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“Straight white male, Women’s Studies major. Doesn’t happen a lot.”

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Mike: Hey everyone. I’m Mike Sullivan. Thanks for joining me today on MO.com. With me today is David Siteman Garland. I’m very excited to have David here. You may know him as the host of The Rise to the Top. If you don’t, David hosts a show online that interviews successful entrepreneurs, typically internet entrepreneurs. He pulls out some great information and there’s a lot of learning that can take place.

David, thanks a lot for being with me here today and I just want to start out by asking you how did you get your start with this? How did you come across interviewing entrepreneurs and putting this online?

David: Yeah, you know, it’s actually a crazy story because I don’t really have a background in any of this, whatever we want to call this, meaning broadcasting or anything like that. And where the idea came from was, after graduating college and having no idea what I wanted to do in 2006. I went to Wash U and was a Women’s Studies major, of all random things that you could possible imagine. Straight white male, Women’s Studies major. Doesn’t happen a lot.

I am very passionate about hockey. That was something that I loved and for two years, I was involved in a hockey kind of startup company in St. Louis called Professional Inline Hockey. And that was sort of how I got the entrepreneurial bug, if you will. And I just loved it. And after two years, I decided to move on and as sort of byproduct of Pro Inline Hockey, was I ended up with a radio show, which is a whole ‘nother story, on a local station in St. Louis where I was doing a Pro Inline Hockey show. And they basically threw me on this thing, no idea what I’m doing and I started really enjoying it, especially interviews. Having hockey players on and coaches and stuff like that. And I was like God, this is really, really fun. And so fast forward it to 2008, and I was sitting there and I was thinking to myself, wouldn’t it be cool to create a TV show, at the time, and it has evolved a lot since then, centered around sort of younger, hipper cooler entrepreneurship, as opposed to like the old stodgy stuff we see all the time on TV.

And so the Rise to the Top was an idea that really came up at a coffee shop. I was staying with a graphic designer friend of mine and I said we should create a TV show and I can host it and it’ll be about young entrepreneurship. And that’s how it literally started, as an idea for a TV show more than a website or anything like that and how it’s evolved since then. And that was in 2008, really from complete scratch. That’s where the idea came from.

David Siteman Garland, The Rise to the Top - Founder & Host

Mike: One of the things I want to ask you about is your viewership. A lot of people have blogs or sites online. You have developed quite the following in just a few years. I think you had over 250,000 followers in like a three year period. How did you accomplish that? What are some of the tactics you used to get to where you’re at today?

David: It’s evolved. There were a few different moments. So now coming up on a few years later and we’ve got about 250,000 people that tune in a month to the show, which is just outrageous and I still don’t believe it. But that’s what I’m told. So what happened was, I did a couple years of local television where it was just, that was a whole ‘nother thing, but I learned to do stuff online and build the audience really on social media and through the internet.

The show now is all completely shot through Skype video. We do it kind of very ghetto, underground style in how we do it and the show really focuses now on people that are making money online. That’s really the entrepreneurial focus that we have. But to build the audience, there’s a few different things that I did from the beginning and realize I didn’t have any budget whatsoever. I didn’t have any contacts. I didn’t have any budget. This was not started from some kind of magical place where we could throw a lot of money at it or something like that or I knew a million people. I really didn’t.

So the first thing that I did was I said well, how can we start locally. This is how I did it at the very, very beginning. I said how can we start locally because it was a local thing before now being international. And I said well, ok. First of all, I need to get my butt out to events and start meeting people. So any kind of random local business event, even if it was terrible, which most of them were, I would go out there, shake hands, meet people, kind of introduce them to the show. I would go to pitch fests and things like that, where people would get onstage and pitch a new idea that they had, just to get some exposure for it.

I started doing that locally and also sort of focusing on local media. So St. Louis Magazine and a few different other things that were local. I started saying hey, there’s this young guy, well it’s me, this young guy who’s starting this TV show and it’s about entrepreneurship and this kind of thing. I was pitching stories like that and I also went about sort of an event series where I started inviting local smaller, especially entrepreneurs out to do a dinner. We called it dinner and discussions. We had a little programming and stuff like that. It ended up running about 36 events over the first couple of years. Not as money makers, in fact, I think I might have lost or broke even at best, but really just kind of get people out, get people interested and have that face to face time.

So that was all like sort of the offline thing and as the brand started to build, people started asking me for speaking opportunities and those types of things. That kind of evolved from there. But online, which is always my favorite place besides a face to face, of course, is I really got in the deep, deep trenches of social media and blogging. So what I mean by that is I was connecting to anyone that I thought was interesting. I would invite them for an interview on the show. I would just be networking my butt off online. I would find other blogs and websites that were similar to my niche and then start talking to those people, getting involved. Posting on their site. Not being a jerk and saying hey, come watch my show but just getting involved and getting to know these people. And the number one thing that I did, Mike, and this was called a dirty trick but it really wasn’t at all, was that if there was someone that I really wanted to know and get to know them, I would invite them on for an interview on the show. Especially when we started to do invite through Skype video. So I would reach out to people and say hey, you know, I really love your blog about entrepreneurship. Maybe we could discuss how you started it and these different things. Why don’t you come on the show. And a lot of people wanted to come on and that started to build solid relationships with influencers, up and coming influencers, and “important” people in the niche. But I really became friends with them.

It wasn’t about like hey, can you come on the show and now can you do all these things for me or something like that. That wasn’t the case. And so that’s it. Getting in the trenches, working on Facebook and Twitter especially were my favorite places to be and just constantly engaging. Responding to every email and just growing it from there. And one more tactic is I could talk about this marketing stuff all day because I think it’s so important because people start something and then they have trouble with this.

Guest blogging was a critical thing early on too. Once I found sites that would offer guest blogs, and I say the keyword offer guest blogs Mike, because here’s what happens. People come to me all the time. I don’t do guest blogging, for example. Let me write a guest blog. And I don’t want to be a jerk and say listen, we have like 8,000 posts up. There’s not one guest blog. Do you know what I’m saying? There’s plenty of sites that do guest blogs and I’m all for it but we don’t. So I would identify places that did, you know, small business trends. There was Hub Spots Internet Marketing Blog. Personal branding blog. All these ones that I really liked and I said I could offer something interesting. Maybe it’s from an interview I’ve done or something that I’ve done with my brand. Let’s do a guest post. Link back. And that was one of the critical things that helped build it early on and it kind of spirals from there. But that’s just a few of the things.

Mike: You’ve interviewed a lot of successful entrepreneurs and I know from my own interviewing experience, each interview is like a mentoring session. You pick up something. You learn something. You’ve interviewed people like Gary Benercheck (sp) and Tim Farris are a couple that jump out at me. What have you learned in these interviews? What are some things that have stuck with you that you’ve taken away?

David: God, you know, that’s such a great question and so much, because the reason that I do this is because not only do I want to help other people learn from the show and it’s kind of, I call it edu-tainment, so education and hopefully laughing and learning along. But also, it’s a huge tool for me of learning and absorbing these things because I have on people that I find personally interesting, bar none, and I try to learn from them. So I’ve learned a lot of different things from different people and it’s almost like by person that it’s all a little bit different. But Gary, one of the critical things that I learned from Gary is that listen, if you’re going to create a media platform online, on those internets, and you’re creating your blog, your creating your show, whatever you’re going to be, you have to get your butt into the trenches and start building those relationships the rest of the day, especially when you’re starting.

What I mean by that is getting in there in the forums and the other blogs, connecting with people. He just got into that whole you’ve got to get on there and you’ve got to go step by step every single audience member and person that becomes a fan is important and you’re going to have to do it individually to begin with. And a lot of people don’t want to put in that work of spending hours on Twitter and talking to people or hours on Facebook talking to people or answering every email or answering every comment. I really learned about engagement from Gary Benercheck and people complained about that. They would say Gary, you’re out of your mind. You can’t do that. I can’t do that. And I can tell you right now, he is so spot on with that, it is unbelievable.

The other side of the spectrum, just because you mentioned these two people, it’s like I could learn a lesson from 300 plus guests. Let’s use the two that you mentioned. Tim Farris, I think speaks for two different things that I thought were very, very important. Number one is taking massive pride in the products that you create for people and what I mean by that, his case was a book. Four Hour Workweek, Four Hour Body, things like that. Too many people, especially on the internet, kind of slap a product together, throw a price tag on it, get it out there and market and promote it. And they forget about that core which a lot of people say is putting the most effort into the product. And Tim is a case site. He’s a tireless worker of the way that he goes about creating his products. He doesn’t put it out there, I don’t want to say perfect because nothing is ever perfect, but he makes sure that nothing behind his name sucks when it goes out there. He’s going to make sure it’s the full effort.

And the other thing that I learned from Tim and I think this was a critical lesson, especially a few years ago and it still applies now, that when you’re looking to kind of get the word out, build relationships about something that you’re building, whether it’s a product, a service, a company, whatever it may be, that I got to be honest and I agree with this 100%. The most important people and the trickiest to deal with are online media sources. What I mean by that is bloggers, show hosts, podcasters, stuff like that. If someone says listen, I have this amount of time to put my effort into something. Should I focus on traditional media like these things behind me here that are up on the wall that look real cool or should I focus more on blogging and online media, the answer almost for everything is number two right now. It’s just the bottom line is focusing on the bloggers and online media. And that’s how his stuff became best sellers and that has trickled down to a lot of other people as well.

Mike: And not only are you on online personality, but you’re also an author. Do you want to tell us a little bit about your book?

David: Yeah, it was a very interesting experience. I’m always very transparent about this kind of stuff. So my book called Smarter, Faster, Cheaper. I always have copies floating around here. It came out in December 2010. And here’s a few different interesting things from this. Number one is the book deal came to me. I didn’t go for the book deal, which was kind of interesting, was that I interviewed a lot of authors on my show and unbeknownst to me, they were sharing this with their publicist. Like hey, I was on this show, check it out. Here’s the interview. And the publishing house, Wiley Publishing, came to me and said hey, would you like to do a book? And I said sure, let’s do that. So we put a deal together. It was a lot of fun. It was a great learning experience because putting a book together is very challenging. I like writing. I prefer to talk but Smarter, Faster, Cheaper did very, very well and also taught me that, for my next thing that I’m doing, which is teaching other people to create interview type shows and their own kind of web talk shows which is something I get just unlimited questions on, that I really like the book. It’s helped a lot of people.

And then I want to get more specific from there because the book was kind of designed for solo entrepreneurs and people that are like how can I build an audience and how can I build a fan base and kind of do the things that you did with the Rise to the Top with my company? And what I started realizing is that a book was great. It’s a great primer for people to kind of understand this world of, that you don’t need a ton of money to do these kind of things and you can really kind of hustle and get in the trenches and now I’m looking to bring that even more specifically to the talk show focus. Of teaching people how to do their own kind of Smarter, Faster, Cheaper talk show online. And that’s kind of the focus where I’m going now in 2012 here.

Mike: There are a lot of online businesses out there, blogs and other types of sites that depend on advertising for their revenue. You seem to have been pretty successful in that area. What tips or what’s the secret? How do you attract sponsors or advertisers to support the site?

David: We can hop into this. Let me tell, first of all let’s get a little backstory on this and realize my business model went from doing it a local TV show, an online show, an event series in 2008. Same thing similar in 2009. Then we went basically all online show, 2010, 2011, 2012 and dropped the event series. So there was kind of an evolution. The first year or so, I think I want to say I lost a little bit of money, broke around even. Second year, or somewhere into the second, somewhere around there, we started turning a profit. Year three, so somewhere around 2009, 2010, I want to say 2010, started turning a six figure profit, which is not that long. Let’s be honest. By any means. So what happened and kind of what was the path here, sponsorships are a tricky game.

I do not want to sit here and BS and say here’s how easy sponsorships are. I have learned so much over the last few years and I’ve got to tell you, it might not even be the best model but let me explain what I did. So first and foremost, when I had the local TV show, that was a different thing because we sort of had a built in audience because you had a station, right? So what I did was I pitched the TV show, the event series, and the online show of mystery, we didn’t even know what that was going to be, to people I’d built up relationships with locally through Pro Inline Hockey. That’s how I got started.

So I knew them through Pro Inline Hockey, because I was doing sponsorships there for a couple of years. Came back and said hey, we’re doing entrepreneurship. We have some local TV time that I just bought. I just bought the local TV time and put our own show together and then had sponsorship. So it was kind of like if you were to buy an infomercial but instead of putting an infomercial on, you put a show on. So that was kind of the idea.

So I went to local people, started working with that and my first problem that I had was trying to get enough money. So first year we were about even. We had people buy in because I think people buy into excitement and I think people also buy into organization. We had very nice branding done. We had very nice a logo and a look and we could show people what it was like and that makes a difference. Too many people don’t have that stuff organized and they go to people and they’re like yeah, you kind of look like amateur hour. And so we were able to get some pretty decent sponsors early on.

Then I got into a problem of saying well, I can’t do this all myself. It’s outrageous. Getting us sponsors, doing the show, all these different things. So I hired a local company here and we just basically created a revenue share. They would go out and sell the sponsorships. They’d get a percentage. I’d get a percentage. We’d put it up online and on the show and yadda yadda yadda. Sounds awesome. Terrible. Here’s way. Number one, financially it was decent. That was the first time we started to turn a profit. The problem was, it was not a great fit with our audience. They were finding sponsors that were people that they had existing relationships with that just weren’t great for our audience. Like a car dealership and things like that. It just wasn’t the greatest fit.

And so what I learned from that one is that the most time you should spend, if you’re considering sponsorships is number one, building your audience. Too many people are like I want to start a show tomorrow or a blog and then I want to get sponsorship. Let’s not put the cart before the horse. Number two, spend a lot of time quantifying. Who are people that are going to spend money in your space online? Online. Not in general because I wasted too much time pitching people that either a, didn’t advertise. That was ridiculous. So wasting my time talking to people that you have to go and educate people why to advertise or sponsor something when you might not even 100% agree that they need to do it. It’s stupid.

Second of all, then I would waste time with people that didn’t quite understand online media. So you’re trying to explain well, you should bring your advertising from your print magazine that you’re doing right here. Why don’t we do this online for one tenth of the cost of doing this. You’re wasting your time, especially if you’re a small entrepreneur. You’re not going to have time to be going in there and changing the education of a company that’s been around for like 30 years or whatever it may be.

So what I learned to do was to really pay attention to who was spending money to reach the same people that I have in my audience online. Online or at events that these people go to offline. And so that’s how I identified, for example, Hub Spot which was one of my big sponsors for a year. And I saw that they were doing a lot of things online and I saw how they blog and that they understand this. I had interviewed a couple of people from Hub Spot on my show. We had a relationship there. And I approached them and I said I have this idea. It might make sense. It might not but here’s the deal. At the time, we had about 50,000 to 75,000 people tuning in a month and the Hub Spot sponsorship, I want to say was about, now I’ve got to look back on the numbers on it, but a little bit less than six figures, but just for that one.

So there’s a baseline audience that you have to have there. But I spent so much time quantifying it and also offering something that other advertisers or sponsorships couldn’t do because we do a lot of personal touches through the show. I do personal plugs of the products because I only promote things that I believe in. I learned my lesson. I only promote things that I believe in and I use. Now Citrix Online is our biggest sponsor. It’s a tricky game to say the least. And a lot of people ask me what’s the minimum audience to have a sponsor? How do we get started with sponsorship?

I can’t answer that necessarily because it’s different for every single time. I can tell you, let’s get to 10,000 fans. Let’s get you to 10,000. Maybe not passionate fans that are like tattooing stuff on their face for you, but let’s get to 10,000 that are tuning in a month and then let’s approach it from there. But what I’m learning now, especially as moving forward, I think it’s best for content creators to control their own destiny when it comes to the economics of their company and you’re not going to be able to do that through sponsorships, because you’re still going to be dependent on other people giving you money. And so what I’m seeing now, and this is where I’m going, and I’m not saying we’re going to nix sponsorships by any means. It’s just going to be one of the buckets that’s going on.

But the way that I see this going in the future, and this isn’t just me, this is other people as well. Number one, is creating your own products and services. And a lot of people have this already. But really focusing on that, whether it’s an online course, a membership site, whatever it may be. Your own products and services and using your show as a tool to kind of bring people in and get involved in that. The other thing is also kind of leveraging into other opportunities you might want to do, whether it’s get a book deal, speaking, consulting, different things like that. That’s a huge opportunity there. And the third thing that I’m seeing is either a hybrid model or completely charging for your content.

Mxyergy.com, good friend of mine, what he does is that the interviews go up. They’re free for one week. They’re free. Everyone else gets funneled to a membership model. You pay a certain amount per month and you get all the archives and then you also get weekly courses that he puts together with an expert to teach something specific. And I think his model is brilliant and I’m not one to say here’s the theory, because I know people that are doing it well, but I see this is in the future as thinking of other ways to monetize besides sponsorships. I can tell you right now, if you gave me the same amount of money, Mike, and you said here’s, I’m going to make up a number, $500,000 and you have a choice. Your choice can be either $500,000 coming from sponsorships, $500,000 coming from revenue from online products and maybe a membership or something like that, I would take that one every time into the future. So that’s my advice. My advice on my 20 minute story here on sponsorships or whatever, or however long it was. My advice is not to do it. Not really, but you get the idea.

Mike: What’s next on the horizon for you?

David: I’ve got to say, I’ve avoided this for way too long. I’ve just got to be honest. It’s one of those things where I’ve been so focused on sponsorships because it started to work a little bit that I spent so much time on that and people kept coming to me and let me tell you a light bulb moment. I was MCing Shine, which is a big entrepreneurship event for women. I was the male MC with 600 women in Dallas, Texas this past November. Ally Brown puts it on. Outrageously cool event and I was there and I met, in person for the first time, a lady named Debbie who is a huge fan of the Rise to the Top. We’ve talked via email. She sent me a present once out of nowhere. She sent me some wine. Thank you, Debbie. But just a huge fan and she comes up to me and she says David, I need to buy something from you. And I was like Debbie, I got nothing to sell you my friend. I have nothing to sell you Debbie. And she said no. I watch your show. I listen to the show. You need to create a product because, I’m telling you, I get all excited about your guests. I go get their products and that’s awesome. By the way, that’s another great way to make a little side income, is that you disclose it but you do affiliates with your guests. So if you have something to promote with a guest, you just say hey, by the way, my affiliate links below. Check it out. And that’s a great way to earn. Now it pays for more than my mortgage a month, doing that.

So she says you need to create something and I want you to think about that. So I came home and I started polling the audience, polling my community. Sending out surveys and then I started looking at past emails. When people email you, was there a trend? What were they asking about? Was it the same thing over and over again? And so I started looking at this kind of data and I realized holy shenanigans, there’s a subset here of passionate people, not everyone. I’m not trying to sell to everyone because I’m trying to create something that will help out a very specific part of the audience. But I realized that there was a passionate subset that wanted to create sort of their own talk show. They wanted to create their own Rise to the Top and they wanted to learn about all these things that we kind of discussed but in detail. Like how do they create their brand? How do they land major guests? How do they monetize? How do they do these different things so that they can create their own version of the Rise to the Top?

And that’s where the idea for Create Awesome Interviews came from, was to take my entire system on creating and promoting and profiting from interviews and teaching it, with myself teaching every single thing I know. Showing video tutorials of everything that I do behind the scenes as well, all the equipment, because it doesn’t take a tech master to do any of this stuff. And then, also bringing on about six of my top interviewee friends that do the same thing to kind of teach parts of their methods as well. So we put it together. It’s called Create Awesome Interviews, which you can check out at CreateAwesomeInterviews.com and that is really my first venture into this big digital product. But I can tell you, as soon as I announced it, boom. We had a passionate subset of people that have signed up. They’re involved and they’re very, very excited about is. So I feel like I got over that fear of packaging something together and getting it out there. And I’m just kind of very, very pumped about it.

Mike: Hey David, great talking to you. Thanks for your time. I swear I could talk to you all day about this stuff. Take care. Bye.

David: All right, Mike. My pleasure, man.

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