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Episode 445 | Why Absolute Thinking Is ALWAYS Bad


Show Notes

In this episode of Startups For The Rest Of Us, Rob and Mike talk about some of the pitfalls of absolute thinking. Things are rarely black and white, they are more nuanced and on a spectrum. The guys explore the advantages to this approach.

Items mentioned in this episode:


Rob: In this episode of Startups for the Rest of Us, Mike and I talk about why absolute thinking is always bad. This is Startups for the Rest of Us Episode 445.

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 Rob.

Mike: And I’m Mike.

Rob: We’re here to share our experiences to help you avoid the same mistakes we’ve made. Did you catch the joke? The sarcasm in the title there?

Mike: Just a little. Is it always though? Is it always bad?

Rob: Always bad. We’re going to dive into always and never, absolute, thinking in this episode. But before we do that, what’s the word this week, sir?

Mike: I’m still going through hell that is the Google authentication approval process. I feel like it’s on of those ongoing sagas, kind of like Game of Thrones right now, where like the last episode’s coming up and you’re just like, “Ugh, just let it end.” It’s going to take a little while. They sent me an email. I asked them for more information. They said, “We signed up.” This is me going on a rant here. But they signed up for Bluetick apparently and then they ran into the credit card screen, and then they email me saying, “We need you to make our account so that we can log into your application and bypass the payment information.” I’m just thinking to myself, I’m like, “You’re Google. I imagine that somewhere, there’s a credit card that you could put it in for the 14-day trial.” I would just imagined it that would be the case some place.

Of course, I email them. It was a week later, still nothing from them. I was just like, “I need an email address. What email address did you signed up with?” I didn’t hear a word from them and then they’re like, “You have five days to comply.” I’m like, “Come on!”

Rob: Oh, boy.

Mike: This coming Monday is when they’re like, “You have five days to comply. These are the steps that we’re going through. We’re going to start notifying people, your users that are connected.” I’m like, “Come on!” It’s just ridiculous. I don’t know how that all is going to turnout over the next couple of weeks. It’s just frustrating and irritating.

Of course, at the bottom of it, it’s one of those worst case scenarios where they’re going to detail about, “You’re not going to be able to add any new users using Google Gmail accounts.” I’m like, “Come on!” Basically, they’re taking aim and saying, “Well, if you don’t do this, we’re going to tank your business” Like, “Thanks.”

Rob: It’s a little bit like dealing with the state government or the federal government.

Mike: Only with them, you can just pay a fine or penalty or late fee or something like that. They’re threatening to shut things off. I’m just like, “This just sucks!”

Rob: Would you say, never build on top of Google, Mike? […] for the next episode, never trust Google. It’s not never but know what you’re getting into. Is that it?

Mike: I think what it would boil down to is that if a company removes, don’t be evil from their company motto. It is probably not wise to rely on them not being evil.

Rob: Right. You might say, “I will never build on Google again.” Or, “Know the pros and cons of basically building a business that relies on them.” That’s tough. It’s a similar thing that I’ve dealt with with setting up payroll in multiple states where you like Gusto, I guess, Zenefits, and there’s a few others that like it appears that it makes it just magical like, “Get payroll running. It’s no problem.” Then you have to sign up for at least two janky online web accounts that were built in 1997 with state governments to get the revenue, Office of the Revenue of the state, and then, it’s like the unemployment stuff so that it can pay into this. Then, you have to give Gusto access. That never works the first four times.

It’s not threatening to tank a business but it is something that adds a bunch of back and forth, that’s frustrating, that you can’t actually get it done, that you really can’t outsource to someone. That was the thing that I always struggled with. You almost need a chief operating officer or an office manager who’s really going to dig in and do it but it’s kind of something you just have to deal with. It’s just a headache that wastes time and it’s not the fun part—one of the many not fun parts—of running a business.

Mike: Yeah. The other thing is how opaque the whole process is. It’s Google. They’re kind of like Facebook or Apple. You have no way to talk to a real person. I guess with Apple, it’s a little different, you could go to the Apple store. Even then, if you need to talk to somebody, an engineer or something like that, I’ve only heard of one situation where somebody was able to get an Apple engineer who was in the design engineering office in Apple. It was because something literally caught on fire, with some charging cable or something like that. It was like the second or third time that it happened. They’re like, “I want to talk to that person.” That’s the only one that I have ever heard of. Just getting somebody to talk to, to say, “How is this supposed to actually work? What’s the next step? How do I talk to somebody about getting either a waiver or something like that or an extension?” Nothing, there’s no information, and they’re not forthcoming with it. Anyway, I will leave it at that. How about you?

Rob: Yeah. We can stop. Google Rants for the Rest of Us. I wanted to give a shoutout and a thank you to Rich Staats. He runs which is a WordPress agency. It’s spelled s-t-a-c-h-e like a mustache, It’s a WordPress agency. You and I have met him at different Big Snow Tiny Conf. He comes to MicroConf as well. We were having some issues, to put it mildly, some minor issues with the Startups for the Rest of Us website because it’s on a, do we think a nine-year-old WordPress theme? Eight-year-old? Nine-year-old? It’s pretty ancient. It’s like 70 in human years.

Mike: Yeah.

Rob: It’s not like an eight-year-old WordPress theme. I think it’s nine years.

Mike: Yeah.

Rob: Anyways, he dove in. He helped us out, really appreciated it. Now, our comments appear. When people are making comments, we can see them in the admin, but they wouldn’t appear on the actual episode. As such, we have few comments that I haven’t read through over the past couple of months.

Episode 432, you and I talked about How to Indirectly Overcome Sales Objections and Matt made a comment. He said, “Great episode! I love the idea of using KB articles to overcome sales objections. I’m trying to figure out what knowledgebase I should use. It looks like they can get pretty pricey. Mike, I like the look of your KB at Is that something you built yourself or are you somehow using a service for that?

Mike: I’m using Teamwork Desk for that. It’s just a redirect with my DNS. It just redirects over to that. It’s all completely hosted there. They’ve got stuff where it integrates into their desk products as well. If I’m answering a question or somebody has a problem and there’s a KB article on it, I can link directly to that KB article from within Teamwork Desk. Works quite well. You can have multiple mailboxes setup, it’s charged per user. I found it to work pretty well so far. That’s what I use.

I think there’s a lot of other ones that do something similar where they will have a KB article hosted for you or a set of KB articles. But that was one that I found that was simple and easy to get into. It just kind of worked and met my needs for the time being.

Rob: It makes a lot of sense. When you’re small, you have a support system—email support—where you’re already using it. I would say Teamwork Desk or Help Scout would be my two top recommendations for that. Both of them have built in KBS. It’s probably a little bit of extra money per month. I don’t even know, but that’s a totally viable option if you want it hosted.

What we did at Drip, and it worked out fine. I don’t know at this point that I would do it again. I was trying to be budget conscious and I don’t want to pay a bunch of money at that time. We had a WordPress install, it was on WP Engine, and we used the KnowHow theme and customized it a little bit to look like we have Drip colors. It worked great for us. It was essentially free because I already was paying for this WP Engine account. That’s another option. Of course then, you have all the maintenance and all that stuff that goes along with WordPress. It just feels like it gets worse and worse overtime. Those are some two relatively inexpensive options depending on how you want to go.

Mike: Yeah. I went with Teamwork Desk mainly because it also offered—I forgot what they call them—but it’s basically a part time account as well for free. If you have somebody who needs to log into the ticketing system and they only need to see tickets once in a while or you only need them to have answer once in a while then, the part time agents basically takeover. They can answer, I think, up to 10 for free. Then, your regular users, I think, I’m still only paying $8 or $10 a month or something like that. It’s really cheap for what I’m using.

I didn’t need very much either. It’s not like I needed higher end stuff where I need to have advance workflows. I didn’t really care about sending out satisfactions surveys to people because it’s not like I was getting a larger number of tickets. I’m still not. It’s not like I need to move off it. It’s a great place to start though.

Rob: Indeed. We have another comment. It was episode 433 where we answered several listener questions. In that episode, we talked about VidHug which is a B2C service that, if I recall, was doing around 500 or 600 a month MRR. You could send out a link. It was kind of B2C. Let’s say it was your grandma’s birthday and you could send all the links out to all the relatives. They could record something on their iPhone and it was stitched together a happy birthday video. That was the concept.

Tyler made a comment. He said, “Hey, Rob and Mike. Don’t if they’d be interested, but VidHug sounds like a great idea for small businesses looking for testimonials. They can invite their customers to leave testimonials then the company can use those videos for Facebook ads as social proof. That could be a B2B opportunity with recurring revenue. Was wondering if you could pass that along because I would pay for that now. Just a thought I had while listening. Keep up the great work! Thanks, guys!”

I thought that was kind of clever. Probably a better use because I think the VidHug founder had asked about switching to B2B and going after HR and having them do welcome videos and stuff. I almost like this better because it’s an easier sales process than going after HR departments.

Mike: Yeah. The only downside, I would say, that I see there is if you’re going after testimonials, how many testimonials do people go after in a particular year? You’re not going to constantly be doing that. It almost feels like there’s a—I don’t want to say it’s a one time fee, but it’s like a fee for a three-month period or something like that. You’re using it and it’s used during that time period and then after that, you’re probably not going to use it again for another six months or year or something like that. The pricing might be an issue. How you price it might be an issue. But if you don’t care that it’s recurring then it doesn’t matter. If you’re just going after customers to get them as customers and try to establish revenue, then it doesn’t matter.

Rob: Yup. I would agree with that. You could do a three-month or you can do an annual and just make it annual-only pricing or something.

Last comment for the day before we dive in. Episode 434, SaaS KPIs You Should Focus on From Day 1. Oh, this is a comment relating to when you sent out, I believe it was this scholarship applications, and you forgot the email. You forgot to put the email in the form and you had something like 70 of them or something that you had to go through. Anna says, “Lol! I totally noticed that you didn’t have an email field in the MicroConf application. I just figured that we were living in a post-email world and you’d DM everyone on Twitter. That did make me feel like I was way too old though and that MicroConf was going to be too hip for me, so I’m glad to hear that it was an accident!” We’re not in a post-email world. […] of getting there, so I thought that was funny.

Mike: It’s funny because I was still able to track down pretty much everybody on there. I don’t think there was anyone I couldn’t trackdown or wasn’t able to eventually get an email address for. Yeah, I’m shocked. I had enough information to be able to track people down, but it was still time consuming. It’s not a post-email world, but I guess given enough time, you could make it a post-email world but you’d have to have enough information too.

Rob: Right. Cool. Let’s dive in. Today as I said, the title’s a bit of a joke, Why Absolute Thinking is Always Bad. The alternate title is Why Absolute Thinking Can be Toxic to you, your business, and other people who are kind of listening to you. I think, if you’re wondering what absolute thinking is, it’s that very black and white view of things. Examples of that are, if you see someone say, “This always works. You should always do this.” Always is the key. “This never works. You should never do this.” Often times, it’s like, “I should do this.” Maybe that’s an absolute feeling but it’s kind of like an assumption or a burden you’re putting on yourself.

The reason I want to talk about this today, because we were talking about it before recording, and you were like, “What’s the point of pointing out that something as bad?” It’s because I believe that successful founders, and frankly, successful humans, that I like to have conversations with, stay away from absolute thinking and see the nuance in complex things instead of trying to break them down to black or white or zero to ones. I believe the entire startup community itself will be better off if there’s just less of this. If there are fewer of us that believe that there are these absolute, “You should always never do this.” We have examples later on, on this episode of actual examples that I’ve heard over the years, frankly.

I believe it’s a fallacy. It’s thinking that it isn’t true. It’s more than semantics. It’s not digging in. When someone says, “Always,” and they mean 95% of the time, that’s a very different thing. There are exceptions to most of these things. There are times when absolute thinking is useful with ethics and in genocide. There are things when, “Yes, this is always bad.” That’s why the title is a joke. I think we’re going to give some specific examples of marketing approaches and that kind of stuff that I think will lend a little more detail to what we’re thinking about here.

Mike: This almost goes back a little bit to what I kind of opened up MicroConf with this year which is the fact that the matter is, when we go to MicroConf, and we’re talking to all these other founders, that we’re essentially raising the bar for every single person there just because we’re learning from each other. I definitely think this is one of those things where we can learn a lot from it.

I do want to dig a little bit to the piece that you said on, if somebody says, “Always do this.” What they really mean is 95% of the time. How do you differentiate between what they meant to say versus what they actually said? A lot of time, I see a lot of these stuff come up on Twitter, for example, or in places where there’s not a lot of room to expound upon what the person actually meant. Then, there will be people who’ll jumpin in the comments and just rip them apart and say, “That’s not always true.” Or, “Well, actually this and that” How do you differentiate between that? Is it just you have to rely on your own personal knowledge of that? Because if you don’t know anything about it, how would you know it’s 95% versus 50%?

Rob: Yeah. That’s the problem. That’s why words matter. If you say ‘almost’ without exception, or ‘in almost all cases’, or ‘nine times out of ten’, that tends to be how we talk in the podcast. That tends to be how Jason Fried talks now. He didn’t used to be. He used to be more absolute but something I like about his Q & A this year at MicroConf is that he wasn’t nearly as black and white on things as I thinks he was 10 years ago. When I hear Jason Cohen talk, I don’t know that I’ve heard him say ‘always’ or ‘never’. It’s very much same way we think and talk about things where it’s like, “Yeah, in some cases, this and that but as a general rule,” blah blah blah. “As a rule of thumb, I will always…” We already talked about that. You will probably never write another app that relies on Google but you wouldn’t say never do that. You’re not going to tell everyone else they shouldn’t do that because there are pros and cons to it.

That’s where I think it is, the words that matter, language does matter. I think, that’s something we’ve seen over the past 20 years of a lot of language being adopted and people not saying, “Hey, you guys,” anymore when it’s a group of men and women because words matter. That’s what I’m saying here. I think saying ‘always’ and ‘never’ especially if you all caps it on Twitter to make a point, I think that’s detrimental to the folks who don’t know the difference like you’re saying. I also think it can veer the conversation off in a direction that just doesn’t matter. Let’s not debate if it’s the last 5% or the last 1% or whatever. It’s just being careful about how you say things and how you think about things. I think that’s the important part.

Mike: Yeah. I agree with you. The conversation can easily go off into the weeds just because somebody said always and what they really meant was 95% of the time. I think that in most cases, a simple correction but Twitter is also not known for making it easy to go back and edit those things, and provide a correction in a way that makes it visible to everyone who’s going to see it. It just extends the conversation. Rather than continue going off into the weeds, let’s circle us back a little and talk a little bit about the nuances of that.

Rob: What I would say is just be more careful with your first post. Be very thoughtful when you’re going to write and publish a blogpost or say that tweet or whatever. I, very intentionally, try to avoid absolute language and I have for years. Again, the folks who I admire, the folks who I see who are successful, in general, they always do that. No, they don’t always do that but in general, that’s the behavior I see as well.

Coming back to nuance, most of the topics that we’re going to talk about is in the startup space, in the bootstrap space, or in the whole startup ecosystem world of tens and thousands, hundred of thousands of companies, there’s nuance to these things. It tends to be much more a spectrum or a continuum of 1-100 maybe instead of this 0-1 binary thinking.

I remember getting in a conversation, I believe it was on Hacker News, I don’t even remember. But someone posted, “You should never outsource the development of your SaaS product. Never. Never.” I mean, that’s okay advice. It was like, “If you don’t build it, you have zero chance of it working.” That’s just patently not true. It’s not even a 5% exception. I would say that there’s a bunch of stuff that can add up from 1-100. If you’re going to be a solo SaaS founder, let’s say, if you have any of these skills, it will mean you have a higher chance of success. One of those is the development […] is the ability to build your own product. The other one is the ability to manage and hire people. Another one is the ability to market. Another one is the ability to think about the product and build good UX. On and on and on.

If I recall, in that Hacker News article, I made a list of 10 things. I said, “Just weight each of them as a 10 if you have them or 9.9 because you never get to 100.” If you have all 10 of those then you’re at 99 out of 100, you just have the huge chance of success. But most of us don’t, most of us none of us have, all 10 of the things that I threw out. That was a way of thinking about it where it’s like if I were to add it for myself, I have 70 out of 100. People I really respect have 80 out of 100 or whatever.

They have a better chance than others but that’s all it is, it’s a chance. You should always never do these things. It’s more like, “Let’s look at the factors and the list of pros and cons.” I realized, looking at pros and cons is complicated. It takes an advanced frontal lobe developed. That’s why kids often have a hard time doing this. It can be hard and it hurts your brain to think about it. I think that’s important because higher level thinking involves this nuance.

Mike: I wonder if that nuance also comes with time and experience too. The couple of things you had mentioned about these examples of somebody going on social media saying, “She should never outsource those core things.”

I remember there was a couple of articles from Joel Spolsky—I’m looking at them now. One of them is titled, Things You Should Never Do, Part 1. This is from April 6, 2000. He’s talking about basically rewriting an entire application from scratch. It kind of goes into the history of Netscape. The next one is from October 14th of 2001 which is, In Defense of Not-Invented-Here Syndrome. He says, “The best advice I can offer: If it’s a core business function — do it yourself, no matter what.” Both of those things are incredibly absolute. He’s essentially saying, “Never ever do these things.”

I think if you start reading beyond the statements and looking into the context of what he’s providing and all the things around it, you’ll see the rationale. You’ll see the reason why he’s saying that. I think that that context is important for the statement, not necessarily just the statement itself. You’ve got to stake that context into account along with the statement. Staking the statement alone is essentially taking it out of that context. It’s very easy to manipulate it and twist it to say something that he didn’t quite mean. He said it, he didn’t mean that though.

Rob: Yeah. That’s a good point. I bet if you ask Joel today, in 19 years later, I bet he would see a little more nuance in it, I would guess. I think that comes with experience. I think that comes with knowledge and wisdom, just doing more things, and maybe he wouldn’t. Mike, I bet you and I could go to our—you’re in my blogs or essays—right now and find some evidence of some absolute thinking. I bet it’s 10 years ago. I bet it was when I thought I knew everything. I hear my kids, or I hear kids in general, say these black and white things like, “I never get to do this.” Actually, you did that last week. It’s a way of them kind of being dramatic or trying to call attention or showing how really bad it is for them when it’s kind of not, when they’re exaggerating for effect. That kind of leads into this thing about frontal lobe development.

Sherry and I had this conversation where, if you watch a lot of kids movies, they’re very black and white, there’s a good person and a bad person. A protagonist and an antagonist. As you develop and you watch shows like Game of Thrones or Breaking Bad, there’s this really strong nuance. Obviously, I haven’t watched Game of Thrones or Breaking Bad with my 13-year-old, but I have watched shows that have more nuance like in the MCU, in Black Panther, the villain in the first movie, he wasn’t bad. Thanos is another one. He does want to kill half of the people but he has a pretty good reason for it and he believes it. He’s not just doing things to be evil, he actually believe he’s doing good when he does it. It takes development to learn that.

Sherry has talked about how the frontal lobe is your advanced thinking and it doesn’t fully develop until early 20s. I think women are few years ahead of men with that. But this is one of the reasons why you thought you knew everything when you were 16 and why I thought I knew everything when I was 18 or when I was in high school. As you get older, if you get experience and you get knowledge outside of your little box, you don’t live in your little box but you travel and you meet other people with your thoughts. You’re allowed to be shaped. A lot of these happens in college. When you’re 18, you know everything. When you’re 28, you’ll realize you know less. When you’re 38, you’ll realize you know even less and so on.

Mike: Eventually, you get to be our age and you know nothing.

Rob: You know nothing.

Mike: You know nothing Rob Walling.

Rob: Yes. You know how little you know. That’s part of it.

Mike: I don’t want to say, but the way that this comes across is age is just in terms of people being younger. As you become more mature, you get older. You just naturally develop this. I think it’s a datapoint for you look in the mirror and say, “Is this type of thinking actually helpful for me or for other people?” The answer in general, I think, is no. But you have to be aware of it first. You just can’t just magically, you hit a certain age then suddenly you are aware of this. It’s something that develops over time through repeated experience and exposure. I think that’s what we’re trying to do here is, just expose people to the idea that those absolutes without the contexts are probably detrimental not just to you but to other people as well.

Rob: To your audience, that’s really the point. That’s right. It’s detrimental to you and the folks who you’re speaking to who don’t know better.

Mike: Right.

Rob: It’s not that. That’s something you pointed out over there. I am glad you called that out. My intent is not to say, “Oh, as you get older, you get out of absolute thinking.” That was one example of frontal lobe development. But I’ve known folks who were in their late teens who I felt like they had the life experience. They were 18 and they were as not absolute as I was when I was 38. You know what I mean, they were way ahead.

It’s not just some absolute scale of, “As you get older, you get better with this.” I do think it’s probably quite a bit of your upbringing. I was brought up for a black and white. It took me years to break free of that. I think if you’re brought up with more nuance and with parents who really talk things through in a non-absolute way. I think you’re ahead of the game. I think when you have life experience, you’ve traveled outside your home country, and you’ve met a lot of people with different viewpoints, and evaluated those, I think you’re ahead of the game. Again, I’ve know kids, 17, 18, 20, or whatever, who are way ahead of me and other folks that we might encounter on a day-to-day basis.

I think, piggybacking on the experience thing—I’m totally guilty of this, I was guilty of this—when I had my first success back in 2005, 2007, I was like, “Boom! I know it.” The first time entrepreneur typically thinks they have it all figured out. I did too. A few years later, you tend to realize that you didn’t. In research circles, they call it the N-of-1. N is how many subjects you have in an experiment or in a research study. An N of 10,000, meaning you’ve talked to 10,000 people or you researched them or whatever, that gets to be a pretty good number. It’s statistically significant. Depending on how everything varies, an N of 500 can be totally valid. An N-of-1 is a little bit of a joke. It’s basically an anecdote.

I say this because Sherry was a researcher for a while. She did a residency at Yale. There were a lot of researchers there and that was one of their jokes. It was, “Your anecdote is not my data.” Or the singular form of data is not anecdote.

Mike: That’s almost like when I see arguments of people, “Well, that didn’t happened to me,” and they’re arguing against data that they disagree with because of what their experience was. It doesn’t invalidate their experience but they feel like it does. But the data itself indicates something completely different. I can think of any number of things where that stuff has come up. One example that comes up specifically is Patrick Campbell of MicroConf had recently said and provided some data that said, “Companies that are remote first, I believe, are less successful or make less money.”

Rob: Grow slower.

Mike: Oh, that’s what it was. They grow slower than companies that are not which kind of flies in the face of a lot of kind of what we see. It’s not necessarily directly confrontational to it, but a lot of us don’t necessarily have the context of other companies either. I think that’s one of those dangerous things where you have a certain point of view and you believe it is correct but the data doesn’t necessarily prove or support that. You think that you’re right but you don’t necessarily have any data to prove that you’re right or wrong but you have that core belief. Because you’re growing a remote company, you don’t want to hear that growing a remote company is going to be slower or is going to slow down your growth.

Rob: Yeah. That’s a good example of that. Examples of it I talked about earlier, we looked at some specific things that I think I’ve heard people say over the past, let’s say 15 years of doing this. Common example is, they try a marketing approach, it doesn’t work and then saying, “This never works for anyone ever.” Or, “This can’t work with SaaS.” Or, “This can’t work with B2C.” It’s generalizing a single experience. Even if you try something two to three times, it doesn’t work, it’s not accurate to say it never works.

Paid acquisition is one that a lot of people try and give up on where we see a similar niche or the same vertical making it work. I think content marketing is another one or SEO. You can go on and on with success stories and failures stories. […] to say, “It never or always works.” It’s not helpful to say that.

I think another one I used to hear is never buy an app. You should build all your apps from scratch because the code will be too crappy, there’ll be too much risk, and too many problems. All those things are true that there is problems, and risks, and the code is crappy and all that stuff. But the absolute of always/never isn’t. There are just pros and cons and you have to look at them.

The, “Never hire contractors. Only hire W2 employees.” I think venture capital tends to lean towards that. I’m talking about building up a whole team. Let’s say I’m going to have a team of 20. Some folks might want to be a solopreneur and have 10 contractors or 20 contractors, for that matter. That can work. We see folks doing product-type of services and have it work but it’s a different model. There’s context to it. It’s like a venture capitalist says, “Your employees have to be loyal and your people are what make this company. If you’re going to build it into a $100 million venture-funded business then this is the model we see working and we’re pattern matching, and so they say do that. Similar to venture capitalists tend to want you to have an office versus having a remote team in general. That’s the pattern that they see working. It’s not an always/never thing.

Mike: I think that what’s make it difficult when you don’t necessarily have a lot of familiarity with that topic or that particular subject because you don’t have enough of your own context, so you’re relying on the words of somebody else. Kind of back to what you said, and we’ve reiterated it a couple of times, the words themselves matter. If you’re going to go down the road of trying to give advice or talk about a particular topic in whatever realm you’re doing it, it’s beneficial to most people to provide data points, provide context about what percentages of the time this is accurate. It’s not to say that you’re always going to be accurate.

I think I’ve just answered an email a couple of days ago from somebody asking about Bluetick and how it would integrate in with exchange server. I said, “I don’t know your environment, but the majority of the time,” I forget what percentage I said. It was like 80% or 90%. I was like, “80% or 90% of the time when I’ve see this, this is what it looks like. There are other cases when it looks like this or that. […] of my suspicions based on what you have said but I can’t be 100% accurate.” I distinctly remember saying, “I can’t be 100% accurate because I don’t know.” There’s always those little details that you’re not going to know.

I think it’s important to make sure that you quantify some of those details, so people would know where the dark areas are, so that they’d know where there might be more information or context that they may need to have to completely understand what it is you’re trying to say in the general sense as opposed to making things absolute.

Rob: I like to think of it like this. First, learn the rules. Then, master the rules. Then, learn when and how you should break the rules. When I say rules, I actually mean rules of thumb. A rule makes it sound like it’s an absolute, but rules of thumb that are generally accepted whether it’s common knowledge or whether you ask an expert and they have their own mental model of it. We pointed out Saas KPIs—that was a pretty popular episode a while back—those are just rule of thumbs that we’ve seen in over hundreds and hundreds of businesses.

First, learn those and then learn when they shouldn’t work. If you stop just learning the rules and then deciding you have all these rules and they’re always in ‘nevers’, you’ve stopped before mastery. It’s the same thing of like becoming a black belt in martial arts. Blackbelt is once you’ve learned the basics, then you start mastering it. Then, you become a 2nd, 3rd, 4th level. Black belt, it’s not the end, it’s really the beginning of knowing all the “rules of thumb” or all the tactics and techniques. From there, you then build on that.

Same thing with writing. You’ll see prolific successful writers. Whether it’s a Hemingway or a Stephen King or anyone in the middle, at some point they learn some rules. Then they master them. Then they learn how to break them. They did stuff differently and that’s what makes them great.

Picasso is another one. There’s a Picasso museum. I don’t remember if it’s the one in Barcelona or there’s one in Antibes in France where it shows him in his early years. He just sits and paint for a decade. He paints all the stuff that everyone else is doing. He starts of not good then he gets better and better and better. Eventually, he’s a really good painter. But he’s just one of many. He’s learned the rules and he’s master the rules. Then he started breaking the rules and everyone is like, “What the hell is this guy doing with these crazy paintings?” He invented cubism. That was mastery. He didn’t sit there and say, “A painting should always have this form and that form. This type of shape and that type of shape. He started trying to break those rules and seeing what happened. That’s how I feel about this––the absolute. These rules are helpful for giving us guardrails when you’re early on but at a certain point, you then learn. There’s nuance and pros and cons to them.

Mike: I do wonder whether you get to that certain point and how are you judged afterwards. If you’re trying to break those “rules”, is it because you’re trying to experiment to figure out something new and something that is completely and fundamentally different from everything else? Or you’re just a nutcase? But the results of that is kind of how you’re judged afterwards. He’d done that and created cubism. Nobody liked it or thought everything of it. We would not have ever heard about it right now.

I’m not saying that that’s bad and you should experiment. I’m just pointing out that, I think that is a natural evolution of what that process looks like. It may not turn into anything but that doesn’t mean you should experiment with it.

Rob: Right. That’s the thing. I think the bottomline is it’s important to form an opinion. It’s important that we’ll be able to discuss our opinions, be opened to being convinced otherwise by smart people who have different experiences, seeing the nuance and things. That’s the bottomline. Again, I come back to someone like the folks who I respect and who I see who are a, successful, and also, have good relationships with fellow humans whether it’s a spouse, or children, they have good family life, they have friends. They’re just people I want to be more like. Jason Cohen, Hiten Shah, we have dozens and dozens of folks that we know that do this. They are the folks who I see embodying this thinking, who learned the rules, that mastered the rules, and then learned when and where to break them. It’s very, very rare you’ll hear any of them say that, “It’s this hard and fast always/never.”

I really like Jason Cohen’s recent post on, it’s called Kung-fu. It was all about his rules; his rules of thumb. He said, “Look, everyone’s different. Your mileage may vary. But these are things that I’ve learned.” There were things like, it wasn’t, “Don’t do freemium.” It was, “I don’t like freemium. I’m not going to use it and here’s why.” I think that is super important to kind of couch something like that. It really comes back to flexibility and nuance.

Even a growth mindset versus a fixed mindset. I’ve talked about that book Mindset by Carol Dweck. Growth mindset believes you can and should change overtime. Even your opinions and some of your beliefs can be malleable. That’s helpful and leads to success in a lot of things.

Mike: I think overarching point here is just to educate yourself. Not just about the things you’re working on but about how other businesses in general work. Because I think it gives you more of a mental model or a framework to work from and be able to be a little bit more objective about the things you’re looking at. It seems like it would be easier in some ways to be more ignorant and just say, “I know what I’m doing. I’m going to do things in this particular way because I know that it is going to work.”

I think being able to second guess yourself and being able to be a little bit more objective about the decisions that you make, or that other people are making, the advice you’re receiving from people, is extremely beneficial just because it gives you enough mental model to work from something where you’re not sure. You’ve got these dark spots and you’re aware of those dark spots. You know that there’s places where there’s some—I don’t want to call it risk—but some percentages that could go either way. At least knowing where those places are is important.

Rob: Yeah. When I’m thinking about a decision or something like this where I might have an absolute in my head, I often will couch it as like, “Well, I’m 51/49 on this.” Or I’ll say, “I’m 95/5 on this.” I rarely go higher than 95. There tends to be the exception or the doubt. It’s not just so clear cut.

Before you take us out, Mike, there’s a few absolutes that I want to throw out that as you listen to them, each of them has totally valid exceptions even though they feel like, “Wow, maybe it should be true.” I challenge the listener to think about the complete valid sections to each of these things.

Always write unit test when coding. Always grandfather on price increases. Never trust Google or Facebook. Never build on someone else’s platform and have your business totally reliant on it. Never go B2C. Never raise funding. There are more we could throw out.

In general, are those things true? Yeah, I would say so. Yeah, I think those are good rules of thumb. Are there totally valid times to break them? Indeed, sir. Absolute thinking, while it’s not always bad, we would conjecture that, I think all of us, you and I included, I think we can all get better at.

Mike: You would say that it’s not always bad but it’s not always good?

Rob: Not always good. Let’s raise the bar. Let’s raise the bar of the conversation. I think that’s the point.

Mike: With that, we’ll wrap things up. If you have a question for us, you can call it in to our voicemail number of 1-888-801-9690 or you can email it to us at

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