In this episode of Startups For The Rest Of Us, Laura Roeder joins the podcast to answer a number of listener questions on topics including managing annual subscriptions, being a non-developer founder, and more.
Items mentioned in this episode:
Welcome to Startups for the Rest of Us, the podcast that helps developers, designers and entrepreneurs be awesome in building, launching, and growing software products. Whether you’ve built your fifth startup, or you’re thinking about your first. I’m Rob and today with Laura Roeder, we’re going to share our experiences to help you avoid the mistakes we’ve made.
Welcome back to the show. This is the show where we focus on indie-funded and self-funded startups, folks who want to do interesting things, are ambitious, and want to build themselves a better life, but also want to build companies that grow. Starting a company is hard. Having this community of people who are going through the same thing that you are, having that sense of belonging, knowing (a) that it’s possible but (b) that there’s a place where we can all hang out and just get each other, and where you don’t go in and explain what you do and everyone looks at you funny, there’s a tremendous amount of value to that. That was a big reason why we started this podcast almost 10 years ago, back in 2010.
Startups for the Rest of Us has many episode formats. Sometimes, I just have conversations with folks, do interviews. Now and again, we do founder hot seats. But one of my favorite episode formats is listener questions. We’ve answered a tremendous number of listener questions over the years. We’ve had a lot of episodes on this. It’s just the gift that keeps on giving, because it’s a time for listeners to participate, and to hear what other folks are going through, and to hear the thought process of a couple of founders typically who’ve been there and have done some things, and it’s not that we’ve been through everything that they asked about, but you can at least hear that thought process of how we would approach it. And over the years, we’ve always receive positive feedback about this episode format.
Before we dive in, I want to let you know that at MicroConf, we are making an announcement next week. It is by far the biggest announcement that we will have made since we launched the event nine years ago. It is coincidental that the 20th MicroConf is going to be on April 20th of 2020, so the 20th during the 20s or whatever, but that’s not the announcement. I’ve obviously already mentioned that MicroConf Growth and Starter are in Minneapolis in late April of 2020, but if you’re not on the MicroConf list, I encourage you to go to microconf.com, enter your email, and we’ll loop you in as soon as we have the info. It really is pretty spectacular and you probably know me well enough by now to know that I’m not trying to inflate the importance of it.
Today I answer questions with founder Laura Roeder. If you don’t remember Laura, I interviewed her in episode 451. She runs MeetEdgar which is a social media management SaaS app and in 451, we talked about stellar growth, platform risk, layoffs, and powering through roadblocks. It was a really, really good interview and Laura knows her stuff. I have a ton of respect for her. Honestly, I always love getting on the mic and just chatting with her. Super fun. I had a fun interview at 451 and I had a great time talking to her today and hearing her insights and her take on some of your questions. Without further ado, let’s dive in.
Laura Roeder, thank you so much for coming back on the show.
Laura: I love the Startups for the Rest of Us. I cannot stay away.
Rob: Awesome. I am so stoked to have you on to answer some questions. You’ve actually submitted questions in the past, so it’s cool to have you on the other side of the ear bud, so to speak. We have some good questions today. As always, voicemails go to the top of the stack. I curated some questions that I think you should have some unique insight on. Let’s just roll right into the first voicemail which is about being a nontechnical founder and how to make good technical decisions.
Mack: Hi Rob, this is Mack from the UK. I’ve got a question, I’m looking for advice for a nontechnical founder. How can I avoid getting called out by poor decisions from the technical team or just not knowing about the consequences of some of the technical revisions that gets made to create their software? Any advice would be great. Thanks.
Rob: This is an interesting question, Laura. As a nontechnical SaaS founder yourself, I’m curious what your initial take is on it.
Laura: I would first like to take umbrage with the phrase non technical founder. I mean obviously, I know what he’s referring to. Nontechnical founder means that you are not a developer and I’m not a developer. But I always think it’s a little funny because I’m like, “I run a software company.” It doesn’t seem quite right to call me nontechnical, but this is a very real problem for all of us who are running software companies and are not developers because obviously, you are not intimately familiar with a really core part of what your company does.
I guess the first blanket advice for this is that, you really need to have a person in that CTO role who you trust 100%. I think this goes for any leadership role in your business, but it’s especially important in this case, because you’re not going to be able to provide so much oversight. Anyone can look at a customer service email and say, “Okay, that was not how we want to answer,” but you really can’t read code if you’re not a coder. I think that’s just step one is, make sure that you’re willing to put 100% faith in the person in that dev leadership role.
Rob: That’s what I was going to say as well. Even if you aren’t at the place where you can have a CTO. The fact that he used the phrase, “How do I not get called out,” does your team not trust you or do you feel like you have to make decisions that are out of your league? That’s an interesting turn of phrase. It implies that the team calls him out for making technical decisions, but are you making decisions you shouldn’t be since you’re not a developer? I would dig into that. I think having a CTO, or the senior dev, or somebody that really is making decisions in the best interest of the company, is a huge deal.
Laura: I think it also brings up that you shouldn’t try to pretend to be anything you’re not. If people are calling you out, does it mean that you’re pretending you know things that you don’t know or maybe making decisions that would be better for other people in the company to make? I think it’s just important to be unafraid to ask really stupid, really basic questions until you understand some of these core concepts related to writing code.
You can decide how much you feel you need to know. For me, I feel like I’ve been through this process recently big time with our finance team, understanding all the financials of the business. I just asked our finance person over and over and over again. Sometimes I’ll literally read a book. I read a finance book recently. I just wrote down questions for her in the margins and then I’m like, “I want you to read this book too and we’re going to have a call together. I’m going to ask you all of my questions about the book.”
I think that’s a great thing to do for technical questions as well. You need to be open with your team about what you know and don’t know and I think it’s important for you to work with the type of person that is very patient and very understanding in explaining things to you. Within reason, you don’t need to understand every detail. There are a lot of concepts that are probably unfamiliar to you that you do need to understand at least the basics of how “the sausage gets made.”
Rob: I like your example because as a founder, you don’t need to know every single thing about bookkeeping, accounting, and finance, but you should probably know enough to be able to ask the right questions. I feel the same way running a software company. I don’t think you should be able to code everything in a SaaS app, but maybe it’s worth going through a code where the code camps or maybe it’s worth on the side taking you to make classes.
It’s easier than ever to learn and have just a really basic level of coding knowledge such that, yes, you’ll never be able to make architectural decisions, you won’t make the senior level things, but you can at least relate to, “Oh, this is what code is. This is how it works. This is what it’s like to write a bug,” and spend four hours and not realizing that it’s the semicolon. That’s a lot of what it is. I think having that cursory knowledge and being able to then ask the right questions is what you’re touching on and that’s what I like about it.
Rob: You don’t like the term non technical founder. If you’re a developer and you’re writing the code, then you’re like a developer founder, is it a non-developer founder, is there a term that you prefer rather than nontechnical?
Laura: I guess maybe just say founder and then when you’re explaining later your side of the business, because you also don’t call like you just a developer founder, but I’ve never heard anyone actually say that.
Rob: I was just making up a new term to try not to say technical and non, because typically it’s technical and nontechnical are the two terms people use. I was just trying to think of a different way to say that because you’re right, running a SaaS app, yes, you may not write code but you are more technical than most people we know just because by nature of being in it. It is a misnomer.
But if someone wanted to differentiate between Derek and I when we started Drip, he was literally in a code every day and I was literally not in the code every day. I don’t know how else you differentiate that or what phrase we could come up. I don’t feel nontechnical founder as pejorative. I don’t feel like it’s a negative. Does it have a stigma? Do you feel like it does?
Laura: I actually think it does have a little bit of a stigma because I’ve heard developers use it in that way before. We’re not as cool of a founder if you’re not technical.
Rob: No, I think that’s lame.
Laura: That is lame.
Rob: That sucks. I don’t use it that way but if it gets that connotation then yeah, we need to figure out another phrase for it. Cool. Thanks for the question. I hope that was helpful.
We’re going to bounce into our second question which is also a voicemail. It’s about a founder who’s launching a second SaaS app. They’re nearing launch and he’s concerned about potential lawsuits.
Thomas: Hello, this is Thomas from Austria. I listened to the show for a long time and wanted to tell you that it’s really great content. I love following along your journeys and also hear stories of other people in similar situations.
To my question, I founded a SaaS company three years ago. It provides an invoicing solution for small independent car repair shops. It’s doing pretty okay. I can live off it and it’s slowly growing, so I’m happy with that. Half a year ago, I founded another company with a partner and we are building a software to compare prices for car parts.
Now that we want to go to market with the software to the suppliers, the […] of us are trying to fight us pretty hard. I think we have to go to court several times. There is not really a legal problem with fetching the prices because we do it locally on the customer’s computer and they’re not going through our systems, but still they can make our lives very miserable if they pulled us to court all the time.
Now, I’m not really sure how to go along. My partner really wants to push through that and he’s sure that it will work out. I’m also pretty sure that it will work out in the end, but I’m not sure if I am the right person to spend my next one, two, three years fighting big companies. I wanted to hear your thoughts on that and maybe what you would do in this situation. Thank you.
Rob: Thomas also wrote in and he said that he wanted to clarify that he hasn’t spent any money on the price comparison project, and have a small private investor, but in essence, he has only invested his time so far. I should preface this with we’re not legal experts, we don’t give legal advice, obviously, but it’s more of, “Hey, if I were in your shoes, how would I think through this?” This is an interesting situation. I’m not sure it’s one I’ve heard before. What do you think about this Laura?
Laura: The way I think of it is just, there are pros and cons with every business, every business model, and it’s really smart to go into a business with your eyes wide open about those pros and cons. From what I understood from his message, this is a likely threat, not a certain threat. He suspects that there is going to be lawsuits. He has a good reason to believe that’s going to happen or it could not happen at all. It makes me think of with my business MeetEdgar, we are entirely dependent on the social networks. You can listen to my interview on this podcast on Startups for the Rest of Us. I talked about a big problem we had because of that, but all businesses have upsides and downsides.
For me, I know that I’m in a space where I’m totally dependent on these partners that I have no relationship with and that can do whatever they want. That’s a big downside to my business. The big upside is that I’m building on Facebook, Twitter, and Instagram. Obviously, very popular tools, so lots of users. I think that he just needs to know this going in and maybe it’s something that you budget for.
It’s good not to be scared of it. It’s good to go in and say, “Okay, I know that this will likely happen. Maybe we have some money set aside for it. Maybe we’ve already figured out who our lawyer is so they can jump right in and we won’t be surprised,” spending a few months just trying to find a good counsel.
To me it doesn’t sound like a deal breaker, because it might not even happen at all. Like you said, you have to know that that is a battle that you could be fighting and you have to know that that’s something that you want to sign up for.
Rob: I like the way you’re thinking about it. I think these unknowns, like if you’ve never received a cease and desist, or you’ve never been sued, it’s super scary. You don’t you don’t know what that entails. I got sued by a patent troll about probably five years ago, but it was literally a blanket. It was about a troll. Someone who sued 100 people at once for having online invoicing software is what it was. It was just this crazy, he sued everybody that does online invoicing because it was a ridiculous patent. I got to be honest, I was super scared the day I got the email.
Then I quickly realized I could talk to a lawyer and someone was just like, “Yeah, this just isn’t that big of a deal,” and we have these stigmas against things. Lawsuits can be a big deal. They can be expensive, but your point of it’s almost like try to demystify, or de-risk, or just get more familiar with what this might look like. Typically, if you were to launch something like this, you’re not going to get five lawsuits the next day from five suppliers. It’s probably going to be weeks, months, and then they’re going to grumble and they’re going to have to call you or send you an email, and then you might get a cease and desist.
It would be a long process and maybe like you said, you set aside money to either have a lawyer, whether it’s to go to court or whether it’s to try to negotiate settlements. There’s a lot of options here and I think this comes back to expertise. As a nonlawyer, you should know how to ask the right questions, but you’re not the expert in how they should all go down. There’s folks who can give you advice if you find a good counsel.
I think the biggest question for me is, is this a big idea? Is this a seven-figure idea or an eight-figure idea that’s worth going through all of this for it or is it something that’s going to generate $5000 a month? In which case personally, it doesn’t sound like it would really be worth it. I mean maybe I would launch it and if it’s doing a couple thousand dollars a month or $5000 a month and you start getting cease and desist, well maybe that’s the point where you’re like, “Okay, I guess I’m going to pull the plug on this,” maybe that’s the best decision because it just doesn’t make enough money or maybe that is your defense of, it doesn’t make enough money. Go ahead and sue it. It’s not worth anything.
I think that’s really the question I’d be asking, not is it worth it, but is the idea big enough? Do you think the company can be big enough to make it worth fighting for?
Laura: I think it’s also worth a quick Google. I think he said he’s in Austria. He didn’t say if the business would also be dealing with Austrian suppliers. America is very litigious, most of Europe is not, you can’t just file random lawsuits about anything the way you can in America. If this were my business, you can figure out a pretty good amount just from educating yourself on the internet. Would the suppliers have any case? If they wouldn’t, that’s also just going to make the whole thing much more unlikely.
Rob: Yeah. Thanks for the question Thomas. I hope that was helpful. Depending on what happens, I’d love to hear an update on how you move forward.
Our next question is about pricing and whether to try to go for more customers with lower pricing or vice-versa. It’s from Winslow Moore and he says, “I’m a huge fan of your podcast and all you guys do. I found you guys at the end of last year when I was going through a bit of what I’m doing in my life and I’ve learned so much. I’ve wanted to reach out for a while, but haven’t because my current product under development isn’t SaaS, it’s just an app. A recipe book app to be precise.” I’m assuming it’s a mobile app.
“Development is nearing completion and I’m wanting to make a landing page to gain some interest. Before I do, I’d like to figure out some pricing scheme options and I’m hoping you can give some advice. Here are my main ideas. Number one, make the app free with ads,” he listed pros and cons, “Number two, make the app freemium with paying to unlock X recipe storage. The third is to make it cheap like $1, and the fourth is to make it a subscription like $1 a month or $5 a quarter. Again, I know this isn’t something you normally answer questions on, but if you feel adventurous, it would be appreciated.” What do you think?
Laura: I feel like I have some news that he’s not going to like to hear. I’m trying to let him down gently. This is one of the most crowded spaces you could possibly enter. There’s so much recipe content on the internet. So much of it is excellent and so much of it is free. None of the models that you outlined gave a compelling reason for someone to pay. You just said like a recipe app, maybe they’ll pay $1, maybe they’ll pay a subscription. I think you just need to rethink your starting assumptions or maybe there’s something you didn’t tell us, because there are reasons that people could pay for some recipe or cooking service.
I know a SaaS business that does meal plans for people. You put in all of your detailed dietary requirements and they spit out really specific meal plans, shopping lists, and there’s a whole app and a subscription around it. They have a business doing that because they’re meeting a specific need in the market that is related to recipes. There are businesses related to recipes and food, but just recipe app, I don’t think is really one of them.
Rob: I like the way you’re thinking about it because if you were to niche way down and, like you said, build custom meal plans, that’s something you can’t get for free, or it’s really hard to do at a good quality or vegan meal plans or Paleo meal plans. There are ways to think about it. I’m guessing everything I just named is already done to death. Even if he has, let’s say, he builds not just content and he builds an app that actually has functionality that people are interested in. A $1 a month, you need a thousand customers to make, and doesn’t Apple 30%, I think, so you’re really making $0.70 on that. You need a thousand customers to make $700 a month. That is a tough business.
Even with apps store distribution, you would really need to know apps store SEO. I mean you to rank in the top whatever, top five, four or whatever term that has enough volume to do it. This would be a pure search play in my opinion, because at $1 a month, even for lifetime value is $10, $20, $30, $40, you can’t run ads, you can’t hire sales, none of the standard models work. It’s purely a spray-and-pray and it’s, “I need to have enough free traffic,” so you need virality, or you need organic discovery through a search engine. Really, none of these pricing models are easy.
Laura: I’m going to go out and say they’re not viable. I think it’s polite to say that they’re not easy, but they’re really only viable if you have some way of getting that mass, which is possible. Maybe you’re like, “I’m going to raise a ton of funding and I’m going to be the number one recipe destination on the internet.” Someone has to be that. That’s not an impossible thing, but it’s going to take a ton of money to get there or you’re like. “I am the number one SEO ninja on the app store. No one can do apps store SEO better than me and I also probably have a bunch of money or some money to put behind it, so that’s how I’m going to get there.”
I just think you need to really look at how does mass work out to make this a viable business and what’s my strategy beyond just like, “Well, I hope a lot of people find my recipe app in the app store.”
Rob: And even if you’re building a SaaS app, let’s say, just in general, what’s the general rule? The lower your price point, the higher your churn, the harder it is to grow. This is not in every case, but it’s in 95% of cases. That’s why so many SaaS apps, the playbook is, you go out, you underprice yourself because you just don’t know any better or you don’t value what your built and over time everybody goes up market. It’s a very common playbook.
The reason is if those customers as you go up market tend to churn less, they tend to be more sophisticated, less support, there’s just a bunch of plusses with it, but you often can’t start out at those high price points because your product is not worth it at that point. It doesn’t provide the value and it takes you time to get product market fit with that audience. Then move it up market.
Laura: That’s all B2B stuff, also, everything you’re saying. We’re talking B2C, so I don’t think there’s really even a big market to go to for an app. There’s more expensive consumer services but, I’ve never heard of an expensive app. Maybe it’s a thing, people have done everything. Now I’m curious. Is there an app for consumers that cost $800 a month and is a lot more high-end looking than the other app? I don’t know.
Rob: I’ve never heard of one. I bought a $25 app the other day. It wasn’t a subscription, but it’s a teleprompter, that goes on my iPhone, that listens to my voice. It’s the only one that turns the microphone on and as I speak, it teleprompts automatically. To me that was worth $25, but really, am I a consumer? Because I bought it for business purposes. I bought it for these videos I’m recording. I’ve also bought $20 app a couple of years ago. It was before where you can pair an iPad as a second monitor to your Mac. It was software that did that. Again, there was only one or two of them and I did the best one. It wasn’t a subscription and I would’ve been less likely to pay a subscription for either those to be honest.
Laura: Yeah, those are really tough models, too, where they’re only making $20 one time.
Rob: Right. Thanks for your question, Winston. Sorry for the bad news, but I hope that was helpful. I’m curious, if you love recipes or somehow love that space, then dig in and figure out that maybe it’s not a $1 app, maybe it is a website that you acquire from someone to get a traffic source and you build just a web app into there. I mean, there are other options in the food and recipe space, that I’m sure there’s opportunity and I would say don’t get locked into trying to pick up pennies really is what $1 a month it’s like.
Laura: I didn’t actually say the name of the one I was talking about. It’s realplans.com if you want to check that out.
Rob: Awesome. Our next question is about recurring payments and it’s from Gavin Esplan. He says, “I’m in the planning stage of a small daycare management app. One of the main features will be setting up recurring payments between the daycare providers and their customers, who are parents or guardians of the kids. I also need recurring payments for the providers to pay me. I’m a professional web developer, but I’m not sure which system, like Stripe, would be best to accomplish this. I’m leaning toward Stripe, but it’s probably because it’s the one I’ve heard of most. I’m not sure what other good options would be out there. Do you guys have any recommendations?” What do you think, Laura?
Laura: Well, there’s an easy part and a hard part to his question. As far as him taking payments from customer, I say yeah, Stripe is great. We use it. We like it. Go for it. The other part where your customers take payments gets a lot trickier because your customers need to have something like Stripe or PayPal, but they need their own individual accounts and then are you helping then set that up? Then there’s your customer stuff that has to be complied with or do they already have their accounts? I just want to point out there’s a trickier question within the question.
Rob: Stripe Connect is for marketplaces. I think it’s for this instance. I’ve never used it, but I know folks who’ve set up market places and use it. This isn’t technically a market place, so that’s where I’m not sure if the terms of service would apply to him having 20 or 30 day cares using it and taking payments or if the Know Your Customer stuff would pass through to him. Do you have any interaction with Stripe Connect?
Laura: No, I’ve researched it a little bit for a different project and the hurdle that we came up with is that this similar model, they still have to have their own Stripe account which Stripe helps facilitate. We thought that might be confusing and challenging for this customer to set that up which I imagine daycare centers might have the same or they might have their own payment system already that they’re using.
Rob: Yes I would head to Stripe Connect and at least research it because that’s the one that I’ve heard the most about when you’re in this type of situation. Again, not saying it’s going to work but I think that’s where it starts. In my opinion, Stripe is number one in this game. They kill it. They make it easy and if you can make it work with them, great. To me, by my rules, if for some reason I couldn’t you Stripe, I would look at Braintree. I think they’re the number two in our space for doing this stuff.
Obviously, it doesn’t sound like he’s funded. I’m guessing he’s bootstrapped listening to this podcast. If you look at Gumroad, as an example, became a processor themselves. That is a possibility. There’s a lot of red tape and regulation. I’m guessing, one of the reasons I heard Gumroad raised their money was that they had to go to banks basically and have a bank say, “Okay, we’re cool with you being a processor.” If you’re some bootstrap person working at your garage, that’s unlikely to happen. It’s probably not an option for you now, but in the longer term hopefully, you don’t have to do that, but that would be a parachute option, I think. Thanks for the question, Gavin, hope that was helpful.
Our next question is from Ash Yadav, and he’s looking for thoughts on joining an early stage startup just after graduation. He said, “I just cover the podcast, I’m going through one episode at a time. They really informative and enjoyable. I recently graduated with a degree in EECS,” Electrical Engineering and Computer Science, I think, “then joined an early stage Internet of Things startup. I want to ask what are some tools, courses, workshops, et cetera, I can look into to get more comfortable with the industry lingo.
As I recently graduated, working in a two person team right now, there are times when I have to talk to clients or talk to people who are much more experienced than me and sometimes I feel left out. I don’t have industry project management experience, an MBA, or the entrepreneurial experience to be fluent in business lingo. For example, this might sound silly, but someone recently talked to me about beta sites and I had no clue what beta sites were. Luckily, I was able to figure it out while we chatted in made it out alive, but I fear I’ll be in a similar situation again.”
You almost certainly will. I remember my first job out of college and I didn’t understand anything. Thanks that’s a great question, Ash. Interested in your thoughts, Laura.
Laura: I think the first thing, Ash, is that someone asking questions is a huge sign of intelligence, not the opposite. Everyone knows that you’re young, everyone knows that you just graduated from college. When you ask those questions like, “What’s a beta site?” instead of pretending that you know and then maybe being way off base, it’s actually going to make you look much smarter, eager to learn, and capable than just pretending that you know stuff. Hopefully, most of the people around you feel the same way that I do. I don’t think you should be shy about asking questions. Even if it’s something that you feel is really basic, that you feel a bit embarrassed about.
We all we’re born knowing nothing. No one knew the term Internet of Things until the first time they heard it and then someone explain it to them. No one is born knowing any of those stuff. I think people should do this anytime in their career. We were talking about this earlier in the podcast about learning and asking questions, asking more questions. For me, the answer is less about courses and more of just having the attitude and the mindset that asking questions is a wonderful thing and that’s how you learn.
Rob: Yeah, when I graduate from college and had my first job, I thought I needed to know everything. I felt weird about asking questions and I thought it was a sign of weakness. I pretty quickly learned what fixed it for me is I worked with this one guy who is really smart and he was senior and he knew bunch stuff. In meetings, someone would say a concept and I remember being like, “Oh, I know what that is,” and he would say, “I don’t know what that is. Can you define out for the group?” and I was like, “Whoa.” Everybody respected him.
That showed me that it was okay to ask a question like that. It was such a good model for me and I think the thing to keep in mind is you’re going to ask a lot of questions up front, but it’s not going to be like that forever, because you’re just going to learn enough. First, you’re going to learn 20% and then 60% and then you’re going to get to the point where you’re 80 or 90% fluent in all the lingo. That may take three months, it may take six months, but at a certain point, you’re not going to ask as many questions.
You still want to ask questions, but you’re going to be seen as more of this mid-level or senior and you’ll get to the point where you don’t have to do it all the time. For me, if I was trying to learn about a new space, I don’t know much about IoT (Internet of Things), just what I’ve heard on Tech podcast, so if I got a job at one, I would probably be in a similar boat. I would dive deep in the IoT podcasts and some IoT audio books. For me, I do a lot of audio just because that’s my thing. For you, maybe it’s Kindle or maybe it’s paper or whatever I would use Google a lot. I will try to get the lingo from the podcast or the books in advance and then every time I heard something I didn’t understand I would Google it. You’ll be shocked, there’s only so many terms in any space.
In SaaS, it’s an app and there’s MRR and there’s LTV and it sounds like there is infinite, but if you listen to the show for probably 10 or 20 episodes, you’re going to hear 90% of the terms that we all use. If you’ve defined of those and committed them to memory, that’s great training for trying to get up to speed faster.
Laura: Yeah, I love that advice. I was thinking just the other day I actually Googled the term “test case.” It came up in my company flat, they’re talking about test cases and I was like, “You know, I’m assuming I know what that means, based on some context, but I’m actually not sure that I know what a test case is. I just Googled it and I read about it and I figured it out, right in front of a nontechnical founder thing.” This is a skill that you want to have throughout your career and like Rob said, luckily, it will get certainly easier and you’ll have to do less Googling as time goes on.
It’s something to embrace to make sure that you’re not making assumptions, make sure that you are on the same page which is why it can be good to ask things like, “Okay, this is this is what I mean when I say test case, is that what you mean,” because those types of miscommunications come up all the time.
Rob: That’s a really good point. Probably once a week, I Google an acronym. Oftentimes, it’s something someone posts on Twitter and it’s like a colloquialism that I just don’t know. I mean maybe a year ago it was TBH and I used TBH the other day. I was talking to my 13-year-old and in conversation out loud, I was like, “So TBH, blah, blah, blah.” He’s like, “What does that mean?” and I was like, “To be honest.” He’s like, “Oh my, you’re such a nerd.” But I find myself Googling this on what does this mean and then there’s like seven different definitions and you have to take it from context. Don’t feel like you’re in over your head, Ash. I think we all are. Just because someone has been doing this for a few years doesn’t mean that they know everything about it. Thanks for the question. I think it’s a good one.
Wrapping this up for the day, our final question is from Zee and it’s about managing subscriptions. He says, “Hello. Big fan. What recommendations do you have to manage subscriptions that come both via credit card and check? As the business is growing, I want to make sure I’m not missing out on things as people renew their subscriptions. For example, we make a credit card payments through Braintree.” I think it means they accept credit card payments through Braintree, but they also have people that pay via check annually and they handle stuff through PayPal.
To set the context, when I first read this, I thought he was saying, “We have a bunch of SaaS subscriptions, how do we keep track of those?” But he’s actually saying they accept payments in a bunch of different ways, some of which are annual. He says, “We then use QuickBooks for all the accounting. We want to be sure we don’t miss out on annual fees.” Laura, have you had to deal with this?
Laura: No, I haven’t.
Rob: Is it all credit card with EDGAR?
Laura: Yeah. I mean, we would just say, “No, thank you.” if someone wanted to buy with a check, but I know that in some industries, you can’t do that.
Rob: Yeah we did this with Drip. Let me think. After we get acquired by Leadpages, we were using Stripe, they were using Braintree. At a certain point, we started accepting PayPal and they were doing these larger annual contract values. You get you get a 12-month subscription that is $20,000 and really that’s an invoice check situation. Frankly, you don’t want to pay the $600 processing fee, the 3%, but also the companies, bigger companies as you said that’s the way it works
The way we did it, like the very first one, is it literally went into an Excel spreadsheet or maybe it was a Google Docs that we all had access to and we’re like, Okay, note to self, calendar reminder,” and it goes into a Google Doc. In the next month, we need to build some type of system. Then we just went into our existing billing code, and we tweak some things to say, “Oh, this is a check and so and so needs to be reminded.” It sends off an email to this AR (accounts receivable) at this certain thing. We hacked it together. That took one day or two days of development work, but in the moment we were able to accept the check.
We knew there was a calendar reminder in case everything went haywire. We went back and it was like this just in time MVP implementation of something. I’ve been gone from Drip for two years now. I’m guessing by now, hopefully they built even a better system. I think there are a bunch of ways to do this and that they’re trying to build a gold-plated version from V1 is not necessarily the best way to do it. If you only have one or two customers paying you that way, you just don’t need that much infrastructure.
Laura: Yeah, I don’t have anything on this one.
Rob: All right. Well Laura, thanks again for coming back on the show. It’s so good to chat with you. Folks who want to keep up with you, you are @lkr on Twitter, that’s a great three-letter Twitter handle, I’m so jealous. If folks want to know what you’re up to with Edgar, they can head to meetedgar.com. Anything else you’d like folks to check out?
Laura: I would just like to say that people used to be a lot more impressed by my Twitter handle, I feel like you can tell that Twitter’s on its way out because I used to get a much bigger reaction. You threw in a little comment which was very polite of you, but I missed out on having a cool Instagram handle. My Instagram is @laurakroeder, I can’t even get @lauraroeder, I had to throw my middle initial in there. I’m just like feeling a little old that I missed the Instagram thing and no one cares about my Twitter handle anymore. That’s my closing comment for the show.
Rob: That’s amazing. Thank you so much. I guess I should go register an Instagram handle, is what you’re saying. That’s how old I am.
Laura: Yeah. Get on that.
Rob: Thanks again, Laura. I hope you enjoyed today’s episode. Next week on the show, Mr. Brian Castle from Bootstrapped Web and Process Kit is coming on to talk about just the brutal year he had in 2016 and 2017, overcoming a 40% decline in MRR, and we walk through his trials and tribulations, dig into frankly some struggles, some victories and failures, and it’s a good interview. Also I hope you’ve been checking out TinySeed Tales on Thursday mornings. That season wraps up here in the next week or so.
I would love to hear your feedback or input on that. You can email me directly email@example.com, you can Twitter DM me, or if you have great things to say, obviously, just go into Twitter and let me know. I appreciate it. Should we do it again? I’ve started working on season two doing some interviews, but if you like it, if you will listen, if it’s a good fit for you, please let me know. If it’s not, that’s cool, too.
It was definitely an experiment. As I’ve said when we announced that this is by far the most time and money I’ve ever invested into an audio project. It’s TinySeed tales, because TinySeed was able to make that happen. If it’s worth it and it’s providing value, then we’ll keep doing it. If not, we always have more good ideas we can implement, so I can obviously but my focus elsewhere.
You heard a bunch of questions answered today. If you have a question for the show, you can leave us a voicemail at 888-801-9690 or you can record an MP3 and WAV, an Ogg Vorbis, an AIFF, send us a Dropbox or a GDrive link to firstname.lastname@example.org.
I tweeted something out a couple weeks ago and I said if I were starting a company today, these are the tools that I would use. I just listed it, it was a five-minute tweet tops. I just listed a bunch of things and look through them, made comments and spit it out. It’s like one of the most popular tweets I’ve ever done. These things are both fine and infuriating, where you spend 20 minutes trying to craft something and like six people care about it and then you do something like this that is just off-the-cuff-flippant and it gets all these traction. I think it has 150 retweets or something at this point.
The funny thing is just the opinions about Dropbox versus GDrive versus Box. It was like, “Why not that? “ It’s personal preference. There’s feature parity. These things are not so different from one another, it’s really a personal preference, unless there’s some individual, sneaky feature somewhere that somebody has that you really need. For the most part, these things are all equivalent, but I think a lot of preference comes into it as well as pricing and stuff.
Anyway, I digress. Our theme music on the show is an excerpt from a song called We’re Outta Control by a band named MoOt, it’s used under Creative Commons. You can subscribe to this podcast, and you should, by searching for startups in any pod catcher you have. To be honest, new subscribers is a big ranking factor in iTunes. If you’re listening to this and you’re not subscribed, even if you just listen to it on the web or you somehow download it through an FTP script that you coded up years ago, it would be super cool if you would open iTunes and just hit the subscribe button because it does help us rank higher. It helps us get more reach and it helps us reach more people.
If you haven’t been to startupsfortherestofus.com in a while, we have full transcripts of all of our episodes within a week or two after they air, we […] the audio live is that, number one thing in transcripts just take time to get done. We get a decent number of helpful comments on the site too, so if you have a comment on an episode, you can obviously tweet to me @robwalling or you can come to the website itself startupsfortherestofus.com. Check out the fancy new design we put in place a couple of months ago. Leave a comment, drop us an email through the contact form. Thank you so much for listening today. I’ll see you next time.
In this episode of Startups For The Rest Of Us, Rob interviews Craig Hewitt of Castos, about the unique set of challenges to starting and growing a SaaS product as a non-technical founder.
Items mentioned in this episode:
In this week’s episode, I speak with Craig Hewitt about how he went from his day job, to running a product-type service, to running a fast growing SaaS application called Castos; all this as a non-technical founder. This is Startups for the Rest of Us episode 459.
Welcome to Startups for the Rest of Us, the podcast that helps developers, designers, and entrepreneurs be awesome at building, launching, and growing startups. Whether you’ve built your fifth start up or you’re working on your first. I’m Rob and today with Craig Hewitt, we’re going to share our experiences to help you avoid the mistakes we’ve made on our journeys.
Thanks for joining me this week. I’m excited to talk to Craig Hewitt. You may know him from his podcast, RogueStartups, where he has chronicled his journey over the past several years. If I recall correctly, that’s where I first heard about Craig. What I like about Craig is he has been doing this for years, 4½ years ago, he started a productized consulting service.
Two years later, he quit his day job. He acquired a WordPress plugin, he started Castos, which SaaS app for podcasts hosting. He’s built it up to the point where he has four full time employees, two part time employees and he’s part of our inaugural TinySeed batch.
You’re going to enjoy the conversation with Craig. We dive into a lot of stuff that he hasn’t talked about on his podcast and per the interviews I’ve been doing recently, I try to dig into some points in particular and not just cover a broad story, but really look at the important points along his journey, things he learned, advice that you can take away to help you build and grow your startup as well.
I want to do a little experiment this week, it’s something I haven’t done before. I talked to Craig offline and said, “You know? I bet folks will listen to this episode and they might have questions for you.” Whether it’s a question about how you did it, about your journey, about podcasting, about startups in general, just anything that you would like to hear Craig and I riff on and talk about, or frankly if it’s just for Craig, that’s okay too. I want to invite him back in probably two, maybe three weeks, and any questions that have been submitted, he and I can run through on the show. It’s a Q&A episode, but it’s a Q&A episode with a guest host and you have context about his experience.
As you listen to this episode, please try to think of a question or two for Craig and then email it to email@example.com and you can send that as a text question or attach it, Dropbox link to an MP3, or you can just call our voicemail number if you’re on your phone right now. It’s (888) 801-9690 and I’d love to have Craig back on the show, assuming we get questions, and we can run through those.
It could be an interesting and fun experiment to have these guests to come on the show, not just tell their story but also offer practical advice and tips. This is something I’ve been talking about for quite some time about how I’ve enjoyed a Q&A episodes because it allows all of us to be smarter.
The fact that I’m here on the microphone, talking in answering questions is good and I’ve been able to share knowledge along with Mike Taber for the past nine plus years. The community and everyone out there, collectively, we are all smarter if more of us can weigh in on these topics. I love to pull guests back on the show and do questions, so please do send any in, firstname.lastname@example.org, if you have any questions for Craig. Maybe put “Question for Craig” in the subject line, that’ll help me catalog them. Let’s dive into the interview with Craig, I hope you enjoy it as much as I did.
Craig: thanks so much for joining me on the podcast today.
Craig: My pleasure. Thanks from me on, Rob.
Rob: I bet a lot of folks know who you are from your RogueStartups podcast. You’ve been known for several years—congrats on that, by the way—so many podcasts don’t even make it 20 or 30 episodes and you guys are at 170 something?
Craig: Yeah we’ll be at 200 around the end of the year.
Rob: Good for you. On these milestone episodes, everyone always tries to do something cool and interesting and I always find it hard to come up with new things. Have you been given thought to what you might do on that episode?
Craig: We have thought about it. We did a really cool episode at 100. It was a mash up of a bunch of little interviews that Dave did at MicroConf two years ago. We might do something similar to that, just talking about a little bit of everything, founder stories, lessons learned, stuff like that. I think those are really neat.
Rob: That’s cool. I was asking you because our 500th episode is coming up and I wanted to steal your idea and do it before you even do it. Of course I wouldn’t do that.
Craig: You’re welcome.
Rob: Yeah, exactly. The reason I wanted to have you on the show today well, there are many reasons, but one is you’re a non-technical founder who has built a successful SaaS app. Successful to the point that you have four full-time employees, two part-time, TinySeed, we backed you, you’re part of our inaugural TinySeed batch. Stuff’s really been going up into the right for you for a couple years now with Castos.
I wanted to walk through that story because starting a SaaS app is hard enough. Starting a SaaS app as a non developer, there are unique challenges with it. I want to take people back to where you started.
Now, you live in Annecy, France with your family, but you’re from the States. You were living in New Orleans, if I recall, and you were working a day job as a sales guy. Is that right?
Craig: Yes. I’m the dreaded sales guy at heart, which is actually a really nice thing. If you’re not a developer, you have to be a salesperson or a marketer. That’s what I bring to the table I guess, but yeah, I was in enterprise-level medical sales, so selling stuff the hospitals and doctors.
I started the podcast, started RougeStartups just really as a fan of entrepreneurship, software, SaaS, and stuff like that, online business. Ironically, that’s what led to my first business that was any kind of success. It’s called PodcastMotor, we do podcast editing and production, we’re a productized service. That’s what led me to quit my day job. We traveled the world for a little bit and ended up living in France. Then all the opportunities with Castos came along as a result of that. Podcasting has been the door through which all of this stuff has opened up to me.
Rob: Podcasting has been a great thread for you. Obviously, you’ve listened to podcasts for years, then you started your own, then you started a productized service that does podcast editing, and you have a quite a client list. As you said, PodcastMotor allowed you to quit your day job. Then, you have acquired a WordPress plugin that will get to podcasting and then turn that into a SaaS. It’s not often you actually see a thread like that where there are 4-5 different levels in the same space.
I do think that’s been one of your super powers is you haven’t wandered all over the place. You had invoicing software, then an SEO tool, then email service provider, and started a conference. You’d be an idiot to do something like that and wander all over the place. You have just been focused, but you’ve been able to do it in a much more succinct timeline. When did PodcastMotor start?
Craig: PodcastMotor started 4½ years ago. The very beginning of 2015.
Rob: You were working at a day job and you’re good at sales, presumably, that’s what you’re doing at 40-50 hours a week. The PodcastMotor process involved that super power, I’m guessing. There was a lot of demos in sales because it’s several hundred dollars a month for you to produce episodes for folks. I’m imagining, everybody wanted to get on a phone call. Did you find that that asset of being a salesperson and being comfortable with demos helped you a lot getting PodcastMotor off the ground?
Craig: Absolutely. At first, I was doing the sales calls, doing the editing, doing the writing, publishing to the hosting platforms and stuff, and then we built a team around it. For a very long time, actually up until just about a month ago, I’ve been doing all the sales calls. Just because I’m really good at it, we close a lot of customers, and like you said, we’re really fortunate to be able to work with a lot of the podcast that people that listen to the show probably have heard of.
It’s really cool. It’s been a really nice experience to be able to have relationships with folks like that, too, that we’re on a first name basis and able to email up a whole lot of these power players especially in our space.
Rob: PodcastMotor grew to the point where you were able to quit your day job and then fund other stuff you’re doing. Was there a point in the first, let’s say, 12-18 months where you were like, “Oh, […]. This isn’t going to work,” or, “Man, this is really hard right now,” or was it one of those Cinderella stories that I often say don’t exist?
My famous quote is, “Even in the Cinderella stories, blah, blah, blah, and there are no Cinderella stories.” I’ve been saying that. I don’t recall PodcastMotor being that hard for you to get off the ground. I guess, to summarize, what was the hardest part or the lowest point as you were building that?
Craig: It was both. It was really successful really quickly, which in a service business is really hard, because in a SaaS business, if you make it and a bunch of people sign up, there’s no more work for you other than maybe support. PodcastMotor is a relatively complex one to scale the team up, create all these processes, documentation, workflows and stuff to be able to handle to go from 5 customers to 30 is really hard. It was not hard in the fact that the business floundered, but that the business was successful, which is its own problems. That was the challenge. For a long time, I loathe the business because it was just a constant game of catch-up.
Now, I have a lot more respect for it because productized service model is absolutely fantastic for folks who are out there and they’re consulting or they have a day job and they want to quit their day job and go out on their own. There’s no faster, more clear way to do it than a productized service. There are some downsides, like scalability is a lot harder, but for folks who just want to quit their day job, there’s nothing better because it’s pretty simple.
Rob: I’ve never run a productized consulting… actually that’s not true. CMSthemer was that and that was a constant pain in my ass. I had a bunch of other stuff for products and CMSthemer was bringing in more revenue than a lot of them, but it was this constant back-and-forth with clients and I didn’t have enough volume to hire the staff to do it, so I was doing it a lot of it myself. Were you working the day job, then you’d come home and then you just work four, five, or six hours at night to keep up before you had the bandwidth to hire someone to replace yourself?
Craig: Absolutely, and that’s the hardest part in any business. Whether it’s a productized service or it’s a SaaS business, that time when you’re making a few thousand bucks to even $10,000 MRR is just really hard because you don’t have the time or the money to really do anything. That’s why stuff like TinySeed is really cool because your sweet spot with TinySeed is to take these folks that are that $5000 or even $10,000 and say, “Okay, stop messing around with your day job, go all in on this, and really dedicate yourself to marketing, or hire someone from marketing, or hire a developer, so you can go do marketing or something.”
That is the point that probably a lot of folks get burnt out on is, “I have all of these demands on my time and my mental energy and my stress is through the roof,” because yeah, you’re working a day job and you have family or whatever, then you come home, work on this, and there’s a fire to put out every day. If there’s no light at the end of the tunnel in some way, then it’s just really depressing sometimes, which is weird because then, you have this growing business that is making you depressed. It’s a strange thing, but that’s how it was.
Rob: Yeah, there’s so much to be said for the power of focus. The ability to just focus on one thing and not have a day job and side projects in addition to whatever it is you’re doing, and to your point about folks who have $5000 MRR or sub-$10,000 MRR and are depressed, shutting business down. I’ve seen that over and over and I’ve seen folks trying to do it nights and weekends for years, unable to get it past that point where they are able to quit the day job. It’s a real shame.
There are businesses that could have succeeded or could succeed faster if they just had a little more time and a little more of their best energy, the good glucose. Not the, “I just worked in an eight- or nine-hour day from my day job. Now, I commute home and I have three or four hours.” Even if I’m a developer and I can write the code, you’re just so tired, you’re not as productive, and you don’t get in the flow. There’s a lot to be said there.
Can you give us an idea of how large PodcastMotor is? I know you don’t talk about your top line revenue. Have you ever talked about number of clients or any idea, maybe even employee headcount? Something to give us an idea of the scope of the business?
Craig: We do about $30,000 a month and most of it is recurring.
Rob: That’s cool. How long after you started PodcastMotor were you able to basically quit the day job?
Craig: About two years.
Rob: Did it take that long to get to the point where it could provide a full-time income for you or were you working a job and also banking extra money in preparation for that event?
Craig: It was a little bit of both, it was more that we had wished we had a day in mind. We had a day in mind for a really long time, almost a year. My wife and I agreed, with some stuff with the kids and them finishing preschool, we wanted to quit around the summer so we could travel to Europe for three months. We just had a day in mind and the day included some personal stuff. It included PodcastMotor getting to a certain size so it could provide for us. I was in sales, so you’re making pretty good money which was allowing us to save up for this transition time, too.
Rob: I know it grew pretty well from the start. I almost would have thought the productized consulting given how quickly it can scale up, would’ve allow you to quit your day job before two years. It sounds like it would have if you really were desperate.
Back in 2008, I was just clawing and scratching to get out of the day job. The moment that I was able to, I quit If you had done it at the moment, that you had enough income to do it, it sounds like it would have been a lot sooner.
Craig: Totally. I mean, I’m always been reinvesting more back into the business than maybe I have to, and it’s venture for both Castos and PodcastMotor where the businesses don’t throw off as much profit as they could certainly, but I’m just always oriented towards growth. We were hiring team members, getting people in place, and doing all these things to where I didn’t get as much money. When I had a day job, I didn’t “need it,” but if I had to quit my day job or if I’d gotten fired, we could have lived off PodcastMotor pretty early on.
Rob: The next thing I want to touch on is your acquisition of a WordPress plugin called Seriously Simple Podcasting. This is a plugin that folks who run WordPress or want to run a podcast, they install the plugin and then when they do a new post, it allows them to upload an MP3 file and have that go into an RSS feed in iTunes, settings and all that stuff.
To the listeners, we on Startups for the Rest of Us were on PodPress for ages and it was abandoned. It did the similar functionality and it was abandoned six years ago. We just never upgraded because you just don’t do these things. You came in and generously offered to migrate us to Seriously Simple Podcasting. We’ve been on it now for about a month or two and really enjoying the more modern interface, the maintained code base, and all the things that we were lacking with PodPress.
This very podcast that runs on that plugin, but you didn’t build that, you acquired it. I wanted to dig in a little bit on that story. Namely, when did it happen in this timeline? Right now, we’re at two years after starting PodcastMotor, you’ve quit your day job. Did the acquisition happen before or after that? How did it come about? Just talk us through that process.
Craig: I had already quit my day job, we’re already in France, and it came about just an email from actually one of our PodcastMotor customers who is also in the WordPress space, emailed me and said, “Hey, the guy who’s the original creator of this plugin is selling it because he’s going to work at Automatic, the parent company of WordPress. I think you should talk to him. This sounds like a pretty interesting fit for what you’re already doing with PodcastMotor.”
I talked to Hugh Lashbrooke, the guy that wrote the plugin. Pretty quickly he was like, “Yep, this is a good fit because you’re a reasonable person, already in the space, you’ll probably take good care of it,” and we saw it as a way to expand what we’re already doing with PodcastMotor as a service business getting into a product business and SaaS, and the idea was always to build a hosting platform to connect to the plugin. The plugin, like all plugins in the WordPress repository, is entirely free and will always be entirely free. Now, the Castos hosting platform is an optional add-on to the plugin and we use the traffic flow and the lead gen from WordPress like our main source of business.
Rob: Did you think from the start, when you are evaluating the purchase of the plugin, was it in the back of your mind like this is going to be good traffic and lead gen flow to a SaaS app someday?
Craig: No, it was dumb luck. Very fortunately, but it turns out to be one of the best decisions I’ve made in a long time.
Rob: That’s the thing. If I’ve learned anything doing all the entrepreneurship stuff, the podcasting, and being in public is doing things in public creates opportunity. I don’t care whether you’re blogging about things, whether you’re podcasting, whether you’re actually have a productized business, a productized consulting business like you do where you have a SaaS app, if you had not started a podcast then decided to do PodcastMotor, you would never have gotten that email. No one would pick you out of the blue and it happened to be, “Oh, this guy’s already in the podcast.” There was some warm relationships there, there was a recommendation by someone saying, “Hey, he’ll take good care of it because we already know he’s proven this and that.”
I often give this advice to folks who can’t ship, or who are either have been working on something for years, or thinking about it or, “I just don’t know what to do to start,” I often say, “Just start podcasting or start writing. Even if you want to ultimately do software products just get out in the world, build a small tool and ship it. Help bloggers, help podcasters, help developers, something that gets you out in the world and has your name in the footer.” You’ll be shocked at how many of these little things come along just from being out there.
Craig: One of the things we all discount too much is just the value of your relationships with human beings, talking to them on the phone, and meeting them in person and stuff. We go to conferences, like MicroConf, or like […] Conf, or whatever maybe once a year and you meet up with all of your online friends. That’s really great, but I think that, especially if you’re talking about developing business acumen and a real network, that we should all take this a lot more seriously than most of us do. I was definitely on that boat. I was like, “I have my computer and run a business.” Now, I could run a really good business without a computer and just talk to people and work it like a regular business, where it’s all the relationships and the people that operate in the business and that I know in the industry and stuff. It’s an interesting flip that that’s taken.
Rob: I’ve totally seen that in my career as well. A lot of it starts with nuts and bolts, providing a service in marketing in a funnel, split testing, and then at a certain point there’s a lower leverage activities for you now because now it’s working relationships, it’s building partnerships, it’s shaking hands, and like you said, at an event that can get you hundreds of customers right off the bat rather than grinding it out with AdWords as the case may be.
To give listeners an idea of maybe the magnitude of the plugin, I know you haven’t talked about purchase price, you don’t have to name an exact number but to give listeners just some context what realm of numbers did you pay for Seriously Simple Podcasting.
Craig: I paid mid-four figures for the plugin, and at the time it was an entirely free plugin with some add-on modules which are also free and had about between 10,000 and 20,000 active installs in WordPress.
Rob: That sounds like a good deal to me.
Craig: Yeah, it was a great deal.
Rob: Long term, knowing what it turned into, obviously was a genius maneuver that I know you architected from the start.
Craig: Oh yeah.
Rob: From day one, I knew it. But even then, it sounds like that was a good exchange. You acquire this plugin, this is your first exposure to WordPress. I know you’ve used it as a podcast host or whatever, but you first time owning and operating a plugin, how long after the acquisition did you think we should build a SaaS app to back this thing?
Craig: That was always the idea, was to buy the plugin, to build a hosting platform on top of it because the model had already been proven. There’s another player in the space that does a very similar thing. I think we do it better, but there’s someone else that already does the exact same thing, basically. Our idea was, “If there’s already a player doing this in a certain way, I think we can do it better, because there are some things about that tool that I don’t like and a lot of other people don’t like.” That was the idea from the beginning.
Rob: And the rest is history, to be honest. You build Castos, it’s a SaaS app, a big channel has been your WordPress stuff. I know you have a lot of other channels at this point growing the company. Castos is about 2½ years old, four full-time, two-part time folks. Successful SaaS app on all metrics and I know your MRR—we won’t announce it here on the show—but it’s successful by any measure.
I’m curious, there’s a couple questions I have for you. The first is, podcast hosting is a very competitive and almost I say quasi-commoditized space, there are a lot of them. It’s commoditized in the way that email service providers are. There’s differentiation. It’s not truly a commodity, but there are just so many that you could go out and throw a rock and hit three. What made you think that you could enter that space just 2½ years ago after there are already as many as there were and gain enough traction to build a real business on it?
Craig: Even now and for sure back then, the thing that sets us apart from most all other players is the plugin and our WordPress integration. It makes managing your podcast content just so easy. It is Seriously Simple Podcasting. All joking aside, you just go into WordPress, you create a post, you upload the file, and your podcast is live as opposed to, “I’m going to log into Libsyn, I’m going to go over here, upload the file, then I get this iframe code which is all janky, then take it back to my WordPress site, make sure the post is published at the same time and all this kind of stuff.” There’s none of that. You just manage all your content wherever you’re managing all of your content already, which for a lot of people is WordPress.
I still believe that if I wasn’t the owner of Castos, I would still use it because it’s the best tool for my workflow, because I use WordPress for all of my sites. I manage all of my content in WordPress, so it’s the obvious tool and I would tell anyone else that. If you have a site on WordPress and you want to start a podcast, it’s just the clear, easy, good way to go.
That’s our competitive advantage. I think we have a pretty good moat around that. It would be hard for somebody to create a plugin that does as much as we do, get the traction, the name recognition and everything. I’m sure somebody could and maybe somebody will after hearing this, and that’s cool. Competition is healthy, it validates the space a lot, but that at this point, we’re a long way down that road, so it’s a pretty defendable competitive advantage for us.
Rob: Early mover advantage with stuff like WordPress plugins, SEO. I often think of WordPress plugins just as another form of SEO. If you get a plugin with a bunch of five-star reviews in the WordPress plugin repository, then you appear at or near the top of the search results when people search for podcast plugin. It just dumps hundreds or thousands of people through your funnel. And it’s a free funnel, so it’s not like they’re eating your website, but they’re downloading the plugin and then from there, you nurture them. This is a playbook where we’re seeing folks do, whether they’re moving them towards the premium plugin add-ons to a free one or towards a SaaS app as you’ve done.
Craig: Free like a puppy Rob. WordPress and WordPress plugins are not free.
Craig: It’s an expensive channel to maintain, but a very high-quality one.
Rob: Yeah, no doubt. Again, coming back to non-technical founder, you don’t write code, but you’re a more technical person than most salespeople that I’ve met. It probably comes from you selling medical devices. You have that left-brain edge and I know that you’re savvy with some of the tech stuff, just not a coder yourself. I’m curious what the hardest thing has been for you as a non-technical founder building and maintaining a SaaS app?
Craig: I know that Jonathan, our early developer for Castos, listens to this podcast so he’s going to laugh when he hears this. At the beginning, it was just him and I. He’s been our developer since day one. He started about two weeks after we acquired the plugin. We have had quite the journey of how we communicate, how we plan, how we work together, and it’s just been really challenging. It’s not anything to do with him because he’s actually been really great and gracious and forgiving of me.
For most non-technical folks, learning how to communicate effectively, and maybe efficiently is the right word, with developers is the hardest part. They speak a different language, but just being really, really clear the first time about what you want to build and why, what the user experience is going to be and all of these things.
Even to a developer that is a western person, that native English is their first language—Jonathan is both of those, he’s from South Africa—even though I would consider him a really, really good senior developer, I would come and say, “Hey, I want to go build this thing,” and he would go build it. I would come back and say, “This is not what I meant,” and he would say, “Yeah, that’s what you said.” So, just some of those things. It’s not even just scoping a feature. It’s how we track, report, decide which bugs to fix, in what order, prioritize the workload and stuff. All of this project management stuff is just really challenging. At this point, we do a pretty good job of it, but for the first year at least, it was just fires every day.
Rob: Can you give me an example of one time that you remember where you feel like you really struggled and basically did an example of what you’re talking about?
Craig: I can’t think of an example, but the classic thing, actually I’ve heard Hiten Shah talk about this recently. He calls it dropping Hiten bombs. He’ll just come in and say, “Hey, we should do this thing sometime,” and then the person that “works” for you says “Wow, Hiten or Craig, thinks that’s a really important thing. I should go do that.” That’s the biggest specific challenge for me, is organizing my thoughts and my product road map into something that’s really predictable and clear, and that we can all follow in the same way, not just scattered message and Slack every day, and changing directions on a whim. That’s just an impossible way to work. Getting over that has been huge.
Rob: I can see that. It’s amazing that if you’re like me—you and I are similar in personality—you view yourself as a scrappy founder who just wants to get stuff done, worked a day job, you built something, you’re the same person you were 10 years ago, but you’re not viewed that way by the people you hire. When you have a team and whether it’s 4 or 40 people, you still feel like you can just brainstorm like you did back in the day with a co-founder or with a mastermind group, “Yeah, I’m thinking about doing this, this, and that.”
You’re right. The Hiten bomb concept, I’ve seen it over and over with founders of you throw out an idea and it just train wrecks everybody or your thought process is really anxiety-provoking. It can be really anxiety provoking. If you say something one day and then change your mind the next day and you’re like, “No, it was just a brainstorm. It was just something I was thinking.” Folks don’t know that, and they’re trying to get a job done. I wonder, is that just learning to be a manager? A boss? Or is it learning to be communicating with developers? Maybe both.
Craig: It’s definitely more of the former. Also being more mature. I hate to say that because I’m going to be 40 next year. I need to chill out a little bit about some of these stuff and say, “Okay, the house is not on fire. We have a really great product and plugin, and everything is super stable. If I can just keep my mouth shut for another two weeks until the sprint is over, then we can talk about this.” That’s where I am these days.
Rob: As we move towards wrapping up, it seems like a tangent question or whatever, but I know that especially folks who listen to RougeStartups or maybe who have their own podcast and are building their own product on the side might be wondering, do you feel RougeStartups as your podcast you’ve been hosting for many years, do you feel like that’s had an impact on your ability to launch and grow Castos.
Craig: Totally, and I think in two ways. One is that, it is what first got me into PodcastMotor which is the door that got me into running my own businesses and was the introduction that got us into Seriously Simple Podcasting. The other reason probably is the more applicable to everybody, is that it really is honed to my niche expertise. I am pretty knowledgeable about podcasting because I run a podcast and I run a productized service around podcasting where we help a lot of really good podcasters run their podcast. Now, I run a SaaS app and a WordPress plugin around podcasting.
I just have a lot of domain expertise around this. The show itself, probably like Startups for the Rest of Us, is a really good channel to get your name out and build brand equity and stuff like that directly. Our show has helped grow Castos directly some, but more so, it has allowed us to make a lot of really good product and marketing decisions. The vast majority of our thousands of customers, I don’t know and don’t come from our listener base. That tells me that the podcast probably has helped us a little bit, but more than anything, we’ve built something that people really like.
Rob: And I would guess that the podcast has helped you more with a couple things. One, knowing what to build and knowing how to support people who are editing and posting podcast because you run a company that does it, know how to help folks who are creating podcasts, because you create one. You do have an expertise that most people even building podcast hosting SaaS apps don’t have. You have the whole gambit of being a listener, creator, and running a company that edits and produces them.
That’s one thing, but the other thing is I’m guessing that RougeStartups probably helped you more with credibility, perhaps with potential affiliates or partners like in space in the MicroConf world, they’d probably know you from RougeStartups. I’m guessing even PodcastMotor clients.
Those would be the folks that would email. I’ll admit, I’ve received at least—just over the years—probably two or three emails asking about, “Do you know Craig? Do you know about PodcastMotor? Are they legit?” that kind of stuff.
Early on, the way I first heard about you was RougeStartups. You spoke at MicroConf Europe a couple of years ago, you’re speaking again in two months, and the first time I invited you was because I had listened to you talk on this podcast for months and I was like, “This guy is sharp. He knows what he’s talking about. I think he’ll do well on stage.”
You would come to MicroConf and I believe we had met, but I meet a lot of people at MicroConf. It’s like you were in my ear buds literally six months or nine months and that was a piece of it. I’m not saying you speaking at MicroConf Europe, but you and I knowing each other has changed the course of anything, but that’s probably one of 50 examples that’s come out of it.
Craig: Yeah. Podcasting even here, getting into the fourth quarter of 2019 is probably the best use of time that anybody can put into personal branding. It’s wonderful. It’s really efficient from a time perspective. You just spend 45 minutes recording a show, edit it a little bit, or send it to somebody like PodcastMotor, or find a guy on Upwork to edit it for you, and then you get 45 minutes and a bunch of people’s ears every week. It’s just really impactful as a medium for building brand awareness, and getting your name out there.
Rob: You’re not just saying that because you run an editing service.
Craig: I’m hugely biased. Yeah.
Rob: Totally. Take it from someone like me who doesn’t run an editing and hosting service. I’ve been talking about this for years. Mike and I show up every week. We shoot a show every week and I stopped blogging years ago. I really want to blog, I just don’t have/make the time to do it, but I do make the time to podcast because it is so much less of an effort.
We need to talk offline about getting Startups for the Rest of Us moved over to Castos in the next couple weeks. Let’s figure out a good time for that to happen. We’re already on Seriously Simple Podcasting and my understanding is the move to get all of our files. Right now, for listeners, we set it up in 2010, so we literally have flat files, MP3, flat files, just sitting on a shared hosting account and a CDN over that.
We could have done Libsyn in 2010, they were the only host that I know of and they were so janky, and a lot more expensive than what we have because I have somewhat a limited shared hosting account. We’ve done that for nine years and frankly, there’s just a lot of challenges with that approach, I’ll leave it at that, and we’ve been looking at getting a legit podcast host for several years for the metrics and all that stuff, but it’s probably time we do it.
Craig: We’d love to.
Rob: Sounds great. Thanks again for coming on the show. I know folks want to keep up with Castos, they can go to castos.com. If they want to follow you, if they’re into podcasts of course, check out RougeStartups on iTunes, Stitcher, and all the other places. Where else might they keep up with what you’re up to?
Craig: The best place is probably on Twitter. I’m @TheCraigHewitt on Twitter and I tweet less often than I should, but that’s probably the easiest place to reach out and say, “Hey.”
Rob: Sounds great man. Thanks again for coming on the show.
Craig: My pleasure. Thanks.
Rob: I hope you enjoyed my interview with Craig. Again, if you have any questions that you’d like to hear Craig and I talk through on the show, please email email@example.com or call our voicemail number at (888) 801-9690. Thanks for listening. We’ll see you next time.