min to LISTEN
April 3, 2018

Rob Walling: The Stairstep, No-Bull Approach to Bootstrapping

Rob Walling
Rob Walling
Drip & MicroConf

For start-up marketing, how do you get something off the ground without outside funding? What’s required to launch a product?

Marketers and developers will learn a lot today!

In this episode, I’m talking to Rob Walling, a Web developer, podcaster, entrepreneur, and conference co-host about stairstepping your way up when it comes to bootstrapping.

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We covered:

  • How to launch a new software business without a lot of time or money
  • Stairstep Approach: Build something small, a one-time sale product; find source of traffic or niche
  • How to come up with useful product ideas for angles; use tools that show places that generate traffic
  • Make money online by knowing SEO practices
  • Optimize for an engine to provide a valuable resource for people searching for a specific term
  • By using marketing to get to the top or to get in front of people, only to let them down - then you will not have longevity
  • Utilize communities and marketplaces, online or elsewhere, that already exist and people are using
  • Gain confidence, experience, and knowledge to improve and make money
  • Process of building a simple plug-in: Research; come up with an idea; know where to go; teach yourself or outsource work; submit; and determine level of interest
  • Acquire something rather than building it from scratch; leverage other people’s work
  • Start something guaranteed to get traction by using an idea done before, several times
  • Determine if a certain number of people are looking for the same thing
  • Can you charge for it? Can you add something to charge for? Can you build something people are willing to pay for? Are you interested in building something?
  • Rob’s Goal: Provide value to people in exchange for money; take that money to quit day job
  • Identify that there are volumes of searches to sustain your objective
  • Focus on a landscape with a lot of products that are not good enough; competition validates the market
  • Go for the goal to rank #1; that’s the challenge
  • Niche-down results in smaller opportunities but that does not matter initially
  • Earning your first dollar is a life-changing moment, but it is still good to sell stuff; as the dollars get bigger, the more interesting it is
  • Rob’s passionate about being ethical and adding value to people’s lives and making money out of it
  • If you make money from an add-on, then launch more add-ons for diversification; if not, start over
  • You have an audience, grow it slowly, offer solutions to their problems, and make a living
  • Practice patience and maintain a long-term mindset; marketers get overwhelmed with the amount of day-to-day information available
  • Set long-term goals because choices you make today, stick with you
  • Marketers should learn to think analytically like developers; measure conversions, link dollars to spending on ads to how many people are buying, etc.
  • Developers can learn from marketers that a product is not everything; customers and marketing are directly related to the success of a product; and talk about the benefits rather than the features
  • Some marketers go for growth hacks - grow at any cost and just for the sake of it
  • Marketers have a bad reputation because of overstepping bounds of ethics
  • Good marketing goes unnoticed; bad marketing is in the news a lot
  • Have an opinion, stand for something, and be real
  • Define your enemy because when things get tough, fighting against it is the only thing that will keep you going


Full transcript:

Louis: Bonjour! Bonjour! Welcome to another episode of everyonehatesmarketers.com, the marketing podcast for marketers, founders, and tech people who are just sick of shady, aggressive marketing. I’m your host, Louis Grenier.

Today, we’re going to talk about startup marketing and how to get something off the ground without outside funding as a techie, as a developer per se. But it’s also very relevant for non-developers and marketers in particular who want to understand what’s required to actually launch a product, and what they can learn from developers. It’s ready for both marketers, developers and I think you’re going to learn a lot.

My guest today is a web developer, a prolific podcaster who has a podcast called Startups For The Rest Of Us. Himself and his co-host have recorded almost 400 weekly episodes so far, which is amazing. He’s a serial bootstrapper and entrepreneur for a decade now. His most recent company is Drip which is a lightweight email automation service. Finally he’s also the co-host of the startup conference, MicroConf.

You probably have guessed who my guest is today. I’m really excited to welcome Rob Walling on the show. Rob, welcome aboard.

Rob: It’s my pleasure. Thanks for having me.

Louis: You’re welcome. Let’s get started into the tough question because listeners really enjoy that I start with the meaty stuff right away instead of spending 20 minutes talking about stuff that don’t really matter.

Let’s say that we want to do something together. I’m a marketer, but I know nothing about software and you’re an entrepreneur and a web developer who has quite a lot of experience building successful product. So let’s say that together we’re working on a new business. It has to be a new software business. We have around $1000 in the bank. We want to be somewhat profitable within three months to six months, and we don’t have a lot of time to spend on that because we both have full-time jobs. We have 45 minutes minutes a day and the last part is you cannot use your name, your network to launch this thing. We’re basically starting from scratch with not a lot of time and not a lot of money. The golden question is how would we get started?

Rob: I have this concept called The Stair Step Approach to Bootstrapping and it’s to build something small the first time and typically it’s a one-time sale product, so I would not go into SaaS as a first time thing with all the constraints that you’ve named. I would look for some type of source of traffic that we could get in front of and that we feel like we could win and quickly rank in the top two or three.

I’m going to give you some examples. If one of us knew SEO, then I would look for an angle there. If one of us knows how to do the wordpress.org repository SEO, I would probably build a small WordPress plugin which we could totally do in PHP for 45 minutes a day if one of us knows how to code.

You can look in iOS App Store though that’s a little more crowded now. You can look on YouTube. You can look on Amazon. There’s all these sources of traffic that, if you are able to basically rank well and—you’re not going to be a millionaire, you may not even have a full-time living—but you can get something like a thousand, $2000 a month very quickly if you find that niche. I’ve seen this over and over and over in all the places that I’ve just talked about as if you provide some value, you can get it out there pretty quickly at low cost, 45 minutes a day.

Louis: That’s an amazing way of thinking buddy and I’ve heard that from your podcast a few times. Let’s dive in into this approach. I like it very much because it’s rooted in reality. It’s rooted in the fact that, you’re not going to be a millionaire unless you’re being extremely lucky, persistent, and patient. If you haven’t created a business before, if you’ve never launched a business before, or if all of your ideas in the past never really went where you want to go, you need to start small. You need to really start with something that you can easily pull off without a lot of time, and then move on from there, right?

Rob: Yup, that’s correct.

Louis: Shall we first of all explain how you typically come up with this one-off type of product. Where do you typically look to find an angle or ideas that could be useful for people?

Rob: I would actually start with one of these tools. It depends on where you want to go. If you’re going to do Google SEO then you’re going to want to go to either the AdWords Keyword Tool or you going to go to, is it Ahrefs that’s the big one now or Market Samurai? And these are going to try to show you places that you can potentially get some traffic. There’s Jungle Scout which basically is the SEO tool for Amazon.

Each of these has their own kind of niche tool and that’s where I would start. This is less about doing the traditional customer development approach where, if you’re trying to build a multi-million dollar SaaS app, then you need customers to buy into it, and you need to build the features they need and all that stuff. But if you’re just going at this angle—again, given the constraint—I wouldn’t do this today because I’m past this point. But if it was my first product, that’s what a bunch of my first products did.

One of them is called DotNetInvoice and it was invoicing software written in ASP.NET and this is back in 2005. I learned how to do SEO from scratch. I didn’t know how to do it and once I ranked for a few key terms the people were searching for and it was a very small niche. I started running AdWords. I got it up to between two and five grand a month, depending on, and that was a huge win for me. I had never really made a dollar online and that was just one in a series of sites that I rolled out. You want to go to the right tool for the right place that you want to go.

Magento add-ons can make money, Shopify add-ons, Photoshop add-ons. All of these things have these little marketplaces that, if you know someone who knows how to “game it”... Here’s the thing. When I say you’re going to “game it,” all you’re doing is you’re just optimizing for that engine, and you’re going to provide a valuable resource for people who are searching for that term. You want to build the best product and you want to rank high for it. If you’re going to build a shit product or you’re going to rip people off, then don’t bother doing this because you will lose in the end. That’s the whole point of this podcast. If you just use marketing to get to the top or get in front of people but you let then down, then you’re not going to have longevity.

Louis: Exactly. One thing I pick up from that you’re saying is you’re using communities and marketplaces that are already established and that people are already using. You’re not starting with nothing. You’re basically trying to plug in to networks that are existing, which is a very important idea because then you don’t have to invest in crazy amount of time, resources and energy to try to get people somewhere where they’ve never been before.

Rob: That’s right. You’re trying to draft off of their success, and certainly they win as well. All of these places that I’ve named, they’ll take a cut of your purchase or they get some benefit out of it. It’s not like it’s lose for them. These are ideas you start small with. You might charge $10, $20, $30 for each of these, maybe up to $50 or $99, but they are one-time sales and they’ll have a single sales channel, and they will top out, they’ll plateau and it will be very hard to grow past that plateau.

But that’s not the point. At this point you’re just trying to gain confidence, trying to gain experience, you’re trying to gain the knowledge of having done this once, and you’re trying to gain enough revenue that you can then, you’re not limited to $1000 because now you have a couple of grand coming in every month. Now you can do this again and you repeat it and you get better and better at it. I have seen people over and over and over do this with WordPress plugins and with these other types of add-ons, and eventually just level up to where they can buy themselves out of a job and pay their own way.

Louis: If you’re listening to this episode in 10 years or even 20 years, I still want you to get value out of it. What you’re saying is crazy important, Rob, and regardless of in 10 years time, in 2027, Google is dead, and Amazon is dead, and Magento marketplace is dead, we know for sure that there will be other communities, other places where people hang out, where you can do the same. It’s not about Amazon, Google, or anything. The principles remain. That’s one point I want to make to make sure the people understand that. It’s not about those quick wins that will work now or won’t work ever after. They will work if you focus on those principles.

For the sake of this story of this idea, there’s actually a plugin I would like to have for WordPress, which is a way to quickly turn a Google Doc into a WordPress post, something that will export all the images and all of that. Just to illustrate our points together into the step-by-step, let’s just pig this idea that says, “We’re going to build a very simple plugin that just turns Google Docs into a WordPress post. Does it make sense?

Rob: Yup.

Louis: Right, so we have the idea and we know now where to go because it has to be a WordPress plugin, right?

Rob: Right, yup.

Louis: Let’s say that I am a developer but I’m not really knowledgeable in this particular area, in building this plugin, or I am a marketer and I might know a few friends are able to build this kind of stuff. How would you go about it?

Rob: What’s funny is I’m just such the person who have technical skills but I haven’t really ever written code in several years. I personally, if I have less than $1000, I would Google how to build a WordPress plugin in PHP and I would teach myself how to do it. I don’t know that everyone needs to or wants to do that but that’s the kind of entrepreneur that I am. I want to learn this stuff that going to be core to the product. So that’s what I would do.

The other option of course is to post it on Upwork or to find a friend who’s willing to help you. If you have $1000 building a WordPress plugin like this, it’s feasible for that amount of money. It’s not going to be the highest quality thing you’ve ever built.

I think what you actually need is a free plugin and then you need to build a paid addon. That’s how you’re going to make some money. The paid addon will include support and it will have more functionality, a feature that’s not offered with the free plugin. That’s where you got to figure out if you can build both of these things for $1000 or you have to do some of the hacking yourself, this doesn’t have to be the most gorgeous PHP code and there’s a bazillion tutorials on how to get something like this out there.

Once it’s built, then you’re going to submit it to the wordpress.org repo, but before you do that, you’re going to research, “How do I rank well in this repository?” This is part of being an entrepreneur. It’s going out there and figuring out how to help other people, do they have info on this? Do I know any friends who have WordPress plugins that rank well? What did they do? Call them up so you work in your network, you work in the Googles, and you’re trying to get that think to rank for this term.

I would put out a really simple one at first. It does what you say it does but it doesn’t need to be super complicated or feature-rich because at this point you’re trying to find out is there’s enough traffic, is there enough interest in this term. Because as far as I know, there are the tools, the SEO tools for Google and Amazon and these other things, there’s no SEO tool for WordPress itself. You don’t know how many searches there are for “Google Doc WordPress” or whatever, although I guess you can look in Google’s to get a sense of it. That’s probably what I would do. Look in AdWords or Ahrefs. That’s where I’d start.

Louis: Let me maybe backtrack a little bit because I think I went ahead a little bit too fast on those steps. What you said that the very first step is actually not to come up with an idea like this and solving your pain point is more like searching for the amount of specific keywords, specific thing that people are looking for that might not be well-served because you might observe that quickly, you mentioned that you want to build the best product for this particular query almost, right?

Rob: That’s right. You’re trying to get in the way of the traffic. You’re trying to find the traffic. A friend of mine has done this where he will search for stuff and look for old plugins that haven’t been updated in a while but have quite a few downloads and that’s probably an indication that there are enough searches for that term, and then you can offer to adopt the plugin. Whether you take it for free or whether you pay the person $500 and use the other 500 to get a paid addon built, that’s up to you. But I have seen adoption and just taking it over from previous maintainer. It’s a nice jumpstart, but it’s the same reason that I have acquired several companies and websites rather than building everything from scratch because it gets you past that initial hurdle and that 6 to 12 to 18 months of building things.

Louis: Yeah. Once again, it’s using the same principle than using the existing traffic from communities or the existing popularity of marketplaces. It basically enables you to stop trying to build something from scratch and instead leverage what others have been doing before. It’s funny because when you think of entrepreneurship and launching startups and it’s getting very sexy nowadays launching your own startup, people are trying to find this idea that has never been thought of before? They try to find those crazy new software that have never been done before to be very original, but it seems like the best, probably one of the way you can really start something and be almost sure that this will get traction if you work at it, is to use an idea that has been done many times before that people are aware of, right?

Rob: That’s right. It doesn’t have to be boring but a lot of the best—like lifestyle businesses—what we’re talking about like businesses that actually throw off cash, are pretty damn boring. I’ve referenced DotNetInvoice before. Who really wants to build invoicing software in ASP.NET? It’s not that exciting but it was a huge jumping-off point for me.

If you want to go build an exotic startup and that new novel idea, then yeah you should probably raise some funding. It’s going to be really hard, your chance of success are very, very small and that’s great for some people. It’s all about the excitement. But for a lot of us it’s more about we want to build, we want a repeatable and an idea or a process that’s highly likely to be successful and actually work. For that, you got to start more thinking about where are people, what are they looking for and how to I build something that serves that need that I can charge money for? You need all those things in place in order for it to work.

Louis. Right. So let’s isolate two things. The first thing is you want enough people to look for something. Without talking about Google particularly or Amazon marketplace or whatever, it’s basically you want to know if a certain amount of people are looking for the same thing in a certain amount of volume. Do you have any methodology there to quickly know whether the search or the type of things people are looking for is worth pursuing?

Rob: I think the criteria I look at is a, do I think I can charge for this, or if this is a free thing I have to give away is there something I can add to it that I can charge for? Because if you can’t charge for it, you’re not going to make enough money on advertising, you’re not going to make enough money if you try to do a donate model.

There’s a bunch of models that work for these massive companies like Wikipedia or I think of Facebook. Those models don’t work at small scale because you just don’t have the volume. You make $4 a month on ads if you get some traction. You don’t want that. If you want to get a business into the four figures, then the first question is do I think I can build something that people will want to pay for?

The second thing is there needs to be thousands of searches a month for something in order for me to even consider. If there are several hundred searches, odds are good you’re just not get enough of that traffic to make any kind of dent.

I think those are the big two things. I think the third thing could be—depends on your personality—but are you interested in building this? For me personally, I built and acquired a lot of businesses early on that I wasn’t particularly interested in but my goal was to provide value to people in exchange for money and then take that money so I could quit consulting and quit my salary job. So my goal, that was like the number one, and if that’s your goal, then I would say you don’t need to be interested in everything you’re building. It doesn’t have to be fun, sexy. But if you’re more the personality type where you really just can’t get into something unless you enjoy working on the product itself, then that could be a third criteria.

Louis: Let’s say from a few tools you mentioned, and as we say you can Google all of those terms to have tools, to understand how many people are looking for something online. Those tools will change and evolve overtime, but regardless you will be able to find those numbers. Let’s say we know that more than a thousand people every month are looking for WordPress plugin to convert Google Doc into WordPress post.

Rob: For WordPress, since its a freemium model—because you’re going to give something away up front and then only a small portion of those who are ever going to pay you—I would actually up that number. Let’s say you get 5000 searches a month so then you’ll probably get—I don’t know—a thousand downloads maybe? I’m kind of making up numbers but this is how I would think about it. You are only getting to the portion of those, and of those thousand, how many are going to upgrade and pay you? Maybe it’s 10 people? I’d say that’s 1% conversion rate. That’s not unreasonable.

So then can I charge for this addon that I’m going to build? Some add-ons are really cheap, $10–$30. Other add-ons are $99 or $199. I have to think through what am I actually going to build. Probably start small with something for $20. 10 sales, $20, 200 a month, back-on-the-napkin math, is that reasonable? I don’t know. What are my goals? That’s where it would start. Try to hash out those numbers like that.

Louis: That’s a very interesting way to think about it. Based on your experience, you have a feeling now like you have to feel for it. This isn’t the type of thing that can be taught that much. You probably made a ton of mistakes in the past by picking the wrong product or picking a product that you thought would be successful and that wasn’t, right?

Rob: Absolutely. You’ve said $1000 isn’t much to buy things with but I purchased a couple of different ebooks. One was about bonsai trees and then there was some plans on making a duck-hunting boat out of materials from Home Depot. I know it sounds crazy but the duck boat one, I try to think how much I paid for that. I think it’s less than $1000. I just knew how to SEO it and it was making me maybe $100 and I paid $1000 for it -ish, maybe $1500, and then I got it up to about $500 a month, based on just kind of improving the rankings. It meant people loved it, like I had all these testimonials. Again I wasn’t tricking anybody. It was thing thing that people really wanted. People sending me pictures of them building the boat. It wasn’t any interest I had, the plans were legit.

So, that’s another avenue you could go down. $1000 is pretty limited these days but that’s something that I did in my early days of kind of stair stepping my way up.

Louis: I would say for a lot of people, $200, $300, $400 a month is already enough to start with until you’re confident, as you said, right?

Rob: Yeah. It’s pretty interesting.

Louis: It’s good that you’re doing the math there and not using this napkin kind of methodology because it doesn’t have to be scientific and it can be scientific. At the end of the day, you will have to try to take a stab at it and see how its works. If you won’t, you’re not going to learn.

We keep with this WordPress plugin idea and we find out that—just for the sake of the argument—there are around 10,000 searches a month on this keyword. We know now that there is volume to sustain the objective that we have, maybe $500 a month, $600 a month. So we know it is possible.

The other thing I think that you want to look at because you only know now that people are looking for that but you don’t really know the landscape, you don’t really know whether existing products are solving this pain very well. Would you focus on landscape that has a lot of products but you all feel that are not good enough, what’s your approach on this side of things?

Rob: Later on if you’re going to build a company like a SaaS app, like how I built Drip, then you do want there to be some competition because it validates the market. But when you’re going on this microscale, it’s your very first time, and you’re literally going for hundreds of dollars a month as the goal, I would go with the goal that I’m going to rank number one, and that’s going to be good enough. I know I’m going to build the best product and I’m going to rank number one.

I don’t care if there are five other things that do similar things. As long as I think I can outrank them, that’s the challenge. If those are entrenched, like if I were to go and look and there was a WordPress plugin with 20,000–30,000 downloads, and it has a bunch of five-star ratings, I would probably say, “Oh, I’m not going to outrank them. I’m going to get a dramatically smaller amount of traffic so this is probably not an idea that I want to pursue.”

Louis: Okay. You want to look for leaders. Like those in the WordPress world, I’m thinking of Yoast SEO. This plugin is a clear leader in the SEO optimization like the SEO WordPress. I don’t know how many thousands of stars reviews are getting and the product is really, really good. So you probably don’t want to go there. But then–

Rob: It’d be tough.

Louis: Really, really tough. But maybe you can dive in into a very specific niche that still gets some searches, where you can really build something that you feel would be better than anything else that you tried.

Rob: That’s right. The further your niche down, obviously the smaller opportunity. But that doesn’t matter at this point because you’re not doing this to retire. You’re doing it for the experience, a little bit of money, the confidence, the skills of learning how to copywrite, how to build your landing page better than anyone else is doing, your landing page in wordpress.org. There’s so many skills that you’re going to take away from this, that are going to apply to everything else down the line. The whole point is to get something to launch it and to try to make your first dollar in a sustainable and an interesting way.

Louis: You sold—I don’t know—maybe millions worth of dollars of products in your experience building stuff and launching stuff. But do you think that the first dollar you have ever made was the best or do you still think that nowadays it’s simply good to sell stuff?

Rob: It’s still pretty good to sell stuff. I was very excited with the first dollar. It was a life-changing moment but as the dollars got bigger, it did get more interesting to me, I will admit.

Louis: This is something interesting because a lot of entrepreneurs will talk about the passion, like you need passion to do certain things. But, as you seem to mention, and I think I’m getting to that, you are passionate about adding value to people’s life and making money out of it.

Rob: That’s right.

Louis: Therefore you don’t care if it’s a bonsai tree ebook or an email automation software in a sense, as long as you feel you’re contributing to people’s lives, you’re adding value, and obviously you’re making money out of it.

Rob: That’s true, and especially early on I didn’t feel like I had the luxury to be too picky, because I wanted to get there fast. I didn’t want to consult and work for other people for another 5 or 10 years. I was trying to think what’s the quickest way that I can make a full-time living from products in an ethical and—like I said—value-driven way. And to me, it was to not be picky about the ideas.

Later on, I was pickier because I had the luxury. I was my own boss and I could do what I wanted. Then I was like, “All right. Now I’m going to work on stuff that I think is really going to interest me.” The latter two, HitTail—which was an SEO keyword tool; it’s a SaaS app—and then Drip, and MicroConf—as you mentioned—all that stuff is really interesting to me. Those topics are but I didn’t start with them and I wouldn’t give myself the luxury to do it in my first couple of years of entrepreneurship.

Louis: Let’s go back to what we mentioned already because I think it’s pretty valuable. You first had the mindset to focus on places where people are already hanging out. I love this idea because we’re not talking about online only. It’s very possible that you cannot run a small shop selling—I don’t know—sandwiches in a place in your city that has a lot of foot traffic, like a lot of people hanging out there. If you get the authorization from the city, you could make a profit quite fast, knowing that a lot of people hang out in this area.

Rob: That’s right. Exactly.

Louis: So, each work, it works for everything but I love your products. I’m not saying you’re guaranteed to make money or to succeed with it, but at least, you’re giving yourself much better chance because you’re using existing places where people hang out. Then you look at the amount of time, the amount of people searching for something specific, such as WordPress plugin to turn a Google Doc into a WordPress post. And then you try to understand using a kind of a very quick napkin calculation, whether this volume will bring enough money for you to reach your objective.

Once you do that you look at the competitive landscape a little bit and try to understand whether your product is niche enough, whether there’s too much competition, or whether you can safely build something that is better than the rest. Or, you can identify a product that is already there that you could potentially maintain that hasn’t been maintained in a while. There are many other areas there that enable you as a marketer who doesn’t have technical skills, to use something that already exists and make it better.

Rob: True. That’s right.

Louis: I think I’ve summarized the first part and I was planning to ask you now how did you get your first customers. But this approach that you mentioned is basically already answering this, if you are using places where people hang out.

Rob: Yeah, it’s baked-in. That’s right.

Louis: It’s baked-in, yeah. Let’s say we launched this first plugin and we learn from customers, we learn about copywriting. We get feedback, we improve the stuff as we go, and then we kind of reach the amount of searches or the amount of customers that we could get from it because you can’t really scale that, not a lot of people are looking for this particular term, so at the end of the day if you get $500 a month, out of it that might be the maximum you can ever get.

Rob: Right.

Louis: What do you do next then?

Rob: You have a couple options. One, you’re getting the $500 a month out of the paid addon that you built. If you think there are other paid add-ons to that free plugin, then you launch more paid add-ons, so you can just expand the base on that same customer base.

If that is not an option, then I would go back to step one and I’d repeat all of the steps. You’re going to have some money at your back so you can move faster. You have some experience doing it, so you’re not going to make the same mistakes.

Then, assuming that you can repeat this and get another WordPress plugin—two or three of them—you can bring income diversification in case any of them explodes for whatever reason. You never know if WordPress is going to accidentally ban your plugin and whatever. You basically get diversification and experience in doing it multiple times.

Louis: That makes total sense and I really like the first thing that you just mentioned about diversification, but also the aspect of thinking that you will have an audience there in front of you. You will start to have paying customers. If you do your research right, you will understand who they are, what are they looking for and naturally, almost most of the time what happens is that you start to discover other problems that you might be able to solve for them.

Rob: Yup. That’s a really good way to think about it. I agree because you have so much more data now than you did six months ago when you started.

Louis: That reminds me of a previous guest, Justin Jackson that you definitely know, who’s a solopreneur, who teaches solopreneurs and potential solopreneurs to launch a business and stuff. This is exactly what he done. He started with an ebook, he moved on to a course, he moved on something else, and all from the same audience. This is definitely doable. This is probably one of the most fulfilling way to do business. You have your audience, you grow it slowly, you help them more and more with more and more solutions to their problems, and you make a living out of it.

Rob: Yup. I’ve seen this repeated over and over, it’s something I stumbled onto myself starting in 2005—that was 12 years ago—and it’s something, like you said, Justin Jackson, Patrick McKenzie did this. The list is honestly approaching endless in terms of people who have done it. Whether it’s helping entrepreneurs or whether it’s helping a certain vertical of small businesses, there’s a lot of opportunities to it. It’s relatively repeatable, has a relatively high rate of success. It’s all the things I like to see in an approach.

Louis: Thank you for doing this exercise with me. I know it’s not easy and to have that many constraints but you are used to it so I knew you could answer that pretty easily.

Let’s talk about you for a while. I don’t know you personally. It’s the first time we’re talking together but you seem to be a very patient person. You seem to really be able to say, “I’m here for the long run, I’m waiting to make small investments now, work hard now, and then be patient about the potential opportunities I’m going to have.” You’re talking about the fact that you launched 12 years ago, you started that 12 years ago. How many products have you sold, do you think? How many type of different products have you sold in your lifetime so far, do you think?

Rob: I launched several websites that didn’t go anywhere in between 2000 and 2005, and just shut those down. Really, maybe I had one product before DotNetInvoice and then, if I were to do a loose count, Drip and HitTail. There’s probably MicroConf, doing a conference, is that a product? I’ve written a couple of different books, so it’s dozens, I would say? Yeah, it’s a lot.

Louis: It is a lot.

Rob: Fifteen, twenty. Yeah, in that range.

Louis: You are a patient person. I know you are. In this world where it seems like things are accelerating—social media everywhere, information overload—more and more marketers, in particular, seem to be absolutely overwhelmed with general of information targeting day-to-day. They don’t know where to start and they want these quick wins and these quick bucks, and they want those growth hacks and all of that.

Why do you think you have this mindset of being very patient and where do you think it’s coming from?

Rob: I say a couple of things. I may appear patient, but I tend to be pretty impatient in terms of, I just want things to move faster. Like when launching Drip, we were six months in and I was thinking why aren’t we at the product market fit yet? Why can’t we get there faster? I had a lot of anxiety about it. But with that in mind, I think what you’re calling patience that you see in me it’s more of like this long-term mindset. I know there’s this community that is formed around bootstrapping and around longevity. We’re going to be here in a decade, we’re going to be here in two decades still talking about this.

I guess to me you need to play long ball and you need to think what relationships do you want to build today. What relationships did you not want to sacrifice? Because I do see people with their short-term mindset. They burn their reputation too quickly because they do some growth hack or they piss someone off. Or they build a copycat product, thinking that this world is so big that no one will ever notice that it was me and then their name gets associated with something that people don’t like.

I think that’s it. I’ve just always thought long-term about everything. I think 5–10 years down the line, like what do I want to be doing then. Do I still want to be running this company? Do I still want to be selling this thing? Maybe that gives me a little more patience than others.

When I was starting out, there wasn’t this fervor like you’re talking about, the pace of all this advice, the tweets, the growth hacks, and all that stuff. It was more scrappy, you have to do it yourself, you read a couple of marketing books, and try to apply it to online marketing. As I was coming up, there wasn’t the amount of information coming like there is today.

Louis: Is there any particular event in your life that made you who you are today, that made you think long-term, having this long-term mindset?

Rob: When I was young, my parents worked with me. We just set a lot of mutual goals and I was always thinking during track—because I ran track for nine years—we’d always think where do I want my time to be next month. Then by the end of the season—when I was in school—what are my goals for the year. I was very goal-oriented.

I’m also a left-brained thinker as a software developer. I always think if I start writing this code today and I’m going to build this app, what decisions am I going to make today that are going to negatively impact me in six months when I’m still maintaining the same codebase. It’s realizing that the choices that you make today and the things you put into the world, they’re going to stick with you.

That was it. I just kind of grew up thinking that way. I don’t know if it’s a natural thing or if it’s kind of more of my environment. Like I said, my parents teach me to be more goal-oriented. Or, because I was a software developer. I started writing code when I was eight. There was an Apple IIe in our house and I picked up a book and started typing in the programs. That, I think, probably encouraged that as well.

Louis: Tell me more about this. You and your parents were setting goals together. Is that right?

Rob: Yeah.

Louis: Tell me more about how did that happen. Was it only for the track that you’re running or was it also for life in general?

Rob: Life for me at that time was sports and school. I got straight As for most of junior high and when I started the first quarter of high school, I got straight As. My dad said, “Hey you think you can you get straight As all through high school?” I thought, “I don’t know,” but that would be an interesting thing to shoot for. It was totally on whim. It wasn’t that it came necessarily easy to me, but suddenly it become like, “Hah! I think I want to do that.”

That’s what I did and I think I actually got, if I recall, I got two Bs the last semester when everything else was an A. It was crazy but by that time it didn’t devastate me because I remember just thinking I worked as hard as I could and I had a lot of the fun the last year. I don’t know. It wasn’t as bad as it sounds.

But then playing sports, playing football, and running track, it was all about how do I justify getting up early, going to practice, weightlifting, and all this really hard work when you’re 14, 15, 16 years old. How do I justify that? They way I justified it to myself was this is for an end goal. The hard work will lead me to win the state championship, or to have a successful season as a wide receiver. I think that’s kind of where I came from.

Louis: You seem to be a very mature styled student. I think a lot of parents listening to this podcast might think, “I really wished I had a kid like this.”

Rob: I think my parents groomed me to that. They shepherded that in me. They encourage that. The fact that my parents were perching me when I was so young, talking about goals, how many parents are that involved with their kids? Unfortunately, probably not enough.

Louis: Yes, and there’s a difference between being involved in your kid’s life by training them to work today. Come on you haven’t done your homework. Actually thinking long term, which is I think one of the reason why you have such a long-term mindset embedded in you because your parents were setting goals for you, teaching you the importance of setting long-term objectives and the daily work to reach them.

I’m not a teacher, I’m not a psychologist of any kind or anything like this, but it sounds to me like if you’re teaching your kids or colleagues or teammates to think long-term and to work day-to-day to achieve those goals, you might have better success than just thinking day-to-day.

Rob: Yeah, I would agree. We do that a lot here at Drip, still thinking long term. What’s interesting is I don’t know how much I do that with my own kids, so this is something I’m now thinking about, based on how we’ve talked about it. I don’t know that I realize the impact of that on me.

Louis: Alright there you go. Now you have a takeaway from this episode. How many kids you have?

Rob: I have three kids.

Louis: Let’s go back to marketing for a bit because my listeners might want to learn more from specific questions I intend to ask my guest and I’m really looking forward to your answers to those ones. But first, what do you think marketers can learn from developers?

Rob: I think developers tend to… it’s systems thinking? It’s thinking in terms of how can I be almost analytical. It’s left-brain thinking. Some marketers are like that already but a lot that I come across don’t measure their conversions, they don’t try to link the dollars they’re spending on their ads to how many people are buying in an exact, really scientific way. I feel developers tend to market in that way. I think creative problem-solving some marketers are really good at that but I do think that developers have to be somewhat creative to build software. I shouldn’t say have to. I think you should be somewhat creative to build good software and I think solving problems with code is something that can translate to marketing.

Louis: Let me switch the question around now. What do you think developers can learn from marketers?

Rob: I think developers need to learn that the product is not everything and that the customers and the marketing itself—in this day and age—can be worth a lot more in the success of the product. I also think as a developer when you’re getting started launching products, learning how to position, creativity in copywriting, I think it’s probably where it all boils down to. It’s learning how to talk about the benefits rather than the features. As a developer, I always think features first and I have to actively ask myself, so what? The app can do this, this, that, and this. So what? Then that gets me to the benefits. I think marketers tend to think that way and developers tend to think in terms of features.

Louis: Yeah because developers actually build in the features so it’s easier for them to describe it, while marketers tend to think—most of them, anyway—tend to think about customers and how they can talk to their customers over there.

I mentioned growth hack a little bit and you mentioned it as well. Listeners will know that I’m not a big fan of the mindset, at least this mindset of growth at any cost, growing for the sake of growing, trying to hack your way into stuff that won’t work next week, as of my own view. But in general, marketers have a bad reputation. There was this survey done by HubSpot—I remember well—that said that only 3% of people trusted marketers and lawyers were trusted more than us marketers. Why do you think yourself—from your experience—why do you think marketers have such a bad reputation?

Rob: It’s tough to say. I guess it depends on what circles you run in. If you talk to a bunch of developers, then they will say marketers have a bad reputation. If you talk to a group of salespeople, they probably wouldn’t think that. And obviously if you talk to marketers, they would tend to not think that.

I think this recent push into growth at all cost with the growth hacks and people pushing the boundaries of, maybe ethics in order to grow, I think that, to your point, has given folks a bad name. I think people look at Uber or people hear the story of the early Airbnb growth hack with Craigslist—which was against the terms of service—and that just feels like, perhaps overstepping some bounds that we should hold ourselves to maybe a higher standard than that.

I think there’s examples, though, of marketing that is really well-done and does not feel sleazy or anything. If you look at Apple’s marketing, I’ve always kind of respected how they market. I think there’s an online clothing store called Shinesty and it’s just super funny. ThinkGeek? Same thing. There’s a marketer there but it doesn’t feel like they’re marketing to you. In that respect, I would say I think some marketers are doing a good job with it and I think others are, maybe pushing the boundary to far.

Louis: This is a point that Rand Fishkin made on this podcast. He said that good marketing goes unnoticed. When a company does good marketing, what happens is if you say, “Oh it’s a nice brand,” or “it’s a nice product,” but never we do praise the marketer behind the campaign because it just feels like they understand you, and therefore it doesn’t feel like marketing. Bad marketing is the one we notice quite a lot.

Rob: Yeah that’s definitely true.

Louis: I love this definition. I think you made the same point, which was great to hear. What do you think marketers, startup founders, even tech people in general, what do you think they should learn today that will help them in the next 10 years, 20 years, or even 50 years?

Rob: I see you’re asking for timeless ideas. I’ve learned a few things but one thing that I think I will always try to impart to people is to have an opinion, to stand for something, and to be real. I think about launching Drip—which is marketing automation software now but when we launched it was email marketing software—and I had this opinion that there were other products out there that were kind of ripping off their customers. They were charging them a lot more money than they should have and they had this $2000 upfront fee just to get started with the SaaS app. That felt kind of crappy to me and my customers were telling me the same thing, like if you can build a marketing automation software that is more fair or just a better value and it’s easier to use. So we stood for something.

I don’t know if you saw the Drip homepage before we got acquired about 18 months ago. Before that, the headline on it said, “Lightweight marketing automation that doesn’t suck.” Our whole thing was that we were the anti big corporate marketing automation enterprise software. We call the few out by name on the home page. We said, “Look, are you tired of these clunky tools? The ones that charge you the money? The Infusionsofts and Marketos and the Pardots and the HubSpots.”

Actually we didn’t call HubSpot out but anyway, I’m just replaying it back. We stood for something, but it was also authentic. I did it because I genuinely believed that. I never had drama. It wasn’t false controversy. It wasn’t anything other than I have never, personally, have never wanted to have a line of copy or headline on my website that I wouldn’t say to someone face-to-face in a cocktail party or at a conference. I think if you are putting stuff online that you wouldn’t feel comfortable saying to someone face-to-face, then you may be overstepping your own personal kind of ethical limits.

Louis: Yeah. That’s a fantastic point. I was nodding on my own like an idiot for the last 30 seconds but this podcast is easily the same and I do believe 100% in what I’m fighting against. This is why I feel that I’m having so much fun doing it even during my spare time because I genuinely believe in it. This is an advice I tend to tell people is, “You need to find your enemy. You need to really define your enemy because when things are bad, when things got tough, when you want to give up, fighting against this enemy—it does not have to be a person or a company or it can be a thing or reason or mindset—fighting against it is the only thing that will keep you going.” I very much agree with your vision and this fantastic tip for people to keep in mind for the next 10 years, 20 years, or even 50 years.

You mentioned a lot of interesting resources throughout this broadcast. You mentioned Drip, which is the marketing automation software that you started. You mentioned MicroConf, which is the conference for solopreneurs. It’s a fantastic conference that I must go to soon. You also mentioned Startups For the Rest of Us, which is your amazing podcast that has been running for eights years now or no?

Rob: Seven, maybe? Give or take. Yeah, it’s hard to remember.

Louis: It’s insane. Weekly episodes. You managed to to keep it up for seven years and it’s not going to end anytime, right?

Rob: I hope not, yeah. That’s that thing of long-term. We show up every week. The fact that there’s two of us makes it easier. There’s a time booked and we don’t sacrifice that.

Louis: It’s a big learning for people. Besides all those amazing resources that you actively contributed to, what are the the top three resources you will recommend listeners today?

Rob: I would recommend that you check out copyhackers.com. It’s Joanna Wiebe and she has spoken at several MicroConfs. Very, very knowledgeable, very good at copywriting, positioning, and marketing, and someone who I admire in terms of maintaining a high bar of a kind of a low level of sleaziness, no sleaziness, a high bar of really ethical marketing.

Another resource that I like there—although there are some things that come on there that are a little over-the-top for me—but it’ actually you mentioned Rand Fishkin earlier. I think he helped launch this. It’s inbound.org and it’s kind of an aggregator. It’s like a Reddit but it focuses on marketing.

Then the third one is an interesting one. This will be controversial. It’s a book called The Ultimate Sales Letter and it’s by Dan Kennedy. But here’s the thing. When I read it, I thought to myself, this is too far. He goes too far in terms of valuing money over personal boundaries or whatever. He talks about headlines and I would never write those. But he’s still a very smart guy and I think I learned a ton from him. That’s where I started drawing my own limits, like I wouldn’t do that, I wouldn’t choose to do that. I don’t like how he markets but I still took lessons away from him. 80% of what he says I think is really smart. So, those are my three.

Louis: I appreciate your honesty on this. I haven’t read it yet and I know a few people mentioned it to me and I want to read it. But yes, sometimes just copywriting books of those ultimate sales machine type of books could feel a bit uncomfortable, but as you said, you can always take away everything from them. You don’t have to do all of the stuff tell you to do, because at the end of the day, if you have your enemy, if you have your values, if you really know who you stand for and who you are, you’re not going to go there. You’re going to be yourself, learn from them, and ditch the rest.

So, Rob once again you’ve been an absolute pleasure to talk to. I’ve learned a lot from you today. Do you have anything else that you like to say to our listeners? Perhaps a way for them to contact you?

Rob: Sure. Folks can reach me on Twitter. I’m @robwalling.

Louis: Awesome. Well Rob, once again, thank you so much.

Rob: Absolutely. Thanks for having me.

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