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EP98 – The hard truth about bootstrapping startups (Part 2 with Jason Cohen) Episode 98

EP98 – The hard truth about bootstrapping startups (Part 2 with Jason Cohen)

Jason Cohen asks Justin Jackson hard questions about his startup, and what it's going to take to go full-time.

· 01:10:35

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Speaker 1:

Hey, folks. Welcome back to part two of my conversation with Jason Cohen. If part one was, you know, Jason and I kind of, easing into things, setting the stage, part two is really, there's no pretense. We we really get into it. The real raw human experience of bootstrapping, of building a business, of being an entrepreneur, and not just theoretically what that looks like, but what does that mean practically?

Speaker 1:

Practically in a real human life where real human things are happening, you know, at home, where you have a significant other, where you have kids to feed, where you have the the stress and the pressure that's created by, you know, wanting to build this thing from nothing. And I think Jason was really honest and I think I was able to be really honest and open. And, the result is, I hope valuable for all you folks. Before we get into that, a few quick reminders. First of all, Mega Maker, the membership site for bootstrappers that I've run since 2013 is going to be opening up registration again here in December and January.

Speaker 1:

And I know a lot of you folks have been waiting to get in. If that's you, now's the time to sign up. You can go to megamaker.co, and the waiting list is there. Number two, John and I, my partner in Transistor, we're going to be doing a podcast in 2019 program. This is for all of you, especially those of you who work for an employer or have wanted to start a podcast for your business.

Speaker 1:

We are basically starting a concierge service for those of you that really want to succeed with a podcast in 02/2019. You don't wanna just launch it, but you wanna do it right. You want to have weekly instruction. You want to have a private Slack where you can ask questions. That's all going to be happening at podcast2019.com.

Speaker 1:

Go there and sign up, and we'll let you know when we open that up as well. Alright, folks. Been getting a lot of feedback about this. Here is part two of my conversation with Jason Cohen. Of course, like so much of this is me thinking about my situation.

Speaker 1:

And, and this is really what's tricky about all of this advice and even talking about any of this in the comments is that so much of this is colored by our own experience. Right. And also colored by, how we remember things. Also colored by the the time, which is, you know, some of it doesn't matter that you did it in 02/2003, but some of it, like you say, really does.

Speaker 2:

I think you're absolutely right about memory being bad. I agree. Also, goals. In other words, what did I wanna do with SmartBear? The answer is I just wanted, like, to have my own job, and no one tells me what to do.

Speaker 2:

Mhmm. That's literally like, I wanted to make as much money as I could Yeah. And also not deal with anybody. Yeah. That's a pretty negative statement.

Speaker 2:

It's also true. That's what the that's what the deal was. I did wanna go bigger and not at first. Again, I changed during the first kind of eighteen months, which was that transition between bootstrapping and going, you know what? Nevermind.

Speaker 2:

I want to raise money and go big. Part of that was having different goals. Because it is a different set of constraints when you raise money and a different set of goals than bootstrapping. Again, not saying one's better. That's of course false.

Speaker 2:

But, but they're, they are different. That's for dang sure. You have different goals and different tools to go after that. And I did want a different sort of journey this fourth time around. And so, so it was, I didn't even want to be CEO forever.

Speaker 2:

And I did, I wasn't, I was a CEO for four years and then, and then changed. And so for the last five years, I've not been the CEO of my own company, which has been fantastic. But in the smart bear days, the previous days, that would have sounded like hell, and it would have been hell. Because, again, like, I was a different person or I I had different goals, etcetera. So all those things you said about advice, totally agree.

Speaker 2:

I'd add more to it. And one of the big ones is goals. And so I really feel like when people give advice, what they really are doing is giving themselves advice, which is too bad because they're not usually paying attention to you, the person asking for advice. So, like, to me, if you ask for advice on something and the first thing they do is start telling you what to do, they're not giving you advice because they didn't like, the first thing they should do is ask you questions for an hour. Yeah.

Speaker 2:

But, so what are you trying to get out of this? Like, what does good look like? Not like we're gonna be in five years. That's too weird. But, like, do you wanna never have employees?

Speaker 2:

Because that's really because the employee sucks. Like, it's it's a lot of work. It's hard to deal with people. And what if they don't do well? And what if they do?

Speaker 2:

And oh my god. Like, oh, for a lot of people, like, I never want that. Like, great. Great. Great.

Speaker 2:

Great. Or maybe you do. Maybe you wanna make the biggest company ever. Maybe you don't. Maybe you wanna, like, maybe you wanna be famous.

Speaker 2:

Maybe being famous doesn't matter. Maybe you wanna make the most money, maybe not or maybe there's a stack rank of that. What is your previous blah blah blah blah blah. Like, that is a pre conversation that to me is mandatory before someone can actually even have a chance of giving advice. They can still ignore all of that, of course.

Speaker 2:

But at least they're interested. And so hopefully, hopefully, the advice is tuned or they're trying to tune the advice to those things. It'd be like being a tennis coach because the coach never looks at you. They just tell you things about tennis. Like, that's not what a coach does.

Speaker 2:

So I feel like good advice could exist, but very, very rarely and certainly not on Twitter.

Speaker 1:

Yeah.

Speaker 2:

Which an accident. It is good advice for you, but it's an accident. It just so happens that their goals and experience and luck and blah blah blah, all those things happen to line up. So actually it is, but how would you know?

Speaker 1:

Yes. Yeah. Well, and that's the tricky part. I I often say you can't split test experience. And so even, even if someone did succeed, we can't go back and then do a multivariate test and say, but if they had, you know so it's tricky.

Speaker 2:

Yeah. And it's worse. Like, one of my more popular posts, as you pointed out, because I've been writing for a long time now, because the blog was popular eight years ago when I started WP Engine. So it's been a long time. Yeah.

Speaker 2:

One of my more popular ones is about survivor bias. You know, people have a success maybe too like me. Then they have a blog where they tell people how to how to run companies like me. And then and then but what does it mean? Like, are you sure that's real, or did you get lucky twice?

Speaker 2:

That's I mean, with, with everyone in the world trying to make businesses, of course you're going to get lucky. You know, there's a lot of people that are gonna get lucky a couple of times. So who cares? So at the very minimum, have to ask, okay, you made this choice. You had these goals.

Speaker 2:

You had, you, you held these things to be important. You had this strategy, etcetera. Did other people more or less do the same thing and fail a lot? Because if so, it doesn't mean that's bad advice. You may need to do those things just to have a shot.

Speaker 2:

Mhmm. You know? It's okay. It just doesn't mean success because if it's just as correlated with failure, who cares? And and they're actually and I put this in that post.

Speaker 2:

There are books about there's this book called Good to Grape by Jim Collins, and it's a very famous business book. It's a bestseller. Everyone quotes it. And what they did is they pill they they picked out 11 companies that really outperformed a long term on all these metrics, yada yada yada, and asked, hey. What makes these companies so great?

Speaker 2:

And they interviewed the CEOs, and they and they came up with this thing. It's about culture and this and performance, but this is what we mean by performance and all this stuff. And the idea is this is the formula at least the let's say let's say a framework or a guide to excellence. The problem is that five years later, forty percent of those companies were bankrupt. So number one, oh, wait.

Speaker 2:

Whoops. Yeah. Hold on. And also, like, when you go ask, well, what about other, say, public companies just to pick another cohort? Do they not do this?

Speaker 2:

And it turns out, no. They do that too. They do a lot of those things too. They say a lot of things too.

Speaker 1:

Yes. It's just like,

Speaker 2:

oh, so none of this really matters at all. This is just stuff people do Yep. Largely. So that's an example of what I mean, by that survivor bias. We're we're we're looking only at the good and not asking, but it but it's the same there.

Speaker 2:

So you're actually absolutely right. Of course, you can't run it twice. That's that's right. You can try to ask, okay. But I'll look at this whole cohort versus this whole cohort, even though they're different companies.

Speaker 2:

In my experience, that doesn't tell you very much because it turns out stuff isn't correlated that well. And then I prove my final proof of that is the whole job of a venture capitalist is to identify companies that will be really successful. Yeah. And they can't. That's why most of the companies in their portfolio at any given time don't.

Speaker 2:

Yeah. And and also only 25% of any venture capital firm ever makes money. That's really, really bad. In other but they're smart. They're not stupid.

Speaker 2:

They're really smart. They do nothing but try to figure this out all day for for decades. And they're super smart, and yet they can they almost can't do it at all. So what that tells me is, there's not a formula. Stop it.

Speaker 2:

Stop it. That's not the case. What you can do is say, alright. What are my abilities? What are the things I love?

Speaker 2:

What are the things I wanna learn? What can I bring? What are my ideas? Can I try to be as honest as possible about, is this resonating with customers? How's things going?

Speaker 2:

Blah blah blah. Really try not to confuse myself, try not to lie to myself. It's very hard because we all want things to succeed, but try. And when it comes to advice, I think what you do is you say, number one, what are the goals, motivations, context, etcetera, of the person giving advice? Mhmm.

Speaker 2:

Do I think that matches to me enough? This is not perfection, but enough. And if the answer is no, then never mind. It could still be good advice, but who knows? So just avoid.

Speaker 2:

Yes. On the other hand, if you're like, yeah. No. This person's kinda like me. They got started the way I'm getting started.

Speaker 2:

They're in the same kind of a building same kind of product. Mhmm. And also I think they're just smart. Then okay. Like like so try to match it up since they can't do it for you.

Speaker 2:

And then another thing I'd say is it's okay to sort of ask, does this just resonate with how I feel? Like, we tend not to wanna do that. But I think it is okay. And the reason is if it's really true that all this advice is actually fine, there's people who say never use Twitter. It's a waste of time.

Speaker 2:

They're probably right. There's people that say, I built my whole business by building a following on Twitter. They're probably right. Mhmm. So if if all of this can work, why shouldn't you choose based on what you're excited about?

Speaker 2:

If all of them are equally smart Mhmm. Equally good ideas, more or less, or at least you can't choose one, the the good or from the bad. Yeah. Why not pick the one that you're personally really jazzed about? Because whatever you're jazzed about, you're going automatically to put in that extra energy and that time, and you'll wake up at two in the morning thinking about it and blah blah blah blah.

Speaker 2:

You are going to do that. And you know what? If a and b are both pretty much good ideas, but one you're jazzed about, which one are you gonna kill more likely?

Speaker 1:

Yeah.

Speaker 2:

The one you're jazzed about. So Yeah. As weird as it is to say go with what excites you, not your not not follow your passion. That's bull that's crap. Yeah.

Speaker 2:

But the thing about like, oh, I can't pick between this advice. Going with the thing that you just really jazzed you up, that is my logical reasoning why. That's not the worst way to pick it.

Speaker 1:

Yeah. And, obviously, there's tension between all of these ideas. Like, there is, on one hand, this is true. Like if if I am more excited about and let me rephrase what you just said and see if I'm understanding. If I am more excited about a specific group of customers and a specific idea and a even a specific way of building that company culturally, ideologically.

Speaker 1:

Theoretically, if I go head to head with somebody who is not as excited, I have a better chance of winning. Is that true?

Speaker 2:

I would put it more like you have a chance at succeeding doing your thing. I don't I don't really I understand the competitive mode. Mhmm. And, when I do StrengthsFinder, my third biggest one is competitive. So I absolutely identify with that.

Speaker 2:

Mhmm. But I actually think that's probably the wrong way to to plan things. How will I beat them is probably the wrong mode. The right mode is probably how do I build a product I'm incredibly proud of, and can I find customers who are super excited about whatever the heck I built for whatever reason? Mhmm.

Speaker 2:

And it could come from a lot of different places. Like, there are products that are not very good, but the company itself, its character, the, the way it expresses itself actually, 37 Singles is a good example where early on the product is not good. Mhmm. And in fact, all the other products they built were so bad that they abandoned them because they weren't good. Yeah.

Speaker 2:

But, man, do people love the company, and they should. Yeah. They should. It is I mean, the the contributions they've made to to the debate and and the ideas they have and how well they are how how well they do it and the and the inspiration to give people, that's all very real. Yeah.

Speaker 2:

Why not buy a product on that basis? I bought Fog Bugs from Joel Spolsky back in the day because I loved his blog, not because it was the best bug track bug tracking solver. No one would tell you that's the best bug tracking solver, but I did it. That's perfectly valid. So what I'm saying is when I say the bet you know, be the best for people, it can mean so many things.

Speaker 2:

Patagonia, like, it probably does have good stuff. But mostly it's because, my god, that company, the culture, what they do for the for wildlife and stuff. I mean, it's company policy that if you get arrested for protesting something with the environment, they will bail you out of jail. That's how much they believe in that. Right?

Speaker 2:

So so, like, is that a reason to buy? Hell yeah. It is. Of course it is. So it can be features.

Speaker 2:

It can be the product. It can be the culture. It can be the purpose. I mean, it can be a lot of things. Let's not box it into one thing it can be.

Speaker 2:

Yeah. But let's let's put a let's let's call those things like a really great reason for people to get excited about buying that product. It could be just it's the best product. That's Google. I don't give a crap about Google, but it was the best in two it was simply the best.

Speaker 2:

So it can be the best product. That's cool too. So there's so many ways. But I would say forget the forget forget the competition. Mhmm.

Speaker 2:

I bought you know, you buy from Patagonia because they're great, not because I don't even know who the competition is. You you're not not buying this other one. You're buying Patagonia. So, like, I think that is positive, strong. That's your own story, your own narrative, your own value, what you're doing.

Speaker 2:

I say focus on it. Of course, this competition matters. You gotta look. You might feature compete. You might lose to them on certain features.

Speaker 2:

So you have to make the feature obviously operationally. Yes. You have to care about competitors. But ultimately, like you can't build a company by by a, like, well, here's how we're not this other person. You have to decide who you are and kill it.

Speaker 2:

And so that's why I say the things, if you pick the things where you're like, yeah, that that's great. That's because that's going to be you killing it as opposed to I'll be better than someone else who maybe isn't as passionate. Look, most entrepreneurs are passionate. I don't let's not have a passion war. Let's just say you should do the things that you, where you happen to be energetic and fulfilled at because that is the best you.

Speaker 2:

And that's what you need be is just the best you and the best organization, period, regardless of whether what comp competitors are doing.

Speaker 1:

Yeah. And so let's so let's keep fleshing that out a little bit. The because one of the things I've always appreciated about you, you used to have this podcast. I don't know if you still do, but you used to have this podcast where often people would come to you with ideas and you were kind of like the the bad medicine man. Oh, that

Speaker 2:

was so fun.

Speaker 1:

I will give you the medicine.

Speaker 2:

I'll tell you what I called it. It was Doctor. Laura for Startups.

Speaker 1:

Doctor. Laura for Startups. Yes.

Speaker 2:

And here's why I called it that because because I figured I'd be giving the same advice all the time because how many ideas can I have anyway? Mhmm. And and, you know but but it's so fun anyway. Like like, listen to doctor Laura and, like, people call up and you're like, oh, what a crazy person. Doctor Laura's gonna tell him whatever, you know?

Speaker 2:

And you're probably right. But it's so fun to know what she's gonna say. Like, you don't even care that it's a thousandth time and you even know what she's gonna say. It's still fun. So I thought maybe it'd be like that.

Speaker 2:

I only stopped because of time. It just, with WP Engine starting to take off, I just had no time for anything extra. But, yeah, that was fun. It was well, the other thing is I do tend to do that when people actually, this happened in our Twitter thread, but I don't I don't I'm not saying this is a good thing, but it is a pattern. My normal mode is people say, oh, look, I have this idea.

Speaker 2:

I have this company. I do pitch practice all the time with companies here in Austin with Capital Factory. Yes. Here's my pitch. And and my first reaction is just to shred it.

Speaker 2:

Like Mhmm. This is wrong. That's bad. And I'm not convinced about this and this. And of course, that's terrible.

Speaker 2:

I shouldn't do that. But but it's honest and it's direct. And then this is the difference. And then it's like, now I think this is a fantastic idea and a fantastic business. The reason I think what you just did sucks is that I think there's incredible things here and you're not telling me those things, but I can see them.

Speaker 2:

Like this isn't a product just to organize how how let me let me think. I don't really want to call anyone out, but let's just say this is not just a product that allows people to do this and that online. The reason people want to do this particular thing online is because they want an income stream. Why do they want that? Because maybe they want to quit their shitty job and be their own boss.

Speaker 2:

Even if they're making less money, maybe they just need money on the side. Maybe they're a single parent and they need that money. Maybe they're staying at home and they need purpose. Maybe they're an artist and they've always wanna do this, and this is a way to finally get art together with money, which is so hard. This is changing people's lives for real.

Speaker 2:

Maybe they're in a country where it's too hard to do that, but because it's online, they can do it. This is this is the re the real changing people's lives, not the stupid Silicon Valley where I have a lot of people look in my apps when I'm changing lives. No. Yeah. Just one person who gets that extra thousand dollars a month, and so they can do this instead of that, it it it can transform it.

Speaker 2:

That is what you're doing. And all you told me about was some feature about how someone can resize an image on a goddamn website. So I've shred them not because they're they're bad, obviously, but because, like, no. This is amazing. I should be, like, giving you money philanthropically so that you do this for people because I really feel like that's what you're doing.

Speaker 2:

So in other words, maybe I'm I'm too harsh when I tear it down, but only because I wanna fill it back up with something that's that's hopefully, like, just more compelling and and or or better. Or maybe there are some some particular points that are a problem. Yeah. You gotta put your finger on it and be honest so that you can go solve it, not so you can quit. Yes.

Speaker 2:

This you can go, oh, this is the thing I need to work on. Everyone And else told me this is hear all the time. Everyone else told me my idea was good. You were the only one who said, well, I see three problems. And each time, it's like, now this isn't necessarily a deal breaker because you could do a, you could do b.

Speaker 2:

You probably have a better idea than a or b. But you can't do I feel like you can't do nothing about it.

Speaker 1:

Think you

Speaker 2:

need perspective about it. So you should stop, but I think you kinda need an answer here. Yes. So, you know, that's totally different than just you know? So anyway but I'm probably too harsh, but I think it has to be followed up with with that.

Speaker 2:

That's by the way, that's what I think good advice looks like as well.

Speaker 1:

Yeah. The and, man, there's a a lot of threads I wanna pull on there because you really got fired up just now. In Like, terms of, especially when you were talking about changing people's lives. Yeah. And, man, I just because I I'm gonna spell out the threads and then we'll cover them one by one.

Speaker 2:

So one Okay.

Speaker 1:

Thread is you could be changing people's lives, but as you said on Twitter, if after three years you're only making $20,000 a

Speaker 2:

year Right.

Speaker 1:

That's probably not going to be enough realistically for you to make a living. And so we just need to address that.

Speaker 2:

Right.

Speaker 1:

Pragmatically.

Speaker 2:

Right.

Speaker 1:

So that's one third. Let's just keep that there. The second thought I have is because now WP Engine to me, I don't know all the customers you serve, but I know that right now you kind of have this image of being for kinda enterprise y or companies. You know, these are people that are they're these aren't like Jason Cohen solo blogger, although you have some of those folks.

Speaker 2:

Yeah. We we do that too.

Speaker 1:

And so I'm wondering

Speaker 2:

We're cheaper now than we were when we launched. Mean, I had those people at $50 a month. Now the cheapest is 35. So, yeah, we still have that.

Speaker 1:

So, and, unfortunately, all of these things splinter into new threads. But Right. Initially, when you're building WP Engine, were you just excited about other people like you that had blogs? Or were you excited about that, you know, 300 person company that was gonna use WordPress as their CMS? Because did they both fire you up in terms of changing lives, or did that change over time?

Speaker 2:

It changed over time. Originally, what I was excited about is, oh, look. Someone will pay me for this.

Speaker 1:

Yes. That was it.

Speaker 2:

Don't care if I'm changing their life. Like, you know, I wish I could say that I was I felt that way. But, you know, if you're being honest, like, sweet. This is really, like, resonating from a product market fit perspective. Holy crap.

Speaker 2:

This is so needed. Yeah. And what I really liked was the, engineering. Yeah. It was fun to optimize and secure and and cash.

Speaker 2:

For me personally, of course, for me personally, that that was really fun. So here I get to work on what I find to be interesting engineering problems, and people really need it. Like, really, like, they're they're it's like it's too easy almost to get new customers, which is an indication that, like, oh, you've hit on something. Yeah. So I just felt like this is gonna be a great little company.

Speaker 2:

Yeah. Again, it took about eighteen months, maybe longer for me to change. I mean, how I felt about it now, not that people didn't sign up. In fact, were signing more and more. That was part of the, actually, the impulse to go, do I only care about making money and working on that?

Speaker 2:

Yeah. Because some of this other stuff, some of the stuff that is happening, you know, the small business owners and they're able to have sites that they couldn't before they were losing money or, you know, there's a million stories sort of like what I was just saying about, of course, I was thinking of somebody else, but, and I'm not trying to, you know, sell w management or anything right now, but, but, but, you know, someone saying something like, yeah, like, like we had a customer made her own guitars and sold them and, she got big press and she got a bunch of traffic and a site crash that should have been her biggest sales day ever. And instead it wasn't. And so we got her up. She got another big sales day and it was her biggest sales day ever.

Speaker 2:

To this day, we have one of her guitars up in the support area because she sent one to our support team for helping her to do all that stuff. You know, that that is changing lives, like in the same way as I was saying. Right? So that is really exciting. So as you start seeing stuff like that we're we're big brands.

Speaker 2:

That's cool too. And also the other employees, not just our customers is what we do for employees. A third of our employees don't have a college education, which is unusual for a high-tech company. Half our half of our executive team are women. We have a whole lot of diversity in all sorts of dimensions.

Speaker 2:

And yes, we look because if you're not looking, then you don't know and and you can't claim that you're that you care, number one, or that you're trying to do something about it, number two. Yeah. So actually, have we have really great numbers in various ways like that. Like, these are ways in which you really can open the door for folks. And, you know, of course, you don't wanna you can you need to open the door.

Speaker 2:

Other people have to walk through the door. Like, you have to earn it. Yeah. But for a lot of people in in most companies, the door is not open. Yeah.

Speaker 2:

And and and that's not okay. And so to do that and you see when you see, for example, people who are clearly being their true selves at work. Mhmm. That I mean, again, you can't really you can't overstate how important that is and how much of an impact that is. Mhmm.

Speaker 2:

Or like I don't know. We do we like we well, anyway, there's a lot of examples. But

Speaker 1:

those are kind of things

Speaker 2:

that matters. And so when I started seeing a little bit of that, it kinda changed like, wait a minute. What can what is fulfilling to do at this point? Again, and also at this point in my life, career, blah blah blah, know, whatever. All kinds of things together.

Speaker 1:

Yeah. I like that perspective because initially, you said it was just exciting seeing someone pay you.

Speaker 2:

Right. It was.

Speaker 1:

And and it was by the way, was that just as exhilarating with WP Engine, you know, your second round as it was with the SmartBear?

Speaker 2:

Yep.

Speaker 1:

Okay. So when when these people started paying also as an aside, I pragmatically, I'm kinda surprised WP Engine worked in a way because to me, like, you were gonna say, I'm gonna reach out to all these solo bloggers and some of them make money and some of them don't, and I'm gonna charge them $50 a month and they're gonna pay me for it, I would say, well, you might be able to get them for a few months, but they're gonna turn out. Like, that's not a good customer group.

Speaker 2:

Solo solo blogging is not was never the primary Okay.

Speaker 1:

Were always going after businesses?

Speaker 2:

Yeah. There's a few successful bloggers who were okay. Fine. But no. No.

Speaker 2:

No. No. It's it was it was typically actually a freelancer who would build sites for folks and but they build it for them and put it on the GoDaddy's of the world or the Bluehost of the world. Mhmm. It's cheap, but, like, sites get hacked.

Speaker 2:

They they're slow. Google will rank you lower if it's slow. So customers notice that because their SEO person told them to make their site faster. So they tell their their freelancer to make the site faster. The freelancer's like, I don't know.

Speaker 2:

You're, you know, you're one of the 3,000 on this machine. I don't even know. Right? Like, so there was different there was different modalities. Sometimes so sometimes the SEO person here says your site's slow, so you you need to find something faster, now you're willing to pay.

Speaker 2:

Yeah. Another modality was I got a load of traffic. My site went down. I never want that to happen again. Yeah.

Speaker 2:

Another modality was I got hacked and never want that to happen again. Yes. So in other words, usually there was some kind of triggering event either through a freelancer or or direct where someone's like, okay. Now I'm ready to spend 50 instead of $5 a month because I now see the value. So usually there was a triggering event or a freelancer who's like, I'm gonna, you know, make sure my clients are on the right thing to begin with.

Speaker 1:

Yeah. And incidentally, is, I think I've been a WP Engine customer for five or six years. Can't remember.

Speaker 2:

Oh, wow.

Speaker 1:

That's Part of the trigger was I was writing things on my blog that were getting to Hacker News, every time it happened, it killed me. But the thing that pushed me over the edge was I built a site for my dad, for his organization. And there's five people using this site and adding plug ins. And the third time I had to go in and remove all the malware, I said, That's it. This is killing me.

Speaker 1:

Yeah. And so, you know, to this day, that site's on WP Engine because of that. Okay. In this final how many do you have four minutes left, or how many minutes do you have left? Let

Speaker 2:

me see.

Speaker 1:

It's ten fifty six.

Speaker 2:

Yeah. Oh, I'm I'm actually don't have a hard stop, so I can do whatever.

Speaker 1:

Okay. Perfect. So because I want I want to, maybe do a little bit of Jason Cohen's Doctor. Laura show right now with Transistor.

Speaker 2:

That's gonna get nasty.

Speaker 1:

Oh, wow. You're already you're ready to gear it up. So the I'll explain briefly where we're at right now. We launched So John and I got together in January. The reason I was interested in this is because he had one customer already, which was Cards Against Humanity.

Speaker 2:

Oh.

Speaker 1:

And I thought I had noticed this trend. You know, I've been a podcaster since 02/2012. I'd noticed I always thought podcasters were a terrible market because they're very DIY.

Speaker 2:

Right.

Speaker 1:

Hobbyists, you got a Dungeons and Dragons show. You're not gonna pay a lot of money for that. But I noticed this trend. A few things kinda culminating. Basecamp has a show.

Speaker 1:

CodePen has a show. A lot of WordPress shops have a show. And then Cards Against Humanity wants a show. Yeah. And they hired two people.

Speaker 1:

And they might be an outlier, but they hired two people full time to work on this show. At the same time, all of this media is coming out about ad rates. We thought that Apple released a bunch of new analytics that showed they were going to release a bunch of analytics. And everyone thought these high CPMs that podcasts are getting are gonna go away. Because we're gonna get the real data, and then people are gonna know.

Speaker 1:

But Apple's data came out, and it was all positive. This these people that listen to podcasts listen almost to the entire thing. They don't skip ads. They're very you know, they're dedicated to the shows they listen to, all those things. And I had personally experienced the power of earning an audience's trust through this medium that is very kind of intimate and you build the listeners build a relationship with the host.

Speaker 1:

Yeah. And I'd seen how from my own little business selling online courses, it had been meaningfully impacted revenue when I asked customers how they heard. So John and I get together, we start working on this thing, and we launched in August, and now it's December. I'm gonna go off the top of my head. I think we're at $4,300, $4,200 in MRR, and about 220 customers.

Speaker 1:

And That's good. Well, that this is what we're trying to figure out. So the

Speaker 2:

It's good.

Speaker 1:

Okay. Okay. This is over. Thanks everybody. So part of me when I was writing when I wrote that tweet and I and when I wrote that blog post, part of my context is, Okay.

Speaker 1:

It looks like there's something here. And I've had some other people check those numbers too. You know, I had Josh Pigford look at them and Rob Walling and Nathan Barry and Ruben Gammes. And so far, say they say you're not it's not like you've hit a grand slam home run, but these numbers look good.

Speaker 2:

Yeah. That's what I said.

Speaker 1:

And the the crossroads though, and I think it's it's common for a lot of bootstrappers is what do I do now? Because this is really hard.

Speaker 2:

Yeah.

Speaker 1:

I'm I'm just plugging away.

Speaker 2:

Yeah.

Speaker 1:

And I thought, you know, maybe my online course business is gonna help fund this thing. John's working full time for Cards Against Humanity. And so the thought is, what do we do now? And part of my thinking with that tweet

Speaker 2:

I don't understand why now is a decision point. What's thinking now a decision point? Like, why not do what you did yesterday?

Speaker 1:

Because I don't know how much longer I can go.

Speaker 2:

Oh, you're you're burning up.

Speaker 1:

I'm burning up. Yeah. So the the and so my constraint would be money, and John's constraint would be time.

Speaker 2:

Oh, why don't you trade?

Speaker 1:

Well, we maybe we should. I'll just go work for Cards Against Humanity for a while. Then and and so part of me was thinking maybe I should just, you know, go get a job or do some consulting. Those are both options. And grow this on the side.

Speaker 1:

And, you know, ten, fifteen hours a week. That's

Speaker 2:

one a week have you been spending?

Speaker 1:

I mean, it's hard to say because I'm pretty excited about it. My problem is I wake up every day with a blank slate. So I can go and try to make run over here and make some money, or I can answer a bunch of people in support and I can reach out to people and I can, you know, Ruben Gammes sends me this idea for SEO and I can write a blog post that fits.

Speaker 2:

So sixty hours a week?

Speaker 1:

Don't think it's sixty. No. I've got four kids too. So that's the other constraint on my side.

Speaker 2:

Yeah.

Speaker 1:

I would say it's probably three hours a day that I'm spending right now.

Speaker 2:

Why is that burning you up? That sounds easy.

Speaker 1:

I've heard that the that the the biggest thing that you get like, the the CEO's biggest job is thinking, is having brain space to focus on the business.

Speaker 2:

Yeah. You're not there yet. You just need to get more money.

Speaker 1:

You just think I need to get more money?

Speaker 2:

Yeah. You need to just get more customers. You're the place where you're thinking big strategy.

Speaker 1:

So would it be

Speaker 2:

There's not even one person working on the company full time. So there's nothing even if you had the best strategy in the world, what are you gonna do with it? Nothing. So I think right now, you just need to get some customers.

Speaker 1:

And so do you think I should just keep limping along?

Speaker 2:

You're not limping. You went from zero to 4,300 in three months.

Speaker 1:

Oh, I mean, that that part is good.

Speaker 2:

What do you do with the rest of the time? Three hours a day on this. Yeah. So that's like really small. So what do you do the rest of the time?

Speaker 1:

The other five hours oh, man. It would be actually interesting to know how much

Speaker 2:

than five other hours. What do you do at the time?

Speaker 1:

Well, the rest of the time, I'm home. I'm here at the office from like 08:30 till five. And then I'm home.

Speaker 2:

What what are you doing?

Speaker 1:

Taking care of four kids. Taking them No.

Speaker 2:

No. From 08:30 to five, you're in the office.

Speaker 1:

Oh, yeah.

Speaker 2:

And only three of that is this. So what's that? Rest of rest?

Speaker 1:

Yeah. The rest of it is is kind of doing running a sale for the courses.

Speaker 2:

Oh, running the course business. Yeah. Okay.

Speaker 1:

And yeah. So, I mean, I could keep doing that. The problem is the course business is very launch based. So for this past year, I did not launch anything new. I just kind of went off the old stuff and really to like the people that are good at this dedicate a full year to making a course.

Speaker 1:

And it's like their full time focus. And then they launch and then their back catalog is 30% of revenue. But it's the new stuff that makes money. And so I could do that, but that it just feels like I would really have to focus my brain on just that. And part of my thinking is, oh, I wonder if, like, maybe we should just raise a little bit of money.

Speaker 2:

That would be hard.

Speaker 1:

And do it. You think hard in the sense of, like, now there's earnest capital. Now there's tiny seed. There's places that will fund bootstrappers.

Speaker 2:

Yeah.

Speaker 1:

Hard in the sense of it would be hard to get the money or hard in the sense of?

Speaker 2:

Well, those sources would be good. Yeah. Like you said, like you were just doing, you can count them on one hand. So if one of them will do it, that's good. And if not, then then it'll be really hard.

Speaker 2:

But that's a good that's a good place to that's that's a good thing to think about. Does so the online courses make a lot of money?

Speaker 1:

So 2,017, I probably did $200,000 in revenue.

Speaker 2:

Well, that's good. So This

Speaker 1:

past year, though, gonna it was down.

Speaker 2:

Well, you were working on other stuff. Maybe you could get someone to help, run the courses.

Speaker 1:

Yeah. That it's so again, it's very personality brand based.

Speaker 2:

Oh, yeah. Yeah. That's always hard.

Speaker 1:

Yeah. So I'm I'm which is part of what I wanna get out of it. It's like the there's nothing I can sell. I I can't sell this asset to someone else. Yeah.

Speaker 1:

Yeah. I also can't get someone else to play me on television. You know? I I have to be it's either me

Speaker 2:

or Let me push back on that a little bit. So there's a lot of content that has to be you. But you said a lot of it is like, oh, I gotta make sales and and do all kinds of stuff that sounds very operational that doesn't have to be you.

Speaker 1:

Mhmm. It just feels like in order to make a especially if courses really lose their value over time, then I have really lost a lot of value. And to of a sudden, to kick start that again means I'm gonna have to invest a bunch more time into a new product that, you know, may or may not make a bunch of money.

Speaker 2:

So you're saying you don't no matter what, you don't wanna keep doing the courses? That's just not an option.

Speaker 1:

I wanna get out of the course business gradually. Yeah. But I could I mean, I do have other options. I could I could just go and do consulting. I could, you know but these are the same things that all bootstrappers are thinking.

Speaker 1:

I'm at $4,000 a month. It's not enough to support the family.

Speaker 2:

Right.

Speaker 1:

What do I do?

Speaker 2:

And Well, you just said it. You know what the choices are. It's like I what's funny is this is why it's so infuriating when when you have people online saying like, oh, what you do is you just work on it for ten hours a week and and screw off the rest of the time. It's like, nope. That's not true.

Speaker 2:

Yeah. That's not how that works.

Speaker 1:

Yep.

Speaker 2:

No. And by the way, if you have even if you just have a regular old salary job because that's the least stressful thing to do

Speaker 1:

Yes.

Speaker 2:

Cause the problem with the consulting is it's it's spiky. You get a lot of money and then not. And when it spikes, it's very hard to spend time on on the product because the hourly always wins.

Speaker 1:

Yeah.

Speaker 2:

So it's it's difficult. And then and then when the hourly drops and you could work on the product, you're all stressed out because no money's coming in. You have kids to feed. Yeah. So so it's it I'm not saying it's a bad thing.

Speaker 2:

I'm just saying that's the roller coaster that that is. It's hard. It's emotionally difficult Yes. To do to do that. So the less emotionally difficult thing is you get a salary job because then you know what when that paycheck's coming every month, and that that part of your brain goes, I'm not worried about feeding the family, and that's good.

Speaker 2:

That's that's a healthy thing. Since this whole thing is stressful, it can be nice to, again, sort of put some of the stress to bed in a certain way. That can be good. Yeah. But then there's no such thing as not working like crazy because okay.

Speaker 2:

What's the minimum amount of time you could possibly spend on this? And, you know, ten hours a week is just not gonna do it. Yeah. And scientists don't believe that. I mean, maybe you could say it is, but I bet you do more than that.

Speaker 2:

Yeah. And doing even less than that is not how you get something off the ground. And so okay. Well, if I have a job that's forty hours a week, and then you're doing this and it's twenty hours a week, that's sixty hours a week. And by the way, there's kids and family, and that takes another at least forty hours a week you wouldn't think you would want.

Speaker 2:

I'm counting weekends, obviously. And so that is 100% of the time. And really not all of those are gonna be successful. Like you're not gonna be that successful at the job or you're gonna neglect your family.

Speaker 1:

Yes.

Speaker 2:

Or the startups just not gonna get the attention and that it deserves. So, I mean, just like you said a little while ago, which is I'm really passionate about this. So I I wake up thinking about it and everything. Exactly. That's why it's not three hours a day.

Speaker 2:

It's not compartmentalized into this. I'll just do it one hour a day in the morning, and then I'll stop thinking about it. Yeah. I do not believe you. Yeah.

Speaker 2:

Because you're passionate about it, and you and you work on it in your head, and you work on it in practice more than that.

Speaker 1:

Hold on. Let me bring my wife into this conversation here. We'll see if Yeah. She

Speaker 2:

Exactly. So, again, I just don't believe that. It's fine to say it's not true

Speaker 1:

Yeah.

Speaker 2:

For most people. For most people. Right? So so where does that leave you? And it's like, well, if you bootstrap, it means working all the time.

Speaker 1:

Mhmm.

Speaker 2:

Because you have to feed whoever, yourself, etcetera. Yeah. And you're making an entire company. Yes. So that's all the time.

Speaker 2:

We're done with with your time. We've allocated it. Yeah. That's the answer. But it's really hard on me to burn out.

Speaker 2:

I know. That's why that's one big reason why they fail is because people simply stop because it's hard. Yes. So that's right. It's freaking hard.

Speaker 2:

Correct. Yeah. And again, like, I'm I'm trying to find, like, there's a lot of, you know, there's a lot of lure around certain companies where that wasn't the case. Yeah. But for every one of those, I can give you a 100 where that is exactly the case.

Speaker 2:

Mhmm. Was really, really, really hard. Yes. Until finally, it wasn't a long time after that. That is the normal mode.

Speaker 2:

Now another mode is raise money. Yeah. And as you said, there's new modes that are not that are not Sequoia Capital. Yeah. Oh, good.

Speaker 2:

They're still raising money. Yeah. It's just there's there's other modes that are probably better for the bootstrap, mentality. Great. You know?

Speaker 2:

The exactly. That's the more the better. The more modes there are, the better. Yes. This is another mode is you say, okay.

Speaker 2:

Instead of paying for this in a sense through destroying my waking hours

Speaker 1:

Yeah.

Speaker 2:

I will instead pay for this by working with another group, a group that hopefully you like and hopefully will give you good advice. They're certainly gonna give you money and controlling a piece of the company and so forth. And you say, I know. I know. But the alternative is and doing consulting work, which again is not not a bad idea.

Speaker 2:

It just comes with the it just comes with the kind of up and down and having to manage that, going, getting clients like it's, it's a lot of work and you have to rest. It's okay. It's just that's that, that mode there's the salary mode and there's the, and where you're working constantly. And then there's the, and then there's a raising money mode where someone else puts in the money and but you it comes with them

Speaker 1:

Yeah. In

Speaker 2:

terms of upside and advice and control and all the things that it comes

Speaker 1:

Yeah. I mean, this is Yes.

Speaker 2:

Those are the choices. They're all they all cost you in some fashion. And and

Speaker 1:

so what is your decision making matrix? When you're deciding, okay. Like, there's there's a good decision here, there's a better decision, there's the best decision, what do you per how do you because part of me initially, when I heard about Earnest Capital, everyone else that knows about these things and is smarter than me, they say, Justin, that money is incredible because they'll give you a 100 to 200 k. Yeah. And then they want a three to five x earn out, but they don't take any equity.

Speaker 2:

Yeah.

Speaker 1:

To me, I'm just like, man, that means I have to pay out $500 at some point. And that seems crazy. But

Speaker 2:

No. It doesn't. That's not what that means.

Speaker 1:

What do you mean?

Speaker 2:

No. They only get that if the company sells for a lot more than that.

Speaker 1:

They only get well, they get that if the the because it's founder earnings. So they get that if if the company starts making money. Yeah. And I say, you know, the company is making whatever, 500,000 profit a year. They're gonna say, okay, now it's time to pay back this investment.

Speaker 1:

We don't have equity, but we want a piece until we get to this cap and then you're done. That part sounds nice.

Speaker 2:

Yeah.

Speaker 1:

So let's let's just say that's what's on the table right

Speaker 2:

now. So so the question is how to make this decision. And the thing is, it's not good, better, best. It's not linear. It's not like you can stack rank them, that's why it's a hard decision because it's like, well, this is better for this reason.

Speaker 2:

This is worse for that reason. And they're not comparable things. Mhmm. What's better? The the all the stuff you just said, or working really hard working many more hours.

Speaker 2:

Which one's better? Well, they're not a that there's not the same unit. Mhmm. You can't compare them. Yeah.

Speaker 2:

They're not comparable. Right? So this is why it's hard to make decision because there's multiple dimensions and each one has these trade offs and the units are not comparable, so you can't you can't stack rank them. Yes. You also should not make a rubric.

Speaker 2:

The answer will be they all are sort of good and bad.

Speaker 1:

The other

Speaker 2:

thing You already do that.

Speaker 1:

Sorry to interrupt, but I think the other challenge Yep. With hearing folks online is like, I I admire your writing. Clearly, you've done well in business. I have no idea what your personal life is like. I have no idea what your mental health is like.

Speaker 1:

Exactly. You know, all of these things

Speaker 2:

That's why you can't use that to decide for you. Exactly. I agree. Yeah. You can't.

Speaker 2:

So so because you can't use that and, and, and like, you can't really stack, you can't stack rank, you can't rubric into an answer. So therefore what I think is you can decide there are certain limits or certain thresholds I will not cross. So for example, you could say, you know what? I have four kids and a wife that I'd like to keep, I'm not gonna do anything that that jeopardizes that. Yeah.

Speaker 2:

And if that means I don't have a company, then I don't have a company. Yeah. Now if I can have a company and do that, that is my ideal. That is in fact, that is my goal, and that's exactly what I wanna solve for. But if I have to pick, I know which one I'm picking.

Speaker 2:

Yeah. Or you could say, I have all that, but for the next two years, I understand that I don't want it to suffer, but it might. And that might just be like a pact. Yeah. So so that's what I mean by a limit.

Speaker 2:

Is is there, like, this line you won't cross, this threshold you won't cross that could be about money? It could be about how you put your time? It could be, there could be different things. So that's that's one thing to help because that's not a stack rank. That's a filter.

Speaker 2:

Mhmm. So suppose you said, I will be home at this time and I will you know, let's suppose you said that. You might just filter out right there the possibility of getting a day job, a regular salary job, and doing a start up because you go, you know what? There actually isn't hours to do that. That's not a possibility.

Speaker 2:

However, this other one where I raise money does. So you see that's a fill that's not a stack rank. That's a filter. Filters are good because it reduces the the problem set. Filters are good.

Speaker 2:

So one thing is filter. That's that's one good thing. Another thing is still you'll have more than one probably. Yeah. Because you're probably good at thinking of options.

Speaker 2:

So then, again, there's so many dimensions. That's too hard to try to, like, compare the dimensions. So then you say, alright, I'm gonna just pick one or two things that are gonna be the most important things. And that's that. Yeah.

Speaker 2:

I'm gonna in other words, I'm going to make the decision based on one or two dimensions only.

Speaker 1:

Yes.

Speaker 2:

Even though there's all these other ones, if I don't start ignoring some of this crap, I will never get around because it's circular. This is better than a, but that's better b, but that's better at c, but that's better than a. And like, I have to throw some of this away. Or I can't finally stack rank, you know, actually stack rank. So you, for example, you could say, what makes me the what is most likely to make me the most money?

Speaker 2:

And just do that. Or you could say, what, what you could, if you're a little introspective about what is exciting, what does jazz you up, what is exciting? You say, that's what I want to maximize. And so that might mean I do or don't have control over this or that, or I do or don't have this partner. It happens over this time period or that time period.

Speaker 2:

But like, I wanna maximize doing x or learning x or experiencing x, whatever it is. Yep. You know? And then then then you just solve for that. And you're just like knowing you're trading off the other variables.

Speaker 2:

Yes. I know. That's the point. I gotta decide what I'm not trading off.

Speaker 1:

Yes.

Speaker 2:

Then the rest follows. Another filter example would be this whole question about about whether you would ever want another partner. You already chose one partner because you have a co founder. Yes. Would you ever have another partner?

Speaker 2:

You could say, look, I already have a partner. I've already gone down that road. I don't want to, but like, I'm not going to just filter it out. Or again, you could say, will never have an investor. People say different things and you know what?

Speaker 2:

I don't even, I don't even want to know what the answer is. I don't even want to try to figure out every second I spend trying to figure out if that payout is good or bad or this or that. I'm wasting my life thinking about this. No. The answer is no.

Speaker 2:

Okay. So you could decide to filter that out or not. You could so I think you you set up a couple of filters and you decide, and this is the dimension, maybe two, but, you know, of course, then you get back to another problem if you have too many. So maybe one or two critical things. And you're going to say, I'm going to decide on the basis of just this dimension or maybe two with my filters applied.

Speaker 2:

Then often you can actually get it down to one. You're like, you know what? And but also what's nice is now you know why. So another problem is you could say, I guess I could raise money, but then your brain's still racing around. Yeah.

Speaker 2:

But on the other hand, bad thing, I only had good thing. And you know, it never settles down. So you never feel like, so is that the right decision? And you're like, never feel, but when you filter, you know, I know why that's a no, because this filter.

Speaker 1:

Yeah.

Speaker 2:

And you feel comfortable, like, I know why. And and if it ever pops back up, wait a minute, but nope. Because and you're like, I can put it to bed. And the same thing with the dimension. But this other thing, you're exactly right.

Speaker 2:

It kept the number one most important thing to me is doing x. Yeah. And therefore, you're you're totally right about that other thing. Yes. But and and look, if I can incorporate that other thing a little, I will.

Speaker 2:

Yes. Right? It's it's I I will. But I'm but this is the primary one, that's what I'm doing.

Speaker 1:

Yes. And this, I think, is why people get so passionate, you know, because the, the, the important thing for them, like if you look at Jason and David at 30 at base camp, they have some very important values, some things that they hold on dear to. Yes. And and and they've certainly attracted an audience that also is attracted to those things. And so and so when they are making decisions, they are filtering everything through that.

Speaker 2:

Right.

Speaker 1:

But then someone else can come along and go, but wait a second. Mhmm. That that doesn't match up with the way I feel. You know, and there's certain like the guy that runs Teamwork, you know, he wants to build a totally different project management company.

Speaker 2:

Sure. Good.

Speaker 1:

And again, also what's funny about some of these things is that it's not always, folks that really want who are going after a big success, you know The different goals. Yeah. It's it's it's it really changes things. And so I appreciate you saying that because I think even in my head now, I'm able to think part of this is just about what I value. Why am I doing this?

Speaker 1:

Would I be happy if Transistor made $50,000 a month and it was just John and I and a support person working on this the rest of our lives?

Speaker 2:

That's a good question.

Speaker 1:

Yes. I totally would. That would be a dream. Now that doesn't mean I get that. Like, I might get there, and then all of a sudden, it's like Peltie at Balsamiq.

Speaker 1:

He wants it to be a one person company, but it turns into something bigger.

Speaker 2:

I've been making fun of that for but to him and good naturedly since he started.

Speaker 1:

Yes. Yeah.

Speaker 2:

Hey, Pelli. How's that how's that little cafe in the corner going? Yeah. We hired another 10 people. Well, you know, don't do that.

Speaker 1:

And and obviously, what you want changes. Like, when you started out, you were just excited about building something interesting and having people pay about it. But as you moved along, what you wanted changed. Yeah. Now you get jazzed up about diversity.

Speaker 1:

You get jazzed up about your culture. You get I don't give I mean, I don't I shouldn't say I don't give a shit about our culture. We think a little bit about culture, but it's just John and I.

Speaker 2:

It's too small it's too small to worry about that.

Speaker 1:

Yeah. But now, at your stage, you're thinking about those things. And, yeah, I think that that maybe to close this off, do you think because at one point I had this ideology that I thought everybody, well, I I thought everybody should make things and try to earn a little bit of independent income on the side just because I I always felt like that was healthy. For me, it always made me feel like I've got a little something.

Speaker 2:

It sounds like advice to me.

Speaker 1:

That sounds like advice. Just true. But the, you know, I'm realizing how hard this is. And, you know, it would certainly it it feels like there's a big part of this that if you don't really, really want it, you should never sign up for it.

Speaker 2:

Well, you know, I I know what you're saying because it's like look. It's it's it's incredibly hard. It's difficult to describe how hard it is to someone who hasn't done it before. Kind of like you can't describe what having kids is to someone who hasn't had And you're like, having kids is hard. You're like awake all the time, and you're worried about them, and you're trying not to kill them, and you're not even sure how to not kill them.

Speaker 2:

You're just hoping they sort of don't die. And and and it's and it's weird. And and and other people are like, yeah. No. I I get that.

Speaker 2:

And you're like, no. You don't. You you just get your car keys and go to dinner, and we never do that. Mhmm. So you don't get it.

Speaker 2:

You know? Like, you can't describe it. And this is the same way. You just can't describe what it's like when you're in the hole. And you're and everyone's and everyone else goes, $4,300 in a couple months.

Speaker 2:

That's great. You're like, couple months, I've been, like, obsessed to the point of, like, not being able to sleep for a year and also money and things and and, like

Speaker 1:

Yeah. And also

Speaker 2:

You can't you can't describe it. To be honest, my whole life

Speaker 1:

has been leading like, it's not just like it's not just like I've been thinking about this for four months. Been thinking about some of this stuff since I was a kid. Like, there's a long process.

Speaker 2:

It's like, Peltier is a great thing about that too. Right? And and I think yeah. And that's so this is this is the doldrums where you really have to say, so I really have to do I have to go through this crucible. Mhmm.

Speaker 2:

If this is gonna work. And the answer is yes.

Speaker 1:

Mhmm.

Speaker 2:

Yeah. Now there's a couple of choices. You could try to raise money. You know? Okay.

Speaker 2:

We already went through all that. Yeah. So you could try other paths. But, ultimately, like, yeah. Yeah.

Speaker 2:

There's there's there's something's gonna give, and that could be, equity to an investor or other kinds of things. Like you were saying structure. It's usually what the finance guys call it as structure. Yes. You either give up some structure or some equity or some control like with you already gave up some because you have a co founder.

Speaker 2:

Some people have three. There you go. More more control loss. You give up that or you give up your life time. It takes something to get these things going.

Speaker 2:

They don't just go, and, yes, I know we can all find somebody where it just went. Okay. Good for you. Yeah. For every one of you, there's a thousand of us who have to struggle and not struggle porn.

Speaker 2:

That's very, very bad. Yeah. But it is hard. It is hard for a little bit. Like, that's also true.

Speaker 2:

Like, there's you can you can be against the glorification of struggle Yeah. But still recognize it. That doesn't mean there's never struggle. Like, of course, there is like, that's that's ridiculous to say it's not hard. That's just in fact, that's insulting Yeah.

Speaker 2:

To say to for DHH to say it's it's easy is insulting. And that yes. No. It's not. Yeah.

Speaker 2:

No. It's not. And by the way, remember he admitted later in that Twitter thread, but not at first. Yeah. Well, actually, everybody there was four people working on it part time.

Speaker 2:

So actually, was like forty, sixty hours a week being put into that side project. Oh, I see.

Speaker 1:

I see what you're saying. Yeah.

Speaker 2:

Great. So, like, all it takes is full time. That's what I was saying. Yes. Now one way to do it is their way, which is to give up control by having four cofounders.

Speaker 1:

Yes.

Speaker 2:

Great. But just just say that. Don't pretend like it it takes ten hours a week. That's wrong.

Speaker 1:

Well, in their case, two cofounders, but two other full time people.

Speaker 2:

Yeah. Oh, where did they get the money for that? Oh, we already had an agency going. Oh, so we had a day job

Speaker 1:

Yeah.

Speaker 2:

Which then paid for the doing this, which they could have dividended out, but not by first getting an agency going.

Speaker 1:

Yeah.

Speaker 2:

Okay. This is a totally different story. Yes. Exactly. It takes forty hours a week of work.

Speaker 2:

This is the way they did it, which, by the way, is great. No problem. Just say. What we did is we built an agency which then funded product that still took us two years after that of doing that, but with one maybe one and half people full time's worth of work, and then we got it to work. Right.

Speaker 2:

That's what I've been saying. It takes something like forty hours a week of work for something like two years to get the damn thing off the ground. Maybe that's two cofounders at twenty hours a week or something like But, yes, that's what it takes. Yeah. Okay.

Speaker 2:

We're all say actually saying the same thing if we're being honest about what it takes to get it going.

Speaker 1:

Yes.

Speaker 2:

Okay. But, also struggle porn's bad. So because because that's presented like somehow you're winning or successful by being totally underwater and not and and and ignoring your family.

Speaker 1:

Mhmm.

Speaker 2:

So, like, struggle point is bad because it's glorifying a problem. Like, the the the reason we're you're in this situation is because the company's not going yet. Yeah. It's just getting started. It isn't successful yet in that sense, the in sense that you want, which is that it's paying the bills.

Speaker 2:

Yeah. Just to be clear, what we mean by success, it's your definition, the one where it's paying your bills. That Yeah. I want some money. Yes.

Speaker 2:

In that definition, it's no it's not successful yet because it just started. I think it's on a good trajectory, but Yeah. It's not at that point yet. Okay. So the reason you're gonna have to struggle and put all the money or I mean, all the time or whatever Mhmm.

Speaker 2:

Is because it's not working yet. Yeah. It's a bad thing. It's not a good thing that you have to do it. Yeah.

Speaker 2:

The problem with struggle porn is it says, this is a good thing. I'm working so hard, and I'm such a hustler. Yeah. And and the glorifying that, no. It's the that in fact is a symptom of the problem, which is that the business isn't going yet.

Speaker 2:

It's not yet a real business. Yeah. In the way that you want. Again, just clarifying in the way that you want. Yes.

Speaker 2:

Of course, it's okay if you want money on the side, then do it the side. It's cool. Yeah. That's not what you want. Yes.

Speaker 2:

Therefore, it's not doing what you want. So it's we shouldn't it should it shouldn't be glorified. Of course, you are not. You're saying that this sucks. Exactly.

Speaker 2:

Now that now we're struggling, but we're being honest. Struggle porn is it's supposed to be like this, and it's awesome, and I'm successful because I'm struggling. It's like, no. You're struggling because it's not working yet. Yeah.

Speaker 2:

And then continues. Let's say you have a team of 10 people and you've got struggle porn still. Yeah. Why? Why why are you still working hundred hour work weeks with the team?

Speaker 2:

Again, it's because you're failing as a leader. Yeah. Maybe it's because you're micromanaging everyone. That's why it takes so much time because you're doing everyone's job. Well, that's a leadership failure if you're doing that to people.

Speaker 2:

Yeah. Well, maybe you're doing that to people because they're not competent enough. Well, that's a leadership failure because you hired them.

Speaker 1:

Yeah.

Speaker 2:

Oh, well, maybe it's they are competent, you're just overbearing and not letting them do their job. Well, that's a leadership failure because you're supposed to hire people that can do the job and then let them do that.

Speaker 1:

Yeah. Yeah.

Speaker 2:

And and courage and edit and stuff like that, but not do it for them or not you know? In other words, no matter what stage you're at, that's still small. Of course, it's still true when it's big. But even just from that zero employees to take 10 employee range, it's always a failure mode if that's what's going on. Yes.

Speaker 2:

Now the difference is at 10 people, like, you just shouldn't need to do that anymore. So you're really in trouble. Early on, I feel like, yeah, that's just where we're at. Like, it's not good, and we should try to get out of it. Yeah.

Speaker 2:

Let's just not glorify it. But on the other hand, let's not say, like, somehow like, again, how insulting is it to say, like, somehow you're a failure because you you don't have a business making $20 a month after four months? Yeah. That's insulting and not true.

Speaker 1:

Yeah. Yeah. I think what's helpful, especially in the high fidelity that this is right now, is the because I can hear your story and then I can think of my story. And I can think, you know, there are certain things that are just true. Like for most people in North America, if you've been working on something and committing a fair amount of energy to it for three years, dollars 20,000 a year in revenue is probably, not a good use of your time and you should move on.

Speaker 1:

But in the meantime, everybody has to make hard decisions. It's not like it's or most and maybe there's a lucky few that don't. But this idea of trade offs and really looking at those and deciding for you which ones you're willing to make and which ones you're not, that's just the journey. That's the journey for everybody.

Speaker 2:

It's hard.

Speaker 1:

Yeah. Well, I think that's probably good. You've been very kind with your time. I really appreciate it. Apologize, by the way, for folks watching live.

Speaker 1:

I had some hiccups there. I know some of you were able to stay the whole time. I'm going to package this up and publish it on the Product People podcast. Yeah. Is there is there anything else that you're doing these days that you want people to know about on your blog or on WPN?

Speaker 2:

Because the company is a full time job, and my other choice is family. And so I'm not doing other things. I'm not even really I'm not a I used to do more, like, investing or advising or something like that. And I, in fact, sadly, write very infrequently on the blog too, which I hope that it would be nice if I did more of, I guess. But but I also understand exactly my own advice, and so I understand what I'm doing.

Speaker 2:

So, no, I'm not really WP Engine is is absolutely, you know, more than a full time job. Yeah. So there it Do

Speaker 1:

you just to close, do you still like it? Like, is it still fire you up, and is it still hard?

Speaker 2:

Well, it's definitely hard. Yeah. That was that's the easiest one to answer. It's definitely still hard.

Speaker 1:

Still hard?

Speaker 2:

Oh, very hard, but just different reasons.

Speaker 1:

Yeah.

Speaker 2:

You're not we're not worried whether, like, we you know, will we have hundreds of people sign up tomorrow as new customers? The answer is yes Yeah. With very high degree of certainty. So I'm not worried about that. Wow.

Speaker 2:

There's so much else. How do you feed and grow 600 people? You can't do that with a small product release. Yeah. Any idea you have which might make a couple million dollars a year isn't worth doing.

Speaker 1:

Yeah.

Speaker 2:

Well, then what are the ideas that can make tens of millions of dollars a year? It's actually, like, almost impossible to think of those ideas. It's hard. Yeah. So what do we do?

Speaker 2:

Yeah. See, right back to what do you do? Yeah. Strategy at that level, it's global as well. That's complicated.

Speaker 2:

And here's here's a great example of of something that's hard, that's not hard when it's small, but definitely hard here. So we're big enough where everything that happens to human beings happens pretty frequently. People have a new baby.

Speaker 1:

Mhmm.

Speaker 2:

There's a people get married. People get divorced. Mhmm. People die. Mhmm.

Speaker 2:

Our own employees die. We have to deal with that. Yeah. They die in different ways. We have to deal with that.

Speaker 2:

Yeah. Or very or, you know, someone's kid or something, you know, really, really devastating. Yeah. So the the things that happen, though, we're still small enough that everybody knows, like, either knows that person directly or know like, it's just one step away and really kinda feels it like, oh, wow. Yeah.

Speaker 2:

I remember that guy. You know? Yeah. So, therefore, there's this constant, actually, quite difficult barrage of humanity Yes. But small enough that, like, everyone is, like, experiencing that semi directly all the time.

Speaker 2:

Yeah. That's hard. Yeah. And, like, it it's an unexpected, like, what about organizational structure? Like, yeah, that's hard too, but, like, there's other stuff too that's, like, you don't really think about Yeah.

Speaker 2:

Necessarily that that just appears. And and clearly, it's not like, oh, here's what you here's what you do. And, like, you've made a tactical error. Like, no. No.

Speaker 2:

That's what it is. Right? Yeah. There's really nothing to do except try to manage that, well. Yeah.

Speaker 2:

So so no, there's lots of things that are hard. Think in terms of fun, I think, it comes it it it goes like this. And and what happens is you just have to, as I said before, be really honest about what do I like? What am I good at? What does the company need?

Speaker 2:

Yeah. Those are the three things. What do I like? What am good at? And there's failure modes whenever one of those things or, I guess, more than one are not true.

Speaker 2:

So, like, if I'm doing something I'm good at and the company needs, that sounds good. Mhmm. Because if I don't like it, I burn out. Yeah. And I say I.

Speaker 2:

It's anybody. Obviously, I'm just speaking for myself. But, obviously, what I really mean is for anybody in any situation. Right?

Speaker 1:

Yes. Totally.

Speaker 2:

So so that's not a great mode for very long. Yeah. But if you do something you like but are not good at, it's not really helpful. Yes. Or you like it and the company needs it, but you're not the best.

Speaker 2:

Yeah. Well, at at ours now when you're small, perfect because whatever. Yeah. Yeah. We're not the best at almost anything.

Speaker 1:

Keep moving. Right? Good enough.

Speaker 2:

Yeah. At our size, though, it's actually not okay. Because if the company needs it, whatever it is, we also need it to be really good, or else we're not gonna do it at all. Mhmm. Yeah.

Speaker 2:

We don't just, like, kinda figure it out. Like Yeah. If it's that important, we need, like, probably a whole team and a leader who knows it's a whole thing. Yeah. They're like, oh, we'll just kinda wing it.

Speaker 2:

Well, we the things that are important enough to really demand action are important enough that we can't just wing it anymore. It's too hard or specialized. Mhmm. So therefore, I like it when the company needs it. It's no longer an excuse.

Speaker 2:

That's a failure mode at scale.

Speaker 1:

Yeah.

Speaker 2:

Not a failure mode early, but at some point it's a failure mode.

Speaker 1:

Mhmm.

Speaker 2:

So, you know, that's a mode where you're just not getting excellence on something you need. There's a failure mode of you like it and you're good at it, but the company doesn't need you to do it. Yeah. I fall into that sometimes.

Speaker 1:

Mhmm.

Speaker 2:

I would love to code this up, and I'm good at it. Yeah. And I get in the zone. Yeah. And also we don't need it.

Speaker 2:

It's not it's not moving the needle on anything that we need to do. Yeah. So as a founder, it's very easy to get into that found failure mode because usually no one's telling the founder what to do. Yeah. So you're if doing something that you like and you're good at, no one tells you stop it.

Speaker 2:

We need you to do sales, not code. Like, no one usually grabs you by the collar and tells you that. Mhmm. And that's why it's a failure mode. That's why it's hard.

Speaker 2:

That's why you're being introspective about the whole thing. Yeah. So structure I use to decide not to be CEO. Like, I use that very thing to decide something as important and big as I'm not the right person for the CEO. Yeah.

Speaker 2:

Because the company needs this and that as a CEO. Many companies do once you get to a certain size. I mean, we were around sixty, seventy people at that point. Yeah. And what am I good at?

Speaker 2:

Not that. Not leading huge groups of people and managing and hiring executive team and with the caliber that we need to open global offices and blah blah blah blah. Number one, that's not my expertise. And number two, that sounds like hell to me. Yeah.

Speaker 2:

And what the company deserves is somewhere not only is it her expertise, and it is a her in our case, by the way. I'm not just doing that to do whatever. It's it is a her.

Speaker 1:

So not only is

Speaker 2:

it her expertise, she it it is her it is her favorite job.

Speaker 1:

Yeah. She loves it.

Speaker 2:

That's what's everyone deserves. It's what the company deserves too, by the way. And I deserve it as a founder. I deserve to not get burnt out on doing something that I'm not good at the communities. I deserve it.

Speaker 2:

We all deserve it. This is a good thing. Yeah. So I think I think keeping that in mind is the right mentality, whether you're at scale and in leadership, whether you're just got a job and just trying to figure out what's my career path. Or if you're a founder and navigating exactly what you're doing and you can, and you're asking these questions about if I'm not going to get burned out, what's going to happen here.

Speaker 2:

That's a, that is a good framework. I don't I've been using that framework for a while, and I've written about it and I've talked about it. I'm pretty sure, like, you can find frameworks that are almost the same all over the place. Like, it's not like this is super unique. It's just my particular way of doing that particular thing.

Speaker 2:

Yeah. That that works for me anyway. And so that's what I used to decide. So so when you ask like, do do you like what you're doing?

Speaker 1:

Yeah.

Speaker 2:

Often. Yes. Life doesn't let you do that all the time. But I do. I try to be introspective in that, with that exact, framework with that way to ask how can I do what I like the most, the most?

Speaker 2:

Yeah. But with those other constraints, because then I'm healthiest and also the business is healthiest and everyone in the business should be trying to do that. And I tell people that we use that to help people figure out their careers and such.

Speaker 1:

Yeah. Now that's been it's this has been very, helpful for me, I think, just in terms of

Speaker 2:

Hey. Doctor. Laura worked.

Speaker 1:

Yeah. Doctor. I

Speaker 2:

didn't tell you you were shit enough.

Speaker 1:

You're shit. Yeah. You gotta you gotta you gotta give me a hard time.

Speaker 2:

Yeah. I need to give you a hard time.

Speaker 1:

I mean, I think that yes. The the part that's hard is just that it's hard. And the part that's hard is that I'm not Jason Cohen and I'm

Speaker 2:

in No. A That's not it because I was hard it's hard for me too. Like, it's just hard.

Speaker 1:

Yes. Totally. Exactly. I that part that perspective has been helpful. Thanks so much for your time, Jason.

Speaker 2:

Thank you. This was fun.

Speaker 1:

Thanks again, folks, for showing up, for pushing play on this in your podcast player. I hope that discussion was helpful for you. If you'd like to see the video version of that, it's on my YouTube channel, youtube.com/justinjackson. If you want to read the blog post that kinda kicked this whole thing off, it's at justinjackson.ca/sideproject. And, yeah, you can always reach out to me on Twitter.

Speaker 1:

I'm the letter m, the letter I, Justin. Again, Mega Maker's going to be opening up again soon. Go to megamaker.co. And, if I don't talk to you before the holidays, have a great holiday, and I will see you in the New Year 02/2019.

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Creators and Guests

Justin Jackson
Host
Justin Jackson
⚡ Bootstrapping, podcasting, calm companies, business ethics. Co-founder of @transistorfm (podcast hosting).
Jason Cohen
Guest
Jason Cohen
Keyword, buzzword, half-truth, adjective, hey look at me! (founder of two unicorns: https://t.co/Cc4OvZx0T9, https://t.co/JTEGCe7Zq6)

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