Episode 357 | Courtland Allen – Indie Hackers

Show Notes

In this episode of Startups For The Rest Of Us, Mike interviews Courtland Allen of Indie Hackers, about commonly held expectations new founders have about their businesses.

Items mentioned in this episode:


Mike: In this episode of Startups For The Rest Of Us, I’m going to be talking to Courtland Allen from Indie Hackers about surprising discoveries that new founders learn. This is Startups For The Rest Of Us Episode 357. Welcome to Startups For the Rest of Us, the podcast that helps developers, designers, and entrepreneurs be awesome at building, launching, and growing software products, whether you’ve built your first product or you’re just thinking about it. I’m Mike.

Courtland: And I’m Courtland.

Mike: We’re here to share our experiences to help you avoid the same mistakes we’ve made. How are you doing this week, Courtland?

Courtland: I’m doing excellent, little bit sick, little bit overworked. Other than that, doing great.

Mike: It is Friday. For the listeners, it will be Tuesday but it is Friday for us. Hopefully, you’ll be better by the weekend.

Courtland: I’m getting into the habit of having weekends. Usually, everyday is the same to me, but my girlfriend is helping me develop better, healthier work habits. Looking forward to the weekend as well.

Mike: Excellent.

Why don’t you give me a brief introduction to you if the listeners aren’t familiar with what you’ve done and what your background is. You’ve run a popular community for aspiring entrepreneurs and founders called the Indie Hackers which has a series of interviews and blog posts and various articles on there that entrepreneurs and founders can learn from. Indie Hackers was recently acquired by Stripe as well, right?

Courtland: Yup, been with Stripe for five months now.

Mike: How’s that going? It’s interesting to hear from somebody who is acquired by Striped. I’ve talked to the guys at Stripe, Patrick McKenzie who’s also a friend of the show and a frequent speaker at Micro Conf has moved over to Stripe as well. It’s interesting to hear about the transition from owning your own thing and going into Stripe.

Courtland: I have to say that Patrick, by the way, is great. I’ve gotten the chance to hang out with him at the Stripe HQ a couple of times that he’s been in the US and he’s been very helpful. I always tell people at Stripe when they ask me how it’s been, Stripe is my first full time job. I’m 30 years old, I’ve always worked on startups and as an entrepreneur since I graduated college. A lot of ways, I was worried before I joined that I wouldn’t like it. But also, Patrick Collison has been so amazing, the way that they handled the acquisition was exactly how you should handle acquisitions in my opinion, which is to be as hands off as possible.

My life hasn’t changed very much since before joining Stripe, now that I’m at Stripe. They made things easier to run. Before I joined Stripe, I was basically financing Indie Hackers by selling advertising. I had ads in the email newsletter, on the podcast, on the website itself. That was something that took up so much time. I got to about $5,000 a month in revenue by the time I was acquired, but I was beginning to spend half of my time on ads. The most helpful thing that Stripe has done is just paid me a salary so I don’t have to worry on any of that, but I’ve been able to focus much more on the quality of the website itself and improving the community. Joining Stripe was a great decision, I think. I’m excited to see where things go in the future.

Mike: Interestingly enough, there’s kind of a corollary there where 100% of your revenue probably came from those ads. If you’re spending 50% of your time on it, then you’ve got 50% of your time free to do whatever.

Courtland: That’s true.

Mike: Wanted to talk to you today just because you’ve got a lot of experience talking to various founders and entrepreneurs. Obviously, you’ve got your own podcast that goes along with Indie Hackers where you interview founders and talk to them about what has gone into their business, what sorts of successes and failures they’ve had along the way. I thought it would be interesting to have you on to talk about some of the commonly held expectations that new founders have that don’t necessarily hold up to reality. Obviously, you’re gonna draw some of the various examples and stuff but also from your own experience and background running Indie Hackers as well.

Courtland: Yeah, totally. I think it’s tricky being a startup founder, especially if it’s your first time, because as a consumer, as a normal member of society, your view into what happens at any company is extremely limited. We generally see information that they put out there that they want you to see, but you don’t really see what goes on behind the scenes. When you start, I think you tend to be driven by your intuition and by what you’ve experienced as a consumer, but it turns out that actually being a founder and starting a company is completely different than it looks. People end up falling in the same holes, same pitfalls, same mistakes that others have fallen into simply because they don’t know what to expect.

I think it’s definitely worthwhile to talk about what’s surprising and what might you not expect that you should expect when you become a founder.

Mike: I think there’s a lot of these types of examples where people will hear them and I say oh yeah, that’s kind of obvious. What’s obvious to you is not necessarily obvious to everybody else. There’s certainly traps that you can fall into yourself that there’s lots of other people who would say well, that’s kind of obvious to me, how did that happen to you? I think that just reiterating some of these and talking through them about what are probably the most common ones that people fall into or experience that are not necessarily things that they think about in advance, is it worthwhile talking about?

I guess with that said, let’s dive right in. The first one that I wanted to talk about was the runway needed to get a startup going. Again, to limit the discussion, we’re not really talking about funded startups. It’s stuff that you’re either bootstrapping or self funding, building on the weekend or on the side in addition to your day job, in an effort to eventually go solo or try to establish a source of income to either be in addition to or to replace your existing income from a full time job.

The first thing to talk about there is when you’re leaving a full time job to go solo, what are the sort of things that you have seen and heard from people that have made the decision to leave their full time job and go solo? Are there mistakes that people make or assumptions that they make that later on they find that are just completely invalid?

Courtland: Yeah, I think probably the biggest mistake is just underestimating the amount of time it takes to actually work on a startup. I have never been in a situation where I’ve had a full time job and I’ve had to run a startup on the side, but I’ve heard from a lot of people who have. It’s extremely difficult to do. Number one, you’re probably going to be somewhat mentally exhausted after a full day of work. Building something on nights on weekends is going to take a toll on you.

I think it really comes down to being ruthless at prioritization. Ultimately, you’re not going to have time to do everything you want to do. Your task list is going to be growing faster than you can get things accomplished. It comes down to being able to prioritize and putting the most important things first and actually being able to recognize what’s the most important and what might seem important that you can actually get away with not doing.

There’s a lot of cool stories as well on Indie Hackers of people who have found creative ways to get around this challenge. For example, Mike Perham of Sidekiq, it’s an open source plugin for developers to basically allow their servers to run tasks in the background. He was able to convince his employer to allow him to work on his projects at work. The reason was that he was basically the CTO of his company, he was in charge of all their technology decisions, and so he built Sidekiq on the side at home and then he used it as his only customer on the job. This way, he was able to discover bugs and actually contribute to it, because it was open sourced, while at work. He kind of cheat the system and figured out a way to actually get more hours into his project while he was working a full time job.

I’ve seen other people do similar things as well. I think the expectation that you will be able to just go to work and come home and essentially put in non-distracted, 100% productive hours over a long period of time is probably not true for a lot of people. If you can find a clever way to allow yourself to work more hours on your project or to work it into what you’re normally doing, then that’s advantageous.

Mike: I really like the phrase you just used where you said “cheat the system” but I also, for anyone who hasn’t listened to that episode, I don’t want them to think that he was going behind his employer’s back or anything. He worked with them to figure out a solution and I think that’s the key takeaway from that, finding creative ways to solve the problem that you have which is not having the time, or you come home from work and you just don’t have the energy left to do it. I’ve heard people who said, “I’m going to get up at 5:00AM and work on my product for two hours before I have to go to work.” That’s a solution to it, there’s other solutions like working one weekend day a week and just work from 8:00AM to 10:00PM or something like that. There’s lots of ways you can squeeze more hours out of the day. I think it’s really about identifying those places where you can leverage creative solutions to the problems that you have.

Courtland: Exactly. I think we’ll probably talk a little bit about this later. Depending on your situation and how much free time you actually have to devote to your project, you should probably decide what you want to work on based on that. What I mean is if you have a full time job and if you have a family and if you have all sorts of responsibilities that give you a limited amount of time to work on your project, you probably shouldn’t pick the most ambitious project.

If you’re going to work on a SaaS application that’s going to require six months to develop and build, then that’s something that’s better suited to someone who has more time. There’s an entire spectrum of projects that you can work on. Indie Hackers itself being a content site didn’t take that much time for me to get out the door even though I was working on it full time, versus something like Bluetick which you’re working on which I can only assume is a completely full time job.

Mike: Yeah, it’s way more than a full time job, to be honest. I don’t want to even go back to my rescue time account every month and look at how many hours I’ve spent. It’s a lot. But that’s because it’s a SaaS product and I also recognize going into it. It was going to take a long time. But if you don’t have the time to be able to put into it, you’re trying to go from ground zero all the way to SaaS which is kind of a holy grail, it’s very difficult to make that transition if you’re not doing a stair step approach, which is what Rob has talked about quite a few times on this podcast and various talks that he’s done.

You have to be able to leverage your way into either larger projects or more lucrative products that you can put out there by using the assets that you created in advance. It’s like going to the gym, you can’t just go to the gym on day one, put in a three hour workout, you’re not going to be able to sustain that. You’re probably going to hurt yourself the very first day, just similar with starting a business. You’re probably going to do things that are essentially going to kill the business before it even really got started

Courtland: Yup, I think that’s exactly what happens. It’s difficult not to do that when it’s your first time because you’re looking around and all the examples that you see are these 300 pound guys at the gym who are established and can lift a lot of weight, these established companies that are building extremely ambitious products. You might think that’s what everybody does, I should do the same, but it’s not necessarily the case.

Mike: I think another thing that people underestimate when they’re trying to figure out what sort of runway they need or how to really get started is they don’t have a good sense of what the expected growth trajectory is for the business. When you’re starting out, if you haven’t started a bunch of businesses or tried to launch a bunch of things, it’s very difficult to make comparisons between what you’re doing now versus what you’ve done in the past to give yourself a basis first comparison that tells you whether or not you’re doing well in relation to previous things you’ve done, or whether you’re getting the traction you need to move forward.

What sorts of things have you seen that people can use as benchmarks to help them establish that sort of thing? If somebody doesn’t have previous things that they’ve worked on, what can they use as a basis for comparison to determine how well they’re doing with their startup?

Courtland: That’s a tricky thing as well. I think it leads into one of the next things we’re going to talk about which is the psychological aspect of being a founder. In reality, being a founder is very unique. If you’ve worked at a company before and you’ve had a job where you filled a very specific role, it’s almost completely different than being a founder where you’re going to have to wear every single hat. The metrics that matter are less, can you fill this one specific role, but are people using your product? Are people signing up? Are you finding users, are you increasing the revenue? That requires you to, like I said, wear a whole bunch of different hats and do a bunch of different things.

I think it’s difficult to compare to anything that you might’ve done before if it’s your first startup. As a result when there aren’t these clear cut comparisons that you can look at, you start to compare yourself to other people, you start to hit on this emotional startup rollercoaster type thing where you use your emotions to tell you how you’re doing. You get an email from a customer and you think oh, things are going great, I’m going to succeed. Or you get a scathing email from a customer who says they’ve run into a bug, you think oh, my startup is doomed.

I think people tend to underestimate the degree to which you fall back to that short sided, short term thinking, into the value of your overall progress. I’m not sure what the exact solution is, it’s different for everybody. I know that being able to talk to people, being able to zoom out and look at the bigger picture, have some sort of a plan can really help you with your ability to evaluate whether or not what you’re doing is going well.

Mike: I think that just having some sort of guidance or advice from people that are not in your own head, they’re able to look at what you’re doing or experiencing a little bit more objectively, is extremely helpful. Whether that’s people in a mastermind group or just other entrepreneurs that you talk to online, or even professional therapy for example.

I’ve been hearing more and more over the past couple of years, people, especially entrepreneurs, going to a professional therapist and talking to them about not just their life but also about their business and how things are going, different techniques that they can use to help get off of the emotional rollercoaster where not only is there the way that they feel about their life very heavily influenced by how their business is doing, but also the things that they do are driven by some of those emotions.

For example, if you’re not getting a lot of traction with your software, I see a lot of people making the mistake of trying to feature their way out of it and they’re building more and more things but none of those things actually get them more customers. They do it because it makes them feel better, but it’s kind of masking the problem which is I don’t have any customers and I’m not getting in front of people. Adding another feature, making something work better is not going to fix that.

Courtland: I like what you said about seeing a therapist which is such an unconventional way of approaching it that most people might not think about. As I mentioned on my podcast, my girlfriend is a sex and relationship coach. We also see a therapist for our relationship. Every now and then, I’ll talk to him about Indie Hackers and about how it’s affecting my life, how much time I spend on it, etc. It’s good to be able to talk to somebody who’s willing to sit down and see the problems that you’re going through and understand how all the different parts of your life might come together in ways that you don’t expect. Like you said, the things you do in your personal life can affect the decisions that you make in your business. The ways that you feel might affect the decisions that you make in your business as well.

Also being able to talk to other founders I think is crucial. A lot of people are in the situation where they had a cofounder. What I hear from a lot of people who aren’t in a startup hub like San Francisco or New York for example is that it’s difficult to find people who might understand what it is that you’re going through because starting a startup is such an unconventional life decision to begin with.

Mike: I think the other thing that factors into the professional therapy side of it is the fact that when you’re talking to a therapist, it’s more of a no-judgment zone. If you’re talking to other entrepreneurs, a lot of times in the back of your mind, there’s always those, “How am I doing in relation to them?” “I don’t want to look like an idiot.” Versus when you’re talking to a therapist, you’re paying them to help you understand how to move forward and solve problems. It’s not about them judging you or saying you should do this or you should do that, it’s more about them helping you understand what’s going on, how does that make you feel, and what you can do to change it if it’s not in line with what you want or what you expect.

Courtland: Exactly. It’s so underestimated how much of a role Imposter Syndrome plays in being a founder. Always thinking that other people are a step ahead of you. In reality, it’s easy to feel that way. If you look at other entrepreneurs and you look around at people who are writing blog posts, doing podcasts and giving advice, it’s extremely easy to find somebody who has more experience than you, more knowledge than you, or progressed further than you have just because people in those positions are more likely to have their messages amplified in the first place. That still takes a psychological toll on you.

For sure, being able to talk to somebody in a judgment free zone where they’re really not someone who’s going to judge you for what you’ve done, or really even somebody you can compare yourself to because they themselves aren’t an entrepreneur can be very helpful.

I think also practicing as an entrepreneur, being able to be vulnerable and open with other people about what’s going on. The easiest thing in the world is when somebody asks you what’s going on with their company to say it’s all going great, even if everything is on fire. If you take the time there to really slow down and let people know and let people into what’s going on with you, I think you’ll have much more fulfilling and enjoyable conversations and it will be easier for you to find people who can identify with you because you’re letting them into the hardships that you’re going through.

What entrepreneur doesn’t have hardships that they’re going through? Nobody.

Mike: One of the things that I found over the years… I have a home office, so it’s extremely isolating. If I go out and check the mail and I actually walk outside more than once on any given day, there’s certain periods of the year, especially winter because I live in New England, but there are entire weeks where I will step outside once, maybe twice, to go check the mail or something like that and that’s about it. If it snows, of course I got to go out and snow plow the driveway.

But what’s your experience been? You’ve said that you just started working for Stripe, so before that you worked for yourself. How did you deal with that early on? Was that something that you recognized early on you needed help with and you needed a support group and people to talk to? Or was it something that you had this epiphany one day.

Courtland: I think what’s been really big for me is transparency. I’ve done startups before Indie Hackers and I always had a co-founder. That had made things a little bit easier for me. I’m sort of an introvert, it’s very easy for me to sit at home, working at my desk, and like you said never leave. With the co-founder, that was a little bit easier because at least he was there too and I could go in the other room and talk to somebody.

With Indie Hackers, I basically started it by myself which meant that there was no one I could talk to in my immediate vicinity, there’s no one in my house who I could talk to about what I was doing. But being transparent online, basically vomiting out every fact and detail about what I was working on, whether it’s through blog posts or Twitter or my email newsletter, I found really helped me feel less alone and a little bit less contained. Even being at Stripe, I still work from home most of the time, but I’m a 20 minute walk from the Stripe office which has hundreds of people in it but I work from home almost everyday. I haven’t been into the office a single time in the last week. I think really having an online community of people who are going through similar things and people who care has been helpful for me.

Mike: What you just said about transparency is actually I’d say a little bit counterintuitive, something that I discovered. I think I knew this all along, but about a month or two ago I did this 21-day series of video blog posts before my launch. Every evening, I’d sit down with a glass of whiskey and I’d record a video and then put it out to my mailing list for three weeks straight.

I was actually very, very surprised about the email feedback that I got. There was a bunch of comments and stuff on the blog itself. I got a lot of emails from people that were encouraging and helpful, hey have you thought about this, you mentioned this problem, have you thought about doing this other thing over there? It’s interesting to see how helpful people are. If you become transparent about the stuff that you’re doing, I don’t think it’s obvious to most people that the benefits of doing that actually outweigh the risks of putting yourself out there and being judged.

Courtland: I agree completely. I think this goes back to what I was talking about earlier that unless you start at a company, you’ve had the consumer lens on your entire life. What do you see as a consumer? You see companies being these big corporate walls, always say we, and they never really reveal how the sausage is made and it’s all very neat and packaged. It’s easy to imitate that.

But in reality, if you let your guard down and you talk about what you’re doing, you talk about what’s hard for you and the decisions that you’re trying to make, there’s just something about that that people really connect with. My early newsletters for Indie Hackers have kind of gotten away from this recently, but every newsletter was basically, “Hey, here’s what I’ve been doing with Indie Hackers, here’s what I did this week, here’s what I’m worried about, here’s what I’m thinking about for the future.”

I would also get a ton of email replies from people who were going through similar things, or people who wanted help. Not only is the process of hearing from people extremely motivating and helpful, but just writing it down, writing down what’s hard and telling somebody else felt great. I think it can’t be underestimated, the advantages of being transparent.

We know people aren’t really going to steal your business model and steal everything that you’re doing because you’re sharing your details. The people who do that are oftentimes not the most competent of people.

Mike: It’s funny you say that because I’ve never seen anybody rip off somebody else’s idea and actually make it successful.

Courtland: No. Someone who’s really a go getter and is really talented is probably not going to be sitting around waiting for somebody to reveal their transparent details of their business so they can copy them step by step. Those aren’t the people you have to worry about, and I think the common fears of being transparent are mostly unfounded.

Mike: I guess the next thing to dive into is what sort of resources do you need to get started? When you started Indie Hackers, you said that it was really just you building this on your own. Was it more work than you expected, less work? You said you got it to around $5,000 a month in recurring revenue just from advertising, but how much effort went into that before you got to that point?

Courtland: A lot of effort went into it. It was by far more work than I expected. I think this is the case with pretty much any startup. There’s always going to be more work than you expect. My favorite analogy for this actually came from an article I read years ago about being a programmer and estimating how much time it takes to get something programmed.

The analogy that I used was a map. If you look at a map and you want to chart a course between two different points, you might just draw a straight line and you might draw a slightly curvy line to avoid some mountains or something. But when you actually zoom in close on that map and you look at that line, it becomes much squigglier because you realize that you have to work your way around all sorts of bends and trees and hills and rivers.

I think the same is true of being a programmer and a startup founder. From the outset, you might think okay, I need to hit these giant milestones. But when you actually get into the weeds and start working on it, you end up having to deal with a whole bunch of unexpected things you just couldn’t see when you were zoomed out so it becomes a whole bunch more work than you planned.

With Indie Hackers specifically, the bulk of the work, at least initially, was just doing the interviews and trying to figure out a repeatable, scalable process for doing three to five interviews per week while also building up a website and trying to charge for ads. That process took months and months. I was working at Indie Hackers for three or four months before I even really started focusing on ads. I’ve seen similar patterns with other people. To the degree that you can prioritize and cut features out of your product that are unnecessary and do only the bare minimum that you need, you should do that for sure because even that will take you longer than you expect.

Mike: Before we dig a little bit more into that, why is it that these things take longer than we expect? One of the things that I’ve kind of come across is that I’ll see my expectations for the quality of my own work tend to be high, and I don’t think that people listening to this are probably too dissimilar to that. We have these expectations for things that we’re going to put out in the world. Because we don’t want to be negatively judged for putting out a product that is sub par, we spend a lot of extra time doing things that are probably not necessary. Whether it’s a graphic design polish, or making sure that all the different edge cases are taken care of. We’ll spend a lot more time on things than we probably should in an effort to not look bad. The reality is you can get away with a lot, especially if ppl are not necessarily paying you for that particular feature or that particular piece of your product. People are willing to tolerate a lot of different things.

Courtland: I think something I personally underestimated before I started doing Startups was how much I would care what people thought. If somebody says something negative about something that I felt, it seems like a dagger through the heart. Just trying to avoid that feeling has led me to spend hours working on things that might not be the most crucial for my business’s success and maybe I can actually let those things fall by the waist side. Definitely, I have perfectionist tendencies that force me to some degree to spend time on things that I didn’t need to spend time on. I think this affects a lot of people.

A good example recently was I had a friend—I recently redesigned my newsletter—she told me, “Oh, your new newsletter looks so great. The old one looked kind of crappy.” It’s funny because I took that as a compliment because I knew the old one looked crappy, at least by my own design standards and I had been able to successfully fight off the urge to redesign it for as long as I did. That was progress for me.

Mike: Other ways that you’ve found to protect—I don’t want to say fragile ego—I think all of us have a fragile ego to some extent where you can get 10 emails that say, “Hey, you’re doing a great job.” And then you get one that says, “This sucks.” That one outweighs the other 10. Are there things that you found that protect yourself from those types of things? I’ve run into that myself, I’m not saying those are the exact numbers. The negative stuff weighs on you substantially more than the positive stuff.

Courtland: It really does. I think that’s just a part of being human. For me, it’s not even negative emails, it’s Hacker News that’s the worst for me. I put a lot of content on Hacker News, which for those of you who don’t know, is a community site for developers. People there are trolls very often. They’ll say lots of negative things, they’ll leave drive-by negative comments without really even thinking and it hurts.

The thing that helps me the most is just getting people on my side. Nowadays, I work with my brother who Stripe also hired to help me with Indie Hackers. When we see negative comments, we’ll both basically talk about them and talk about whether they have any merit and reassure each other. I think that’s extremely helpful. When you’re sitting in a vacuum and there’s nobody on your side, there’s nobody that can talk to you who can take your side and say you’re right, or this person’s wrong, or don’t listen to them, then I think it weighs on you a lot more.

Mike: The thing that you just said about being able to talk to your brother about some of the stuff that comes in, there’s a big difference between something that is simply a troll comment where it is much more of a personal attack versus a legitimate criticism of a piece of your work that isn’t right for somebody based on their situation, or it’s broken. There’s a very big difference between those two things. Sometimes, that line is very much blurred and it weighs on us regardless.

Courtland: It really does. I’m the type of person that almost, no matter what kind of negative feedback I get from a stranger on the internet, it’s going to weigh on me. Whether it’s legitimate or illegitimate, whether it’s private or other people can see it, I’m going to think about it for a while. Like you said, it’s going to stand out more in my mind than 10 positive comments.

I think that it’s something that as a founder you need to be prepared for. I don’t know if there’s a great way to prepare for it other than just to expect it and know it’s going to happen. One of the things that I told myself early on was that it’s very hard to get people on the internet to care at all. Most things that people put out there never get any attention, never get any comments whatsoever. If people are giving you negative comments, then at least they care to some degree.

Mike: We talked a little bit about the fact that everything takes more time than you expect it to. I think there’s also a corollary there, and this kind of especially applies to marketing endeavors or development. I think there’s this false equivalent of time being the same as money when you’re trying to put your marketing efforts out there. Everything that you do that’s marketing related is going to cost you money or a lot of money that you may not necessarily have. You don’t want to risk that if it’s not going to work, so people tend to do these little experiments that are not really statistically relevant but at the same time they do them because that’s the budget that they’re comfortable spending.

I think the general point that I’m trying to make there is that when people do that, they have this idea in their head that I want to do an infographic, and to hire a designer, it’s going to cost me $1,000 to have that done. It’s too much money. I’m just not going to do it. Versus doing it themselves and not spending the money to do it but yes it’s not going to look as good, but at the same time it still gets done and it can achieve the goals as long as they put a marketing slant on it. It’s really about being creative in your marketing efforts in a way that doesn’t break your bank.

Courtland: What do you think is the biggest misconception there in terms of what people expect versus what actually happens?

Mike: There’s two sides of that. I think that there’s your own expectation for what it should be or should look like, versus what people on the receiving end are going to think or look at and evaluate. When you’re doing a new marketing campaign for example, you want to make it as top notch as possible because you want to get the most impact, you want to get the most conversions, highest number of clickthroughs, and all that stuff. Of course your thought is hey, I need you to do a fantastic job on this.

The reality is on the other side, people don’t evaluate those types of things for more than a few seconds unless they get to the point where they’re actually going to click through and maybe read an article that you wrote. But with paid ads for example, there’s a headline. That’s the most important thing on the whole ad. If you don’t nail the headline, everything else doesn’t matter at all.

I’ve seen advertisements, I’ve mentioned this to Rob once, I saw an advertisement on Facebook, it was a snake. It wasn’t even a real snake, it was just this weird thing that showed up in my Facebook feed. It caught my eye. I don’t know how much he was paying for it but the fact that it caught my eye was enough to make me notice it and look over at it and say huh, I wonder what that is, and then I saw that it said Drip on it. Really, that’s what you’re trying to do, you’re trying to catch people’s attention. If you get the right people to look at it, then they’ll come through and they’ll click through and take a look at the other stuff and look at the quality of what you’ve got, whether it’s the writing, or the marketing collateral that goes with it.

Just catching their attention is really the main goal, not having the best designed thing. You don’t need to spend as much money as Buffer does on an infographic, for example. That’s kinda the point I’m trying to make, you can probably get away with a lot less than you think you need.

Courtland: That makes a lot of sense. I think even more broadly, that reminds me of this thing I’ve been harping out a lot in the last few weeks just by talking to people on the Indie Hackers’ forum about their landing pages and about their product ideas how important it is to realize that what you see as a founder and how you look at what you’re putting out is not the same as other people see it. It’s not the same viewpoint that your customers have, it’s not the same viewpoint that your partners might have. Being able to step outside of yourself and look at things from their perspective might be the number one quality that you need to have as a founder.

I’ve underestimated this to a huge degree. Especially early on in my career, I spent a lot of time doing things based on my intuition. Whatever I felt was important had to be what everybody else felt was important. I would work on that, and then I would realize that nobody cared what I thought was important. I wasn’t solving the problem that they wanted.

I think the example that you just gave is a really good one. If you’re crafting an ad or if you’re designing your newsletter, if you’re planning out your marketing campaigns, it’s very important to look at what it is that your customers or that your visitors are going to care about and try to prioritize those things first rather than prioritizing the things that you might intuitively feel are okay as a creator.

I think this is probably true in almost any sort of creative endeavor. My brother’s a writer. One of the hardest things for any writer to do is to be able to step outside of themselves and look at their story and their writing from the reader’s perspective. Sometimes, it takes a few weeks of not writing and stepping back and looking at what you’ve written later on with fresh eyes. I think the same thing can be true as a founder. Whether you’re talking about coming up with an idea, is this an idea that customers actually want, is this something that solves a problem that’s valuable to them, or is this a feature that you really want them to add because you thought it was cool?

Mike: Features is another one that we spend a lot of time building certain features that some customers just don’t even care about. I’ve done this myself but I’ve also talked to people. I think I answered an email this morning where somebody was talking about how they just wanted to implement this one more feature before they launched. The reality is that’s a snowball where you can always look, “I’m going to do this other feature, do this other feature,” and you’re always delaying that launch in order to delay judgment on all the work and effort that you put into it. If you delay it long enough, then you never get judged. You’re really putting yourself in this position where you’re never going to win because the game never starts, I guess.

Courtland: That’s totally true. It’s subtle. You might not be conscious of the fact that you’re doing it to make yourself feel better and to avoid judgment, it’s easy to convince yourself that you really do need this particular feature. Once that’s over, you really do need this other feature. I think this is something that generally if you’re starting a business, it’s advantageous if you have some development skills and you can code what you’re working on yourself rather than having to hire out. It’s also a trap that developers fall into more so than other people, specifically because if you have that ability to do something, if you’re really good at writing code, it feels good to write code and it’s easy for that to be the answer to everything. When in reality, there’s all these other hats that you need to wear, that you need to actually get your product out the door to succeed. Features is a really big trap that a lot of first time founders fall into, just taking too long to launch.

There are other traps there too as well, I think. One of the biggest reasons why I see founders fail and why founders tell me that they end up failing is because they quit early. They essentially hadn’t really put in the time that they needed to solve their particular problems that were [00:32:04] their businesses from succeeding. Often, it comes down to the psychological issue of they didn’t have enough wins under their belt, they were feeling demoralized about their project, it was this long death march, it was building features and never really getting any traffic, trying random marketing efforts and never really have any success.

That gets amplified under fold if you take six months to build a product because you’re continually adding features. Whereas if you build something, a good example would be Josh Pigford of Baremetrics who got his first product out the door and his first customer in something like eight days. He didn’t have time to get demoralized and quit, so not only is it helpful to build things quickly in order to talk to customers and it actually succeed, but it’s helpful for your own morale.

Mike: I think putting something in front of them faster allows you to get the feedback to course correct when you start to go in the wrong direction. As you said earlier, there’s a difference between how you perceive things versus how your customers perceive things. It’s very easy to confuse the two and think that you know what they need. And then when you know what they need, and then when you put it in front of them, they point out all these flaws that you didn’t think of or consider that make you have to go in a different direction. By delaying putting it in front of them, you’re just delaying the results of getting that feedback or results of getting that feedback so that then you have to make the course correction. It’s three months down the road instead of three weeks.

Courtland: I think a lot of it comes down to the curse of knowledge where this really affects creators in any industry, not just founders. Ultimately, if you spend a lot of time working on something, you end up building all sorts of mental models that describe how it works. You’ll understand all of your features better than your customers do, you’ll understand all of your copy better than your customers do, and it can be difficult to tease apart what you understand but it’s not clear to your customers, versus things that are clear to your customers. It kind of gets in the way of you being able to be as effective as you would like.

You’re sitting here thinking oh it all makes so much sense and your customer’s like I don’t get it, you send your landing page to your friend and they say I have no idea what I’m supposed to do here. I think talking to people and getting out of this solo solitary lifestyle where you’re just working by yourself without talking to anybody is extremely helpful. It’s hard to break out of that because as a founder you’re essentially responsible for everything, it’s kind of the default that you don’t talk to anybody and you’re constantly handling this avalanche of work.

Mike: I wonder if there’s a predisposition for software developers to have that mode of operation just because I almost feel like in order to be a software developer, it almost feels like you have to have introverted tendencies because you sit in front of a computer all day, you don’t talk to people, and people who are introverted would be more drawn to that line of work because they don’t have to talk to somebody. But it hurts you when you’re trying to build a business. If your goal is to have this lifestyle where you sit in front of a computer all day and you don’t talk to anybody. That’s the ideal life for you and that’s what you’re working towards. It makes it difficult when you put yourself in a position where in order to be successful, you have to talk to people.

That leads us into a lifestyle of being an entrepreneur and what is it really like versus what you thought it was going to be like when you first started.

Courtland: What you just said reminds me a lot of how I decided to start Indie Hackers. I had three or four other ideas that I was strongly considering, and I knew from my history, “When you’re a developer in the past, you’ve always tended to spend way more time coding than getting the product out the door, and you found every excuse under the sun to delay marketing.” I picked Indie Hackers as an idea because I knew that the product itself was just a blog, the actual work that would go into it would require me to do the marketing, require me to talk to people.

I think that’s kind of a hack that you can use if you’re aware that you maybe are a little bit more introverted, that you have a tendency to put off stuff that you’re not good at or that you don’t like like marketing. Pick an idea where the product itself is easy relative to the marketing part of it, so that you very quickly run into a wall where the only thing that’s left is the marketing.

Mike: That’s really just play into your own personal strength. I don’t think that it’s going to be possible in most cases to build a business where you never talk to anybody. You’re going to have to get out and talk to somebody at some point. A customer is going to have a question, you’re going to have to get feedback on what it is that somebody really needs versus what you thought that they needed. Otherwise, you’re in this position where you’ve put something out there.

As you said, the world doesn’t care. You post something on the internet and nobody cares. That’s the worst thing for a product launch or anything that you put out there, you post it and you get zero traffic and nobody bats an eye because they didn’t even know about it.

Courtland: Yeah, exactly. That’s unfortunately what happened to I think probably the majority of startups. It’s important to be aware that even if you have a successful launch and things do go really well and people do know about it, that’s not the end of the story and it never is the end of the story. I think it’s an expectation that a lot of people have, “I just launched, got a lot of traffic, word of mouth took over from there.” That almost never happens. In reality, you’re still on the hook for figuring out a sustainable growth strategy and a marketing strategy. That job pretty much never ends because in every single stage of your business, the techniques that work change. You have to figure out a new way to get your product into more customer hands.

I think it’s important to be aware of that. In many ways, just being aware of the fact that it’s never really over and that no matter what level of success you achieve, it’s always going to be more work to the next level will help prevent you from becoming demoralized when things don’t go that well.

Mike: Do you think there’s a danger in that where you’re going to be in a situation where you don’t have all the answers because you don’t have all the data for a particular problem? Kind of going back to your example with Indie Hackers, you said that you spent a couple of months on it, three to six months, before you even started working on the advertising side. You were working on it, did you know in advance that this is going to be an advertising model and that’s where the revenue was going to come from? Or was that you kind of had that as an idea but you hadn’t really thought it out or flushed it out or had customers waiting in the wings when you got the product itself done?

I wonder how prevalent that problem is where people delay those types of problems, or spend too much time on them, there’s the opposite of that. They just delay doing anything before they have solved all the problems, then they never get anything done.

Courtland: I think my particular situation was that I was basically doing that. The problem that I really wanted to solve with Indie Hackers was traffic. I wanted a repeatable way to get people in the door, reading articles, and I didn’t feel comfortable moving on towards revenue and finding advertisements to work with until I was confident that I was going to be able to bring more people in. Then at a certain point, I said you know what, the traffic is high enough, I should start making money. I hadn’t solved that problem but I just got to it.

In hindsight, I really could’ve started focusing on generating revenue. I probably should’ve from day one, there’s nothing stopping me from doing it back then. I wouldn’t say that I was spinning my wheels but I was definitely working on something that should’ve been less of a priority. I really should’ve focused on revenue more. I think a lot of startups come down to prioritization.

Working on a startup is more work than it appears from the outset. Every task that you work on will probably give you the idea for three to four more things to work on, three or four more bugs to fix, additional features to add. Your to-do list generally grows faster than you’re working on it. It really comes down to prioritization, how do you know what’s the most important thing to work on and how do you know what you can toss out.

Mike: I think there’s people—I have some perfectionist tendencies sometimes. The one thing that I’ve realized is that—in my younger years—I would look at what a business was working on. An example that jumps into my head was Oracle’s installer was absolutely awful. It never worked the first time I ran it. It was like that for 10 years. It never worked. I always had to go in and mess around with stuff and get it to work. The installer would always fail. I’m like how is Oracle successful when their installer doesn’t even work? Of course, it just made me angry.

I look back on it now and it’s like well, once they’re past the initial hurdle, the installer doesn’t matter. To solve that, oh, just hire these professional consulting services to come in and they’ll install it for you. Just like oh yeah, not only does it put money in their pocket, but it also gets around the problem. They don’t have to fix the problem. Then, it’s interesting to see those types of decisions that in retrospect, oh, that totally makes sense, but at the time it was in theory.

I think there’s a lot of places where that prioritization, there’s creative problem solving that you can do inside the business to get around or avoid solving problems that aren’t really that important to solve for you. You want to have everything perfect, but the reality is you don’t have time because as you said, your todo list is going to expand much faster than your ability to get everything done.

Courtland: Yeah, just getting comfortable with that state of affairs I think is extremely important as a founder, just knowing and accepting that you’re not going to get everything done. You’re better served if you’re aware of that up front.

Also, to your point with the Oracle example, I think probably the most common source of bad ideas is people looking at a product that’s successful, finding some highly visible flaw of that product and saying I’m going to make the UI look a little bit nicer, or I’m going to make this part be a little bit better designed. I’ll do a much better job than Oracle does and not really realizing that the reason why they slacked on that part of that product is because it’s not actually as important as it might seem. As an outsider looking in, it might be difficult to determine what’s important. A lot of times when you see successful companies that are doing well but are crappy looking, it’s because they know something that you don’t about what’s important and what actually drives the business and what’s not, they’re just prioritizing.

Let me ask you, what do you think about work-life balance, Mike?

Mike: I think work-life balance, if you have a home office, is extremely hard. If you’re at your computer, if your computer is in your living room for example, it can be very difficult to draw lines between when you’re working and when you’re not. It just makes things a lot harder than it probably would be otherwise. On those distinctions, especially if you’re a solo founder and you don’t have a co-founder or anything like that, it’s just a hard problem to solve. I don’t know if I have any great recommendations for that, to be perfectly honest, what about you? I think you said that you have a home office, how do you establish any boundaries between work and nonwork time?

Courtland: I, for one, am terrible at establishing these kind of boundaries. I’m somewhat of a workaholic, but I’m getting better at it. I think the key is to realize that as a founder, you’re always going to have distractions. We’ve talked about it a number of times, your to-do list is always going to be infinite. You’re always going to have more things that you can get done, and you’re probably also going to be getting a lot of email which is extremely interruptive. It can sometimes be urgent. You’re going to have to deal with that stuff at times where it might be inconvenient. You don’t have a boss so you can just say I’m not going to work at these points in time, you’re your own boss and it’s up to you to determine your schedule.

I’ve talked to people who have varying degrees of success in doing this. For example, I talked to [00:42:56] a couple of weeks ago. He basically works a 9:00AM to 5:00PM, 9:00AM to 6:00PM schedule, leaves his laptop upstairs, and refuses to bring it downstairs when it’s time to hang out with his family. That works for some people and I think if you have the discipline to set a schedule like that, it can be extremely productive because being always on and always working means that you’re likely to be pretty inefficient. I don’t know if there’s a secret technique or magic bullet for solving that, but it’s important to be aware that your work will never feel like it’s done. It’s not like a normal job where 5:00PM comes around and you’re done on your own. You need to really have the discipline to make rules like that for yourself and figure out what works for you and your business.

Mike: I think that goes back to the prioritization of the tasks on your task list as well. It’s like what is it that is important to you? I think there is a wide range of opinions on this. DHH from Base Camp has constantly railed about the working hours of Silicon Valley and how people should come to work and they’re paid to be there for 40 hours a week so don’t make them work 60 or 80. The fact that you’re working longer hours is not necessarily a badge of honor.

But I think there’s the flip side of it where there are some people, like if they are workaholic and they enjoy the work that they’re doing, then working 50, 60, 80 hours a week, that’s fun to them. I think that there’s this broad spectrum that people fall into and there’s no right or wrong answers, it’s what is right or wrong for you, not for everyone. I don’t think that there’s a general case answer that you can apply to everyone, there’s a wide range of answers and some apply to some people and some apply to others. I don’t think it’s wise to say that this is the way that it should be done for everyone just because it works for you.

Courtland: Yeah, I think it’s also worse experimenting. Sometimes, you don’t know what really works for you unless you’ve tried a bunch of different things. I, for example, thought I really like the idea of being a remote worker and going to different places and working from the beach, or from a coffee shop, or from a friend’s apartment. I tried that early on in my startup career and it just did not work for me, I was very unproductive, I spent a lot of time doing all sorts of side things besides actually getting into the groove that I’d like to fall into. Turns out though, what works for me the best is to just sit at home. It’s kinda boring but I get by far the most work done. I think I wouldn’t have really realized that unless I attempted to experiment. I think it’s worth trying out different things.

Mike: I’m in the same boat as you. I cannot take a laptop and go to a coffee shop and sit there for a little while. I know that it works for some people but it absolutely does not work for me at all. I just can’t get work done. It doesn’t work for me. As you said, you won’t know until you try it.

Courtland: Yeah, exactly. Something that’s been surprising for me also to add to that list is even though I rarely go into the office to work at Stripe, when I do, I have very productive days. I think a lot of it just comes down to everybody can see what’s on my monitor, so I can’t exactly do a bunch of random stuff and watch YouTube videos, whereas at home those distractions are my own private distractions. Again, definitely worth experimenting and seeing what works for you.

Mike: We’re kind of running short on time here, but I did want to touch on one last topic here. That was about what are the expected success levels or income levels after various time frames? I think this is a case where it kinda goes back to what people’s expectations are about either the runway that they need or the resources they need or the time they need to build the products and make it successful.

You’ve interviewed dozens of people so far for Indie Hackers. What is the range of timeframes it has taken for people to start something from ground zero and make it successful to the point that they can go full time on it?

Courtland: This is a good question because it’s difficult to answer because it turns out that when people start out their business, it’s actually a much fuzzier line than you might think, looking from the outside in. Sometimes, it’s very clear cut. They started their business on August 11, launched it, and then it was successful in two years. But often times, people’s businesses succeed based on things they did well before they started their business.

One thing that I get a lot of feedback on is someone will have a company and they’ll start it and get a lot of customers. People will say, “That guy cheated. He already had an audience beforehand,” Or “He already built a list beforehand and he used that to bootstrap his business.” “They already had a lot of expertise in one particular area, and that’s the only reason she was able to start this company. In situations like that, it’s hard to say when was the real start date?

It’s tough because as a founder, you end up comparing yourself to other people’s success. It’s not always visible when they really started doing these things that were crucial to their success. I’ve seen a huge variety of levels. The other thing that’s worth talking about startups is that they kind of follow a power law distribution where a very small percentage of startups will grow way faster and way bigger than others. You’ll always have those people present in the limelight where it’s very easy to compare yourself to them. But in reality, it’s such a huge range that you shouldn’t compare yourself only to the top people.

You should be aware that if it takes you two years to grow your business to the point where it can sustain your lifestyle, that’s perfectly fine, it’s not at all abnormal. If it takes you three years, that’s also perfectly fine and not at all abnormal. I would caution people to not expect or hope that they’re going to find some overnight success, it’s probably not going to happen in a couple of months or six months or even a year.

Mike: Yeah, that reminds me of a talk that Harry Hollander from Moraware Software gave an attendee’s talk at MicroConf a few years ago. He said that if he calculated back to when he started the business to that point which was I think 8, or 10, or 12 years, or something like that, he had just gotten to the point where he would make the same amount of money as he stayed at his previous job. It’s interesting to see that because it does illustrate the point that one, it takes longer than you think it will, but there’s all these other things that factor into it that you didn’t expect when you got started.

Courtland: Yeah, I definitely would not go into startups expecting to get rich or get rich overnight. I think it’s probably the most common reason that people go into it but I’m in the same boat. If I had just gotten a software engineering job after college, I would be doing a lot better financially than I am now having done startups. That’s not true for everyone, some people make a lot of money doing it. But I think there are other benefits worth looking into.

Personally for me, what’s really motivating is I like financial freedom, knowing that I’m basically the one in control of my finances. I like the locational freedom and being able to go where I want whenever I want. I like the time, being able to work on my own schedule. I like the freedom to determine the vision for the product that I’m building. I think all those things are their own reward for me.

I will also caution people not to get too sucked up into this idea that they’re going to be an overnight financial success and make millions of dollars.

Mike: Yeah, all those things that you just touched on, they’re the ancillary benefits of being a founder. You can’t necessarily get them from a full time job. Sometimes you can, obviously there’s financial rewards for having a full time income and you don’t have to pay for your own health insurance for example, that’s fantastic. But the freedom to come go as you choose, and work on things you want to, and not do the things that you don’t. So long as they don’t drive your business into the ground, it’s okay to ignore some of those things. You have to pick and choose your battles and there are going to be times where you’re going to have to do stuff that you don’t want to do and you don’t like to do but it’s part of business and it may not be why you signed up for it but it’s still gotta get done.

Courtland: That’s a really good point, actually. A huge percentage of the things that I do are not my favorite thing. If I was only doing my favorite thing, I would just be writing code all day everyday but that’s maybe 5% or 10% with what I do with my business and what I’ve done with businesses in the past. Whenever I go over that limit, it’s because I’m being irresponsible and not doing the things that I actually should be doing. That’s not to say that I don’t like the other parts of running the business, I think I’ve really begun to appreciate some of the more marketing type tasks, even some of the more extroverted talking to people and interviewing customers and interacting with people.

7I’ve really started to appreciate that. It’s important to realize that as a founder, you’re going to have to do whatever is required of you, and that’s not always going to be your favorite thing. If you prioritize only doing your favorite thing in your business, then chances are you’ll be spending a lot of time on things that your business doesn’t need and neglecting things that your business does.

Mike: Ultimately, I think those things will probably come back to bite you. You can’t avoid the things that are going to make your business successful. You can’t always do the things that you just want to do because they’re not going to benefit the company and it’s not going to make the numbers that you need in order to make your own payroll. You have to buckle down sometimes.

Courtland: Yeah, you really do. I think that’s another reason why it’s important to choose to do something in a field that you care about and that you like. I started Indie Hackers because I like startups, I really like the idea of revenue generating startups that don’t necessarily have to follow the Silicon Valley model of raising a ton of money. I could talk to people about it all day. No matter what, even if I’m doing mundane tasks that I don’t particularly care for, at least I’m doing it in a service or something that I do care for. That’s helped me stay motivated even when the times are tough. Very easy to underestimate how easy it is to quit when things aren’t going your way for 3 weeks straight or 3 months straight or 10 months straight. I can’t recommend enough to work on something that is actually meaningful to you and is not just an opportunistic business play.

Mike: Speaking of opportunistic business plays, how can people get in touch with you? You say you enjoy hearing from people, wrapping things up here, where can people find out more about you or get in touch with you if they have followup questions?

Courtland: I’m pretty active on Twitter, I try to be, @CSAllen. Obviously, I’d love to hear from you on indiehackers.com where we’ve got a community forum there where all sorts of entrepreneurs go to ask each other questions, get feedback. If you create a thread on the forum, I will almost certainly see it and try to give a response, or you can just email me courtland@indiehackers.com.

Mike: Courtland, thanks for coming on, really appreciate having you on the show. Look forward to more episodes of Indie Hackers.

Courtland: Thanks for having me on, Mike.

Mike: If you have a question for us, you can call it into our voicemail number at 1-888-801-9690 or you can email it to us at questions@startupsfortherestofus.com. Our theme music is an excerpt from We’re Outta Control by MoOt used under Creative Commons. Subscribe to us in iTunes by searching for Startups and visit startupsfortherestofus.com for a full transcript of each episode. Thanks for listening, we’ll see you next time.

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One Response to “Episode 357 | Courtland Allen – Indie Hackers”

  1. Awesome like always!