Software by Rob: Lessons Learned By A Solo Entrepreneur – with Rob Walling

How does a developer quit his job and build a profitable collection of web sites?

Rob Walling owns a collection of small startups, including HitTail, which guarantees that its customers will increase their organic search traffic, and dot net invoice, which helps you create your first invoice in 3 minutes.

He blogs about how he built his companies and what he learns at SoftwareByRob.com. I invited him to tell you his story.

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Rob Walling, HitTail

Rob Walling owns a collection of small startups, including HitTail, which guarantees that its customers will increase their organic search traffic, and dot net invoice, which helps you create your first invoice in 3 minutes.

 

Raw transcript

Mixergy's audio transcription is done by Speechpad

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Hey there freedom fighters, my name is Andrew Warner. I’m the founder of Mixergy.com. Home of the ambitious upstart, where 700 entrepreneurs have come on to tell you their stories, so that you can learn from them. Build your success story, and then come back here and hopefully do what today’s guest is doing. Come tell your story and teach others. And, I like to focus these interviews, and this one’s a little bit tough, because the person that I’m about to introduce has done is so much. I’ll just go with this as an intro, how does a developer quit his job and build a profitable collection of websites?

Rob Walling owns a collection of small start-ups, including, Hit Pail, which guarantees it’s customers that they’ll increase their organic search traffic, and Dot Net Invoice, which helps you create your first invoice in three minutes. He blogs about how he built his companies and what he’s learned along the way, at Software by Rob.com, which many software developers and micro-entrepreneurs, and even macro huge entrepreneurs read, including me. I invited him here to tell his story. And frankly, the first time I did he said no, he was too busy building one of his sites, and I finally got him to say yes, and Rob I’m glad you’re here. Thank you for doing this interview with me.

Rob: Thanks for having me. I’m a big fan of the show.

Andrew: So, you weren’t happy when you were a developer, when you were working as a consultant. Can you tell us about that?

Rob: Yeah. I view consulting and salaried work, it just always felt like a hamster wheel to me. It felt like something I was never going get away from. I was always looking for ways to, thinking about when I’m 50 years old, am I going to be doing this? Am I going to still be managing websites for clients that are unhappy?

Andrew: Mm-hmm.

Rob: Actually, I remember having a client who called me, and me and another guy were set up to maintain his website, and they were a pretty big e-commerce site. It was during Christmas and it started to crash. It was actually a really crappy code and it was on a crappy server, because the previous developer had set it up that wasn’t affiliated with us. And, I picked up the phone and this guy yelled so loudly, that I had to hold the phone away from my ear, like it was a cartoon or something. And, I remember thinking, why am I putting up with this? I’m better than this, I want to enjoy my work more. I spent years trying to get away from that hamster wheel.

Andrew: And that’s, and you got away from it. Can you give me a sense of where you are now, now that you’ve done this. What’s life like?

Rob. There’s kind of three things that I’ve found that are important. For years, I was just seeking freedom. Freedom from clients, freedom from bosses. And I’ve found that. There was a day in 2000, gosh it was 2008, where I woke up and I realized no one was going to call me on my phone, and I could dictate whatever I wanted to do that day. And I have to work on my business, it’s not like I’m retired. But, I remember specifically going to Borders and just having a cup of coffee, and kind of reading some books and realizing this is what I would do if I had ten million dollars in the bank. I wouldn’t change this, you know. And so dollars in the bank. I wouldn’t change this, you know? I would do that every day now, but I have realized that freedom is the first component and then after that, I realized it was purpose and relationships. And so, once you have freedom it actually does get boring after awhile. And so purpose I’d be, there’s I get from building new businesses and acquiring [??] and working with other entrepreneurs.

Andrew: All right, so you told us what life was like and how frustrating it was. It was time for you to get started. What did you do to get started with this new life?

Rob: You mean after I was done with consulting and done with people yelling in your ear so loudly on Christmas that you have to hold the phone away from your ear?

Andrew: Yeah.

Rob: I really, you know I took that time to really start to build my businesses and I’m big on education and on learning. And so I remember the first couple months, after basically getting out of consulting and realizing that I did in fact have pretty much a full-time income from products, that I wanted more. And I wanted, I didn’t want to stop learning. And so what I did was I went out and tried to expand my product, you know the products I own. I bought new products, learned new marketing approaches, and I went back then and applied them to the products I already owned.

Andrew: So you already had revenue coming in from your own products before you quit your job and..

Rob: I did.

Andrew: focused on it full-time?

Rob: Yup, and that’s something. I’m not a super risky entrepreneur. I had a wife, and a kid, and a mortgage and I wasn’t the kind of person who’s gonna quit with no income. So my number was, I wanted to be at 70% of what I needed to live on before I quit and when I hit that, that’s when I quit.

Andrew: All right, so how’d you get to that?

Rob: Well, I mean it was, it started with a lot of failures and just launching stuff that was, that seems kind of random now. But, it basically amounted to, ya know, not having a lot of guidance. In like ’99, there was no Mixer G and there was no one blogging about this stuff. And so it involved launching probably 3 or 4 failed products that I think . . . I don’t know if you want to start on those right now or go into them later in the interview.

Andrew: Yeah, let’s go for it. What was the first product that didn’t work out?

Rob: So, in 1999 I was actually kind of teaching myself how to code in modern languages. I graduated from college and I didn’t know any of the PERL or PHP, or anything, because they don’t teach that or they didn’t teach it in schools. And so I teamed up with a friend and we built an ISP that was basically like a, like a marketing Fernando reseller? And we wrote a bunch of code to build, like an online quiz and we called it smartguy.net and we said in order to be part of this ISP you have to be able to pass this quiz. And that idea, I know the look on your face is like “what are you talking about” and that’s in retrospect, like I think the same thing. It was a terrible idea, but we just, we had no idea how to market. The only thing we’d ever seen were like McDonald’s ads and you know, Visa ads and you don’t understand that to get real customers it’s a whole different ball game. And so that’s . . .

Andrew: Why? What’s the difference between the way that Visa can advertise and the way that a new online entrepreneur can advertise? And why can’t we learn from the best? You know, Visa spends a lot of money on research to understand how people’s minds work and then they spend a lot of money on advertising and they wouldn’t spend that money unless it worked for them. So why shouldn’t it work for us?

Rob: Right, well a couple of things. So one they have 8 and 9 figure advertising budgets, so they have hundreds of millions of dollars to spend on it. Two, they’re big time into brand building and brand building does not tend to convert directly into sales. And as a bootstrap entrepreneur, when you have $2,000 in the bank, you really have to look for things that generate sales. As much as, I would just love to have ads that kind of talked about some random thing or had a cool image and had my logo, that doesn’t actually put money in the bank and that $2000 will be gone very quickly. So it’s a big mistake to look at people who aren’t in your same situation and then try to model them.

Andrew: So I kind of feel that I understand what you were trying to do at smartguy.net. You were thinking, look there’s some people out there who are really smart. In fact, if you understand what ISP stands for, if you know that it stands for internet service provider, you’re ahead of most people. And if we can acknowledge that in you, then you’re going to gravitate towards us. And if we prize ourselves a little bit and make you want to earn the right to work with us, then maybe you’ll work to do it. Why didn’t that work?

Rob: It just wasn’t important to people. It was a commodity business and yeah, we didn’t really know how to build exclusivity. We thought that just by telling people that we only let a certain number of people in or people who passed this test that that would be like something people would talk about. And it would somehow spread and be interesting. And the more people we talked about it, the more we got, “Why would I do that instead of AOL?” “Why would I do that instead of NetZero?” “Why would I order that instead of Juno?” That was always a question and we really couldn’t tell them why because we weren’t any better. We finally realized you actually do have to have a compelling value proposition. We built exclusivity with no value on the other side of it.

Andrew: If a bodega put a velvet rope outside its store it doesn’t make it so special that suddenly models are going to standing outside in line to get in. It still needs to be something beyond the velvet rope.

Rob: That’s right. If you put the models on the inside and then you have guys come up and wear the velvet rope then they would maybe look forward to it.

Andrew: Before I go on to the next step, why didn’t you give up? You tried something in a world where it seemed like anyone who took any kind of shot was going to make it big and here you were, you took a shot , you put your name out there, you connected, you told the world, this is what I’m of doing and it failed, why didn’t you just say I’m not cut out for selling, I deal with the customers on the phone or maybe I’ll rise up in the ranks to a point where I won’t have deal those customers but I’m not going to out and do it again, why didn’t you take that direction?

Rob: I did for about a year or two. I always had the entrepreneurial bug and I knew that I wanted to something excited that was bigger then salaried work. It was less of a chose and it’s more of this thing I called my divine restlessness, which is painful and It means that every 18 to 24 months I need to reshape my work career, but it’s divine in that it always keeps me going to the next level. That’s what happens. I was burned out; we had invested so much time in that. All of our money, which wasn’t very much I was just out of college and it, was failure but it was an intense learning experience and I realized that I learned a few things about that. I learned that marketing is hard and I need to get a smaller niche and know how to reach the customers instead of going door to door and hanging things on…

Andrew: And now you’re such a good marketer that other entrepreneurs have told me that you’re the reason that they were able to get any customers at all. You just did a course with me; you recorded it for Mixer G Premium, where you taught us how to market our stuff. I want to learn how you got there and I also wrote a, I want to make sure to ask you about that throughout this interview, and I also want to find out about this divine restlessness. Most entrepreneurs who do more then one business suffer for lack of attention and I went to MicroConf, the conference that you put on, it was such a good conference, so polished, so well put together that I felt like you understood our needs as attendees and speakers in a way that most conferences could never understand and you got that right and anyone who takes a look at Hittail.com and then old.hittail.com, to see what you bought and how in a few weeks you turned it around and made Hit Tail into a business with more than double revenues and so on. How can you still manage all of that? I’m going to come back and ask you that but I’m making a note here so that the audience knows that I’m on top of that as we talk about these different businesses I’m going to ask how you can manage all them when most people can’t even manage one. For now, we should continue with the narrative. This was 1999, you got that failure, you’re smacked in the face it felt like by entrepreneurial life, and then it was four years later, no, three years later you launched the next business.

Rob: Yes. My wife went out of town, I was developing software full time by this time, its 2002 and my wife went out of town to Africa for six weeks and I basically watched all ten seasons of Friends in about six weeks. It was embarrassing, I would come home from my salaried gig and I would just code at night, I would code about eight hours a night. I feel like these days are not talked about enough on podcast and blogs and interviews with entrepreneurs because I do feel like I’m successful now. I feel like achieved a certain level, I’m always looking to the next. I worked hours, tireless hours, during that time. There was a night for almost 40 days straight probably to get this little tiny app out, it was called feedshot.com, and it was basically a service that allowed you to admit your blogs to blog search engine, back then there were these special blog search engines. The idea not genius by any means but I saw a need in a market and [?] couple blogs and I realized some people used it. So after six weeks I launched to not much fanfare.

Andrew: Six weeks, how painful was it? It seems like six weeks can’t be all that painful. That seems like a pretty quick launch.

Rob: Yeah, I won’t say it was that painful but it was, I remember working on it and thinking to myself, is this going to be smartguy.net again? Am I going to waste all this time? Because I value my time pretty high even before I was an entrepreneur. I was stressing all the time about am I maximizing either the pleasure or the productivity are the two things I tried to do so I was thinking am I really getting something done here? Am I really building something of value or am I pissing away what amounted to be 150 hours of my time basically, so yeah it wasn’t that bad but I was, I mean I was working basically 9 to 5, come home and eat dinner, then I’d code from about 6 to 2 a.m., and I did that for six weeks straight pretty much, so it was, I was tired [??] by the end of it, to say the least. And I, you know, the site launch actually got some traction, the cool thing about it was it was a niche, it was aimed towards bloggers, people starting blogs. Suddenly I learned like, oh, if you market almost exclusively online, you have a little advantage, you don’t need as big of a budget, you can start taking advantage of the online world. And you can also, if you focus on a niche, I realized it’s easier to find people, where they’re hanging out. These are all lessons that I took with me as I moved forward.

Andrew: All right. What happened next?

Rob: So [??] was just a… I thought it was going to bring in thousands of dollars a month, I seriously did. Which in retrospect I would be able to verify that it would not, in advance. But back then I didn’t know how, so that made like a hundred, two hundred bucks a month for a while, and I was just like, “Oh my gosh”, I need to do a bigger deal. Like a venture funded start up. So that was what I was trying to do the whole time. I was really geared up for that, until I saw an app for sale on eBay, and it was called…

Andrew: Before you go with that, my audience would be upset with me if I didn’t follow up and ask you about, what would you have done differently to know ahead of time that that didn’t work?

Rob: So these days when I’m going to check out an idea I go with a market first approach, so what I was doing in the old days was product first, the product first approach. Where it’s like you think of a product idea, then you go out and build it, then you see if you can market it. What I would do these day’s if I was going to launch [??] again, is I would have gone to the Google AdWords keyword tool, I would have looked to see how many people are searching for something related to this, like a blog search submission service, all those things. I would have also touched base with some bloggers I know and say hey do you need this? Would you use it? Would you pay for it? I didn’t ask anyone before I dit that. And the other thing I would have done is I would have put up a landing page the day I thought of the idea, and I would have started sending traffic to it as soon as possible, and even if I only got a hundred or two hundred emails, at least that’s a small base of people that you can start off with, can give you some kind of initial revenue. Because I basically sold nothing, and it was really depressing when it first came out, to be like alright all that time and, you know, no money.

Andrew: I see.

Rob: No payback.

Andrew: All right, again, another setback, next year you said that you discovered an app. By the way, I got to call myself out on this, my hair never looks good in these interviews and I refuse to spend time on the way I look, but boy when there’s this one clump just sticking out here, I better acknowledge it, because I can’t tap it down, it’s not going anywhere, I tried earlier.

Rob: I didn’t even notice. I bet no one will notice.

Andrew: I need a headset, maybe that will kind of work. So then you discovered something for sale?

Rob: Yeah, so I backed off the development, you know I had several ideas for new products over the next year but I was exhausted in realizing, like, I’m not going to be able to put in that six weeks of hard labor, or if you spread it out over six months it just takes that much longer to fail. So I saw this app for sale on eBay, and it was called ChitChat.net, it was forum software written .net and I happen to be a .net…

Andrew: It was what software?

Rob: Forum software, like discussion forums. And it had low minimum bid, and on a whim, I was thinking to myself wow a complete product. I mean this would be probably like three to four hundred hours worth of work to build this software, and I wound up buying it from the guy for 150 dollars. The whole, you know, all rights to it. And I was like yes, this is it, I’ve found the, I have real software now. And all you have to do is just scale this, you just market it, and scale it. And I’d been reading [??] on software and Paul Gram and stuff so I really did not understand how challenging the marketing would be. And so I bought the software, I took possession of it, and nothing happened. No one, no one came. I didn’t sell any copies. And so that’s when, well I tried a bunch of stuff, I actually bought fifteen hundred dollars in AdWords in a month, and sold one $99 copy of the software.

Andrew: Oh wow.

Rob: And realized this is not. Yeah and that was a lot of money right? I was totally [??].

Andrew: So that’s what I’m learning so far is that marketing come first, before you even build a product. And then having a product, whether you built it yourself and thought it was great, or buying it from someone else and not having to put a penny into it, or not an ounce of work into creating it, doesn’t matter if you can’t market it.

Rob: That’s right.

Andrew: How did you learn how to market? Before we go on with the story, you’re a guy who loves to learn, who has benefited as we’ll see later in the story, from what you’ve learned about business and software. How did you learn to become a better marketer?

Rob: So eventually, I have to be honest, if I were doing it today, I would be a member of your paid Mixergy membership.

Andrew: MixergyPremium.com

Rob: Yup, I would go after like Noah Kagan’s stuff I think is really good.

Andrew: Yeah.

Rob: I would read, I would follow me, I wish there was someone like me doing things that are as tactical that I blog about, I wish my book was out. There are other books out there today that are so much more detailed than what you could get in 2003. And so in 2003 what I did was, kept going. I kept trying to teach myself, and as a result it took another five years, because it wasn’t until 2008 that I eventually was able to quit consulting, so it really was a hard, it was like that perseverance thing of like you try, you get it wrong, you learn, try, get it wrong, learn. It was a kind of a long loop.

Andrew: 2008 and we started the story with 1999 Smartguy.net. Alright, so then, well amazing that you didn’t give up at any point throughout.

Rob: I thought about it.

Andrew: You also said tactical, you’d gravitate towards reading blog posts, taking courses, reading books that are tactical? Why that and not big ideas?

Rob: Well, I mean there are plenty of big ideas out there, but I find that if I’m not taking notes that I can apply to what I’m currently working on, that it will almost never come to fruition.

Andrew: I see.

Rob: So if I go to a conference, if I listen to an audio book, if I listen to a podcast, if I read a blog, I need to be doing something with that information or else it just, you’re just pushing all this information in your mind that you just never utilize. So yeah if I’m not taking, I call them action notes, I have a notebook that I keep, and as I listen to, you know, Mixer G interviews, or pod casts, or whatever, I’m really thinking how can this apply to Hit Tail, you know my current project, or I’m writing my second book and I’m thinking how can I use that to market my book? You know…

Andrew: I see.

Rob: So it’s both learning, which is fun, and it’s going to hopefully provide me some value in the long term. And actually make my products better.

Andrew: Alright, we were talking about ChitChat, nothing happened or…

Rob: Nothing really…

Andrew: What was next?

Rob: Yeah, I wound up having my first child, my wife did. And I sold ChitChat for a few thousand bucks, it was cool, it was profitable, but really I saw it as an experiment, you know.

Andrew: Did you sell it on your blog?

Rob: I did.

Andrew: You were blogging by the way, 2003, it just hit me right now.

Rob: 2005 is when I started.

Andrew: OK and so you sold ChitChat.net on your site?

Rob: I did, yup. I just posted it and said if someone’s interested, that I’m having a kid, and it was, by that time it was selling 300 dollars a month.

Andrew: OK.

Rob: 300 I think, three to four hundred. So it had made progress, because it was doing basically nothing, or like $99 a month when I bought it. So I had figured out some very subtle things, but nothing I could reproduce.

Andrew: OK.

Rob: And so I sold it, I took the cash, I had a kid and then realized I would live to fight another day, hopefully.

Andrew: Alright. I’ve got your whole list of companies here along the way, and there’s a lot of asterisks, failure, asterisks, failure, asterisks, failure.

Rob: Yeah.

Andrew: Floggs.com was a dig for personal finance, that was in 2004. And then, maybe we talk about 2005?

Rob: Sure, so in 2005 was really my first, what I would consider my first success, that actually made a few thousand bucks a month pretty consistently. And the reason…

Andrew: Pretty consistently.

Rob: Yeah, pretty consistently yeah. The reason I even talk about money is because I feel like people talk about like, I launched a social networking app and it’s successful because it has 10,000 users or 20,000, and I don’t, when my goal was to quit consulting, you know or quit me job, I had to get to a certain level of earnings. So really I’m not a super money driven person in general, but the money was to buy me freedom and so that’s where my first success was actually making a noticeable dent in that, that place where I had to get to. So anyways, yeah so .net invoice was posted on SitePoint, was posted on some forums, and these guys were like look we developed this site, or this invoicing software and we don’t know how to market it, we want to partner with someone. And I had a little bit of experience and I started emailing with them and I quickly realized I didn’t want to partner with them. So I offered to buy it, and why I, in retrospect I’m not exactly sure why I did that having already had a failure with ChitChat. I guess I just figured more to learn about, it’s bigger stakes, and we settled on an acquisition price, it was actually…

Andrew: You still remember what that is?

Rob: Yeah, you know, it was $11,000.

Andrew: That’s a lot of money.

Rob: It’s a huge amount of money, I know. In retrospect.

Andrew: And back then you hadn’t had a success yet and you’re still working like a hamster in a wheel as you say, and here you are spending $11,000.

Rob: Yep, and the money came from consulting work that I was doing on the side. That’s the only way I justified it to my wife is that I had earned it from extra stuff, it wasn’t like out of our personal savings. And I freaked out, I mean I had a, in retrospect I overpaid for it. I should have paid, if I were to value it today, I should have paid them closer to about, well somewhere between $5,000 and $7,000. When I bought it I e-mailed the e-customers, the existing customers, and said, “Hey. I’m the new owner. I’m going to develop [??].” Within hours I had 25 pissed off e-mail replies. They e-mails basically say, “This software sucks. It has show stopper bugs. It doesn’t add numbers correctly. The previous developers were not supporting it.” They were just flaming. I was completely freaked out.

Andrew: Invoice software that doesn’t do math right is not good.

Rob: Yeah. It was crazy.

Andrew: What size revenue was it doing when you bought it?

Rob: That’s one of the reasons I ever paid for it. The guys had said, “Well, the PayPal and the past is all messed up. We really just have the previous month,” and this is a red flag, people. You need history. So, they’d shown me a previous month and it had done $800 or $900 that month. So, I was like “Sweet.” It had done $800 or $900 a month. I was all optimistic, so I offered $9,000, and we kind of negotiated back and forth and settled at $11,0000. When I got it the first month it sold three copies $95 a piece, so it was doing $300 a month.

Andrew: Oh, wow. It’s one time.

Rob: Yeah. It’s not recurring. So, my heart sank. I did not tell my wife. I thought, “I just pissed away $11,000. I can’t believe it.” I genuinely thought that I should give this thing up, like the whole thing wasn’t going to work out, but I sucked it up, basically, and I was kind of making this work. I thought, “If you can’t make this work you’ll never make anything work.”

So, I sat down and did that eight-hour-a-night thing again. This was an interesting time. I fixed about 20-something show stopper bugs. I tripled the price of the product. I talked to a few friends who said that it’s, basically, under priced for what it is. If it’s really good it should be $400. So, I raised it to $300. I started doing some SEO and things that I learned about.

The next month it sold three copies again, but I tripled the price, so it sold $900 worth. It was at that point that I realized, “Wow. If I can keep this up I can pay this off in a year.” Suddenly I was not freaked out; that’s not a bad pay off. Then I did a little SEO, got some new customers, did a new release, and it did almost $2,000. It stayed there for about six months for about $2,000 a month.

Andrew: It paid off in profit.

Rob: That’s right. No. I dropped another $1500 on Ad Words and stuff, but in the end it did; it paid itself off pretty quickly. That was when I realized, “Oh, you can succeed at this. There are successes out there.”

Andrew: Did spending more money on this than you spent on any of your past businesses make you feel like you had to work harder?

Rob: Yes, it did because I had a sum cost. I wasn’t going to give up on that. I think that admitting failure at that point would have really done some mental damage to me in terms of not ever wanting to take a risk that big again.

Andrew: I see. Right. If you’re spending $115 it doesn’t work out, OK. If you’re spending $11,000 and it doesn’t work out it’s painful.

Rob: Yep. Yep.

Andrew: Interesting. I’m pretty new to marriage. Olivia’s very supportive of whatever it is that I do. I guess whatever I do could change our lifestyle somehow, but she’s pretty open with it. But I wonder if we had set back after set back how she’d feel about it. In fact, I do know when I was thinking of investing in startups and making that part of my investment portfolio that she was a little hesitant about it. I guess if I were to put everything into startups she would be more hesitant.

But, I can start to see that it’s no longer me taking risks and everything is fine. It’s now someone else feeling like, “Whoa. There’s a guy driving the car, the vehicle of our life, and I don’t have a say in it. No. I should at least speak up.” Tell me a little bit about the conversations that you have and how you deal with it. That’s a long way of asking that question. Sorry.

Rob: No. It’s a really good question. It should be asked more, I think. I think without the buy-in of your significant other you’re really going to run into a lot of problems because you are going to have set backs, and if you’re significant other is kind of ragging on you the whole time, male or female, you’re going to be so much more likely to quit.

In 2005, 2006, around that time, it really was a matter of me saying, “Look, I make good money as a programmer during the day, I support the family,” she was in grad school getting a PhD, “and that’s not going to change.” I kept telling her, “I’m not going to quit my job. I’m not going to change our lifestyle for this stuff. This extra money is really extra money, and if I can make it work, we can have a good life and this will make me happy in the long run.” Early on she was very risk adverse. She’s not entrepreneurial and that’s OK. As the years went on and I started [inaudible]. It was the small successes that convinced her later. I was going to quit this [inaudible] maybe $200,000 a year, and she didn’t bat an eye, because I had so many successes by the time I did that, that she had confidence that I would make it work.

Andrew: I see. It was just building up over time.

Rob: It was.

Andrew: You said I’m going to quit this and built this $200,000 a year business. I can get this to 200, you hadn’t gotten to 200,000 when quit right?

Rob: Oh no, that’s what I was making at consulting, but I didn’t need that much to live.

Andrew: You were making $200,000 as a consultant?

Rob: Yes, I was billing $100 an hour. I was a developer, it was $100 an hour and I was busy at least 2,000 hours a year.

Andrew: Why weren’t you then so comfortable that you said, you guys are yelling at me I’m making $200,000 a year this is only going to grow. I’m in the in-demand field. I’m in D.C. right now, I feel like everybody is in this comfortable place. They’re not even making $200,000 a year they may be making $100,000. A Comfortable life over here and they’re not pushing themselves to take risks. Why weren’t you that kind of person?

Rob: Because consulting doesn’t grow, that’s the problem. I tried to grow it. I hired an employee, and I tried to get more work and scale it up. It just doesn’t do that, it’s really hard to do that. So, I realized that products were where it’s at. Here’s the thing, it wasn’t to grow revenue. Every year was between $140,000 and $200,000 as a consultant. But the thing is when you’re super unhappy the money doesn’t matter. As weird as this sounds, everyone I know that makes this much or people I know who make $10 million. They wind up having all this money, the money is not what makes you happy. It’s doing things that are really interesting to you. Building things for other people was not interesting to me.

Andrew: Yeah. I tend to think money does make us happy. I hate to say it, but not salary money, it’s having money in the bank that’s never going away. That makes you happy because it gives you the freedom go to do what you want. To say ‘screw off’ to anyone who’s trying to get you to do things that you’re not excited about. But, if you have to keep earning it year to year then that almost makes you feel like a slave to it, and you’ve expressed that here.

Rob: That’s right. You said, the money isn’t what makes you happy it’s the freedom that you get.

Andrew: Yeah.

Rob: That’s what it is.

Andrew: By the way, I got that because I remember working with this woman Rosalyn Resnick who sold her company for $100+ million dollars I watched her as she built this thing from home, took it public and so on. When I asked her to do an interview here, I asked her what’s the best part of having sold and gotten here, because I know how hard she worked to get here. She said, “freedom” with this excitement and I’ve seen that in other entrepreneurs too, that sense of freedom that comes from it. When you get to a certain level it’s just priceless.

Rob: Mm-hmm.

Andrew: You can tell me I can go meditate. I went to a meditation retreats where I sat silent for days. For a week, for ten days maybe I’d meditate. You’re supposed to find happiness and inner peace and not need anything from the outside world after that. I still needed stuff from the outside world.

Rob: Yes.

Andrew: That didn’t give me the kind of freedom that an entrepreneurship does. Next, you applied to Y Combinator, you got turned down. Are you holding a grudge against Paul Graham, the guy who you read about for so long?

Rob: No, not at all. They evaluate their ideas based on what they know. In retrospect they were probably wise to do it.

Andrew: Why, why were they wise to turn you down. A guy that ended up being successful.

Rob: Well, maybe I won’t say wise. We probably could have made it work but it’s such a crap shoot. I know they get 800 applicants and they have to do the best they can. I applied with a couple MBA’s I met in New Haven, Connecticut. We made it to the second round. At the time I thought the only way to do this financial freedom, not even financial freedom just freedom to do what I want, was the big score. It was all about the venture funded stuff.

Andrew: I see. I don’t know many people who hold grudges, maybe, I can’t even think of one right now who holds a grudge that they didn’t get into the Y Combinator and get funded by Paul Graham. I think if you were successful I don’t think Paul Graham is the kind of person who would begrudge the success because you turned him down or he turned you down.

Rob: No.

Andrew: I like the analytical mindset that goes into Y Combinator. They’re thinking, what’s wrong with our system or what could we adjust in our system to capture guys like Rob in the future. Maybe you’re thinking the same thing. If you had to, what could you’ve done to present yourself differently to Paul Graham , to Y Combinator in general to get funded by them back then?

Rob: One thing I wish that I’d called out more and I didn’t was the marketing experience and the success that I’d had with Dynet [??] invoice. All though small, I realize how unique that is, how rare that is. How few people actually have even marketed a product to a few thousand dollars a month, is a big learning experience. And I didn’t put that. I was kind of like, “I’m a big software developer. Look at me! I’m a consultant, you know?”

Andrew: And you didn’t think enough of the couple of thousand bucks that was coming in . . .

Rob: No. I was like, “That’s not going to matter.” And it wasn’t even the couple of thousand. It was more like, that I had made some decent marketing choices and figured out how to get the business to that point. A success.

Andrew: All right. Again you go back to SitePoint and you acquire another . . . why are you acquiring at this point instead of starting from scratch?

Rob: Yeah, so this is when it switched for me. I realized that I was going to learn the more new things that I did, the more I was going to learn and I wanted to accelerate my learning process. I was working, like I said, 3,000 hours a year, which is full 40 hours a week. And I had more money than time at that time in my life, but the opposite, when you have more time than money and at this point I was making good money and realized I don’t have time to invest 2, 300 hours to build a product. Especially at my billable rate at that point, that’s like 20-$38,000 to go build something that I could buy for a few thousand, frankly.

Andrew: I see.

Rob: So that was it, the economics of it changed. So it’s not going to be right for everyone, but that’s, that is why I started doing that.

Andrew: So you bought justbeachtowels.com. Why do you think that that was the next business to buy?

Rob: Yeah, so at this point I realized that I had a goal and it was to make 7,000 bucks a month from products, and if I hit that it wasn’t, it was, it was about what I needed to live on in support. Everything, including retirement and healthcare and all of that stuff. And so at that point, I realized I wanted to, I needed to shoot for that number. And so it did become, I extended my definition of what it was going to be, what it was going to take me to be successful, basically. Whereas previously, I’d said “Oh, it’s got to be about venture funded, right. It’s got to, I’ve got to have this big escape and have the big 10 million dollar exit. When I looked at .invoice [??] and saw that it sold for a couple grand a month and on, and on, and on and I realized if I put two or three of these together, I’m quitting my job. So that’s what I started looking for, was smaller ideas that were practical, that served a niche that I could market and I realized that was kind of the quote, unquote secret. So..

Andrew: When you talked to our producer here at Mixergy, you told Jeremy, “I grew revenue at a couple of thousand with a drop-ship model and virtual assistant to handle the business.”

Rob: Yeah.

Andrew: How did you, I understand getting the business to a point where a virtual assistant can run it if you’re using a drop-ship model, but how did you grow revenue at justbeachtowels.com?

Rob: So, this was, this was across, this was that. I have a saying, I’m sure someone said it before me, but it’s “The harder I work, the luckier I get.” And, that’s how justbeachtowels came out for me. It was like, I had worked so hard learning all this stuff, that when I bought this site, which was just a one page website, it ranked well in Google, ranked on that second page I think, maybe on the bottom of the first page. And I realized like, “Huh, if I get this to the top of this page, like it’s going to get several thousand people a month, purely thru SEO.” And they were searching for beach towels, and so I knew that I could grow revenue that way and it was a gamble. I could’ve bought it and never grown it, but I risked the money and I worked on the SEO, I got it up to like number 4 or 5 on the page and it had enough traffic that it was selling, I don’t know, a couple hundred beach towels a month. It was a couple grand a month in revenue and at that point it was a headache, right? Because then I was working with drop shippers and see that’s when I hired my first virtual assistant.

Andrew: By the way, Matt, the founder of Sitepoint, is one of the first people first people I interviewed at Mixergy. I read an article about him in the New York Times about how people were going to Sitepoint to buy businesses. They were doing some magic to them, like you are and they were selling and basically flipping them. So I said, “I’ve got to get the founder on the air to talk about what these guys are doing when they buy the sites and how, how do they make it more valuable?” And that’s one of the most useful interviews that I did, especially in the early days. If you’re on Mixergy, go look for Matt and Sitepoint, and you’ll see that. It’s my first interview with Matt and since then, he and I have done two others since he’s such a good guest. He’s methodical like you. He thinks about what he’s going to do and what he has done in a way that’s so systemized, that you can learn from him instead of sitting here and saying, “I don’t know, it just works out. I don’t know what these guys do. They just know what they’re doing and it’s just SCO. They don’t keep dropping these black boxes in your lap. They explain what’s in those black boxes. And then you go on and you get another site, another CMS, content management system themer. That means, what does that mean?

Rob: So yeah, the site was CMSthemer.com and it’s still up right now. Basically, it was a site where you could submit a photo shop file, a PSD, and the previous owner would sit there and hand slice it and give you back a WordPress theme, or a Drupal theme, or a Joomla theme, or a CMS theme and the site was gorgeous. That’s what I liked about it. His design was really nice and it was converting well, and he was making… I’m trying to think. He was making a few grand a month 2500, 3 grand a month. And so this fit into my thing, right? It was a small site, very niche, serves a purpose, serves an audience that has a really strict need, and it looks really nice. What I didn’t like is that I don’t know how to make it CMS [??], right? I don’t know how to slice it. So I bought it from him. It didn’t sell on Flippa. I think Flippa might have been around by this time, but it didn’t sell. I made him an offer.

Andrew: Flippa was the … It’s what the site point forums where people bought and sold sites became. It became Flippa.

Rob: Yep. And so I bought it from him, and I had a design firm I had been working with offshore, and they started doing the slicing for me. So basically turned it into… I split the revenue with them, is what it was, so that I didn’t have to do any of the actual technical work.

Andrew: You did the marketing, they did the cutting up? I see.

Rob: Exactly. So I owned the business, but I outsourced the actual technical side to them.

Andrew: That’s [??] Sorry, go ahead.

Rob: And this is where advertising really worked for me for the first time. Actually, AdWords had worked for me before, but this is where I went… I went to BuySellAds and bought some banner ads, and they really converted well. And I realized that having a tight niche helps tremendously, and really focusing on the value… This is a really basic value proposition here, right? It’s not hard to explain.

Andrew: Yeah.

Rob: A lot of PSDs that need themes, and this was it.

Andrew: Yeah, you go out to a designer and say, “Build me a nice design for my website.” And they do, and then they give you this photo-shop file and go, “I don’t know how to make a website out of this. What do I do with it?”

Rob: What’s this? Yep.

Andrew: And I go, “Well you go find someone to cut it up like those people who are just hanging out on the street somewhere to take that and make it into a site.”

Rob: Exactly.

Andrew: And you go to cmsthemer.com, and that’s what you guys did, or that’s what you did when you owned it, and that’s what they do now. That’s a lot to outsource. Basically, the guts of the business is sent to someone else.

Rob: Yep, so I became a project manager. I had to do Q/A, I had to keep them on track, on schedule, on budget, all that kind of stuff. I actually wound up selling that business later on. It fit really well into my early, getting me to the place where I could quite consulting, but it wasn’t a long-term sustainable business. It was more like consulting than the product business I own now. But it was a great stepping-stone.

Andrew: OK. You sold that 2008, $7000.00 for Beachtowels.com, and $12,000.00 for cmsthemer.com, and then you started writing Start Small, Stay Small: A Developer’s Guide to Launching a Startup.

Rob: Right.

Andrew: So at that point you went from being a guy who was clueless, who had failure, failure, failure to a guy who was teaching because you did so well, and it’s all by just reading the forums, trying things out on your own?

Rob: Yeah, the forums were a big deal, SitePoint, and frankly any book I could get my hands on in terms of startup marketing and software marketing. And then the experience of trying things out taught me just reams of information, and I started blogging about this stuff, and that’s when my blogged really picked up. It had been around since 2005, but it had maybe a couple thousand subscribers in like four years, which is just painfully bad, if you think about it… Or just, it was painful. And then as soon as I started writing about these entrepreneurial things I was doing and some, and these are moderate successes, to be honest. I didn’t have major goals. But when I started blogging about them, people were really interested in what I was doing, how I was doing it, and that’s when I realized, “I need to put this into a more formal something.” I realized I had information that could be helpful to other people, is frankly, what happened.

Andrew: You know, a lot of times when I talk to entrepreneurs and the want to blog, they tell me that they’re not going to because they’re too new, or they’re too young, they’re too inexperienced. There are guys like Chris Dixon, who invested in Skype and started Hunch and sold it, and is all kinds of stuff, he’s blogging. And Seth Godin is blogging. Why should anyone listen to them if they’re not at that level? It worked for you. You got past that. How do you get past that hesitation, which I think is pretty natural?

Rob: You know, I took it slow. I already had a small audience, and I think that people who… If you have just a… You’re actually better off having a few hundred people read you because you don’t have to be perfect. If you had the big audience, there’s a lot more eyeballs on you, frankly. And so I was basically just blogging day to day about what I was doing naturally, and when people were so interested in it, and people were saying, “Wow, this is really cool. I want to do this too.” Then I realized, “Oh, I guess I do know something that someone cares about.” That was the realization, so I didn’t get past it because of something internal to me. It was purely external feedback of people saying, “I want to learn more. This is intriguing.”

Andrew: When I was researching [??] of WooThemes, I went back and read his blog post when he was in the just trying to figure it out point, and I wish I could communicate that in my interview with him, that the sense that you… You see him saying, “I’m going to try this new thing and it’s going to work out. Here’s my new goal and I don’t know if the blog post communicated it well, the follow-up, but that goal bombed and then you’d see him go and try again and, and I somehow got wrapped up in this story that even though I knew where it was going and I knew how well he did with Woothemes it is compelling to watch someone as they’re building if they’re learning along the way, if they’re suffering and if they’re dreaming, I totally get that. But when it’s me I sometimes hesitate.

Rob: I agree.

Andrew: You turned the book into a website. What was the website?

Rob: Oh, I actually, I started writing the book and I realized that there was a lot more that I wanted to do that wouldn’t fit into, basically wouldn’t fit on paper, and so it was, I had screen casts I wanted to give about AdWords because I had had success with 150 to 200% ROI on my invoice ad campaigns, as an example. And I had learned a ton about how to do. I had learned a lot about SEO. And those things are so much more easy to explain in a screen cast or audio even, then to try to write it out. So I realized the book was a limiting format and I, around this time I was getting so many emails with questions of how I was doing, you know, the stuff that I was doing that I realized I might want to start some kind of online something, you know, some kind of website that taught people how to do this where I could actually provide multi-media. And I was originally just going to have a big zip file they could download. But then I heard about this concept of like membership websites and realized I could, oh, actually getting people together into a community where you have forums, you can do a little tighter mentoring. I mean, there’s just more than just shipping someone a zip file. And so I launched, I think is was in 2009, yeah in 2009, I launched micropreneur.com, which is, it’s the micropreneur academy and it’s basically me and now my business partner, Mike Taberg, who puts on MicroConf with me. We help aspiring entrepreneurs, aspiring micropreneurs, who are looking to launch stuff on the side is the key, it’s not get big Facebook killer ideas. These really are these few thousand dollar business that can kind of get you on that track and get you experience so you can either, you know if you want to just build a few more and then quit your job or you want to, you know, go up the chain basically and try to raise venture capital. Any of the stuff is helpful to learn.

Andrew: So you are the micropreneur guy. Did you coin the word by the way?

Rob: You know, I thought I did, I bought the domain from someone who owned it and I went back and read some book from like the ’80’s about starting business and some dude in there is like, micropreneur, so I don’t, no, not really.

Andrew: But you are the guy identified with this.

Rob: Sure.

Andrew: And I’m wondering why? Why limit yourself to micro? Why not say this is going to be the megapreneur, this is going to be, you may be small now but where I’m getting you to think, where I’m thinking with every site that I have, including justbeachtowels.com, it’s going to be a billion dollar hit or I don’t want to deal with it. Why not go big or go home like so many people say?

Rob: Sure. You know because I had tried that and it hadn’t worked and I saw what had worked for me and what that. And what had worked for me was to go niche and to go small and to focus and there’s these kind of tenets I throw out, it’s like, finding a market before you build a product. It’s learning internet marketing for the most part. Because if your going to launch something on the side, it’s really hard to do direct mail and cold calling, you know, offline marketing techniques. You really do have to be mostly online. And it’s providing like real value that people will pay for, that’s a big key, right? You can’t start a social network and be a micropreneur because you can’t just monetize that well enough without having venture funding. And so, I realized that these things were successful and I won’t say no one but almost no one was talking about them. There was no real platform for this. And so that, that’s why I went with it. Everyone’s talking about going big. You go, you know, Inc Magazine and Tech Crunch, these are all the sites everyone talks about when they talk about start-ups and frankly that didn’t work for me and I think it doesn’t work for a lot of people and so that’s why I went micro, was to try to, because it worked for me and I want, I genuinely believe that it can change people’s lives. And it has, I do get emails still from students and people I’ve mentored who have that awesome phrase of like, wow, you changed my life, like this has absolutely changed the way I live. Ruben is one of them, he quit his job and moved to where he wanted. I have several others I’ve received in the past few months. It makes me really, that’s like the big value for me of doing all this micropreneur stuff. The teaching is actually impacting people’s lives and making them better because I’ve been there. I’ve been there were it sucked and where I made a bunch of money but wasn’t happy at my work.

Andrew: Yeah, Ruben is one of them and he came on here to do an interview and talked about how he quit his job and started Fit Sketch and he’s the one who told me how you helped him earn revenue before he even launched his product, and I think that got me to fire off another email at you, and you said, no. I thought we were friends, and before I continue, what kind of heads down mode do you get in to where you can’t come on and do an interview for an hour?

Rob: I know.

Andrew: I don’t have a problem with it. Look I don’t care. I don’t mind you kicking me in the balls, not that you have, but why don’t you tell me why? Tell me the psychology that went into hurting me, not that that hurt me. What I’m curious and care about is the curiosity more than anything else. So tell me, what happens?

Rob: I do focus. A lot of entrepreneurs I see go into a bit of a hibernation mode. And if you notice, like if you go to my blog which is a pretty good indicator there will be two month gaps where I barely post anything. I hate doing that, that kills me. I know what it does to the blog. I know what it does to the audience. I know that I should be putting something out once a week. But when I’m truly heads down I making massive strides forward. In a couple of months I can accomplish like what I would be able to accomplish in six months at a salary job. Because it’s so focused, I don’t do anything else, and even during an interview it kind of throws me off my game, because I have to prepare for it. I have to think about my story, it’s all that stuff.

Andrew: I’m starting to say no to interviews and here I am. The guy who tells everyone they should be interviewing and I have to say you shouldn’t get to interview anyone at anytime regardless of what’s going on. Focus is hard though, it’s hard to say no to people. Especially when they’re fans, when they’re supporters, when they care, and I’ve got to learn to say no, more. Speaking of focus, I was about to say. 2009 you acquired ApprenticeLinemanJobs.com, in 2010 you acquired WeddingToolBox.com, and then 2011 you put together MicroConf, which I went to. You started a podcast, you’re blogging. How do you get it all done when I sometimes wrestle just doing Mixergy? Doing Mixergy I can do, but doing Mixergy and getting [??] fall down, I can’t do, those two things at once I can’t do.

Rob: You know what it is. I have only a couple of things that I’m working at once. And so the blog and the podcast are ongoing. Everything else I will acquire a product, I will improve it, and then I will get someone from my team. I have a lot of folks who, I outsource to, essentially manage it. And so I don’t have to worry about Wedding Tool Box, and Apprentice Lineman’s Jobs, and the other products that I have. Because I’m busy right now, I’m trying to do a blog post every week, and I’m doing a podcast, and I’m doing Hit Tail, that’s the only three things I’m working on. So all the other stuff is, I won’t say automated, because I still deal with questions and things that come up. But it’s not like I’m the front person for all of these apps.

Andrew: So Micropreneur something breaks down, somethings missing. You’ve got Mike, he is on Micropreneur, he’s going to fix it.

Rob: First there’s Andy who’s our virtual assistant, he’s tier one email support, he’s freaking awesome. I’m so glad I found this guy. I’ve had some decent VA’s but he’s definitely the best. He will try to fix it, and then if he can’t, he will refer Steph [SP] to me. And so I am the second line, then depending on what it is I’ll give Mike or take it myself.

Andrew: All right, that answers another question of mine. Why do you need a partner then if you’ve got a great VA… That doesn’t answer another question. If you’ve got a great VA, why do you need a partner on Micropreneur, or anything else?

Rob: I only have a partner with [??]- and Invoice, and Micropreneur. Everything else I own on my own. However today [Dot] and Invoice, and Micropreneur, I might not take on a partner. It was before I knew how to outsource really well. It was before I knew how to find good people. And with [Dot] and Invoice, I started growing tired of it. I was going to sell it, and then a friend said, hey, I’ll partner, I’ll do the technical side, and you do the marketing. So that one kind of works out well. Micropreneur was more like I was overwhelmed with tasks and I didn’t really know how to produce enough content, and so I brought Mike on who’s also an entrepreneur. So it was kind of like stumbling into those two areas. I don’t regret either of them, but if I were to do it all over, I really do these days try not to do partnerships. I try to hire things out instead.

Andrew: I don’t mean to say anything bad about Mike. I like Mike a lot, I met him, but I’m curious about why a site like that would need a partner now I’ve got my answer. Why did you decide to do MicroConf? It was great for me. But you must have put a lot of work in there. When it was a snack, or coffee or whatever it was, it was there just when I needed it. That took time. When it was someone up on stage, that took time. And I know it’s tough to coordinate guests. Why put on a live event?

Rob: It’s a good question. And if you recall, at the end, I was like, “I don’t know if we’re going to do it in 2012.” We have decided to do it. A couple reasons. One is I think like everything that I’ve done, I feel like there is a need for it that no one else is serving. And to me, it’s like you have to go back. I feel the compelling need to go back and help the people who are trying to get to freedom, basically. And I think… I’m hoping MicroConf has some type of impact on people. That it actually motivates them and it teaches them to do the right thing, instead of going after the big venture funded thing. I think it’s an excuse to get a lot of people together who are going after self funded start-ups and smaller ideas. And there’s no other place in the world that I’ve been to, that’s quite like that. So that’s what it is. It’s an excuse to bring us all together, hopefully for the betterment of each one of us.

Andrew: All right. What about this? A lot of people tell me that the way to generate revenue with a business like mine is to organize a conference. That’s where the real money is. That’s where Tech Crunch makes their real money, they’ll say. That’s where [inaudible] make their real money. Don’t you know the trade publications? They make huge money off of it. Is there huge money in putting together a conference?

Rob: I’ve heard that there is. I’ve never seen said money. So last year we made a couple thousand bucks on it and Mike and I invested hundreds of hours apiece. So yeah. I’ve heard that… I think if you get a lot of sponsors. I know I’ve talked to a few conference organizers who will pay for the conference just by having sponsors. So maybe it’s a $60,000 budget, which is all the room and all the rental and all the food and everything. And they’ll get $50,000-$60,000 in sponsors and then all the ticket sales are just net profit, in their pocket. So you have 200 people there at even $200.00-is like $40,000.00. So there’s some money there. You could make $40,000 on it. We are not able to do that yet. I don’t know if we’ll be able to. That hasn’t really been the goal but it would be cool to make…

Andrew: Because you charge so little? Is that why?

Rob: We charge $500.00. $500.00-$600.00. We’re keeping it small. We’re limiting it to 128 attendees because… The feel last year, I’m sure you recall-It’s different than other conferences because it was so small.

Andrew: At the end of the conference everyone fit into my hotel room.

Rob: That’s right.

Andrew: You gave me a great hotel room. I took a video of it for my wife, which I’ve never done of something like that. It was a great room. But everyone fit into the room and it felt by the end, that everyone knew each other so it wasn’t weird to have everyone in the room. So you do keep it small. No more than 100 people come in.

Rob: Right. And we don’t get a ton of sponsorships. We have tried but frankly, at this point we just don’t have the leverage or we don’t have the relationships or something that other conferences do. So yeah. We’re looking to do better than we did last year but it’s not going to be some enormous, five figures sale by any means. We’ll probably make a bit more than minimum wage, I would guess, on it. But here’s the thing. But I don’t need that. I’m not doing that for the money, right? Remember I told you I had that goal of $7,000-8,000 a month? To quit my job? I hit that. And once I got past that, I realized everything else is good to have but I don’t necessarily need to make massive profit with everything, you know? Micrpreneur.com does okay. My other businesses do okay. I can do some things that don’t… My blog makes essentially no money, you know?

Andrew: Yeah, I don’t see many ads on there. Do you have ads on there?

Rob: I have influads on there.

Andrew: Oh, okay.

Rob: I don’t know if you’ve seen it. Yeah, it makes…

Andrew: That’s one ad at a time, I think, on the site, right?

Rob: Between $50-100 a month. It’s more to help…

Andrew: How are you doing overall?

Rob: Good. Yeah, I don’t talk specif– Well, a few hundred grand, if that.

Andrew: A few hundred grand. More than you made before, when you were doing $200,000 as a consultant.

Rob: Top line, yes. Like all my businesses’ top line? Yes. Last year I reinvested a ton of money back into the business. I bought hittail.com. I paid for a designer. The design was not cheap. All that stuff. Depending on how much I want to pull out, I can make a varying amount. But yeah, I’m comfortable. I’ve been plenty comfortable for ten years.

Andrew: I remember seeing… One of the things I was doing is I was checking out your wife and I remember seeing to see, “How does she feel about her husband controlling this?” Being at this conference. And I just saw this feeling of both pride and also peace. And I remember even when I used to do Mixergy live events where we would just have drinks and stuff, I’d always be nervous. She was just at peace. You guys were just comfortable. The environment just worked. I’ll tell you my favorite part of MicroConf and then you tell me if I missed anything. I know I missed a lot from the pre-interview notes. You tell me if there’s anything that we should specifically go over. But I’ll tell you my favorite thing.

Rob: Sure.

Andrew: We just got back from having dinner with Ramit, Shawn Ellis, who came to do an interview but I couldn’t get him to talk specifically about his marketing tactics, Eaton Shaw, Noah Kagan. We were all just having dinner and then three of us went back to my room with Coors Light, just like cheap beer, and we just sat there and we talked about, I won’t even say who was necessarily in the room, but which of their sites really sucked and how it sucked. What they did that I promised never to tell to really get customers and I realized that I couldn’t even necessarily do on Mixergy yet. I’d have to wait ten years for those tactics to appear here in the interviews but I got to have those conversations in person and the same was happening throughout, whether it was at the bar, whether it was in the back of the room when we were sitting in between sessions talking over our laptops with some of the guests.

That to me was the, I like conferences like that. I’m going to go to big conferences, I’m sure. I prefer the smaller conferences where you get to actually talk to everyone, where the guests get to talk to every speaker if they want. Anyway, that’s MicroConf.

Rob: Yeah, we’re sold out this year.

Andrew: I’m glad you’re doing it again.

Rob: Thanks, yeah. Maybe in the future we’d love to have you back as a speaker.

Andrew: Yeah, I’d love it. It was painful for me to say no, that I can’t come back but I really need to focus on just organizing everything here or else nothing’s going to work.

Rob: I certainly understand that.

Andrew: So did I miss anything that we should be including in the notes, from the notes?

Rob: I don’t think so. I mean, I think the big take away or the big thing that I say when I speak is that I think people learn from successes and from failures. There’s often debate about that. I don’t think you learn just from one or the other or don’t learn from one or the other. I think my story shows that it’s pretty much, you’re going to have to fail and you’re are going to have to get back up on that horse and do stupid things that you learn from because without doing those things, if I had quit after the first failure or even after the first success, I wouldn’t have known what I know today, frankly. So that’s about it.

Andrew: I’ve got a note here. This is something that I should read. Your second child was born. You worked two days a week and could stay at home with him for five days, that when you want to spend some time doing things that aren’t work. I admire as an entrepreneur, not just that you get to do this. A lot of entrepreneurs get to do this but that you get to do it and the company doesn’t fall apart. It keeps on going.

Rob: Yeah.

Andrew: All right. So let me say this before I say thank you and ask where people should go, I want to just do a quick plug for Mixergy Premium. If you liked this interview and you say Andrew, give me more specifics or give me more tactics. I’ve got tons of them. Rob came and did a course on marketing. All these businesses did better and better as he learned how to market. If you want to learn the tactics that worked for him, the ones that he teaches others, the ones that he taught Ruben, that got Ruben, our mutual friend, customers before he even launched and will do the same for you, go to MixergyPremium.com. It’s all part of your premium membership.

You can just go and watch it. Hopefully it will be up by the time we post this interview and if it’s not, it’ll be up soon afterwards. Mixergy Premium, sign up and get it and if you’re already a member, you’ll get it. If you’re not, sign up and get premium service. MixergyPremium.com. Where can people connect with you?

Rob: Well, you know, my blog is probably the biggest corpus of content. It’s at SoftwareByRob.com and that’s where I talk about day to day the things that I’m working on and I try to divulge as much as is humanly possible to try and help others along the way. And then I’ve also written a book that kind of is a little more rigorous than my blog. It has more tactics and stuff and that’s at StartUpBook.net.

Andrew: StartUpBook.net and it’s SoftwareByRob.com. That’s where I first read your stuff years ago. It was so cool for me when I got your email and I said wait, let me make sure. Is this really the same domain name? Is this the same guy whose drawing of whom I saw on his website and it is and it was cool to hear from you and it’s great to have you on here. Thanks for doing this interview.

Rob: Yeah. Thank you so much for having me.

Andrew: Thank you all for watching.

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  • http://startuplift.com/ Pranaya

    Great interview Andrew. It’s interesting how we still forget Marketing and go after the Product first. WIth many failures before his success, Rob is truly an inspirational guy. 

  • Anonymous

    Hi Andrew, I haven’t finished the interview (currently listening). I’d like to see some interviews for those of us that are clueless about starting up. I’d like to see if you can possibly bring back some guest that are willing to go further behind there success. When money started to roll in, how did they set up their business structure, i.e. setting up bank accounts, business structures (S Corp, LLC, DBA, Sole Propietorship). When should you trademark? Or should you trademark.

    I’d reached out to a past interviewee, Cameron Keng (awesome guy by the way), He quickly responded to a question I’d asked about incorporating. I’m proposed to increase my salary by only $20k this year, and he advised that get a DBA would be sufficient enough until I grow more.

    So I guess I’m asking, if possible, if a consultant could come on and analyze the structures and set up of some of your most famous guests.

  • http://mixergy.com Andrew Warner

    I like his marketing-first approach.

  • http://collaborable.com/ Eric Ingram

    I knew this would be one of my favorite interviews from 15 seconds in. Thanks Andrew! P.S. more like this :)

  • http://mixergy.com Andrew Warner

    You want to know how they structure their businesses and about their trademarks?

    Anything else?

    And, didn’t Cameron cover that?

  • http://mixergy.com Andrew Warner

    ;-)

  • http://www.JiansNet.com Jian

    Nice, I’ve been listening to their podcast all along, will listen to this too. Thanks Andrew and Rob.

  • http://zapier.com Wade Foster

    I’ve been waiting for this one and it definitely didn’t disappoint. 

  • http://www.edmi.ca/ Amin

    This is one of those interviews that I’m going to watch over and over again… “find a niche and serve a purpose” … simple ideas, but incredibly motivating! Thanks Andrew and Rob. 

  • Anonymous

    Best interview ever. Haven’t watched the interview yet, but i already know. Rob is that awesome

  • http://mixergy.com Andrew Warner

    Glad to hear that!

  • http://mixergy.com Andrew Warner

    I need more guests who generate that kind of enthusiasm.

  • http://twitter.com/NathanGilmore Nathan Gilmore

    Yes!  Another bootstrap story :)  

    Good practical advice from a solid entrepreneur.  Great work guys!

  • http://mixergy.com Andrew Warner

    Yeah.

    I didn’t realize it took Rob so long to build his company. For some reason, even though I heard his story before, I just assumed he built everything quickly.

  • http://matthewritter.net Matt Ritter

    Rob was right-on about the ‘hole in the market’ for advice on micropreneurship.  Mixergy, due to the huge general diversity, has some great resources on it.  I’ll +1 for more!

    To be specific:
     – Marketing for people without a marketing department, or even a full-time marketer
     – Identifying that a niche can be cracked by a microstartup
     – A dissection of one of the most common failure modes: creating a product that people use, but don’t value quite enough to pay for.

    Thanks, 

              -matt

  • http://mixergy.com Andrew Warner

    Thanks!

  • http://twitter.com/TarekDemiati Tarek Demiati

    Nice one Andrew, you should invite Micropreneur more often, even if they’re not make millions,
    making 200k working in pyjamas from home is a nice lifestyle business that many employees with regular jobs would dream to have …

  • Anonymous

    Great interview

  • http://www.JiansNet.com Jian

    By the way, I feel relieved that it is not just my wife not giving me money to fund my startup ;-) On the other hand, I think it is good that there is a check and balance there so that I don’t over-spend. Every dollar needs to be justified, which is good to be nimble and frugal, keeping cost low while keep growing the profits.

  • Martin S.

    Seconded. More material for legal & accounting nerds, please!

  • http://www.bidsketch.com Ruben

    Loved the interview! I’ve heard Rob’s story before (and we talk all the time) but you guys did a great job and I found myself inspired :)

    Really looking forward to the marketing course as well. 

  • http://www.facebook.com/adam.clinckett Adam Clinckett

    Andrew, you dropped one of your best comments ever “One of the things I was doing is I was checking out your wife…” 

    I got a good insight into how Rob’s runs his businesses and why he goes into hibernation mode.  Definitely worth the long wait :)

  • http://www.JiansNet.com Jian

     Yes Andrew, more like this please!

  • http://www.facebook.com/people/Isaac-Guerrero/1661918433 Isaac Guerrero

    wow excellent interview, did not want it to end jejejjej

  • http://twitter.com/robwalling Rob Walling

    I thought that was a funny line as well during the interview :-)

  • http://twitter.com/robwalling Rob Walling

    Awesome; glad it resonated with you.

  • http://www.facebook.com/jwaldeck Jan Oliver Waldeck

    Right on Andrew and congrats Rob, you’re my new hero! :) I loved this story because I see myself in it.. I’m currently running 4 parallel projects, but still learning how to put some in “auto run mode” and focusing on what’s really important (like SEO, marketing and finding the right niche), which is usually a daunting task.

    From all the great advice I heard Rob give, I would love a little more info about getting the right Virtual Assistant (VA). How do you find those people you have to at the same time outsource and trust an entire business to? Elance? How do you “filter” the right ones? I’ve used Elance with some contractors and it has been quite interesting so far, just not sure I would trust someone I get there to run one of my businesses.

    Cheers! And congratulations again, this was very inspirational!
    jw

  • http://mixergy.com Andrew Warner

    Thanks. I’m still loving Zapier, by the way.

  • http://mixergy.com Andrew Warner

    I think you’ll like the course. We broke down the process you told me about.

  • http://www.ipyxel.com/ Tom Fang

    Terrific interview!

    When Rob started talking about maximizing the efficiency of this time, I was thinking that’s what I get STRESSED about all the time!  It’s our most precious resource and when I feel like I’m not using it properly, I get agitated.  I thought I was neurotic, but I guess I’m not alone.

    -Tom

  • http://mixergy.com Andrew Warner

    Thanks!

  • http://www.facebook.com/profile.php?id=1102787 Rachman Blake

    It’s exciting to see someone stick up for self-funded start-ups and “freedom businesses” Not everything has to be big and venture funded :)

  • Pradeep Sweetball

    Thank You

    The given information is very effective
    i will keep updated with the same 

    industrial automation

  • http://twitter.com/cmasonjar cmasonjar

    when rob said he had a kid and a mortgage, i thought “finally, someone i can relate to!” best mixergy interview i’ve heard in a while. rob did a great job giving specifics on his tactics which was great. 

  • JB

    Very cool information  , but I was curious to know what happend to the beach towel company? Does he still own it or did he sell it and if so for how much ? and why if it was an easy drop ship biz? Good interview.

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  • http://mixergy.com Andrew Warner

    I didn’t realize how much of a demand there was for this kind of interview.
    I need to find more founders like Rob.

  • http://twitter.com/my_chiguai Michael Wills

    Definitely. Rob presents a path for more of us. Even if eventually people want to become a VC backed @500:twitter  startup (which would be cool), the process of gaining business skills when starting from 0 are critical. Plus the other realities of life as @twitter-8039722:disqus  mentioned. It’s spot on. Rob and founders like him represent a more sane path than “150% all the time burn burn burn” and by default it has the potential to be #lean since it’s self funded. We can’t do that without sacrificing relationships and people that are more important. It’s entrepreneurship for regular people. And @twitter-88757153:disqus is right as that it can be a big step up for a lot of people, myself included, and it eventually could lead to a funded venture.

  • http://twitter.com/my_chiguai Michael Wills

    I haven’t watched yet but one of the popular #sxsw quotes I really appreciated from tweets was “the overnight succes takes about 2 years”. Paraphrase is mine but I am not sure who originally saud it.

  • http://twitter.com/my_chiguai Michael Wills

    Oh I will definitely want to see the marketing course as well!

  • http://twitter.com/my_chiguai Michael Wills

    OT: First I’ve heard of Zapier. Looks quite interesting. The blog is awesome with the tech info. Thanks for mentioning it @AndrewWarner:disqus !

  • http://twitter.com/my_chiguai Michael Wills

    @twitter-86174269:disqus you mentioned for marketing first you would have made a landing page with the first idea. We can do that with something like @launchrock:disqus of course, and perhaps this is in the marketing course, how do you write it? What do you say since you just got the idea? Just put up the USP of the idea?

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  • Paul

    Excellent – sometimes listening to the guys making mega millions seems to remote – this makes the dream real

  • Anonymous

    I actually listened to this interview a few days ago but I had to wait until I’d calmed down to come and post this comment for fear of dropping my second f-bomb in as many comments.

    Rob: that was amazing and inspiring stuff. I’ve been following your blog since listening to Ruben’s interview and course (he mentions you in both :) but it’s always a totally different vibe to hear the full story “in person”, so to speak – thanks heaps for taking the time to do the interview and share so much not only here but also in the stuff you’ve written on “micropreneurship”.

    Andrew: I forbid you from ever attending SXSW again – it’s so good to have you back and posting interviews. In your absence I had started going back to the your really old interviews and whilst the guests are still high calibre you’ve DEFINITELY improved as an interviewer :) I didn’t realise how much I’d come to depend on my daily “mix fix”.

  • Martin

    Hi Andrew,

    is this course already available? I can not find it…

  • PS Nanduri

    Andrew, 

    This is nice one by Rob.
    Also, I cannot resist but say this. The guy that posted the comment right above , Startuplift.com (Pranaya) looks interesting and seems to be microprenuer himself. His idea seems brilliant, may be worth interviewing or checking.

  • http://mixergy.com Andrew Warner

    I’ll check it out.

  • http://mixergy.com Andrew Warner

    ;-)

    It’s not SXSW’s fault. It’s my fault.

    I couldn’t get enough guests lined up for daily interviews. I’m going to hire an assistant producer who can help me find the kind of interviewees you love.

  • Anonymous

     If you’re interested in tapping some more Aussie talent I can introduce you to a bunch of folks. Email me: iain@workingsoftware.com.au

    Also just noticed this on the HN front page ;)

    http://news.ycombinator.com/item?id=3763499

  • http://mixergy.com Andrew Warner
  • Anonymous

    I can give you a list of Australian entrepreneurs you can talk to. Email me iain@workingsoftware.com.au if you want me to rustle one up.

  • http://mixergy.com Andrew Warner

    I’m checking out the link now.

    I’ll email you about Australian founders.

  • http://www.markzhang.me Mark Zhang

    One of the best interviews ever. Rob is very systematic and actually uses his experience to explain and teach.

  • http://mixergy.com Andrew Warner

    Thanks. It’s become one of our most popular interviews.

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