Joel Runyon (@joelrunyon) didn't start out with a whole lot. He couldn't get a job. He had no business skills. He didn't know how to code. In fact, all he had was long list of things he thought he couldn't do. In this episode, Joel talks about how he was able to pull himself up by the bootstraps and create multiple successful businesses by doing the things he was most interested in, being persistent and doubling down on the things that stuck, and literally attempting to accomplish the impossible.
What’s up, everyone? This is Courtland Allen from IndieHackers.com and you’re listening to the Indie Hackers Podcast. On this show I talk to the founders of profitable internet businesses and I try to get a sense of who they are, what makes them tick, how they got to where they are today, and how they make decisions at their companies.
The goal here is so that the rest of us can learn from their example and go on to build our own successful internet businesses. If you are a founder or you’re thinking about starting a company, I highly recommend that you check out IndieHackers.com. It’s the website behind this podcast, and it is full of other founders swapping tips with each other, giving each other advice and feedback and ideas, and in general just helping each other build successful companies. You can also find full transcripts of every podcast episode, including this one.
I am super excited about today’s guest. I am talking to none other than Joel Runyon. Joel, welcome to the show. It’s great to have you on.
Thanks for having me, man.
You’re someone who’s difficult to introduce because you do so many different things. I mean, you are an Indie Hacker, you got numerous businesses that you run, you’re a blogger, you’re a podcast host, you are ultramarathoner and somewhat of a fitness and nutrition guru, you’re a marketer, you’re an SEO and growth consultant. So I don’t even know where to start.
I like to say that I run businesses and marathons. That’s a good introduction, especially for the last two years, I would say. I have two main businesses. I have a business called IMPOSSIBLE, which is a mindset and fitness business, and then I have another paleo-nutrition company around the paleo diet and meal planning and several different apps and other things like that. And then on occasion, I do consulting for various funded startups on a one-off basis to kind of keep myself sharp, keep me interested in other people’s businesses and just kind of what’s going on.
And then sometimes it’s fun to work with the – I do a lot of – all of my own stuff is bootstrapped, but it’s fun to work with funded companies in a different way, because a lot of times you can make a few small tweaks here and there. And because they’re much bigger operations, you can see some massive results.
So yeah, I like to say I run businesses and I run marathons, and I try to find the intersection where business meets adventure and have a lot of fun doing both.
What is that intersection? How does business overlap with adventure?
That’s a good --
I’m hitting you with the abstract questions right off the bat. (Laughter.)
That’s a good question. It’s good. I think the best way to share that is to kind of tell how my story started. And basically, I started a blog in 2010 about nine months after I graduated from college. And I couldn’t get a job out of college, so I did all the things you were supposed to do. I had a great GPA, did a couple different sports, did a lot of travel, learned Spanish, all those things. Got out of school in 2009 right in the middle of the recession, and couldn’t get a job. There were no jobs.
So I was doing this path that you’re supposed to do and kind of got to the end of that path and realized, “Okay, this apparently doesn’t work anymore.” And so the short version of that story is I sat around for a long time feeling bad for myself, got a bad job at UPS delivering packages in the winter in Chicago, turned down by places like Starbucks and Target after getting my college degree and all this other stuff.
And so end up nine months after school laid off my part-time job at UPS because it was seasonal work and they needed to get rid of – they only hired workers for a couple months at the time during Christmas. And kind of sat around looking at my life and saying, “Is this kind of what we have to show for where we’re at right now?”
And I was reading some of these other blogs on the internet. Chris Guillebeau was a writer I was following along. He was traveling to every country in the world. I had another friend that had quit his job and moved to Thailand.
And I saw all these people doing all these interesting things. And I wanted to something like that, but I couldn’t even get a job at Starbucks. I couldn’t keep a job at UPS for more than two months because the economy was so bad they didn’t have any packages being sent out, so they didn’t need all the people they were hiring.
And so I kind of had this list of things that I wanted to do, but they all seemed impossible to me. And I felt bad for a long time and didn’t want to actually try and go out and do them. And then I realized after a little bit that no matter – I’ve got nothing else going on right now, I don’t have a lot of things holding me back, I don’t have a lot of money, I don’t have a lot of resources or connections.
But one of the things on my list was run a triathlon. And I didn’t know how to do it. I didn’t know what went into it, but I decided I can at least – I have no excuses for not putting my shoes on and running around the block, and I have no excuses for not getting on a bike and riding around the block. And so I did that.
And when I finished that race, there was a specific thing that I remember thinking was, “I finished this indoor triathlon.” It was a really basic, small race. And I remember finishing that and thinking to myself, “You spent so much time telling yourself that this was impossible. What other things are out there that you think are impossible but you could do if you just trained for it, if you just went for it?”
And so that was kind of the start of my IMPOSSIBLE business, and kind of how it’s partly a business, but it’s partly how I kind of changed my perspective on my own life. And a lot of times, my ideas for business, my different projects that come up, end up coming out of me having something on this list that I think is not only fun or interesting or maybe adventurous, but that I try to figure out a way to turn that – turning it into something that I can actually build a business and build a life around instead of just trying to find spare time outside my 9:00 to 5:00 job, if that makes any sense.
So that’s a long story, but people who aren’t familiar with me, maybe that gives a little bit of background on who I am and how I got started.
And then this list that it started was sort of the impetus for me to not only try new things, but try to do interesting things with my life. And then every once in a while, I’ll find one of those interesting things resonates with other people. And then you kind of just start digging a little bit more, and sometimes you find different business opportunities therein.
I really like what you said about how you thought it would be impossible to run this triathlon. And then after you trained for it and did it, it sort of unlocked a door almost in your mind where you’re like, “Well, I can apply the same regimen and the same process to other things that I probably thought were impossible and just work towards getting them done,” whether that’s finding a job, starting a business, or whatever else is on your list.
And I think it’s kind of this idea of just baby steps, where every single time you take a step, you get a little bit more confident for the next because you can look back. And you’re slowly but surely building up this resume or this list of accomplishments that you’ve done.
It reminds me kind of when I learned how to code in college. I had never really done what I would call real programming. I had always just done design work and HTML and CSS, but nothing substantial. And then I had a friend. He was like, “Let’s just build this thing. “And I did just a crappy job not knowing what I was doing. And then having done that, it made it so much easier for me to take the next step.
So I think that’s a pretty cool way to get started on your journey. And I hope people listening in who want to start a business and haven’t started will find some sort of baby step they can take that maybe seems hard but is still doable.
One of the things I talk about, especially with the fitness and the mindset aspect, is a lot of times people with businesses and other things in their life, but I’ll talk about business right now, they’ll get stuck in a certain spot because they’re living in their head all the time. And the thing I like about fitness and some of the different physical challenges that I’ve done is they actually force you to move beyond what you think you can do.
Then you get reference points for other parts of your life where you say, “I was at mile 40 of that race, and I couldn’t figure out how I was going to get another 20 more miles.” And then you have this sense of despair or, “How am I ever going to finish this thing?” And that’s a very physical, real sense. Your body hurts, you’re aching, muscles you didn’t know you had are hurting all over the place. And you have to figure out if you’re going to go home or if you’re going to figure out a way through it.
And once you do it, it’s easy to spot that same mindset in other parts of your life when it’s business or if you’re coming up against really tough business situations, whether they’re financial, legal, whatever. You’re like, “How am I going to get through this?” You can take that same mindset that you’ve built up through these different physical challenges and apply it into business. And that has been one of the most helpful things for me throughout anything that I’ve done.
So I find that’s super helpful, just giving you another reference point and another area of life that you can sort of just kind of pluck out of that situation and apply in another.
Reference points; that’s a great way to put it.
So you mentioned this list, your Impossible List, which I think is a cool place to kind of start talking from. Because as I mentioned earlier, you’re doing a ton of different things, and your Impossible List kind of ties everything together. So why don’t you tell us about that? What is an Impossible List, and why did you create one?
Yeah, the Impossible List is – a lot of people see it and they think, “Okay, it’s like a bucket list.” But there’s a couple differentiations that I’ve made. One, with “bucket list,” most people think, “A bucket list, okay. I’m going to get real excited about it, I’m going to make my bucket list, and then hopefully I can do all these things before I kick the bucket or whatever. And so maybe I’ll get some of these things done.”
And they get really excited about doing it, but a lot of people have bucket lists and maybe – I find a lot of people make bucket lists, but not a lot of people actually knock things off of it. So that’s one.
And the other thing is that the Impossible List for me started really small. It started with an indoor triathlon in the west suburbs of Chicago. So it wasn’t like, “Oh, I’m going to run a” – I didn’t start off, “I’m going to run an ultramarathon on every continent in the world and I’m going to figure out how to do it.”
It started off with, “Okay, what do I think is really impossible?” And for me, running a triathlon – it sounds stupid now, but I didn’t know anybody who had run a triathlon. I didn’t know anything about that world. And I didn’t look at myself as a triathlete. I had never run more than a 5k before I signed up for that thing.
So the kind of two defining things of that are, one, you’re continually making it. So you start small and then you continually add to it. So once I did that small, indoor triathlon, I kind of conceptualized it as, “Okay, I pushed past that limit of what I thought was possible. Now, what else is past there?”
And the interesting thing about stair stepping it like that is sometimes you’ll take a step in one direction, and you find you’re not really into it. You’re like, “Okay, that was fun to try, but I don’t really care about it.” And sometimes you’ll take a step in that direction and find there’s a lot more there, and you can kind of keep digging.
So where did you end up going from there?
I got involved in endurance racing and all sorts of stuff like that where I kind of started scratching the triathlon itch, got into triathlons, kind of tricked myself into becoming a runner, and then found the world of ultramarathons and all of that stuff and started getting into ultras.
And I’ve got two or three concurrent timelines that you want to kind of think about it as. And so there’s what I was doing with my fitness life. And then once I started – I was saying that when I started my blog and my Impossible List, I couldn’t get a job anywhere. And so I did this thing. I think some people have called it “apprenticeships.” I’ve called it basically working for free. But right around that time that I did the indoor triathlon, I started a quote/unquote “apprenticeship” or working for free, where I got paid a very, very small amount of money to work side by side with an owner at a marketing agency, and was able to learn a bunch of skills kind of on the job even when I didn’t really have anything to offer in that space.
And then over the next three to six months, basically, free worked my way into a job there and had that for two years, where I ended up working my way up to a marketing director and ended up – I worked my way up, I got recruited to another firm, started working on much larger, national accounts. Camping World was one of my clients, doing some stuff for Marcus Lemonis, who runs The Profit. So I was managing ad spend for his campaigns around that time.
All while I was doing that, I was trying to get faster and go farther with my racing, and then also working on some side projects and impossible as well. And so --
That’s a lot of stuff.
Yeah. So there’s a few different things going on. But what’s happening was each time I found that I pushed myself past a limit in one of the areas, I was able to take that and kind of apply it in another area. So once I figured out, “Oh, I could not just get a job but now there’s other companies out there kind of competing for me,” I was able to take that and kind of apply it into my fitness and my racing. And then I was able to take, “Okay, I have some confidence in my skills and everything I’m doing at my job. So what if I started freelancing here?”
And that’s kind of how the self-improvement stuff started turning into actual business things, where I was looking, “Okay, maybe there’s something here that people would want to pay for or something that I could do on the side of my day job that is actually valuable to people.”
It’s cool looking at your Impossible List. For anyone listening, you can just Google “Joel Runyon, Impossible List” and it’ll come up. But it’s kind of like this spreadsheet. It’s in Airtable, which is a great app, and you’ve got it divided into all of these different segments of life. So you’ve got fitness, travel, minimalism, renaissance man is a category on here, languages that you want to learn, entrepreneurship is a category.
How did you decide what categories to put on here, and when did you specifically add entrepreneurship?
So entrepreneurship was kind of an interest of mine from the get-go. I think I had – I accidentally got the bug without knowing it when I was a kid, and I had a lawn-mowing business. And while everybody else was getting hourly jobs or whatever, I’d go out on the weekend with my brothers and we’d do 20 or 30 lawns and you make a few hundred bucks and do that at a few hours a weekend. And we just kind of looked at the numbers and we’re like, “It doesn’t make sense to go work at a fast-food place or anything like that.”
And so when I finally got a job and actually started making enough money to live so I could actually start thinking, freeing up some brain space to think about other things, I was always coming up with ideas. It was just figuring out if I had the skills to implement them, if I had the money to figure out how to get it started.
And from very early on, I just started freelancing for people. I was doing a lot of social media management, a lot of SEO, PPC, social media stuff, and email marketing. And those are kind of --
And this is after you got your job at the marketing agency?
Yeah, after I actually started learning some of these skills. And so once I started learning them, I was like, “Okay, well, there’s other people out there that – they’re not going to pay me – they’re not really clients that our company would go after because they’re – it’s not enough money for the retainer for our company to make sense.
But if I spent five hours a week of my own time hustling, I could probably make a little bit of money on the side. And whether that’s $200 or $500 a month; ended up getting up to $1,500 or $2,000 a month at one point. I was like, “Oh, well, I actually have some – this is actually an income. It’s not a full-time income, but it’s something.”
And in there, I had transferred – I got recruited away from this company that I started at and gave me my shot. And I started working with this other company in a bigger national capacity. And it was way more money. It was more interesting clients, but it was much more formal. We were doing internet marketing, but we had many of the traps that you would have at a normal 9:00 to 5:00. You had to be in a specific time, you needed to wear a specific outfit, there was a specific dress code, and all these things.
I was just thinking about, “I can do this job anywhere in the world. Why do I have to be in Milwaukie, Wisconsin of all places to do this?” (Laughter.) And there’s a long story there, but basically, within six months of being there, I knew it was not going to be a good fit long term.
And I had such low tolerance for not being – I don’t want to say, “Not being happy,” but I knew how effective I was being. I saw the return that I was making the company, I saw what I was getting paid for that. I did sort of the mental calculus like, “Okay, I’m bringing in 40% of the revenue for the company and I’m not making 40% of the revenue.”
And I just did some of the calculus and I didn’t really jive with the culture very well. And within six months, I ended up leaving. And I remember thinking – I was having such a bad time there that I remember, “I don’t care if I have to go back and work at UPS again, but I don’t want to be here.”
So it wasn’t just the money then. It sounds like you hated the job itself.
That was interesting, because it was one of those things where if it wasn’t so bad, I probably would have stayed. A lot of times, people end up in decent situations that aren’t really bad, but they’re not as awesome as they want them to be. And so because they’re an either/or, they just kind of stay and kind of hang out in the mediocre aspect of it. And for me, it just got really bad. I didn’t get along with my supervisor very well. There was just a lot – yeah, it just wasn’t good.
And so within six months, I had been kind of hustling on the side, making $1,500, $2,000 a month or something like that. And I was like, “You know what? That’s not a ton of money.” But especially in the Midwest, I could pay my bills and I could try to figure something else out. And most of all, I don’t have to be here. (Laughter.)
So that was kind of where two or three years after – I would say two years after I had started the blog, I kind of had transitioned. And I don’t know if I would say I was an entrepreneur at that point. I was kind of side hustling and doing some other stuff. But that was when I was like, “Okay, I’m going to have to figure this out on my own.”
So on your Impossible List, you’ve got kind of the first item under entrepreneurship is, “Start my own marketing agency.” And then one after that is, “Make a full-time living online.”
And I think this process that you went through of being an employee and then doing contract work, and eventually starting your own business is such a classic way to become an entrepreneur really, because you kind of see all sides of the equation. And it’s more of a gradual slope rather than just quitting everything and just saying, “Day one, I’m a business.” Did you have a plan in mind when you quit that you were eventually going to be full time on your own, or was this sort of like a stopgap measure until you found another job?
It was definitely I was going to try to figure out how to be full time. So once I left, I think I went back to Chicago for a month and a half or something like that. And then I went to the Dominican Republic, and I had some friends there. I was living – I think rent was $100 a month or something. I was basically, “I have to baseline my expenses as much as possible.”
So the idea was, “Go to Dominican Republic, baseline your expenses, and then try to ramp up and start making a full-time income so you can come back as soon as possible.”
So I went there and kind of started scaling some of the consulting stuff I was doing. I was kind of messing around with products, coming out with information products with IMPOSSIBLE. I think I came out with a triathlon product, was the first thing I came out with on how to run your first triathlon. And that was a – it was interesting for me as far as making a product, but I think it bombed and we sold a few copies. And I realized that of the subset of people that are interested in fitness, the subset of people that are interested in running and the subset of people that are interested in running a triathlon, it’s pretty small. And I didn’t necessary have the cache to pull that off.
So that didn’t go very well, but it kind of got me in the practice of actually testing things out. And so I started just getting into this space trying a bunch of different things. And then this is where I believe I started talking to a couple friends. I was doing a six-pack challenge that got a lot of attention, and I was doing a modified form of the paleo diet.
And I had mentioned “paleo” offhand to someone, or I think in a blogpost. And I just got a ton of feedback on it. They were like, “Oh, tell me more like paleo.” And I was like – it was kind of a throw-away comment, and everybody started glomming onto it. And I was getting all these emails on it and I didn’t want to respond to all these emails. And so I just made a one-pager website of all the questions I was getting asked. And anytime somebody asked me a question about paleo, I just referred them to the link.
And that’s kind of when this paleo nutrition business started to take off. And that was, I want to say, 2012 or so. But it was just one of those things where the benefits of IMPOSSIBLE – there’s a business aspect to it, but there’s also an experimental aspect to it where it gives me an audience and it gives me a way to talk about different things that I’m interested in. And then I get to hear what’s resonating with people, and then it makes it easier to double down on some of that stuff.
And so that paleo one-pager turned into a whole spinoff of a website, plus a meal-planning service, plus two different apps that we have and some affiliate products that we’re partnering with.
So it’s just kind of – the formula, if anything, is writing about things that I’m interested in, doing interesting personal things, and then figuring out what people are glomming onto, and then doubling down on that.
I think that’s such a great insight that if you have an audience, you can kind of just put things out there. You can put out feelers. And because you have this audience, like you said, you actually get real feedback. And you can see, “Oh, I did this thing. No one really responded to it. I guess I’m going to stop doing that. I did this other thing. Wow, it’s getting a huge response. I should double down here and maybe start a business in this area.”
And trying to deconstruct how you got to this point, let’s take a step backwards and let’s look at how you actually built this audience for yourself. Because most people listening who want to start a business don’t have an audience. They don’t have a blog. They don’t really have any sort of testbed where they can throw an idea out there and see if people will respond.
How did you grow your blog and how did you get the point where when you said something, people would actually respond to you?
So I started in 2010. So it’s a little bit different space now than 2010. I think a good number of people still read blogs, but there’s just a lot of other avenues where you can do it. And so when I started out, I was just basically going through my Impossible List and doing all the things that I could do while I still had a 9:00 to 5:00 job.
And so that’s one of the things I think people miss, is that they always say, “Oh, how’d you start this?” And I’m like, “Well, for the first two years, I was just doing things that I was interested in and learning skills and getting paid to learn skills, and then also learning how to write, learning how to speak, learning how to have your own voice.”
I was doing a lot of guest posts for other people, similar to a lot of things people do now with account takeovers or podcast interviews. The tools were slightly different then. It was just a lot of guest posts, a lot of commenting, a lot of just reaching out to people that were kind of in the same space and saying, “Hey” in a genuine way, “You guys are doing really cool stuff. I’m trying to do some things that may be interesting as well.”
And I just built up an interesting friendship of people online, and then every once in a while you’ll write something and it takes off. I think I had one blogpost that I wrote about meeting Russell Kirsch. He invited the first programmable computer and he, I think, invented the pixel or the first photo.
And I met him in a coffee shop in Portland and we had a conversation and I wrote a blogpost about it. And I was a – I struck to a pretty strict blogpost schedule. And I had kind of written this thing and I didn’t really know what to think about it. I wasn’t sure if it was any good. But the schedule was coming up and I was like, “I have to publish something.” And so I think I stayed up super late, like 3:00 or 4:00 a.m. trying to get this thing done, hit publish, and woke up the next day and my whole site was down because it had gotten on Hacker News and people were just glomming onto this story.
And so all of a sudden, it was just kind of this process of every once and a while, you write this thing and you think this is going to be amazing and nobody cares. And every once in a while, you’ll post this thing that you’re like, “Okay, I’m just doing this to kind of get it out of the way,” and people glom onto it.
And there was a couple of those types of events, where I had written something that people resonated with. And then that brings in a whole new wave of people, and then it kind of goes from there.
Essentially, you’re just getting a thousand more at bats than someone who doesn’t have a dedicated blogging schedule, where you can just keep doing this thing over and over and over again, month after month, year after year. And just through sheer persistence, eventually, one of these things is going to take off. And even if none of them ever take off, you’re still going to be building up your skills, you’re still going to be adding a small trickle of email subscribers. And just through working and grinding on it, you build up an audience that gets you to the point where you can actually launch something that’s successful.
So I think that’s a story that a lot of people could learn from. It’s so easy looking in from the outside to see sort of somebody in a successful situation, where they have this business, and think, “Oh, I just want to get straight there. How do I go from zero to 100 tomorrow?” And the sort of hidden grind behind the grind, where you spent all these years acquiring the skills that you have and building up the audience that you do have is pretty much invisible to most people.
And the other aspect is, even though I wasn’t really making money on the IMPOSSIBLE blog at the time, a lot of times people would come and read it. Maybe they were my clients, maybe they were interested I was doing freelance stuff or whatever. And a lot of times, I got clients just from people saying, “Hey, you seem like an interesting guy.”
And I think two things people underestimate is, one, the value of doing interesting things, because most people are just kind of plodding through life and don’t have much to talk about. And maybe they’re bored with their job and it kind of shows. But then they kind of take that off and they go home and they what Netflix, and they don’t necessarily have anything going on.
But if you have these projects you’re building towards, even if you don’t want to talk about your job which you’re not excited about, there’s other things that you can connect with people on. So I think people underestimate the value of being interesting.
And then I think also people kind of overestimate how valuable they are sometimes. One of the things I talk to a lot of people about once they are consulting and charging people for stuff is, “You probably need to raise your prices.” But when people are starting out, a lot of times they overestimate the value of the position they’re in or they don’t realize how replaceable some of the things they’re doing are.
And so when I started out, I had nothing really to offer my boss. He could give me an entry-level job, and if I – the gamble on his end is: If I was any good, maybe it would pay off. But if I was terrible, then he would be out two or three months of his time training me, plus the money that he paid me, plus all these other things.
And so the thing that I tell a lot of people is – “Hey, I want to get started in entrepreneurship” or “I want to do something, but I don’t really feel like I have any skills yet,” and then they’re going around and trying to get these good to high-paying jobs – is “Don’t rush it so much on optimizing for revenue when you’re starting out, especially if you’re right out school.”
A lot of times, I found a lot of my friends that are entrepreneurs started working either for free or working for very little, but traded it off and said, “I’m not going to take a lot of money in my first job. But I am going to take a job at a small company where I have access to the boss and access to the knowledge.” And then kind of you work yourself into a paying position.
And then worst-case scenario, you’re getting paid to learn skills even if you’re not super pumped about the job or the situation you’re in. Taking that time and that patience to build up those skills is super valuable.
Yeah, and that learning just continues to be helpful over the long course of your life. You don’t really forget the stuff that you learn. The years that you spent working for marketing agencies and doing your own consulting, you’re learning a lot of valuable business lessons that a lot of programmers, for example, don’t know even though they might be able to code. And as a result, that kind of pays dividends.
I can kind of tell just by looking at the different websites that you’ve launched and the businesses that you’ve started, that your SEO knowledge sort of comes into play with everything that you do. For example, I’m sure Paleo Meal Plans is called Paleo Meal Plans for a reason, because you’re aware that you’ll probably rank very highly for this popular Google search term.
So I think people very much underestimate the sort of payoff that learning in aggregate can provide over time, and how many and how many people who are successful are really that way just because they spent so much time learning and trying things. And no one really just gets it first shot out of the gate without having some preparation or some learning beforehand.
There’s almost a different curve. If you take a job and you get 5% increases over time, that’s one type of curve. But if you kind of start low, and then all of a sudden you can change your earning power exponentially if you come into the situation where, okay, you spent this time learning. Maybe you’re not valuing it very high, you’re not getting paid a lot of money. But then as you’re institutionalizing that knowledge and you’re gaining those skills, all of sudden, you can take those and be a really high-value contributor within the company that you’re at, or you can take that out and do your own thing.
And a lot of times, it’s this kind of comfortable-enough situation. A lot of times, people can get themselves into a comfortable-enough situation that it’s almost too comfortable to leave and it’s too risky to leave.
One of the things that was good for me was I knew what it was like to not have – to kind of scrape by for a few months and hustle on some stuff from my early days. And so when it got time for me to leave my job, I was like, “Okay, well, I’ve done this before. I can go hustle. Instead of hustling else, I’m hustling for myself this time.”
So you did that the first time when you were just out of college. You were 23, 24 years old. You graduated in 2009, so I assume you’re my age. You’re probably 30.
Could you see yourself doing that again? If you lost everything and somehow you lost all your skills, age 30, would you scrimp and save and start from zero, or would you go the comfortable path?
Well, I think the interesting thing – the game that I play is: How many phone calls would it take for you to get a job right now? Because I think about that all the time. I think one of the things about entrepreneurship is you’re like, “Tomorrow I could wake up and everything – my computer’s nuked or whatever.”
And so the thing that’s nice for me is – or it’s not nice. But the thing that I think about is, “How many phone calls would I have to make to get another job?” And the answer is probably one, maybe two. And at this point, it’s because of the connections I’ve made and the people I know and the reputation that I have. I don’t think it’s cocky, but it’s something that you – it can go bad, but it’s not going to be so bad to the point where I’m going to be in the streets or something like that. I might have to scrimp and save and do some stuff, but I could always get a job 9:00 to 5:00 and then hustle on the side.
And would I be okay? I’d probably be okay doing that actually. Sometimes a job seems a little bit less stressful than entrepreneurship. You’re like, “Oh, you just have to show up for the 9:00 to 5:00 and then you clock out and you get paid the same no matter if customers are happy or sad or whatever.” There’s something about that that’s slightly nice and comforting.
What I think is tougher is if you end up at 30 and you don’t have a specific skill that you’ve honed, and a specific skill, different relationships, or different connections. And that’s not to say you can’t build those. But that’s something that I think there’s a job security that comes from just kind of – a lot of times people rely on their job for job security instead of relying on kind of institutional knowledge they have, the reputation, the relationships they have, and then evidence that they can produce, which I think are side projects or just things they’re doing on the side that make them interesting.
And like I said before about people underestimate the value of being interesting, I think a lot of times, people will give you a second look just because you’re doing something that they can point to and say, “Hey, that’s kind of cool. I’d like to help that guy out.” And if you can differentiate yourself in that way, I think it’s super helpful.
So let’s talk a little bit about Paleo Meal Plans. You did an Indie Hackers interview on this about a year, year and a couple months ago. As you mention now, it started off with you just blogging about paleo and people being interested in it.
How did your blog about paleo turn into this products business, Paleo Meal Plans?
Yeah. So it started off as a main site. The main site was UltimatePaleoGuide.com. And it just started – I’d quit my job and I was doing a couple information products on IMPOSSIBLE. And I knew SEO and PPC pretty well.
And so once this side project kind of got traction, then I was like, “Okay, maybe I’ll actually focus on what the keywords are, building out the site structure, all that stuff.” And so kind of got into the point where that site started getting enough traffic that required its own servers. And then I was like, “Okay, well, it’s not really making any money, so I should probably have it cover its server costs.”
And so we just put up a bunch of affiliate links. And in the health and nutrition space, that can be – a lot of people sell stuff really hard, which I’m not a huge fan of. But in that space, it works sometimes. And so we had a couple affiliate relationships that it helped cover hosting costs, but it didn’t necessarily make – you weren’t like, “Oh, my gosh. This is so awesome that we’re doing it.”
And so maybe a year, year and a half into that site, I decided that we didn’t really want to just be selling other people’s stuff. There were a couple reasons for that. One, you have – I don’t like it from a strategic standpoint. It feels really vulnerable if you’re just an affiliate for someone else. There could be another site that just pops up and is a better affiliate, or maybe they do one thing different and then your revenue goes down by 50%.
I’d been at a company previously that was a big affiliate for, I want to say, TV for Dish Network. I think they were bidding on PPC placements. And one day the Dish Network called them and said, “You can’t be in the second position anymore. You have to go to the third position.” And they just did it because of internal reasons. And overnight that company lost, I want to say – they laid off like 100 people the next day.
And so I just knew that being an affiliate for stuff was – it’s a nice additional revenue stream, but it’s not good as the main revenue stream.
And so we started looking at building our own products. We built a 21-day paleo challenge, which kind of helps people get onboarded with what paleo is and how to get started. And then --
Let me ask you. You say, “Building your own products.” Your skillset at this time, you weren’t a programmer, were you?
And so I think it’s interesting, because a lot of people are in your position where they might have some marketing skills or they might not, but they certainly don’t know how to code. And they think that means that they can’t build a product.
And yet here you are, not a programmer, and you’ve launched numerous products at this point. So how do you define “build a product,” and how do you go about thinking how to do that as someone who’s not a programmer himself?
So this is actually an interesting question. Actually, I’ve done a couple talks on how I conceptualize different products. Layer one is just information. And I want to say, six or seven years ago, there were just a lot of information products out there. People would say, “Okay, here’s x, y, z.” Now that Google search has become a lot more competitive, a lot of those information products have turned into just very long blog posts that people aren’t charging for anymore.
But kind of the first level of products that I think about when I’m talking about online business or content businesses are kind of resource guides. And you’re trying to help match a goal – information that you may have or you can research to a goal your customer might have.
And so sometimes it’s viable in a market; sometimes it’s not. But for us we found that, okay, there’s a lot of information about paleo out there. But if someone’s wanting to know how I actually get started with paleo on a day-to-day basis, how do they – how do I actually do that?
And so we created a 21-day challenge, which was basically – I think the first iteration of it was a 21-day email series. When they first signed up, they got – here’s all the resources, here’s what you should eat, here’s what you shouldn’t eat. And tomorrow we’ll send you email day one. And it was basically, day one: Here’s what you should do, here’s some things to think about. Day two: Here’s some things to do, here’s some things to think about.
And then we kind of matched our own experiences with going paleo with what people might be experiencing within different weeks of actually going and trying on the diet.
And so for us, it wasn’t even – there was no programming involved. We set up, I think, an email series with ConvertKit or MailChimp, and then just started – a lot of it was writing. And it’d been the skills that I’d been working on, which are SEO to get people there and then writing emails and using my voice to communicate with people and make them feel like there’s a real person on the other side of the auto-responder.
And so that was the 21-day paleo challenge. And then from there, we decided that we wanted to have a recurring source of income because the SEO traffic could come and go, but we wanted to build a stream of income that would be there on a regular basis.
And one of the things that we found was that there’s a certain segment of customers that want meal plans, and they want that on a monthly basis. To start, that wasn’t even a programmable thing. We just literally made the meal plans by hand, put them in a PDF, and then every time Saturday rolled around, we’d send out a meal plan. And that became a recurring revenue source for us. And that’s kind of how we got started in this space without having any technical skills.
That’s fascinating. Because I think if you’re coming from a position where you understand business, where you’ve been doing consulting and you’ve been working with these companies for so many years, so you understand what people will pay for, you understand what a value proposition is, you understand how important it is for you to get into the customer’s shoes and try to figure out: What’s hard for them in this process of adopting the paleo diet?
And then you can come up with a solution. And whatever that solution is, as long as it solves the customer’s problem, that’s a product. Coming at this maybe without those business skills who don’t really understand the concept of providing value to customers – when they think “product” they just think “features.” And so they think “product,” they think, “Oh, that means I have to code something.” And as a result, they end up building all sorts of apps that aren’t really valuable to anybody, but surely enough require someone to write code.
So I think it’s fascinating that you’re able to create a valuable consumer product just by understating your customers and what’s tough for them. And you don’t have to code. You don’t have to have any sort of super-advanced skillset other than understanding who your customers are.
Well, one of the things that I think we talked about on the text (ph) interview from last year was most people try to over – we eventually got into the point where I was bringing developers on. And I still haven’t done very much coding at all. I’ve done very little stuff. But we brought in developers and developed some more things.
But one of the things that I find people do way too much is they overbuild everything. And instead of focusing on, “Okay, what’s a little thing that you can do that’s going to add a little bit of value to someone’s life” and they’d be willing and happy to pay you on a regular basis for that, they try to create these double-sided marketplaces, or they come up with this nebulous feature set, or they won’t release this one thing until it’s got all 427 features on it. And then they end up six or 12 months in and they’ve got this quote/unquote, “50% done project” that they could have released in month one and then just iterated on it over and over and over again.
And I just find people – for me, a lot of my stuff comes from my own limitations, where I probably would have gotten a normal job when I first started, but nobody would hire me. So I had to figure something else out. And maybe if I had the fund and the resources or the technical knowledge to go build a meal-planning service from scratch, I would have done that. And it would have taken me six months, two years, whatever the timeline was.
But because I didn’t have those luxuries, I just had to figure out how to get it done. And I just went out and was like, “Okay, we’re going to make this thing, and we’re going to do it every single week and we’re going to get done by Friday. And those are the stipulations and we’ll send it out Saturday.” And that was kind of the framework we started with. And it was a hustle game early on, and we just figured out how to do it.
I don’t know if you ever read Thinking, Fast and Slow. It’s one of my favorite psychology books. But he talks about this phenomenon called “substation,” where if you ask somebody a question and the question is too hard for them to answer, they don’t say, “This is too hard for me to answer” or “I don’t know the answer.” They actually just substitute that question for an easier question.
So if I’m like, “Okay, who should be president?” You don’t say, “Well, let me add up all the information on this person’s background and history and their decision-making capabilities and the currency of the world and the economy.” It’s just too big of an equation. So you substitute that question for, “Who do I like more,” which is an entirely different question, but it’s much simpler and easier to answer.
And I think when you’re building a product, if you’re like, “Who’s going to buy this or why are they going to buy this,” that’s a tough question to answer, especially if you’re not really sure why people buy things in the first place.
And so it’s easy to substitute that question with an easier one, which is,” What features should I build that will be really cool? And then you just go on building feature after feature for years and you never really hit the simple thing that people will buy.
And I think your business is such a good example of that in action, because you’re literally selling meal plans to people. This is just text and an email that you provide to people, and they’re paying you, I presume, a monthly fee to buy these meal plans. And it’s so simple and it’s so straightforward, but a lot of people would overlook it because they’re substituting the actual question of, “How do I provide value to these customers” with a totally different question, which is, “What features should I build that would make a cool looking product from my perspective?”
Well, yeah. And the thing about it is – the other thing that I notice: A lot of our stuff is just kind of realizing where our deficiencies are and then trying to overcome that. So a lot of times, the reasons we built our own products is we saw the dependency on affiliate income is – that’s not a great position to be in long term, and so we started building towards that.
We were doing the text meal plans for a long time, and we go to a point where we’re like, “This is really great, but we’re starting to get feedback from customers that they want to have some more dynamic aspects to it, and they want to be able to do x, y, and z.” And that was awesome, because instead of guessing what they wanted, we just have built-in people that are already paying us that are saying, “This is great. We’re happy, but it’d be awesome if we could have x, y, and z.”
And so we actually started the process of building this to be much more of a technical piece of software; basically, this spring right now. And we’re kind of building a lot of the features that we’re getting asked to by paying customers. And I want to say “paying customers,” because a lot of times – we get a lot of traffic. We get a lot of people that are just drive-by asking questions or whatever. But if we try to do everything that just every drive-by person wants, it’s going to be really tough.
And so I think a lot of times, people get confused and they see all these people saying, “Oh, I would totally buy if you added x, y, z.” And that’s a lot of noise to filter out. And so what’s been awesome is having a built-in set of customers that are saying, “Hey, we already like the product. Here’s what we would like to even like it more.”
That gives us verified, actual feedback because they are already paying us, and then they’re funding the kind of next development of the project. And that’s been really cool because it’s a more sustainable way for us to build it than guessing and then people saying, “That’s okay, but I actually wanted this.”
So on your Impossible List, one of the items that you have on your list of things to do that you haven’t checked off yet is to create a seven-figure company. Is that what your goal is for Paleo Meal Plans, or do you think it’ll be a different business?
That’s a good question. So one of the things that I found with Paleo Meal Plans and the paleo business in general is that I really like being in the health and fitness space and IMPOSSIBLE is part of that health and fitness space.
And I believe in the paleo diet. I don’t like the term “diet,” but I think it’s a really baseline for – when you look at the stats that the CDC releases, I think 30% – this is a few years old, but it’s probably worse even now. 30% of the U.S. is obese, 60% is overweight. And most people just a standard American diet. They eat a lot of low-fat, high-sugar, high-carbohydrate content. And I think the paleo diet is a great fit for a lot of people.
The paleo business is also – has a different demographic than what IMPOSSIBLE has. And so my interest with IMPOSSIBLE is really more performance and challenge-aligned. And my interest with the paleo sites are more kind of general interests, so our demographics are quite a bit different.
So that’s a long way to say is that my goal has been to kind of free up some of my time from the paleo business to work on IMPOSSIBLE more. And I’ve talked to a couple different ways that I’ve looked at doing it. People have been interested in buying it over the years. And when I talked to a couple friends that have sold their companies, they said, “If you weren’t interested in this space at all, maybe it’s nice to just get rid of and kind of clear your mind.” But if it’s an asset that you can use” --
One thing that a lot of people me was, “If it’s an asset that you can use, or even just the asset of having a company,” a lot of times people would say they sold this business, and then they got this chunk of money, and then they spent all their time going around and chasing other businesses that were throwing off cash, like the last business that they just had sold.
And so the thing that, as I talk to more and more people was they said, “I really wish I would have just hired a CEO and figured out how to kind of own it as an investment business, and then worked on other things.”
And so that’s a very long answer to say: One of my goals with paleo is to start the process of replacing myself in the company, and kind of leveling myself out of the business to be a point where – I’d like to grow it substantially. I have a internal – I don’t know if I have an internal belief, but part of me wonders how much we can do with Paleo Meal Plans just as a – I think if we keep it to paleo, it’s a little tough to hit that seven-figure mark, and so we have some plans to kind of expand a little bit beyond paleo.
But I think my main goal, whether or not that’s seven figures or not, is to kind of replace myself in the company and get myself to a point where I have a team that’s executing a lot of things without me, and doing a lot of the things that I think I’m unique and irreplaceable and all this other stuff. As I’ve started the process of hiring over the last year, I found out that, “Oh, there’s a lot of people that are doing way better than me at a few different things.” (Laughter.)
And so I would say my big goal with that is, first, to kind of get out of my own way; and then to own it as a piece of other different – to own it as an investment property of internet real estate, if you will. And I think if I do that, I think one of the byproducts is that we’ll be able to grow a lot more.
And I think I think one of the biggest issues that I’ve had with the business is that I’ve been in my own way, and I’ve been kind of hesitant to put in key players and to make that investment in them, because it requires a different set of skills and it requires different focus from me; not just hiring contractors here and there, but building a team, investing in them, and letting them know that I’m empowering them to do the things that they’re good at.
So that’s been kind of the shift over the last six months where I’ve been like, “Okay, this is a whole different challenge going from me doing all this stuff to me kind of creating the structure and the infrastructure for the business to kind of grow without me.”
That sounds like something that’s worthy of your Impossible List. Speaking of which, out of all the things that you’ve completed, or maybe even the things that you haven’t completed, what on your list do you consider to be the most impossible?
So last year, I finished the 777 Project, which was – I was running seven ultramarathons on seven continents to raise money to build seven schools with Pencils of Promise. They build schools in Guatemala, Laos, and Ghana in under-resourced areas, training teachers, and kind of give people a baseline in places that don’t have it.
And so that was the biggest and toughest thing, because I launched that, I want to say, in 2014. And I didn’t finish it until 2017. I got hurt physically. I busted up my ankle pretty bad. And then as soon as I got kind of fixed up from that, I had a lawsuit with my business, which I don’t know if you want to talk about. But I had a lawsuit that took 18 months to resolve and kind of was a resource, money, energy drain on everything.
And then at the end of that, it was two years after I’d started this thing, and I think one race down and one school built or something like that. And I just kind of had to look myself in the mirror and say, “Hey, are you going to” – it had been 18 months since I’ve done a 20-mile run. And I was like, “Are you going to do this or not?” And I ended up running kind of one race as a test race in Chicago, and then I ended up running five races in, I want to say, three months at the beginning of last year to kind of finish out the challenge. And then we ended up raising – our goal was $175,000 to raise and we ended up raising close to $193,000.
So that was its own crazy challenge. And I thought the hardest part was going to be the running and the fundraising. And the hardest part of it was kind of maintaining my mental state while I got hurt, and then keeping my head above water for the year and a half and the two years that we were dealing with this lawsuit that was just kind of a chain around my neck for a while.
And finishing both of those and then going to finish these races, it was an awesome way to kind of kind off the year last year. And when I finished it and got it done, I just kind of was stunned a little bit myself.
So I would love to talk about the details of this lawsuit because it sounds fascinating, but how much time do you have?
I’ve got time, man. I might have to pop in and say “cut” if I say something about it that I’m not supposed to. But yeah, we can talk about it. I mean, I have a book I want to write on it because it’s – I got myself into – I didn’t do anything wrong. I just ran up against a guy who had a lot of money, so it’s hard to win those fights.
Okay. Well, now we have to get into this. What happened?
So I started my company in 2012. And so my company is called IMPOSSIBLE and we have a couple different projects that we run, so IMPOSSIBLE Fitness, IMPOSSIBLE Nutrition, the website is ImpossibleHQ. But the brand and the logo are pretty distinct as IMPOSSIBLE.
And we ran into a situation where our legal company name was one thing. And while some of our other assets, our other IP, were trademarked, our company name wasn’t. But we were using that company name in different places. And it was in – it was registered as an LLC. And every time our customers got a receipt, it printed that name with the company on it. And it was IMPOSSIBLE “blank.”
And someone trademarked what our company name was. And so we ended up at the point where they trademarked it. And then they gave us a call and they said, “We’d like you to change your name.” And I was like, “I don’t think we have a trademark, but I don’t think we have to do that because we have prior use and all these other things.”
And then next thing I know, I woke up to a phone call from a lawyer that I never met. And they were saying, “Hey, I saw that you’re getting sued in the Fifth District of Texas and I’d like to represent you,” blah, blah, blah.
And I was like, “I don’t think you have the right number. I think you’re – I don’t think you have the right number.” And they’re like, “No, no. It was just filed.” And they gave me all the details. And then I’m like, “Oh, now what do I do?”
And so for the first six months or something – lawsuits go slow. So first three or six months, I was like, “Well, I’m obviously in the right. I know I’m in the right. I’m not going to fight this if I’m in the right. They should just let me win because I have all the details.” But that’s not how lawsuits work.
So I stumbled around for the first, I want to say, six months. And then we started to respond to some other things. And long story short is I tried to cheap out on lawyers by using friends and other people that kind of knew the situation. And what I didn’t realize was this guy that had filed this trademark and was suing us had been through a bunch of different lawsuits before, had a bunch of money, and --
He knew what he was doing.
Well, he wasn’t going to – he could afford to just bleed us dry if he wanted to. So what ended up happening was we kind of bumbled a lot of responses. And they saw that – one of the guys that was quote/unquote “helping me out,” and this is why I say to everyone: Don’t use your friends for legal advice. Because he was a lawyer, he had his credentials and all these other things. But because I wasn’t paying him his full rate, he doesn’t – if you’re not paying someone their full rate, you’re not always top of their list.
And so he ended up responding to a bunch of stuff late, and we ended up getting in a lot of trouble for it. And it wasn’t until I realized that we were in a bad situation that I was like, “Okay, I have to get really serious about this.” And ended up interviewing, I want to say, 20 or 30 different IP lawyers and kind of vetting, talking to all my friends in the domain name and trademark and anybody who had dealt with anything like this. I was like, “Okay, who’s your top two or three names?”
And I ended up using a guy named David Weslow from Wiley Reine. And he kind of helped me turn the whole case around and helped me kind of dig myself out of this hole that my quote/unquote “friend” that had kind of gotten us into.
And ended up getting to the point where the case was settled. I can’t really say a lot of details about it. But when you’re going up against a guy with pretty much an endless bank account and he initiated the lawsuit and then they want to settle with you, it ends up being – it’s a lot better than getting sued into oblivion.
So it wasn’t really great. We had to change our company and a few other things. But all of the rest of our IMPOSSIBLE assets were okay.
So that’s a long story. I might have to listen to that to make sure I didn’t say anything I’m not supposed to. But yeah, I mean, it was one of those things where I just thought if you had the right facts in a case that you would automatically win. And there’s a lot more things that go into lawsuits in that.
Yeah, there’s a lot of leeway. And a good lawyer can sometimes win a case that should not be won, and a mediocre lawyer can lose a case that should not be lost.
And what I also realized was the quality of lawyer you have also depends on whether or not people are willing to discuss settling with you. Because lawyers look each other up, and then they start realizing that, “Oh, he actually has” – when they’re looking at my friend, they’re like, “Oh, this guy’s” – in their eyes, they’re not worried about him. But then I got David and people were like, “Okay, maybe we’ll listen up.”
And that was one of those things that I didn’t realize at all. And we ended up having a couple different interesting trademark conversations with a couple different companies over the last couple years. But since then, we’ve kind of solidified our situation.
I have a mini book that I’ve written that I want to put out just for small, bootstrapped companies, because nobody thinks about trademarks until it’s too late. And that’s a really bad situation for a lot of people to be in and --
Yeah, sounds like a nightmare.
If you have something you care about, you should trademark it. There you go.
All right, a cautionary tale. It’s difficult, because it’s just already enough of a challenge just to start a successful business without someone coming in and using the legal system to try and ruin your day. And I know that I personally have tended to err – people are all over the map on this, but I’ve tended to err on the side of carelessness, like I’ll just worry about that stuff later and hope that nothing bad happens.
I think a lot of people, they either fall into two camps. They either fall into the, “I’m going to try to get everything situated. I’m going to file my trademark, I’m going to get my business cards, I’m going to do all my things.” And then they don’t even have a product yet.
And so the way I’ve kind of tried to phrase it is: Here’s the stages where you should do stuff not from a legal standpoint, but from a practical entrepreneurial standpoint. And here’s the point where you should get an LLC and here’s the point where you should start thinking about your IP and insurance and basic stuff like that that a lot of times they hold people back from even getting started if you know all the things that could go wrong.
But if you’re able to get traction and then use that traction to continue protecting yourself, people end up in a much better spot.
So for sure this is practical information that people need to know. And it’s not really written about as much as it should be.
Well, it’s tough too because the lawyers don’t want to write about it because it kind of – I mean, I don’t want to say it eats into their consulting income, but it also – they can’t give you too much advice without you actually being their lawyer. And they don’t want you to go do something and then say, “Oh, my lawyer did x, y, z” and you haven’t paid them anything. There’s no actual lawyer-client relationship.
So they’re reluctant to talk about it, and then a lot of people don’t know what they’re talking about unless they’ve been through hell or they’ve been through a situation like this. And the big five disclaimers at the beginning of the book that I’ll have are, “This is not legal advice, this is not legal advice, this is not legal advice.” This is basically the things I wish I would have known when I started.
And so it’ll be like an entrepreneur angle on it, but it won’t be – it’s not a substitute for a lawyer.
Got it. Well, hopefully, your book doesn’t get you into another lawsuit.
Let me ask you, totally changing directions here: What do you think has changed the most about how you view startups and being a founder now that you’ve been doing this for the better part of a decade?
That’s a good question. One, I think I realize that most people are just people and not – I don’t know. I used to play basketball, and I always looked at Michael Jordan, and you never really think he’s actually human. You just think he’s Michael Jordan. We’re human; he’s Michael Jordan. There’s no way you can even get close to that. And there’s some physical attributes and all that other stuff.
But what I realized a lot of times is entrepreneurship is much more about just – you want to put these people on pedestals and think that they’re all sorts of – they’re way different from you. And the other thing is that, “Oh, you’re so unique and you have these bad situations, and nobody could really understand you. So maybe they could do it, but you can’t do it.”
And what I realized is everybody’s got their own version of their own stuff, and everybody’s got their own reasons why. And the thing I like about entrepreneurship, it’s a little bit like sports and it’s a little bit just like – it’s about action. And the more action you do, the more momentum you make, and then you have more information so you can take more action.
And so the interesting thing about entrepreneurship is just as I’ve done more things, I have a lot more information about what does and doesn’t work, I get more information back from listeners, back from readers, back from everyone. And then I’m able to go do more things.
And so when people say, “I’m not creative or I’m not an entrepreneur,” I don’t really have a high tolerance for that. Because a lot of times, the most successful people – I think you mentioned Peter earlier, Pieter Levels, is he just goes out and makes stuff, and you just make stuff. And some stuff is going to be good and stuff is going to be bad.
And I think I said on another podcast that I just have done a very good job of having a short-term memory on all the bad things I do. And so good, selective short-term memory on the things that, “Okay, that was a terrible idea. It didn’t work out, horrible, horrible, horrible. And I’m not going to let that stop me from moving on.”
And so I would say that’s the biggest thing. It’s not this other-worldly thing. It’s a little bit – if there’s anything I had to say about entrepreneurs, is they’re good at calculating the risk that they can tolerate. And I had one friend that told me, “I could never be an entrepreneur.” And I wanted to call him out on it, but he just said, “I just don’t have the risk tolerance for it.” And on some level, I appreciated that because it was honest. But at the same point, there’s probably a business in there that he could start testing out that would be in line with his risk tolerance.
So a lot of times, people want to say, “I like to do it. I want to do it someday.” And the best way to do it is to just go out and start trying stuff, see what resonates with people, and then kind of start digging when you start seeing people respond to a specific thing you’re talking about.
Certainly, this sort of pop-culture romanticization of entrepreneurs and entrepreneurship where it’s always the riskiest thing in the world. And there’s always some life-or-death situation where the person is either going to succeed at their business or they’re going to lose everything. And so I think it’s very easy as somebody who’s working a middle-of-the-road job that you’re kind of happy with to look at entrepreneurship and think, “Well, this is way too risky for me. I don’t want to be in one of these life-or-death situations.
But I think the approach that you took – where you sort of put yourself in a position to learn and you leveraged those skills and kind of stair stepped your way into building a business, and it wasn’t this giant plunge one day out of nowhere – really mitigates a lot of the risk. Because you’re now entering this arena with a lot more skills, a lot more knowledge, and a lot more to fall back on. Like you said, you’re just one phone call away to getting back to where you were earlier.
So if you happen to be listening in and you are a little bit afraid of the risk, for sure, understand that there’s other paths too. You can start a business without quitting your day job or you can start learning the things that you need to learn without quitting your day job. So it’s not entirely this, as Elon Musk would say, “Eating glass and staring into the abyss” situation. You can do things to a much safer degree than that.
Well, the thing that I always come back to too is when people say, “I need to quit my job in order to start this business,” it’s like, if you think all of a sudden just because you quit your job – and maybe you’re working 80 hours a week and you have no time for anything else. But if you think all of a sudden, you’re going to get really prioritized with your time once you quit your job and all of a sudden you have 40 hours extra a week, and you also have to organize that time and make your own schedules and do all that stuff, and you think suddenly quitting your job and having all this free time is going to finally let you pursue x, y, z, I think you’re fooling yourself.
And if you’re not willing to put in the 10 hours a week hustling, just testing out stuff that you’re interested in, I don’t think having – for me, my own perspective is it’s really hard to manage your own time once you don’t have someone telling you what to do.
And so if you think you can’t – you need 40 hours a week to start testing out stuff, you should be able to do that in the 10 to 20 hours nights and weekends and see if there’s anything there.
And then if there is something – I know people that have built basically a second income from their nights and weekend stuff, because they have way more leverage and they don’t have the risk tolerance to go quit their job completely. But they basically just double their income because they’re willing to put in 10 to 20 hours a week of extra just on their own interesting things that mentally stimulates them and lets them have fun and make a little bit of extra money.
My brother might kill me for telling this story, but I remember I was living with my cofounder, and my brother was our third roommate. And my was working a full-time sales job. This is five or six years ago. And I remember complaining to him about something, and he just said, “Oh, man, if I was in your situation and I didn’t have to go to work, I would be so productive with my time and so efficient.”
He eventually ended up quitting his job and I started teaching him how to code. And instantly, when you remove that pressure of having a boss, of having someone who looks at what time you come to work every day, of having a paycheck that depends on you doing something, and suddenly, all that time management is in your hands, you’re not going to push yourself to the limit. You’re not going to do the amount of work that you were doing earlier because it’s just uncomfortable and to some degree it’s unnatural. It takes practice to have that much self-discipline.
I totally agree with you. Use that extra time you have every week right now as a sort of testing ground. And if you can’t motivate yourself to work five hours extra during the week or 10 hours extra during the week, then definitely don’t save up all your money and quit, thinking that you’re going to be this sort of robot-terminator working 50 hours a week the second you quit.
No, totally agree.
So let me ask you to wrap up here. What are some of your favorite books, your favorite people, your favorite talks or essays or anything that’s influenced you that you think other people listening in should take a look at?
So I’m actually looking at books around my desk right now that I’m reading. So it might be a recency bias, but there’s a couple different ones. One I read a long time ago when I first started my blog, and I’m actually rereading it right now. It’s a book by Donald Miller called A Million Miles in a Thousand Years. And it’s a book about viewing your life like a story and you as the character of your story. And basically, looking at all of your decisions in life and what you’re choosing to do as character decisions in a story.
And so instead of just being like, “Oh, what should I do today,” whatever, or if something’s hard and you want to give up, thinking about it as if you were a writer writing a character in a story. What would you want that person to do?
And that was one of the first things that ever challenged me to actually start IMPOSSIBLE and start living an interesting life, because I was living in my parents’ basement, I was watching a lot of Netflix. I was wanting to do all these things that other people were doing, but I was not living an interesting life or an interesting story. And so A Million Miles in a Thousand Years, that’s one of my all-time favorite recommendations. I think it’s great. It’s not a business book, so sorry about that.
There’s a essay by Paul Graham that I read a long time ago. I think it’s from 2009. But it’s about: Keep your identity small. I can give you the link to it later, but the idea --
It’s one of my favorites.
Yeah. The idea is that people attach their identities to all these different things. And then it basically makes you inflexible to try new stuff because it limits – if you see yourself as this specific identity, then it limits you to trying to trying other things that that “identity,” quote/unquote, does or doesn’t do.
Again, this is one of the things that I struggled with when I first started. I was like, “I’m living in my parents’ basement. I want to travel, but I can’t because I don’t have any money. And I can’t even do this triathlon because I can’t run a 5k.”
And I think a lot of people, there’s a lot of comfort in an identity because it tells you the things that you can do, the things that you can’t do. But if you constantly tie yourself to all these different identities, it really limits the amount of choices you can have and the things you can do. And so I think that’s a great essay.
And then I just finished 12 Rules For Life and actually interviewed Jordan Peterson on my podcast. And he’s got a chapter in his book that says, “Pursue what is meaningful, not what is expedient.” And that is one of the things I’ve talked about a lot on IMPOSSIBLE, is that a lot of times people want to go after thing that they think will make them happy, that seems like a quick fix.
And one of the things that I’ve talked a lot about, and the reason I like that chapter so much, was because I think some of the most – one of the reasons I call it IMPOSSIBLE is I think there’s something that you get when you push your limits, you go past what you think you can do. You do these really hard, incredible things.
When I was in Antarctica on lap seven and I was like, “I want to go, I want to be done,” and I had three more laps to go, there’s something that happens there that – it’s hard to explain. But it brings a lot more meaning, I think, to people’s lives than just doing something that makes them happy. If I want to be happy, I could watch Netflix and eat ice cream every single day, and in the moment I would have a ton of endorphins coming in and a lot of dopamine and all that stuff.
But the places where I found that I get a new peak around the corner in life, or I find a new perspective on things, is when I push myself really hard and I go after hard, difficult things. And I find that, usually, one, they’re not as difficult as I think they are; two, there’s less competition there because people are usually scared to try it; and three, they’re both more memorable and they’re the things that I look back on as most worth it. Because even though they took more resources to achieve, they had a bigger return overall.
And so those are kind of the books that are around me, so maybe there’s a recency bias there. But I think all those things had a big impact on me and they’re not just another business book.
I think early on, Richard Branson’s autobiography was really interesting to me just because it talked about business in a way that didn’t have to so stuffy, that didn’t have to be so by the book. You could basically make it up to be whatever you want. And when I look at my life and I look at my business, those are things that I’m constantly reminding myself. There are no rules. I can make it up however I want to make it up, and I think that’s pretty cool.
That is pretty cool. I think those are great recommendations. And if the books that you’ve read recently are a fair sample of the books that you’ve read throughout your lifetime, then that’s another thing you’re going to have to come on the website and share with people on the forum.
Anyway, thanks a ton for coming on the show, Joel. Can you tell listeners where they can go to find out more about you personally and about your businesses, IMPOSSIBLE, and Paleo Meal Plans?
Yeah. So you can check out everything on IMPOSSIBLE at ImposssibleHQ.com – “HQ” as in “headquarters.” I had that way before the trivia game came out, so now I might have to switch that up. But ImpossibleHQ is where you can find pretty much everything.
IMPOSSIBLE Podcast, if you want to check it out, it’s just at ImpossiblePodcast.com. I talk to athletes and entrepreneurs about pushing their limits and doing pretty cool, amazing challenges, so you can check that out.
And then for the paleo business, UltimatePaleoGuide.com and PaleoMealPlans.com if you want to check them out if you’re trying out a paleo lifestyle. And I’m on Twitter @JoelRunyon. So there you go.
Thanks a ton, Joel.
All right, thanks.
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