[10] Rob Walling Shares His Approach to Scaling a Portfolio of Startups
Okay. Let's do this. Hello, Bootstrappers. Welcome to Bootstrapped Web episode number 10. It's the show for business owners like you and me who believe that to get to where we're going, we have to learn by doing.
Brian Casel:I'm Brian Casel. You can follow me on Twitter at Castjam or on my blog at castjam.com. Today, you're going to hear my interview with Rob Walling. He's the cohost of Startups for the Rest of Us, one of my favorite podcasts out there. He's also founder of quite a few bootstrap startups.
Brian Casel:Most of you probably know his most recent ones, Hittal, and now his latest one, Drip, which is kind of being rolled out as we speak. I was really excited to have Rob on today because I think he has carved a pretty different path from most entrepreneurs. He really takes the portfolio approach to building businesses. Instead of starting just one company and growing and growing and growing that single company. What Rob does is he starts one, he scales it up, he puts people in place to run it, and then he moves on to the next thing.
Brian Casel:So that's what I dug into in this interview. I wanted to really understand how Rob goes about navigating one startup to the next. We talked about his approach to hiring, how he chooses what to do next, and how he's able to manage it all. So, and real quick before we get to the interview, I just wanna tell you about the book that I'm writing now, called Design for Conversions. It'll be coming out in a few months, but, but last week I put out a blog post called The First Steps to Writing a Book, and it covers in detail what I'm doing, to get this massive project started.
Brian Casel:So you can check that out at castjam.com, and you can get on my newsletter to get my weekly articles. Okay. So now on to the main event, my interview with Rob So I'm here with Rob Walling. Rob, welcome. Thanks for taking the time.
Rob Walling:Yeah. Thanks for having me on, Brian.
Brian Casel:Alright. So, you know, I'm sure they're not there aren't that many people out there who don't know you and and don't follow your podcast and everything that you do. But, for those who don't, maybe a a brief introduction, who you are, what you do.
Rob Walling:Sure. So, my name is Rob Walling, and I got started kind of, publicly, with my blog, softwarebyrob.com. And that's been going for about eight years. I don't blog nearly as much as I used to, but, I I guess I consider myself first and foremost, a founder a founder of things. And so, you know, I work on web apps mostly, but I also have these these other things.
Rob Walling:The the blog I just mentioned, the podcast is called startups for the rest of us, and that's been running for three or four years. And then, I wrote a book called Start Small, Stay Small, a developer's guide to launching a startup. That was a couple years ago as well. So I like to to dabble in a lot of things, but then I do like to hunker down and and focus on actual startups, you know, actual, for me, it's web because that's just what I know. But, that's kinda my primary job, and then I do kinda the mentoring and the teaching and some advising.
Rob Walling:And, yeah, I'm even started I've started doing a little bit of angel investing recently, which is fun. And I just I just, you know, enjoy enjoy doing all that.
Brian Casel:Very cool. So, I mean, you're you're you're kind of all over the place. You know, what what people really know you for, I think, are are like you said, your your blog and podcast and the conferences, MicroConf. Really sorry I missed that one last year, but I'm definitely gonna plan my entire 2014 around making it to MicroConf in Vegas for sure. Nice.
Brian Casel:So so I I I think your your current, startup that you're that you're really kind of focused on right now is is Drip. Can you tell us a little bit about that?
Rob Walling:Yeah. Sure. So, Drip is email marketing software, and its focus is on making, basically email sequences or you can call them email mini courses or auto responders. People have names for them. But it's about making the process of getting that set up just brain dead simple, instead of spending literally, you know, 8 hours trying to get something set up.
Rob Walling:You can do it in DRIP in in a few minutes. We have entire, like, blueprints for a sequence. So you just you click a button and it just spits out a five day course, and you have to just insert some content and poof, you're you're set to go. We also have a a pretty neat little opt in widget that allows you you install a little bit of JS at the bottom JavaScript at the bottom of your, footer, and it just pops up a widget on every page of your site. So right away, you're collecting email addresses without having to go and, you know, stick a a an HTML form in every page of your site.
Rob Walling:It automatically does a little toaster pop up kinda like an OLARC chat window or something. And so that's we've been focusing on that, or I've been focusing on that for about five, six months. The developer has been working on it for longer than that, and and we're we'll be launching here in the next month.
Brian Casel:Very cool. So, you know, I I think DRIP is, from what I understand, it's really one of of many little startups like that. You know, I mean, another one being Hittel. Can you tell us, like, like, quick overview or or list of of of the other startups that you've been involved in and and that are still running today?
Rob Walling:Sure. So so Drip, which I just talked about, that's at getdrip.com, by the way, if if anyone wants to check it out. HitTail, which is a long tail SEO keyword tool. Dotnet invoice is asp.net invoicing software. Apprentice Lineman Jobs is a job board for linemen, which are electricians.
Rob Walling:And to be honest, I have either those are the only four that I own right now. I just sold one called Wedding Toolbox, which was a b to c. I'm trying to get out of the b to c space is is what I'm doing. I'm I'm divesting my investments in areas that are not as lucrative as the b to b space and are just not as interesting to me anymore. And so some of these were great stepping stones.
Rob Walling:You know, early on when I was consulting, just had to I had to hit my number in order to to stop consulting. My my number in terms of product revenue per month, that was the goal. And I did anything and everything to do that. And so I owned a beach towel website called just beachtowels.com. It's I sold it a a year or two later for for good profit, and it's still it's way more successful, but it's still you know, it was doing well when I had it, it's more successful now.
Rob Walling:I owned a theming service called CMS Themer that I outsourced all the back end work. I had a I would you know, had an agency that would do it, and then I marked them up a 100%, and I would take the cut. And it was basically turn your PSD into a WordPress theme or some other Drupal and Joomla themes. Try there there are more, but maybe I'll I'll stop there.
Brian Casel:I mean, it's incredible. You know, just kinda going from one thing to the next to the next, and some are kind of living on in your portfolio of of businesses that you own today, but then some you you kind of unload. You you kind of alluded to it a little bit, you know, in in that you're moving from b to c and and really focusing on b to b. Is there is there anything that you think would kind of characterize the types of businesses that you tend to get into, like some kind of common theme? I mean, it seems like they're all really varying markets, but maybe there's something there.
Rob Walling:Yeah. Well, I mean, so they they are all web, to state the obvious. Like, I don't have any mobile apps or any desktop or any, you know, other type of of stuff so it there are web apps. The my focus has actually changed over time early on it was what can I acquire because I didn't so I had more money than time because I was consulting I was working a lot but charging a lot and so I was saying what can I acquire that I have knowledge that I can market? And so I didn't stick to any niches as you can tell by the randomness that I just named.
Rob Walling:As things have gone on though, I've been able to get a little pickier about what I acquire or what I build because I know that recurring you know, the value of recurring revenue, the value of having some marketing channels that work, the value of having an online audience for that niche, and, the value of, let's say, SaaS. Forgot forgot my next piece. And oh, b two b is the other thing. So so these days, yes, I do. When I look at an opportunity, I say, you know, does it have recurring revenue?
Rob Walling:Is it b to b? And for me, is it 10 x what I just did? Is it 10 times the size of what I just did or does it have the potential to be? And the only reason I ask myself that is because I get bored pretty quickly. And so if it's not gonna be 10 times the previous one, it's not gonna keep my interest at this point.
Rob Walling:So that may be something that applies to everyone but early on, yeah, I was doing ideas that you know if something could make me a thousand dollars a month, I would slap it in the portfolio And, you know, if I didn't have to spend any time on it, it was another thousand bucks. And I I won't do that anymore. It's just not it's not worth it. I'm in a different place.
Brian Casel:That's interesting. You know, kinda you you're not looking to double the income from your current one. You're really looking to to really grow beyond and and and get bigger and bigger.
Rob Walling:Yeah. And it's not it's not in order to grow the income per se. It's because there are different challenges when you scale to 10 x. Right? It's it's a whole different thing.
Rob Walling:You have so much to learning. I really I I took that StrengthsFinder two point o test, and one of I think my number one strength is I'm a learner. And that's also can be a curse because if I'm not learning, then I get really distant you know, kind of disenfranchised and and depressed and and upset with with what's going on. And so I have this constant need to find new new challenges, and that's that's more of why I tried 10 x rather than, oh, because I want, you know, 10 x the revenue.
Brian Casel:Gotcha. So how about, you know, your decision or or path that you've taken in in terms of building this wide portfolio of businesses, you know, getting involved in so many different things? Is that kind of, you know, what you're alluding to here with with constantly wanting to learn and and and and change and and grow versus, you know, the the I think the typical entrepreneur path, which is to say, you know, focus on on one thing, grow one company as big as it can possibly be, get to an exit, and then do something new.
Rob Walling:Right. Yeah. I think there are a few benefits to the portfolio approach. One is you're diversified really well, so that if if whoever, Twitter shuts down their API on you or Google decides to stop putting not provided for keywords or, you know, there's a lot of people that can basically wreck your business overnight and I've seen it happen. So having at least a few different businesses was always a safety net for me.
Rob Walling:I do tend to be somewhat conservative in terms of I wanna be able to pay the mortgage next month.
Brian Casel:Sure.
Rob Walling:And so I, you know, I have a pretty tight hold on that. The other thing is it does allow for varying it allow a lot of learning, I'll say. Just having having been in that many niches and having repeated my process over and over, I've learned way more than if I had started a company, you know, six years ago and I was still working in that company. It would night and day. Right?
Rob Walling:How much I've learned and how much then I'm able to pass on and teach on the podcast, on the blog, in my book, at the conference. You know? It actually makes me, I think, a better resource for the community. I mean, it makes me able to give that much more information because I can comment on well b two c is this and b two b is that. You know, I just have I I think it it allows me to have have more experience with that.
Brian Casel:Very cool. So let let's talk a little bit about, actually, let let let's get into, you know, your approach to bootstrapping. I think I think a lot of people know you as kind of like a champion for for bootstrappers. Why did you decide to bootstrap in the beginning? And why do you remain committed to to bootstrapping all the businesses that you're in it?
Brian Casel:So
Rob Walling:the reason I bootstrapped to start is because I had I had actually applied to Y Combinator in 2007. And I considered I we looked at I was in New Haven, Connecticut that year, and I was with a couple of of Yale MBAs. And they wanted to raise angel funding to build some ideas. And their ideas were were the big, you know, go big or go home type things. And I had some as well and we threw them all out.
Rob Walling:We talked to some angel investors. And I quickly realized that just the the startup lottery probably wasn't gonna work for me. I had a young son. I had a wife who was getting her PhD. She was very busy and it just I I didn't have eighty hours a week, and I couldn't quit quit my day job right away.
Rob Walling:So I realized that if I want really wanted to be in control of my time and I wanted to have more say in in my businesses and how my life looked that I needed to to bootstrap it. And so that was the original vision. Now at this point, I I now see the value a little more of of raising funding at a certain point in your business. I I will probably never raise funding because I don't wanna give up control. But, you know, if if you build a SaaS business to the point where you're able to acquire customers a lot less than than their lifetime value is worth to you, you should you should put millions of dollars into that funnel.
Rob Walling:You know? So I do see the the case for it. I I would never say don't raise funding, and I've never said that. I just think that if you want a certain quality of life and you want a a certain, you know, say over what what you do on a day to day basis and you wanna be able to not, you know, potentially get kicked out of your company or not be forced to. A friend of mine raised half $1,000,000 from from angels, and he may have an an offer to buy his company for I think it's it's like 5 or 10,000,000.
Rob Walling:And he's like, man, I would net, you know, 1,000,000 or 2,000,000 from that. But they won't let him sell. The investors won't let him sell because they want whatever, a 50, you know, a 10 x return, which would be a a $50,000,000 sale or something. And that's that's crazy to me. Like, I can't believe it.
Rob Walling:And he's working eighty hour weeks. And so it's not it's not all bad. I mean, I'm naming all the cliches here, I I really do have a friend who's going through all this right now. And I'm seeing that and thinking to myself, man, this this is why I remain committed to that approach because it's not worth it to me to to sacrifice those areas of my life.
Brian Casel:Right. Right. And and, you know, maybe even kind of thinking back to when you were first starting out, you know, and and, you know, so many other entrepreneurs who are kinda bootstrapping. I think a a big part of it, least, you know, very much for me is that I'm a designer and somewhat of a of a coder, not really, but there's so much that we that we have the ability to do ourselves. You know, when I'm thinking about an idea, I'm thinking, well, I I could build that.
Brian Casel:You know, I I could do it. I why do I need funding for that?
Rob Walling:That's that's right. And I think the other element too is, you know, if you don't live in one of these, let's say, six major US cities, maybe it's three major US cities, and if you can't work more than fifty hours a week because of life limitations, I and mean, there's a bunch of other things. If you can't do that, then then you can't raise funding. So bootstrapping is probably an option for the vast majority of of the world or, you know, definitely The US I'll speak to, but the vast majority of the world, whereas raising funding is actually only available to a tiny, tiny percent of it.
Brian Casel:Sure. So, you know, clear clearly, you've you've kind of built beyond just you, and you've built out your team. And so let's kind of talk a little bit about how you've scaled up your operation for a single start up, but but then to be able to actually manage multiple start ups at the same time. So maybe can you talk a little bit about your team? You know, what what is your team made up?
Brian Casel:Like, what are the roles that that make up your team? Where is everybody based?
Rob Walling:Sure. You know, my original vision was to be the the solo founder and not to have anyone working for me and about well, jeez. You know, a couple months in, I I got real pretty close with a designer, and he ran a small design firm overseas. It was in Bangladesh. And right away, he was doing a bunch of work for me.
Rob Walling:I didn't hire him as an employee, but I realized right away, like, I'm gonna need help with this. Right? My first hire was a virtual assistant, and he's no longer with me. But the way the team looks today, there are it depends on the month, but there are probably there are about six or seven people who do work for me in any given month, and they range from, you know, there's a couple different designers based on availability. I have a copy email copywriter.
Rob Walling:I have now a full time developer who was also the product manager of of another app, I moved him over. And then I have a couple virtual assistants, one of whom is will probably be moving to full time soon. And the countries range from United States, Canada, Mexico, Bangladesh, India, Philippines. I think that covers everybody. Oh, I had a guy in Iceland who just got a full time job, which was kind of a bummer.
Rob Walling:So
Brian Casel:All over the place.
Rob Walling:Yeah. That's right.
Brian Casel:Very much the the remote operation. Very cool. And so, you know, you have so many different projects, different team members. Are you is it pretty common that you would share that a team member would jump from from one business to another? Or you do you have, you know, certain people dedicated to HitTel or to Drip or to whatever?
Rob Walling:Yeah. So early on everyone was dedicated to an app and I noticed that I wanted the good people to do more for me. The people who really executed well and just did better than a better job at at their task than I would do you know. And so suddenly I was like, well, wait. Do you have any more time?
Rob Walling:Well, how much time do you have? You know? And and let's move you on to this next app. So that that has been nice especially standardizing on kind of the b to b SaaS space. There's a lot of overlap between these apps and I definitely can see I think everybody from here on that I hire will work on multiple apps.
Rob Walling:Although we'll focus like, we're focusing on Drip right now for the next, you know, I'd say, twelve to twenty four months. Really hard. And and HitTail's more. I mean, we're definitely supporting it and everything, but it's just not we're not building new features in it necessarily. But, yeah, I do see everybody will be doing some crossover.
Brian Casel:Very cool. So, kinda jumping back to, you know, you maybe the very first product that you did. What was that was that .net invoice or or something else?
Rob Walling:That was the first one that I actually started making any type of real money from. Yeah. I had I launched several apps before that, but they were just all failures. Yeah. I was following the dream of, you know, trying to launch some big b to c thing, they were just kind of flops.
Brian Casel:Cool. So, I mean, you know, we're back then, you kind of started out doing everything yourself, and you mentioned that the first thing that you hire that the first person that you hired was a VA. What were the fur what was, like, the first role that they covered? Was that, like, customer support? Or
Rob Walling:It was. Yep. That's the first thing. I mean, you know, if you're gonna hire hire someone, I would recommend hiring a virtual assistant early on and making them your tier one email support because that is even if it's only an email a day, it just it pulls your focus away, you know? You think it's only five or ten minutes, but it's amazing once you get someone in that role how how much more mental space you have to function as the founder and there's I know there's a bazillion excuses of why you don't wanna do it, don't wanna outsource your support, you don't wanna this and that But if you get someone good and you, you know, slowly ramp them up, you can start them a few hours a week and then, you'll be amazed at all the admin tasks that start coming across, you know, with any given app that you can then start handing to that same person.
Rob Walling:So now I have, I call him a virtual assistant, but really he's I mean, he's two one email support. He does some some, like, code installation for people, you know, JavaScript installation. I mean, he does a lot of different things, and he's it's amazing. You know?
Brian Casel:Yeah. Very cool. I'm I'm kind of at that point right now. I mean, I I have a a really great virtual assistant. He's been with me for for several months.
Brian Casel:But I I'm still handling the the direct email support, like, of it with clients, and then I'm kinda, like, forwarding things on to him. So I'm right at that point where I think it's time to really let him, you know, be the front facing.
Rob Walling:Yep. Yep. And you make the switch too because he will be the front one. And then if he can't do it, he'll forward it to you. And that's that's how you wanna, you know, do it.
Rob Walling:You become tier two email support, essentially.
Brian Casel:Right. Very cool. So now how do you go so from there, you hire a VA, they're handling the tier one support. How do you start building it out and ultimately outsourcing the entire operation so that you can focus on the next thing? How does something like HitTel, for example, go from you managing it to being able to put it on autopilot?
Rob Walling:Yeah. It it's a good question. I mean, bring up Hithtail, which is a good example, because earlier apps I had were weren't that complex. Right? So apprentice alignment jobs, I need new jobs entered.
Rob Walling:I need the payments all automated. Support is just email. And then I need people to come and sign up. But all of those things can be really easily automated with like a single virtual assistant. So that was that was a done deal.
Rob Walling:HitTail is more complicated. There are just more moving parts. There's there's a lot more customer. There's a volume of new trials and and all that. There's a lot of handholding that needs to go on there.
Rob Walling:So the the way that the way that I did it and the way that I would recommend and what I'll probably do doing for going forward is to well, there's two ways to do it. One is the the virtual assistant who I had handling tier one email support, he has taken on he just was so good that he started expanding his role, and he started doing more and more. And so he now handles all the front facing stuff, like dealing with customers. And there's there's not just email support in that. There's all types of you know, there's there's refunds, and there's payment issues and there's tons of stuff.
Rob Walling:And so he will pretty much handle all that. Now so I think that that your your tier one email support person could grow into that. And they just naturally know the business and they know how it works. And the more that they're able to do since they are handling the front facing the better. The second thing is, you know, with HitTail, there's this back end of there's code that needs to be written.
Rob Walling:There's new landing pages that need to be built. There are, integrations that need to be done if we wanna continue expanding, and there's marketing. It's not just autopilot marketing. You know? It's not some SEO page where I just get traffic every month.
Rob Walling:And for that, I actually went out and hired a product manager who was, he had he had launched a couple of of web apps himself. Neither of mid take had gotten traction, and, he lived locally, and I I knew him. And so I brought him on board to help with that kind of be it's kind of like the the successor to the founder. Right? Like you said, I was doing everything, and so I parsed some off to the virtual assistant And whatever, you know, he was able to do, and then anything that was more complicated than that, then I handed to that product manager who at the time was working twenty hours a week.
Brian Casel:Gotcha. I I mean, what does that really look like? I mean, is it is it the kind of thing where, you know, how how would you transition somebody into that role? I mean, they're essentially kind of taking over for you. And it's I mean, I'm I'm thinking about, like, making strategic decisions, you know, what to work on this week, what to say for for next month, which marketing tactics to to try.
Brian Casel:Sure. Mean, are they actually in charge of making decisions like that? Or
Rob Walling:Yes. Yeah. The product manager is the VA would wouldn't be, you know, he's more of a of a hands on guy. So the way that I did it, was two things. One, you have to know you can't bring someone in and expect them to make the decisions unless you train them to make the decisions.
Rob Walling:Right? They need to be apprenticed essentially. So I never just sent this big list of tasks and said, go do these. I always said, here's our list of tasks. Let's discuss which ones we're gonna do and why.
Rob Walling:And so it's kinda like if you think about it, it's like pair programming. You know, if you bring someone new onto your team, you you might pair program with them for a week just so they can see how you do things. You walk them through. You just learn so much from that. That's how we did it.
Rob Walling:Was it was more like, here here's the agenda, and here's the goals, and here's our marketing plan, and here's what has and hasn't been executed, and here's how I choose the next thing to execute. So he saw the whole process, and so now he can use that process as well. And, of course, runs to find me as needed.
Brian Casel:Gotcha. So, you know, you have you have these product managers in place, and, your past startups, or I mean, really kind of current startups, are running on their own, and now you're focused on drip, really kind of focusing on one thing at a time. How do you keep your finger on the pulse of all the other things going on while you're staying focused on on drip? You know, what what does that routine kind of look like?
Rob Walling:Yeah. It's it's not easy, but if you've if you get decent automation in place and you have good people then they will let you know when things go wrong. That's what it is. It's a matter of putting things in the hands of people who you've not just trained to be robots but trained to make decisions and they know you know we don't my policy is like if people ask for refunds we give them refunds always. All my businesses everybody knows that.
Rob Walling:So there's rarely a time where I get an email saying should we refund this you know I don't get I mean likely I would get a lot every week right because I'm sure there are refunds going on all over the place but I try to empower is the lamest word but it really is like try to empower them like make decisions and what happens is out of 20 decisions they'll make 19 of them the same way that I would and then they'll make one maybe that I don't agree with. Right? I would have done something different. But the fact that I didn't have to be involved in any of those 20 is totally worth that last that last one being made, know, quote unquote incorrectly or different than I would have.
Brian Casel:Gotcha. Very cool. And and I mean, are are you doing are you know, like, day to day? Is it kind of, like, weekly check ins or monthly, like, you know, strategy sessions or anything like that? Or is it really just kind of autopilot they're they're making those?
Rob Walling:For the most part, it's autopilot. They're making the decisions, and most stuff has been automated isn't quite the right word, but most stuff has been put in set in place that they can they can just go. And I have a dashboard, specifically with with HitTail and, you know, with Drip and stuff. I mean, I have a dashboard and I look at things, I can tell if something's high level is going wrong. And if something high level is not going wrong, if it's lower level thing, then then they'll handle it.
Brian Casel:Gotcha. I mean, does that does that happen? You know, downturns or or kind of, you know, marketing tactics that that kind of, you know, burn out after a while, you know, while you're trying to focus your time on on drip or organizing, like, micro conference something and then something goes wrong, I mean, what what happens then? Like, any any kind of tips here?
Rob Walling:Yeah. That's actually the point at which this begins to break down or this becomes a challenge, because someone can be trained to do things and even to make decisions and and move things forward. But when, you know, if the flames hit and Google just dumps you and suddenly you have no traffic or or your paid acquisition stops working or whatever, and I'm totally busy booking a conference and and trying to launch drip, it it does. That's kind of the worst, you know, I call it the, well, it's when the the it's just the worst of all cases. Right?
Rob Walling:It's when the the perfect storm I guess is the term for it. And what I've done in those cases is I will have to I have to pause something. I just have to trade and typically it would be I would in this case I would put drip on hold and I would go back and look and say, number one, is it worth fixing this? You know? Is it is it worth this, or can we live with this downturn for the next month while I go launch Drip and then come back to this?
Rob Walling:Is my time spent going back and fixing this now? Is it worth it, or is that time better spent launching the new app? You know? There there's this whole what's interesting is that since I've since each opportunity has been larger than the previous one, I have had some older businesses fail. But like I said, they might have been bringing in a thousand dollars a month, and then they crash and burn, they drop down to a $100 a month because something went wrong.
Rob Walling:Well, at this point, that's a negligible amount of money compared to what the other apps are bringing in. So really spending any anything more than, you know, a few hours on it just isn't worth it. So Gotcha. There's there's trade offs there.
Brian Casel:Right. Yeah. I mean, I I can imagine. But so let let's talk a little bit about about marketing. Going from one business to the next business to the next, are you kind of replicating the same strategies, things that you've learned from the past one into the new one?
Brian Casel:And then how, you know, how do things change from business to business? And then just over the years, how have your how's your mark you know, marketing approach changed?
Rob Walling:Yeah. It's it's def it's night and day compared to what it was. You know, early on, I had no marketing skills, and then I learned one of them. You know, it's like, alright. Now I know how to do AdWords.
Rob Walling:That was the first thing I ever learned. And then and I was like, okay. Next is SEO. And then I had two basically, arrows in my quiver, and that's all I could do. And so as I bought businesses back then, I only bought businesses that I knew I could market through AdWords and SEO.
Rob Walling:And that was it for a couple years. And then, I learned well, coming to to the second part where you said, you know, how has it changed over time? What's changed over time is now there's like, content marketing is a thing, and it wasn't really a thing back then. There are, oh, there are much better paid acquisition, things available today that weren't available five years ago when it really was just AdWords. Now you can do Facebook ads.
Rob Walling:You can do LinkedIn ads. You can do stumble upon Reddit. Mean, there are all these different networks that work. And so I've basically tried everything I can think of over these years and figured out if it's gonna be viable for for each app. I now have a big list.
Rob Walling:It's a big marketing plan, and it's just a template that I copy to the next app. And then I think through each one and said, boy, that approach gonna work? How, you know, how do I need to tweak it, or is it just not gonna work in this market? And I go down, and that marketing plan then is what I start executing on from day one. Again, day one for me is when code is starting to be written, not when the app launches.
Rob Walling:Right? I've been marketing drip since last November
Brian Casel:Right.
Rob Walling:For for nine months because I've had a landing page up, and that's how you get, you know, four figures of of emails of people who want who are interested in it. So yeah. So all that to say, it's definitely changed as my as I've gained more experience in marketing and it's definitely changed over time as the Internet has changed. You know, there's just so many different different ways to market that you couldn't do five years ago.
Brian Casel:Gotcha. And as far as content marketing or or inbound marketing versus, kind of lumping all the paid acquisition together, AdWords, you know, all all kind of paid together. What which do you kind of prefer, or do you do, you know, both depending on the app?
Rob Walling:So I I do both. Paid acquisition is really nice because it's so you can get up and running so quickly and if you can make it work it it can be a big spigot and it's not a lot of maintenance that's kind of an automated approach. Now your ads do burn out there's a bunch of it's not completely automated, but compared to content marketing, content marketing is really, really hard. The reason is because you can find writers all over the place. But to find writers who are good enough to actually write content that people are interested in, it's very expensive and they're all busy because because metrics hired all of them.
Rob Walling:No. I'm just kidding. But like but there are only so many writers who are doing that quality of work and who even understand. And so the process I mean, I probably interviewed ten, fifteen different writers, looked at samples, spent a lot of time trying to find someone to help with Hittail content marketing and it was it was a pain to be honest. And now I do, I have an agency doing it and it's not cheap.
Rob Walling:So again, I do both but I I start with with paid acquisition these days. Yeah. Certainly. Well, I mean, SEO and paid acquisition and, you know, there's other approaches too.
Brian Casel:But Sure.
Rob Walling:Content marketing is something that's not unless you're gonna write all the content yourself, which is very time consuming, it's not something I think you can automate early unless you have a a pretty big budget.
Brian Casel:Yeah. Sure. I mean, that's that's definitely, you know, something that I deal with with Restaurant Engine, where it is almost all content marketing at this point, and I have, you know, really great writers on board. And, I mean, that you know, we we've kind of systemized it to the point where they're actually coming up with all the topics. And and I'm I'm approving it.
Brian Casel:I'm I'm checking in. But, I'm working on that systemized approach where these topics can be generated, and and, you know, really in-depth articles. But it it it is a struggle. I mean, I I I do feel to a certain extent it would be better if I had the time to spend, really writing everything, but, you know, I don't. So it's
Rob Walling:It's probably the right choice because it's it's a lot of time that you could be spent doing something else. And there are there are good writers out there, you know. If you have them working for you, that's great. It's it's finding them that's the hard part. Once you have the writers, you're you're dialed in.
Brian Casel:Yeah. Totally. So how do you kind of decide which business or idea to pursue next? You you you know, you talked a little bit about how you go for 10 x. How does that factor into how you evaluate different opportunities, ideas?
Rob Walling:Yeah. The 10 x thing I mentioned too is only mean, I've only been doing that for, you know, the last couple of years. And it's got to stop at some point because unless I want to raise funding I'm not gonna be able to do something 10 extra upsize. I don't think so. But the the criteria so personally I at the beginning of every year, I look out and say, what do I think I'm gonna accomplish in this year?
Rob Walling:And so at the beginning of this year, I said, I know I'm gonna launch drip. I know I'm gonna put on microconf in April. And I'm thinking about either writing a second book or revising my other, you know, start small, stay small that I already released, doing a second edition. I had a couple other things on it too that and some of the things, you know, I get halfway through the year and it's like, poof, that that took way longer than I thought, and I have to eliminate some stuff. So me personally, that's how I do it.
Rob Walling:I think in terms of business ideas in general and business idea evaluation, the I'll tell you how I do it, I think this applies more to other people is I always start with a group of people and I ask the question, know, what problems do these people have? So I have this this black notebook that I keep and I this year or last year I wrote down, you know, what problems do entrepreneurs, startup founders, software, folks, what problems do they have and made this big list of problems. And that was it. I didn't make any talk anything about solutions. I didn't talk about they need a wiki or they needed this.
Rob Walling:Like what problems do we have? Because I'm pretty in touch with that market. I'm one myself. Like, there's a lot of benefits to to staying in that space. And then I went down and started coming up with, you know, solutions, and I just frankly started picking the one that I thought, or started investigating the ones that thought were most interesting.
Rob Walling:I do have a little bit of a luxury of being able to do that. I don't have to go after the market opportunities, which a few years ago I did. I I really focused on market opportunities because I was just trying to get to the point of, you know, quitting the salary gig and quitting consulting and then and then moving on. But these days, I do think having interest helps. It's not a requirement, but having, like, a passion for the idea is a good thing.
Brian Casel:Gotcha. Yeah. I mean, I was I was reading the latest post from Nathan Barry today, and that's you know, it's he was really writing about staying within the space that you're that you're in. You know, he he's kinda transitioning from all these different apps to focusing on things for marketers, designers, developers. Is that kind of where you're going as as well?
Brian Casel:I I mean, I I mean, obviously, with, like, MicroComp and and, I mean, DRIP is for marketers and HITEL, you know, are are you kind of focused on entrepreneurs? Or
Rob Walling:I think so. You know, you can tell I'm not totally certain about it. But we'll see what I've done in the past, I've acquired a lot of apps and I would acquire an app if there was a good reason for me to do so and I didn't really care about the niche it was in. But now that now that I'm able to or you know, decided to build one, then, yeah, it's a no brainer for me to build it in this space because I can see the the not the opportunity. I can see the need, to be honest.
Rob Walling:I it was an easy it was a one of the most common complaints I heard was about trying to get set up on Mail chimp or Constant Contact and how you couldn't split test in sequence you know, email sequences and blah blah blah. And so I started making a list of, I think I can fix all these things. So, yeah, I do. I mean, if I continue to build apps instead of buying them, then I probably will stay in this space because it, you know, it is one that I know.
Brian Casel:Gotcha. So just a few, you know, kind of quick questions about the podcast and and and conferences. So, you know, you and Mike started Startups for the Rest of Us, one of my favorite podcasts out there. I highly recommend everybody listen to it if they're not already. So what what led you guys to getting together on that and and starting it?
Rob Walling:Well, we've both been blogging for several years, and I had started listening to podcasts and just realized right away that that there's so much more engagement when you sit there and have someone in your earbuds you know while you're doing dishes or whatever. And frankly I listened I'd read Joel Spolsky and Jeff Atwood for years but as soon as I heard them do that original stack exchange podcast or stack overflow or whatever it was called in the early days that kind of blew my mind. Was like, wait, I feel like I know these guys even though I've been reading them for eight years. And so I decided like if I'm gonna if I'm gonna be in this space and I kinda wanna, you know, keep moving up in terms of, authority and influence and that kind of stuff. I wanna be a player here.
Rob Walling:I wanna I wanna do it. I wanna get out ahead of the trend. And frankly, in 2000 when we started, 2008 or '9, probably '9, you know, people were saying podcasting was done with, that it was never gonna catch on. And so we there was nobody. There were no startup podcasts.
Rob Walling:Mixergy wasn't around yet, you know. And so I do feel like we we had a and we did have a decent, probably a year where we were just kinda toiling away with, you know, less than a thousand listeners just kinda doing it. And then it really started picking up in, you know, 2010, 2011.
Brian Casel:Yeah. It's interesting, you know, with podcasting. I still feel like even today in 2013, it's it's I mean, it's obviously much much bigger and much more mainstream today than than it was a few years ago. But it's still, like I feel like there are people who who love to read all the blogs, but they just haven't tapped into podcasting.
Rob Walling:I know. It's really interesting. I kept waiting for that other shoe to drop because, yeah, there's a lot there's a lot there.
Brian Casel:Yeah. I mean, I talk to other entrepreneurs all the time and I'm and I'm always referencing, you know, Startups for the Rest of Us, this episode or that or that mixergy and they're just, you know, they they read all these blogs, but they're not aware that that all this amazing content out there really exist if if you just open up iTunes.
Rob Walling:Right.
Brian Casel:Very cool. So okay. So so, you know, the podcast has been around for a couple of years. And then, I mean, you also have the the course, Micropreneur Academy and and the conference. How did those two kind of come about?
Brian Casel:I mean, they were they planned from from the beginning of the podcast or did they come later? Or
Rob Walling:So the Micropreneur Academy was before the podcast. Okay. Yep. I launched that first and then the podcast was kind of an extension. Mike and I are co owners of of the Micropreneur Academy.
Rob Walling:I launched it first and then brought him on, you know, six months in when I needed I was in over my head and so the podcast does it loosely ties into it but more so the the academy was just because I was getting more questions than I could possibly answer via email and I some of the stuff I wanted to do I couldn't put in print like you needed a screen cast or you needed audio or you needed some other format And so that was why we wanted to do a membership site or I wanna do a membership site rather than just write a book or something or write a bunch of blog posts. And then there's a forum part of that as well. I wanted to build like some type of community and that, you know, that's happened. And then originally, MicroConf was just gonna be I wanted to get everybody in the Micropreneur Academy together in one place physically. That was the goal for it.
Rob Walling:And so we just, you know, got a a a room at the kind of a ballroom at the Riviera in Las Vegas and just threw it together and put tickets up for sale and didn't sell as many as we thought that first year. It was tough. You know, we were trying to get people to come. But, since then, it's really picked up steam and become kind of a it's definitely made a name for itself, you know, in this in this space.
Brian Casel:Yeah. Definitely. Now you guys are doing a second one this year in in Europe.
Rob Walling:That's right.
Brian Casel:Very cool.
Rob Walling:That's right. Couple months in Prague. Yep.
Brian Casel:Awesome. So now how how does, you know, doing things like this, having the conference, the podcast, really being out there, how does this stuff, impact I mean, you know, there these things are businesses on their own, of course. And and, I mean, it you know, it's an amazing community. But how does it actually impact your other businesses? You know, DRIP, HITTEL?
Rob Walling:I think well, so I'll tell you with with Hittel and .net invoice and everything I've had up to date, it's it's a rounding error like no one I mean, people come and check it out, but it's not doesn't make a difference in the business very much. I think drip could be different, because I think drip may be an even tighter fit with the audience. But I still don't plan on I would never plan on using or counting on that as being like a big driver of of sales because that it'll again, it'll it'll get you tens of customers, you know, from from your audience and and people over time. I mean, it's nice certainly nice to the the the bigger benefit, I guess, I'll say, is not getting new customers. It's it's that I have, like, an early access list right away because I was able to just email a bunch of people that I know, and I only know them because of the conference podcast blog and and the other stuff.
Rob Walling:Right. And right now, people are really willing to help me out. I can see people retweeting stuff. I see people telling other people about drip. They just they feel like I've given to the community, and therefore they wanna, you know or or I've given to them, frankly, and they wanna help me out.
Rob Walling:So I think there's more value in that aspect of it of just relationships rather than thinking like, yeah, I'm gonna get how many hundreds of customers am I gonna get out of out of my audience? Just because, frankly, the personal audience hasn't ever made a difference in in any of my businesses, and, you know, I'm gonna grow with with other channels, to be Yeah.
Brian Casel:That I mean, that's interesting. I mean, I I certainly found out about HitTel and Drip, just from listening to you guys. I mean, I I think it's interesting just hearing your updates and and, you know, things like that. So, I mean, I can kinda see how how some audience members might not find out about those things otherwise. But, you know, that that's really interesting how you talk about you know, it's great for those early access and and, you know, early interview customers.
Brian Casel:I mean, I I hear that question a lot, and I've struggled with this myself, is finding really high quality target customers to have those initial conversations with. Yep. And
Rob Walling:if you work your network, that's the way to do it is to work the network, you know? Yeah. So really talk to the people you know. It's way easier. And then they cut you a lot of slack early on.
Rob Walling:You know, you get the first person in and then the thing crashes. But you you know the person, you know. It's not just cold cold contact.
Brian Casel:Yeah. I mean, you know, building that building that audience is not it's not so much about having someone to sell to. It's they're they're also gonna help you create the product and and really get on the right track. So
Rob Walling:Yeah. That's right.
Brian Casel:Very cool. So, you know, one more question, which I ask, every guest. What what is really challenging you right now? I mean, people look at someone like you, you know, you know, clear, success stories in in all these startups, but there's there's gotta be something that that is actually challenging you right now in in 2013. So what do you what's what's challenging you and what are you doing to kinda work through it?
Rob Walling:I am being challenged because I'm I'm at a place where I've never been before, where I'm about to launch an app that is bigger. It's in a more competitive space, there's a ton of email apps, there's a ton that are launching, ton of other startups out there. And I, you know, I've always had a very small team and I very well may need to hire two people here in the next couple and maybe hire a couple more later. Like I'm that's what's challenging me is figuring out can I keep doing this the way I've been doing it for years or have I gotten myself into a market where I need to change my game? I need to change up some of the decisions I'm making because they're just not realistic anymore.
Rob Walling:So that's what I've been spending a lot of time thinking about.
Brian Casel:Do you mean in terms of marketing and and and going up against competition? Or it's just
Rob Walling:It's not the marketing. It's moving fast enough. Like, you only have two people working on an app, you can't build features. You can't do integrations. There's there's certain things you just can't do quickly enough that if I'm seeing right now if if, let's say, someone raised half $1,000,000 and hired a team of of six or eight, which they could do pretty easily, you could you could outrun us.
Rob Walling:And and it's in a competitive enough market that I think that might happen. So that's where I'm you know, I'm not saying I'm changing it or not. I just haven't made a decision, but I'm trying to figure out how to do that, how to navigate that, but still stay true to to what I wanna be, which is a really small team of talented people and that I really have a great time working with and that we don't have to work seventy hours to try to compete with someone else.
Brian Casel:Very cool.
Rob Walling:That's my challenge for sure.
Brian Casel:Awesome. And and so what is what what's up next on the radar? What what are we looking at in terms of Drip, in terms of, like, a full launch date, and what's happening after that?
Rob Walling:Yeah. So Drip has about there's about 30 people inside right now, and, that's early access. And then I'm gonna do a prelaunch to about 200 of the email addresses on my list. It should be about two weeks from today, hopefully.
Brian Casel:And this will be publishing on on Monday. So
Rob Walling:Yep. So two weeks from a few days ago then when it publishes. And then the full launch well, then I do an email launch to that. There's 2,200 on my list. So the the other 2,000 will come probably in about three to four weeks because I'm sure this first 200 are gonna have a bunch of stuff that we need to fix, you know, and and get changed and stuff.
Rob Walling:So it will be sometime in in late August, early September, hopefully, that everyone's in. But then I'm not gonna open the doors right away. I mean, I'm gonna let those 2,000, you know, or however many of them get in, figure stuff out. So I like to take things slowly in stages, and I think that's part of being a very small team is that we can't just let in thousands of people. You know?
Brian Casel:Very cool. Great. Well, Rob, you know, thank you so much for for taking the time. I definitely learned a lot. I know I know the audience will.
Brian Casel:So where can people kind of, you know, connect with you and and and reach out?
Rob Walling:Sure. Yeah. The two best places are software by rob.com and start ups fortherestofus.com.
Brian Casel:Awesome. Well, Rob, thanks again, and, talk to you again soon.
Rob Walling:Absolutely. Thank you for having me on.
Brian Casel:All right. So that was a great conversation with Rob Walling, and there were definitely a few key takeaways that I think are really important to focus in on. So let's go through those real quick. So the first one, Rob starts by putting VAs in place to handle that those those tier one support requests, which, you know, really a smart thing to to start outsourcing, you know, those those smaller parts of the business. But then, you know, he scales up to the point where people are in place to run all aspects of the business.
Brian Casel:That includes a dedicated product manager who has been trained to make strategic decisions the same way that Rob would. So, you know, he mentioned how his product manager for for each of his businesses, like like for Hittel, for example, you know, he he said that that he would make 19 out of 20 decisions exactly the same way that Rob would make those decisions. And even if one of those decisions is made, goes a different way, that's okay. Because it's worth it for Rob to have that freedom to focus on his next thing. So that's just a really inspiring takeaway because it kinda gives me, and I'm sure it gives a lot of you, something to strive for in terms of systemizing and putting your business on autopilot so you can kind of focus on the next thing.
Brian Casel:The next key takeaway here. One of the factors that Rob looks for when he's deciding which business ventures to take on next is whether or not this new idea would whether or not it could 10 x his previous venture. So he's always growing, always challenging himself. That's the kind of thing that really shows how far Rob has taken his entrepreneurial path. So, again, very inspiring.
Brian Casel:The third takeaway here, it sounds like Rob's ventures are trending away from the b to c space and now focusing on b to b. But to take that further, his latest ventures tend to be marketed towards entrepreneurs and marketers. You know, so this is kind of in line with the thinking of of Nathan Barry and and Brennan Dunn. You know, I I talked about Nathan's post on on his blog today, and and I'll link that up. You know, the key takeaway here is that if you're looking to take the portfolio approach, building lots of businesses, not just one, then it probably makes the most sense to focus your energy in on one particular space.
Brian Casel:You know, one the space that you're most passionate about. And then you can have all of your products are are really kind of related. And it's easy to cross sell. It's easy to create content that because you're passionate about the space, and build a single list, you know, like the way Brennan Dunn has has done. So, you know, definitely an important takeaway to to think about there.
Brian Casel:And finally, fourth takeaway here with my conversation with Rob was the kind of the hidden benefits of building an audience. At least in Rob's case, benefit for him for building his audience through his podcast and and the courses and and and the conference, it isn't so much about building a large stream of customers for his apps. The real value of building such a large audience is it gives him an incredible network. He can look to his network to build that early access list for a new app, or he can look to his network to find a new hire or or get feedback or, you know, things like that. So, you know, this this really brings to light one of the biggest hidden benefits of of building, a a solid audience.
Brian Casel:I hope you enjoyed this episode. And if you're looking for more, head over to castjam.com. I've been writing a whole lot lately on the blog, especially as I'm getting started to write this first book, designed for conversions. So head over to cashmam.com, sign up for the newsletter, and you'll get my latest weekly article. Thanks for tuning in.
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