry, and stuff. I couldn’t get a job.

Stefan Aarnio: Mark Cuban recently said that an English degree is now one of the most powerful degrees today, it’s one of the best degrees. Can you maybe give us some ideas of why writing and content 10 years ago wasn’t so great, and today it’s the new money, it’s everything?

Andy Crestodina: Well, if you think about why someone pays attention to something, that thing is either entertaining them, or teaching them. Basically making them happy, or it’s solving for one of their information needs. So why do people pay attention? Why is anybody listening to us now? Because there’s some value in it, it’s utility, it has value, so it’s gonna help them. The English degree comes back to communication which is the vehicle for conveying that to the listener, the viewer, the reader.

Andy Crestodina: The only reason why anybody knows about me, or pays any attention is because I’ve given away all my best advice for so many years. My approach to [inaudible 00:05:49] is basically to teach, I’m not that entertaining, I just try to teach. I teach the hard stuff. I want to teach people how to do analytics. I want to teach people why things rank, and why they don’t. That’s why people buy the book or attend the event or buy a ticket or tune in or search or click or subscribe. It makes sense, I agree with Mark Cuban. If you understand the mechanics of demand, it all comes back to the point, which is what is the true story in the life of that person, and how can we get and hold their attention, increase awareness, and the chance for a commercial outcome by giving away … it’s a contest of generosity, whoever’s best at giving away their best advice wins the largest audience and the most attention.

Stefan Aarnio: Wow. You know what right there, my guy, Luke, here in the office, he’s watching, he’s like fist bumping some of that stuff you said. It’s like man, that’s great. I love what you said about we only listen or pay attention to things if it’s entertaining us, or teaching us.

Stefan Aarnio: Let me ask you this, how can somebody create a good piece of content, like a great hook, that both entertains and teaching? Is it done through storytelling? How do you get the holy grail content cause I’m like you too, I got teacher mode, like some of my YouTube videos, it’s just hardcore white boarding. I think it’s boring, I don’t want to watch it myself. Actually, I had a bunch of SEO articles I’m getting written by a writer cause I don’t want to just write technical articles about flipping houses [inaudible 00:07:15] boring.

Stefan Aarnio: On the flip side, I’m writing books, getting into fiction now. That’s more interesting, but maybe doesn’t teach anything. Tell me how could someone blend the two and make a real great hook piece of content that you know is gonna be a real hit. Almost like the Tai Lopez, Here In My Garage. He’s teaching you, hey man, you don’t want the Lamborghini, you want the books, but it’s also entertaining as hell. How does someone do that?

Andy Crestodina: Well, start with the topic, and define the relevant topics, pre vetted topics, just think about what people ask you. What are you to the world? What do people talk to you about? What do people get excited when you show them? What do people keep asking you? Scan through your email, look through your sent mail folder, and you’ll find all the things that people want from you in general.

Andy Crestodina: Now you’ve got your topic. Next, you need to explain that in a better way, more detailed, thorough, complete covers it from every angle way than every one else who wrote about that topic. [inaudible 00:08:08] long-form, or it’s a super detailed step-by-step video that doesn’t skip any steps. Now you’ve got a quality piece of content on a pre vetted topic that you know at least one person wants, right? If no one else, you’re gonna send it to the people that you exchanged the emails with to where you found the topic in your inbox.

Andy Crestodina: Finally, to not be boring, you have to maybe forget about the English degree, or a lot of people have this writer’s block where people try to write things that are so accurate that they put in so many qualifying words, or they water things down where they want to make it perfect, or there’s so much throat-clearing language at the beginning. The first three sentences, just cut them. Cut out all the extra words, be more direct. Be more forthright in a truer voice by just cutting the chase. Think about the write as you like, there’s no flaws. Even [inaudible 00:09:03] says, “Write what you write, then cut out ten percent,” so basically just don’t hold back, which you’re good at, and just be more direct, and to the point by removing all that extra qualifying language … important topics, coming straight at you.

Stefan Aarnio: I love what you said there. Martin Scorsese, the great film director, he said .. I was watching one of his MasterClass clips, you know they got Gordon Ramsay MasterClass, Martin Scorsese, they’ve got all these writers and amazing things. I love what he said, he said, “The thing about filmmaking is, don’t waste the audience’s time.” Just don’t waste their time, is this a repeat of something, is it a bad cut, just don’t waste their time. I thought man, that’s amazing. When I used to be a poet or a writer, I still am, is I’m always trying to get fewer words. If you say it in two, get it down to one. If you get it in ten, get it to five. Do you agree with that?

Andy Crestodina: That’s a huge part of the game. Basically, if we’re in digital, every website has one thing in common. Every blog post, every article has one feature in common, it’s the back button. They are one click away from every other article on the internet. So we have to live in fear, it’s healthy, live in fear that they’re gonna stop paying attention, so you use short words, short sentences and short paragraphs, but write the longest, most detailed article you possibly can.

Stefan Aarnio: Man, you’re dropping some nuggets today, and this is great stuff. It’s crazy, I haven’t seen you speak on stage, but I bet its phenomenal.

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Stefan Aarnio: One thing that I think is new right now … I’m a content marketer, like yourself, probably a baby. You’re probably an adult, I’m a baby over here. I saw Jordan Peterson. Jordan Peterson’s got one of the biggest non-fiction books selling right now. I think he’s number one for non-fiction books, 12 Rules for Life, I don’t know if you’ve heard of him.

Stefan Aarnio: An interesting thing has happened on the internet right now where for the first time in history, long-form content is now able to be used for free by the audience. Jordan Peterson, I don’t know if you know him, he’s a university professor at University of Toronto, he gives these long philosophical lectures, and he got famous because he didn’t want to use the gender-neutral pronouns, Ze and Zir in the university, so I think they took away his professorship, but he got huge off of this controversy. He puts his lectures online, and you can go on YouTube and watch them for free.

Stefan Aarnio: He was saying when he was speaking, “This is the first time in history long-form content is available for free, and that’s why I’m huge and never would have been huge before.” What do you have to say about that, with long-form content coming out? On YouTube you can watch a one hour lecture for free, in the old days, bro, you’d have to get a VHS tape [inaudible 00:12:23] in the mail, it would cost shipping, it would take two weeks. Let’s talk about that.

Andy Crestodina: The idea of it being free is the trade off that we make. In the insanely competitive context of content, someone else has published it anyway, so you have to give it away. Of course you need a business model where you’re going to eventually monetize this audience that you’re building. There’s a handful of ways too that we could talk about.

Andy Crestodina: The idea of going long in general, that idea is really important because if you stop writing, or stop talking, you’re basically just cutting them off. They hit the bottom of the page. You told them you have nothing more for them. Your page was a dead end.

Andy Crestodina: It’s a quote from Jerry Seinfeld … when people say, “Well, I shouldn’t write long, my audience doesn’t like to read long, everyone has a short attention span.” The problem isn’t that the audience has a short attention span, the problem is your writing is boring or useless. Jerry Seinfeld said that there is no such thing as attention span. People have an infinite attention span if you’re entertaining them. The point is people will pay attention for very long periods of time if the quality’s high enough, and there’s utility and entertainment value.

Andy Crestodina: I don’t think there’s a good case for writing shorties, or the snackable content. Why not keep giving them more? If they want to keep paying attention, they will. If they’re done, they’ll just bail out and do something else.

Stefan Aarnio: Wow. I’m gonna hit the gong here. You gotta have some entertaining content, man, that’s sick. I think the game right now is edutainment, I think Tai Lopez calls it, edutainment. It’s not necessarily just teaching, or not just entertainment, it’s edutainment. I think that’s the new thing. Andy, someone at home listening to this, we got a lot of real estate investors listening to this show, we got small business owners, how can some of these people get started in the content game? I get people always asking me, I’ve written five books, hey man how do I write a book, how do I start speaking, how do I build my platform. How would you recommend building the platform, as a guy like yourself, who’s an expert at building platforms, how could a brand new guy get into this?

Andy Crestodina: The more crowded the niche, the more specific you gotta get in your topics. It’s already a really crowded space in a lot of the real estate categories. I’m in Chicago, I had a meeting with a guy, he’s like, “I’m in real estate, what should I talk about? I don’t know what to do, everyone’s already done everything.” Within a few minutes, we came up with some niche topics and areas that he could carve out some attention, like Chicago’s got a river. There’s a couple of thousand homes on the river. You could easily become the specialist who’s doing that, right? He knows everything about the properties on the river, if you want that, you go to him. He’s the guy who wrote everything about it, he knows the laws about it, he knows everything about boat docks and whatever else, there’s millions of things.

Andy Crestodina: So if you’re in a crowded space, either geographically or in your topic, niche down you’ll get faster growth. A lot of people think that’s counterintuitive because they want a big audience, but it doesn’t really work that way. The more specific your topic, the faster you’ll grow within that topic. Also, the more love you’ll get, the more loyalty because the people who are interested in that will know that you’re definitely the leading source for that. So ask yourself, what can I be the best at, what can I be the foremost expert at, and it can’t be too broad if you’re in a crowded space.

Stefan Aarnio: I love what you said. People say rich in the niche, or if your French you say riche in the niche. We’re from Canada, we say riche in the niche; you say rich in the niche.

Andy Crestodina: Did I say niche? I know, that sounds horrible to you right?

Stefan Aarnio: Well, it’s America man. I normally wear this big crazy America sweater, it’s like American flag and I’m in Canada, and everybody gets pissy about this America sweater. I just think it’s awesome. I say I’m wearing freedom and liberty every day, but Canadians we think it’s like hockey season playoffs every month, so they get mad at my America sweater, but [crosstalk 00:16:22]-

Andy Crestodina: Niche sounds a lot better. I should switch to niche, it does sound a lot better.

Stefan Aarnio: Riche and niche. Awesome, well that was a starter question. I want to ask you an advanced question, for the people who maybe are dominating their niche. How can a person who’s dominating their niche get into more mainstream? How can they jump that barrier?

Stefan Aarnio: One thing that someone like myself is bumping into is in Canada, I’ve already got top three SEO for a lot of phrases like, ‘flipping houses in Canada’ and some things like that, but when I want to go to the media or let’s say I want to go to a bigger Podcast, they say, “Oh you’re some house flipping guy. I don’t want to talk to you.” How does somebody break out of their niche now and into more of a mainstream game or do you even recommend that?

Andy Crestodina: I think that there’s no argument for staying in that level. Once you’ve been successful at that level, definitely expand up to the larger audience. Even if you have just a personal fulfillment for helping people, you want to help more people. If you believe in your message, you should want to bring it to the largest audience that you can. I would never argue against trying to keep a smaller audience. You’re not going to lose relevance with your niche audience when you go bigger. People who love wine still love Gary Vaynerchuk for his wine advice, but now he’s a [inaudible 00:17:45] leader in the much broader topics and he’s helping more people with more advice.

Andy Crestodina: The way to do it, I think you’ve got to work backwards from success, so pick the publication you want to be in, or the podcast you want to be in. Now [inaudible 00:17:59] person who’s going to let you in, their not gonna choose you you’ve gotta reach out, the person who’s between you and being in that publication, Entrepreneur Magazine. Who is it? There’s an editor. Who’s the editor? She also has an English degree. She went to school in your province. You need to use your people skills, and do some research to figure out how best to connect with the person who’s going to let you into the party on the next floor up. It’s really just a PR thing. It’s about the angle, it’s about the audience, and when you’re pitching editors, or podcasters, or hosts, or TV producers, that audience is one person, so dig deep, take your time and think big.

Stefan Aarnio: Let me ask you this, Andy, I think a lot of people are saying, “Oh I want to build my brand.” These days that’s almost a mainstream thing. Everybody’s a coach now for some reason. Everybody’s a speaker. Everybody has a book. Everybody wants to be this celebrity. For some reason, celebrity is like the new job. Little girls at school who are like 17 be like, “I want to be an Instagram wife. I want to be an Instagram mom.” It’s like what, you’re gonna be a professional celebrity? That’s what people want to be, but they see that that’s what they can be.

Stefan Aarnio: Grant Cardone, he’s a guy I listen to every now and then, I read his books. He says he’s got a hundred million dollar company, he’s going for billionaire right now is his goal, he says he’s never been happy with any PR firm out there. What do you think of that statement? You mention, hey man reach out yourself, reach out to the next level. What do you think about buying PR or hiring a PR firm? Is there a such thing as a good PR firm who can do some of this for you, or do you have to bring it in house?

Andy Crestodina: You know, I kind of had this debate with someone yesterday. We were talking about thought leadership. Can you delegate thought leadership? Can you [crosstalk 00:19:57] leadership?

Stefan Aarnio: Can you delegate [crosstalk 00:19:57]? (laughs)

Andy Crestodina: Yeah, I know! It’s like, what’s your goal? I want to be a thought leader. Basically the same thing, I want to be a celebrity, I want to be known, I want to have notoriety. So you want to be a thought leader? Okay great, you’re gonna outsource that? What are you thinking about? What are you leading people on? What do you believe in? What are you against? What are you for? What are your strongest opinions? Oh, I don’t know. Okay, if you don’t have any thoughts, you can’t be a thought leader. It’s not gonna happen for you.

Stefan Aarnio: Bro, I gotta hit the gong for that. If you don’t have any thoughts, you’re not a thought leader. Oh man, damn.

Andy Crestodina: You can delegate tasks. You can’t delegate strong opinion. You can’t delegate beliefs. You can’t delegate what you stand for. You can work with a communications pro to help you craft that message and package it, but you gotta get behind something. Sometimes you’ve gotta come down to get something. Who’s your secret enemy? Who do you really think … What are you trying to defeat? You want to slay dragons. You want people to believe you and follow you? You’ve gotta have a bigger purpose. People don’t follow you unless you’re actually leading in something.

Andy Crestodina: The idea of the obsession with fame is a weird one to me. I heard a quote once there’s basically two kinds of currency, there’s fortune and glory. Some people, if you just think of fame and attention as another type of currency it all makes more sense. Even though, I think that … I know a lot of social media celebrities and influencers, and some of them aren’t doing all that well. When you look at it as an Instagram or wherever, it looks great, but I don’t think that they’re necessarily … There’s no symmetry with success in other ways. They might just have a lot of followers and be a good photographer.

Stefan Aarnio: I have a friend of mine, Dan Walk, up in Canada, in Vancouver. I don’t know if you’ve seen him on YouTube, he’s going real big on YouTube right now. He says, he was at a conference and they wanted to ask him, “How do I monetize my two million followers,” or whatever. He said, “Bro, if you’re not monetizing a thousand followers, you’re not going to monetize a million.” He said, “Get a thousand followers and monetize it. If you’re at two million, you can’t monetize, you’re screwed.” What do you think of that statement?

Andy Crestodina: Yeah, it’s a bit late. If you’ve read Joe Pulizzi’s Content Inc., you should have thought about that a little earlier. You should be able to monetize two million followers. You can actually just work with an agency, if you’re that big of an influencer, there are influencer agencies that will want to rep you and connect you with brands. There’s only so many ways you can do it. You can sell your time as a consultant. You can sell books. You can sell butts in seats and sell tickets and create an event. Unless you want to do client service work, or some kind of coach maybe that explains why there’s so many coaches now.

Stefan Aarnio: There’s a million coaches man. There’s coaches on coaches on coaches and classes on coaching and how to coach and get coaching clients everywhere.

Andy Crestodina: It’s weird.

Stefan Aarnio: Dude, it’s totally weird. I was explaining to my … I coach real estate people and also do real estate, and I was explaining to my social media guys we might open up a coaching company, how to be a 7 figure, 8 figure coach, and my-

Andy Crestodina: I know a guy, yep.

Stefan Aarnio: … My young 20 year old guy who does my bookings, his eyes got wide. He’s like, “You mean there’s coaches who coach coaches?” So you’re [inaudible 00:23:29].

Andy Crestodina: That’s crazy. Yeah, see that’s a crowded space again, so what are you gonna do? Niche down? Differentiate? Come up with a harder angle or different topic or go into a different format or do it on a different channel. That’s the red ocean, you gotta find a blue ocean strategy and get some white space. Do something that’s a bit different. You gotta put a spin on it there. The fastest way to die is to be a mid-level generalist. [crosstalk 00:24:05] You gotta put a different angle on it, or else you’re not gonna survive.

Stefan Aarnio: Andy, I want to add to what you’re saying there about the blue ocean, red ocean. One thing I’ve noticed these days, now every single person has a voice. Howard Stern, he said … in the old days, like the 90’s let’s say, Howard Stern was really offensive and you’re like oh my God, I can’t believe Howard Stern said that. Nowadays Howard Stern says, “Well, I’m tame now because every single social justice warrior has their own Instagram and their own channel and everybody’s screaming at the same time,” which brings me to the next point.

Stefan Aarnio: What do you think about, there’s two things that have happened in the last two years that have been major, major changes, I think, in the marketing, branding, PR space. One is Trump becoming President, and the other one is Kaepernick and that Nike ad that went out. Both of those campaigns were very polarizing.

Stefan Aarnio: I read about this with Trump, he actually hired a firm to go through his Twitter and build his whole platform off of what his audience wanted. So he said, “What do you guys want?” He didn’t care about a wall or anything. He just went and found his audience wants a wall, so he said we’ll give you a wall.

Stefan Aarnio: Nike looked at their audience and they said, “Okay who’s buying our shoes? Young black guys. Great. Who’s not buying our shoes? Old white guys who like football.” And then they’re just like, boom let’s double down on our buyers, and let’s say screw everybody else. Trump did the same thing, half the country hates him and he’s President. How does this happen today, in this world? Is this a new strategy [inaudible 00:25:36] controversial, taking half the people and say no way and the other half come love you?

Andy Crestodina: I’m like the millionth person to give the advice, focus on the people who care the most about you. That’s sensible, makes sense right? Don’t worry about the people that aren’t listening or don’t care or aren’t in your tribe. This is general business strategy advice or marketing advice.

Andy Crestodina: We should focus on the people who care the most about our message, but when you take that to the extreme you end up with these polarizing national figures and causes that have a real negative impact because if you decide that you don’t care about 49% … If you’re a national politician, and you’re willing to just give the finger to a third of the country because there’s another third over here that loves it when you do that, that’s not a good thing for democracy.

Andy Crestodina: As a business, strategy and marketing advice, you have to admit that stuff works. Nike did the math, it’s not a bad idea. We all kind of live in these filter bubbles now, the way social algorithms work, it’s positive reinforcement for whatever message you’re engaging with. I would still, even today, advise anybody to focus on their fans first, however there’s negative impact on democracy when you take that too far.

Stefan Aarnio: It’s huge man. I think when you get to that, it’s like the end game of the social media thing where it just gets so heavy. It’s like a back and forth basketball game, but it just gets higher and higher stakes over and over again. You start looking at it like people start throwing out … you know it’s crazy man, everyone throws out racism, or they throw out different terms to describe these things cause we got such a sensitive population now, and then we also have these people who are deciding to market in a very polarizing way.

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Stefan Aarnio: Let me ask you this, Andy, if you could go back to your old self … Let’s say today you’re established in the business, if you go back and give your 15, 16 year old self a piece of advice, what would you say to yourself?

Andy Crestodina: I’m old now, I’m 46, so that 15 year old was pre-internet. So my best advice to that kid would be buy a bunch of domains right away. The thing’s gonna come out, buy some big domains, because-

Stefan Aarnio:, man.

Andy Crestodina: … well not trademark domains, but business … What are the records? was 40 million or something.

Stefan Aarnio: Wow!

Andy Crestodina: Yeah, the most expensive domains. And where was I when that got registered the first time? I was drunk, I don’t know what I was doing. I was not paying any attention. We can all regret not doing that. I also was doing digital before Facebook started, and could have started any one of these companies, SurveyMonkey or Eventbrite or these cash cow businesses that just … I mean, we can all look back and say that we missed opportunities. Probably the most practical thing would have just been to go a little harder a little sooner on content and social. Dig deep and publish … 2007, how hard would it have been to make the best video or best article on any topic?

Stefan Aarnio: Bro, if you had a camera and turned it on, you win.

Andy Crestodina: Exactly, right, and what were we doing?

Stefan Aarnio: Being drunk.

Andy Crestodina: Yeah, I was not paying any attention. My friends who were on social 12 months before me have massive followings now. Probably could have been at that party a little sooner. I don’t know, I picked a bad business partner once, and that cost me a fortune. I got a bad marriage in my back, I mean we’ve all made some big mistakes. I’m super happy now, I married the woman of my dreams. I’ve got two awesome little kids. Finally getting into some real estate, which I love the path you’re on, and I think if it worked for Trump, it could work for a lot. The agency’s healthy, clients are happy, the team is good. I have the same regrets we could all have about, you know, missed that bus. Overall, I shouldn’t be complaining.

Stefan Aarnio: Yeah, sounds like you’re doing great. Let me ask you this, Andy, in the space you’re in or maybe you can comment just on entrepreneurship in general, what do you think’s the biggest cause of failure in people? What causes people to just straight up not get their dreams?

Andy Crestodina: Just recently, I’ve been thinking a lot about this. I think that there are people who just sort of believe that they have the chance at something big, but there’s nothing stopping them from being in the room, or making that pitch, or picking up the phone and calling that prospect or influencer, asking that famous person to collaborate with them on some interesting project.

Andy Crestodina: There’s other people who it’s like a self-defeating attitude where they just don’t think that it’s gonna work out, and they try less. What do they say, accomplishments are proportional to attempts. You’ve gotta try a lot of stuff, just keep trying a lot of stuff. I don’t want my kids to be afraid of failure. Failure’s fine, nothing wrong with failing, way better to fail than to not try.

Andy Crestodina: Take lots of swings at stuff, try big things. The risks are lower than you’d think, not gonna hurt that bad if it doesn’t work out, a lot of these ideas we have. I think that’s one of the big differences is people don’t realize that the hustle is about just visualizing that outcome, and think that you could do it, and try to do it, and take a shot at it, and fall on your face, and try it again and keep trying. I sucked at so many things, but all those mistakes I made have added up to a lot of learning and got me where I am.

Stefan Aarnio: I always say I fail at 80% of what I do, but the 20% makes up for all the failures. A couple more questions before we go, Andy. What’s the top three books that changed your life?

Andy Crestodina: I’m giving big props to The 7 Habits right now, just the way that … Stephen Covey 7 Habits of Highly Effective People. It’s fundamental advice about listening. People don’t listen to anybody who doesn’t listen to them, so you gotta learn that interpersonal kind of stuff. It’s a good one.

Andy Crestodina: There’s a book that sounds dorky, but I recommend, it’s good interpersonal tricks as well, it’s called … don’t laugh. It’s called How to Make People Like You in 60 Seconds or Less. I read it years ago, and I still think about it. He makes this interesting point where if somebody is cranky, don’t try to cheer them up. Be cranky with them, to get on that level of the person that you’re trying to connect with. If you see a door and you’re about to walk through a door, smile as you walk through the door cause the first impression is made long before people know it. First impression isn’t when you first talk to someone, they saw you 20 minutes ago when you came in the room. That’s a really good one, that’s definitely a really good one.

Andy Crestodina: There’s a good business book called Getting Naked, another funny title. Lencioni, awesome book! It’s about being vulnerable in business, not being afraid to be wrong, go ahead and say something dumb because people will correct you and they’ll forgive you, but you’re gonna learn more if you don’t pretend to be smart. Those three should be probably on any hustler’s bookshelf.

Stefan Aarnio: I love that. Some of those titles I haven’t heard before. Most people say Think and Grow Rich, Rich Dad Poor Dad, the basic hits.

Andy Crestodina: [crosstalk 00:33:51]

Stefan Aarnio: Yeah, I was gonna say [inaudible 00:33:52] people, but I love that you’re bringing fresh stuff to the table. Last question today, Andy, what’s the one thing that young people need to succeed these days, the Millennials? I was talking to a girl the other day, she was in Generation Zed, man, the after Millennials. I said, “Are you a Millennial,” she said, “No, I missed it by four weeks,” or something. I’m thinking holy mackerel, so Millennials, Generation Zed, the next group of people, what’s a piece of advice you give to them so they can succeed now?

Andy Crestodina: I’ve interviewed a lot of people applying for jobs here, and there’s a stereotype that Millennials have expectations about the workplace and what they want. They want opportunities and they want to manage people, they want leadership, whatever. I get that, but if you’re considering someone for a job or a project or a partner, and that person just talks about what they want, they’re missing the point. If you want to succeed at anything, you have to look around you, and figure out what everyone else’s goals are. If you understand other people’s goals and triggers, and help them get what they want, you’re gonna get everything that you want in the end. The greatest test is empathy and resourcefulness, and pay close attention to who gets what outcome and why, what they’re trying to do. A young person who focuses on that, I’d hire them in a second. That person is gonna help all my clients. Make it about you second, just spend a good ten years hustling and helping everyone around you succeed and things are gonna work out great.

Stefan Aarnio: I love it. Think about the other person. I love what Warren Buffett says, world’s richest investor, he says, “What you love about you is your hobby, what other people love about you is your business.” And that’s, what you said there, wrapped up in Warren Buffett’s wise, wise words. Andy, how can people get in touch with you if they want to know more or they wanna grab a copy of your book, how can people get in touch with Andy?

Andy Crestodina: is where I blog. I write a digital marketing article, content strategy article every two weeks. The book’s called Content Chemistry, it’s actually a big shortcut cause it’s got everything I know. 280 pages filled with pictures and diagrams, I’ll make sure you get one. Other than that, I don’t know. LinkedIn, connect with me on LinkedIn, ask me anything, happy to help any of the listeners however I can.

Stefan Aarnio: Wow. I was gonna say, we’re here on Podcast, so audio only, but I saw the video. He flipped through the book, it’s got real pictures, real color. That’s not a cheap book, that’s a real book, man. Go get that book, it looks tremendous. Andy, thank you so much for being on this show, Respect The Grind. Great to hear from you, man, and I wish you all the best.

Andy Crestodina: Respect. Thanks man.

Stefan Aarnio: Hey, it’s Stefan Aarnio here. Thank you so much for listening to this episode of my Podcast, Respect The Grind. If you loved this episode, I want you to check out my book, The Ten Commandments of Negotiation. Negotiation is one of the things that most entrepreneurs struggle with, in fact, many of them fail at it. My book, The Ten Commandments of Negotiation’s gonna show you the exact method, the exact steps that people use all over the world for creating massive wealth in real estate or in any other business. If you need to close the deal, if you need to sell, if you need to make things happen, if you need to negotiate, this book is a game changer for you, so you can get a special offer if you go to That’s the letter ‘X’, I’ve got a special offer for Podcast listeners only. That’s letter ‘X’, for a special offer just for Podcast listeners. Go there now, don’t delay. You’re gonna love what I have in store for you.