In this episode of Startups For The Rest Of Us, Rob and Mike ask the question: should you love what you’re working on? The guys talk about this topic in the idea of balancing interests and opportunity. They also ask themselves the question and how it pertains to their lives and businesses.
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Rob: In this episode of Startups For The Rest Of Us, Mike and I talk about whether you should love what you’re working on. This is Startups For The Rest Of Us episode 403.
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 built your first product or just thinking about it. I’m Rob.
Mike: And I’m Mike.
Rob: And we’re here to share our experiences to help you avoid the same mistakes we’ve made. Where this week, sir?
Mike: I started a local D&D meetup group.
Rob: That is so cool.
Mike: A friend of mine and I’ve played with our kids. I’ve got two sons and he has a son and two daughters. One of his daughters played a little bit with us. She was like, “Yeah, this isn’t for me. I hate this. I don’t want to deal with boys.” I think that’s certainly what is was. But the other three, him, and I play. We wanted to start up a group where we’re actually playing with adults because kids can be a little bit difficult to keep on track sometimes.
He knew a couple of people then I started a meetup.com group to try and find at least one more player. There’s five of us now and we’ve met for the first time earlier this week. Started up a game, we expect it to go for a couple of months, we’ll just meet up every week, and see how things go.
Rob: That’s fun. Did you say you just meetup.com?
Rob: Awesome and you’re playing fifth edition?
Mike: Yeah, the latest version. I think two or three other people who we’re playing with haven’t played in 20 or 30 years. Then they went to college, had kids, and got out of bit for a while. Now they’re coming back and so far it’s been good. We only had one session, which was about three hours long, but we spent some time before that at a different time creating characters. It’s good so far.
Rob: Were they marveling at the ascending armor classes and there’s no THAC0. I don’t know if you played second edition, but did they have to read the player’s handbook or you just brought them up to speed verbally?
Mike: Yeah, I caught them up to speed. I was like, “Here’s the differences from when,” because I asked them which versions they played. So up to second edition they have the THAC0 and then in the third edition they switched over to the d20. I just explained those things.
Then one person, he still plays a lot of version 3.5. He’s never played 4 or 5 before. I looked it up and found a place—I think it’s Reddit—where they basically laid out, “Hey, here are the differences between version 3.5 and version 5.
Rob: There’s a lot more similarities than I thought. I know 5 is more stripped down. There’s less feats and there’s a bunch of stuff there. The prestige classes I think are maybe those are only in 4. I never played 3.5 or 4, but I’m pretty familiar with them at this point.
I know there’s always controversy around it, but I played basic, I played expert, then I played first edition. Then I just got familiar with second edition, which is where they introduced THAC0. Pretty sure first edition it was all table-based, is my memory, and then stopped, got into sports, music, and stuff, and then just came back into it as my son got old enough to play.
I remember my nostalgia is for basically probably first edition, maybe basic but the rules are so jenky there that I couldn’t go back to it, but I remember Googling, I’m coming back to D&D. Should I try fifth edition or should I go back to first edition?
There’s all these discussions about it and the general consensus was, especially for bringing new players who’ve never played anything before, bring them to fifth edition. It’s a pretty nice rule set. It’s honed and refined. It’s like a piece of software that’s gotten better. I think there was bloat, perhaps.
People could argue as you got 3.5 and 4. Mostly 4, I think people had some issues with, but then 5 was almost like a partial rewrite or something, or someone refactored a lot of code, added some unit test. It’s a terrible analogy, I don’t want to get into this, but I really get them. When I dove into 5, I was like, “This is a really fun game to play.” It’s so much less about the mechanics of the game, which was my memory of the first edition. All these tables I was looking up and all that stuff. It’s so much less about that. It’s more about getting into the characters, the combat, the adventure, and the fun of it. It was cool. I taught my son I think when he was seven or eight, and he picked up the mechanics pretty quickly.
Mike: I really liked what they did with the fifth edition as well. It’s just so much more streamlined and it’s simpler without being simplistic. That’s probably the best way I would describe it. And you’re right. There’s a lot less reliance on tables and the one thing that I really liked that I’ve read about, which is the difference between 3.5 and 5 is that in older editions, there was a lot of reliance on stacking things to get more powerful.
You’d stack your armor and various other things. In this, you don’t have really have to do that and for the most part it’s just like, “Oh, you have advantage and you get to roll 220 set of die and take the best one.” That’s great except when, as an example I was explaining to these guys like, “Hey, this is what it looks like,” and I rolled 220 and I rolled a one and a two.
Rob: For us, we’re recording a little bit in advance but if all goes well, we have closed on our new house in Minneapolis and frankly, all of our stuff will have been moved because the move is scheduled for just a couple of days after. We’ll be in the process of unpacking boxes and probably hanging things on walls. I’m really looking forward to having that process, the chaos ending because already, I’m sitting at our old house and there’s things off the walls and there’s a few things in boxes.
Everyone is a little bit disjointed. You get that feeling of like, “We’re in process, where was that one thing, I can’t find it,” or it’s even just a visual cue. There’s just some chaos around me and there’s this unsettled feeling I feel like with every family member being in a place that feels like our house but it’s a little different because there’s nothing on the walls as an example. I’m looking forward to feeling better about that.
Mike: Like an Airbnb where everybody moved out and you just walked in.
Rob: Yeah but even worse than that is, it’s our house that’s familiar. Everything’s packed up and stuff. It will be good, but it’s definitely move up for us in terms of the house is bigger and nicer, and we can do things. I’m already looking at what smart home things I’m going to install because we have several Amazon Echos and there’s all the controlling you can do.
Even starting simple stuff like light switches and getting more advanced with security stuff, operating garage door openers, and that stuff. So I’m kind of nerding out on that a little bit. Something I haven’t able to do because all that stuff, I’m not going to invest time in that in a rental, and it really hasn’t come big time into fruition. It’s been a couple of years since I’ve owned a house now, so I’m excited at the potential of geeking out with some of that.
Rob: Now that sucks.
Anyway, just because there was the race condition, like it worked fine for just about everybody and then there were, I think, it either certain browser combinations, or I couldn’t even nail it down to, say it was just this operating system and this particular situation. If the latency tended to be high enough, then it tended to not work.
Mike: In this case, I went down the path of looking. In Chrome, there’s this ability to say, “Oh, use a different emulator if this was running on a 3G connection or something like that, or even slower.” Even though I still could not replicate it, I’m pretty sure that it had to do with certain types of browser combinations and what other plugins you have loaded. Based on those things, it would either trigger the race condition or it wouldn’t. Sometimes it would work. Actually, the vast, vast majority of the time, it would work fine and then just these little occasions where certain things would be screwed up and it just wouldn’t.
Rob: So cool. Today, we’re going to kind of, I don’t know if it’s a thought experiment as much as it’s a discussion of this topic that come up now and again. I’ll say, not even an inflection point but at a point where I’m thinking about, “Hey, what could happen next for me? What’s going to come next?” I know there are a lot of people are thinking at a given time length, “Hey, what project am I going to work on?” and, “What type of niche should I go after?”
There’s always this balance between balancing your interest in something and the opportunity that it has. I think the question we want to explore today is, do you need to love what it is you’re working on and what that looks like? You can take a business that sells beach towels online, and you could say, “Well, beach towels are awesome and I’m really into them and I collect them and I’m super interested in it.” Or you could say, “Well, I’m not interested in beach towels, but I am interested in ecommerce and ecommerce really excites me.” So you have that interest. Or you could say, “Well, I’m not that interested in ecommerce but I am interested in just running a business, and this is one that I can do in my spare time.” So you have interest there, or it’s kind of a continuum. Or further up, you could say, “I’m not even interested in running a business, but I just want the freedom that it provides.”
One of those four places on the continuum I think is what we’re going to look at today and balancing on one end, there is interest and then on the other end of that spectrum, there’s opportunity. I think potentially if you can get them to overlap, maybe it’s less about two ends of a spectrum and more about, it’s a Venn diagram where you have circles. The circle could be, these are all my interests and that includes role-playing games and it includes stock market investing and it includes Legos and I don’t know, other things that someone might like. Running a business might also be one of those.
An opportunity could be things that overlap with those, like, “Hey, there’s a real good opportunity starting at Lego RPG site that no one’s done and you can make much money at it.” That’s not true because you probably wouldn’t make any money. I know there’s a bunch of opportunities like selling dog food online or starting a business you have no interest in and you got to figure out and evaluate for yourself which of these are you going to go after? How are you going to balance those, I think is a better way to put it.
Mike: You mentioned Venn diagram in there. I think the one misleading thing about using the phrase Venn diagram is most people think of it as this mechanism for overlapping either two or three things, but when you start adding more than three things in, it’s almost like more of a three-dimensional model at that point. It’s still a Venn diagram, but it’s just really much more difficult to visualize because some of those things just don’t overlap at all or they only overlap with everything but it’s also difficult to put them in if it’s actually like a 3D model.
Rob: I think that’s a good point and a Venn diagram or a continuum, a single line, an axis was one thing on one end and one thing on another. These are just really abstractions. It’s ways that we can describe things and at certain points abstractions always break down. I think that is something to keep in mind as we talk this through.
There’s a lot of folks and there’s a lot of conversations that I’ve seen around this idea of should you follow your passion or should you just go after the opportunity. People try to make it binary and they say, “Well, if you just follow your passion, you’ll get there.” Or you purely have to go after opportunity and I believe the conclusion that we’re probably going to get to is that it’s a blend of those. It’s figuring out what you can be passionate or interested in, but also blend out with something that held some opportunity.
To start to think about it, there’s this question that I want to throw out, what drives you? You can answer that in the abstract or you can take a personality test. Have you ever taken the enneagram?
Mike: I don’t think I have, no.
Rob: We’ll link it up in the show notes. You can take it for free online and it’s like the, what is it the Myers-Briggs where psychologists like Sherry says, “You know there’s some value there, but it’s really not scientifically a research.” Perhaps as a psychologist, I would take it with a grain of salt versus a true psychologist-administered test. But there is still some value to these things. I even think StrengthsFinder 2.0 I think is good. It gave me some insight and a little more insight into who I am even if that’s not the most academically rigorous test of anyone.
The reason I bring up the enneagram is you basically take this test online. I think it takes about 20 minutes and then it gives you a couple of numbers, it’s one through nine, and each number corresponds to a personality type. Number three is an example, a lot of folks that I have met in business wind up with this and this is the achiever. There’s always pros and cons and it says the success-oriented pragmatic type, adaptive, excelling, driven, and image-conscious.
I think some startup founders are driven by the achievement. They just want to achieve whether they’re trying to fight this voice in their head. It’s the voice of their father, or the voice of someone who told them they can never succeed, or maybe it’s just a drive they have to make money, maybe it’s just a drive to show everyone or show themselves that they can do it.
But there’s something about just doing it for the achievement’s sake. They don’t necessarily, in my experience, care about the process of getting there, about what they create along the way, or about they could achieve in a business that sells cell phones, or is a GPS startup, or is selling whatever, beach towels online, but if they built an eight-figure business in any of those, they would feel they have achieved something and they’d be happy.
Versus, I believe it’s number six, and I think that’s me. It’s the loyalist. It says the committed, security-oriented type, engaging, responsive, anxious, and suspicious. A big part of the loyalist, when you read through the description is, there’s this sense of creating and needing to create something, put it into the world, to own this creation, to advance it, and to make it interesting.
What was funny is interacting with some folks once Drip was acquired, interacting at leadpages. Several of us took this test and it was pretty obvious there were folks who, it didn’t matter to them what business we were in. They just wanted to go big. Going big for the sake of going big was awesome to them.
For me, it was like, “No, I’m actually here to build stuff.” I’m a banker and I am the guy who writes books, I’m the guy who creates podcast, and create software, and builds interesting things, and hopefully, that’s why I want the money is so that is can go work on these interesting things. It’s to have the freedom to go do interesting things. Not just achieving for the sake of achievement.
Mike: You definitely fit that loyalist. You’re definitely a suspicious and shady-looking guy.
Rob: Hey it is, huh? That’s the thing. When you read any of these, there’s always some negative and it’s like, “Oh, am I really?” And it’s like, “Yeah, I probably am.” I’m probably am all those things. But engaging and responsible certainly fits as well.
The reason I bring the enneagram up is that you can take any number of test, but it’s interesting to spend 20 minutes and get some insight, to read the descriptions and think, “Am I here to achieve?” Because if you are, then your need to love the business or the specific niche, or whatever it is that you’re working on, is probably going to be a lot less than someone who needs to love what it is that they’re working on, and to be enthusiastic about it.
Number seven is an enthusiast. There’s others of these numbers that really point more towards like, “Yeah, you need to love what you do or else you’re going to bail on it.” I think it’s interesting whether you take this or you just think about it to yourself. Certain people know that there’s no chance that they’re not going to be happy working on something that they’re not super interested in everyday.
Mike: I think in general when you take a look at these types of personality tests or things that will help to describe or categorize you, it’s easy to write-off the 20 minutes that it takes to do any one of these and as you said, I think that if it’s not something that it is rigorously given or tested, like if it’s a 15 or 20-minute test, it’s not going to be rigorous.
If you spent an hour answering questions and you’re answering 60, 100, 200 questions or something like that, it’s a little bit more. Those you probably have to take with less of a grain of salt, but regardless which one you take, I think you’re better served by looking at the results of it as in how far you skew in a particular direction, regardless of what direction that actually is.
As you said, every single one of these has pros and cons associated with it. People who exhibit different traits are going to have different interests and they’re going to dislike different things. But when you’re going through those, it’s important to not just take a cursory look at those, like the different personalities or different categories that they could potentially lump you in, and then not even take the test, because taking the test itself is going to tell you how far you skew in one direction or the other.
I can look through these nine or right here for the enneagram and I can probably say, “Oh, well I associate with four or five of them, or even six or seven,” but it doesn’t tell you how strongly you associate with them, and that is even more important than being able to put yourself in one of those categories.
Rob: Yeah, I would agree and I didn’t mean to downplay this from the start. When I say I take it with a grain of salt, I mean, don’t base every life choice on your enneagram result. The enneagram is given to tens of thousands, hundreds of thousands of people. It is research-based and it is like a viable test. But as you said, when it’s only asking so many questions and it’s 20 minutes, there is less rigor there than a test that is. A lot of the psychological battery tests that are given, you’ll sit there for two, three hours for them to get a full picture of stuff. It’s just a nice taste and a nice direction.
I do think I like these things because I always learn something about myself and it’s typically something that’s a little bit of a blind side for me. Typically, I’m like, “Yup. That’s me, that’s me, that’s me,” and then they’ll throw something else in this, it’s like, “Oh, that’s true, but I hadn’t realize that.” It’s one, the anxious or suspicious thing. It’s like, “Yeah, that’s a good point.” I do tend to not trust people until I known them for a while and how is that a plus for me and how is that something that maybe I need to work around.
But I think the interesting thing and a question that’s framed is like, “Are you the type of person who can work on things that they don’t love?” That maybe the question to ask yourself. Certain people just doesn’t know this. I remember Jason Roberts on TechZing used to always say, “I know I’ve got to love it or I’m just not going to do it.” He’s very much a passion player. He would only start ideas that were super exciting to him and he could never go into a niche that was selling beach towels or he would have completely peered out.
Whereas for me, my goal of financial independence was more important to me than needing to love that I was selling the duck boat plans and the bonsai tree ebook, in the early days, the beach towels and stuff. Those are high probability of success things for me based on my tool belt and I was able to build those collectively into six-figure income and replace everything. I bought my own freedom. Then I moved more into things that I enjoyed. That’s when I started doing HitTail, and Drip, and even during that time I was seen doing MicroConf and this podcast. The stuff was part of that.
Again, I hope it’s a spectrum or if it’s a line or whatever, but I always think about this one example of, to optimize for opportunity, you could sell coffins online. To optimize for interest, if you love watching movies, you could review movies online, or if you role-playing games, you could review role-playing games online. Those two are massively in tension. The role playing games and the movie reviews is going to be so hard to make a full-time living at that. Yes, there’s a handful of people who do it, but it’s really, really hard and it’s a ton of work.
Compared to selling something that’s really boring like accounting software or coffins online. I see it partially as a joke, but I remember a venture capitalist using this an example of them wanting founders who are really into what they’re doing. This venture capitalist said, “You know during the dot com boom when everything was going online pets.com, grocery delivery and all that, there were entrepreneurs who were pitching them like a really inefficient market is the coffin market.” It’s a cottage industry, the markup is outrageous, people don’t haggle, it’s just this weird time. The guy was like, “There’s a huge opportunity here and we can make a ton of money and save money for consumers.”
I believe that mattresses are like this, too. Mattresses, the markup is always huge and then Casper has come along and I really think there’s ton of opportunity there. The VC said, “I kept asking the guys, ‘Why do you want to do this coffin startup? A funeral startup?’” They’re like, “Well, because there’s opportunity there.” The VC didn’t fund them because he believes that you need to really be into the whole space, love the space, and this and that. That’s fine. That’s his belief. That’s his thesis of funding people.
But I think when you ask yourself, you can have the continuum. You may not love mattresses or care anything about them, but if you’re really interested in building a big business, running Casper would probably be an interesting slush fund thing for you to do if you’re an achiever. If you just want to achieve, you can build that eight, nine-figure business, and really not care much about the product you sell.
Mike: I can think of any number of businesses that I would think it would be interesting to start and go for but that doesn’t necessarily mean that there’s a business opportunity there as well. I think that’s what always bugged me about the do-what-you-love advice. Just because you love it doesn’t mean it can actually make a business. That advice kind of glosses over the fact there may just not be a business there for it. I don’t know. I think there is a difference between doing it because you love it versus doing it because you want to, also making an income from it.
That goes back to the Venn diagrams that you’re talking about. There has to be a clear intersection of multiple things in order for it to work for you based on whatever your goal is. If you just want to do it to have fun, go for it. You don’t also have to make money. But if the Venn diagram includes making a full-time living from it, then the business opportunity has to support that. If it doesn’t, then it’s not going to work.
Rob: Right and some luck if few get to do both. Gary Vaynerchuk loved wine and he turned that into a business. It does happen. It’s just how many other people try to do the exact same thing and it didn’t work versus if there really is opportunity there that the odds of you, even getting a base hit and I think that’s the thing, it’s like are you willing to have a higher chance of success but perhaps enjoy things a little less along the way because you’re not doing everything that you love. Maybe you’re just going for that single or that double, but if it brings you financial freedom that you can then work on stuff you love later, but you’ve got to do a few years of not terrible drudgery. It’s not like you’re working on 9-5 for someone else, but it’s weighing those two things.
I think that leads me to a question of, “Tell me what do you love about Bluetick? Do you love the idea of warm outbound email? Or is it you love building software and want to find a way to make money from it and sustain yourself full time? Is it you love building businesses?” There’s got to be something in there that drives you day to day but I don’t get the feeling that you woke up two years ago and said, “Oh man, all I want to think all the time is email deliverability and how to hook into the Gmail API.”
Mike: Yeah, I definitely did not think of that and of course I don’t hook into the Gmail API because it doesn’t work very well. I think the thing I keep coming back to is that it actually solves a genuine business problem, first of all, and second, I like the people that I work with. Like the customers that come to me and they’re like, “Oh I have this problem and I need to be able to fix it.”
I’ve taken various personality tests in the past and one of the things that tends to come out at or very close to the top of the list almost every time is that I’m a people person. I care very deeply about a much smaller number of relationships, but people is a main focus for me. If I were to sell a business for $20 million and I was the sole stockholder, for example, I wouldn’t just keep it all. My inclination would be to share that the people who have helped get me there.
There’s certainly people who would take the opposite approach and say, “Well, I took all the risk, I did everything, I own 100% of it so I should get everything.” There’s nothing inherently wrong with that, it’s just not my personality.
There’s that side of it that I like helping other people, which partly why I do the podcast, partly why we’ve run Founder Café together and why we run MicroConf. That’s important to me and running Bluetick, I get to work hand-in-hand with a lot of different people and a lot of different businesses, and yes, it ultimately benefits me financially as well, but at the same time I know that deep down I’m actually solving a problem for them and it does help their business.
Rob: I think that’s an important thing to know. You look around at different examples. Think of Dan and Ian with Tropical MBA. I’m pretty sure they weren’t that excited about cat furniture and valet podiums, but they were excited about the prospect of freedom, about the prospect of starting your own business. Ian’s certainly a maker. He’s the designer of the stuff in the early days, and I think they’re excited just about building businesses and such. That’s that balance of they’re excited about enough things about those spaces and they saw tremendous opportunity there that they’re willing to dive in.
I felt the same way about HitTail and Drip. I have always liked SEO, I’ve done a lot of it, and I’ve always done a lot of email marketing, and use many ESPs. But I’m not as passionate about those things as I am, say, some of the hobbies that I do, such as playing guitar, or playing tabletop games, or even personal financing, and stock investing. Those hobby things are just so much harder to turn to real businesses. I kind of combined that opportunity with SEO and email marketing with the interest that I have in those topics, and then build businesses out of them.
I think that that’s probably the conclusion that I leave folks with. You may not be super excited about being on online classified ads, or about selling beach towels, or whatever. But there are other things that you can do and it’s about knowing yourself. You have Jason Roberts, again, coming back to him or someone like him. There are people out there who are just really need to love what they’re working on.
A lot of those folks become indie game developers or they build software for guitar effects. I used to work with a guy who built that on the side because he was so into the music, and that’s all he wanted to do is be around music and that’s cool. But for him, if ever he achieves financial freedom, it’s going to take decades and it’s just a lot more risk there, and a lot less chance of success because you’re stacking the cards against you in exchange for being able to be really passionate about what it is you’re working on. That’s the trade-off that you will have to make.
I think each of us as individuals has to think through that and think about how much it is you desire to work on something you love versus perhaps having more of a chance of that success.
Mike: I’m wondering how much of the decisions that people who are listening to this podcast make or just entrepreneurs in general, I wonder how much of those decisions are influenced more by what they see as a potential business opportunity versus what their interest are because I talked to a lot of people, like, “Oh, I need an idea for my app. I don’t have any ideas.” That’s a very common thing that people will say and most of the time I think it’s because they don’t want to build something that somebody else has built or build a business that is very much like another business.
But at the same time, those things can be very successful and if you have your own take on it, your own ideas about how to take that to fruition, then you can certainly make it work. But if they just don’t have those ideas or they think that they don’t have those ideas, then they’re not going to move forward with them.
Rob: Right, and if you work on a business you hate every day, then obviously, that’s not a good solution either. Honestly, when I look, I think there’s a lot of approaches. We’ve gone through them here. The approach I took was in the early days my interest was financial freedom. I just kind of slogged it away, a bunch of businesses that I didn’t have a ton of interest in, but I was learning and learning is exciting to me. I think a lot of folks in our audience probably feel the same way. Just the act of learning new things could potentially keep their interest. Then as I built more and more of those up, then I was able to go into things that I was more interested in like, let’s say HitTail and Drip, with SEO and email.
Now, I’m at the point where I have the luxury of more time to invest in something I’m working on and it doesn’t need to be that big hit. I may even sway further into, “I’m only going to do stuff that I really, really enjoy.” Maybe it is. Maybe my next thing is nothing like anything I’ve done in the past and it’s truly like, I mentioned it a little bit, “I’m going to build an authority website in this topic that I just think is super interesting, and see what happens.” Maybe I’ll spend two years on it and I enjoy it because it’s a hobby and it never does anything. So what?
Personally, I would have hated doing that 10 years ago because I would have been hating my day job while I did this and I didn’t want to have that pole. I wanted to achieve that freedom first. I do think that there can be steps along the way of shifting and that it’s not this one-size-fits-all or even this permanent approach for each individual.
Mike: I think that’s all an interesting thought experiment. If you have any thoughts of your own, just feel free to head over to the website at startupsfortherestofus.com. Leave a couple of your thoughts in your comments. With that, we leave you for today. If you have a question for us, you can call it in to our voicemail number at 1-888-801-9690 or you can email it to us at questions@ startupsfortherestofus.com.
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