What does it take to be a super creative marketer?

Jason SurfrApp (formerly Jason Headsetdotcom & Jason Sadler) is an unconventional marketer.

Jason made over $1 million with IWearYourShirt, the company he created that used sponsored T-shirts to promote businesses on social media.

To take his marketing creativity further, Jason auctioned off his last name in 2012 and 2013 to the highest bidders.

Jason was featured on The Today Show, CBS Evening News, CNN, and The New York Times.



Read Raw Transcript Now:

Success Harbor: Hi everyone this is George Meszaros with Success Harbor and I have Jason SurfrApp with me. You may know Jason as ‘Jason SurfrApp’ or ‘Jason Headsetsdotcom’ or ‘Jason Sadler’. We’ll get into why all the different last names. Jason had made $1 million wearing t-shirts to promote businesses. His unconventional thinking enables him to create business opportunities which he documents in his book ‘Creativity for Sale’. Welcome.

Jason Sadler: Thank you for having me.

Success Harbor: Thank you for being here Jason. You have had so many unique marketing ideas that it’s hard to know which one to start with but tell me how you got started with ‘I Wear Your Shirt’, a company that uses sponsored t-shirts to promote businesses on social media.

Jason Sadler: Yeah, back in 2007, I left my 9-5 job working for a sports agency to start a design company with a friend and while at that design company, we had a lot of our clients ask us about social media and so this is like 2007, 2008 before anything really took off in social media time and I just saw an opportunity where brands wanted to reach people and that people were on these platforms and so I thought I could kind of fill in the gap and be the guy that promoted the company via social media and created a unique way to do that through this company, ‘I Wear Your Shirt’.

Success Harbor: And so, how did you even come up with that idea, it’s a genius idea to wear company shirts but I mean, was there a process to it or one day it just came to you?

Jason Sadler: Yeah, I think the idea just kind of came together through looking at these different free platforms; Twitter, Facebook, YouTube, seeing that people were just posting content and that a lot of people were able to talk to each other quickly and so those things were working in my mind and I remember one day, standing in my closet, as most guys do, staring at all these shirts and just not caring which one I was going to put on for the day and as an entrepreneur and somebody who works for myself, I didn’t have to wear a suit and tie or anything so it was actually more trouble to pick my outfit than it was to have it picked for me so, I just said, I got all these shirts that already have brand names on them, why not try and get brands to pay me to wear their shirt, that seems interesting, and that’s kind of where things started.

Success Harbor: And how much outreach did you have to do initially, and did people even take it seriously? Did they think it was a joke of some kind when you first tried to reach out to people?

Jason Sadler: Yeah, well I originally sent the idea to a bunch of my friends and probably more than half of them rightly so said, “Jason, this is a stupid idea, we’re in a recession right now, no one’s going to want to pay you to wear t-shirts, go back to doing whatever you were doing. And so, you know, I got that feedback and said, “Alright, well that’s their opinion, I still think this is an exciting idea, and so I had a website built, ‘iwearyourshirt.com’ was put up in October 2008 and only 12 people showed up to the website on launch day and I was really bummed because I thought I had come up with this amazing idea and yet no one seemed to care. So as you mentioned, I did some outreach, I started emailing some of my contacts and I didn’t have many, just friends and family, I didn’t know any businesses and just started to say, “Hey, here’s the idea”, personalized emails, I didn’t mass email them and started to get some interesting feedback and people started to see, “Oh yeah, I could buy a day”, you know, I was selling this whole 2009 calendar, starting at a $1 on the first day and $2 on the second day, all the way up to $365 on the last day, so it was very affordable, I mean cheap, to get on board early, and so that average really started to help and I jumped on Twitter and started looking at hashtags and started [inaudible 03:44] people and following interesting people and just jumping in conversations and not trying to sell but I think when people saw the username ‘IWearYourShirt’, they were intrigued by it and they started kind of looking into it so, you know, that was really how the outreach started when I first got it launched.

Success Harbor: So initially you didn’t think about giving up maybe because some of the feedback you received, you had enough positive feedback to kind of keep you going?

Jason Sadler: Yeah, I think–, I will never forget this moment, I was sitting on my couch and this was like right before the website was launching and I had reached a couple of friends and family who told me this wasn’t a great idea and I just sat there and said you know what, how many successful businesses are out there where people have told the owners of those businesses that that idea probably wouldn’t work, right? I mean we’ve all heard those stories, so many success stories and so I just told myself that you know, listen, I believe in this idea, I think it’s interesting, I had set myself up to only try it for a year so I said worst thing that happens, I put this out there and no one buys and who’s going to care, right? I’ll just move on with my life and luckily people did start to care and I just kind of trudged forward and said I’m going to make this thing happen because I think it’s interesting.

Success Harbor: So, ‘I Wear Your Shirt’ sounds like a lot of fun but I’m sure there was a lot of learning there. What were the most important things that you have learned during your ‘I Wear Your Shirt’ project?

Jason Sadler: Oh man, lots of things. You know, I think a lot of them, from owning a business, what it’s like to manage people and that’s not one of my strong suits, to things like really realizing, and we all preach this and read this but, quality of content wins over quantity of content and every day I was filming a video, I was putting tweets, I was putting Facebook posts up, putting out a lot of content and the quality wasn’t phenomenal in the beginning and I even go back and watch some of my early videos and I cringe at them but I had to learn, I mean, I had never made a video before so I just kind of jumped in and said, “I’m going to try this and I’m going to try and get better” and so yeah, it was just always a learning process for me and what I kept telling myself every time I put something out there was, “What can I learn from this?” When I put things out there in this way, whether that’s a critical remark or whether that’s a happy photo of me smiling or a video this way or that way and it just–, all these different things. What can I learn from each thing each time and how can I improve upon it and really build something that people want to kind of consume every day? So that’s kind of the lens that I looked at it through.

Success Harbor: So in 2012 and 2013 you took another great idea when you auctioned off your last name to the highest bidders. Where did that idea come from?

Jason Sadler: Yeah, over the years, having the company, I reassured–, we always got–, I say we because there were multiple people who were a part of it over the years, it wasn’t just always me; in the beginning it was but it grew and I was always trying to find ways to get exposure for ‘I Wear Your Shirt’ because when you do something every single day, sometimes people can forget about it and say, “Oh I’ll come back to that because there will always be more”, so I was always trying to get attention and media attention and just get more exposure so I can grow and get more brands to come on board and an unfortunate situation happened in early 2012. My mom called me and said she was getting a divorce and unfortunately that was my third father at the time and so I had this last name now that I no longer wanted which was ‘Sadler’ and I just joked when we were on a call, and just said, “Oh well, you know, I’ve sold my t-shirts, now I’ll sell my last name” and we laughed. And a couple of months later, we were sitting in a meeting with ‘I Wear Your Shirt’ and the people who worked for me and I said you know what, I think I’m going to do this last name thing, like I joked about it but I can’t stop thinking about it, kind of in the way that ‘I Wear Your Shirt’–, I couldn’t stop thinking about that. You know, I’ve built an audience over the years, I think that’s valuable for a brand to be a part of and I couldn’t really find anybody that had done this in a way where they were putting it up for auction and saying like, “Hey, I’ll be your company basically, on paper for the next year”. So I had the website ‘buymylastname’ built, started the auction at $0.0, I built a pre-launch email list of like 600 people, nothing crazy and in the first 24 hours the biding was up over $30,000 and I knew that I was kind of on to something even though I had a lot of doubts along the way and that idea–, I mean, you want to talk about people giving you negative feedback, try to tell people you’re going to sell your last name, that really brings the angry people out of the wood works.

Success Harbor: Give me some examples of negative feedback because I think people need to hear some of that, I mean, you still kept going right? I mean it didn’t really stop you so…

Jason Sadler: Yeah, I mean, there were so many emails and over the years, when you do anything kind of unconventional or different or unique, you’re always going to get people who are jealous or they’re angry at their thing that they can’t do something unique and so they kind of take that out on you and so–, just a lot of messages, especially with the last name thing that this is the ultimate sell-out, you know, how could you do this, you have no soul and these types of things–, and I’d be lying if I said that they didn’t hurt me a little bit but I’m the type of person who, I never got my sense of self from my last name. I mean, I’ve had 3 of them throughout my life right? And most people have 1 last name so it makes sense for them to keep it and they’ll have it forever but that’s not who I am, that’s not how I was raised and what I was grown up with so yeah, it was really interesting for me to kind of hear that feedback and this constant thing of ‘you’re a sell-out’, it’s just so interesting to me because every project that I’ve done whether it’s ‘I Wear Your Shirt’ or selling my last name or my book, which I’m sure we’ll talk about, has involved doing something that I’ve just really enjoyed and I’ve had a lot of fun with and it’s been hard but it’s been something that I control and I really, really like being a part of, doing these projects and the people who I think are sell-outs are ones who take money for stuff that they don’t love doing, right?… which is a lot of who work in jobs in cubicles and no offence if you have a job in a cubicle, but if you’re going to call me a sell-out and yet you sit there and you hate your job and you go home every day wishing you were doing something else, to me that’s selling-out, not selling your last name for a year and then changing it to whatever you want.

Success Harbor: I think–, I mean, I don’t know, I’m not trying to figure out or know what these people think but a lot of times it’s fear that’s speaking I think, you know?

Jason Sadler: Of course, absolutely, I totally agree and I think that I’ve actually turned people who’ve sent me angry emails or angry comments on a blog post or whatever, I’ve turned them into fans, not because I’ve had some magical thing but I just told them, “Hey listen, I understand that this may make you feel a certain way or that you don’t like it but here’s the reason why I’m doing this”, and a lot of times those people, well not a lot, I would say maybe like, a quarter of the time, those people will email me back and say, “You know what Jason, I’m really sorry I said what I said. I was just having a bad day myself and I took it out on you and you are doing something interesting and now that I hear that story, it really makes me understand what you’re doing”.

Success Harbor: Yeah, I mean it worked for Bob Dylan right?

Jason Sadler: Yeah.

Success Harbor: And I thought about changing my name so many times and I would imagine many people thought about changing their last names you know? I don’t understand what’s the big deal about it right? I mean, the paper work is huge right? To do it, so that’s probably the biggest thing about it.

Jason Sadler: Yeah and it’s funny you mentioned that because I had so many people email me–, way more people emailed me that said, “Jason, I can’t believe someone’s actually doing this. I’ve been in this situation for years where I’ve had this last name I don’t want and I haven’t known how to get a new one or what to do with it and you’re making money doing it. This is amazing, I’m so inspired. We’ve so many more of those emails than the ‘you’re a sell-out’ email. I mean, it’s crazy how many people came out of the wood-work that said, “I’m going through something similar, I want to sell my last name” or whatever and there was a small moment when I thought about, kind of brokering people’s last name for brands but then I just decided, I don’t think it would’ve worked for the everyday person and I’m fortunate to have built a following online that I could basically monetized with that sale and get some attachment for it.

Success Harbor: Yeah, I’m surprised you haven’t turned it into a product you know? This is how you change your name, steps 1 to 5 or whatever.

Jason Sadler: Yeah, there’s a ten step process to selling your last name online. Yeah, I guess I could but I kind of know that it only really works for someone who has following, it’s not going to work for everybody.

Success Harbor: Yeah, yeah. And were you still doing ‘I Wear Your Shirt’ in 2012 and 2013?

Jason Sadler: Yeah. So, ‘I Wear Your Shirt’, I officially retired in May of 2013, I stopped wearing shirts after 1437 days or something like that, not that I know the number but yeah… So the ‘buymylastname’ thing was basically a way that I thought we could get some exposure for ‘I Wear Your Shirt’ and it totally worked, I mean when I sold the last name to headsets.com at the end of the first auction for $45,000, I was on Fox & Friends, I was on USA Today, I was on a lot of these news outlets and that brought a lot of brands to ‘I Wear Your Shirt’ saying “Ok, we know we can’t buy your last name but how can we do some fun stuff together?” And so we ended up getting a lot of business from it.

Success Harbor: So then, I mean it sounds like ‘I Wear Your Shirt’ wasn’t an easy project but it was fun and you succeeded with it, you made over a million dollars. Why did you stop it? Did you get burned out? What was the reason?

Jason Sadler: Yeah, just a couple mix of things. I mean, I think that when I started ‘I Wear Your Shirt’ in 2009, I had thoughts of grandeur where I knew I wanted to do the first year and that was going to kind of be my test but in the back of my mind I said, “Alright well, I want to grow this thing to 10 people in the second year and 50 in the third and 1000 in the fourth year or whatever and create this new model for advertising right? This word-of-mouth through t-shirt wearing kind of marketing idea and what I realized was that I was putting all of my chips, if you will, on social media platforms, continuing to let me post all this content in a way that everyone would see it and as social media became more crowded, my messages got diluted. As my company got older, I think people–, they received kind of similar content, if you will, that just–, it wasn’t as exciting to them anymore and so I think there’s a combination of the fact that the idea of ‘I Wear Your Shirt’ lost some of its excitement for me personally and I think for people viewing. I think social media had a big change and when Facebook changes their algorithm and my stuff doesn’t show up, it’s really hard to tell a brand you know, “You’re going to get exposure to these people” when I know deep down it’s not going to happen because the reach isn’t there anymore and so, I started waking up. I had to let people go at one point in 2012, we had bills that weren’t paid in 2011 because clients hadn’t paid on time and that stuff happens when you own a business, everyone knows that and it just started to weigh on me and I took a look at my situation in 2013 and said, “You know what, I’m really unhappy with this and it’s not what it used to be. I doesn’t work the way that it used to. I’m not getting the value out of it at all and I know that the brands that are paying me are not getting the value that they used to get and I got to pull the plug and I have to let go”, and it was a super hard decision because it was basically my baby but if I would’ve kept going I mean, who knows how much worse off I would’ve been, just kind of trying to keep this thing alive.

Success Harbor: I’m amazed by your creativity and even just one, I mean, you had multiple great ideas but you didn’t just come up with one great idea, it’s awesome. How did you develop this skill, is this something that you–, it’s kind of like a muscle that you used to train, I mean, talk about that.

Jason Sadler: Yeah, that’s a good question. I really do think that–, there’s a couple different ways that I think I could answer this question. One is that I think some of us are a built and wired a certain way and I think Gary Vaynerchuk talks about that a lot right? It’s in his DNA to do the things that he does and I feel that it’s in my DNA to do the things that I do right? I mean, create these crazy ideas and make them work and hustle behind the scenes where no one sees all the effort but I make it happen and then I do think it’s also a creative muscle. Like you said I mean, I think that you can–, if everybody just took some time in the day to, kind of what you call ‘woodshedding’, where you go into a woodshed and you sit and you focus and you do one task and you only do that thing and you work on that thing for hours and you become really good at that and I think this is what professional athletes do and this is what the greatest minds of our time do and that they turn off all others things in their life and sometimes that means walking away from family and relationships and other things to become really great at something and I think there’s a happy medium there but you can work that muscle if you turn everything else off and you focus on exercising it and doing different things and so I think creativity is one of those things where we have it within us and some of us, a lot more than others but I think it’s also something where, if people just gave themselves the chance to stay off of social media for a day or a week or a month, not check emails excessively, maybe just once a day for an hour and really focus on learning a skill or practicing something or doing actual work, they would learn wow, I’m going to get so much better at whatever it is that I’m doing because I’m going to not be constantly looking at other things, I’m going to be focusing on this task at hand.

Success Harbor: So let’s talk about Creativity for Sale, your book. You have self-published it, which I really appreciate to be honest, not going through a traditional publisher. Why did you decide to self-publish instead of going–, I’m sure you could’ve published something through a publishing house.

Jason Sadler: Yeah well, I think it was really interesting. In 2013 when I struck down ‘I Wear Your Shirt’ and I was kind of at a low point in life and you know, both personally and professionally I was just trying to find my way and what my thing was, what my next thing I was going to do and I met with a friend of mine and he said, “You know you should write a book, you’ve done some crazy stuff over the years, I think it would be really interesting for people to read your story and you might find that in writing this book, you find your next thing”, and I said alright, yeah, I think I could make that happen so I started reaching out to some author friends and they said, “Yeah Jason, the publishing world is a little bit messed up these days, you know big publishers – it’s kind of hard to get in with them. You’re not going to make any money up front with the book. If you do get an advance, it’s basically a loan and you have to sell a certain amount of books to actually get that money back”, and I started looking into all this stuff and I had a lot of people tell me, publishers are going to change your story. They’re going to write it the way that they want it, they’re going to pick the book cover that they want, they’re going to have all the say and I just–, all that stuff just made me throw my hands up and go, “No way”, like I’m not doing that George so I basically…

Success Harbor: Plus it takes about 2 years right? To publish the book, at least.

Jason Sadler: Yeah, the process is really slow and for some, I think some publishers are probably way faster than others and again, I haven’t had any first-hand experience, I’m just going off what friends who work with publishers have told me. But I just wanted to control everything, I’m a control freak. You know? I’ve run my businesses the way I’ve wanted to run them and I knew that about myself and that it would drive me nuts if someone told me I couldn’t put a story about how I met my girlfriend in my book, right? If they’d be like, “Oh, this doesn’t matter to the story that you’re telling, I would freak out so…

Success Harbor: It’s almost like you’d become an employee instead of an entrepreneur and controlling your own destiny.

Jason Sadler: Exactly, right? I mean, someone else is the gate keeper to the information that you want to put out in the world and my friend Clay, he talks about gate-keepers a lot and I kind of get that from him and so when I started to put the idea of the book together more as I thought about it, I said, “Alright well how can I make money with a book. Right? What’s something that someone hasn’t done and then what’s also something that I have done where these things can kind of meet in the middle?” And so I looked at sponsorships, you know? I’ve done the sponsored t-shirts, I’ve done the sponsored last name, I’ve never seen a book with sponsorships on it and since–, you know, where it is now, I’ve heard from a couple of people who people have tried this. They’ve done sponsored chapters or a couple different things but I had the sponsorship on all 200 pages of the book. Its 140 character message, there’s no logo, there’s no QR code, it’s just a very simple, basically footnote style message and so, I sold those pages, along with the 4 covers of the book, the 2 outside covers and the 2 inside flaps and made over $75,000 in 5 months selling these sponsorships in the book and that’s a book advance right? I mean, that’s basically money that I made before a single copy of the book was sold, before a single word of the book was written. That was basically just companies and people opting in and saying, “Jason I’ve seen what you’ve done over the years, I believe you’re going to write a good book, I want my brand to be a part of it”.
Success Harbor: And ideally every book should be done like that or every business should be done like that right? I mean, sell it and see if people are going to pay for it before you even invest anymore time or create a product right? I think its genius.

Jason Sadler: This is very much like the lean start-up method…

Success Harbor: Exactly.

Jason Sadler: Yeah there’s a lot of–, prove that something’s going to be of value or worth and that someone will pay for it before you do it and I would be lying if I said it was easy; I mean I didn’t just send out an email and the book filled up, you know? Through email…

Success Harbor: How many months did it take you to actually come up, to sell the $75,000?

Jason Sadler: Five months.

Success Harbor: Five months?

Jason Sadler: Yeah, and I sent out multiple emails to my lists and I responded to a lot of emails from people who came to the website and I had a lot of phone calls to people and so it took quite a bit of time to make this book happen but it was worth it right? I mean because again, the day that that sponsorship–, and the last one that sold is funny enough, was the front cover sponsorship to tree house and when that sponsorship sold I basically had a huge sigh of relief and said, “I did this, I mean I made this thing happen. Now it’s time to get to work to actually write the book that everybody wants to have their name in.”

Success Harbor: And for the audience most books don’t ever make $75,000, I’m talking about books that go through publishing houses right? I mean, most of them sell less than 5000 copies and make peanuts so your book was more successful even before it was published than most books out there that got published.

Jason Sadler: And yeah it’s a great point that you bring up because I’ve read 30 blog posts on how to make your book a best seller on Amazon and the New York Times Best Seller and as a self-publisher you can’t even get on the New York Times Best Seller list I just learned so there goes that, accolade that everybody wants as an author but yeah I mean these people hustle and have all these systems and gimmicks and tricks an all these hacks that they do to reach these lists and you’re right, most of them don’t even make $75,000 even when they get to be a Best Seller on Amazon. Maybe they’re making a couple thousand bucks a month but it kind of tails off after a while and again Amazon controls what book show up where, right? And so, they’re like another gate keeper in this world of where social media changes their algorithms; we’ve heard about this with the Amazon and the big publishers that there’s some kind of head-butting going on there and again I don’t want to be in the middle of that. I want to be able to say I’ve got lists of people, I’ve got outreach, I’ve got things I can do, I can hustle, I can make this thing happen on my own and I don’t need an Amazon or anybody else to help me make that successful or profitable.

Success Harbor: So I don’t want to put you on the spot but is there may be an action item from ‘Creativity for Sale’ for entrepreneurs that they can take? Maybe just one idea, I mean they should go out and read your book but is there something that they could take action on?

Jason Sadler: Yeah, I think that one of the big messages for me in the book; and we’ve heard this before, is ‘the harder you work, the luckier you get’, and I think that there’s a very simple math equation to having a successful business where we are in life right now and that is ‘Effort equals Success’, right? And the more effort you put in and the more work that you do and that doesn’t mean checking social media and email and signing up for the newest thing that comes up, that means actually putting in work and honing a skill and becoming better at something and creating content and putting that out into the world and you’re going to have success if you get better at that and you work at that and you really do that and that process is something where people don’t–, they don’t want to put in the hard work. Right? They want ‘what’s the fastest way I can make money’ and not have to put in any effort and those things they really just don’t exist, it’s a lot of bluff and it’s a lot of fake things that are out there and I know that as people have read my book. I’ve gotten a lot of great emails from people, I’ve been so happy to read these emails that people are like, “Man, I had no idea how much work you put into the things you did and it really made me think. I thought it was just easy for you all these years, now I know how hard you had to work and it makes me want to work hard at the thing I’m doing.”

Success Harbor: Yeah you wrote on your blog; ‘2013 was a rough year for me, I went through some of my lowest lows and did some heavy soul-searching’. Can you share what those lows were?

Jason Sadler: Yeah.

Success Harbor: … because you had a lot of success so people think everything is rosy and it’s only fun times and a lot of laughs but can you talk about some of the lows and how did it change you or how did it change your perspective going through all that?

Jason Sadler: Yeah, I mean earlier on in 2013 there was a point where I had to pay salaries for two employees and myself included and I had $92 in my bank account and I had credit card debt and I had basically nothing in sight that said I was going to make enough money for the next month to be able to pay these people and that was probably one of the hardest things to deal with; is to know that people rely on you and that you can’t provide for them because number one, I had lost some of the desire to keep the business going but also that it just wasn’t working anymore and so personally, that takes a big toll on you and I think that I really just got caught up in a lot of the media hype for the stuff that I did over the years and I kept hearing those stories and reading those things and so you kind of build yourself up in your own mind and you compare yourself to the previous more successful version of yourself and it just wasn’t the same anymore and so I just had to take a step back and I went to this conference in Fargo, North Dakota in May of 2013 called ‘Misfit Con’ and I heard from people who were fellow entrepreneurs and people who had been through stuff and this guy, Joshua Fields Millburn, who’s of ‘theminimalists.com’ and he talked about how he had racked up this debt and the more money that he made, he realized the more money he was spending and I was in that same frame of mind and I had to change that stuff and so I just started to peel back the layers and just share not the intimate details of my bank account, but to say I’m not happy with where I am; I’ve been too prideful, I’ve been thinking I’ve been really successful and I was early on but I haven’t had that same success now and everything looks great but it’s not and I need help, I need to figure out how to get out of this. So it was really tough the share that stuff and to put that stuff out there but it was also great at the same time to help me kind of grow as a person.

Success Harbor: Ok. Let’s talk about dealing with the roller coaster ride of the ups and downs – one day you feel like you walk on water, the next day you feel like an idiot. Has it become easier? I mean, I know I go through that as an entrepreneur but my question I guess, is why do you think there isn’t more sharing about the downs of entrepreneurship? I mean, when you read about entrepreneurs it’s always about how somebody sold a business or exited a billion dollars and I know maybe that’s the story people want to hear but I wish there was more interest with the downs and failures from people because I think that’s really what makes business work.

Jason Sadler: Right, I think Chris Boone said it best and I wish I would have said this before him but he beat me to it is that, “No one wants to see your before pictures”, and when you talk about like–, we see these fitness photos online all the time of like this before photo and this after photo and like how amazing this person looks afterwards and that’s what the media does with entrepreneurship, is they talk about the Instagrams making a billion dollars and the WhatsApp’s making this money and Facebook going IPO and all this stuff and they don’t talk about alright well, what happened like a year ago to those people and why was there no article written about when they were a couple hundred thousand dollars in debt and it looked like they were going to have to close their doors, where were you when they were going through that and why weren’t you sharing that story and it’s just because unfortunately George people don’t want to read that stuff. You and I would appreciate it because we could relate to it and it’s something that like we could learn from and maybe we could get some value from but the media and kind of people reading all of this stuff; they don’t want that stuff, they want the great success stories and I think that’s a lot of just kind of our American culture that dictates that and that’s what we strive for and so I’ve tried to just be way more real and relatable with my content and I know that I write for some publications and I try to make sure that the stuff that I’m putting out there is not just the ‘here’s the perfect path to success stuff’ anymore because it’s not perfect and it’s not all rosy like you said and I think more of that stuff does need to put out there and I’m not sure if that shift is going to continue with other people because I think unfortunately the things that get the page views and get the ad dollars spent on them are the big success stories.

Success Harbor: You know because it’s so interesting that we have all these ‘how to write a title’ that it’s going to grab attention and those titles; they all look the same, they’re exciting and boring at the same time. The 7 ways of this and the 5 secrets of that and the 10 tips to do this and it’s something that I’ve been thinking about for a while. Tell me what was the best advice that you have ever received?

Jason Sadler: My buddy Shane Mack was really helpful last year when I was kind of through my low times and he was out in San Francisco and he’s had a couple successful start-ups he’s been a part of, and has a new one called ‘Skedaddle’, that’s really cool and he basically just told me, “Just ask”. Just those two simple words just ask and I kind of turned that into my life motto which is ‘you don’t get what you don’t ask for’ and that’s whether that’s a big client for your business; whether that’s someone to help you do your thing but the thing that’s been really helpful for me is to just not think I can do everything myself and to realize that there are a lot of people who are out there, family included who’ve been through a lot of this stuff and have experienced a lot of these things and if you just ask them for their help and support they can really help you get through years of struggle because they can say, “Hey, here’s how to avoid this” or “Here’s what this is going to feel like, you probably want to do the opposite.”

Success Harbor: What do you think is the biggest time-waster for entrepreneurs?

Jason Sadler: Social media, and it’s funny because I’ve built my living on social media and I built my name on social media but the value of social media has plummeted, I mean there’s really almost no value because of the way that we interact with these networks. If you look at anybody on their phone looking at twitter or Facebook their finger is scrolling at a speed that could start a fire, right? I mean, it’s so fast and how is your message going to resonate or do that and why do you need to read so much of that stuff. We’re literally dumbing ourselves down because we’re over consuming all this information and I think that there are so many talented entrepreneurs out there who focus on just consuming all day long instead of creating and you can lean so much more from creating when you came from learning all the ‘7 tips’ blog posts and the ‘4 ways to do these things’ and I think that social media is so great in so many ways but it’s also so hurtful in so many ways because of how much time we spend and how much effort we put into consuming all that content.

Success Harbor: So you have had a lot of success in business and let’s say you have a friend or a family member that has a job now and want to become an entrepreneur, what would be the first thing that you would teach that person if they came to you for help?

Jason Sadler: I think, one of the things; I talked about this in my book, is you’ve got to find the thing–, and Simon Sinek says this, like what’s your why? You have to find the thing that gets you up in the morning out of bed and like you’re just so excited to work on whatever that thing is. I’m really excited to talk to entrepreneurs who come to me for consulting or whatever and they’re just so fired up about their idea but they’re not sure how to put the puzzle pieces together for it right, and I think that’s the start; you have to have that foundation that, don’t just go into an idea and do it because someone else made money doing that and you think you could do that but go into it because it’s something that you can poor all your effort into and you’ll be really excited about and then start building. And again like we talked about earlier I think ‘The Lean Start Up’ is probably one of the most boring books I’ve read in the past year but it’s also probably one of the best because it really shows you kind of this new model for selling things especially in the internet age of, ‘if people don’t buy it you’re going to take a step back and look at why people aren’t buying it’, don’t just keep trying to push it and get more people to look at it thinking that, “Oh well, it just needs more people to see it for people to buy it”. No, there’s a reason why if you show it to 10 people and none of them want to buy it, you’re missing out on some opportunities there so I think those are a couple of places I would start.

Success Harbor: I want to ask just one question about my business ‘Success Harbor’, what do you think would help make it a little bit different from other sites that interview entrepreneurs because I love doing it but at the same time I create all this unique content interviewing entrepreneurs but I want to have a twist. I want to have something, you know, well Success Harbor’s a little bit different. How do you think I should think about my business to have more creativity and maybe to come up with a different angle based on your business experience?

Jason Sadler: Yeah I mean I think for, especially people doing interview series and stuff I mean, no offense to Success Harbor but there’s an interview series out there for entrepreneurs from many people right?

Success Harbor: Yeah, exactly.

Jason Sadler: I think you need to find what it is that really excites you about talking to entrepreneurs and what you can really pull out of them that other people aren’t pulling. I think you’ve asked some great questions today and I think some of the best interviews that I’ve done are when people do–, they don’t just have a scripted list of questions and they segue into each one differently but it’s when they really try to dive deeper and figure out like what’s making this entrepreneur tick that people can take away from that and to me I think that’s where some people are having the most success with podcasting or interviewing or any of these things. So yeah I would just challenge you to say like what’s the thing that you can do or the way that you can interview someone that’s interesting or different or unique that it’s not just asking questions about what they’ve done but it’s really like diving into what’s makes them tick or maybe it’s something completely separate, maybe it’s with every entrepreneur you talk to you want to figure out what’s their lifestyle and how can people adapt that lifestyle to their lives. I think its finding that little sweet spot of the thing that you can really pull out of people.

Success Harbor: That’s great, that’s great. Jason I want to thank you for coming on Success Harbor today. I’m so stoked that you shared your story because so many people see–, I remember years ago I saw an interview with you and I thought you know this guy is a genius and everything is great and that’s never the story. You can look at any business; any successful business and it’s not all rosy and it’s not perfect so I think people need to hear that, that even if you have success there’s a lot of struggles and I’m so excited that you shared it. How can people find out more about ‘Creativity for Sale’ or connect with you or find out more about you?

Jason Sadler: Yeah, I would love people to grab the book, you know, ‘Shameless Plug’, find ‘Creativity for Sale’ on Amazon and grab it on Kindle or Paperback and then also I’ve got a little catch-all website called ‘jasondoesstuff.com’ because that’s what I do, I do stuff so that has all my social media links and email if people want to reach out and I would love to hear from some of the Success Harbor listeners who just want to learn more about my story and maybe what they’re doing and what they’re up to so yeah ‘jasondoesstuff.com’ and find the book on Amazon.

Success Harbor: So everyone out there, check out ‘Creativity for Sale’, Jason is somebody that actually did all that, there’s a lot of people who write a lot of books but Jason is actually somebody that has done all that so I think his story is awesome so check it out. Jason thank you very much for coming on.

Jason Sadler: Thanks for having me George.

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