Welcome back to another episode of the startup therapy podcast. This is Ryan Rutan from startups.com joint as always by Will Schroder, my friend, the founder and CEO of startups.com. Will as founders, we have two modes working and sleeping. And sometimes if we're not doing one of those two things, there's this other thing that creeps in called guilt. How often is that part of your life? It's my only alternate. I joke about this, but I don't know if it's funny. I was like, I have two modes.
I mean, they're working or feeling guilty about not working. And I've been in that mode my entire life. And as I was kind of unpacking this a little bit, like I was thinking about it, I was like, you know, when did that start? And like it didn't start like five years ago. Like it started probably when I was five. That has been my MO throughout my entire life. I attach my work with my safety. Right. And that's really what it comes out to, right?
You know, as we unpack this some more, we're going to talk about the fear of that side to it. Right. I'm not working all the hours, whatever, because I'm just so excited about work. Right. In the end, I'm working all these hours because I'm in fear that if I don't work these hours, bad shit will happen. And that creates a guilt that whenever I'm not working, I'm like, oh my God, am I basically inviting bad things to happen?
Yeah. Yeah. Am I putting my safety at risk by not doing more and more and more and more and more? 100% right? And it manifests in so many ways. So I think what we can talk about today, where does that come from? Right. You know, what is the origin of that within all of us? What works and what doesn't work? You know, over the years, what tools have we found to try to help combat this or address this?
And maybe another part of what part of it is just the cost to do in business, the cost of what we do. And so if we zoom out, when you take a look at yourself, when you think about, hey, hey, I'm about to go do something that's not work. What's the emotion that like that hits you? Like, how do you process that? Yeah. I mean, first, it's that it's all the calculus around. Can I do this, right? Should I? Is there time for this?
And of course, that's coming from that place of guilt and making that trade off, right? So it actually starts with the guilt. And because if that wasn't there, I wouldn't be doing that math in the first place, right? But I started by doing that math and like, can I afford to go and play beach tennis this week at eight o'clock in the morning, seven o'clock in the morning, knowing that I could take this other call. I could do this other thing, right? So there's all that.
But yeah, I think it is, there's a little bit of FOMO there, right? And not fear of missing out on what other people are doing, but fear of missing out on my own stuff, like things that I wanted to get done, right? Is this going to compromise something else? What's this trade off going to cost? And then it's the, yeah, it's just the guilt of saying, like, I'm going to choose something other than work. Because there's always work there, right? There's never, it's like, well, you know what?
There's actually nothing to do. It's not like we're, you know, the baker in the small town is like, oh, no customers. Guess I'm going to go out and, you know, do whatever. Right? There's always something else to be done. We can always find something to fill that time. And so, yeah, I think it comes back to those feelings of guilt. You know, if I go all the way back to the origin story, if I go back to five year old me, mine is a bit different. I wasn't guilty out of fear.
I wasn't my safety that I was fighting for. It was recognition that I was fighting for, you know, there's a accomplishment that I was fighting for. I've still, same shit, right? Right back to childhood. Thanks, Bob. Thanks, Dad. I mean, it's been highly motivational. It's also completely screwed me up in a lot of ways. But, you know, we're working through it. So I think that's a big part of it.
It goes all the way back to these like really deep-seated emotional triggers around, for me, it's not like, is this going to completely shake my safety? Am I am I am fighting bad things to happen? It's, am I not going to accomplish what I set out to accomplish? Because in our household, that was the thing, right? I get where there were a few, few things in our household that really mattered. And it was, you said you were going to do something, you did it, right? You did it. Right. Right.
But it's also a hell of a demon to carry around all the time. Because sometimes you do overcommit, right? And that was the other thing. Then because we also had this accomplishment mindset, right? We can accomplish, we can do. We're capable, therefore, we must go and accomplish. You combine those two things together and you get into this phase of like overcomitting to lots of stuff, right? And as founders, holy shit, we've said this before.
One of the best things that we learn as founders is what to say no to, right? So if you are somebody who says yes a lot because they want to accomplish things and who feels guilty when they don't, perfect storm for disaster, we're being a highly motivated founder. We can question whether that's a quality motivation and whether that's healthy, but certainly does provide some motivation. I agree.
And I think for me, again, if we rewind back then, right, I definitely had a life track where bad shit happened, right? Everyone wants to believe that we can outrun it, right? For me, like when I was a kid, I didn't have a great childhood, right? My parents basically abandoned me and I had to fight for myself from like being a kid kid, like seven or eight years old. And you don't lose that. You don't forget that. No, no, of course not.
Like I would go to school every day and I didn't have lunch money, right? Which sucks. It was like a dollar back then. I mean, the 1800s when I went to school, right? Like it wasn't even that much money, but it was a relative to what I had. And so there was a small deli that was across the street from where my bus stop was, right? This is such a northeast thing. There was a deli everywhere in every corner. And so anyway, so there's this deli.
So I went in the deli and I saw that they had a whole bunch of candy there, right? And I had like a quarter, right? And it's just a broken bus. No, it's a kid, right? And I remember I bought a pack of now and leaders, right? And those like disgusting, like they were basically just like waxed with like a little bit of flavored wax. Yeah. Yeah, exactly, right? And I think it's the only I could afford. Anyway, so I bought the now and then there's like five or six in a package. It's four.
I remember clearly. Oh, I don't know about that. Four pieces. I'm gonna challenge on that. So, but I remember going in into the bus and like selling them for like twice the price. Yeah, yeah, yeah. Because the other kids have like $2.00 for like they're rich, right? You know, they had $2.00 for lunch that day. So they had a little extra cash to spend, right? And so every day I would go and buy more now and leaders and load up my backpack and go to school and sell them so I could go eat lunch.
Now stick with that for a second. That wasn't just me being enterprising. That was me being straight up desperate. Yeah, yeah, exactly. Yeah, came from fear. 100% aligned with my safety, right? And the most formative age you could possibly have, right? When I didn't even understand what economics were, I just knew that I needed money. I didn't have it. And so I grew with that fear, right? But I also started to attribute working with safety. Now working is safety, right?
But for many of us, not all of us, not working doesn't immediately spell doom, right? There's somewhere to go, right? Well, unfortunately for most of my childhood, up in saw this 18, I had nowhere to go. Yeah, there was no safety net. There was no safety net. If you stopped running, something was going to run you over from behind. I'll give you a great example. It is just so hilarious. When I went to college, went into Ohio State, same place you went. I went to the dorms, right?
And so I'm in the dorms in South Campus. And I think Thanksgiving comes around, right? And all the kids or our students are planning on going back home to wherever they're going to go. It's for whatever. But what they tell me is like, but we're going to close the dorms. And I'm like, wait, where am I going to live? They're like, will you go back home? I'm like, I don't have a home. No, that's not how it works. This is home. I had nowhere to go.
And so, unfortunately, one of my friends in the dorm, actually guy that you know, was like, hey, man, if you need a place to stay for Thanksgiving, like you can come home to my family. And I did it. It was awesome. And I had to do the same thing for Christmas. I basically had to find like these adopted. Serenade holiday families. Exactly. Because I had nowhere to go. And that's my point. Like I always had this thing where like there's no backup plan. Like I can't call home for money.
I can't go home. This is it. What I have in my pocket is all I have. And again, for a lot of people, that is the case. Fortunately, hopefully not most people. Regardless, you build this muscle that says, if I'm not hustling, if I'm not selling it, slaying in those now and later, right, I'm not going to eat bad stuff is going to happen.
No matter how many things that I did well, ship in 30 years later, you know, that I've been running startups and you know, doing pretty well, I feel exactly the same way. The same way. It doesn't go away, right? And people go, you know, you should talk to something about it. Yes, but it's still who I am. And it's tough. I think it's really tough. That's the foundation you were built on, right? It's hard to get away from these things, right?
In the same way, like I did have some of those support structures. But in the same way, like they weren't accessible to me. Why? Because of guilt, right? I knew if I needed to, right, I could reach out. I could ask, I could ask and I would probably have received, but I felt guilty to ask because I had been given so much in there. I needed to accomplish. And so like there was no version of me feeling comfortable with that.
Now, had it really come down to like a destitute situation, I would have had a safety net. It would have been there and I would have fallen into it by default, right? But it's, you know, we're talking about guilt today and guilt was what drove me to not reach out, to not make life easier, to not choose to do those things. And I think this comes back to when we start to tie this to then, you know, why is this so much more pervasive for founders? Why? Because we picked this, right?
In a lot of cases, you know, a lot of my friends, like, you know, they got their degree, then the job market was tough and they couldn't find a job so they went home to their parents, right? And that was okay, right? They didn't feel too badly about that, right? As founders, because we chose, we chose the path that we're on. And if it becomes difficult by virtue of that choice, how can we possibly, right? Because now it's pride plus guilt.
It's so like, we build these perfect storms where we don't really feel like we have a lot of choice, even if we do, right? So in my case, it was like, there was this pride around, you know, wanting to achieve what I said to achieve and guilt around having to ask for help if I needed it. And there were times where I definitely needed the help.
I mean, like, as founders, one of their not times where we need help and yet just could not bring myself to make that ask because the guilt, because I brought this upon myself, right? I don't know how it was for you, but there were definitely times where I was reminded of that, right? We talked about this before on the podcast, I think, but like, yeah, well, you decided to do this. You chose this. You could have just gone and got my job. You could have done this, right? So of course, right?
So they're making you feel guilty, right? Like, I need any help with that whatsoever. Like, hey, I got this, right? I don't need you to hold my beer. I got this. You know what's interesting though? It's like, so I'm in college and I'm starting, you know, this internet company is one of the first internet companies. And what was interesting about that is for me, it wasn't about the company. It was about the company or the opportunity we were building web pages, which I thought was fascinating.
And you were there at the same time that the internet was a fascinating place to be, you know, in that era. That said, for me, it wasn't about, hey, this is an opportunity. It's kind of like, you know, an episode we did recently talking about is it about fear or greed? It was, hey, this might be an opportunity for me to put food on my table more effectively than other ways, but food, exactly. In my options kind of sucked at the time, right? So my options, given the fact that I was 19 years old.
I was in college. There was being a typist at a legal firm. That's it. That's it. My options were so shitty. Yeah. Right? Yeah. Man, they worked me so hard at that firm. But yeah, like, I looked at it and I said, here is an option where the one benefit, risk be damned. The one benefit is no one can control my upside. Right? So I was consigned to the fact that I was always going to work for someone else. Right? Again, you know, people have this revisionist history about how things went.
Dude, my expectations were so incredibly low. Right? I had two opportunities in life at that point, as far as career paths. Career path number one was there's a sweet sales job at Best Buy. And I'm being very specific, right? Like, I remember they just opened up like a Bose store within a store in my dream job, because I was a huge Bose speaker fan and then an audio file, is that I could sell Bose speakers. Okay? So just to give you an idea of where my aspirations were, right?
I had that situation going or I could type 100 words per minute. In teere point, I had a lot of typing opportunities available to me. And, you know, I joke about it now, but that is where I was when I started the company. Yeah. That was the horizon of opportunity at that point. You bet. You bet. Every single person in my family, I have like 80 cousins, because there's been so many the forces. Every person in my family is in some version of a trade for the most part, right?
Painting, mechanic, carpenter, you know, landscape or whatever. And I just assumed that's what I was going to do. I just assumed I'd be living the van life at something way, right? In whatever, Ironic that my number one hobby is being a carpenter now, but that's by a choice. Thank God. Is it though? You'll have to ask us like, I'll just something. It's all coming back.
But anyway, so I looked at this opportunity to be able to build something for myself as really just a mechanism that wasn't having to rely on someone else, right? It didn't work for a long time, like just, I mean, people forget about, again, the revision in history, like, oh, you started a company and did well. No, yeah. Right away, right? We both had the experience of getting paid for web design and development work in a food tab. We both have this experience.
That was that was where the world was at at that point. You could still pay developers in ribs and grilled cheese. Dude, totally. And honestly, and we were excited about it. Oh my God. It was, it was a huge win. It was real money, because not only was it real money, it was real money. You couldn't waste on shit. You didn't actually need, right? It was, it was, it was cash that was going to keep me alive. Right? It was perfect. Yeah. You called him a singing for your supper quite a little.
Yeah. Here's where things started to turn. Right? In other words, this is where the guilt, if you will, started to become a superpower. All of a sudden, I found something, entrepreneurship, where I was rewarded in a very deliberate way. When I say rewarded, not necessarily paid a ton of money, but I mean, like my efforts went somewhere that felt meaningful and it was uncapped. Now, the uncapped thing kind of became a bit of a liability, right, over time. So let me see.
With entrepreneurship as everyone listening knows, you can invest as many hours as the world will allow you, right? There actually isn't a cap, right? Now, in most jobs, you have a start to finish, you clock and you clock out, you leave and you're done, right? And the job will be there tomorrow. And if you work 10 times harder, it's probably going to be the same job tomorrow. Take someone who's a professional services person, like a lawyer, let's say, right?
The nice thing is if you work more hours, you typically build more hours if you have the business and you make more money. And that's cool. But the job will pretty much be the same job the next day, the next day that you're still going to be slaying illegal, right? Yep. There's no building there, right? Correct. By and large, you're still trading exactly some linear version of time and money. You bet. You're not doing a product, you know, building something new.
Their infinite uses of your time, you know, there's marketing, there's products development, there's all these things. So if you're willing to put in 10 times more effort, you can actually get 10 times more back because you can actually get things done that other people can't. So this was like giving crack to the crack addict. I was like, wait, I have something now that if I want to work 100 hours a week, I'm rewarded for it. Well, shit, I don't want to problem working, right?
I'm about to work 100 hours a week for a very long time. And so what happened was all of a sudden I put this, this angst in this fear into something productive, which up until now I had not, man, like up until now I channeled it into the dumbest ways possible, see my typing career, right? In order for you to pay money. And it comes in handy. I've seen you carry on five slack conversations simultaneously and no one else is keeping up with you.
The words for a minute are amazing, my accuracy, not so much, but regardless, the problem I'm going to phrase it this way is that it started working and it started paying off. Yeah, yeah, you become addicted to it. Yeah, man. I started to associate working all the time in the reward that comes with it with safety, right? And I was just like, the only way for me to be safe is to work every waking hour. And no one told me to do that, right?
No one like came to me and it's like, well, if you don't do this, whatever, they didn't have to. Same for you. In the same way you're saying that no one had to tell you to feel guilty or like question whether you could go back to somebody and ask for something. One of the few things I didn't need any help with at all. Yeah. I had that one all by myself.
Yeah, man, it's crazy going back to that same period in time and having that kind of similar realization to where I can put myself into something. And I think for me, it was this realization that not only did it, it created some cash, but previously there were a lot of, because I had a lot of entrepreneurial type things or a lot of hustles as a kid, let's say, right? Like I'd fill hay in the summer. I'd go out with the truck and pull people out when they got stuck in the snow.
Like I always had something I was doing, but it was always trading time for money. There was very little build to it. When I realized that all of a sudden as you started to pour yourself into building the agency, not only was I trading time for money, there was something else that was happening in the background. I was building assets.
I was building value of its own and it was starting to compound because prior to that, there was always this ability to say, well, do I actually need any more money right now? And if the answer was no, then there was no guilt around it because I didn't need it. So it's okay. I don't need it. There's nothing that's going to happen. Nobody was relying. I mean, nothing was counting.
This is, I think, the other thing that happens the further you go on entrepreneurship, the more surfaces get exposed to different types of guilt, right? Now there's guilt around. Yeah. But if I don't show up and I don't build this other thing, right? Am I holding something up from another team? Am I keeping a client from achieving what they want or a customer from getting the satisfaction that they're after? Am I slowing down things for my investors?
There's all these new vectors for guilt that start to appear and that just compound that effect so much. It's like, okay, we don't need any more money right now. We're great. But there's that feature we've been wanting to add or there's that new teammate we want to hire. If we hire them, then we got to onboard, we got to pay a salary, we got all this other stuff that happens. And you just create this web of new guilt to get stuck into.
But again, it was all very happily taken on and I don't think that we realized the danger in what you're building at that point. I mean, you're building something great. You're also building this guilt trap that starts to just be, it's a seven headed hydra that you can't seem to escape because there's so many places that it can come from. Even if you're working all the time, there were ways to feel guilty.
And I'm sure that you go through the same thing where it's like, okay, I'm working on something. But then there's the guilt around, is this the most important thing that I should be working on? So even while we're killing ourselves, we're still guilty about it because maybe I'm not killing myself right away. Yeah. I hate to say it, but I think also coming from just a different era, there was no ability and hard work, right?
There was this idea that if I'm working all the time that I'm a better person, right? Now, I'm not saying that's true. I'm just saying that like you could feel good about yourself about working all the time. Now, that changed and we've chronicled this over the years about how the dogman, the work ethic of the average person, particularly among startups has changed. People introduced this new concept that again, this is going to sound heretical didn't exist called work-life balance, right?
I had literally never heard that phrase until like 10, 15 years ago. I didn't even know it existed, right? And when I did hear it, I thought it was hilarious, right? And while we talk about why that's important, they're still a part of me, you know, I won't put words in your mouth, but they're still a part of me. That's like, yeah, but not really. You still have to work all the time, right?
And again, even though theoretically, even though theoretically, I should say that I'm I should be separated from that, right? And we're hard enough for long enough and I've achieved enough that being able to put food in my mouth is no longer an actual deal issue, right? And not because I'm fabulously wealthy, just because I've built the tools to put food on table, right?
Like in other words, if this thing doesn't work, capabilities making sure the next thing puts food on table, but that's not the way I feel. Right. No, guilt will not allow us to go there. We have options, but we can't accept them. And it was like me say earlier about there was a safety net for me.
There was a support structure, but it wasn't an acceptable choice because of all the other things that we've talked about today, all of these other things that we've built up that put us into this position, you know, where we start to feel landlocked by this thing that we built and this has to be the thing. I will feel guilty if I don't work on it. I will feel guilty if it doesn't succeed.
I will feel guilty if it doesn't succeed to the level that I think it should, which by the way keeps moving higher, the more successful we are, so much done pack here. What's crazy is that the problem for me is that it rewarded me for so long and I'm not making it unique to me. I'm just saying I can only speak for myself. It rewarded me for so long that the hard work and basically when I say hard work, I'm really talking about guilt, right?
Just to be clear, when I say hard work, I'm just talking about hours, et cetera. I'm saying my guilt was rewarded. I was guilty about not working. So I just worked all the time. It was the only way I felt solid, comfortable, and it basically kept that fear at bay. When I stopped working, when I would do anything, right? Even the most mundane things, right? We talked about this before.
When my son comes in the room, right, when a little will comes in the room, it says, hey, dad, blah, blah, blah, whatever. It doesn't matter what you say, right? I hesitate. I don't mean to say, hey, son, what do you have to say? Because it's really cool that you're in the prime of your childhood and you should get all of my attention. My calculus starts like this. Okay, if I turn around to talk to, this is so dumb, just be clear. But that's why I'm sharing it, right?
Because I'm sure there's other founders in the room that are like, you know, I kind of do the same thing. So I'll be interested to hear what you're about to say. I do a quick calculus in my head. It takes a brief second, but it does happen is what my son's about to say more important than what I'm about to do. Now every parent has that thought, every human has that thought, right? Mine's baked into the fact that I'm only certain that my time is well spent or properly spent when I'm working.
Everything else is a condition outside of that. Like me working is my baseline and everything else isn't anomaly to that because everything else for me, sadly, is a distraction from allaying my fear of not working all the time, right? But right, here's what happened. Like, I think one of my greatest curses was that this formula worked for me and it worked really well. You know, something that's really funny about everything we talk about here is that none of it is new.
Everything you're dealing with right now has been done a thousand times before you, which means the answer already exists. You may just not know it, but that's okay. That's kind of what we're here to do. We talk about this stuff on the show, but we actually solve these problems all day long at groups.startups.com. So if any of this sounds familiar, stop guessing about what to do. Let us just give you the answers to the test and be done with it. That's the thing, right?
You know, I think, and it teaches you to be transactional about your own life, right? Which has benefits, right? Definitely has benefits, right? To your point, it worked until it doesn't. Yeah, exactly that. And until it doesn't. It worked great until it doesn't, right? And so for years, decades, I was known to myself as I'm willing to work every waking out hour. I'm willing to work harder than anyone else to achieve what I want to achieve.
When people hear that they're, oh, because you wanted nice shit, nope, because I didn't want to go back to selling now and later as food, right? Like you got to understand this isn't what people think it is. People think it's, oh my God, you know, you just wanted that next private jetter or something like that. Right. Right. No, not at all, right? Like what I wanted was the ability to know that it couldn't all be taken away from me. I mean, we've talked about this before.
Every time, like I leveled up a little bit in life, the stakes went up. That's exactly it. Yeah. We just keep moving the bar. Like either they don't intellectualize because they haven't been there yet or they don't intellectualize because they don't understand what's actually happening. Here's an example. When you and I think about our worker in by proxy, we think about our safety. I bet I know what comes to mind. We both have kids in private school. Yeah, exactly.
If we don't get our shit done, right, we're going to have to pull our kids out of school, right? Which makes us a horrible father, a horrible protector or a horrible whatever. Like that is real shit. Now from the outside, people look at them and go, oh, must be great that you have your kids in private school. Yeah, man, I worked really hard to do it. But guess what?
I also now think every single day that if I eff this up, I'm going to strip that commitment all we've done is stack consequences under the table. It's not as awesome as it sounds. It's painful. Mo money, mo problems, right? Like as we achieve different levels of success, then that comes with some nice cities and the watermark just keeps moving higher and higher and higher and then there's again, this is another one of those areas where we just create new vectors for guilt, right?
That wasn't a problem before, right? Safety didn't include payments to a private school, right? That was not part of safety and it truly isn't part of safety, right? That's not going to make you unsafe. Part of our kids safety now, you know, mental over kids safety, right? And yeah, but that's us imposing that on them, right? My kids never came to me and were like, hey, I would like to go to private school, right? I forced that upon.
My kids would probably be super happy to just be on a bus and selling now and later is honestly not because they need to just because they would enjoy them. Actually, right, stick with that for a second though, but think of how many liabilities we have intentionally created with full knowledge that these consequences, this guilt, like this, this weight would come with it. I mean, building a company is exactly that. There's no version of building a company where like, oh, this will be cool.
I'll have less liabilities. You know what I want? I want a situation where I have nonstop liabilities all the time. I think the fantasy looks something like this. The fantasy is must be awesome that you started a startup. That must mean you're your own boss and you get to make your own calls and you get and I'm like, I think about that. You never. Yeah. Like, I try to remind myself that that sounds cool. If you inventory 99% of the thoughts in my day, they are not about how sweet it is.
I think they are about shit. I've got a lot of liabilities that I got to take care of today. Yeah. There's a lot of stuff to do. Yeah. Yeah. Yeah. Yeah. It's not in the brochure, so to speak. No, but I think it's so inherent to the founder archetype, to the extent that there is one. I think that this whole thing about taking on these new liabilities, we are risk-reward machines. Yeah. We are so tuned into that particular arithmetic that I think that it's hard to avoid. So this is part of it.
Like that was we had safety. We achieved a certain level of safety. We decided to trade some of that safety for private school, because we're looking at that and going, there's a risk there, but there's a reward. Kids will have a better education, better network, better all these things. So that's what we want to achieve for them and that's something we want to give them. And we're willing to take that risk because we believe that the reward is there. And there is, right? But the risk is real.
The risk is, and it's not just the risk of it going away, it's the risk of the pressure it puts on us to maintain it. And I think that that's one of the things that founders are not particularly great at is like understanding what's the theoretical load limit that I have, right? And we don't usually acknowledge it until we pass it. And then things like burnout happen or you know, your heart's stopping and Elliot and I having to drive you to a hospital. And I mean, Jesus, yeah, that's real.
This is what happens, right? And because, you know, we realized that was all panic induced for you, right? It was an anxiety or panic attack. Why? Because of all of the fears and guilt and all of the shit we build up around us because we've taken on more than we should have in that risk reward tolerance that we have that very often goes the wrong way. I agree. And look, when it was paying dividends, right?
When I was basically creating something out of nothing, it created this dopamine hit that's it, oh, working means like I'm less fearful, right? Like if I'm working, if I'm working towards something, in the irony about this is most of the hours that I've ever worked in my life, I didn't actually get paid for. Right? They were like working on the come, right? Like we're working like running into the abyss in hopes that somehow this will pay itself off. But there's this weird thing.
Yep. Start to generate money that I can take some of it some point someday. Right. If I really, really consider it and I said, look, if I take all the cumulative hours that I ever worked toward building startups, right? And spent them toward almost anything that would have just guaranteed pay, I might have been further ahead in the part that just guaranteed pay, just based on the sheer number hours that I was willing to contribute, right?
So it wasn't one of those things where, hey, I was working lots of hours because I knew that I would make all this money, right? Most of it, hell if I knew, all I knew was that if I was willing to work lots of hours, that there was a high probability that I would be able to escape that fear. And so I was constantly on the hamster wheel of escaping fear. Now let's flip it.
Let's talk about later in life where all those things I was setting out to achieve that we were setting out to achieve, right? We did game over, right? We're good. We're past the finish line. It's cool, right? It's way worse now. Don't worry, Will, I painted a new finish line way further ahead for us. Let's run for that one now.
I was talking to a friend of mine and I know he's a listener, so I'm talking to you and we were talking the other night about the other episode we did, the fear agreed episode, right? And he's done extraordinarily well. And I said, what is it for you? Is it fear agreed, right? He's always fear, right? Now I'm terrified of losing it. Yeah, right. Yep. So that's the funny thing. Now when I'm saying, hey, sun walks in, right?
And again, I'm using my sun because it's like the most precious thing, right? It's the one thing, like if I say, oh, I'm working hard because I want to keep my Lamborghini, I don't have Lamborghini. But like, but I want to keep that. You're like, oh, well, you're just a materialistic jerk. But when I explain to you that this same calculus happens when my amazing sun walks in the room, you start to realize that this is a material thing, right? And it's not about greed.
It's not about how much can I earn. It's shit. If I turn to talk to little Will about whatever he has to talk about, right? Like it's probably something idiotic and I love him for it, right? I hope it is. But when I turn to talk to him, I'm doing it at the expense of my safety because when I turn to talk to him, I'm not working on the thing that brings me safety, right? And that's terrifying. And by the way, it's so fucked up. Yeah. Yep. Yeah. Right?
We're not prescribing a plan or a path here, folks. This is a cautionary tale. Yeah. This is exactly that. Yeah. If you haven't figured that one out, it's so crazy though, because in those same moments, right? Like, of course, it goes through your head and it's so fast, right? Because we're so practiced at this, at the, you know, the risk reward, the calculus around, you know, what happens? Less than a second of thought. And all of those things are running through your head, right?
It's like, if I talk to you now, like I can either talk to you, you know, about how long a snail lives is what my son comes in and wants to talk about around how long a snail lives in captivity versus in the wild, making a strong case for keeping them in our home because they live longer than captivity. Yes. So we should have 100 snails in the house, right?
So in that second, he's explaining that to me, I'm thinking, I can either send you to private school or we can have this conversation, right? Which is not entirely true either, right? It's not entirely true. But it's how it feels. But that's how it feels, right? And I'm sure it's the same for you. There is a physical sensation. I get an actual physical feeling in my body when this type of tension starts to appear in life, right?
Where there's this pull from work, which is constantly there and it keeps me grounded pretty much in this seat where you see me sitting right now. If you're watching the video, this podcast, there's a hell of a lot of gravity in this chair. Didn't know that when I bought it. But it keeps me stuck here. Right? Anytime there's this opposing force of somebody trying to pull me away, there's a physical sensation and a discomfort that's created around having to make that decision, right?
And there shouldn't be, right? This is this again, this is not, this is a cautionary tale. This isn't something that you should aspire to. This is something you should try to avoid. And I do. I try to remind myself that that three minutes that he needs to make his pitch around how many snails we should keep in our home versus the three minutes I could spend, you know, finishing that email campaign that isn't going out tomorrow anyways. And yet it's there, right?
It's so hard to lean back and have that perspective and say, not only do I not need to think about this. I thought about it. I certainly don't need to feel guilty about my decision, but it is, it is so hard. It is so hard. And what's amazing to me, I mean, think about this, right? We're doing a podcast about how messed up this is. So it's not like we're not aware, right? It's not like when our son comes in or our wife comes in or whatever that we're unaware of this, right?
We're hyper aware of it, which by the way, makes it 100 times worse because there's nothing worse than knowing what you're doing is so messed up and just doing it anyway because you don't know any part. It's the feeling that I have to imagine that everybody who opens a pack of cigarettes that now have like the skull and crossbones plaster on the front. Perfect. Perfect. That's such a good analogy. But I'm going to do this again. I know this is bad for me, but you know, one more, right?
It's the same thing, right? I know that I shouldn't do. I know that it's not even, it's not even beneficial anymore. I think this is something else we have to address that you said it, right? Earlier, earlier in the career, there were times where there was some necessity out of this. Like we had to be doing something all the time because we were moving from zero to one. Building that momentum, changing inertia is a hell of an act, right?
So if you're going to take a business that doesn't exist, breathe it into life and then make it move forward and get it to some sort of positive traction, that's a gargantuan effort. But at some point, once the momentum has been built, we have to learn how to change your relationship with that. Easier said than done. 100% right? Like quitting smoking. All right? Easier said than done, right? Yeah, it's obvious that we need to do this.
All of the sciences there, all of the evidences there, there are even methods to help you do this. And yet, it's very, very difficult because much in the same way that somebody's addicted to that, that cigarette, we're addicted to that action that got us to where we are and we don't want to go back. And the best answer we have for that is to just keep doing the thing that we've always done without re-examining a situation and saying, do I still need this tool at this time for this job?
And the answer is probably no. But man, if you've been swinging a hammer for 30 years, it's hard to stop swinging the hammer and say, I'm going to have a different relationship with this. It's certainly at least for me and really hard. I'm watching this happen in real time with Summer, my 11 year old daughter, right? Summer is an insane overachiever, right? Academically. She has been an A plus student in every subject for every year.
She's in sixth grade now and she's never gotten anything but an A plus. Like if she gets like on a test, if she gets 48 out of 48, she comes home disappointed because she was like, there's a bonus question I missed it, right? Now here's what's really interesting. Sarah and I don't give a shit about any of this. Now I'm not saying we don't care about our daughter's welfare. I'm like, there is no version even remotely implied that she needs to feel like this about any of this.
And then people like, ah, maybe you don't realize you're doing it. No, we're super hyper aware. And the two of us Sarah and I are comparing notes like, what the hell is this, right? Summer, this summer, when she was off school, she was like, I need to read a minimum of a book a week and maybe two books a week. And we're like, why? She's like, because otherwise I'll fall behind. Okay, first off, who says that, right?
Like what kid is like, I need to read a minimum of two, just self-impose for no reason, right? But I watch it in her. Now I can't figure out where it comes from. Of course, you can do the obvious things. Well, your dad was super, you know, ambitious. So you're being, she has an amazing life that has absolutely zero consequence to it, right? Now, I don't want to diminish her ambition, her emotions, anything like that.
But what I'm saying is, I'm watching her be exactly me on a totally different set of conditions, right? But she is like moniacal about her output, right, about her performance, about, et cetera. And what's interesting, man, is with zero pressure, right? Me and Sarah exert zero pressure on her. If anything, we're the ones trying to tell her to chill out. You don't need to read books while you're on summer vacation. Go be a kid and go play.
But this is one of those, man, it was one of those things where some sage, older, great, grandparent, grandparent, someone, not one of mine, but somebody said, he's like, kids are going to hear 2% of what you tell them, right? You can tell them whatever you want. They're going to hear 2% of it. They're going to do 80% of what they see you do, right? Kids are great mimics, right? And so that's that, right? So summer sees you, right?
And she sees that output matters to you maniacally more than anything else, right? And not just in work, right? Like, she's seen you in that workshop. I've been in that workshop with you. There's a maniacal focus on output there, right? Like we ran that project like we were in a, you know, you'll proud of that. Yeah, amazing. I'm still still happy that that turned out the way it did despite my inputs. I was great. It was great.
But yeah, it's the kind of thing where I think that they observed that. And I think this is part of where this comes from in founder life as well. We get this, you know, like we need one more vector for guilt here. But when we look around and see what we think other founders are doing, we assume, right? Because there's a narrative out there, right? The hustle, crush it, kill it, you know, burn the midnight oil, you know, it's all or nothing. That narrative, we see other people doing that.
And so then we start to copy that as well. Now do we actually see them doing that? Not really. We see them talk about it on Instagram, which is two seconds versus the other 24 hours in a day, but I think that's a big part of it. I think that observation of behavior is a big part of what dictates our own behaviors. If we're for good and for bad, it's funny. You should say that. Talk about like a pace car, right?
Yeah. Over the last 30 years across nine companies, then all the founders that I've worked, I've literally met and spent time with thousands and thousands of founders on paper. And I don't say this questionably, the hardest working people you're ever going to meet, right? Now, when I say hardest working, I just mean without being told they need to work hard, right? Dedication is the word that comes to mind. My stepfather's a landscaper. I did hardcore landscaping on my own property.
If you remember this, years ago, for like six weeks, I just, I just, I just, I just said to you all myself, right? I got involved in that project as well. I broke my, I broke my back with some mulch bags, yep. You did. You did. You're slanging some mulch with me. Yeah. I always appreciated it. But at the end of six weeks, I could barely function. Like physically, I could barely move, right? And I call them a stepdad and I'm like, hey, dad, like, how do you do this? Raise a career landscaper.
He's like, it's easy. I wake up. I'm broke. Yeah, it's good. Yeah. It's like, wow. Hell of a motivator. Yeah, hell of a motivator. But my point is when I say hard work, a little bit of a tangent, but I do want to qualify this. He works hard, like physically hard. I'm not discounting our work, but that is like literally the hardest work I've ever done in my life. So the fact that he wants to do less of those hours makes all the sense in the world. He wants to work 37.5 hours and not 37.5, right?
At all and I get it. When I say we work hard, I mean, motivated in a way where no one told us that we had to do it. We're doing it off of sheer, like just self ambition, motivation, fear in most cases. And we're willing to run ourselves into the ground. Everyone around me, this is going back to thousands of founders of the thousand founders that I know work in sane hours as well. No one has ever said to me, you should work more ever. In other words, I don't have one comment.
Yeah, I don't think I've ever heard of it. I'd be like, you know what? I feel like you could put a bigger dent in that chair in your office. Yeah. I don't think so, man. No, but I mean, what I mean by that is like I've had zero, zero input from anyone in my entire life to say you should work more, right? In other words, it's like it's not like everyone's been pushing me and I'm just like following their lead. He's looking at me like you're insane. What is wrong with you?
By the way, the same way I'm feeling about my daughter right now. I'm like, wait, why are you reading so many books? I'm not against it. I'm obviously it's amazing to watch, but I can't put my finger on it. And all the people around me to your point have been saying the opposite. Like dude, you need to take it down a notch, right? Like come down. And they're all right. And instinctively, I know that instinctively, I know that. Well, I don't change anything. Yeah, can't do anything about it.
Sarah is in Bermuda right now. She's on a trip with the kids and we were talking chatting and she's like, are you sleeping? Now she always says that to me and you know this because I don't sleep very much, right? And I center my fit bit, like my schedule, right? And every day it's like up at 3.30, up at 3.30, up at 3.30. She's like, I take that as a no, right? I'm like, it's not awesome.
And by the way, it's not like my alarm clock's going on and I'm so motivated that I just have to get up at 3.30. Right. Yeah, you're not trying to write a book called the 3.30 Club, right? That's not a thing. I woke up to alarm clock in 30 years. I mean, dude, if I could sleep till 6, it'd feel like sleeping till noon. Yeah, but then it's so bizarre because so much of the day feels like it's gone and then I feel guilty about that.
But my point is like, literally even like subconsciously, my body is waking up and saying, get your ass out of bed, get to work, etc. And I'm not even, buddy, I'm not even solving a problem anymore. No, no, no. Like in other words, like it used to be I got up that early because I had to because like shit had to get done. Yeah, yeah. There's something that needs to get done that will be disastrous if it doesn't. Yeah, you know, I wake up 3.30 this morning, right? Why do I wake?
I have no ability to go back to sleep. Why do I wake? And I'm laying here going, you gotta be kidding me, right? Like the opposite of how motivated you think I am, right? But I'm like, you know, if I'm up, I might as well be getting stuff done, right? So, you know, I'm straight to my computer and I just start banging stuff out. Don't want to waste it. Yeah, yeah, yeah.
Like it wouldn't occur to me to like do what a normal person would be like, maybe get some breakfast or like, I'm a bit, you know, dinner probably at that point, but like get some breakfast or go watch TV or go do literally anything, right? But work and work is the only thing that comes to mind because if I come downstairs and I sit down my computer, I'm like, you know, I'm going to play a video game. You know, I'm a huge gamer, right? That sounds awesome, right?
Kind of makes sense to do it if it's 3.30 in the morning like go play a video game. I'm like, yeah, but these spreadsheets aren't going to solve themselves. No, they're not. They don't. It's amazing how like consistently it just, it just, so my point is it was great for a while and then it became a curse, right? And now when the curse side of it, I'm the curse side of it where work, that part's easy. I'm sure. Right?
The hard part now is trying to get to a point where in my career where I can be okay and not working, if we built so much of our life, so much of our life around this one thing around work and kind of, you know, the fear that we're trying to escape from, etc. And work becomes the one thing that solves for that. That is a problem. No, that sounds obvious when I say it, but man, you try to live it. And look, our work is important. And it's great that we're willing to do what we do.
But at the end of the day, if we can't turn it off and more specifically, if our work doesn't become an actual means to an end, it just becomes the means it's not actually worth doing. So in addition to all the stuff related to founder groups, you've also got full access to everything on startups.com. That includes all of our education tracks, which will be funding, customer acquisition, even how to manage your monthly finances. There's so much stuff in there.
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